institute of advanced chemistry of catalonia - IQAC-CSIC

Biennial Report 2010-2011

INSTITUTE OF ADVANCED CHEMISTRYOF CATALONIA

Institut de Química Avançada de Catalunya (IQAC)

LIBRO IQAC. pags.1 a 104:Maquetación 1 11/6/12 10:30 Página 1

INSTITUTE OF ADVANCED CHEMISTRY OF CATALONIAInstitut de Química Avançada de CatalunyaConsejo Superior de Investigaciones CientíficasJordi Girona, 18-2608034 Barcelona. SpainPhone: +34 934 006 100Fax: +34 932 045 904http://www.iqac.csic.es/

Editor: José Coll ToledanoWith the collaboration of Lidia BeltránN of copies: 200Legal deposit: B-19014-2012

Printed in Catalunya, GRAFISMAR, S.A., Barcelona


INDEX

IQAC Biennial Report 2010-2011

DIRECTOR’S FOREWORD

1. STRUCTURE AND GENERALRESULTS

2. DEPARTMENT OF BIOLOGICALCHEMISTRY AND MOLECULARMODELLING

3. DEPARTMENT OF BIOMEDICINAL CHEMISTRY

4. DEPARTMENT OF CHEMICALAND BIOMOLECULAR NANOTECHNOLOGY

5. DEPARTMENT OF CHEMICALAND SURFACTANTS TECHNOLOGY

6. FACILITIES AND TECHNOLOGYTRANSFER

5

HISTORY 9INSTITUTE BOARD MEMBERS. ADMINISTRATION.«AD HONOREM» MEMBERS. 10DEPARTMENTS AND RESEARCH GROUPS. IQAC FACILITIES 11NUMERICAL SUMMARIES 122008-2009 JOURNAL PUBLICATIONS SUMMARY 13LIST OF ISI JOURNALS 14SPECIAL EVENTS. AWARDS AND NOMINATIONS 15

DEPARTMENT INTRODUCTORY REMARKS 19NUTRACEUTICALS AND FREE RADICALS 20BIOTRANSFORMATION AND BIOACTIVE MOLECULES 23SUPRAMOLECULAR CHEMISTRY 26ECOLOGICAL CHEMISTRY 28THEORETICAL AND COMPUTATIONAL CHEMISTRY 31BIOLOGICALLY ACTIVE PHYTOCHEMICALS 35

DEPARTMENT INTRODUCTORY REMARKS 39RESEARCH UNIT ON BIOACTIVE MOLECULES 40SYNTHESIS AND BIOMEDICAL APPLICATIONS OF PEPTIDES 43UNIT OF GLYCONJUGATE CHEMISTRY 45

DEPARTMENT INTRODUCTORY REMARKS 49NANOBIOTECHNOLOGY AND MOLECULAR DIAGNOSTICS 50NUCLEIC ACIDS CHEMISTRY 53COLLOID AND INTERFACIAL CHEMISTRY GROUP 57BIOORGANIC CHEMISTRY 61SURFACE CHEMISTRY GROUP 64

DEPARTMENT INTRODUCTORY REMARKS 69MINIMIZATION OF INDUSTRIAL WASTES: ISOLATION OF HIGH ADDED-VALUE BIOPOLYMERS 70DEVELOPMENT OF NON-CONTAMINANT INDUSTRIAL PROCESSES 73STATISTICAL MODELLING AND FIBRE PHYSICS 75BIOCOMPATIBLE SURFACTANTS 78ENVIRONMENTAL CHEMISTRY OF SURFACTANTS AND IONIC LIQUIDS 81PHYSICAL CHEMISTRY OF SURFACTANT SYSTEMS 84BIOPHYSICS OF LIPIDS AND INTERPHASES 86

IQAC FACILITIES AND TECHNOLOGY TRANSFER 93CHARACTERIZATION OF COLLOIDAL DISPERSIONS SERVICE 94CUSTOM ANTIBODY SERVICE (CAbS) 95ORGANIC MICROANALYSIS SERVICE 96BIODEGRADATION AND AQUATIC TOXICITY SERVICE 96MAGNETIC RESONANCE SERVICE 97SKIN ABSORPTION and SKIN EFFICACY SERVICES 98SYNTHESIS OF HIGH ADDED VALUE MOLECULES SERVICE 99SAXS-WAXS SERVICE 100THERMAL ANALYSIS SERVICE 100PROTEOMICS SERVICE 101TECHNOLOGY TRANSFER 102


7. APPENDIXES

8. APPENDIXES CONTENTS(in CD version)

APPENDIX 1. OTHER RESULTS AND EVENTS 107

APPENDIX 2. SCIENTIFIC OUTPUT 107

8.1 APPENDIX 1. OTHER RESULTS AND EVENTS 109

Research funding 110Granted research projects 115

Running funded research projects and contracts 119Patents 122Ph. D. Thesis 126Masters-D.E.A. 129Academic activities 129Invited conferences and Key lectures 130Oral and poster contributions 132Other activities 138

8.2 APPENDIX 2. SCIENTIFIC OUTPUT 139

Publications in ISI journals (Journals in alphabetical order) 140Publications in non-ISI journals (Journals in alphabetical order) 151Book chapters 152


The Institute of Advanced Chemistry ofCatalonia (IQAC) is one of the researchcenters of the Consejo Superior deInvestigaciones Científicas (CSIC). TheInstitute is located in Barcelona and it wascreated to do research of excellence focusedon basic chemical sciences, but alsoaddressed to solve specific problems of oursociety by using tools from the chemistry-biology interface, theoretical chemistry,chemical and biomolecular nanotechnologyand sustainable chemistry. In particular, theidentification of niches where our expertisecan make important contributions issystematically pursued. Equally important toall of us is to be in a permanent attitude totransfer our knowledge and technologyresults to the industrial sector.

The present Report covers the biennium2010-2011. It gives an account of ourresearch activity and of the mainobjectives achieved during this period.

The analysis of the data herein reportedpermits to conclude that the mission thatinspired the creation of our Institute isbeing successfully accomplished. Wedeem that the expertise and the intenseefforts of all our personnel havecontributed to consolidate our scientificproject at the international scale.

In addition to the information given here,we invite you to navigate our website(www.iqac.csic.es). There, you will findadditional information about theresearch problems that we face and theirresults and perspectives. The web pagecontains also details about the facilitiesand methodologies that we can offer tothe scientific community, both from thepublic and the private domains, tocomplement or improve their ownprojects, or those that can be put in theframe of a joint initiative. In this sense,the research groups and technical servicesfrom our Institute will be wide open toattend your inquiries and to offer theirbest efforts to find adequate responses toyour needs, based on their backgroundand expertise.

Yours faithfully,

Àngel MesseguerDirector of IQAC

5

DIRECTOR’S FOREWORD


STRUCTURE AND GENERAL RESULTS

1


HISTORY

9

The Institute was created in 2007 to better accommodate the interests of scientists of the Chemistry areas

working at the "Center of Investigation and Development" (CID) and to provide a greater external projection

of the activities of these scientists within the frame of the Spanish Research Council (CSIC). In spite of its

recent creation, the Institute inherits the long and fruitful research tradition in Organic Chemistry initiated by

Prof. José Pascual Vila since 1940. After finalizing his activity in the University, in 1967 Prof. Pascual Vila

moved with his co-workers of CSIC into the Institute of Organic Chemistry of Barcelona in CID. At the same

time, CSIC scientists working on Chemical Technology, such as those related to the textile and leather fields,

were also incorporated into CID. During many years the CID has been the referent of the CSIC Chemistry in

Catalonia and of the organic and bioorganic chemistry research in our community. Many graduate students

and post-docs formed in this Center have moved to relevant positions in academic institutions (Universities,

CSIC) and in private sector. In 1996, a joined action of the bioorganic, theoretical and technological groups

together with those working in chemical issues related to the environment, led to the creation of the Institute

of Chemical and Environmental Research "Josep Pascual Vila" (IIQAB). During the ten-year period of IIQAB,

research groups have adapted their objectives to the new demands of society and new groups have also been

generated. From these efforts, the Biological Chemistry, Theoretical and Computational Chemistry,

Sustainable Chemistry and selected items of Chemical Technology have been reinforced. Concomitantly,

potent groups working on Chemical and Biomolecular Nanotechnology have emerged or have been

incorporated into IQAC. Actually, this set of scientific interests, in which the apparent heterogeneity of the

active research areas is clearly compensated by the wide opportunities of their mutual interaction, justifies

the creation of IQAC as a solid and modern Institute that looks at the future leaning on two pillars: the

enthusiasm and expertise of its personnel and the robustness of the Chemistry tradition in our Centre.

Although its creation was in 2007, the research groups incorporated into IQAC have a recognized

international prestige in their research fields. Among others, it should be highlighted the design, synthesis

and evaluation of molecules of therapeutic, pharmacological or biological interest, the chemistry and

applications of surfactants, the study of hormones and enzymatic transformations in insects, the development

of environmentally friendly technologies, the treatment of industrial waste, the research in peptides and

proteins, the theoretical study in electronic structure, or the application of nanotechnological approaches to

the understanding of nanoscale systems and the development of novel nanomaterials and nanodevices, such

as bioanalytical tools based on the combination of tailored bioreceptors, new nucleic acid derivatives and

well-defined nanostructures and advanced materials.

In addition, our Institute has a set of scientific and technical facilities that offer services to the IQAC research

groups as well as to groups or companies from elsewhere: Thermal Analysis and Calorimetry, Magnetic

Resonance (NMR and EPR), Organic Microanalysis, Synthesis of High-Added Value Molecules, X-Ray

Dispersion at Small Angle (SAXS-WAXS), Characterization of Colloidal Dispersions, Percutaneous Absorption

and Skin Efficacy, Monoclonal Antibodies Production and Characterization (CAbS), Biodegradation and

Aquatic Toxicity, Proteomics and Technology transfer.


INSTITUTE BOARD MEMBERS

10

Àngel Messeguer Peypoch DirectorRosa Infante Martínez-Pardo Deputy DirectorJoan Ricard Ibáñez Villar Head of AdministrationJesús Joglar Tamargo Department of Biological Chemistry and Molecular ModellingGemma Fabriás Domingo Department of Biomedicinal Chemistry Mª Pilar Marco Colás/ Department of Chemical and Biomolecular Nanotechnology Jordi Esquena MoretRamón Pons Pons Department of Chemical and Surfactants TechnologyJaume Caelles Balcells Personnel RepresentativeAvencia Diez Ortego Personnel RepresentativeMeritxell Martí Gelabert Personnel RepresentativeJosep Carilla Auguet/ Invited Services Representative Pilar Domènech Duran

ADMINISTRATIONDirector: Àngel Messeguer PeypochDeputy Director: Rosa Infante Martínez-PardoHead of Administration: Joan Ricard Ibáñez VillarSecretaries: Lídia Beltran Fabregat

Josefina Estremera SoléLeonor Moliner Ferrer

«Ad honorem» MEMBERSM DOLORS DE CASTELLAR BERTRANPILAR ERRA SERRABASA


DEPARTMENTS AND RESEARCH GROUPS

11

Department of Biological Chemistry and Molecular Modelling Nutraceuticals and Free Radicals Biotransformation and Bioactive Molecules Supramolecular Chemistry Ecological Chemistry Theoretical and Computational Chemistry Biologically Active Phytochemicals

Department of Biomedicinal ChemistryResearch Unit on BioActive Molecules Synthesis and Biomedical Applications of Peptides Unit of Glycoconjugate Chemistry

Department of Chemical and Biomolecular NanotechnologyNanobiotechnology and Molecular Diagnostics Nucleic Acids Chemistry Colloid and Interfacial Chemistry Group Bioorganic Chemistry Surface Chemistry Group

Department of Chemical and Surfactants TechnologyMinimization of Industrial Wastes: Isolation of High Added-Value Biopolymers Development of Non-contaminant Industrial Processes Statistical Modelling and Fibre Physics Biocompatible Surfactants Environmental Chemistry of Surfactants and Ionic Liquids Physical Chemistry of Surfactant Systems Biophysics of Lipids and Interphases

IQAC FACILITIES AND TECHNOLOGY TRANSFERCharacterization of Colloidal Dispersions Service Custom Antibody Service (CAbS) Organic Microanalysis Service Biodegradation and Aquatic Toxicity Service Magnetic Resonance Service Skin Absorption and Skin Efficacy Services SAXS-WAXS Service Synthesis of High Added Value Molecules Service Thermal Analysis and Calorimetry Service Proteomics ServiceTechnology Transfer


PERSONNEL Staff Technicians Ph. D. Ph. D. Students

BCMM 14+1a 2 9 20

BMC 9 7 6 16

CBN 10+1b 5 25 33

CST 16+1b 10 9 6

Services 3 6

TOTAL 52+3 30 49 75a in SC. b «ad honorem».

ACADEMIC OUTPUT PhD Thesis Masters Courses Conferences

BCMM 10 5 6

BMC 6 1

CBN 9 3 6 8

CST 5 2 2 13

TOTAL 30 6 13 27

SCIENTIFIC OUTPUT ISI Journals No-ISI int No-ISI nat Book ch.

BCMM 91 (95†4;*7) 1 2

BMC 46 (46;*5) 2

CBN 87 (96†9;*3) 7 (+1ed) 2 7 (9†2)+1N

CST 63 (87†22,23;*1) 3 1 8 (11†3)

TOTAL 279 (287-8) 13 (+1ed) 3 17

*Common publications in two entries. † Common publications in one department (duplicated or triplicated). N National

Staff Staff Technicians Ph. D. Ph. D. Students

Papers in ISI journals Papers in non-ISI int Book chapters

Ph. D. Thesis Masters Courses Conferences

NUMERICAL SUMMARIES

12


Budget in 2010

Budget in 2011

PROJECTS 2010 budget 2011 budget

NP started 151.624,1

8656,5

NP running 15

EU started 291,3

3460,6

EU running 6

AACC started 7115,2 124,2

AACC running 8

CR/Services

537,947,9

590,469,3

Facilities Ext (Int)

62,9(94,7)

167,9(148,8)

Funds (other) 232,1 117,8

TOTAL 2.751,4 2.186,7

NP: National Project; EU: European Union; AACC: AutonomousCommunity; CR: Contracted Research

Total number of ISI-journals: 152

with one paper: 94 (61.84 %)

with more than one paper: 58 (38.16 %)

with , or papers: 31 (2); 10 (3); 7 (4)

with or more papers: 10

[4 (5); 2 (6); 2 (7); 1 (9); 1 (10)]

Total number of papers: 279

Papers in Non-ISI journals, international: 13

five

fourthreetwo

single

TECHNOLOGICALOUTPUT

2010 2011TOTAL

SPA PCT L SPA PCT L

BCMM 1 2 1 4

BMC 4 4 3 3 14

CBN 7 6 2 2 7 2 26

CST 1 4 1 1 7

TOTAL 13 16 2 6 12 2 51

SPA: Spanish patent application; PCT: Patent cooperation treaty;L: licensed

2010-2011 JOURNAL PUBLICATIONS SUMMARY

13


JOURNALS 2010 2011 JOURNALS 2010 2011 JOURNALS 2010 2011ACS Appl. Mater. Interfaces 1 1 Eur. J. Med. Chem. 1 J. Pept. Sci. 1

ACS Med. Chem. Lett. 1 Exp. Eye Res. 1 J. Pest. Sci. 1ACS Nano 1 Fiber. Polym. 2 J. Pharm. Sci. 1

Acta Biomater. 1 Food Chem. 2 1 J. Phys. Chem. A 1Adv. Synth. Catal. 1 3 Front. Ecol. Environ. 1 J. Phys. Chem. B 1

Amino Acids 1 Glycoconjugate J. 1 J. Phys. Chem. C 1Amyloid-J. Protein Fold. Disord. 2 Green Chem. 2 1 J. Rheumatol. 1

Anal. Bioanal. Chem. 1 2(1E) Ind. Eng. Chem. Res. 1 J. Soc. Leather Technol. Chem. 2 1Anal. Biochem. 2 Insect Biochem. Mol. Biol. 1 J. Surfactants Deterg. 3 1

Anal. Chim. Acta 1 Insect Mol. Biol. 1 J. Therm. Anal. Calorim. 2 1Analyst 1 Int. Biodeterior. Biodegrad. 2 Langmuir 7 3

Angew Chem.-Int. Ed. 2 Int. J. Biol. Macromol. 1 Magn. Reson. Chem. 1 1Anti-Cancer Agents Med. Chem. 2 Int. J. Dermatol. 1 Mater. Chem. Phys. 1

Anti-Corros. Methods Mater. 1 Int. J. Energy Res. 1 Med. Res. Rev. 1Arkivoc 1 Int. J. Mol. Sci. 2 Mol. Biosyst. 2

Biochem. Eng. J. 1 Int. J. Pharm. 1 1 Mol. Divers. 2Biochim. Biophys. Acta-Biomembr. 2 Int. J. Quantum Chem. 1 Mol. Inform. (QSAR Comb. Sci.) 1Biochim. Biophys. Acta-Gen. Subj. 1 Int. Rev. Phys. Chem. 1 Mol. Nutr. Food Res. 1

Bioconjugate Chem. 2 J. Adhes. Sci. Technol. 1 Mol. Ther. 1Biomicrofluidics 1 J. Agric. Food Chem. 3 6 Molecules 1

Bioorg. Med. Chem. 2 J. Am. Chem. Soc. 4 Nanoscale Res. Lett. 1Bioorg. Med. Chem. Lett. 1 J. Am. Leather Chem. Assoc. 3 2 Nat. Prod. Commun. 1

Biophys. J. 1 1 J. Am. Oil Chem. Soc. 1 Org. Biomol. Chem. 1 4Bioresour. Technol. 1 J. AOAC Int. 1 Org. Lett. 1

Biosens. Bioelectron. 2 1 J. Appl. Phys. 1 Pest Manag. Sci. 1Can. Entomol. 1 J. Appl. Polym. Sci. 1 1 Phys. Chem. Chem. Phys. 2 3

Carbohydr. Polym. 2 1 J. Biol. Chem. 2 4 Physiol. Entomol. 1Catal. Today 1 J. Cereb. Blood Flow Metab. 1 Phys. Rev. Lett. 1

Chem. Biodivers. 1 1 J. Chem. Ecol. 1 Plant J. 1Chem. Biol. 1 J. Chem. Inf. Model. 1 PLoS Comput. Biol. 1 1

Chem. Biol. Drug Des. 1 J. Chem. Theory Comput. 1 2 PLoS one 2Chem. Commun. 2 3 J. Chromatogr. A 1 Polym. Advan. Technol. 1

Chem. Mat. 1 J. Chromatogr. B 1 Polym. Compos. 1Chem. Rev. 1 J. Colloid Interface Sci. 3 4 Prog. Lipid Res. 1

Chem.-Biol. Interact. 2 J. Control. Release 1 Prostate 1Chem.-Eur. J. 4 2 J. Cosmet. Sci. 1 1 Proteins 1

ChemBioChem 1 1 J. Dispersion Sci. Technol. 1 Russ. J. Gen. Chem. 1ChemCatChem 1 J. Electroanal. Chem. 1 Small 2

ChemMedChem 1 1 J. Exp. Nanosci. 1 Soft Matter 4Chemosphere 1 1 J. Hazard. Mater. 3 Synlett 1

ChemPhysChem 1 1 J. Immunol. 1 Synthesis 1Colloid Polym. Sci. 1(1E) J. Insect Physiol. 1 Talanta 2

Colloid Surf. A-Physicochem. Eng. Asp. 1 3 J. Ind. Microbiol. Biotechnol. 1 Tetrahedron 2 2Colloid Surf. B-Biointerfaces 1 J. Lipid Res. 2 Tetrahedron Lett. 1

Comput. Theor. Chem. a 1(1ed) J. Med. Chem. 2 5 Text. Res. J. 2 2C. R. Chim. 1 J. Microencapsul. 1 Theor. Chem. Acc. 1

Curr. Med. Chem. 1 J. Mol. Liq. 1 Thermochim. Acta 1Curr. Opin. Chem. Biol. 1 J. Mol. Model. 1 Trac-Trends Anal. Chem. 3

Curr. Org. Synth. 1 J. Nat. Prod. 1 1 Water Res 1Drug Metab. Dispos. 2 J. Nutr. 1 Water Sci. Technol. 1

Eur. J. Lipid Sci. Technol. 1 J. Org. Chem. 1asee J. Mol. Struct. (since 2011); E: errata; ed: editorial

List of ISI JOURNALS in alphabetical order and number of papers/year

Arthritis Rheum. 2 Int. Rev. Biophys. Chem. 1 Pharmaceutics 1Crystals 1 J. Nucleic Acids, 4(1ed) 1 Vlakna a Textil 1

Fib. Text. East Eur. 1 Open Org. Chem. J. 1

Papers in non-ISI JOURNALS international

14


15th Fèlix Serratosa Conference (19/01/2010)Sulfur ylide epoxidations and applications in synthesisVarinder K. AggarwalUniversitat de Bristol, UK.

Amb la química es poden fer diners, ben fets?Conferences at CID “Josep Pascual Vila” (16, 23, 30/03 and 14/04/2011)Algunos aspectos determinantes en la creación de una empresaDr. José Mª García Antón. Director y fundador de Lipotec Group S.A.

El olor de la química: síntesis industrial de compuestos orgánicos para la creación de fraganciasDra. Mónica Diaz Sierra. International Flavors & Fragances, IFF

Rendibilitzar experiència i coneixement: assesorament a la indústriaDr. Octavi Colomina. Director y fundador de TDV Complience Technologies

BASF: Producción química y medio ambiente en Tarragona.Dr. Primitivo Gutiérrez-Martín. BASF

SPECIAL EVENTS

A. Messeguer Advisory Council Member, Chemistry Faculty, Universitat de Barcelona

A. Marsal Asociación Química Española de la Industria del Cuero Award

BioGLane Biotecnología de I+D+I Award (P. Clapés, J. Joglar, J. Ll. Torres founding IQACmembers)

AWARDS AND NOMINATIONS

Chemistry Celebration at CID “Josep Pascual Vila” (5/07/2011)Bioglane: del laboratori a la planta pilot, i almercat? Josep Lluís Torres Dpt. Química Biològica i Modelització Molecular

Pèptids per al tractament de la SIDA. Mª Jose Gomara Dpt. Química Biomèdica

Nous medicaments basats amb el DNA i el RNA. Montserrat Terrazas Dpt. Nanotecnología Química i Biomolecular)

Enzims, temperatura, dinàmica, estabilitat, i funció.Massa variables per treure'n l'entrellat?Ramon CrehuetDpt. Química Biològica i Modelització Molecular

La química a flor de piel. Olga López Dpt. Tecnología Química i de Tensioactius

INVITED CONFERENCES AT CBN WORKSHOPS II Workshop CBN’10 (15/10/2010)Dr. Josep Rocas. Applied Nanotechnology. From University totechnological based Industry. Example: PolymericMicro and Nanoencapsulation. Ecopol Tech S.L. (R&D Department)

Dr. Enrique Pérez-Payá. Playing with chemical biology around apoptosis. Department of Medicinal Chemistry, Centro deInvestigaciones Príncipe Felipe, Valencia

Dr. Ignacio Alfonso. Constitutional dynamic chemistry as asupramolecular approach to functionalpseudopeptidic compounds.Department of Biological Chemistry andMolecular Modelling, IQAC-CSIC

III Workshop CBN’11 (27/10/2011)Dr. Ignasi Miquel. Thrombotargets, the development ofprocoagulant nanovesicles. Thrombotargets Europe (Strategic Alliances,Director)

Dr. Nicholas Hud. DNA folding and assembly in natural and non-natural environments. Georgia Institute of Technology, USA

Dr. Amadeu Llebaria. Glycolipids and aminocyclohexanes. Department of Biomedical Chemistry, IQAC-CSIC

15


DEPARTMENT OF BIOLOGICAL CHEMISTRYAND MOLECULAR MODELLING

2


Head: Jesús Joglar Tamargo

DEPARTMENT OF BIOLOGICAL CHEMISTRY AND MOLECULAR MODELLING

19

Research interests of this Department are focused on: Molecules of biological and biomedical interest. Isolation, design, synthesis, biosynthesis,and activity evaluation of drugs, insect pheromones, secondary metabolites, enzymaticinhibitors, biocatalysts, agro-forestry by-products and antioxidants. Molecular recognition of ions and molecules of biological interest. Study of non covalent interactions. Modelling of enzymatic catalysis mechanisms. Modification of the activity and selectivity of biocatalysts by means of genetic engineering.Mechanisms of action of antioxidant protectors. Biorational control of plagues. Characterization of insect proteins by means of proteomicand molecular biology techniques. Persistent organic free radicals as biochemical sensors. Study of the electronic structure and reactivity of molecules by means of theoreticalchemistry computational techniques. Computational elucidation of reaction mechanisms ofinterest in atmospheric chemistry. New theoretical methods for exploring potential energysurfaces.

Research groups Nutraceuticals and Free Radicals Biotransformation and Bioactive Molecules Supramolecular Chemistry Ecological Chemistry Theoretical and Computational Chemistry Biologically Active Phytochemicals


20

Nutraceuticals and Free RadicalsResearch at NFR involves the preparation (extraction,synthesis) and evaluation of natural products ofplant origin or their derivatives with application asdisease preventing agents. In particular, thenutraceuticals (e.g. antioxidant polyphenols) areobtained from agricultural and forest by-productsand this gives the Lab an environmental side. Thebiological activities tested on the nutraceuticals arerelated to the control of the oxidative stress which isa major damaging process, mediated by free radicalsand occurring in many disorders (metabolicsyndrome, cardiovascular disease, type 2 diabetes,cancer, Alzheimer, Parkinson). The study of freeradicals, their reactivity, their use as probes forantioxidant activity and their control or eliminationby natural nutraceuticals is a central focus of ourresearch.

STAFFJOSEP LLUÍS TORRES SIMON, GROUP LEADER LUIS JULIÁ BARGÉSLLUÍS FAJARÍ AGUDO

Ph. D.JARA PÉREZ JIMÉNEZ

Ph. D. STUDENTSANNA CARRERAS CARDONA JUAN ANTONIO MESA DÍAZEUNICE MOLINAR TORIBIO

Publications (articles)

Synthesis of a new stable and water-solubletris(4-hydroxysulfonyltetrachlorophenyl)methylradical with selective oxidative capacity.Mesa, J.A., Velázquez-Palenzuela, A., Brillas, E.,Torres, J.L., Juliá, L.Tetrahedron 67 3119-3123, 2011An EPR analysis of β-dimerization in α-blocked pyrroles in oxidant conditions.Juliá, L., Rius, J., Torrelles, X. Magn. Reson. Chem. 49 164–167, 2011A lyophilized red grape pomace containingproanthocyanidin-rich dietary fiber inducesgenetic and metabolic alterations in colonmucosa of female C57BL/6J mice.Lizárraga, D., Vinardell, M.P., Noé, V., van Delft,J.H., Alcarraz-Vizán, G., van Breda, S.G., Staal, Y.,Günter, U.L., Reed, M.A., Ciudad, C.J., Torres,J.L., Cascante, M.J. Nutr. 141 1597-1604, 2011Role of galloylation and polymerization incytoprotective effects of polyphenolicfractions against hydrogen peroxide insult.Mitjans, M., Ugartondo, V., Martínez, V.,Touriño,S., Torres, J.L.; Vinardell, M.P.J. Agric. Food Chem. 59 2113-2119, 2011Protective effect of structurally diverse grapeprocyanidin fractions against UV-induced celldamage and death.Matito, C., Agell, N., Sánchez-Tena, S., Torres,J.L., Cascante, M.J. Agric. Food Chem. 59 4489-4495, 2011

Galloylated polyphenols as inhibitors ofhemoglobin-catalyzed lipid oxidation in fishmuscle.Iglesias, J., Pazos, M., Maestre, R., Torres, J.L.,Medina, I.J. Agric. Food Chem. 59 5684-5691, 2011Metabolites in contact with the rat digestivetract after ingestion of a phenolic-rich dietaryfiber matrix.Touriño, S., Pérez-Jiménez, J., Mateos-Martín,M.L., Fuguet, E., Vinardell, M.P., Cascante, M.,Torres, J.L. J. Agric. Food Chem. 59 5955–5963, 2011Analysis of nonextractable phenoliccompounds in foods: the current state of the art.Pérez-Jiménez, J., Torres, J.L.J. Agric. Food Chem. 59 12713-12724, 2011Stable radical cores: A key for bipolar chargetransport in glass forming carbazole andindole derivatives.Castellanos, S., Gaidelis, V., Jankauskas, V.,Grazulevicius, J.V., Brillas, E., López-Calahorra, F.,Juliá, L., Velasco, D.Chem. Commun. 46 5130-5132, 2010Differential behavior of amino-iminoconstitutional isomers in nonlinear opticalprocesses.Latorre, S., de Moreira, I.P.R., Villacampa, B., Julià,L., Velasco, D., Bofill, J.M., López-Calahorra, F. ChemPhysChem. 11 912-919, 2010


EPR/Spin-trapping study of free radicalintermediates in the photolysis oftrifluoromethyl ketones with initiators. Rosa, E., Guerrero, A., Bosch, M.P., Julià, L.Magn. Reson. Chem. 48 198–204, 2010Antioxidant activities of hydroxytyrosol mainmetabolites do not contribute to beneficialhealth effects after olive oil ingestion.Khymenets, O., Fitó, M., Touriño, S., Muñoz-Aguayo, D., Pujadas, M., Torres, J.L., Joglar, J.,Farré, M., Covas, M.I., De La Torre, R.Drug Metab. Dispos. 38 1417-1421, 2010Absorption and metabolization ofcytoprotective epicatechin thio conjugatesin rats. Selga, A., Vinardell, M.P., Martín-Venegas, R.,Jáuregui, O., Casas, J., Torres, J.L.Drug Metab. Dispos. 38 2188-2194, 2010

ZmMYB31 directly represses maize ligningenes and redirects the phenylpropanoidmetabolic flux. Fornal, Shi, X., Chai, C., Encina, A., Irar, S.,Capellades, M., Fuguet, E., Torres, J.L., Rovira, P.,Puigdomènech, P., Rigau, J., Grotewold, E., Gray,J., Caparrós-Ruiz, D.Plant J. 64 633-644, 2010Proanthocyanidin metabolites associated withdietary fibre from in vitro colonicfermentation and proanthocyanidinmetabolites in human plasma.Saura-Calixto, F., Pérez-Jiménez, J., Touriño, S.,Serrano, J., Fuguet, E., Torres, J.L., Goñi, I.Mol. Nutr. Food Res. 54 939–946, 2010Impact of thermal processing on the activityof gallotannins and condensed tannins fromhamamelis virginiana used as functionalingredients in seafood. González, M.J., Torres, J.L., Medina, I.J. Agric. Food Chem. 58 (7) 4274–4283, 2010

Research highlights Synthesis of a new stable and water-solubletris(4-hydroxysulfonyltetrachlorophenyl)methylradical with selective oxidative capacityMesa, J. A., Velázquez-Palenzuela, A., Brillas, E.,Torres, J. Ll., Juliá, L.Tetrahedron, 2011, 67, 3119-3123A new stable organic free radical of the PTM(perchlorotriphenylmethyl) series very soluble inwater was reported. This free radical is sensitive toelectron transfer processes, and the selectivity ofthese reactions in the presence of ascorbic acid,pyrogallol and catechol as reducing species isdescribed. The electron paramagnetic resonancespectrum and the electrochemical behaviour werealso reported. The new radical can be used toevaluate the scavenging activity of antioxidants inwater including the antioxidant capacity ofbiological fluids.

Evolution of the UV-vis spectra of an aqueous basic solutionof αH-TSPTM every two hours; generation of the TSPTMradical

Metabolites in contact with the rat digestivetract after ingestion of a phenolic-rich dietaryfiber matrix.Touriño, S., Pérez-Jiménez, J., Mateos-Martín,M.L., Fuguet, E., Vinardell, M.P., Cascante, M.,Torres, J.LJ. Agric. Food Chem., 2011, 59, 5955-5963By use of HPLC-ESI-MS/MS techniques phenolicmetabolites were detected in feces, cecal content,and colonic tissue from rats given grapeantioxidant dietary fiber (GADF). During theirtransit along the digestive tract, proanthocyanidinoligomers and polymers are depolymerized into ECunits. Thus, after ingestion of GADF, free EC andits conjugates, as well as free and conjugatedmicrobially derived phenolic metabolites, comeinto contact with the intestine epithelium for morethan 24 h and may be partly responsible for thepositive influence of GADF on gut health.

21


Metabolization of polymeric proanthocyanidins from GADF

22


STAFFPEDRO CLAPES SABORIT, GROUP LEADER JORGE BUJONS VILÀS GLORIA CAMINAL SAPERAS (Service CommissionUAB)JESUS JOGLAR TAMARGO

Ph. D. STUDENTSBRUNO ALMEIDA COTRIMALDA LISA CONCIA XAVIER GARRABOU PI LIVIA GÓMEZ CORTÉSMARIANA GUTIERREZ TEJEDA ARISTOTELIS KOTRONOULAS ANNA SZEKRENYIKAREL HERNANDEZ SANCHEZANNA SOLER CASAPONSARAQUEL ROLDÁN


Current trends in asymmetric synthesis withaldolases Clapés, P., Garrabou, X. Adv. Synth. Catal. 353 2263-2283, 2011Redesign of the phosphate binding site of L-rhamnulose- 1-phosphate aldolase towards adihydroxyacetone dependent aldolase. Garrabou, X., Joglar, J., Parella, T., Crehuet, R.,Bujons, J., Clapés, P. Adv. Synth. Catal. 353 89-99, 2011Structure-guided redesign of D-fructose-6-phosphate aldolase from E. coli: Remarkableactivity and selectivity towards acceptorsubstrates by two-point mutation. Gutierrez, M., Parella, T., Joglar, J., Bujons, J.,Clapés, P. Chem. Commun. 47 5762-5764, 2011Direct analysis of glucuronidated metabolitesof main olive oil phenols in human urine afterdietary consumption of virgin olive oil.Khymenets, O., Farré, M., Pujadas, M., Ortiz, E.,Joglar, J., Covas, M.I., De La Torre, R. Food Chemistry 126 306-314, 2011Triazine-based vanilloid 1 receptor openchannel blockers: Design, synthesis,evaluation, and SAR analysis.Vidal-Mosquera, M., Fernández-Carvajal, A.,Moure, A., Valente, P., Planells-Cases, R.,González-Ros, J.M., Bujons, J., Ferrer-Montiel, A.,Messeguer, A. J. Med. Chem. 54 7441-7452, 2011

Highly Efficient Aldol additions of DHA andDHAP to N-Cbz-Amino aldehydes Catalyzed byL-Rhamnulose-1-Phosphate and L-Fuculose-1-Phosphate Aldolases in Aqueous Borate Buffer.Garrabou, X., Joglar, J., Parella, T., Bujons J.,Clapés, P.Org. Biomol. Chem. 9 8430-8436, 2011Chemical modulation of peptoids: synthesisand conformational studies on partiallyconstrained derivatives.Moure, A., Sanclimens, G., Bujons, J., Masip, I.,Alvarez-Larena, A., Pérez-Payá, E., Alfonso, I.,Messeguer, A.Chem. Eur. J. 17 7927-7939, 2011New glucocerebrosidase inhibitors byexploration of chemical diversity of N-substituted aminocyclitols using clickchemistry and in situ screening.Díaz, L., Casas, J., Bujons, J., Llebaria, A.,Delgado, A. J. Med. Chem. 54 2069-2079, 2011Computational prediction of structure-Activityrelationships for the binding of aminocyclitolsto β-glucocerebrosidase.Díaz, L., Bujons, J., Delgado, A., Gutiérrez-De-Terán, H., Åqvist, J. J. Chem. Inf. Model. 51 601-611, 2011Identification of new ozonation disinfectionbyproducts of 17β-estradiol and estrone inwater.Pereira, R.D.O., de Alda, M.L., Joglar, J., Daniel,L.A., Barceló, D. Chemosphere 84 1535-1541, 2011

Biotransformation and Bioactive MoleculesCarbon-carbon bond formation lies at the core oforganic synthesis. Biocatalytic carbon-carbon bondsynthesis is an attractive methodology for theasymmetric construction of molecular frameworks,giving access to complex, multifunctional targetstructures that are difficult to prepare byconventional means. Carboligases are particularlyappropriate to generate innovative molecules andmolecular diversity accessible for investigations indrug discovery. Our research is focused on thedesign, production and evaluation of carboligationbiocatalysts and biologically active molecules. Thisincludes the redesign of aldolases by structure-guided site directed mutagenesis andcomputational models to alter their selectivitypropertie.

23


24

Recent progress in stereoselective synthesiswith aldolases.Clapés, P., Fessner, W.-D., Sprenger, G.A.,Samland, A.K. Curr. Opin. Chem. Biol. 14 154-167, 2010Redesigning the active site of transaldolaseTalB from escherichia coli: New variants withimproved affinity towardsnonphosphorylated substrates. Schneider, S., Gutiérrez, M., Sandalova, T.,Schneider, G., Clapés, P., Sprenger, G.A.,Samland, A.K. ChemBioChem 11 681-690, 2010A mutant D-fructose-6-phosphate aldolase(Ala129Ser) with improved affinity towardsdihydroxyacetone for the synthesis ofpolyhydroxylated compounds.Castillo, J.A., Guérard-Hélaine, C., Gutiérrez, M.,Garrabou, X., Sancelme, M., Schürmann, M.,Inoue, T., Hélaine, V., Charmantray, F., Gefflaut,T., Hecquet, L., Joglar, J., Clapés, P., Sprenger,G.A., Lemaire, M. Adv. Synth. Catal. 352 1039-1046, 2010Structure-guided minimalist redesign of L-fuculose-1-phosphate aldolase active site.Expedient synthesis of novelpolyhydroxylated pyrrolizidines and theirinhibitory properties against glycosidases andintestinal disaccharidases. Garrabou, X.; Gomez, L.; Joglar, J.; Gil, S.; Parella,T.; Bujons, J.; Clapés, P. Chem. Eur. J. 16, 10691-10706, 2010Cytotoxicity and enzymatic activity inhibitionin cell lines treated with novel iminosugarderivatives.Padró, M., Castillo, J.A., Gómez, l., Joglar, J.,Clapés, P., de Bolós, C.Glycoconj. J. 27 277-285, 2010

Click chemistry approach to new N-substitutedaminocyclitols as potential pharmacologicalchaperones for gaucher disease.Díaz, L., Bujons, J., Casas, J., Llebaria, A.,Delgado, A. J. Med. Chem. 53 5248-5255, 2010Matrix effects on the bioavailability ofresveratrol in humans.Ortuño, J., Covas, M.-I., Farre, M., Pujadas, M.,Fito, M., Khymenets, O., Andrés Lacueva, C.,Roset, P., Joglar, J., Lamuela Raventós, R., de laTorre, R.Food Chem. 120 1123-1130, 2010Antioxidant activities of hydroxytyrosol mainmetabolites do not contribute to beneficialhealth effects after olive oil ingestion.Khymenets, O., Fitó, M., Touriño, S., Muñoz-Aguayo, D., Pujadas, M., Torres, J.L., Joglar, J.,Farré, M., Covas, M.-I., De La Torre, R. Drug Metab. Dispos. 38 1417-1421, 2010Synthesis of fatty acid amides of catecholmetabolites that exhibit antiobesityproperties.Almeida, B., Joglar, J., Luque Rojas, M.J., Decara,J.M., Bermúdez-Silva, F.J., Macias-González, M.,Fitó, M., Romero- Cuevas, M., Farré, M., Covas,M.I., Rodríguez De Fonseca, F., De La Torre, R. ChemMedChem 5 1781-1787, 2010

Publications (books and book chapters) Enzymatic direct aldol additions.Clapés, P., Fessner, W.-D.In: Science of Synthesis. Stereoselective Synthesis2. Stereoselective Reactions of Carbonyl and IminoGroups (ed. Molander G.A). Vol 2, pp 677-734,2011Georg Thieme Verlag KG, Stuttgart (Germany)

Immobilization of PLP-dependent enzymeswith cofactor retention and enhanced stability.López, C., Ríos, S.D., López-Santín, J., Caminal,G., Álvaro G.Biochem. Eng. J. 49 414-421, 2010White-rot fungus-mediated degradation ofthe analgesic ketoprofen and identification ofintermediates by HPLC-DAD-MS and NMR.Marco-Urrea, E., Pérez-Trujillo, M., Cruz-Morató,C., Caminal, G., Vicent, T.Chemosphere 78 474-481, 2010Advanced oxidation of benzene, toluene,ethylbenzene and xylene isomers (BTEX) byTrametes versicolor.Aranda, E., Marco-Urrea, E., Caminal, G., Arias,M.E., García-Romera, I., Guillén, F. J. Hazard. Mater. 181 181-186, 2010Naproxen degradation test to monitorTrametes versicolor activity in solid-statebioremediation processes.Rodríguez-Rodríguez, C.E., Marco-Urrea, E.,Caminal, G.J. Hazard. Mater. 179 1152–1155, 2010

Degradation of the drug sodium diclofenac byTrametes versicolor pellets and identificationof some intermediates by NMR.Marco-Urrea, E., Pérez-Trujillo, M., Cruz-Morató,C., Caminal, G., Vicent, T.J. Hazard. Mater. 176 836–842, 2010Oxidation of atenolol, propranolol,carbamazepine and clofibric acid by abiological Fenton-like system mediated by thewhite-rot fungus Trametes versicolor.Marco-Urrea, E., Radjenovic, J., Caminal, G.,Petrovic, M., Vicent, T., Barceló, D.Water Res. 44 521–532, 2010Biodegradation of sulfamethazine byTrametes versicolor: Removal from sewagesludge and identification of intermediateproducts by UPLC-QqTOF-MS.García-Galán, M.J., Rodríguez-Rodríguez, C.E.,Vicent, T., Caminal, G., Díaz-Cruz, M.S., Barceló, D.Sci. Total Environ. 409 5505-5512, 2011.

Applied Biocatalysis Unit (IQAC, CSIC-UAB) Publications


Expression of metallocarboxypeptidaseinhibitors in Escherichia coli: Effect of cysteine content and protein size in thesecretory production of disulfide-bridgedproteins.Puertas, J.-M., Caminal, G., González, G.J. Ind. Microbiol. Biotechnol. 38 1553-1560, 2011. Bioremediation of PAHs-contaminated soilthrough composting: Influence ofbioaugmentation and biostimulation oncontaminant biodegradation.Sayara, T., Borràs, E., Caminal, G., Sarrà, M.,Sánchez, A.Int. Biodeterior. Biodegrad. 65 859-865, 2011.

Soil colonization by Trametes versicolorgrown on lignocellulosic materials: Substrateselection and naproxen degradation.Borràs, E., Llorens-Blanch, G., Rodríguez-Rodríguez, C.E., Sarrà, M., Caminal, G.Int. Biodeterior. Biodegrad. 65 846-852, 2011. Solid-phase treatment with the fungusTrametes versicolor substantially reducespharmaceutical concentrations and toxicityfrom sewage sludge.Rodriguez-Rodriguez, C.E., Jelic, A., Llorca, M.,Farré, M., Caminal, G., Petrovic, M., Barceló, D.,Vicent, T.Bioresour. Technol. 102 5602-5608, 2011.

Research highlights Redesign of recombinant aldolases forasymmetric carbon-carbon bond formationL-Fuculose-1-phosphate aldolase (FucA), L-rhamnulose-1-phosphate aldolase (RhuA) and D-fructose-6-phosphate aldolase (FSA) from E. coligenome are amazing powerful catalysts forasymmetric C-C bond formation. Structure guidedredesign of the active center by site-directedmutagenesis furnished a collection of novel aldoladdition catalysts with broad substrate selectivityand complementary stereochemistry. Furthermore,RhuA and FSA tolerate unphosphorylated DHAanalogues, and this simplifies the synthetic schemeavoiding the use of highly elaborated startingmaterials. Their selective catalytic properties alloworganic chemists to access easily to sugars of theketose and aldose families and their analogs,difficult to prepare by purely chemical procedures.

25



Enantiopure triazolium salts: Chemoenzymaticsynthesis and applications in organocatalysis.Ríos-Lombardía, N., Porcar, R., Busto, E., Alfonso,I., Montejo-Bernardo, J., García-Granda, S.,Gotor, V., Luis, S.V., García-Verdugo, E., Gotor-Fernández, V. ChemCatChem 3 1921-1928, 2011Stimulus responsive self-assembly of GeminiAmphiphilic Pseudopeptides.Rubio, J., Alfonso, I., Burguete, M.I., Luis, S.V. Soft Matter 7 10737-10748, 2011Crystal structure of the N-benzyloxycarbonyl-alanyl-phenylalanyl-methyl ester: theimportance of the H-bonding pattern.Alfonso, I., Bolte, M., Burguete, M.I., Luis, S.V.Crystals 1 163-170, 2011Chemical modulation of peptoids: Synthesisand conformational studies on partiallyconstrained derivatives Moure, A., Sanclimens, G., Bujons, J., Masip, I.,Alvarez-Larena, A., Pérez-Payá, E., Alfonso, I.,Messeguer, A. Chem-Eur. J. 17 7927-7939, 2011Polyhydroxylated bicyclic isoureas andguanidines are potent glucocerebrosidaseinhibitors and nanomolar enzyme activityenhancers in gaucher cells.Trapero, A., Alfonso, I., Butters, T.D., Llebaria, A. J. Am. Chem. Soc. 133 5474-5484, 2011Update 1 of: Enantioselective enzymaticdesymmetrizations in organic synthesis.García-Urdiales, E., Alfonso, I., Gotor, V. Chem. Rev. 111 PR110-PR180, 2011

Structurally disfavoured pseudopeptidicmacrocycles through anion templation.Bru, M., Alfonso, I., Bolte, M., Burguete, M.I.,Luis, S.V. Chem. Commun. 47 283-285, 2011Gemini amphiphilic pseudopeptides: Synthesisand preliminary study of their self-assemblingproperties.Rubio, J., Alfonso, I., Bru, M., Burguete, M.I.,Luis, S.V. Tetrahedron Lett. 51 5861-5867, 2010Optically active macrocyclichexaazapyridinophanes decorated at theperiphery: Synthesis and applications in theNMR enantiodiscrimination of carboxylic acids. Busto, E., González-Álvarez, A., Gotor-Fernández,V., Alfonso, I., Gotor, V. Tetrahedron 66 6070-6077, 2010Molecular recognition of N-protecteddipeptides by pseudopeptidic macrocycles: A comparative study of the supramolecularcomplexes by ESI-MS and NMR.Alfonso, I., Bolte, M., Bru, M., Burguete, M.I.,Luis, S.V., Vicent, C. Org. Biomol. Chem. 8 1329-1339, 2010Structural diversity in the self-assembly ofpseudopeptidic macrocycles.Alfonso, I., Bru, M., Isabel Burguete, M., García-Verdugo, E., Luis, S.V. Chem-Eur. J. 16 1246-1255, 2010Chiral molecular receptors based on trans-cyclohexane-1,2-diamine.Alfonso, I. Curr. Org. Synth. 7 1-23, 2010

26

Supramolecular ChemistrySupramolecular chemistry is the “chemistry beyondthe molecule” and deals with the interactionsbetween chemical species in an ordered andhierarchical way, leading to the formation of well-defined supramolecules. We mainly work in thefields of molecular recognition, programmedfolding and self-assembling processes, using a largevariety of experimental and theoretical approaches.The discovery, preparation and study of newsynthetic receptors for biologically interestingmolecules and ions (especially anions) are our mainactivities. We also use supramolecular approachesto synthetic procedures, such as templatedsynthesis, dynamic combinatorial chemistry andconstitutional dynamic chemistry. Additionally, wecollaborate with several groups (both at IQAC andoutside) to study biomolecular and biomimeticsystems from a supramolecular point of view.

STAFFIGNACIO ALFONSO RODRÍGUEZ, GROUP LEADER

Ph. D.CIRIL JIMENO MOLLETALEJANDRA MOURE FERNÁNDEZENRICO FAGGI

Ph. D. STUDENTSJOAN ATCHER UBIERGO


27

The pseudopeptidic macrocycles recently preparedin our group1 were studied for the molecularrecognition of N-protected dipeptides2 by acombination of ESI-MS and NMR techniques andwith the help of molecular modeling. Some of thereceptors displayed good selectivity for dipeptidesover the corresponding amino acids and a slightpreference for the dipeptides containing aromaticside chains. On the other hand, some of thesemacrocycles were able to self-assemble intohierarchical nanostructures rendering differentmorphologies depending on the chemicalstructures of the compound.3 Thus we observedthe formation of fibers or vesicles at themicro/nanometric scale. A deep study using abattery of techniques (SEM, TEM, ATR FT-IR,UV-CD, NMR) allowed us to understand theaggregation process, induced by a combination ofpolar (H-bonding) and nonpolar (van de Waals andπ-stacking) non-covalent interactions. The fullunderstanding of the process led us to fabricate

hybrid nanostructures rendering either spherescovered by fibrils or segregated vesicles andfibers.3 Moreover, the self-assembling capabilitiesof pseudopeptidic molecules have been exploitedone step further. We have synthesized a newfamily of Gemini Amphiphilic Pseudopeptides(GAPs) which can also aggregate into differentnanostructures (fibers, fibrils, spheres, tapes ortubes) depending on the growing conditions(solvent, pH) and the chemical structure of theGAP.4 A systematic study using a large number oftechniques allowed us to fully understand theprocess and to propose a model for theassembling mechanism.5 Moreover, the delicateinterplay between hydrophobic and hydrophilicinteractions served for the design of a newgeneration of GAPs capable to undergo stimulus-dependent morphological transitions (from fibersto vesicles) in aqueous medium, as well as to formstable supramolecular hydrogels with promisingapplications in bionanotechnology.6

Research highlights

1. (a) Alfonso, I., Bolte, M., Bru, M., Burguete, M.I., Luis, S.V. Chem.-Eur. J. 2008, 14, 8879-8891. (b) Alfonso, I., Bolte, M., Bru, M., Burguete, M.I., Luis, S.V., Rubio, J. J. Am. Chem. Soc. 2008, 130, 6137-6144

2. Alfonso, I., Bolte, M., Bru, M., Burguete, M.I., Luis, S.V., Vicent, C. Org. Biomol. Chem. 2010, 8, 1329-1339.3. Alfonso, I., Bru, M., Isabel Burguete, M., García-Verdugo, E., Luis, S.V. Chem-Eur. J. 2010, 16, 1246-1255.4. Rubio, J., Alfonso, I., Bru, M., Burguete, M.I., Luis, S.V. Tetrahedron Letters 2010, 51, 5861-5867.5. Rubio, J., Alfonso, I., Burguete, M.I., Luis, S.V. Soft Matter 2011, 7, 10737-10748.6. Rubio, J., Alfonso, I., Burguete, M.I., Luis, S.V. Chem. Commun. 2012, 48, 2210-2212.

From salts to ionic liquids by systematicstructural modifications: A rational approachtowards the efficient modular synthesis ofenantiopure imidazolium salts.Ríos-Lombardía, N., Busto, E., Gotor-Fernández,V., Gotor, V., Porcar, R., García-Verdugo, E., Luis,S.V., Alfonso, I., Garcia-Granda, S., Menéndez-Velázquez, A. Chem-Eur. J. 16 836-847, 2010


STAFFÁNGEL GUERRERO PÉREZ, GROUP LEADER Mª PILAR BOSCH VERDEROLGLORIA ROSELL PELLISÉ

TECHNICIANJUANA Mª ROZALEN MECA

Ph. D. LOURDES MUÑOZ RUBIOCARMEN QUERO LÓPEZ

Ph. D. STUDENTSBEN FURSTENAURAFAEL GAGO OTERO MARC PUIGMARTÍ BORRELLANNA RODRÍGUEZ RIVERO


Enzymatic enantiomeric resolution ofphenylethylamines structurally related toamphetamine.Muñoz, L., Rodríguez, A.M., Rosell, G., Bosch,M.P., Guerrero, A. Org. Biomol. Chem. 9 8171-8177, 2011Pheromone synthesis in a biomicroreactorcoated with anti-adsorption polyelectrolytemultilayer.Dimov, N., Muñoz, L., Carot-Sans, G., Verhoeven,M.L.P.M., Bula, W.P., Kocer, G., Guerrero, A.,Gardeniers, H.J.G.E. Biomicrofluidics 5 034102, 2011http://dx.doi.org/10.1063/1.3608138 (12 pages)Inhibition of electrophysiological response tothe pheromone of the fall armyworm,Spodoptera frugiperda.Perez Luis, C.P., Guerrero, A., Malo, E.A.J. Pest. Sci. 35 23-26, 2010Behavioural and electrophysiological responsesof the European corn borer Ostrinia nubilalis tohost-plant volatiles and related chemicals.Solé, J., Sans, A., Riba, M., Guerrero, A. Physiol. Entomol. 35 354-363, 2010Reactivity versus steric effects in fluorinatedketones as esterase inhibitors: A quantummechanical and molecular dynamics study.Rayo, J., Muñoz, L., Rosell, G., Hammock, B.D.,Guerrero, A., Luque, F.J., Pouplana, R. J. Mol. Mod. 16 1753-1764, 2010

Improved microwave-assisted ring opening of1,1,1-trifluoro-2,3-epoxypropane: Synthesis ofnew 3-alkoxy-1,1,1-trifluoropropan-2-ols.Rayó, J., Muñoz, L., Rosell, G., Bosch, M.P.,Guerrero, A. Synthesis 3117-3120, 2010Synthesis of allylic trifluoromethyl ketonesand activity as inhibitors of the sexpheromone of the leopard moth, Zeuzerapyrina L. (Lepidoptera: Cossidae).Muñoz, L., Bosch, M.P., Batllori, Ll., Rosell, G.,Bosch, D., Guerrero, A., Avilla, J.Pest Manag. Sci. 67 956-964, 2011(E)-Pityol as aggregation pheromone ofPityophthorus pubescens (Marsham)(Coleoptera: Scolytinae): Biological activity inthe laboratory and in the field.Lopez, S., Quero, C., Iturrondobeitia, J.C.,Guerrero, A., Goldarazena, A.Can. Entomol. 143 447-454, 2011Sex pheromone of the Spanish population ofthe beet armyworm Spodoptera exigua.Acín, P., Rosell, G., Guerrero, A., Quero, C. J. Chem. Ecol. 36 778-786, 2010EPR/Spin-trapping study of free radicalintermediates in the photolysis oftrifluoromethyl ketones with initiators.Rosa, E., Guerrero, A., Bosch, M.P., Julià, L. Magn. Reson. Chem. 48 198-204, 2010

28

Ecological ChemistryOur group deals with different aspects relatedwith new insect pheromones, from structuralcharacterization and synthesis of pheromones andanalogues to the establishment of the attractantactivity in the laboratory, by electrophysiologicaltechniques (EAG and GC-EAD) and behavioralbioassays, and in the field.We are also engaged in the development of newalternative and non-contaminant methods of pestcontrol, based on inhibition of the enzymesinvolved in the degradation of pheromonemolecules at the insect’s antennae.


29

The main features accomplished by the ChemicalEcology Group in the period 2010-2011 are thefollowing:

1. The pheromone composition of the Spanishpopulation of the beet armyworm (BAW),Spodoptera exigua (Lepidoptera: Noctuidae), wasidentified. Analysis of female gland extractsshowed the presence of compounds Z9,E12-14:Ac(1), Z9-14:Ac (2), Z11-16:Ac (3), Z9,E12-14:OH (4),Z9-14:OH (5) and Z11-16:OH (6) in a ratio of26:11:1:22:31:9. The amount of compound pergland ranged from 2.08 ng for 5 to 0.09 ng for 3.However, analysis of female volatiles by SPME onlyrevealed the presence of compounds, 1, 2, 3 and5 in a 34:40:4:22 ratio. In EAG assays, compound1 elicited the highest response and the C14acetates evoked higher electrophysiologicalresponses than the corresponding alcohols and theC16 isomers. GC-EAD analysis of PBAN-treatedpheromone gland extracts confirmed the presenceof compounds 1, 2, 4, 5 and 6 (see Figure 1). Inwind tunnel, no behavioral difference wasobserved between formulations based on thegland extracts and female volatiles. In both cases,males responded similarly to when virgin femaleswere used as the attractant source.

Compound 1 alone elicited upwind flight on malesbut required the presence of compound 5 in a80:20 to 40:60 ratio for full activity. Ternarymixtures of 1, 5 and the minor components did notimprove the performance of the blend 1+5 in a60:40 ratio. In the field, the mixture 1+5+3 in a56:37:7 ratio was the most attractive formulationand is expected to be useful in future pest controlstrategies (J. Chem. Ecol. 36 778-786, 2010).

Figure 1. a GC-EAD response of a Spodoptera exigua maleantenna to a PBAN-treated pheromone extract. b GC of amixture of synthetic compounds Z9,E12-14:Ac (1), Z9-14:Ac(2), Z11-16:Ac (3), Z9,E12-14:OH (4), Z9-14:OH (5), Z11-16:OH (6) (100 ng each).

2. Carboxylesterases (CEs) are a family ofubiquitous enzymes with broad substratespecificity, and their inhibition may have importantimplications in pharmaceutical and agrochemicalfields. One of the most potent inhibitors both formammalian and insect CEs are trifluoromethylketones (TFMKs), but the mechanism of action ofthese chemicals is not completely understood. Wehave examined the balance between reactivityversus steric effects in modulating the activityagainst human carboxylesterase 1. The intrinsicreactivity of the ketone moiety was determinedfrom quantum mechanical computations, whichcombined gas phase B3LYP calculations withhydration free energies estimated with the IEF/MSTmodel. In addition, docking and moleculardynamics simulations were used to explore the

Research highlights

Low-frequency sounds induce acoustic traumain cephalopods.André, M., Solé, M., Lenoir, M., Durfort, M.,Quero, C., Mas, A., Lombarte, A., Van DerSchaar, M., López-Bejar, M., Morell, M., Zaugg,S., Houégnigan, L. Front. Ecol. Environ. 9 489-493, 2011Proteomics of toxic oil syndrome in humans:Phenotype distribution in a population ofpatients.Quero, C., Colomé, N., Rodriguez, C., Eichhorn,P., Posada De La Paz, M., Gelpi, E., Abian, J. Chem-Biol. Interact. 192 129-135, 2011A diversity of putative carboxylesterases areexpressed in the antennae of the noctuidmoth Spodoptera littoralis.Durand, N., Carot-Sans, G., Chertemps, T.,Montagné, N., Jacquin-Joly, E., Debernard, S.,Maïbèche-Coisne, M.Insect Mol. Biol. 19 87-97, 2010

Characterization of an antennalcarboxylesterase from the pest mothSpodoptera littoralis degrading a host plantodorant.Durand, N., Carot-Sans, G., Chertemps, T.,Bozzolan, F., Party, V., Renou, M., Debernard, S.,Rosell, G., Maïbèche-Coisne, M. PLoS ONE 6: e29147.doi:10.1371/journal.pone.0029147, 2010

Publications (books and book chapters) Reddy, G.V.P., Guerrero, A. (2010)New Pheromones and Insect Control Strategiesin Pheromones (ed. G. Litwack). Ch 20, 493-519Vitamins and Hormones, v. 83Academic Press (Elsevier)ISBN: 978-0-12-381516-3.


30

binding mode of the inhibitors along the deepgorge that delineates the binding site. The resultspoint out that the activity largely depends on thenature of the fluorinated ketone, since the activityis modulated by the balance between the intrinsicelectrophilicity of the carbonyl carbon atom andthe ratio between keto and hydrate forms.However, the results also suggest that the correctalignment of the alkyl chain in the binding site canexert a large influence on the inhibitory activity, asthis effect seems to override the intrinsic reactivityfeatures of the fluorinated ketone.

Overall, the results sustain a subtle balancebetween reactivity and steric effects in modulatingthe inhibitory activity of TFMK inhibitors (J. Molec.Mod. 16 1753-1764, 2010).

3. Both enantiomers of several phenylethylamines4a-i, structurally related to amphetamine, have beenprepared in good yields and excellent enantiomericpurity by enzymatic kinetic resolution using CAL-Band ethyl methoxyacetate as the acyl donor (Figure2). In the case of the 4-hydroxyderivative ofamphetamine (compound 4i), the S enantiomerracemized possibly in a dynamic kinetic resolution(DKR) under the enzymatic conditions used (Org.Biomol. Chem. 9 8171-8177, 2011)

Figure 2. Enzymatic resolution of racemic amines 4a-i

4. To prepare a biosynthetic module in aninfochemical communication project, we have builta silicon-based microreactor coated with an anti-adsorption polyelectrolyte multilayer, containing animmobilized (agarose beads) alcohol acetyltransferase (atf), one of the key biosyntheticenzymes of the pheromone of Spodoptera littoralis.The system has been developed to reproducethe last step of the biosynthesis in which theprecursor diene alcohol (Z,E)-9,11-tetradecadienolis transformed into the major component of thepheromone (Z,E)-9,11-tetradecadienyl acetate(Figure 3). The microreactor has been built using apolyethylenimine/dextransulfate sodium salt-basedmultilayer as an anti-adsorption coating. Thedeposition has been implemented layer by layerand the coating has been optimized in terms ofthickness, morphology and stability at pH 9.2 and6.0 and two PEI with molecular weights 750and 1.2 kDa. Validation of the microreactorfunctionality was done by evaluation of theacetylation reaction of the diene alcohol to theacetate by gas chromatography coupled to massspectrometry (GC-MS) (Biomicrofluidics 5 034102-1-12, 2011).

Figure 3. Bioconversion catalyzed by an alcohol acetyl trans-ferase (atf). In the presence of acetyl-CoA, atf transforms(Z,E)-9,11-tetradecadienol into (Z,E)-9,11-tetradecadienylacetate, the major component of the pheromone

5. Trifluoromethyl ketones (TFMKs) structurallyrelated to the pheromones are good inhibitors ofpheromone communication in insects. To determinetheir activity on Zeuzera pyrina L. (Lepidoptera:Cossidae), a polyphagous pest, we have preparedtwo diunsaturated TFMK analogues of the majorand the minor pheromone components, and twomonounsaturated ones. The new preparedchemicals are good inhibitors of the pheromone inelectrophysiology (EAG), wind tunnel and in thefield. Our results show the importance of twounsaturations at positions 2 and 13 of thetrifluoroacyl group in the structure of the analogues,the latter being critical for the inhibitory activity. (PestManage. Sci. 67 956-964, 2011). In Figure 4 it isshown the disrupting effect exerted by (E,Z)-3,13-octadecadienyl trifluoromethyl ketone on malesflying to a virgin female. The ketone was placed ina filter paper 1 cm from the calling female.

Figure 4. Track flights of Zeuzera pyrina males towards acalling female (A and C) and a calling female in the presen-ce of (E,Z)-3,13-octadecadienyl trifluoromethyl ketone at 0.1µg (B) and 1 µg (D). The insect moved upwind from left toright. The insect position at 0.4 s intervals is shown by thedark points.



Water effects on atmospheric reactions. Buszek, R.J., Francisco, J.S., Anglada. J.M.Int. Rev. Phys. Chem. 30 335–369, 2011A new approach to local hardness.Gál, T., Geerlings, P., De Proft F., Torrent-Sucarrat,M.Phys. Chem. Chem. Phys. 13 15003-15015, 2011Redesign of the phosphate binding site of L-rhamnulose- 1-phosphate aldolase towards adihydroxyacetone dependent aldolase.Garrabou, X., Joglar, J., Parella, T., Crehuet, R.,Bujons, J., Clapés, P. Adv. Synth. Catal. 353 89-99, 2011Effect of the substituents on the reactivity ofcarbonyl oxides. A theoretical study on thereaction of substituted carbonyl oxides withwater. Anglada, J.M., González, J., Torrent-Sucarrat, M.Phys. Chem. Chem. Phys. 13 13034-13045, 2011Changes in dynamics upon oligomerizationregulate substrate binding and allostery inamino acid kinase family members.Marcos, M., Crehuet, R., Bahar I. PLoS Comput. Biol. 7 e1002201, 2011doi:10.1371/journal.pcbi.1002201Structure, stability and dynamics of hydrogenpolyoxides.Martins-Costa, M., Anglada, J.M., Ruiz-Lopez,M.F. Int. J. Quantum Chem. 111 1543-1554, 2011Crowding induces differences in the diffusionof thermophilic and mesophilic proteins: Anew look at neutron scattering results. Marcos, E., Mestres, P., Crehuet, R.Biophys. J. 101 2782-2789, 2011

The reaction between HO and (H2O)n (n 5 1,3) clusters: reaction mechanisms andtunneling effects.González, J., Caballero, M., Aguilar-Mogas, A.,Torrent-Sucarrat, M., Crehuet, R., Solé, A.,Giménez, X., Olivella, S., Bofill, J.M., Anglada, J.M. Theor. Chem. Acc. 128 579-592, 2011Protonation of water clusters induced by thehydroperoxyl radical surface.Torrent-Sucarrat, M., Ruiz-López, M.F., Martins-Costa, M., Francisco, J.S., Anglada, J.M.Chem.-Eur. J. 17 5076-5085, 2011The Impact of water on the OH + HOClreaction. González, J., Anglada, J.M., Buszek, R.J.,Francisco, J.S.J. Am. Chem. Soc. 133 3345-3353, 2011Evaluation of the nonlinear optical propertiesfor annulenes with Hückel and Möbiustopologies.Torrent-Sucarrat, M., Anglada, J.M., Luis, J.M. J. Chem. Theor. Comput. 7 3935-3943, 2011The gas phase reaction of carbonyl oxide withhydroxyl radical in presence of water vapor. Atheoretical study on the reaction mechanism Mansergas, A., González, J., Ruiz-López, M.,Anglada, J.M. Comput. Theor. Chem. 965 313-320, 2011Anharmonicity and the Eigen-Zundel dilemmain the IR spectrum of the protonated 21 watercluster.Torrent-Sucarrat, M., Anglada, J.M. J. Chem. Theory Comput. 7 467-472, 2011On the dissociation of ground state trans-HOOO radical: A theoretical study.Anglada, J.M., Olivella, S., Solé, A. J. Chem. Theory Comput. 6 2743-2750, 2010

Theoretical and Computational ChemistryThe Theoretical and Computational ChemistryGroup (QTC) studies the structure and reactivity ofmolecules using the computational methods ofTheoretical Chemistry. Special interest is devoted totwo main areas: first, the investigation of oxidationreactions playing an important role in atmosphericand environmental chemistry, as well as inbiological systems; second, the study of enzymecatalysis, with special interest in the role of proteindynamics in the catalytic cycle.

STAFFJOSEP M. ANGLADA RULL, GROUP LEADERSANTIAGO OLIVELLA NELLORAMON CREHUET SIMON

Ph. D. JAVIER GONZÁLEZ AGUILARMIQUEL TORRENT-SUCARRAT

Ph. D. STUDENTSENRIQUE MARCOS BENTEOMELCHOR SÁNCHEZ MARTÍNEZ

31


Gas phase reaction of nitric acid withhydroxyl radical without and with water. A theoretical investigation Gonzalez, J., Anglada, J.M. J. Phys. Chem. A 114 9151-9162, 2010Pentacoordinated phosphorus revisited byhigh-level QM/MM calculations Marcos, E., Field, M.J., Crehuet, R. Proteins 78 2405-2411, 2010The reactions of SO3 with HO2 radical andH2O…HO2 radical complex. Theoretical studyon the atmospheric formation of HSO5 andH2SO4Gonzalez, J., Torrent-Sucarrat, M., Anglada, J.M. Phys. Chem. Chem. Phys. 12 2116-2125, 2010On the applicability of local softness andhardness Torrent-Sucarrat, M., De Proft, F., Ayers, P.W.,Geerlings, P. Phys. Chem. Chem. Phys. 12 1072-1080, 2010

On the conservation of the slowconformational dynamics within the aminoacid kinase family: NAGK the paradigm Marcos, E., Crehuet, R., Bahar, I. Plos Comput. Biol. 6 e1000738, 2010. doi: 10.1371/journal.pcbi.1000738O2 activation and selective phenolate orthohydroxylation by an unsymmetric dicopperμη1: η1-peroxido complex Garcia-Bosch, I., Company, A., Frisch, J.R.,Torrent-Sucarrat, M., Cardellach, M., Gamba, I.,Güell, M., Casella, L., Que Jr., L., Luis, J.M.,Costas, M. Angew. Chem. Int. Edit. 49 2406-2409, 2010The bipyridyl derivatives as photomemorydevices. A comparative electronic-structurestudy.Ortiz-Sáhez, J.M., Gelabert, R., Moreno, M., LluchJ., Anglada, J.M., Bofill J.M.Chem.-Eur. J. 16 6693-6703, 2010

32

The hydrotrioxyl radical (HOOO•) plays a crucial rolein atmospheric processes involving the hydroxylradical (HO•) and molecular oxygen (O2). The figureshows two potential energy profiles for dissociationof trans-HOOO• (X 2A’’) to HO• (X 2Π) + O2(X 3Σg

–) calculated at two different CASPT2 levelsalong the r(ObOc) coordinate. CASPT2(19,15)calculations predict for trans-HOOO• (X 2A’’) acentral O−O bond length of 1.682 Å, which is inexcellent agreement with the experimental value of1.688 Å (Science 2005, 308, 1885), and give adissociation energy at 0 K D0 = 3.0 kcal/mol. Thisvalue of D0 is in excellent agreement with the recentexperimentally determined D0 = 2.9 ± 0.1 kcal/molby Le Picard et al. (Science 2010, 328, 1258).

Josep M. Anglada, Santiago Olivella, and Albert Solé, J. Chem. Theory Comput. 2010, 6, 2743-2750

Understanding the hydrated proton is ofparamount importance for the knowledge offundamental processes in chemistry and biology,and the investigation of protonated water clustershas been proven to be essential for understandingthe nature of protons in solution. The computedanharmonic IR spectra of protonated water clustersshow that the Eigen signature covers a wide rangeof frequencies. In the case of the magic numbercluster these signatures are predicted to appearclose to 2000 cm-1.Miquel Torrent-Sucarrat, and Josep M. Anglada J. Chem. Theory Comput. 2011, 7, 467–472

Research highlights


33

Species having Möbius and Hückel topologies havepromising applications in the manufacture ofHückel-to-Möbius topological optical switcheswith high nonlinear optical properties. We haveevaluated the electronic and vibrationalcontributions to static and dynamic nonlinearoptical properties of the CS Hückel and C2 Möbiustopologies synthesized by Herges and co-workers(Ajami, D. et al. Nature 2003, 426, 819).Miquel Torrent-Sucarrat, Josep M. Anglada, andJosep M. Luis J. Chem. Theory Comput. 2011, 7, 3934–3943

Enzymes catalysing phosphoryl transfer reactions areextremely efficient and are involved in crucialbiochemical processes. The reaction can proceedthrough a pentacoordinated phosphorus species thatis either a stable intermediate or a transition state.Because of this, the first X-ray structure of apentacoordinated phosphorus intermediate in thebeta-phosphoglucomutase enzyme aroused greatinterest when published in Science. To provide newinsights into the nature of that structure, wedetermined the reaction path of the phosphorylation

step using high-level QM/MM calculations. Weconclude that the pentacoordinated phosphorusformed in this enzyme is not a stable species but atransition state. We have confirmed the idea of someauthors that questioned the presence of thepentacoordinated phosphorus in the crystal andproposed the presence of a MgF3- salt as a transitionstate analogue. Marcos, E.; Field, M. J.; Crehuet, R. Proteins 2010, 78, 2405-2411.

The dynamical basis underlying the increasedthermal stability of thermophilic proteins remainsuncertain. We have challenged the new paradigmestablished by neutron scattering experiments insolution, in which the adaptation of thermophilicproteins to high temperatures lies in the lowersensitivity of their flexibility to temperaturechanges.By means of multi-scale simulations we reported areinterpretation of those experiments and showedevidence that under crowding conditions,thermophilic and homologue mesophilic proteinshave diffusional properties with different thermalbehavior. The more intense electrostatic potentialat the surface of the thermophilic protein entailsstronger electrostatic inter-protein interactions insolution that affect the diffusional behavior. Thiswork opens up opportunities to further studies toascertain whether this is a general trend and, if so,which biological implications might have.Marcos, E.; Mestres, P.; Crehuet, R. Biophys. J. 2011, 101, 2782-2789.


Water vapor is one of the most important speciesin the Erath atmosphere. It plays and important roleas a greenhouse gas but it has also a verysignificant impact on the processes that occur inthe Earth’s atmosphere. Because of its ability to beboth a hydrogen bond donor and acceptor, it canform very stable complexes. The formation of thesecomplexes can dramatically affect the chemistry inthe atmosphere, including heterogeneous removaland alteration of the photochemical properties ofthe atmospheric species, the formation of waterdroplets and aerosol particles, as well as theparticipation of these complexes in chemicalreactions. Along eight different publications wehave investigated different effects that water vaporplay in atmospheric reactions.Robert J. Buszek, Joseph S. Francisco, and Josep M.Anglada, Int. Rev. Phys. Chem., 2011, 30, 335-369

34



neo-Clerodane diterpenoids from AjugabracteosaCastro, A., Coll, J., Arfan, M. J. Nat. Prod. 74 1036-1041, 2011Phytotoxic activity of flavonoids fromDicranostyles ampla.Castro, A., Cantrell, C.L., Hale, A.L., Duke, S.O. Nat. Prod. Commun. 5 1233-1237, 2010

LC-MS-SPE-NMR for the isolation andcharacterization of neo-clerodanediterpenoids from Teucrium luteum subsp.flavovirens.Castro, A., Moco, S., Coll, J., Vervoort, J. J. Nat. Prod. 73 962-965, 2010

Biologically Active PhytochemicalsThe BAP research group has a long-standing interestin the structural elucidation of new naturalcompounds of plant origin (sesquiterpenoids relatedto insect juvenile hormones and the associatedchromene antagonists or precocenes; diterpenes asinsect anti-feedants; insect molting hormoneagonist or antagonist steroids or ecdysteroids) andtheir biological activities. Other research has involved rotenoids,furanocoumarins, iridoid glycosides, anthraquinones,bibenzyls, sterols…Nowadays, the main goals are the prospectivedevelopment of new eco-friendly and sustainableinsect pest-control agents from plants and toprovide basic knowledge for new applications,safety and quality-control procedures for othersecondary metabolites components of aromatic andmedicinal plants.

STAFFJOSEP COLL TOLEDANO

TECHNICIANJOAN LLORIA TOLRÀ

Ph. D. STUDENTSAMAYA CASTRO RUIZ

A different set of neo-clerodane diterpenoids wereisolated depending on the isolation procedureused, owing to the labile nature of tetrahydro-furofuran metabolites. From a dichloromethaneextract of Ajuga bracteosa both clerodin- anddihydroclerodin-type diterpenes were obtainedunder “hydroxyl-free” purification conditions [fournew compounds, ajubractins A-D (1-4), along withthe known 5-11].

Otherwise, when methanol-water mixtures wereused for reversed-phase prepurification andsemipreparative HPLC isolation, the new ajubractin E(12) was also isolated along with 3 and 8-11, but 7was the only tetrahydrofurofuran derivative obtained.

Epimeric (15R and 15S) mixtures of 14-hydro-15-hydroxyclerodin derivatives [15-hydroxyajubractin C(13), 14-hydro-15-hydroxyajugachin A (14), and 14-hydro-15-hydroxyajugapitin (15)], were obtainedinstead, along with 15-epi-lupulin B (16).

In addition to the importance of the isolationprocedure highlighted above, the isolation andcharacterization of small amounts of moleculesdifficult to monitor due to their nonspecific UV/visabsorption, such as the neo-clerodane diterpenesof plant origin, was reported for the first time fromTeucrium luteum subsp. flavovirens by applicationof the LC-MS-SPE-NMR technique. Three new neo-clerodane diterpenes, 3β-hydroxyteucroxylepin (1)and teuluteumin A (2) and teuluteumin B (3), werereported.

Research highlights

35


DEPARTMENT OF BIOMEDICINAL CHEMISTRY

3


The Department of Biomedicinal Chemistry conducts multidisciplinary research focused onthe biomedical applications of peptides, lipids and glycoconjugates. The early detection,markers discovery and treatment of serious human diseases, such as amyloidosis related tothe protein transthyretin, chronic pain, sphingolipidosis, cancer, neurodegeneration,autoimmune and infectious diseases, are emphasized. The investigations encompass therational design of active molecules (peptides, glycoconjugates and small molecular entities)based on the knowledge of specific cell signalling routes, metabolic pathways, mechanismsof ligand-protein interactions, etc., as well as the concept of chemical modulation foroptimising hit compounds based upon the modern medicinal chemistry technologies(combinatorial chemistry, in silico design and screening, solid phase organic synthesis,delivery systems).

Research groups Research Unit on BioActive Molecules Synthesis and Biomedical Applications of Peptides Unit of Glycoconjugate Chemistry

Head: Gemma Fabriàs Domingo

DEPARTMENT OF BIOMEDICINAL CHEMISTRY

39


The Research Unit on BioActive Molecules workson the discovery of small molecules with activity onbiologically relevant processes, with special intereston sphingolipid metabolism and functions.Sphingolipids play essential roles in the outcomeand progression of diseases, including both rarediseases (sphingolipidosis) and diseases of highsocio-economic impact (cancer, infectious diseases,diabetes 2, neurodegenerative diseases, etc.)thereby providing attractive targets to developtools of use in diagnosis and prognosis, and leadsin drug discovery. The research conductedencompasses from the design and synthesis ofmolecules and libraries to their biological study incell lines, including sphingolipidomics.

STAFFGEMMA FABRIAS DOMINGO, GROUP LEADERJOSE LUIS ABAD SAIZ JOSEFINA CASAS BRUGULAT ANTONIO DELGADO CIRILO AMADEU LLEBARIA SOLDEVILA, GROUP LEADER

TECHNICIANSEVA DALMAU ALSINA NURIA GUILLEMPEDRO RAYO PIZARROSO

Ph. D.MERITXELL EGIDO GABAS PATRICIA GONZÁLEZ BULNESYUSSEF HARRAKCARMEN BEDIA GIRBÉS

Ph. D. STUDENTSANNA ALCAIDE LÓPEZLUZ CAMACHO CASTILLOLUCÍA DÍAZ BUENOMARIA GARRIDO MARTÍNEZJOSÉ M. MUÑOZ OLAYAFABIO SIMBARIANA TRAPERO PUIGFRANCESCA CINGOLANIINGRID NIEVES CALATRAVAXAVIER GÓMEZ SANTACANA


Click chemistry approach to new N-substitutedaminocyclitols as potential pharmacologicalchaperones for gaucher disease.Diaz, L., Bujons, J., Casas, J., Llebaria, A.,Delgado, A.J. Med. Chem. 53 5248-5255, 20102-Aminohydroxamic acid derivatives asinhibitors of Bacillus cereusphosphatidylcholine preferred phospholipaseC PC-PLC(Bc).González-Bulnes, P., González-Roura, A., Canals,D., Delgado, A., Casas, J., Llebaria, A.Bioorg. Med. Chem. 18 8549-8555, 2010An unexpected access to a new sphingoidbase containing a vinyl sulfide unit.Nieves, I., Garrido, M., Abad, J. L., Delgado, A.Synlett 2950-2952, 2010Absorption and metabolization ofcytoprotective epicatechin thio conjugates inrats.Selga, A., Vinardell, M. P., Martin-Venegas, R.,Jauregui, O., Casas, J., Torres, J.L.Drug Metab. Dispos. 38 2188-2194, 2010Control of metabolism and signaling of simplebioactive sphingolipids: Implications in disease Gangoiti, P., Camacho, L., Arana, L., Ouro, A.,Granado, M.H., Brizuela, L., Casas, J., Fabriás, G.,Abad, J.L., Delgado, A., Gómez-Muñoz, A. Prog. Lipid Res. 49 316-334, 2010

Dihydrosphingomyelin impairs HIV-1 infectionby rigidifying liquid-ordered membranedomains.Vieira, C.R., Munoz-Olaya, J.M., Sot, J., Jiménez-Baranda, S., Izquierdo-Useros, N., Abad, J.L.,Apellániz, B., Delgado, R., Martínez-Picado, J.,Alonso, A., Casas, J., Nieva, J.L., Fabriás, G.,Mañes, S., Goñi, F.M. Chem. Biol. 17 766-775, 2010A simple fluorogenic method fordetermination of acid ceramidase activity anddiagnosis of Farber disease.Bedia, C., Camacho, L., Abad, J.L., Fabriàs, G.,Levade, T. J. Lipid Res. 51 3542-3547, 2010Glucosylceramide synthesis inhibition affectscell cycle progression, membrane trafficking,and stage differentiation in Giardia lamblia.Štefanic, S., Spycher, C., Morf, L., Fabriàs, G.,Casas, J., Schraner, E., Wild, P., Hehl, A.B., Sonda,S. J. Lipid Res. 51 2527-2545, 2010Ceramidases in hematological malignancies:Senseless or neglected target? Fabriàs, G., Bedia, C., Casas, J., Abad, J.L.,Delgado, A. Anti-Cancer Agents Med. Chem. 11 830-843,2011

Research Unit on BioActive Molecules

40


41

Acid ceramidase expression modulates thesensitivity of A375 melanoma cells to dacarbazine.Bedia, C., Casas, J., Andrieu-Abadie, N., Fabriàs,G., Levade, T. J. Biol. Chem. 286 28200-28209, 2011Inhibition of acid ceramidase by a 2-substituted aminoethanol amidesynergistically sensitizes prostate cancer cellsto N-(4-hydroxyphenyl) retinamide.Gouazé-Andersson, V., Flowers, M., Karimi, R.,Fabriás, G., Delgado, A., Casas, J., Cabot, M.C. Prostate 71 1064-1073, 2011Synthesis of antimitotic thioglycosides: invitro and in vivo evaluation of theiranticancer activity.Garcia-Alvarez, I., Groult, H., Casas, J., Barreda-Manso, M.A., Yanguas-Casas, N., Nieto-Sampedro, M., Romero-Ramirez, L., Fernández-Mayoralas, A.J. Med. Chem. 54, 6949-6955, 2011Computational prediction of structure-activityrelationships for the binding of aminocyclitolsto beta-glucocerebrosidase. Díaz, L., Bujons, J., Delgado, A., Gutiérrez-de-Teran, H., Aqvist, J. J. Chem. Inf. Model. 51 601-611, 2011Galacto-configured aminocyclitolphytoceramides are potent in vivo invariantnatural killer T cell stimulators.Harrak, Y., Barra, C.M., Delgado, A., Castano, A.R., Llebaria, A. J. Am. Chem. Soc. 133 12079-12084, 2011New glucocerebrosidase inhibitors byexploration of chemical diversity of N-substituted aminocyclitols using clickchemistry and in situ screening.Diaz, L., Casas, J., Bujons, J., Llebaria, A.,Delgado, A.J. Med. Chem. 54 2069-2079, 2011Synthesis and evaluation of xylopyranosidederivatives as "decoy acceptors" of humanbeta-1,4-galactosyltransferase 7.García-García, J. F., Corrales, G., Casas, J.,Fernández-Mayoralas, A., García-Junceda, E.Mol. Biosyst. 7 1312-1321, 2011Lipid and ganglioside alterations in tumorcells treated with antimitotic oleyl glycoside. García-Álvarez, I., Egido-Gabas, M., Romero-Ramírez, L., Doncel-Pérez, E., Nieto-Sampedro,M., Casas, J., Fernández-Mayoralas, A.Mol. Biosyst. 7 129-138, 2011Synthesis of antimitotic thioglycosides: invitro and in vivo evaluation of theiranticancer activity.García-Álvarez, I., Groult, H., Casas, J., Barreda-Manso, M.A., Yanguas-Casas, N., Nieto-Sampedro, M., Romero-Ramírez, L., Fernández-Mayoralas, A. J. Med. Chem. 54, 6949-6955, 2011Regulation of autophagy by sphingolipids.Bedia, C., Levade, T., Codogno, P.Anti-Cancer Agents Med. Chem. 11 844-853, 2011

A phospholipid analog with potentantimalarial activity, inhibits Plasmodiumfalciparum CTP:phosphocholinecytidylyltransferase activity.González-Bulnes, P., Bobenchik, A.M.,Augagneur, Y., Cerdan, R., Vial, H.J., Llebaria, A.,Ben Mamoun, C. J. Biol. Chem. 286 28940-28947, 2011Bicyclic (galacto)nojirimycin analogues asglycosidase inhibitors: effect of structuralmodifications in their pharmacologicalchaperone potential towards β-glucocerebrosidase.Aguilar-Moncayo, M., García-Moreno, M.I.,Trapero, A., Egido-Gabás, M., Llebaria, A.,Fernández, J.M., Mellet, C.O. Org. Biomol. Chem. 3698-3713, 2011Polyhydroxylated bicyclic isoureas andguanidines are potent glucocerebrosidaseinhibitors and nanomolar enzyme activityenhancers in Gaucher cells.Trapero, A., Alfonso, I., Butters, T.D., Llebaria, A.J. Am. Chem. Soc. 133 5474-5484, 2011Integrated synthetic, pharmacological, andcomputational investigation of cis-2-(3,5-dichlorophenylcarbamoyl)cyclohexanecarboxylic acid enantiomers aspositive allosteric modulators of metabotropicglutamate receptor subtype 4. Christov, C., González-Bulnes, P., Malhaire, F.,Karabencheva, T., Goudet, C., Pin, J.P., Llebaria,A., Giraldo, J.ChemMedChem. 6 131-140, 2011A novel mechanism of lysosomal acidsphingomyelinase maturation: requirementfor carboxyl-terminal proteolytic processing. Jenkins, R.W., Idkowiak-Baldys, J., Simbari, F.,Canals, D., Roddy, P., Riner, C.D., Clarke, C.J.,Hannun, Y.A. J. Biol. Chem. 286 3777-3788, 2011Regulation of CC ligand 5/RANTES by acidsphingomyelinase and acid ceramidase. Jenkins, R.W., Clarke, C.J., Canals, D., Snider,A.J., Gault, C.R., Heffernan-Stroud, L., Wu, B.X.,Simbari, F., Roddy, P., Kitatani, K., Obeid, L.M.,Hannun, Y.A.J. Biol. Chem. 286 13292-13303. 2011Syntaxin 4 is required for acidsphingomyelinase activity and apoptoticfunction.Perrotta, C., Bizzozero, L., Cazzato, D., Morlacchi,S., Assi, E., Simbari, F., Zhang, Y., Gulbins, E.,Bassi, M.T., Rosa, P., Clementi, E.J. Biol. Chem. 285 40240-40251, 2010Regulated secretion of acid sphingomyelinase:Implications for selectivity of ceramideformation.Jenkins, R.W., Canals, D., Idkowiak-Baldys, J.,Simbari, F., Roddy, P., Perry, D.M., Kitatani, K.,Luberto, C., Hannun, Y.A.J. Biol. Chem. 285 35706-35718, 2010


The myo-1,2-diaminocyclitol scaffold definespotent glucocerebrosidase activators andpromising pharmacological chaperones forGaucher disease.Trapero, A., Llebaria, A.ACS Med. Chem. Lett. 2 614–619, 2011Medicinal chemistry of aminocyclitols Díaz, L., Delgado, A.Curr. Med. Chem. 17 2393-2418, 2010

Bioassays of compounds with potentialjuvenoid activity on Drosophila melanogaster:Juvenile hormone III, bisepoxide juvenilehormone III and methyl farnesoates.Harshman, L.G., Song, K.-D., Casas, J.,Schuurmans, A., Kuwano, E., Kachman, S.D.,Riddiford, L.M., Hammock, B.D.J. Insect Physiol. 56 1465-1470, 2010

Research highlights DIHYDROCERAMIDE DESATURASE AS THERAPEUTIC TARGETIN HIV-1 INFECTION. The lateral organization of lipidsin cell membranes is thought to regulate numerouscell processes. Most studies focus on the coexistenceof two fluid phases, the liquid crystalline (l(d)) andthe liquid-ordered (l(o)), the putative presence of geldomains (s(o)) is not usually taken into account. Inour article in Chem. Biol. 17 766-775, 2010, weshow that in phospholipid:sphingolipid: cholesterolmixtures, in which sphingomyelin promoted fluid l(o)domains, dihydrosphingomyelin tended to formrigid domains. Genetic and pharmacologicalblockade of the dihydroceramide desaturase, whichreplaced sphingomyelin with dihydrosphingomyelinin cultured cells, inhibited cell infection byreplication-competent and -deficient HIV-1.Increased dihydrosphingomyelin levels gave rise tomore rigid membranes, resistant to the insertion ofthe gp41 fusion peptide, thus inhibiting viral-cellmembrane fusion. These results clarify the functionof dihydrosphingolipids in biological membranesand identify dihydroceramide desaturase as apotential target in HIV-1 infection.

AMINOCYCLITOLSPHARMACOLOGICAL CHAPERONES IN GAUCHER DISEASE. Different libraries containing the aminoaminocyclitolcore have been synthesized and tested againstglucocerebrosidase, the defective enzyme inGaucher disease, with the aim of identifyingpharmacological chaperones of further therapeuticusefulness.In some of the libraries, the aminocyclitol N-alkylsubstituent contains a triazole unit, derived fromclick chemistry reaction between a series of azidesand several N propargylaminocyclitols. Some ofthe library members have shown biochemicaldata similar or superior to those reported forN-nonyldeoxinojirimicyn, the reference compound.Structure-activity relationship studies data revealeda determinant effect of the location of the triazolering along the N-alkyl chain on the biologicalactivity observed. Furthermore, computationaldocking models indicate a correlation betweenlipophilicity and enzyme inhibition and suggest"extended" and "bent" potential binding modesfor the compounds. In the "bent" mode, the mostactive compounds could establish a hydrogen-bond interaction between the triazole moiety andenzyme residue Q284. Such an interaction wouldbe precluded in compounds with a longer spacerbetween the triazole and the aminocyclitol core.

On the other hand, four diastereomeric series ofN-alkylated [6+5] bicyclic isoureas having hydroxylsubstituents mimicking glucose hydroxyl groupshave been synthesized. One of the series ofisoureas exhibited strong inhibition of recombinantglucocerebrosidase activity with Ki values in the 2-42nM range. Furthermore, the [6+5] bicyclic guanidinederivatives with a substitution pattern analogous tothe most active isoureas were also found to be potentinhibitors of glucocerebrosidase with Ki valuesbetween 3 and 10 nM. Interestingly, the activebicyclic isoureas and guanidines also behaved asglucocerebrosidase inhibitors in wild-type humanfibroblasts at nanomolar concentrations. Importantly,some of the compounds exhibited the capacity ofincreasing glucocerebrosidase activity in Gaucherdisease lymphoblasts derived from N370S and L444Pvariants. These results describe a promising series ofpotent glucocerebrosidase ligands having the cellularproperties required for pharmacological chaperones.

IMMUNOMODULATORY AGENTS. A new class ofα-galactosylceramide (αGC) nonglycosidicanalogues bearing galacto-configured aminocyclitolsas sugar surrogates have been obtained. NaturalKiller T (NKT) cellular assays have resulted in theidentification of an active compound able to promoteNKT cell expansion in vitro in a similar fashion butmore weakly than αGC. These compounds havebeen described in a paper (J.Am.Chem.Soc. 2011,133, 5474-84) showing that produce stimulation ofthe release of Interferon-γ (IFNγ) and Interleukin-4 (IL-4) in Invariant Natural Killer T (iNKT) cell culture butwith lower potency than αGC. The activation of iNKTcells by this compound has been confirmed in flowcytometry experiments. Remarkably, when tested inmice, this compound selectively induced a verystrong production of IFN-γ indicative of a potent Th1cytokine profile. Overall, these data confirm theagonist activity of αGC lipid analogues havingcharged amino-substituted polar heads and theircapacity to modulate the response arising from iNKTcell activation in vivo. This discovery has beenabstracted in SCIBx (SciBx, July 28 2011, vol 4, issue29) outlining the potential of galactoaminocyclitolsas vaccine adjuvants. SciBx is a Nature group weeklyjournal providing analysis of the scientific contentand commercial potential of the most importanttranslational research papers from across the lifescience literature. SciBx selects weekly the 25published papers of basic life sciences with higherpotential for commercial exploitation.

42



Effect of synthetic peptides belonging to E2envelope protein of GB virus C on humanimmunodeficiency virus type 1 infection.Herrera, E., Tenckhoff, S., Gómara, M.J., Galatola,R., Bleda, M.J., Gil, C., Ercilla, G., Gatell, J.M.,Tillmann, H.L., Haro, I. J. Med. Chem. 53 6054-6063, 2010A langmuir monolayer study of theinteraction of E1(145-162) hepatitis G viruspeptide with phospholipid membranes.Sánchez-Martin, M.J., Haro, I., Alsina, M.A.,Busquets, M.A., Pujol, M. J. Phys. Chem. B 114 448-456, 2010Assessment of synthetic chimeric multipleantigenic peptides for diagnosis of GB virus Cinfection.Gómara, M.J., Fernández, L., Pérez, T., Ercilla, G.,Haro, I. Anal. Biochem. 396 51-58, 2010Effects of smoking on disease activity andradiographic progression in early rheumatoidarthritis.Ruiz-Esquide, V., Gómez-Puerta, J.A., Cañete,J.D., Graell, E., Vazquez, I., Ercilla, M.G., Viñas,O., Gómez-Centeno, A., Haro, I., Sanmartí, R. J. Rheumatol. 38 2536-2539, 2011The use of chimeric vimentin citrullinatedpeptides for the diagnosis of rheumatoidarthritis.Malakoutikhah, M., Gómara, M.J., Gómez-Puerta, J.A., Sanmartí, R., Haro, I. J. Med. Chem. 54 7486-7492, 2011

Biophysical investigations of GBV-C E1peptides as potential inhibitors of HIV-1fusion peptide.Sánchez-Martín, M.J., Urbán, P., Pujol, M., Haro,I., Alsina, M.A., Busquets, M.A. ChemPhysChem 12 2816-2822, 2011Carbon nanotube composite peptide-basedbiosensors as putative diagnostic tools forrheumatoid arthritis.de Gracia Villa, M., Jiménez-Jorquera, C., Haro, I.,Gomara, M.J., Sanmartí, R., Fernández-Sánchez,C., Mendoza, E. Biosens. Bioelectron. 27 113-118, 2011Effect of E1(64-81) hepatitis G peptide on thein vitro interaction of HIV-1 fusion peptidewith membrane models.Sánchez-Martín, M.J., Busquets, M.A., Girona, V.,Haro, I., Alsina, M.A., Pujol, M. BBA-Biomembranes 1808 2178-2188, 2011Diagnostic value of anti-GBV-C antibodies inHIV-infected patients.Gómara, M.J., Fernández, L., Pérez, T., Tenckhoff,S., Casanovas, A., Tillmann, H.L., Haro, I. Chem. Biol. Drug Des. 78 277-282, 2011Analysis of HIV-1 fusion peptide inhibition by synthetic peptides from E1 protein of GBvirus C.Sánchez-Martín, M.J., Hristova, K., Pujol, M.,Gómara, M.J., Haro, I., Alsina, Mª A., Busquets,M.A. J. Colloid Interf. Sci. 360 124-131, 2011

Synthesis and Biomedical Applications of PeptidesThe Unit of Synthesis and Biomedical Applicationsof Peptides (USiBAP) interests focus on peptidechemistry from three different points of view:design, synthesis and therapeutic value of peptidemolecules. The overall objectives of the USiBAPresearch summed up in the use of syntheticpeptides in the field of Biomedicine both inimproving diagnosis systems and in the design ofnew therapeutic targets. More specifically, work isbeing carried out on the design ofimmunopeptides, on the use of peptides for thedevelopment of new biosensors for the diagnosisof human illnesses and on the selection oftherapeutic agents of peptide origin throughbiophysical testing.

STAFFISABEL HARO VILLAR, GROUP LEADERMARÍA JOSÉ GOMARA ELENA

TECHNICIANSMARÍA JOSÉ BLEDA HERNÁNDEZ ANNA PAUSMARTA PITETRAYMOND ULLDEMOLINS

Ph. D.MORTEZA MALAKOUTIKHAH OLOUNABADI

Ph. D. STUDENTSLETICIA FERNÁNDEZ ARAUZO RAMONA GALATOLA ELENA HERRERA CARRILLO MARÍA JESÚS SÁNCHEZAIMEE VASCONCELOS PACHECO

43


Study of the inhibition capacity of an 18-merpeptide domain of GBV-C virus on gp41-FPHIV-1 activity.Haro, I., Gómara, M.J., Galatola, R., Domènech,O., Prat, J., Girona, V., Busquets, M.A. BBA-Biomembranes 1808 1567-1573, 2011

Antibodies against β-fibrin synthetic peptides:A study of their association with theimmunogenetic background and diseasecourse of rheumatoid arthritis patients.Haro, I., Gómara, M.J., Pérez, M.L., Viñas, O.,Ercilla, G., Gómez-Puerta, J.A., Sanmartí, R. Eur. J. Med. Chem. 46 1095-1102, 2011

44

Research highlights SEFFECT OF SYNTHETIC PEPTIDES BELONGING TO E2ENVELOP PROTEIN OF GB VIRUS C (GBV-C) ON HUMANIMMUNODEFICIENCY VIRUS TYPE 1Recent years have seen the publication ofnumerous works in which co-infection with GBvirus C (GBV-C) and HIV has been associated withslower progression of the illness and a highersurvival rate of patients once AIDS has developed.The mechanism by which the GBV-C virus has a“protective effect” in patients with HIV has still notbeen defined. 124 synthetic sequences of the GBV-C E2 envelope protein have been obtained by SPPSand published in J. Med. Chem. 53, 6054, 2010.The interaction of certain GBV-C peptidesequences with the HIV-1 fusion peptide has beenproven through the use of biophysical techniques.We also show how GBV-C E2 domains notablydecrease cellular membrane fusion and interferewith the HIV-1 infectivity in a dose-dependentmanner highlighting their potential utility in futuretherapies anti-HIV-1.

THE USE OF CHIMERIC VIMENTIN CITRULLINATED PEPTIDESFOR THE DIAGNOSIS OF RHEUMATOID ARTHRITIS. Anti-citrullinated protein/peptide antibodies(ACPAs) are considered the most specific serologicmarkers of rheumatoid arthritis (RA). ACPAsrecognize proteins or peptides with arginineresidues converted to citrulline by a post-translational modification and have diagnostic andprognostic significance. ACPAs can be detectedusing enzyme-linked immunoabsorbent assayswith different citrullinated protein or peptide

substrates. The most widely used in clinical practiceis the cyclic citrullinated peptide 2 assay (CCP2). Inour group we have obtained three chimericfibrin/filaggrin peptides and evaluated thediagnostic yield of the ELISA tests based on thesepeptides to compare their sensitivity and specificityin RA and other disease groups with thecommercial CCP2 test. Our results published in J.Med. Chem. 54, 7486, 2011, highlight theputative application of chimeric peptides for thedesign of RA diagnosis systems and imply thatmore than one serological test is required to classifyRA patients based on the presence or absence ofACPAs. Each of the target molecules reported(fibrin, vimentin, filaggrin) has a specific utility inthe identification of a particular subset of RApatients.


45

STAFF GREGORIO VALENCIA PARERA, GROUP LEADERGEMMA ARSEQUELL RUIZ

Ph. D.LLUÍS BOSCH HEREU

Ph. D. STUDENTSMÓNICA ROSA EXPÓSITO

Unit of Glycoconjugate ChemistryThe focus of the Unit is to apply chemical tools tothe study of biochemical or medicinal chemistryproblems. These tools first involved peptidesynthesis, latter carbohydrate chemistry and morerecently, study of halogenation reagents and biarylcompounds preparation by C C bond forming crosscoupling reactions. The fields of interest startedwith the study of enzyme catalysis, pain andinmunity related mechanisms and compounds upto the more recent topics of transthyretinfibrillogenesis inhibitors and imaging diagnosticsfor neurodegenerative diseases using radiotracers. The current research activities fall mainly into threeareas: 1) Synthesis and biological study ofantinociceptive drugs. 2) Application in peptidechemistry of the iodinating reagent IPy2BF4(Barluenga's reagent). 3) Synthesis of transthyretinamyloidosis inhibitors. 4) Development ofradiotracer probes for the imaging diagnostics ofneurodegenarative diseases.


Synthesis, biological evaluation and structuralcharacterization of novel glycopeptideanalogues of nociceptin N/OFQ.Arsequell, G., Rosa, M., Mayato, C., Dorta, R.L.,Gonzalez-Nunez, V., Barreto-Valer, K., Marcelo, F.,Calle, L.P., Vázquez, J.T., Rodríguez, R.E., Jiménez-Barbero, J., Valencia, G. Org. Biomol. Chem. 9 6133-6142, 2011Ligand-binding properties of humantransthyretin.Pinto, M., Blasi, D., Nieto, J., Arsequell, G.,Valencia, G., Planas, A., Quintana, J., Centeno,N.B. Amyloid 18 (SUPPL. 1) 51-54, 2011

Drug discovery targeted at transthyretincardiac amyloidosis: Rational design,synthesis, and biological activity of newtransthyretin amyloid inhibitorsBlasi, D., Pinto, M., Nieto, J., Arsequell, G.,Valencia, G., Planas, A., Centeno, N.B., Quintana, J. Amyloid 18 (SUPPL. 1) 55-57, 2011Retrospective mapping of SAR data for TTRprotein in chemico-biological space usingligand efficiency indices as a guide to drugdiscovery strategies.Blasi, D., Arsequell, G., Valencia, G., Nieto, J.,Planas, A., Pinto, M., Centeno, N.B., Abad-Zapatero, C., Quintana, J. Mol. Inform. 30 161-167, 2011


1) As part of our SAR studies on opioid ligands andof pain mechanisms and because glycosylationcauses important changes in the nativeconformation, stability, activity and processing ofmany proteins we have been exploring theglycoconjugate approach for the rational drugdesign of new opioids. In applying this strategy tothe N/OFQ peptide which is the native ligand of thepain related drug target NOP receptor, we havesynthesized three N/OFQ analogues. In testingthem in competition binding assays using clonedzebrafish NOP receptor preparations theglycopeptide which was glycosylated at Thr5

showed a remarkably reduced bind¬ing affinitycompared to the other two analogues and theparent compound. In aqueous solutions thesepeptides were mainly popu¬lated by random coilconformers as seen by NMR and circular dichroism.However, in membrane mimic environments thesepeptides exhibited certain proportion of alfa helixstructure as measured by NMR. Interestingly, underthese condition only the Thr5 glycosylated peptidealso presented a population of folded hairpin likegeometries which make us to speculate that linealhelical structures are more complementary to theNOP receptor than folded ones that amy accountfor the reduced binding affinity of this analogue.

2) Transthyretin (TTR) is a homotetrameric plasmaprotein that functions as the backup transporter forthyroxin hormone. Hereditary mutations on TTR arein the cause of a group of rare and always fatalsystemic amyloid diseases. One of the most advancedand best studied possible pharmacologicaltreatments relies on the use of small moleculecompounds that bind into the channel formed by thetetramer and kinetically stabilize its disociation intomonomers thus preventing future aggregationevents. During 2011 we have published threecomputationally based contributions to the aboveoutlined drug discovery effort. The MolecularInformatics article deals with the implementation andapplication of the concept of Ligand EfficiencyIndexes (LEIs) to a family of 80 salicylates with adiflunisal core structure that we have previ¬ouslyprepared with the aim to optimize the biologicalproperties of this series of TTR aggregation inhibitors.After retrospec¬tively prioritize the compounds onthe nBEI SEI plane we have undertaken a prospectiveLEI analysis based in theoretical potency calculationsusing docking protocols on a 2300 compoundsselected from the MMsINC database that has led topropose 12 new analogues that are in the process ofbeing synthesized and biologically tested to validatethis optimization strategy.

Research highlights

46


DEPARTMENT OF CHEMICAL AND BIOMOLECULAR NANOTECHNOLOGY

4


Nanoscience and Nanotechnology is a multidisciplinary wide field, defined as the study ofentities with dimensions in the nanometer range and the search for its technologicalapplications. Our Department is focused on the understanding of bioactive molecules(oligonucleotides, macrobiomolecules, antibodies, organic molecules and drugs), self-organized supramolecular colloidal systems, nanostructured materials and devices. Theresearch outcome may have useful applications in diagnostics (biosensors for diseaseprevention), therapeutics (protection against diseases), formulation of new products(pharmaceutical, cosmetics, agrochemicals, food products, etc.), preparation of newadvanced materials (nanoparticles and porous materials for novel applications) and inbioorganic synthesis (development of new high added value products). The Departmenthas a deep expertise in chemistry of oligonucleotides, developing novel biosensors withimproved features, controlling self-aggregation of amphiphilic molecules, the formation ofnew nanostructured materials and chemistry of drugs and bioactive substances, amongothers. The methodologies used imply: the synthesis using combinatorial chemistry toolsand designing and screening virtual libraries; the rational design of molecules with affinityto dsDNA and investigating the processes controlled by RNAi; the controlled production ofselective antibodies and integrating such biomolecules with nanomaterials and devices; theformation of complex supramolecular structures (micelles, liquid crystals, microemulsions,nano-emulsions, highly concentrated emulsions, etc.); and the use of these systems astemplates for formation of materials (organic, inorganic, hybrid) with controlled size andmorphology, as well as new drug delivery systems. The Department is formed byconsolidated multidisclipinary research teams, with a strong capacity to secure funds fromSpanish public institutions, foundations, European programs and contracts of technologytransfer to the private sector.

Research groups Nanobiotechnology and Molecular Diagnostics Nucleic Acids Chemistry Colloid and Interfacial Chemistry Group Bioorganic Chemistry Surface Chemistry Group

Head: Jordi Esquena Moret (after July 2011) and Mª Pilar Marco Colàs (before July 2011)

DEPARTMENT OF CHEMICAL AND BIOMOLECULAR NANOTECHNOLOGY

49


The Nanobiotechnology and MolecularDiagnostics Group has focused on thedevelopment of novel molecular diagnostic tools toprovide alternatives to the actual limitations existingin several fields, but particularly in the clinical andfood safety areas. The combination ofnanotechnological and biotechnological advanceshas given rise to novel molecular diagnosticapproaches to improve efficiency and/or to refineand extend the limits of detection. Nanostructuredsurfaces and nanoparticles may be the basis for theconstruction of functional hybrid materialsconsisting of both organic (biomolecules) andinorganic components. Biosensors are among thepotential applications of these new immunosensorsusing antibodies as biorecognition elementsdisplaying fascinating features such as the possibilityto respond selectively to biological or bioactivesubstances and the ability to respond in aphysiological manner. The unique properties ofcertain nanomaterials combined with the excellentfeatures of the antibodies allow for envisaging novelexquisitely sensitive chemical and biological sensors.


Recent advances in analytical and bioanalysisapplications of noble metal nanorods.Mannelli, I., Marco, M.P. Anal. Bioanal. Chem. 398 2451-2469, 2010Erratum: Anal. Bioanal. Chem. 399 1923, 2011Determination of atrazine residues in redwine samples. A conductimetric solution. Valera, E., Ramón-Azcón, J., Barranco, A., Alfaro,B., Sánchez-Baeza, F., Marco, M.P., Rodríguez, A. Food Chem. 122 888-894, 2010Gel-based immunotest for simultaneousdetection of 2,4,6-trichlorophenol andochratoxin A in red wine.Beloglazova, N.V., Goryacheva, I.Y., Rusanova,T.Y., Yurasov, N.A., Galve, R., Marco, M.P., DeSaeger, S. Anal. Chim. Acta 672 3-8, 2010Competitive multi-immunosensing ofpesticides based on the particle manipulationwith negative dielectrophoresis.Ramón-Azcón, J., Yasukawa, T., Lee, H.J., Matsue,T., Sánchez-Baeza, F., Marco, M.P., Mizutani, F. Biosens. Bioelectron. 25 1928-1933, 2010

Electronic anabolic steroid recognition withcarbon nanotube field-effect transistors.Martínez, M.T., Tseng, Y.-C., Salvador, J.P., Marco,M.P., Ormategui, N., Loinaz, I., Bokor, J. ACS Nano 4 1473-1480, 2010A high-throughput screening (HTS)immunochemical method for the analysis ofstanozolol metabolites in cattle urine samples.Salvador, J.P., Sánchez-Baeza, F., Marco, M.P. J. Chromatogr. B 878 243-252, 2010Evaluation of immunoassays as an alternativefor the rapid determination of pesticides inwine and grape samples.Argarate, N., Arestin, M., Ramón-Azcón, J.,Alfaro, B., Barranco, A., Sánchez-Baeza, F.,Marco, M.P. J. AOAC Int. 93 2-11, 2010Intracellular silicon chips in living cells.Gómez-Martínez, R., Vázquez, P., Duch, M.,Muriano, A., Pinacho, D., Sanvicens, N., Sánchez-Baeza, F., Boya, P., de la Rosa, E.J., Esteve, J.,Suárez, T., Plaza, J.A.Small 6 499-502, 2010

Nanobiotechnology and Molecular Diagnostics

50

STAFFM. PILAR MARCO COLÁS, GROUP LEADER ROGER GALVE BOSCH FRANCISCO SÁNCHEZ BAEZA

TECHNICIANSNÚRIA PASCUAL DURANMARTA RUIZ ARRIBASANA GONZÁLEZ GONZÁLEZRUTH BABINGTON

RESEARCH SCIENTISTDANIEL GONZÁLEZ PINACHO

Ph. D.J.PABLO SALVADOR VICO ENRIQUE VALERA CANO

Ph. D. STUDENTSGLORIA COLOM SANMARTÍ RAUL GARCÍA FEBRERO CARME PASTELLS DÍEZ SALVADOR PETANÁS ESTEBAN ESTER VILA ROCAALEX HERNÁNDEZ ALBORSNURIA TORT ESCRIBÀSÓNIA MATAS MOYA

MASTER STUDENTSMARTA BROTO AVILES


51

Validation of an enzyme-linkedimmunosorbent assay for detectingsulfonamides in feed resources.Jiménez, V., Adrián, J., Guiteras, J., Marco, M.P.,Companyo, R.J. Agric. Food Chem. 58 7526-7531, 2010Juvenile hormone and allatostatins in theGerman cockroach embryo.Maestro, J.L., Pascual, N., Treiblmayr, K., Lozano,J., Bellés, X.Insect Biochem. Mol. Biol. 40 660-665, 2010Capture and culturing of living cells onmicrostructured DNA substrates.Reisewitz, S., Schroeder, H., Tort, N., Edwards,K.A., Baeumner, A.J., Niemeyer, C.M.Small 6 2162-2168, 2010Mass spectrometric characterization of urinarytoremifene metabolites for doping controlanalyses.Gómez, C., Pozo, O.J., Díaz, R., Sancho, J.V.,Vilaroca, E., Salvador, J.P., Marco, M.P.,Hernández, F., Segura, J., Ventura, R. J. Chromatogr. A 1218 4727-4737, 2011Preliminary study for simultaneous detectionand quantification of androgenic anabolicsteroids using ELISA and pattern recognitiontechniques.Calvo, D., Tort, N., Pablo Salvador, J., Marco,M.P., Centi, F., Marco, S. Analyst 136 4045-4052, 2011Development of a cellular biosensor for thedetection of 2,4,6-trichloroanisole (TCA).Varelas, V., Sanvicens, N., Marco, M.P., Kintzios, S. Talanta 84 936-940, 2011Quantum dot-based array for sensitivedetection of Escherichia coli Sanvicens, N., Pascual, N., Fernández-Argüelles,M.T., Adrián, J., Costa-Fernández, J.M., Sánchez-Baeza, F., Sanz-Medel, A., Marco, M.P. Anal. Bioanal. Chem. 399 2755-2762, 2011Biosensors for pharmaceuticals based onnovel technology.Sanvicens, N., Mannelli, I., Salvador, J.-P., Valera,E., Marco, M.-P. Trac-Trend. Anal. Chem. 30 541-553, 2011

A label-free and portable multichannelsurface plasmon resonance immunosensor foron site analysis of antibiotics in milk samples.Fernández, F., Hegnerová, K., Piliarik, M.,Sanchez-Baeza, F., Homola, J., Marco, M.P.Biosens. Bioelectron. 26 1231-1238, 2010Portable surface plasmon resonanceimmunosensor for detection offluoroquinolone antibiotic residues in milk.Fernandez, F., Pinacho, D.G., Sánchez-Baeza, F.,Marco, M.P.J. Agric. Food Chem. 59 5036-5043, 2011Development of stable, water dispersible andbiofunctionalizable superparamagnetic ironoxide nanoparticles.Miguel, N., Bomatí-Miguel, O., Colom, G.,Salvador, J., Marco, M.P., Santamaría, J.Chem. Mat. 23 2795-2802, 2011Development of an immunoassay forterbutryn: Study of the influence of theimmunization protocol.Sanvicens, N., Varela, B., Ballesteros, B., Marco, M.P. Talanta 89 310-316, 2011A novel free radical scavenger rescues retinalcells in vivo.O’Driscoll, C., Doonan, F., Sanvicens, N.,Messeguer, A., Cott, T.G.Exp. Eye Res. 93 65-74, 2011

Publications (books and book chapters)Sanvicens, N.; Fernández, F.; Salvador, J.P.; Marco,M. P., Current Status and Future Prospects forNanoparticle-Based Technology in HumanMedicine. in Nanoplatform-Based Molecular Imaging, John Wiley & Sons, Inc.: 2011; pp 781-813.Muriano, A., Salvador, J.-P., Galve, R., Marco,M.P., Anisha, T.K.N., Loza-Alvarez, P., Soria, S. High sensitive non-linear detection of steroidsby resonant double grating waveguidestructures based immunosensors.in Integrated Optics: Devices, Materials, andTechnologies XV (eds J.E. Broquin, G. Nunzi Conti)Proc. SPIE 7941, 794114, 2011http://dx.doi.org/10.1117/12.876456


52

In the last two years, the Nanobiotechnology andMolecular Diagnostics Group has continuedstudying novel micro and nano(bio)technologicalapproaches to improve the efficiency of thediagnostic tools, particularly in the food safety andclinical fields. In this context, the group haspublished relevant results addressed to developimmunochemical techniques (ELISA) for the broaddetection of antibiotics such as sulfonamides andfluoroquinolones or the detection of bacteria suchas Escherichia coli, pesticides such as paraquat,antiestrogenic hormones such as toremifene orstanozolol, as well as a mulltianalyte immunoassaysfor the detection of up to 25 different antibiotics.Several of these immunoassays have been used forthe analysis of different matrices such asenvironmental samples (river and sea water, wood),milk, honey, wine, grape juice, human and cattleurine, blood and hair.Interesting results were obtained within theelectrochemical immunosensors research lineshowing the potential of different configurations,such as the CNTFET (carbon nanotube field-effecttransistors) arrrays for the immunochemicaldetermination of biomarkers at low concentrations(Martinez et al. ACS Nano). Moreover, incollaboration with Prof. Kintzios (AgriculturalUniversity of Athens) a cellular biosensor has beendeveloped for the detection of TCA, a contaminantof the wine. In the field of optical devices, a SPRimmunosensor for the simultaneous determinationof a panel of antibiotics has been developed, usinga novel technology that could lower the price of these devices, in addition to offer the possibilityto be use on site (Fernandez et al, Biosens.Bioelectronics). The ability to internalize convenientlybiofunctionalized chips for biomonitoring ofintracellular processes has been demonstrated(Gomez-Martinez et al. Small). Moreover, thepossibility of capturing living cells on substrates forsubsequent growth using antibody arrays, preparedby DNA-directed strategies, has been shown(Reisewitz et al, Small) in collaboration with Prof.Niemeyer (Dormunt, Germany). An interestingmicroarray approach based on labeling antibodieswith QDs has been developing allowing detectingdown to 2 CFU/mL of E. coli (Sanvicens et al., ABC).The group has also collaborated with Prof.Santamaria (Zaragoza, Spain) on the demonstrationof the biofunctionality of novel water-dispersablesuperparmagnetic iron oxide nanoparticles (Miguel-Sancho et al., Chem. Mat).The group is currently involved in projects for thedevelopment of systems for the early detection andquantification of biomarkers for diseases such asAlzheimers and cardio-vascular diseases. In thecase of Alzheimers the early detection of 4 knownbiomarkers will allow for the precocious treatmentfor the disease. Biosensors are being developed forthe detection of cardiovascular diseases. This

research is being performed within the context oftwo INNPACTO projects (IPT-2011-1337-010000and IPT-2011-1055-900000, MEC, Spain) and theCAJAL4EU projects (EC-FP7-ICT-JU-ENIAC-120215), all of them characterized by a highparticipation from enterprises and involving thedevelopment and application of newnanoelectronic devices for diagnostics. Pharmasan Laboratories Inc. (USA) havecommissioned the Nanobiotechnology andMolecular Diagnostics Group group for thedevelopment of point of care test (POCT) systemsrelated to neurological disorders. Similarly, acollaboration contract has been signed withUNISENSOR SA (Belgium) addressed to thedevelopment of test-kits for food safety.In respect to the food safety research line it isrelevant the result obtained within theCONffIDENCE project (FP7-KBBE-2007-1) with theobjective of improving food safety in Europe by thedevelopment of fast and cost-efficient methods forthe detection of a wide range of chemicalcontaminants in different food products, based onan electrochemical magneto immunosensor assay.Several patents have been awarded(PCT/ES2009/000578 and P200702623) and newones have been requested in relation to newtransducers (PCT/ES2020/070824) and antibodies(P201031721) for diagnostics. Moreover some ofthese patents have been licensed to the privatesector.The Custom Antibody Service (Cabs), wherebyantibodies can be custom produced and technical assistance is offered to companies andresearch institutes in respect to the preparation ofimmunoreagents, bioconjugates and immunochemicalmethods, is gaining acceptance and novel servicesare being incorporatedDuring this period, the Nanobiotechnology andMolecular Diagnostics Group has participated in avariety of International Congresses e.g.in theWorld Congress on Biosensors (Glasgow, UK) with8 communications. The Food Integrity andTraceability Conference (Belfast, UK) where thedevelopment of immunosensors for pesticides waswell received or the IMAGINENANO (Bilbao, Spain)presenting the latest advances of the group in thenanobiotechonology research line.Finally, the Nanobiotechnology and MolecularDiagnostics group continues to work on newstrategies for the screening of small organicmolecules, including condumetric sensors, opticalbiosensors, quantum-dot based arrays, microarraysand the standard ELISA etc.

Research highlights


STAFFRAMON ERITJA CASADELLÀ, GROUP LEADER

Ph. D.ANNA MARIA AVIÑÓ ANDRÉSMARIA CARME FÀBREGA CLAVERÍAALEJANDRA VICTORIA GARIBOTTISANTIAGO GRIJALVO TORRIJOSONIA PÉREZ RENTEROMONTSERRAT TERRAZAS MARTÍNEZ

Ph. D. STUDENTSMARGARITA ALVIRA TORRERUBEN FERREIRA AGUILERA BRENDAN MANNIG SANDRA MILENA OCAMPO MARIA TINTORÈ GASULLA


Acridine and quindoline oligomers linkedthrough a 4-aminoproline backbone prefer G-quadruplex structures.Ferreira, R., Artali, R., Farrera-Sinfreu, J., Albericio,F., Royo, M., Eritja, R., Mazzini, S. Biochim. Biophys. Acta-Gen. Subj. 1810 769-776,2011Synthesis and properties of oligonucleotidescarrying isoquinoline imidazo[1,2-a]azinefluorescente units. Pérez-Rentero, S., Kielland, N., Terrazas, M.,Lavilla, R., Eritja, R. Bioconjugate Chem. 21 1622-1628, 2010Synthesis, cell-surface binding and cellularuptake of fluorescently labelled glucose-DNAconjugates with different carbohydratepresentation.Ugarte-Uribe, B., Pérez-Rentero, S., Lucas, R.,Aviñó, A., Reina, J. J., Alkorta, I., Eritja, R.,Morales, J. C. Bioconjugate Chem., 21 1280-1287, 2010Synthesis and structural properties ofoligonucleotides covalently linked to acridineand quindoline derivatives through athreoninol linker.Aviñó, A., Mazzini, S., Ferreira, R., Eritja, R.Bioorg. Med. Chem. 18 7348-7356, 2010Stepwise synthesis of oligonucleotide-peptideconjugates containing guanidinium orlipophilic groups in their 3’-termini. Grijalvo, S., Terrazas, M., Aviñó, A., Eritja, R. Bioorg. Med. Chem. Lett. 20 2144-2147, 2010

Modified siRNAs for the study of the PAZdomain. Somoza, A., Terrazas, M., Eritja, R. Chem. Commun. 46 4270-4272, 2010Triplex-stabilizing properties of parallelclamps carrying LNA derivatives at theHoogsteen strand.Alvira, M., Eritja, R. Chem. Biodivers. 7 376-382, 2010Fabrication of patterned surfaces by photo-lithographic exposure of DNA-hairpinscarrying a novel photolabile group.Manning, B., Leigh, S.J., Ramos, R., Preece, J.,Eritja, R.J. Exp. Nanoscience 5 26-39, 2010Synthesis of oligonucleotides carrying aminolipid groups at the 3’-end for RNAinterference studies. Grijalvo, S., Ocampo, S.M., Perales, J.C., Eritja, R. J. Org. Chem. 75 6806-6813, 2010Solid-phase synthesis ofoligodeoxynucleotides carrying N4-[2-t-butyldisulfanyl)ethyl]-5-methylcytosine.Pérez-Rentero, S., Garibotti, A.V., Eritja, R.Molecules 15, 5692-5707, 2010Highly polar carbohydrates stack onto DNAduplexes via CH/π interactions. Lucas, R., Gómez-Pinto, I., Aviñó, A., Reina, J.J.,Eritja, R., González, C., Morales, J.C. J. Am. Chem. Soc. 133 1909-1916, 2011

53

Nucleic Acids ChemistrySynthetic oligonucleotides are convenient tools fora large number of studies. The aim of our group isthe study of the methodology used for thesynthesis of DNA and RNA derivatives in order toobtain new compounds with new and / orimproved properties. The projects undertakenalong 2008-2009 deal with 1) conjugation of smallmolecules to DNA and RNA for a potential use inDNA/ RNA therapeutics, 2) the effect of modifiedbases in the structural and biological properties ofoligonucleotides, and 3) the use of modifiedoligonucleotides in the assembly of nanomaterialsand biosensors.


54

A direct, efficient method for the preparationof siRNAs containing ribo-like Northbicyclo[3.1.0]hexane pseudosugars. Terrazas, M., Aviñó, A., Siddiqui, M., Márquez, V.,Eritja, R. Org. Lett., 2011, 13(11), 2888-2891, 2011Effect of North bicyclo[3.1.0]hexanepseudosugars on RNA interference. A novelclass of siRNA modification. Terrazas, M., Ocampo, S.M., Perales, J.C.,Márquez, V.E., Eritja, R. ChemBioChem, 12 1056-1065, 2011Chemical equilibria studies using multivariateanalysis methods.Jaumot, J., Eritja, R., Gargallo, R. Anal. Bioanal. Chem. 399 1983-1997, 2011Synthesis and properties of small interferingRNA duplexes carrying 5-ethyluridineresidues.Terrazas, M., Eritja, R.Mol. Divers. 15 677-686, 2011Synthesis and in vitro inhibition properties ofsiRNA conjugates carrying glucose andgalactose with different presentation.Aviñó, A., Ocampo, S. M., Lucas, R., Reina, J.J.,Morales, J.C., Perales, J.C., Eritja, R. Mol. Divers. 15 751-757, 2011Evaluation of the structure-activityrelationship of thrombin binding aptamers byvoltammetry and atomic force microscopy.Diculescu, V.C., Chiorcea-Paquim, A.M., Eritja, R.,Oliveira-Brett, A.M. J. Electroanal. Chem. 656 159-166, 2011Preparation and AFM-characterization of self-assembled monolayers functionalized with athrombin binding aptamer”Manning, B., Gállego, I., Tintoré, M., Fàbrega, C.,Aviñó, A., Eritja, R. Int. Rev. Biophys. Chem. 2 74-77, 2011Influence of pH, temperature and the cationicporphyrin TMPyP4 on the stability of the i-motif formed by the 5’-(C3TA2)4-3’ sequenceof the human telomere.Fernández, S., Eritja, R., Aviñó, A., Jaumot, J.Gargallo, R. Int. J. Biol. Macromol. 49 729-736, 2011Functionalization and self-assembly of DNAbidimensional arrays. Garibotti, A.V., Pérez-Rentero, S., Eritja, R Int. J. Mol. Sci. 12 5641-5651, 2011Use of oligonucleotides carrying photolabilegroups for the control of the deposition ofnanoparticles in surfaces and nanoparticleassociation.Manning, B., Eritja, R.Int. J. Mol. Sci. 12 7238-7249, 2011

Synthesis of lipid-oligonucleotide conjugatesfor inhibition of gene expression.Grijalvo, S., Ocampo, S. M., Perales, J. C., Eritja, R. Chem. Biodivers. 8 287-299, 2011Synthesis and structural properties of G,T-parallel clamps carrying 8-aminopurineresidues.Aviñó, A., Cubero, E., Gargallo, R., González, C.,Orozco, M., Eritja, R. J. Nucleic Acids, ID 763658, 11 pages, 2010.doi:10.4061/2010/763658; PMID: 20798879.G-quadruplex Nucleic Acids.Eritja, R., Mergny, J.L., Montesarchio, D., Spindler,L., Webba da Silva, M. J. Nucleic Acids, ID 147650, 2 pages, 2010.doi:10.4061/2010/147650; PMID: 20814544.Editorial.Synthesis and G-quadruplex bindingproperties of defined acridine oligomers.Ferreira, R., Aviñó, A., Pérez-Tomás, R., Gargallo,R., Eritja, R J. Nucleic Acids, ID 489060, 10 pages, 2010.doi:10.4061/2010/489060; PMID: 20725626.Thrombin binding aptamer quadruplexformation: AFM and voltammetriccharacterization.Diculescu, V.C., Chiorcea-Paquim, A.M., Eritja, R.,Oliveira-Brett, A.M.J. Nucleic Acids, ID 841932, 8 pages, 2010.doi:10.4061/2010/841932; PMID: 20798847.Development of a novel fluorescence assay based on the use of the thrombinbinding aptamer for the detection of O6-alkylguanine-DNA alkyltransferase activity. Tintoré, M., Aviñó, A., Ruiz, F.M., Eritja, R.,Fàbrega, C. J. Nucleic Acids, ID 632041, 9 pages, 2010.doi:10.4061/2010/632041, PMID: 20936180. Branched RNA: a new architecture for RNAinterference.Aviñó, A., Ocampo, S.M., Perales, J.C., Eritja, R. J. Nucleic Acids, ID 586935, 7 pages, 2011.doi:10.4061/2011/586935 (2011). PMID: 21461398.Synthesis and properties ofoligodeoxynucleotides carrying 2-aminopurine.Fàbrega, C., Grijalvo, S., Eritja, R. Open Org. Chem. J. 5 1-8, 2011Functionally enhanced siRNA targeting TNFαattenuates DSS-induced colitis and TLR-mediated immunostimulation in mice.Ocampo, S.M., Romero, C., Aviñó, A., Burgueño,J., Gassull, M.A., Bermúdez, J., Eritja, R.,Fernández, E., Perales, J.C.Mol. Ther. 20 382-390, 2011


Aviñó, A., Grijalvo, S., Pérez-Rentero, S.,Garibotti, A., Terrazas, M., Eritja, R. Synthesis of oligonucleotide-peptideconjugates for biomedical and technologicalapplications.

in Methods in Molecular Biology, Vol. 751, Ch.14, 223-238, 2011. “Bioconjugation Protocols2nd edition” (S.S. Mark Ed.). Humana Press,Springer, New York.

Publications (books and book chapters)

55

Research highlightsControl of the gene expression inhibitory propertiesof nucleic acids by chemical modification. The use of synthetic oligonucleotides to controlgene expression has triggered the search for newoligonucleotide derivatives with improvedtherapeutic potential. In these cases nucleic acidsare used for the inhibition of a specific gene byblocking gene translation or gene transcription orby stimulating the degradation of a particularmessenger RNA. Different strategies are possible.In the antisense strategy synthetic oligonucleotidescomplementary to the messenger RNA of a givengene are used to inhibit translation of messengerRNA to protein. In the siRNA strategy, small RNAduplexes complementary to messenger RNA bindto a protein complex named RISC. siRNA duplexescontains two strands: the antisense or guide strandthat binds to RISC and the sense or passengerstrand that is released as a result of the interactionof the siRNA duplex with RISC. The complexformed by the antisense or guide RNA strand andthe protein complex RISC is able to catalyze theefficient degradation of a specific messenger RNA,lowering the amount of target protein.

During these years we have concentrated ourefforts in the development of novel derivatives ofRNA to enhance RNA interference. We used theluciferase and the TNF-α as target genes. TNF-αwas selected because is a major mediator ofapoptosis as well as inflammation and immunity,and it has been implicated in the pathogenesis ofa wide spectrum of human diseases. On the otherhand, luciferase production can be measured bychemiluminescence. In the dual luciferase assaycells are transfected with two plasmids: one withthe firefly luciferase gene and the other carryingthe Renilla luciferase gene. One of the genes wasinhibited by specific siRNA duplexes while the otheris used as control. Using this assay it is possible tomeasure the inhibition of gene expression of oneluciferase by chemiluminescence. The resultsachieved by the group are summarized below.

1.- Stability of siRNA in serum. The matter ofstability against nucleases has been addressed bymodifying siRNA duplexes with bicyclohexanepseudosugars. A structural parameter that is crucialin DNA/ RNA structure is the pucker of the furanosering. In standard B-DNA, the pucker is 2’-endo or“South” (S) whereas A-DNA and RNA arecharacterized by 3’-endo or “North” (N) pucker of N-type conformation. Several authors have focused on

the synthesis of novel nucleosides that are biasedtoward one specific ring puckering as potentialtherapeutic agents. We have studied the effect of theN-type derivatives in RNA interference experiments.Some pseudonucleoside modifications, either atguide or passenger strands, have a strong stabilizingeffect against degradation without decreasing theinhibitory properties of siRNA duplexes. Thesecompounds were provided by Dr. Marquez (NIH,USA). siRNAs carrying 5-ethyluridine were alsoevaluated, as this nucleoside is known to stabilizeDNA against nuclease degradation. The presence ofthis nucleoside in siRNA had no effect in nucleasestability but it induced slightly better inhibitoryproperties.

2.- Cellular uptake. To address the problem ofcellular uptake several siRNA conjugates carryingpeptides, lipids, intercalating agents, andcarbohydrates were prepared. More than 30 newsiRNA duplexes were synthesized and the inhibitoryproperties of these conjugates on cell culture wereevaluated in the laboratory of Dr. Jose C. Perales(UB, Barcelona). The best results out of this studywere obtained with oligonucleotides carryinglipids.

3.- siRNA and RISC interactions. The modulationof the affinity of siRNA to RISC has been addressedby synthesizing siRNA duplexes with guide strandscarrying several groups designed to fit on anhydrophobic pocket of RISC. We observed that theinhibitory properties of siRNA duplexes carryingmodified guide strands are being affected by thesize of the group at the 3’-end, while the samemodification on the passenger strand did not yieldany change of activity.

4.- Off-target effects and clinical trials. Wetested the effect of our novel chemicalmodifications on innate immunoestimulationmediated by toll-like receptors. This is an importantsource of undesired off-target effects and it isespecially relevant in the design of anti-inflammatory compounds. Some modificationsshowed to have a reduced immunoestimulationand a strong and prolonged specific inhibitoryaction. During this study we observed anextraordinary anti-inflammatory activity onmacrophages induced by one of our chemically-modified siRNAs. This compound contained 2’-O-methyl-RNA modifications at the 5’ and apropandiol molecule at the 3’-end, both


56

modifications in the passenger strand. This siRNAwas selected for a preclinical study in a mousemodel of inflammatory bowel disease (IBD). Analadministration of the modified siRNA resulted inextraordinary anti-inflammatory activity. A genearray study on siRNA treated animals confirmedthat anti-inflammatory activity is the result of areduced inflammatory process caused by thespecific action of the siRNA targeting TNF-alpha.The unmodified siRNA was toxic due to thestimulation of the immune system. This work wascarried out in collaboration with Dr. J.C. Perales(UB) and Dr. E. Fernández (UAB).

Oligonucleotides and Nanotechnology.A remarkable development in the DNAnanotechnology field was the use of stable DNAHolliday junctions with addressable sticky ends toform two-dimensional DNA crystals. The principlesof construction described by Seeman have beenused and adapted to generate systems with finecontrol of shape and function. For example, largeDNA lattices have been transformed into highlyregular two-dimensional DNA networks onsurfaces that provide templates for the depositionof gold nanoparticles in a regular square networkby using biotin-streptoavidin recognition system.We become interested in the preparation ofthiolated 2D DNA arrays because the specialreactivity of the thiol group will allow thefunctionalization of 2D DNA arrays. Thiols groupshave a strong affinity for gold surfaces and theycan also be used to introduce peptides and proteinsas well as large number of molecules that havebeen functionalized with maleimido groups orbromo- and iodo-acetyl groups. We insertedreactive thiol groups at the nucleobase at specificsites of a well-characterized bidimensional DNAlattice to study the formation of the DNA latticeson gold, a surface that allows electrical contacts.We demonstrated that DNA lattices carrying asingle thiol derivative in each topological hairpinmarker can be prepared and deposited on micasubstrates. However and most importantly we alsodemonstrated that these thiolated 2D DNA arraysare readily deposited on gold surfaces whileunmodified 2D DNA arrays are not able to do so.

In addition we have developed a newphotolithographic method that uses photolabileDNA hairpins to make patterns on silicon oxide andgold surfaces. The method described offers anattractive option for the fabrication of patternedsurfaces with potential interest in electronics andbiosensors.

G-quadruplex.Guanine-rich sequences capable of forming G-quadruplex structures have been found intelomeres and in transcriptional regulatory regionsof important oncogenes, such as c-myc, and c-kit.

Ligands that selectively bind and stabilize thesestructures have become appealing anticancerdrugs. We have started a study of G-quadruplexstructures present at the initiation sites ofoncogenes, as well as a study of their interactionwith small drugs. Moreover, we studied theinteraction of G-rich sequences with theircomplementary C-rich strands that may also forma quadruplex structure known as i-motif. This workis done in collaboration with the group ofRaimundo Gargallo (UB). A detailed analysis of theequilibrium formed by the G-quadruplex of TBAand oncogenes such as bcl-2 and c-kit and thecorresponding complementary C-rich sequenceswas carried out in order to determine the relativeamount of duplex or quadruplexes at different pHs.

Furthermore, the interaction of DNA-binding drugswith G-quadruplex structures is being studied, aswell as, the synthesis of new quadruplex bindingdrugs. We have developed a method that allowsthe rapid and efficient synthesis of oligomersconsisting of several intercalating drugs.Interestingly, the oligomers produced in thismanner have a remarkable affinity for biologicallyrelevant quadruplex, such as telomeric sequencesand oncogene promoters. The reagents developedin this project were also used to synthesizeoligonucleotides with enhanced hybridizationproperties, as well as more stable quadruplexes.

Design of inhibitors of DNA repair mechanism incancer chemotherapy. Chemotherapy still constitutes the majorpharmacological approach against cancer.Antiproliferative drugs are highly cytotoxic andaggressive agents. Under attack, the biochemicalrepair systems of the cancer cell machineryrespond, trying to mitigate the cellular damageinduced by these agents. As a result, their clinicalefficacy is often limited. High doses are requiredand as a consequence serious secondary effects arecommonplace. Recent advances in the molecularbiology of cancer have identified key pathwaysinvolved in the DNA repair pathways induced bychemotherapeutic agents. As methylating agentsare concerned, two main mechanisms have beenenvisaged. One involves the O6-methylguanine-DNA-methyltransferase (hAGT), which removes themethyl/alkyl group from the O6 position ofguanine. A second important mechanism is thebase excision repair (BER) pathway, which isinvolved in the repair of adducts resulting frommethylation of the N7 position of guanine (N7-mG)s. The objective of this project is thedevelopment of potent inhibitors of hAGT andAPE1, a key endonuclease in the BER pathway. Tothis end, a combination of X-ray crystallographyand in silico virtual screening of chemical librariesis being used. This research line of the group issupervised by Dr. Carme Fàbrega.


The main objectives of the group are the study ofsurfactant self-aggregation processes to contributein the development of nanotechnologicalapplications. The knowledge on basic aspects ofsurfactant aggregates (micelles, liquid crystals,vesicles) and colloidal dispersions (microemulsions,nano-emulsions, etc.) allows their use asnanoreactors for the preparation of novelnanostructured materials and as controlled drugdelivery systems.

STAFFCONXITA SOLANS MARSÀ, GROUP LEADER NURIA AZEMAR SAZATORNIL

TECHNICIANAMALIA VÍLCHEZ FERNÁNDEZ

Ph. D.GABRIELA CALDERÓ LINNHOFF CARLOS RODRÍGUEZ ABREUGOUTAM GHOSHROLAND RAMSCHALESSANDRO PATTILACRAMIOARA ZADOINAMARTÍN RABELERO

Ph. D. STUDENTSCAROLINA AUBERY TORRESMARIA DEL CARMEN LENDÍNEZ GRISMERITXELL LLINÀS PONSJORDI NOLLA ANGUERANEUS VILANOVA GARCÍASILVIA VILCHEZ MALDONADOSTEFANIE LEITNERKELLY LIDIA PEMARTINCAMILLE PAULMECRISTINA FORNAGUERA

POST-GRADUATE STUDENTSMARÍA HOMS SAN MILLÁNLAURA SOBREVIAS

Colloid and Interfacial Chemistry Group

57


Surface and self-aggregation properties of bis-benzimidazolones derivatives of D-glucose. Lakhrissi, B., Lakhrissi, L., Massoui, M., Essassi,E.M., Comelles, F., Esquena, J., Solans, C.,Rodríguez-Abreu, C. J. Surfactants Deterg.13 329-338, 2010Use of hydrophobically modified inulin for thepreparation of polymethyl methacrylate/polybutyl acrylate latex particles using asemicontinuous reactor.Obiols-Rabasa, M., Ramos, J., Forcada, J.,Esquena, J., Solans, C., Levecke, B., Booten, K.,Tadros, T.F. Langmuir 26 7717-7724, 2010Studies on controlled release of hydrophilicdrugs from W/O high internal phase ratioemulsions.Calderó, G., Llinàs, M., García-Celma, M.J.,Solans, C. J. Pharm. Sci. 99 701-711, 2010Nonaqueous foam with outstanding stabilityin diglycerol monomyristate/olive oil system. Shrestha, R.G., Shrestha, L.K., Solans, C.,Gonzalez, C., Aramaki, K. Colloid Surf. A-Physicochem. Eng. Asp. 353 157-165, 2010

Solution behavior of aqueous mixtures of lowand high molecular weight hydrophobicamphiphiles.Rodríguez-Abreu, C., Sánchez-Domínguez, M.,Šarac, B., Bešter Rogac, M., Shrestha, R.G.,Shrestha, L.K., Varade, D., Ghosh, G., Aswal, V.K.Colloid Polym. Sci. 288, 923-935, 2010. Erratumto 288 739-751.Nano-emulsions prepared by the phaseinversion composition method: Preparationvariables and scale up.Solè, I., Pey, C.M., Maestro, A., González, C.,Porras, M., Solans, C., Gutiérrez, J.M.J. Colloid Interface Sci. 344 417-423, 2010Effect of alkyl chain asymmetry on catanionicmixtures of hydrogenated and fluorinatedsurfactants.Blanco, E., Rodríguez-Abreu, C., Schulz, P., Ruso,J.M.J. Colloid Interface Sci. 341, 261-266, 2010Synthesis of CeO2, ZrO2, Ce0.5Zr0.5O2, andTiO2 nanoparticles by a novel oil-in-watermicroemulsion reaction method and their useas catalyst support for CO oxidation.Sánchez-Domínguez, M., Liotta, L.F., Di Carlo, G.,Pantaleo, G., Venecia, A.M., Solans, C.,Boutonnet, M. Catal. Today 158, 35-46, 2010


58

Current-voltage characteristic of electrosprayprocesses in microfluidics.Gundabala, V.R., Vilanova, N., Fernández-Nieves, A.Phys. Rev. Lett. 105, 154503, 2010Preparation of ultra-light magneticnanocomposites using highly concentratedemulsions.Ghosh, G., Vilchez, A., Esquena, J., Solans, C.,Rodríguez-Abreu, C. Mater. Chem. Phys. 130 786-793, 2011Formation of polymeric nano-emulsions by alow-energy method and their use fornanoparticle preparation.Calderó, G., García-Celma, M.J., Solans, C. J. Colloid Interf. Sci. 353 406-411, 2011A combination of hard and soft templatingfor the fabrication of silica hollow microcoilswith nanostructured walls.Rodriguez-Abreu, C., Vilanova, N., Solans, C.,Ujihara, M., Imae, T., López-Quintela, A.,Motojima, S. Nanoscale Res. Lett. 6 330-337, 2011Surfactants based on bis-galactobenzimidazolones: Synthesis, self-assembly and ion sensing properties.Lakhrissi, L., Hassan, N., Lakhrissi, B., Massoui,M., Essassi, E.M., Ruso, J.M., Solans, C.,Rodriguez-Abreu, C.J. Surfactants Deterg. 14 487-495, 2011Surface versus volume effects in luminescentceria nanocrystals synthesized by an oil-in-water microemulsion method.Tiseanu, C., Parvulescu, V.I., Boutonnet, M.,Cojocaru, B., Primus, P.A., Teodorescu, C.M.,Solans C., Sánchez Domínguez, M.Phys. Chem. Chem. Phys. 13 17135-17145, 2011Chromonic liquid crystalline phases ofpinacyanol acetate: Characterization and useas templates for the preparation ofmesoporous silica nanofibers.Rodríguez-Abreu, C., Torres, C.A., Tiddy, G.J.T.Langmuir, 27 3067-3073, 2011Identification and characterization of organicnanoparticles in food.Peters, R., Dam, G.T., Bouwmeester, H., Helsper,H., Weigel, S., Allmaier, G., vd Kammer, F.,Ramsch, R., Solans, C., Tomaniová, M., Hajslova, J.TrAC-Trend. Anal. Chem. 30 100-112, 2011Influence of a mixed ionic/nonionic surfactantsystem and the emulsification process on theproperties of paraffin emulsions.Vilasau, J., Solans, C., Gómez, M.J., Dabrio, J.,Mújika-Garai, R., Esquena, J.Colloid Surf. A-Physicochem. Eng. Asp. 392, 38-44, 2011

Phase behaviour of a mixed ionic/nonionicsurfactant system used to prepare stable oil-in-water paraffin emulsions.Vilasau, J., Solans, C., Gómez, M.J., Dabrio, J.,Mújika-Garai, R., Esquena, J.Colloid Surf. A-Physicochem. Eng. Asp. 384 473-481, 2011Stability of oil-in-water paraffin emulsionsprepared in a mixed ionic/nonionic surfactantsystem.Vilasau, J., Solans, C., Gómez, M.J., Dabrio, J.,Mújika-Garai, R., Esquena, J.Colloid Surf. A-Physicochem. Eng. Asp. 389 222-229, 2011Synthesis of Pt nanoparticles in oil-in-watermicroemulsions: Phase behavior and effect offormulation parameters on nanoparticlecharacteristics.Sánchez-Domínguez, M., Koleilat, H., Boutonnet,M., Solans, C.J. Disp. Sci. Tech. 32 1765-1770, 2011Characterization of perylene diimide dye self-assemblies and their use as templates forthe synthesis of hybrid and supermicroporousnanotubules.Rodríguez Abreu, C.; Aubery, C.; Solans, C.;López-Quintela, M. A.; Tiddy, G.ACS Appl. Mater. Interfaces 3 4133–4141, 2011Tuning high aqueous phase uptake innonionic water-in-oil microemulsions for thesynthesis of Mn-Zn ferrite nanoparticles:Phase behavior, characterization, andnanoparticle synthesis.Aubery, C., Solans, C., Sánchez-Domínguez, M.Langmuir 27 14005-14013, 2011Relaxation dynamics in the columnar liquidcrystal phase of hard platelets.Patti, A., Belli, S., van Roij, R., Dijkstra, M.Soft Matter 7 3533-3545, 2011Polydispersity stabilizes biaxial nematic liquidcrystals.Belli, S., Patti, A., Dijkstra, M., van Roij, R.Phys. Rev. Lett. 107 148303, 2011Spectrally and temporarily resolvedluminescence study of short-range order innanostructured amorphous ZrO2.Tiseanu, C., Parvulescu, V.I., Sanchez-Dominguez,M., Boutonnet, M.J. Appl. Phys. 110 103521, 2011Reference materials for measuring the size ofnanoparticles.Linsinger, T.P.J., Roebben, G., Solans, C., Ramsch, R.TrAC- Trend. Anal. Chem. 30 19-27, 2011


Maestro, A., Nolla, J., González, C., Gutiérrez, J.M.Worm-like micelles in diluted mixedsurfactant solutions: Formation andrheological behavior. in Self-organized surfactants (ed. T.F. Tadros) Wiley-VCH, Weinheim, Germany. 239-257, 2010Rodríguez-Abreu, C., Esquena, J.Preparation mesoporous materials withnonhydrocarbon surfactants.in Self-organized surfactants (ed. T.F. Tadros) Wiley-VCH, Weinheim, Germany. 213-216, 2010

Ghosh, G., Vílchez, A., Esquena, J., Solans, C.,Rodríguez-Abreu, C. Preparation of porous magneticnanocomposite materials using highlyconcentrated emulsions as templates. in Trends in Colloid and Interface Science XXIV(eds V. Starov, K. Procházka). Progress in Colloidand Polymer Science, Vol. 138 161-164, 2011.Springer.


59

Amphiphile self-assemblySelf-assembly studies of amphiphilic molecules areconducted in the group as a bottom up approachfor the development of well-defined nanostructuresin view of their use as nanocarriers (e.g. controlleddrug delivery systems), nanoreactors (e.g. synthesisof advanced materials), tailor-made formulations,etc. During this period, the self-organizing structuresformed by a water soluble perylene diimide dye (PDI)have been studied as potential templates for thepreparation of hybrid nanomaterials (C. RodríguezAbreu, ACS Appl. Mater. Interfaces, 2011). This PDIdye forms nematic and hexagonal chromonic liquidcrystals in water, consisting of stacks of longaggregates with a diameter close to the size of onePDI molecule (Figure 1).

Figure 1. Schematics of the proposed structure for perylenediimide dye (PDI) aggregates and how they are affected bytemperature.

The use of π-π stacked chromonic aggregatesbrings new possibilities for the template fabricationof pores with sizes below the mesoporous range.The obtained materials could find applications inphotovoltaics as well as in shape selective catalysisand adsorption.Self-assembly properties of sugar-derived surfactants,such as new nonionic amphiphiles based onbis-galactobenzimidazolones, have also beeninvestigated. These surfactants were synthesized bygrafting alkyl bis-benzimidazolones units ashydrophobic tail on hydroxypropyloxygalacto-pyranose moiety as hydrophilic moiety (B. Lakhrissi, J.Surfactants Deterg., 2011) Evaluation of self-aggregation properties in water showed very low

critical micellar concentrations (CMCs) and theformation of hexagonal liquid crystals for a certainrange of hydrophobic tail lengths. Furthermore, thenew amphiphiles showed characteristic UV-visabsorption and fluorescence emission bandsassociated with the benzimidazolone moiety. Allthese properties make these new amphiphilesappropriate candidates as self-assemblingchemosensors.

Emulsions: Formation by low-energy methodsand propertiesEmulsification by low-energy methods produce,generally, emulsions with smaller and moreuniform droplets. New knowledge on low-energyemulsification methods has been acquired bystudying nano-emulsion formation in systems witha polar solvent containing a preformed polymer asdispersed oil phase. Polymeric O/W nano-emulsions with size below 100 nm were obtainedby the phase inversion composition (PIC) methodusing a non-toxic solvent (G. Calderó, J ColloidInterface Sci., 2011). Conductivity measurementsperformed along dilution paths of mixtures withdifferent oil-to-surfactant (O/S) ratios confirmedthat nano-emulsions were produced by phaseinversion (Figure 2).

Figure 2. Conductivity as a function of water content in thewater/polyoxyethylene 4 sorbitan monolaurate/ethylcelulose-ethyl acetate system. O/S : Oil to surfactant ratio

The results of this study showed that the low-energy emulsification methods are not only validfor aliphatic and semipolar oils, but also for a highlypolar solvent such as ethylacetate containing apreformed polymer.

Research highlights


Other research lines developed in the field ofemulsions by the group deal with the study of drugrelease from highly concentrated emulsions (G.Calderó, J. Pharm. Sci., 2010) and on the use ofthese emulsions as templates for the preparation ofultralight porous materials (G. Ghosh, Mater. Chem.Phys., 2011). Biocompatible highly concentratedwater-in-oil (W/O) emulsions suitable for cutaneousand transdermal administration of drugs weresusccesfully prepared (Figure 3). To study the factorsinfluencing drug release, two model drugs,clindamycin hydrochloride and theophylline, withdifferent characteristics (chemical nature, molecularweight, water solubility, acid-base dissociation)were selected and incorporated in the dispersedphase of the emulsions.

Figure 3. Region of formation of highly concentrated emul-sions (striped area) at 25ºC in the systems: (a)water/Cremophor WO7/soybean oil and, (b)water/Cremophor WO7/liquid paraffin.

The release of clindamycin hydrochloride, which isfreely soluble in water, was very slow, regardless ofthe emulsion system, while the release oftheophylline, which is slightly soluble in water, wasfaster. By changing the pH of the dispersed phaseof highly concentrated emulsions, which in turnaffects solubility, drug release could be modulated.These results suggested that with freely solubledrugs, the solubility, rather than interfacialproperties of the emulsion system, is the mainfactor controlling its release. In contrast withslightly soluble drugs, release can be controlled bythe interfacial properties of the HIPRE and byinducing solubility changes in the drug. The knowledge on the use of highly concentratedemulsions as templates for the preparation ofporous materials was applied to obtain hybridmagnetic nanocomposite materials. These materialswere prepared by polymerization in the continuousoil phase of styrene-divinylbenzene mixturesincorporating magnetite (Fe3O4) nanoparticles.Ultra-light porous nanocomposites were obtainedwith the nanoparticles distributed homogeneouly inthe polymer walls (Figure 4) giving a uniformmagnetic moment over the entire material.

Figure 4. Solid foams (porous nanocomposites) with mag-netic nanoparticles of 3 nm. Images by scanning (top) andtransmission (bottom) electron microscopy.

These materials are about 20 times lighter than thenon-porous nanocomposite material with similarmagnetic properties (superparamagnetic behaviour),and stronger particle-particle interaction.

The Microemulsion Reaction MethodAmong wet chemistry methods for the synthesis ofinorganic nanoparticles, the MicroemulsionReaction Method (MRM) has been found to be asuitable option in order to control size and shapein mild reaction conditions. In this context, theformation of w/o microemulsions with highaqueous phase uptake in a nonionic surfactantsystem was investigated as potential media for thesynthesis of magnetic nanoparticles (C. Aubery,Langmuir, 2011). Three microemulsions with threedifferent dynamic behavior (non-percolated andpercolated w/o, as well as bicontinuousmicroemulsions) were selected for the synthesis ofMn-Zn ferrites (Figure 5). The aqueous phasecontent ranged from 5 wt% to 50 wt%.

Figure 5. Microemulsion region in an aqueous solu-tion/surfactant/oil system and TEM images of Mn-Zn ferritenanoparticles obtained in microemulsions with differentdynamic behavior

Differences were observed in the characteristics ofthe synthesized nanoparticles depending on thetype of microemulsions used, and in all cases spinelnanocrystalline particles with superparamagneticproperties were obtained, directly in themicroemulsion, without the need for calcination. A novel approach based on the use of O/W insteadof W/O microemulsions for the synthesis ofinorganic nanoparticles has been developed in thegroup since our first report on the subject in 2009.The synthesis of metallic (Pt, Pd, and Rh) as well asmetal oxide (CeO2) nanoparticles were firstreported as a proof of concept of the O/Wmicroemulsion reaction method. It was followed bythe synthesis of mesoporous nanocrystalline oxidessuch as ZrO2, Ce0.5Zr0.5O2, and TiO2 (M. Sanchez-Dominguez, Catalysis Today, 2010). Small particlesize (3 nm), and high specific surface area (200-380m2 g-1) was obtained for all materials. Thematerials were evaluated as catalyst supports in theCO oxidation reaction and showed a good activityin CO oxidation at low temperature.

60


61

STAFFÁNGEL MESSEGUER PEYPOCH, GROUP LEADER FRANCISCA REIG ISART

Ph. D.ASUNCIÓN BURGUETE PÉREZ ESTHER CARRASCO ROMERO NATALIA DE LA FIGUERAFEDERICO RUA

TECHNICIANSCRISTIAN LASTRE

Ph. D. STUDENTSMIRIAM CORREDOR SÁNCHEZ GLORIA NAVARRO-VENDRELL LAURA VÁZQUEZMIQUEL VIDAL MOSQUERA


Protein-protein interaction antagonists asnovel inhibitors of non-canonicalpolyubiquitylation. Scheper, J., Guerra-Rebollo, M., Sanclimens, G.,Moure, A., Masip, I., González-Ruiz, D., Rubio,N., Crosas, B., Meca-Cortés, O., Loukili, N., Plans,V., Morreale, A., Blanco, J., Ortiz, A.R.,Messeguer, A., Thomson, T.M. PLoS ONE 5 e11403, 2010Peptoids bearing tertiary amino residues inthe n-alkyl side chains: synthesis of a potentinhibitor of Semaphorin 3A. Messeguer, J., Masip, I., Montolio, M., del Rio,J.A., Soriano, E., Messeguer, A. Tetrahedron 66 2444-2454, 2010Nanoconjugates as intracorporeal neutralizersof bacterial endotoxins. Vicent, M.J., Cascales, L., Carbajo, R.J., Cortés,N., Messeguer, A., Pérez Payá, E. J. Control. Release 142 277-285, 2010Antioxidant CR-6 protects against reperfusioninjury after a transient episode of focal brainischemia in rats.Pérez-Asensio, F.J., De La Rosa, X., Jiménez-Altayó, F., Gorina, R., Martínez, E., Messeguer, A.,Vila, E., Chamorro, A., Planas, A.M. J. Cerebr. Blood Flow Met. 30 638-652, 2010A fluorescent polarization-based assay for the identification of disruptors of the RCAN1-calcineurin A protein complex. Mulero, M.C., Orzáez, M., Messeguer, J.,Messeguer, A., Pérez-Payá, E., Pérez-Riba, M. Anal. Biochem. 398 99-103, 2010

Triazine-based vanilloid 1 receptor openchannel blockers: Design, synthesis,evaluation, and SAR analysis.Vidal-Mosquera, M., Fernández-Carvajal, A.,Moure, A., Valente, P., Planells-Cases, R.,González-Ros, J.M., Bujons, J., Günther, U.L.,Reed, M.A., Ciudad, C.J., Torres, J.L., Messeguer, A. J. Med. Chem. 54 7441-7452, 2011Chemical modulation of peptoids: Synthesisand conformational studies on partiallyconstrained derivatives.Moure, A., Sanclimens, G., Bujons, J., Masip, I.,Alvarez-Larena, A., Pérez-Payá, E., Alfonso, I.,Messeguer, A. Chem.-Eur. J. 17 7927-7939, 2011Molecules that modulate Apaf-1 activity.Pérez-Payá, E., Orzáez, M., Mondragón, L.,Wolan, D., Wells, J.A., Messeguer, A., Vicent, M.J. Med. Res. Rev. 31 649-675, 2011A novel free radical scavenger rescues retinalcells in vivo.O'Driscoll, C., Doonan, F., Sanvicens, N.,Messeguer, A., Cotter, T.G. Exp. Eye Res. 93 65-74, 2011Improved therapeutic responses for liposomaldoxorubicin targeted via thrombospondinpeptidomimetics versus untargeteddoxorubicin.Rivera-Fillat, M.P., Reig, F., Martínez, E.M., Grau-Oliete, M.R.J. Pept. Sci. 16 315-321, 2010

Bioorganic Chemistry GroupWe use the modern medicinal chemistrytechniques (combinatorial chemistry, in silicodesign and construction of chemical libraries, solidphase synthesis, drug delivery methods) for theidentification of hit compounds against targets ofpharmacological interest. Complementarily, thechemical modulation of these hits for theirconversion into lead compounds for furtherdevelopment in collaboration with pharma andbiotech companies is intensively pursued. Thegroup has filed four patent applications in 2010-2011 and licensed one patent to a biotechcompany.


Potential implication of aniline derivatives inthe Toxic Oil Syndrome (TOS).Messeguer, A. Chem.-Biol. Interact. 192 136-141, 2011Messeguer, A.Els químics i el descobriment de fàrmacs: unrepte i una necessitat.Educació Química: EduQ. 5 4-10, 2010.Messeguer, A.La Comissió Lexicogràfica de Ciències. Un record encara viu.Terminàlia 4 70-71, 2011.

Publications (books and book chapters) Mondragón, L., Orzáez, M., Gortat, A., Sancho,M., Messeguer, A., Vicent, M.J., Pérez-Payá, E. Molecules that Bind a Central ProteinComponent of the Apoptosome, Apaf-1, andModulate its Activity.in Apoptosome: An-up-and-coming therapeuticaltool (eds. F. Cecconi, M. D'Amelio), Ch 4, 75-94,2010Springer (Springer Science+Business Media)ISBN 978-90-481-3414-4. Messeguer, A.Fronteras del Conocimiento Actual enQuímica.in Física y Química. Complementos de formacióndisciplinar (Caamaño, A. coord.). Ch 5, 89-100,2011 "Materiales para la formación delprofesorado de la Educación Secundaria" EditorialGraó

62

Concerning combinatorial chemistry in drugdiscovery, our group became interested in this fieldin 1998. Through the establishment ofcollaborative projects with different laboratories,the group has been pioneer in Spain in the designand construction of combinatorial libraries oforganic molecules, in particular of libraries ofcontrolled mixtures of small organic molecules. Inthis period, libraries of peptoid mixtures (5.000 and11.000 N-alkylglycine trimers, and 625 pentamers,respectively) and four libraries of individualcomponents (peptidomimetics bearing heterocyclicmoieties) have been prepared. In addition, librariesof peptidomimetics attached to microplates (ChemChips) have been also constructed.

Along this period, our group has incorporated therequired expertise for handling the differentmethodologies to work on Combichem (solid-phase organic synthesis, synthesis of libraries insolution, libraries of individuals or mixtures, use ofmicrowave activation of organic reactions, in silicomethodology for the design and screening ofvirtual libraries etc.). By using this general strategy,our group has obtained highly interesting results.Thus, we identified two peptoids that exhibit highin vitro and in vivo activity as blockers of the TRPV1vanilloid receptor. In addition, and also incollaboration with the same partners, we identifieda family of molecules exhibiting potent antagonistactivity against the NMDA receptor. Moreover, theidentification of a peptoid capable of inhibitingSema-3 and thus interesting for studying theaxonal regeneration problem, has been recentlyachieved.

More recently, in collaboration with the group ofDr. E. Pérez-Payá (CIPF, Valencia), two compoundsthat neutralise bacterial endotoxins have been

identified. In a parallel study in collaboration withthe same group, peptoids capable of inhibiting theformation of apoptosome have been discovered.These compounds have been intellectuallyprotected and the patent has been licensed to apharmaceutical company for co-development. Thisresult represents the first example of a smallmolecule as inhibitor of apoptosis operating by thismechanism and it also constitutes an interestingexample of how small molecules can perturb andeven modulate protein-protein interactions. Afurther conversion of the initial hit into apeptidomimetic exhibiting improved activities invitro and in vivo has been also carried out. The co-development of this compound in the organtransplant field is currently under contractedresearch with the above pharmaceutical company.

In a collaboration established with the group of Dr.Timothy Thomson (IMBM-CSIC, Barcelona), we havealso identified peptoids capable of perturbingprotein-protein interactions (UBC13-UEV) of interestin cancer and inflammation. What is interesting ofthis example and of some other commented above(for instance, the inhibitor of apoptosome), is thatwe have done already a step ahead in order toconvert the identified hits into compoundsexhibiting more friendly pharmacological profiles.Our goal is the selection of a lead candidate.

This structural conversion has been carried out byan initial study of the conformational preferencesof the peptoid skeleton followed by the design ofconformationally restricted analogues bearingdifferent types of heterocyclic scaffolds. At thismoment, we have one peptidomimetic showinghigh inhibitory activity of the apoptosome in intactcells. Moreover, a new generation of apoptosisinhibitors bearing a novel heterocyclic skeleton,

Research highlights


63

already patented, has been also developed.Likewise, two peptidomimetics have beenprepared following a molecular modelling study forimproving the properties of the initial hitdiscovered in the above commented modulation ofUBC13-UEV interaction. It should be remarked thatthis discovery represents the development of thefirst modulators of this protein-protein interactionthat can show a highly promising activity in cancertreatment. Finally, our group has also beeninterested in expanding the expertise ofexperimental combinatorial libraries to thosedesigned and screened in silico.

Our work on compounds that exhibit bioactiveactivity has been complemented by research on freeradicals quenchers, either from oxygen (ROS) and/ornitrogen (RNS). Some years ago we discovered atocopherol surrogate (CR-6) bearing a simplestructure and potent activity as lipid peroxidationinhibitor. More recently, its activity as inhibitor ofRNS species (NO and peroxynitrite) was also shown.Our laboratory participates with a biotech company,the Lipotec Group, in the industrial development ofthis antioxidant. This compound is now in Phase IIclinical trials in antitumour therapy, specifically inpreparations containing liposomes that encapsulatedoxorubicin. CR-6 is embedded in these liposomesand reduces the side-effects produced by theanticancer drug. Moreover, CR-6 is beingcommercially used in the dermopharmacy area asantiageing agent. On the other hand, recent workhas shown the ability of CR-6 to inhibit apoptosis in

photoreceptor cells (collaboration with T. Cotter,Univ. of Cork, Ireland). Likewise, in a collaborationestablished with the group of A. Planas (IIBB-CSIC,Barcelona), very interesting results on the potentialneuroprotective activity of CR-6 have beenobtained.

Taken together, all these results show the hightherapeutic potential of this radical inhibitor.Currently, we are working on analogues capable ofeliciting a higher penetration through the bloodbrain barrier. In parallel, physicochemical studiesconcerning interactions between this compoundand phospholipids have been performed in orderto know how the molecules insert and locate in thebilayers.

Finally, it is worth of mentioning the intense activityof our group in two additional fields. First, we aremembers of a Consolider Consortium focused onIon Channels and financed up to 2013 andcoordinated by Prof. Antonio Ferrer-Montiel (Univ.Miguel Hernández). Our main task is to providewith molecules (libraries or individuals) to morethan 20 research groups working on ion channelsand interested in the identification of compoundsthat can modulate the function of these channels.On the other hand, our group is workingintensively in two research projects supported byprivate pharma or biotech companies. In bothcases it is intended to discover lead compoundsactive in front of highly interesting pharmaceuticaltargets.


The main objective is to study the formation andcharacterization of structured materials, and theirapplications in novel technological processes. Thisincludes: a) Surface modification of materials bychemical and physical (plasma) methods, b) Surfacecharacterization of textile and polymeric materials,c) Formation and characterization of hydrogels, d)Development of stimuli-responsive textiles byincorporation of advanced nanostructuredmaterials, and e) Preparation and characterizationof organic and inorganic porous materials.

STAFFJORDI ESQUENA MORET, GROUP LEADER RICARDO MOLINA MANSILLA PILAR ERRA SERRABASA, AD HONOREM SENIORRESEARCHER

Ph. D.MARC OBIOLS RABASALOURDES ADRIANA PEREZ CARRILLO SUSANA VÍLCHEZ MALDONADO ISABEL SOLÈ FONTMOHAHMAD MYDUL ALAM

Ph. D. STUDENTSMARÍA MARTÍNEZ RODRÍGUEZ JONATHAN MIRAS HERNÁNDEZ MANROSHAN SINGHJON VILASAU SAROBE ALEJANDRO VÍLCHEZ VILLALBA SILVIA VILCHEZ MALDONADO

Surface Chemistry Group

64


Improved properties of oxygen and argon RFplasma-activated polyester fabrics loadedwith TiO2 nanoparticles.Mihailovic, D., Saponjic, Z., Molina, R., Puac, N.,Jovancic, P., Nedeljkovic, J., Radetic, M.ACS Appl. Mater. Interfaces 2 1700-1706, 2010Surface and self-aggregation properties ofbis-benzimidazolones derivatives of D-glucose. Lakhrissi, B., Lakhrissi, L., Massoui, M., Essassi,E.M., Comelles, F., Esquena, J., Solans, C.,Rodríguez-Abreu, C. J. Surfact. Deterg. 13 329-338, 2010Use of hydrophobically modified inulin for thepreparation of polymethylmethacrylate/polybutyl acrylate latex particlesusing a semicontinuous reactor.Obiols-Rabasa, M., Ramos, J., Forcada, J.,Esquena, J., Solans, C., Levecke, B., Booten, K.,Tadros, T.F. Langmuir 26 7717-7724, 2010A liquid-crystalline single-molecule magnetwith variable magnetic properties.Gonidec, M., Luis, F., Vilchez, À., Esquena, J.,Amabilino, D.B., Veciana, J. Angew. Chem. Int. Edit. 49 1623-1626, 2010

Interfacial processes in textile materials:Relevance to adhesion.Molina, R., Esquena, J., Erra, P. J. Adhes. Sci. Technol. 24 7-33, 2010Influence of chitosan on the effects ofproteases on wool fibers.Vílchez, S., Jovan i , P., Erra. P.Fiber. Polym. 11 28-35, 2010Nano-emulsions prepared by the phaseinversion composition method: Preparationvariables and scale up.Solè, I., Pey, C.M., Maestro, A., González, C.,Porras, M., Solans, C., Gutiérrez, J.M.J. Colloid Interf. Sci. 344 417-423, 2010Preparation of ultra-light magneticnanocomposites using highly concentratedemulsions.Ghosh, G., Vilchez, A., Esquena, J., Solans, C.,Rodríguez-Abreu, C. Mater. Chem. Phys. 130 786-793, 2011Aqueous phase behaviour of cholinecarboxylate surfactants-exceptional varietyand extent of cubic phases.Klein, R., Tiddy, G.J.T., Maurer, E., Touraud, D.,Esquena, J., Tache, O., Kunz, W. Soft Matter 7 6973-6983, 2011


65

Multifunctional properties of polyester fabricsmodified by corona discharge/air RF plasmaand colloidal TiO2 nanoparticles. Mihailovic, D., Šaponjic, Z., Molina, R., Radoicic,M., Esquena, J., Jovancic, P., Nedeljkovic, J.,Radetic, M. Polym. Compos. 32 390-397, 2011Macroporous polymers obtained in highlyconcentrated emulsions stabilized solely withmagnetic nanoparticles. Vílchez, A., Rodríguez-Abreu, C., Esquena, J.,Menner, A, Bismarck, A.Langmuir 27 13342-13352, 2011Influence of a mixed ionic/nonionic surfactantsystem and the emulsification process on theproperties of paraffin emulsions. Vilasau, J., Solans, C., Gómez, M.J., Dabrio, J.,Mújika-Garai, R., Esquena, J. Colloid Surf. A-Physicochem. Eng. Asp. 392 38-44, 2011Novel properties of PES fabrics modified bycorona discharge and colloidal TiO2nanoparticles. Mihailovic, D., Šaponjic, Z., Radoicic, M., Molina, R., Radetic, T., Jovancic, P., Nedeljkovic, J.,Radetic, M. Polym. Advan. Technol. 22 703–709, 2011Modifying the heat transfer and capillarypressure of loop heat pipe wicks with carbonnanotubes.Terrado, E., Molina, R., Natividad, E., Castro, M.,Erra, P., Mishkinis, D., Torres, A., Martínez, M.T.J. Phys. Chem. C 115 9312–9319, 2011

Stability of oil-in-water paraffin emulsionsprepared in a mixed ionic/nonionic surfactantsystem.Vilasau, J., Solans, C., Gómez, M.J., Dabrio, J.,Mújika-Garai, R., Esquena, J.Colloid Surf. A-Physicochem. Eng. Asp. 389 222-229, 2011Phase behaviour of a mixed ionic/nonionicsurfactant system used to prepare stable oil-in-water paraffin emulsions.Vilasau, J., Solans, C., Gómez, M.J., Dabrio, J.,Mújika-Garai, R., Esquena, J.Colloid Surf. A-Physicochem. Eng. Asp. 384 473-481 2011

Publications (books and book chapters)Rodríguez-Abreu, C., Esquena, J. Preparation of Mesoporous Materials withNonhydrocarbon Surfactants,in Self-Organized Surfactant Structures (ed T. F.Tadros). Ch 11, 213-238, 2010Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim,Germany. doi:10.1002/9783527632633. Ghosh, G., Vílchez, A., Esquena, J., Solans, C.,Rodríguez-Abreu, C.Preparation of porous magneticnanocomposite materials using highlyconcentrated emulsions as templates.in Trends in Colloid and Interface Science XXIV(eds V. Starov, K. Procházka). Progress in Colloidand Polymer Science, Vol. 138, 161-164, 2011Springer. ISBN 978-3-642-19037-7

Pickering emulsions as templates for thepreparation of macroporous solid foamsHighly concentrated emulsions (HIPEs) arecharacterized by possessing a volume fraction ofthe disperse phase that exceeds 0.74, whichcorresponds to the critical value for the mostcompact packing of monodisperse sphericaldroplets. HIPEs can be used as templates for thepreparation of macroporous materials via thepolymerization of the external emulsion phase.

Macroporous polymer foams with a magneticresponse have been prepared by taking advantage ofthe ability of the nanoparticles to stabilize emulsions(which are typically denoted as Pickering emulsions).In analogy with surfactants, nanoparticles can besurface active, and adsorb spontaneously at the oil-water interfaces. One of the advantages of usingparticle-stabilized emulsions is that any additionalproperty coming from the nanoparticle can bedirectly imparted to the materials.

Solid foams with up to 95% of porosity, and highmagnetization saturation values resulting from theFe3O4 nanoparticles have been obtained. Asshown in Fig.1 such nanoparticles are located atthe polymer-air interface after the polymerization.These magnetic macroporous materials could actas promising adsorbents for specific molecules orbe used in water decontamination process.

Fig.1. SEM (left) and TEM (right) images of a macroporoussolid foam with micrometer pore sizes and Fe3O4 nanopar-ticles placed at the polymer-air interface. Vílchez, A.,Rodríguez-Abreu, C., Esquena, J., Menner, A., Bismarck, A.Langmuir 2011, 27, 13342.

Research highlights


Use of plasma for advanced technologiesPlasma is generated when a gas is exposed to anelectric field, generating radicals, ions, electronsand other excited species of high energy. Thesereactive species can interact either physically orchemically with the substrate surface to a depth ofa few tenths of nanometers.

As a result of plasma treatment, the surface may befunctionalized (by the generation of new chemicalgroups), and/or degraded as a result of the etchingeffect (removal of surface material), whereas thebulk properties remain intact. Attending to the typeof plasma gas, these effects are used in polymersurface modification in order to improve surfaceproperties such as adhesion, wetting (hydrophilicity/hydrophobicity), incorporate reactive groups suchas carboxylic or amine groups and/or thin filmdeposition by plasma polymerization. Thecombination of both, high energy reactive speciesand ultraviolet radiation generated in the plasma isalso used for bacteria or spore sterilization, at lowtemperature.

Fig. 2. Plasma treatment of an aqueous solution on a dielec-tric barrier discharge plasma reactor.

Whereas the low pressure plasma is a very wellknown technology, atmospheric plasma hasgrowing interest since no vacuum systems areinvolve and continuous process can be carried out.In this context, electrical discharges in and incontact with liquids (Figure 2) generate UVradiation, shock waves and very active chemicalgroups or atoms (OH, O, H2O2, etc) than canpromote oxidation, degradation and monomerpolymerization processes.

Atmospheric plasma can be applied to aqueoussolutions with monomers or polymers in order toobtain hydrogels or films with specific properties.Experimental parameters such as monomerconcentration and plasma power plays animportant role in the properties of the filmobtained. In this context, thin polymeric films withstimuli response properties can be obtained.Chitosan biopolymer films obtained by means ofatmospheric plasma treatment are less soluble inacid medium than conventional chitosan filmssuggesting that crosslinking reactions betweenpolymer chains can occur during the plasmatreatment.

On the other hand, plasma treatments have beencarried out in waste-water in order to eliminatechemical compounds such as dyes or pharmaceuticalproducts.

Textiles modified with chitosan hydrogels formedical and/or therapeutical applicationsNowadays, there is an increasing demand fortextiles with advanced functionalities for medical,therapeutical and cosmetic applications. Theyallow the administration of active molecules in asimple and controlled manner. Most of them arebased on the physical immobilization orimpregnation of textile fibers by a thin layer ofproducts containing active molecules. The releaseof the active molecules can be induced by thechemical degradation, via molecular diffusionprocesses, and/or as a response to an externalstimulus such as temperature, pH and ionicstrength. Hence, the use of hydrogels preparedfrom stimuli-responsive polymers, which displaychanges in solvatation in response to a change intemperature, pH and ionic strength, constitute aninteresting strategy to confer new properties totextiles. In this context, the biopolymer chitosan,which is a pH-sensitive polymer and responds to apH change by protonation/ deprotonation of itsamino groups, has been used to obtain hydrogelscrosslinked with the natural crosslinker genipin.

These hydrogels have been incorporated onto thesurface of polyamide fabrics by the paddingtechnique, and its successful incorporation wasconfirmed by cryoSEM (Fig.3). The waterabsorption ability of the treated fabrics was studiedthrough thermogravimetric dynamic vapoursorption (TG-DVS), which showed higher moisturecontent of fabrics, compared to untreated. Theporous structure of the fabrics was also studied by thermoporosimetry, which allows studying pore structures of materials in the presence ofwater.

Fig. 3. Cryo-scanning electron microscopy of hydrogel coa-ted polyamide fabric.

In a second step, active molecules have beensuccessfully incorporated in the hydrogel matrix, anddrug release studies have been performed (incollaboration with the Faculty of Pharmacy of theUniversity of Barcelona). In the case of hydrophilicactive molecules, the different release when theywere directly solubilized in the hydrogel or inliposomes contained in the hydrogel, has beenstudied (Fig. 2). On the other hand, hydrophobicactive molecules were solubilized in the lipidic bilayerof liposomes contained in the hydrogel. Thechemical interactions of the active molecules withthe chitosan hydrogel matrix have also been studied.

66


DEPARTMENT OF CHEMICAL AND SURFACTANTS TECHNOLOGY

5


DEPARTMENT OF CHEMICAL AND SURFACTANTS TECHNOLOGY

69

The research in the Department focus on theoretical and applied aspects of product andchemical processes technology with special incidence in the synthesis, the physical chemistryand the biology of surfactants. This research is relevant in the lines of Sustainable Chemistryand Nanotechnology of soft matter and look for environmental and human healthimprovement. Among the scientific activities, with relation to the Sustainable Chemistry,we can cite: research and development of biocompatible surfactants and ionic liquids, thedistribution and effect of surfactants and ionic liquids in the environment, development ofnon contaminant industrial processes, minimization, recycling and valorization of by-products and wastes of chemical industries. In the Nanotechnology area research isperformed concerning adsorption and self-aggregation of surfactant as well as the physicalchemistry and biophysics of natural lipids at interfaces and membranes (of natural originor as physical chemistry models).

Research groups Minimization of Industrial Wastes: Isolation of High Added-Value Biopolymers Development of Non-contaminant Industrial Processes Statistical Modelling and Fibre Physics Biocompatible Surfactants Environmental Chemistry of Surfactants and Ionic Liquids Physical Chemistry of Surfactant Systems Biophysics of Lipids and Interphases

Head: Ramon Pons Pons


The main objective of our research main line is thedesign and development of medical devices forskin tissue regeneration and/or improving tissuefunction based on as bioactive materials of naturalorigin. Animal waste from food: meat, fish, poultryindustries (slaughterhouse) and tanning industrieswill be used as raw material. Furthermore, thefollowing additional waste should be included: fishwaste, such as fish skins of hake, monkfish, soleand rock sole, and eggshell membrane. Of especialinterest is the possibility of extracting other high-added value products closely related to collagen,glycosaminoglycans (GAGs) (dermatan sulfate,keratan sulfate, etc.) mainly from the meat andpoultry industry (rooster combs, vitreous humour,synovial fluid) (5, 6) with hyaluronic acid as amaximum representative given its increasing use inmedicine. It is expected to develop new medicaldevices for the rapid healing of skin injuries (burns,ulcers, etc) that have not been resolved to date.Growing numbers of elderly people in Europesuffer from skin injuries such as bedsores andvascular ulcers and need effective medical devicesthat can be applied in hospitals and at home.

STAFFJAUME COT COSP, GROUP LEADERMERCHE CATALINA MARTÍNEZCLOSELY LINKED STAFFPERE CELMA SERRA (IQS-Associate Unit)JAUME CELMA SERRA (IQS-Associated Unit)

TAYLOR-MADE BIOMATERIALS FROMCOLLAGENIC WASTES: FEASIBLE LINKBETWEEN TANNING INDUSTRY AND TISSUEENGINEERINGThe environment is one of the most relevant topicsnowadays, the ecological conscience and thepractice of an environmentally friendly andsustainable policy is increasing day by day all overthe world. The concept of “SustainableDevelopment” transmits the idea of the rationaluse of the resources, the improvement of lifequality and the maintenance of the ecosystemswithout jeopardising future generations. Theimprovement of the manufacturing processes, thefinding of new types of renewable energies, theapplication of “clean” technologies in theprocessing, t the finding of new treatments foreach type of waste; are essential steps to makecompatible industrial development, environmental

protection and social welfare. Waste treatments, inaddition of reduce the volume of industrial wastecould increase their value through the productionof high added value products, entailing a greatprogress in both, environmental and economicalterms.

In terms of waste generation, the production ofleather gives rise to significant quantities of solidwaste product for which tanneries are responsiblefor the cost of disposal and since most of this wasteends up in landfill it may be considered anenvironmental problem. However such waste is notwithout some potential value since it containscollagen which could be recycled and reused.Collagen is a very versatile and special high-addedvalue protein and the most abundant andubiquitous in vertebrates. This collagenic nature ofthe tannery solid waste permits us to think about

Research highlights

Minimization of Industrial Wastes: Isolation of High Added-Value Biopolymers

70


Tailor-made biomaterials from collagenicwastes Catalina, M., Celma, P., Cot, J., Manich, A.,Marsal, A. J. Am. Leather Chem. As. 106 153-160, 2011Magnetically separable nanocomposites withphotocatalytic activity under visible light forthe selective transformation of biomass-derived platform molecules.Balu, A., Cot, J., Baruwati, B., Serrano, E., García-Martínez, J., Barma, S., Luque, R.Green Chem. 13 2750-2758, 2011

Influence of crosslinkers and crosslinkingmethod on the properties of gelatin filmsextracted from leather solid waste.Catalina, M., Attenburrow, G.E., Cot, J.,Covington, A.D., Antunes, A.P.M. J. Appl. Polym. Sci. 119 2105-2111, 2011Application of gelatin extracted from chromeshavings on the glazed finishing of leather.Catalina, M., Attenburrow, G.E., Cot, J.,Covington, A.D., Antunes, A.P.M.J. Am. Leather Chem. As. 105 138-144, 2010


71

treatments for obtaining biopolymers ofreconstituted collagen, and their use in a widerange of potential applications.

Up to now, “low cost” biomaterials have beenobtained. Their main applications have been: asfiller, re-tanning agents and finishing agents in thetanning industry itself; and as a binder in the paperindustry, partially substituting casein (much moreexpensive). The objective of the present work is theextraction, characterisation, optimisation andapplication of new “taylor-made” smartbiopolymers with high-added value, finding a newand feasible link between solid tannery waste andthe rising market of tissue engineering.

Tissue engineering can be defined as aninterdisciplinary field which applies, for one side,the principles of tissue engineering and, foranother side, the sciences of life, with the aim ofobtaining “Biological Structures” in order toregenerate and/or improve the tissue function.Although lots of synthetics biodegradable or bio-stable polymers have been employed on these“special structures”, the affinity of the graftedcellules is quite low. Biologically derived materialsare advantageous in that they contain informationthat facilitates cell attachment and function,whereas synthetics may not interact with cells inthe desired manner4. The importance and specialappeal of collagen as a biomaterial is based on thefact that collagen is a natural material andtherefore it is assimilated by the human/animalbody as a normal constituent and not as a foreignmaterial, subjected to rejection, with a minimum ofimmunogenicity. A great competitiveness ofreconstituted collagen fibres in the field ofregenerative medicine (tissues and/or organs) hasbeen found in literature.

Biopolymers are polymers generated fromrenewable resources, often biodegradable andfrom non-toxic production. They can be producedfrom biological systems or chemically synthesisedfrom biological raw materials. They are analternative to the petrol-based polymers. The mainproblems of biopolymers are bio-compatibility,mechanical properties and adaptability. Collagenicbiopolymers present huge possibilities due to thepossibility of manufacture, and application, indifferent ways, forms and shapes, with welldetermined characteristics. We can talk about“taylor-made” biopolymers: it is possible toproduce easily said biopolymers as gel, film, fibres,tissue and/or sponges, using techniques such asfreeze drying/lyophilisation, extrusion, or electro-spinning for nano-fibres formation.

In addition to the technical and scientific benefitsobtained from the isolation of biopolymers fromsolid waste, this research could entail differenteconomical benefits: In the first place, it presents asolution to a problem of dumping/storage ofwastes, avoiding taxes for accumulating those

wastes. Secondly, whole hides of low quality canbe used as raw material, those hides, cataloguedas a 4th-5th class, would be used to produce lowquality articles of very low price on the market;however, the biopolymer extracted from this hidewould have a high-added value.

Thirdly, the treatment process is simple and cheap;environmentally and economically much moreplausible than other treatments such asincineration, land-filling, etc. Finally, a wide rangeof potential applications for the produced bio-products could be taken into consideration; withspecific applications on medicine, veterinary and/orcosmetics, expanding field nowadays.

The technology to be used on the development ofthis research is focused on the production of macro-fibres (extrusion) and nano-fibres (electro-spinning),films, sponges (lyophilisation) and different types ofscaffold material for tissue engineering.

The use of mathematical experimental designspermits to study the degree of significance of thedifferent variables and the correspondinginteraction between them in the differentprocesses for obtaining collagenic biopolymers.This ensures that the experimentation can berationalised and the optimum determined, beingable to achieve a controlled production of “taylor-made” biopolymers for each specific application.

The versatile properties of collagen have madecollagenic biomaterials one of the most usefulmaterials for tissue engineering. Those biomaterialscan be in the form of and shape of natural tissue,porous scaffolds/sponges, fibres and gels.Reconstituted collagen fibres, and fibre networkshave been shown to be a competitive biomaterialfor soft and hard tissue replacement due to theiradvantageous properties. Those fibres have beenused as well as a suture material. It has beenpostulated that such fibres could be knitted orwoven into fabrics, although the production isdifficult due to the large amount of materialrequired. The traditional process for formation ofcollagen fibres involved the extrusion of collagendispersions into a fibre formation buffer andsubsequent solvent dehydration, air-drying andcross-linking.

Fig. 1 Collagenic biopolymer Fig. 2 Collagenic biopolymerextruded fibre. extruded fibre.

Collagen sponges are generally formed by freeze-drying an aqueous collagen solution. The freeze-drying process includes freezing a collagen gel


solution at a low temperature and subsequentsublimation of the ice crystals by vacuum at lowtemperature. The freezing temperature andfreezing rate will have some effect on the porousstructure of the resulting sponge.

Fig. 3 Collagenic biopolymer Fig. 4 Collagenic biopolymergel. film.

Fig. 5. Collagenic biopolymer sponge.

INDUSTRY IMPLEMENTATIONFigure 7 represents the diagram of the industrialplant for the extraction and purification ofcollagenic biopolymers of different molecularweight fractions from tannery solid wastes. Thebasic steps of the process are as follows:

- 1st Step _ Grinding up Bovine Hides: Driedpickle bovine hides are ground up (grinder: J-110)into defibered small size (0.25 mm) and therefore

giving a more homogeneous collagenic materialwith a greater surface, and consequently savingchemicals and shorten down the reaction time.Final product is impulsed through a pneumaticconveyor to the reactor.

- 2nd Step _ Production of collagenicbiopolymers: The biopolymer extraction, the mostimportant part of the whole process, is carried outin a stainless steel jacketed stirred reactor (R-120).The grounded hide is submitted to a mildcontrolled hydrolysis reaction; then, by means of apump (P-121) is driven to filter unit (S-125), wherethe suspension particles are separated from theviscous collagenic solution.

- 3rd Step _ Ultrafiltration: The ultrafiltration iscarried out by a combined sequentially connectedset of three membrane-based tangential flowfiltration spiral-wound modules of different cut-offranges: 1kDa (U-141); 50kDa (U-142) and 100kDa(U-143). In each one of these subunits, theretentate fraction feeds the next subunit and thecorrespondent permeate fraction is kept apart. Atthe end of this 3rd step, four molecular weightcollagenic biopolymer fractions were isolated:1kDa; 1–50 kDa; 50–100kDa and over 100kDa.

- 4th Step _ Freeze-Drying: Each one of the fourultrafiltration fractions must be freeze-dried(lyophilisation) in order to keep their originalstructural and chemical properties. As shown onFigure 7, each unit of lyophilisation equipment wascomposed by the following parts: freezer (D-);condenser (E-); vacuum pump (V-) and storagetanks (T-).

72

Fig.7 Scheme of the industrial plant for the processing of biopolymer extraction and purification.


73

The research activities of the group are focused todevelop and implement cleaner technologies toattain a more environmentally friendly leatherindustry and to study and develop end-of-pipeapproaches to eliminate the main pollutantspresent in tannery waste waters in an attempt toreduce the contamination produced.

STAFFAGUSTÍ MARSAL MONGE, GROUP LEADERFERNANDO MALDONADO MILLÁNPh. D. STUDENTSMARÍA ELENA BAUTISTA PÉREZ SARA CUADROS DOMÉNECH

Development of Non-Contaminant Industrial Processes


Recovery of proteins from wastewater oftannery beamhouse operations: Influence onthe main pollution parameters.Marsal, A., Hernández, E., Cuadros, S., Puig, R.,Bautista, E., Font, J. Water Sci. Technol. 62 658-666, 2010Adsolubilisation of organic compounds ontocollagen fibres. Maldonado, F., Bautista, E., Manich, A.M.,Marsal, A. J. Colloid Interf. Sci. 351 466-471, 2010Determination of dimethylfumarate in leatherand footwear by solid-phase micro extractionand gas chromatography-mass spectrometry.Cuadros, R.M., Font, J., Reyes, M., Ollé, Ll.,Marsal, A.J. Am. Leather Chem. As. 105 395-400, 2010Leather ageing and hexavalent chromiumformation as a function of the fatliquoringagent. Part III: Interaction with synthetic andvegetable retanning agents. Palop, R., Ballús, O., Manich, A.M., Marsal, A. J. Soc. Leath. Tech. Chem. 94 70-76, 2010

Moisture adsorption/desorption kinetics ofbovine hide powder. Manich, A.M., Maldonado, F., Carilla, J., Catalina,M., Marsal, A. J. Soc. Leath. Tech. Chem. 94 15-20, 2010Moisture sorption/desorption of collagen. Manich, A.M., Maldonado, F., Carilla, J., Catalina,M., Marsal, A. J. Am. Leather Chem. As. 105 229-241, 2010Tailor-made biomaterials from collagenicwastes. Catalina, M., Celma, P., Cot, J., Manich, A.,Marsal, A. J. Am. Leather Chem. As. 106 153-160, 2011Determination of TCMTB and other fungicidesin leather.Font, J., Reyes, M., Cuadros, S., Bacardit, A.,Marsal, A. J. Am. Leather Chem. As. 106 341-348, 2011Alternative fungicides: Comparisons withconventional chemicals.Cuadros, S., Manresa, M.A., Font, J., Bautista,M.E., Maldonado, F., Marsal, A.J. Soc. Leath. Tech. Chem. 95 263-269, 2011

The technical limitations and the considerableenvironmental impact of the conventionalfungicide compounds (mainly TCMTB), reinforcethe need to look for new fungicides to replacethem. These alternatives to the fungicidesconventionally used in the tanning industry shouldhave a high efficiency towards a wide range offungi and should be less toxic, moreenvironmentally friendly and cost effective. Withthis aim, the fungicidal capacity of differentselected compounds (registered in the 98/8/ECDirective) such as: diiodomethyl-p-tolylsulfone(DIMPTS), 3-iodo-2-propynyl-N-butylcarbamate(IPBC) and 2-thiazol-4-yl-1H-benzo imidazole,

thiobendazole (TBZ) against different strains offungi was studied in comparison with that ofTCMTB and a mixture of phenolic compounds. Itwas found that low offers of two of the alternativefungicides studied (DIMPTS and IPBC) conferredsatisfactory mould growth resistance to the treatedwet-blue leather, resistance which was higher thatthat conferred by conventional compounds.

The simultaneous determination of TCMTB andseven other fungicides in hides and leather wasachieved by applying easily available techniquessuch as HPLC with photo diode array (PDA)detection with previous extraction with acetonitrile

Research highlights


assisted by ultrasounds. In the last two years, therehas been in Europe a rise in skin allergy anddermatitis due to goods of an Asian provenancethat have been treated with dimethylfumarate(DMFU). There was a need for developing ananalytical method to determine this substance inleather and footwear. Accordingly, a method hasbeen developed that consists of two steps. In thefirst one, DMFU is detected in leather and footwearby applying manual headspace solid-phase micro-extraction and gas chromatography-massspectrometry (GC-MS).

In the second step, the samples in which DMFU isdetected are analysed by a solid-liquid extractionwith acetone after which DMFU is quantitativelydetermined by GC-MS.

With the aim of developing end-of-pipeapproaches to reduce the contamination load oftannery wastewaters, the recovery of solubilizedproteins in the beamhouse operations for a hair-pulping process was studied. The precipitation ofproteins at the isoelectric point was preferred toultrafiltration since this suffers from severalproblems. The wastewaters of soaking, unhairing-liming and washings are those that offer higherprospects of the reduction of the contaminant loadand the production of a valuable material. Theisoelectric precipitation of solubilized proteinsresulted in a major diminution of COD values andprotein content.

Emulsified and suspended fats in wastewater fromhide fleshings experienced co-precipitation withproteins, increasing COD diminution. Anotherimportant result was the drastic decrease in thetoxicity of the wastewater due to the eliminationof a bactericide added in the initial stages of thebeamhouse process. This represents an importantsaving on the cost of wastewater treatment andassociated taxes.The potential use of amino acidsobtained by acid hydrolysis of the precipitatedprotein fraction for the production of amino acid-based surfactants as well as the application of thisprotein material as a retanning agent for tannery iscurrently being investigated.

The removal of vegetable extracts (polyphenols)which are present in aqueous solutions at thehighest concentration of 2.0 g/L by tanneryshavings was studied. It was found that tannerywastes such as chrome and wet white shavingswere good adsorbents of polyphenols in aqueoussolutions.

The adsorption capacity of wet white shavings forpolyphenols was higher than that of chromeshavings. The adsorption isotherms exhibitedLangmuir behaviour, indicating monolayercoverage. Thermodynamic parameters indicatedthat the adsorption process under study wasexothermic and spontaneous. A pseudo-secondorder kinetic model satisfactorily described theadsorption of polyphenols onto tannery shavings.

Adsolubilization has been defined as theincorporation to solid-water interfaces of moleculesthat do not spontaneously adsorb to suchinterfaces, but can be incorporated through sometype of interactions with an adsorbing surfactantmolecule. The adsolubilization phenomenon maytake place on fibrous collagen with different typesof organic molecules. It was found that theadsorption of an anionic surfactant (sodiumdodecylbenzene sulphonate, SDBS) onto hidepowder collagen in an aqueous acidic mediumallows the aggregation of other organic moleculesthat in the absence of the surfactant are not boundto the protein. The anionic surfactant is bound tothe protein in the form of micelle-like aggregatestermed admicelles that permit the incorporation ofother molecules in a process called adsolubilization.The adsorption of the SDBS anionic surfactant onhide powder collagen allowed the adsolubilizationof other molecules such as 2-naphtol, two basicdyes (pararosaniline and hexamethyl-pararosaniline)and a non ionic surfactant that did not adsorb bythemselves to the protein in the conditions studied.Benzyl alcohol was not significantly adsolubilized onhide powder collagen. The hydrophobicity of themolecules played a major role in the adsolubilizationphenomenon.

74


Research work is focussed on the study ofstructure-property relationships of natural,synthetic and sustainable fibrous materials,particularly with regard to thermal, mechanical,viscoelastic and relaxation behaviour. The influenceof novel more sustainable industrial processing onthe structure and properties of fibrous materials arealso taken into account.

STAFFALBERT M MANICH BOU, GROUP LEADER M DOLORS DE CASTELLAR BERTRAN (ad honorem)TECHNICIANSCARMEN FERRERO VIRGOSROSA MATEU MATEU

Statistical Modelling and Fibre Physics


Adsolubilisation of organic compounds ontocollagen fibres.Maldonado, F., Bautista, E., Manich, A.M.,Marsal, A. J. Colloid Interf. Sci. 351 466-471, 2010Thermal transitions of polylactide false-twisttextured multifilaments determined by DSCand TMA.Manich, A.M., Carilla, J., Miguel, R.A.L., Lucas,J.M., Franco, F.G.F., Montero, L.A., Cayuela, D. J. Therm. Anal. Calorim. 99 723-731, 2010Leather ageing and hexavalent chromiumformation as a function of the fatliquoringagent. part III: Interaction with synthetic andvegetable retanning agents. Palop, R., Ballús, O., Manich, A.M., Marsal, A. J. Soc. Leath. Tech. Chem. 94 70-76, 2010Moisture adsorption/desorption kinetics ofbovine hide powder. Manich, A.M., Maldonado, F., Carilla, J., Catalina,M., Marsal, A. J. Soc. Leath. Tech. Chem. 94 15-20, 2010Mechanical properties, relaxation behaviourand thermal characterization of false-twisttextured polylactide multifilament. Manich, A.M., Carilla, J., Miguel, R.A.L., Lucas, J.,Franco, F., Montero, L., Cayuela, D. Vlakna a Textil 17 14-20, 2010Effect of wool keratin proteins and peptideson hair water sorption kinetics. Barba, C., Martí, M., Roddick-Lanzilotta, A.,Manich, A., Carilla, J., Parra, J.L., Coderch, L. J. Therm. Anal. Calorim. 102 43-48, 2010Water absorption/desorption of human hairand nails.Barba, C., Martí, M., Manich, A.M., Carilla, J.,Parra, J.L., Coderch, L. Thermochim. Acta 503-504 33-39, 2010

Moisture sorption/desorption of collagen. Manich, A.M., Maldonado, F., Carilla, J., Catalina,M., Marsal, A. J. Am. Leather Chem. As. 105 229-241, 2010Restoring important hair properties with woolkeratin proteins and peptides.Barba, C., Scott, S., Roddick-Lanzilotta, A., Kelly,R., Manich, A.M., Parra, J.L., Coderch, L. Fiber. Polym. 11 1055-1061, 2010Tailor-made biomaterials from collagenicwastes.Catalina, M., Celma, P., Cot, J., Manich, A.,Marsal, A. J. Am. Leather Chem. As. 106 153-160, 2011Texturing, stretching and relaxation behaviourof polylactide multifilament yarns.Manich, A.M., Miguel, R., Lucas, J., Franco, F.,Baena, B., Carilla, J., Montero, L., Cayuela, D. Text. Res. J. 81 1788-1795, 2011Water sorption of nails treated with woolkeratin proteins and peptides.Barba, C., Martí, M., Roddick-Lanzilotta, A.,Manich, A.M., Carilla, J., Parra, J.L., Coderch, L. J. Therm. Anal. Calorim. 104 323-329, 2011Compatibility of plastic with phase changematerials (PCM).Castellón, C., Martorell, I., Cabeza, L.F.,Fernández, A.I., Manich, A.M.Int. J. Energy Res. 35 765-771, 2011Differential scanning calorimetry andelasticity of textured, heat set and mechanicalstrained polylactide multifilaments.Manich, A.M., Carilla, J., Miguel, R.A.L., Baena,B., Lucas, J., Martí, M., Cayuela, D.Fib. Text. East Eur. 89 22-27, 2011Damaged retrival with ceramide richliposomes.Méndez, S., Manich, A.M., Martí, M., Parra, J.L.,Coderch, L.J. Cosmet. Sci. 62 565-577, 2011

75


Barba, C., Martí, M., Roddick-Lanzilotta, A.,Manich, A., Carilla, J., Parra, J.L., Coderch, L. Water Sorption of Human Keratinized Fibers:Effect of Wool Keratin Proteins and Peptides. in Keratin: Structure, Properties and Applications(eds. R. Dullaart, J. Mousquès) Ch. 4 89-111, 2011Protein Biochemistry, Synthesis, Structure andCellular Functions SeriesNova Science Publishers, Inc. ISBN: 978-1-62100-336-6


Stabilisation of Polylactide MultifilamentsPolylactides (PLA) are biodegradable, biocompatibleand hydrolysable aliphatic polyesters that can bewholly obtained from renewable resources. Naturederived lactides are mostly in L-lactide form andexhibit crystalline behaviour. The microstructure ofthe multi-filaments is not easy to be controlled. Asregards the industrial application of polylactidefilaments the most important objective has beenfocused on the stabilisation of filaments consideringthe dimensional stability and the evolution ofmechanical properties and dyeing behaviour.

Different post-setting treatments have beenperformed and the evolution of both themacromolecular orientation into the filamentmeasured by sonic velocity SV and crystallinitymeasured by differential scanning calorimetry XDSC enabled us to optimize the stabilizationtreatment. Filaments continuously stabilized usinga specially designed chamber running at 20 m/mingave the following XRD patterns, sonic velocity andcrystallinity according to the stabilizationtemperature:

Sorption/desorption kinetics of cellulosic fibresThe parallel exponential kinetics model have beenused to model the fast sorption and desorptionprocesses that occurs on easily accessible sites andthe slow sorption and desorption process occurringat hardly accessible sites

SORPTION SITER a: Crystalline region, b: Amorphous region,c: Interfibrilar molecules, d: Internal pores. SORBED WATERLOCATION 1: External, 2: Amorphous region, 3: Internal, 4:Crystalline region (4).

The total amount Sorbed/Desorbed can be split inthe amount sorbed in the easily accessible sites (R1)and in the hardly accessible sites (R2) at thecorresponding sorption/ desorption times ofsorption T1 and T2 respectively. The evolution ofthe total amount sorbed along the time Rt is asfollows:

Rt = R1 (1-EXP(-t/T1)) + R2 (1-EXP(-t/T2)

Materials with similar sorption/desorptionisotherms can be identified by the fraction ofeasily/hardly accessible sites.

Moisture sorption/desorption of different cellulosicfibres (Cabuya, Sisal, Jute, Kenaf, Luffa, Hemp,Flax) subjected to different treatments (retting,chemical and enzymatic scouring) have been

Research highlights

76


studied. All treatments influence the crystallinitythat can be estimated through water retention.

Drying kineticsDrying kinetics detect variations in fine structure offibres, especially those induced by mechanicalstresses in dry and wet thermal treatments. Thedecrease in mass of a completely wet sample whensubjected to a drying isotherm at 97ºC enables todetermine the evaporation rate of covering water,and water contained in meso- and micropores. Thefirst derivative gives the evaporation rates andwhen plot against humidity content yields thefollowing characteristic plot:

The effect of cracking on polyamide 6.6 wasidentified by this technique that results inaccordance with the SEM plots.

77



Biocompatible surfactants from renewablehydrophiles.Infante, M.R., Pérez, L., Morán, M.C., Pons, R.,Mitjans, M., Vinardell, M.P., García, M.T., Pinazo, A. Eur. J. Lipid Sci. Tech. 112 110-121, 2010Chemical hydrophobic modification of inulinin aqueous media: Synthesis of β-hydroxyalkyl ethers of inulin. Morros, J., Levecke, B., Infante, M.R. Carbohydr. Polym. 81 681-686, 2010Dynamic properties of cationic diacyl-glycerol-arginine-based surfactant/phospholipidmixtures at the air/water interface. Lozano, N., Pinazo, A., Pérez, L., Pons, R. Langmuir 26 2559-2566, 2010Novel biocompatible DNA gel particles. Morán, M.C., Infante, M.R., Miguel, M.G.,Lindman, B., Pons, R. Langmuir 26 10606-10613, 2010Interaction of arginine-based cationicsurfactants with lipid membranes. Anexperimental and molecular simulation study. Almeida, J.A.S., Morán, M.C., Infante, M.R., Pais,A.A.C.C. Arkivoc (part v) 34-50, 2010

Synthesis of β-hydroxyalkyl ethers of inulin inaqueous surfactant media.Morros, J., Levecke, B., Infante, M.R. Carbohydr. Polym. 82 1168-1173, 2010Effects of commercial non-ionic alkyloxyethylene and ionic biocompatiblearginine-based surfactants on thephotophysical behaviour of severalpoly(fluorene-1,4-phenylene).Tapia, M.J., Monteserín, M., Costoyas, A.,Burrows, H.D., Marques, A.T., Pais, A.A.C.C.,Valente, A.J.M., Mallavia, R., Scherf, U., Pinazo,A., Pérez, L., Morán, M.C.J. Mol. Liq. 156 18-27, 2010Preparation of a new oligomeric surfactant:N,N,N′,N″,N″-pentamethyl diethyleneamine—N,N″-di-[tetradecylammonium bromide] andthe study of its thermodynamic properties. Alehyen, S., Bensajjay, F., El Achouri, M., Pérez, L.,Pinazo, A., Infante, M.R.J. Surfact. Deterg. 13 339-348, 2010Study of the interaction between methylorange and mono and bis-quaternaryammonium surfactants. Alehyen, S., Bensejjay, F., El Achouri, M., Pérez, L.,Infante, M.R.J. Surfact. Deterg. 13, 225-231, 2010

78

Biocompatible Surfactants The activity of this research group deals with thefundamental and applied chemical investigation ofnovel environmentally friendly surfactants (productsand processes) from natural renewable sources(proteins, polysaccharides, amino acids and naturaloil derivatives), as alternatives to conventionalsurfactants to be applied in cosmetic, textile,dermo-pharmaceutical medical and food industrialpreparations. These compounds can be classified asspecialty surfactants with biodegradable,antimicrobial and low toxicity profiles, andcharacteristic self-aggregation properties. Theobjectives are focused on the preparation of saferand healthier surfactants using molecular designand the principles of toxicity and environmentalmechanism of action to minimise the intrinsictoxicity/ecotoxicity of the product while maintainingits efficacy and function. This line is loosely-boundwith applied surface chemistry and biological area.It is active in the following tasks: the use ofrenewable raw materials for the synthesis ofsurfactants: proteins, polysaccharides, triglycerides;Employing natural processes using biocatalystbased chemical transformations (enzymes) forefficiency and selectivity; the use of safer solvents(water systems, solvent-free processes, Ionic liquids,etc.); study of mechanism of cellular action; novelfunctionality: bio/nano materials; self-assemblingand ecotoxicity characterization.

STAFFMª ROSA INFANTE MARTÍNEZ-PARDO, GROUP LEADERLOURDES PÉREZ MUÑOZ AURORA PINAZO GASSOL Ph. D. LORENA TAVANOAURORA COLOMER FLORESJORDI MORROS CAMPSPh. D. STUDENTSMARINA LOZANO ERRA


Comparative sensitivity of tumor and non-tumor cell lines as a reliable approach for invitro cytotoxicity screening of lysine-basedsurfactants with potential pharmaceuticalapplicationsNogueira, D.R., Mitjans, M., Infante, M.R.,Vinardell, M.P. Int. J. Pharm. 420 51-58, 2011Inhibition of the corrosion of iron in acidicsolution by the oligomeric surfactant N, N, N′,N″, N″-pentamethyl diethyleneamine-N, N″-di-[tetradecylammonium bromide] Bensajjay, F., Alehyen, S., Achouri, M.E., Hajjaji,N., Bellaouchou, A., Pérez, L., Infante, M.R. Anti-Corros. Method M. 58 258-266, 2011Arginine diacyl-glycerolipid conjugates asmultifunctional biocompatible surfactants Pinazo, A., Lozano, N., Pérez, L., Morán, M.C.,Infante, M.R., Pons, R. C. R. Chim. 14 726-735, 2011The role of counterions in the membrane-disruptive properties of pH-sensitive lysine-based surfactants Nogueira, D.R., Mitjans, M., Infante, M.R.,Vinardell, M.P. Acta Biomater. 7 2846-2856, 2011

Amino acids as raw material forbiocompatible surfactants Pinazo, A., Pons, R., Pérez, L., Infante, M.R. Ind. Eng. Chem. Res. 50 4805-4817, 2011Hydrophobically modified inulin from alkenylsuccinic anhydride in aqueous media Morros, J., Levecke, B., Infante, M.R. Carbohydr. Polym. 84 1110-1116, 2011Cationic surfactants derived from lysine:Effects of their structure and charge type onantimicrobial and hemolytic activities Colomer, A., Pinazo, A., Manresa, M.A.,Vinardell, M.P., Mitjans, M., Infante, M.R., Pérez, L. J. Med. Chem. 54 989-1002, 2011Self-aggregation and antimicrobial activity ofimidazolium and pyridinium based ionicliquids in aqueous solution. Cornellas, A., Pérez, L., Comelles, F., Ribosa, I.,Manresa, A., García, M.T. J. Colloid Interface Sci. 355 164-171, 2011Diacyl glycerol arginine-based surfactants:biological and physicochemical properties ofcatanionic formulations.Lozano, N., Pons, R., Pérez, L., Pinazo, A. Amino Acids 40 721-729, 2011

79

Pons, R., Moran, M. C., Infante, M. R., Pinazo, A.,Pérez, L.Lysine-Based Surfactants.in Colloids in Biotechnology (ed. M. Fanun) 125-138, 2010Surfactant Science Series, Vol. 152 CRC Press (Taylor and Francis). ISBN 9781439830802Benincasa, M., Marqués, A., Pinazo, A., Manresa, A. Rhamnolipid Surfactants: AlternativeSubstrates, New Strategies .in Biosurfactants (ed. R. Sen) Section III, 170-184,2010Advances in Experimental Medicine and Biology,Vol. 672 Springer New York. DOI: 10.1007/978-1-4419-5979-9_13

Moran, C., Pérez, L., Pons, R., Pinazo, A., Infante,M.R. Amino Acids, Lactic Acid and Ascorbic Acid asRaw Materials for Biocompatible Surfactant.in Surfactants from Renewable Resources (eds.M. Kjellin, I. Johansson), Ch. 5, 85-107, 2010John Wiley & Sons, Ltd, Chichester, UK.doi:10.1002/9780470686607.Pinazo, A., Pérez, L., Infante, M.R., Vinardell,M.P., Mitjans, M., Morán, M.C., Martínez, V. Chemical Structure and Toxicity in Arginine-Based Surfactants.in Arginine Amino Acid (ed. N.L. Jacobs) 125-142, 2011Microbiology Research Advances SeriesNova Science Publishers Inc. ISBN: 978-1-61761-981-6



80

For the first time, we reported a novel class ofmultichain lysine-based cationic amphiphilicderivatives of the type N(epsilon),N(epsilon)'-bis(n-acyloxypropyl)-l-lysine methyl ester salts (patentprotected).

The research of biocompatible surfactant grouprelates to novel compounds having an amphiphiliccharacter (cationic, anionic, amphoteric and non-ionic surfactants), which are intended to be used inthe food, pharmaceutical and cosmetic industriesas surface-active agents having a rich self-assembling, antimicrobial and low toxicityproperties. Due to their interesting properties thesecompounds have been transferred to the industry.

At present, cationic surfactants are being tested innew biomedical applications, such as drug deliverysystems in cationic vesicles.

In this field it is necessary to strike a balancebetween antimicrobial activities on the one handand low toxicity and efficient biodegradability on

the other. In this sense we have designed a newfamily of cationic surfactants from lysine,onechain/one head, one chain/two heads, and twochains/two heads with moderate antimicrobialactivity and excellent non-haemolytic behaviour.The acute toxicity against Daphnia magna andbiodegradability tests revealed that all threesurfactants from lysine can be classified as readylybiodegradable surfactants.

Surfactant/phospholipid mixtures are important inmany applications, including emulsion and foamstabilization, lung surfactants and the stability ofcell membranes. Acyl-glycerol amino acidconjugates constitute a class of specific lipo aminoacid surfactants sharing properties with glyceridesand phospholipids.

They consist of two aliphatic chains and thearginine amino acid as polar head, linked togetherthrough ester bonds in the glycerol backbone. Thestudies of the adsorption at the air liquid interfaceof diacyl glycerol derivatives and their mixtures withphospholipids helped to understand the complexmechanism of interaction with cell membranes.The results obtained with catanionic formulationacyl-glycerol amino acid surfactants/phospholipidssuggests that these products are excellentcandidates for developing new surfactants withtunable, well-defined properties for medical andbiotechnological applications. Our results might beconsidered as a proof of principle of a strategywhich reduces the toxicity of many surfactants,opening possibilities into clinical applications.

Research highlights


81


Sonogashira coupling reactions inbiodegradable ionic liquids derived fromnicotinic acid.Harjani, J.R., Abraham, T.J., Gómez, A.T., García,M.T., Singer, R.D., Scammells, P.J.Green Chem. 12 650-655, 2010Further studies on the biodegradation of ionicliquids.Ford, L., Harjani, J.R., Atefi, F., García, M.T.,Singer, R.D., Scammells, P.J.Green Chem. 12 1783-1789, 2010Biocompatible surfactants from renewablehydrophiles.Infante, M.R., Pérez, L., Morán, M.C., Pons, R.,Mitjans, M., Vinardell, M.P., Garcia, M.T., Pinazo, A. Eur. J. Lipid Sci. Tech. 112 110-121, 2010Formation of vesicles with an organometalliclipid bilayer by supramolecular arrangementof metal carbonyl metallosurfactant.Parera, E., Comelles, F., Barnadas, R., Suades, J.Chem. Commun. 47, 4460-4462, 2011Surface and self-aggregation properties of bis-benzimidazolones derivatives of D-glucose. Lakhrissi, B., Lakhrissi, L., Massoui, M., Essassi,E.M., Comelles, F., Esquena, J., Solans, C.,Rodríguez-Abreu, C. J. Surfact. Deterg.13 329-338, 2010New surfactant phosphine ligands andplatinum(II) metallosurfactants. influence ofmetal coordination on the critical micelleconcentration and aggregation properties. Parera, E., Comelles, F., Barnadas, R., Suades, J. Langmuir 26 743-751, 2010

Surface-active properties of lipophilicantioxidants tyrosol and hydroxytyrosol fattyacid esters: A potential explanation for thenonlinear hypothesis of the antioxidantactivity in oil-in-water emulsions.Lucas, R., Comelles, F., Alcántara, D., Maldonado,O.S., Curcuroze, M., Parra, J.L., Morales, J.C. J. Agric. Food Chem. 58 8021-8026, 2010Synthesis and characterization of phenolicantioxidants with surfactant properties:Glucosyl- and glucuronosyl alkyl gallates .Maldonado, O.S., Lucas, R., Comelles, F., JesúsGonzález, M., Parra, J.L., Medina, I., Morales, J.C. Tetrahedron 67 7268-7279, 2011Enzymatic synthesis of α-glucosides ofresveratrol with surfactant activity. Torres, P., Poveda, A., Jimenez-Barbero, J., Parra,J.L., Comelles, F., Ballesteros, A.O., Plou, F.J. Adv. Synth. Catal. 353 1077-1086, 2011Self-aggregation and antimicrobial activity ofimidazolium and pyridinium based ionicliquids in aqueous solution. Cornellas, A., Pérez, L., Comelles, F., Ribosa, I.,Manresa, A., García, M.T. J. Colloid Interf. Sci. 355 164-171, 2011Synthesis and properties of ascorbyl esterscatalyzed by lipozyme TL im usingtriglycerides as acyl donors. Reyes-Duarte, D., López-Cortés, N., Torres, P.,Comelles, F., Parra, J.L., Peña, S., Ugidos, A.V.,Ballesteros, A., Plou, F.J. J. Am. Oil Chem. Soc. 88 57-64, 2011

Environmental Chemistry of Surfactants and Ionic LiquidsThe main objective is the study of thephysicochemical and biological properties relatedto the behaviour, fate and effects of surfactantsand ionic liquids in the environment for the designand selection of environmentally friendlycompounds. Our research activities are mainlyfocused on the bioavailability, biodegradability andtoxicity of surfactants and ionic liquids in theaquatic environment.

STAFFMARÍA TERESA GARCÍA RAMÓN, GROUP LEADER FRANCESC COMELLES FOLCH TECHNICIANSJUAN JOSÉ GONZÁLEZ CHAPARRO ISABEL MUÑOZ LIRÓN ROSA MARÍA SALVIA PEIRÓ

Ph. D.ISABEL RIBOSA FORNOVI Ph. D. STUDENTSANNA CORNELLAS PITARCH STUDENTSMORGANE ROUGIER


82

Biodegradability of Ionic LiquidsIonic liquids (ILs) are deemed greener solventalternatives in chemical synthesis mainly becauseof their negligible vapor pressure, high thermalstability, low flammability and reusability inchemical applications. They are also known to havean influence on the rate and selectivity of certainchemical reactions. As research in the area of ILscontinues to grow, the domain of their applicationshas substantially broadened. The non-volatility ofILs under operational conditions minimizes theirimpact on air quality during their life cycle.However, their impact on soil and water is certainlyof considerable concern at the time of theirdisposal. Research in this area is currently vital asILs are likely to make a transition from academiclaboratories to large scale operations wheredisposal of any chemical is a major concern. Theevaluation of the environmental impact of ILs can,in part, be gauged by parameters such asbiodegradability and toxicity. Enormous structuralvariations are possible in the ILs by changing eitherthe cation and/or the anion. This leads us to believethat it should be possible to manipulate theirchemical architecture to achieve highbiodegradability. In collaboration with ProfessorPeter Scammells (Monash University) researchgroup, different structural parameters promotingbiodegradation of ionic liquids commonly used asreaction media have been identified. The increaseof biodegradability promotes the removal of thesecompounds avoiding their persistence in theenvironment once their function has finished. ILswith a pyridinium cation were synthesized andtheir biodegradability was evaluated using the CO2headspace test (ISO 14593). ILs bearing an esterside chain moiety were prepared from eitherpyridine or nicotinic acid and showed high levels ofbiodegradation under aerobic conditions and canbe classified as ‘readily biodegradable’. Thispresents the possibility that substituted pyridiniumrings lead to metabolites that are not refractoryupon biodegradation. The study also demonstratesthat the structural manipulation of the pyridiniumskeleton may lead to ILs likely to possess goodsolvent attributes and a predisposition tobiodegrade when released into an aquaticenvironment.

Surfactant-like behaviour and antimicrobialactivity of Ionic Liquids in aqueous solutionAmphiphilic imidazolium and pyridinium based ILsbehave as conventional cationic surfactants inaqueous solution reducing the surface tension to37-42 Nm/m. There is no significant differencebetween imidazolium and pyridinium ILs regardingsurface activity and aggregation behaviour inaqueous solution which indicates a similar polarityof the methylimidazolium and pyridiniumheadgroups. In the homologous series of ILsinvestigated the tendency to micellize increasesand CMC decreases regularly with the length of

the alkyl tail attached to the polar head group.Thus, the major driving force of the micellization ofthese amphiphilic imidazolium and pyridiniumcations seems to be the hydrophobic interactionbetween their alkyl tails.

Long-chain imidazolium and pyridinium ILs show surfactant-like properties in aqueous solution and display increasingantimicrobial activity with alkyl chain length.

The amphiphilic ILs studied displayed antimicrobialactivity. The length of the alkyl side chaindetermines the efficiency of these ILs asantimicrobial agents. The compounds with shortalkyl substituents are not active against bacteriaand fungi whereas the ILs containing 10-14 Catoms in the alkyl chain show significantantimicrobial activity, the C14 being the most activecompounds. In addition to their unique physicalproperties as ionic liquids, amphiphilic imidazoliumand pyridinium ILs have antimicrobial activity andsurfactant-like behaviour. The improvedunderstanding of the structural parametersaffecting self-aggregation and biological activity ofthe long chain ILas is expected to aid in the designand selection of ionic liquids with betterphysicochemical and biological properties for newpharmaceutical, engineering or nanotechnologyapplications. These results are also significant tothe environmental fate assessment of thesecompounds as the interfacial phenomena play acrucial role in the biodegradation processes due tochanges in affinity and availability of the ionicliquids in the intercellular spaces.

Interactions between Conventional Surfactantsand ILsOne of the most outstanding properties of ionicliquids (ILs) is its very low volatility that preventsenvironmental air pollution and consequentlymakes them candidates to substitute volatileorganic solvents in different application fields.Accordingly with its claimed role of “greensolvents”, a wide series of studies where typicalionic liquids are used as dilution media ofconventional surfactants are reported. In some ofthese studies the surfactant is dissolved in the ionicliquid as unique solvent, whereas in others thesolvent media is made of a fixed concentration ofionic liquid in water. In recent studies, we put in

Research highlights


83

evidence that even for short alkyl chain ionicliquids, a process of aggregation in aqueoussolution took place. Consequently, when asurfactant is dissolved in an aqueous solutioncontaining ionic liquid, the role of this compoundas a secondary surfactant should also beconsidered. Then, we claimed that these systemsshould be treated as the typical binary surfactantsystems in aqueous solution, in which case thephenomena of synergism frequently occur. One ofthe research lines of our group is devoted to thestudy of binary systems made of conventional

surfactants of different families (non ionic, anionic,cationic…) and typical ionic liquids in aqueoussolutions from this point of view. We planned thesestudies considering the total concentration ofsurfactant and ionic liquid, combined at differentmole ratios. Then, the surfactant parametersobtained should not be attributable solely to thesurfactant, but to the mixed micelles formedbetween the surfactant and the ionic liquid. Thisapproach can contribute to a better understandingof the experimental results reported when only therole of solvent is considered for the ionic liquid.


The general subject of research is the physicalchemistry of surfactants and surfactant basedsystems. Particular focus is given to dynamictransformations (emulsification and solubilisation)and to new biocompatible surfactant behaviour.The main techniques are SAXS-WAXS, lightscattering, tensiometry, conductivity and selectiveelectrode.

STAFFRAMON PONS PONS, GROUP LEADER

TECHNICIANSJAUME CAELLES BALCELLS IMMA CARRERA ALTARRIBA

Ph. D. STUDENTAMALIA MEZEI NEUS LOZANO VALDÉS

Physical Chemistry of Surfactant Systems

84


Novel biocompatible DNA gel particles.Morán, M.C., Infante, M.R., Miguel, M.G.,Lindman, B., Pons, R. Langmuir 26 10606-10613, 2010Application of bicellar systems on skin:Diffusion and molecular organization effects. Rodríguez, G., Rubio, L., Cócera, M., Estelrich, J.,Pons, R., De La Maza, A., López, O. Langmuir 26 10578-10584, 2010Headgroup effects on the unusual lamellar-lamellar coexistence and vesicle-to-micelletransition of salt-free catanionic amphiphiles. Silvas, B.F.B., Marques, E.F., Olsson, U., Pons, R. Langmuir 26 3058-3066, 2010Dynamic properties of cationic diacyl-glycerol-arginine-based surfactant/phospholipidmixtures at the air/water interface. Lozano, N., Pinazo, A., Pérez, L., Pons, R. Langmuir 26 2559-2566, 2010Structure of aggregates in diluted aqueousoctyl glucoside/tetraethylene glycolmonododecyl ether mixtures with differentalkanols. Pons, R., Valiente, M., Montalvo, G. Langmuir 26 2256-2262, 2010

Biocompatible surfactants from renewablehydrophiles.Infante, M.R., Pérez, L., Morán, M.C., Pons, R.,Mitjans, M., Vinardell, M.P., Garcia, M.T., Pinazo, A. Eur. J. Lipid Sci. Tech. 112 110-121, 2010Arginine diacyl-glycerolipid conjugates asmultifunctional biocompatible surfactants.Pinazo, A., Lozano, N., Pérez, L., Morán, M.C.,Infante, M.R., Pons, R. C.R. Chim. 14 726-735, 2011Amino acids as raw material forbiocompatible surfactants.Pinazo, A., Pons, R., Pérez, L., Infante, M.R. Ind. Eng. Chem. Res. 50 4805-4817, 2011Diacyl glycerol arginine-based surfactants:Biological and physicochemical properties ofcatanionic formulations.Lozano, N., Pérez, L., Pons, R., Pinazo, A. Amino Acids 40 721-729, 2011Isolation and partial characterization of abiosurfactant mixture produced bySphingobacterium sp. isolated from soil.Burgos-Díaz, C., Pons, R., Espuny, M.J., Aranda,F.J., Teruel, J.A., Manresa, A., Ortiz, A., Marqués,A.M.J. Colloid Interface Sci. 361 195-204, 2011


Pons, R., Moran, M. C., Infante, M. R., Pinazo, A.,Pérez, L.Lysine-Based Surfactants.in Colloids in Biotechnology (ed. M. Fanun)Surfactant Science Series, Vol. 152 125-138, 2010CRC Press (Taylor and Francis). ISBN 9781439830802Moran, C., Pérez, L., Pons, R., Pinazo, A., Infante, M.R. Amino Acids, Lactic Acid and Ascorbic Acid asRaw Materials for Biocompatible Surfactant.in Surfactants from Renewable Resources (eds.M. Kjellin, I. Johansson), Ch. 5, 85-107, 2010John Wiley & Sons, Ltd, Chichester, UK.doi:10.1002/9780470686607.

De Persiis, F., Pons, R., Pucci, C., Tardani, F., LaMesa, C.Binding of Protein-Functionalized Entitiesonto Synthetic Vesicles.in Non-Viral Gene Therapy, (ed. Xu-bo Yuan)645-660, 2011 InTech.ISBN: 978-953-307-538-9 (Available from:http://www.intechopen.com/articles/show/title/binding-of-protein-functionalized-entities-onto-synthetic-vesicles)


85

In recent work, special effort has been devoted tothe determination of structures formed bybiobased surfactants obtained from the linkage oflysine or arginine with hydrophobic tails. Thosestudies stem from the collaboration with theBiocompatible Surfactants Group. In particulardiacyl glycerol derivatives mimic the phospholipidspresent at membranes. Particularly relevant is theeffect of small amounts of diacyl glicerolipids onthe adsorption characteristics of phospholipidswith a newly found boosting effect for surfacetension reduction. Also natural biosurfactantsobtained from bacterial growth have been studiedin collaboration with the faculty of Pharmacy of theUniversity of Barcelona.

Catanionic surfactants and mixtures show someinteresting and amazing phenomena. In the phasebehaviour of catanionic surfactants (1:1 catanionicmixtures without simple counterions) thecoexistence of two lamellar phases was establishedin collaboration with the University of Porto.Catanionic vesicles have also been used as a modelmembrane for the study of the interaction ofprotein functionalised nanoparticles with bilayers.This complex subject has been undertaken withinthe collaboration with the University of Rome LaSapienza. Other lamellar phases of interest areconstituted by nonionic surfactants of thepolyethylene-glycol type which can incorporatedifferent amounts of alcohols in the bilayers withchanges in their thickness and in the extension ofthe bilayers. Those surfactants have been studiedin collaboration with the University of Alcalá.

The interaction of cationic surfactants with anionicnatural polymer (for instance DNA) formprecipitates. Those precipitates can be used to formparticles which can release DNA. These systemshave been studied in collaboration with theUniversity of Coimbra. Those non viral vectors areone of the DNA transfection paths that arecurrently explored. Our investigation has focusedon the structure of the aggregates and its influenceon the release kinetics. Linkage differences in the

headgroup amino acid of lipoamino acids showstrong influence in the packing and, consequently,on the release kinetics. Those differences havebeen studied by SAXS and GISAXS. In the examplesbelow, isotropic precipitates and strongly orientedprecipitates at full hydration are shown.

Fig. 1 Oriented Sample GISAX pattern at full hydration.

Fig. 2 Unoriented Sample GISAX pattern at full hydration.

Related to research using Small Angle X-RayScattering, a controlled atmosphere setup for usewith the GISAXS configuration has been patented

Research highlights


STAFFJOSÉ LUIS PARRA JUEZ, GROUP LEADERMª LUISA CODERCH NEGRA ALFONS DE LA MAZA RIBERA OLGA LÓPEZ SERRANO

TECHNICIANSMERITXELL MARTÍ GELABERT ISABEL YUSTE HERNÁNDEZ VANESSA MARTÍNEZ RODRÍGUEZ

Ph. D. CRISTINA ALONSO MERINO CLARA BARBA ALBANELLMERCEDES CÓCERA NÚÑEZ

Ph. D. STUDENTSGELEN RODRÍGUEZ DELGADO LAIA RUBIO TOLEDANO

The main research lines of this group are: lipidassembling (liposomes, micelles, bicelles andbilayers), lipokeratinic tissues (skin, wool andhuman hair), percutaneous absorption andphysicochemical characterization of colloids withpotential industrial applications.

Biophysics of Lipids and Interphases

86


Effect of wool keratin proteins and peptideson hair water sorption kinetics.Barba, C., Martí, M., Roddick-Lanzilotta, A.,Manich, A., Carilla, J., Parra, J.L., Coderch, L. J. Therm. Anal. Calorim. 102 43-48, 2010Surface-active properties of lipophilicantioxidants tyrosol and hydroxytyrosol fattyacid esters: A potential explanation for thenonlinear hypothesis of the antioxidantactivity in oil-in-water emulsions.Lucas, R., Comelles, F., Alcántara, D., Maldonado,O.S., Curcuroze, M., Parra, J.L., Morales, J.C. J. Agric. Food Chem. 58 8021-8026, 2010Skin delivery of caffeine contained inbiofunctional textiles.Rubio, L., Alonso, C., Coderch, L., Parra, J.L.,Martí, M., Cebrián, J., Navarro, J.A., Lis, M.,Valldeperas, J. Text. Res. J. 80 1214-1221, 2010Skin efficacy of liposomes composed ofinternal wool lipids rich in ceramides.Ramírez, R., Martí, M., Barba, C., Méndez, S.,Parra, J.L., Coderch, L. J. Cosmet. Sci. 61 235-245, 2010Water absorption/desorption of human hairand nails.Barba, C., Martí, M., Manich, A.M., Carilla, J.,Parra, J.L., Coderch, L. Thermochim. Acta 503-504 33-39, 2010New anionic surface-active agent derivedfrom wool proteins for hair treatment.Barba, C., Scott, S., Kelly, R., Parra, J.L., Coderch, L.J. Appl. Polym. Sci. 115 1461-1467, 2010

Influence of internal lipids on dyeing of woolfibres.Martí, M., Ramírez, R., Barba, C., Coderch, L.,Parra, J.L.Text. Res. J. 80 365-373, 2010Bicellar systems for in vitro percutaneousabsorption of diclofenac.Rubio, L., Alonso, C., Rodríguez, G., Barbosa-Barros, L., Coderch, L., de la Maza, A., Parra, J.L.,López, O.Int. J. Pharm. 386,108-113, 2010Bicosomes: Bicelles in dilute systems. Rodríguez, G., Soria, G., Coll, E., Rubio, L.,Barbosa-Barros, L., López-lglesias, C., Planas,A.M., Estelrich, J., de La Maza, A., López, O. Biophys. J. 99 480-488, 2010Application of bicellar systems on skin:Diffusion and molecular organization effects. Rodríguez, G., Rubio, L., Cócera, M., Estelrich, J.,Pons, R., de La Maza, A., López, O. Langmuir 26 10578-10584, 2010Synthesis and characterization of phenolicantioxidants with surfactant properties:Glucosyl- and glucuronosyl alkyl gallates. Maldonado, O.S., Lucas, R., Comelles, F.,González, M.J., Parra, J.L., Medina, I., Morales,J.C. Tetrahedron 67 7268-7279, 2011Structural effects of flufenamic acid inDPPC/DHPC bicellar systems. Rubio, L., Rodríguez, G., Alonso, C., López-Iglesias, C., Cócera, M., Coderch, L., de La Maza,A., Parra, J.L., López, O. Soft Matter 7 8488-8497, 2011


87

Barrier function of intact and impaired skin:Percutaneous penetration of caffeine andsalicylic acid. Rubio, L., Alonso, C., López, O., Rodríguez, G.,Coderch, L., Notario, J., de la Maza, A., Parra, J.L. Int. J. Dermatol. 50 881-889, 2011Enzymatic synthesis of α-glucosides ofresveratrol with surfactant activity. Torres, P., Poveda, A., Jimenez-Barbero, J., Parra,J.L., Comelles, F., Ballesteros, A.O., Plou, F.J. Adv. Synth. Catal. 353 1077-1086, 2011Water sorption of nails treated with woolkeratin proteins and peptides. Barba, C., Martí, M., Roddick-Lanzilotta, A.,Manich, A., Carilla, J., Parra, J.L., Coderch, L. J. Therm. Anal. Calorim. 104 323-329, 2011Liposome as dispersing agent into dispersedye formulation.Marti, M., de la Maza, A., Parra, J.L., Coderch, L. Text. Res. J. 81 379-387, 2011Synthesis and properties of ascorbyl esterscatalyzed by lipozyme TL im usingtriglycerides as acyl donors. Reyes-Duarte, D., López-Cortes, N., Torres, P.,Comelles, F., Parra, J.L., Peña, S., Ugidos, A.V.,Ballesteros, A., Plou, F.J. J. Am. Oil Chem. Soc. 88 57-64, 2011Biofunctional textiles prepared withliposomes: In vivo and in vitro assessment Martí, M., Martínez, V., Rubio, L., Coderch, L.,Parra, J.L. J. Microencapsul. 28 799-806, 2011Characterisation of skin states by non-crystalline diffraction. Cócera, M., Rodríguez, G., Rubio, L., Barbosa-Barros, L., Benseny-Cases, N., Cladera, J., Sabés,M., Fauth, F., de La Maza, A., López, O. Soft Matter 7 8605-8611, 2011

Structural versatility of bicellar systems andtheir possibilities as colloidal carriers.Barbosa, L., Rodríguez, G., Cócera, M., Rubio, L.,López-Iglesias, C., de la Maza, A., López, O. Pharmaceutics 3 636-664, 2011Bicellar systems as modifiers of skin lipidstructure.Rodríguez, G., Barbosa-Barros, L., Rubio, L.,Cócera, M., López-Iglesias, C., de la Maza, A.,López, O. Colloid Surf. B-Biointerfaces 84 390-394, 2011Damaged retrival with ceramide richliposomes.Méndez, S., Manich, A.M., Martí, M., Parra, J.L.,Coderch, L.J. Cosmet. Sci. 62 565-577, 2011

Publications (books and book chapters) Barba, C., Martí, M., Roddick-Lanzilotta, A.,Manich, A., Carilla, J., Parra, J.L., Coderch, L. Water Sorption of Human Keratinized Fibers:Effect of Wool Keratin Proteins and Peptides. in Keratin: Structure, Properties and Applications(eds. R. Dullaart, J. Mousquès) Ch. 4 89-111, 2011Protein Biochemistry, Synthesis, Structure andCellular Functions SeriesNova Science Publishers, Inc. ISBN: 978-1-62100-336-6 Martí, M., J Parra, J.L., Coderch, L. Lipid Role in Wool Dyeing.in Natural Dyes (ed. E. Perrin AkçakocaKumbasar) Ch. 5 80-100, 2011InTech. ISBN: 978-953-307-783-3.Barba, C., Scott, S., Roddick-Lanzilotta, A., Parra,J.L., Coderch, L.Keratin Proteins and Peptides from Wool, forHair Restoration. in Advances in Medicine and Biology Vol. 5 (ed.L.V Berhardt) Ch. 13 237-242, 2011Nova Science Publishers, Inc. ISBN: 978-1-60456-557-7

Some of the main results of our group in the fieldof biomembranes refer to the scientific noveltyrelated to the use of bicellar systems in cosmeticand pharmacologic skin applications. Bicelles arebilayered nano-aggregates formed by long andshort chain phospholipid compounds dispersed inaqueous solution, which have proven to beinteresting membrane-mimicking systems toinvestigate the structure of membrane proteins.

The above schematic representation showslamellar phase bicelles:

(A) Perforated lamellae morphology of magneticallyaligned dimyristoyl-phosphatidylcholine/dihexanoyl-phosphatidyl-choline (DMPC/DHPC) bicellesconsisting of both planar and high-curvatureregions. DMPC and DHPC are represented by theyellow and red colours, respectively.

(B) Schematic representation of DHPC undergoingfast exchange between the planar and highlycurved toroidal pore regions, as indicated by thearrows.

Research highlights


According to our investigations bicelles interactwith the microstructure of the stratum corneumaffecting some of the biophysical properties of theskin. Thus, topical in vivo application ofDMPC/DHPC bicelles improve skin permeation andelastic parameters and decreased skin hydrationwithout promoting irritation and without affectingstratum corneum lipid microstructure. The increaseof permeability was possibly due to changes in thestratum corneum lipids phase behaviour.

In order to deepen the interpretation of theseresults we investigated the effect of these bicelles instratum corneum in vitro using attenuated totalreflectance-Fourier transform infrared spectroscopytechnique. It is noteworthy that bicelles caused aphase transition from the gel or solid state to theliquid crystalline state in the lipid conformation ofSC, reflecting the major order-disorder transitionfrom hexagonally packed to disordered chains.Grazing incidence small and wide X-ray scattering(GISAXS and GIWAXS) techniques also confirmedthis effect that may be probably associated to thepermeabilizing effect described for these bicelles.

On the other hand these bicelles are also able toincorporate ceramides up to 20% formingelongated or tubular structures and vesicles thatgrow with temperature. The four next TEMmicrographs show 20%-Cer samples cryofixedusing high-pressure freezing at 40 C. In panel A,the blackarrow points to a multilamellar tubule.Panel B images a cross-fracture of the tubules.Panels C and D show vesicles with sizes over 500nm mixed with tubules with sizes varying in a largerange (white arrows).

In general terms the inclusion of ceramides in thesebicelles offers the possibility of improving thecurrent knowledge about many physiologicalprocesses associated with ceramides and give newinsights for the role played by this lipid in biologicalcells at membrane level.

In the following two micrographs it may be seen thatbicelles formed by dipalmitoyl-phosphatidylcholine(DPPC) and DHPC are also able to penetrate thestratum corneum in vitro, to grow and to formvesicles inside the intercellular lipid spaces. Thisgrowth was also observed when bicelles werediluted with water. These changes resemble micelle-to-vesicle transitions of the lipid-surfactant systems

The absence of surfactant in the bicellarcomposition and their small size gives greatadvantages to these structures in comparison toother systems for skin purposes. The goodpenetration, high skin compatibility and theirability to modulate the barrier function makebicelles a smart nano-system with promisingapplications as drug carriers through the skin.

In addition, bicelles can also incorporate other lipidspecies such as those present in skin (cholesterolsulfate), or drugs (fluflenamic, acid, diclofenac,enrofluxacine, mycostatine).

Biofunctional TextilesIn recent years, new technologies have led to theproduction of biofunctional textiles. These textilesare able to release therapeutic compounds orcosmetics to the skin. The biofunctional textilescontain microscopic capsules of ingredients thatbreak as the fabric rubs the skin, releasing theactives. Absorption and desorption behaviour ofactive agents embedded into the differentbiofunctional textiles should be taken into accountwhen determining the amount of active agentsincorporated into these textiles and whenfollowing the delivery mechanism as the fabriccomes into contact with the skin. This group wasworking into this subject, preparing biofunctionaltextiles in order to know what exactly happenwhen textiles comes in contact with human skin,and to quantify the actives.

Microcapsules or liposomes were used as vehicles.Liposomes were prepared with wool lipid (IWL)extracts enriched with ceramides. Liposomes and microcapsules containing different activeprinciples were applied on textile fabrics. As anactive principle the ceramides present in theinternal wool lipids have been used and asreference compounds caffeine and a sun filter(ethylhexyl methoxycinnamate) have been alsoused as tracers. The demonstration of the activeprinciple release by a close textile-skin contact,

88


using a new specific design of percutaneousabsorption was carried out (see figure).

The passage of the active principle throughdifferent skin layers have been detected “in vitro”.In this research textiles were applied onto volunteerforearms to prove if there were some benefits forthe skin by non invasive techniques such asTewameter and Corneometer as well as to detectthe active compound in the stratum corneum bystripping method. From the results obtained, it hasbeen demonstrated the skin effectiveness of anactive compound encapsulated and applied onto afabric when it is topically applied. IWL liposomesfrom the biofunctional textile increased the level ofskin hydration and decreased the TEWL values. On

the other hand, the sun filter has been detected inthe outermost layers of the stratum corneum.

This group also does research into cosmetic field,studying changes in the properties of humankeratin fibers, such as hair and nails due to waterpresence. Reactive cosmetic treatments of hair andnails often impair fiber structure, resulting in anadverse effect on water absorption. The moistureabsorption/desorption isotherm curves foruntreated hair and nails and the kinetics of theseprocesses are studied in this research.

The effects of different chemical cosmetictreatments on hair and nail water absorption arealso evaluated. The isotherms for these humankeratinized tissues behaved as expected, with acharacteristic hysteresis between moisture uptakeand desorption. Human nails showed a lowermoisture regain and a much lower diffusioncoefficient with respect to human hair.Permeability, directly related to the diffusioncoefficient, increased with the degradationtreatment. The diffusion coefficient was importantin determining the integrity of keratin fibers.

89


FACILITIESAND

TECHNOLOGY TRANSFER

6


IQAC FACILITIES AND TECHNOLOGY TRANSFER

93

Characterization of Colloidal Dispersions Service

Custom Antibody Service (CAbS)

Organic Microanalysis Service

Biodegradation and Aquatic Toxicity Service

Magnetic Resonance Service

Skin Absorption and Skin Efficacy Services

SAXS-WAXS Service

Synthesis of High Added Value Molecules Service

Thermal Analysis and Calorimetry Service

Proteomics Service

Technology transfer


Relevant techniques:� Static (SLS) and dynamic (DLS) light scattering

Determination of particle size distribution, shape,diffusion coefficient, aggregation number,molecular weight of colloidal dispersions

Other techniques.

Laser Light Diffraction Light back scatteringZetameterDifferential Refractometry Tensiometry,Optical Microscopy

Rheology

Determination of rheological properties of fluidsand soft matter in flow and deformation regimesby steady state (viscosity, shear thinning, shearthickening) and dynamic (elastic and viscousmoduli, relaxation time) measurements

94

Characterization of Colloidal Dispersions ServiceThis service deals with the characterization ofnano-structured liquids (e.g. micelles, vesicles,liquid crystals, microemulsions, nanoemulsionsetc.) and solid dispersions (e.g. organic inorganic orhybrid nanoparticle suspensions). The characterization implies determination of size,morphology, phase transitions, surface, interfacialand rheological properties.The group responsible of the service is member ofTECNIO (ACC1Ó, CIDEM/COPCA) and has beenawarded with a quality certificate (similar to ISO9001) by CIDEM (Generalitat de Catalunya).

SUPERVISING SCIENTISTSNÚRIA AZEMAR SAZATORNIL CONXITA SOLANS MARSÀ

TECHNICAL ASSISTANTSUSANA VÍLCHEZ MALDONADOMARÍA MARTÍNEZ RODRÍGUEZ

3DDLS Spectrometer

Size distributions of mixed micelle and vesicle dispersions by dynamic light scattering

Rheometer AR-G2 Variation of elastic (G’) and viscous (G’’)

moduli as a frequencyfunction

� Electrophoretic mobility

Determination of Zeta potential of chargedparticles

Zetasizer Nano Z

Variation of Zeta potential as a function of pH


A) MONOCLONAL ANTIBODY DEVELOPMENTThe standard service includes: 1. Discussion of the project (screening system,selection criteria, etc.) and planning the work. 2. Immunization, cell fusion, screening andcloning: After their fusion with myeloma cellsscreening of the best hybridomas will beperformed by ELISA using previously suppliedantigen. Specific clones will be subcloned bylimiting dilution. 3. The customer will receive two cryovials and 10ml of culture supernatant of each positive clone.

B) POLYCLONAL ANTIBODY DEVELOPMENTThe standard service includes: 1. Discussion of the details of the project includingfeatures such as the type of immunogen, the finalproperties of the antibodies, and the species andnumber of animals used. 2. Immunization protocol: As accorded by thecustomer. 3. Isolation of the antiserum

4. ELISA testing: samples obtained on eachboosting injection and the final antisera will betested against the antigen following the criteriaagreed upon in the previous discussion with thecostumer. The costumer will receive 60-80 mL ofthe final serum from each rabbit and about 5 mLsamples of the pre-immune serum, and the bloodextractions made during the immunizationprotocol after each boosting injection.

C) ADDITIONAL SERVICES:1. Preparation of bioconjugates: labelledantibodies, haptenized proteins and enzymes,biotynilated and fluorescent probes, goldnanoparticle conjugates, etc. 2. Antibody purification. 3. Development of immunochemical methods:ELISA, immunoaffinity columns, etc. 4. Antibody characterization (Isotyping). 5. Hybridoma cryopreservation. 6. Mycoplasma testing.

95

Custom Antibody ServiceThe CAbS is a joint facility established under theumbrella of the IQAC-CSIC and CIBER-BBN. Thefacility wants to offer a high quality service forcustomized monoclonal and polyclonal antibodyproduction against many types of antigensincluding proteins, peptides or small organic molecules.Moreover, CAbS can offer additional services related tothe preparation of immunoreagents and developmentof immunochemical methods and protocols.

STAFFMª PILAR MARCO COLÁS (SUPERVISING SCIENTIST)NURIA PASCUAL DURAN (TECHNICAL DIRECTOR)MARTA RUIZ ARRIBASANA GONZÁLEZ GONZÁLEZ

Unless otherwise stated in a signed agreement, the property of immuno (bio) reagents produced orsynthesized and the results obtained regarding establishment of immunochemical methods and procedureswill belong to the costumer

Detailed description of the services and features provided by CAbS


The Organic Microanalysis Service providesmicro-determination of total carbon, hydrogen,nitrogen, sulphur, oxygen (C, H, N, S, O) andhalogens present in a wide range of organic andinorganic compounds. Since March 1999, Microanalysis Service has beenaccredited by ENAC, under EN45001 regulation.This was the first accredited elementalmicroanalysis by the CSIC and the first to beaccredited in Spain.As of November 2001, this Service has beenaccredited under regulation UNE-EN ISO/IEC 17025for analysis of CHNS. Accredited by ENAC: Certificate number159/LE319

Biodegradation and Aquatic Toxicity ServiceThe Biodegradation and Aquatic Toxicity Service ofthe IQAC offers a full range of standardized testmethods (OECD technical guidelines) for theassessment of the biodegradability and toxicity oforganic compounds in the aquatic environment.

This service carries out biodegradation and aquatictoxicity tests for internal use and for external clientsfrom industry, public administration, universities,and research organisms. Suitable technology andan expert and qualified staff guarantee theavailability of results.

STAFFMARÍA TERESA GARCÍA RAMÓN (CONTACTINGPERSON)ISABEL MUÑOZ LIRÓN ROSA MARÍA SALVIA PEIRÓ

STAFFPILAR DOMÈNECH DURAN (CONTACTING PERSON) MARIA TERESA VILA TERRADESNURIA BARRERA DE PAZ ANA DOMENECH DURAN

Organic Microanalysis Service

96

EquipmentThis facility has the appropriate instruments foraccurate sample analysis. Primary Instruments:1 Elemental Microanalyzer (A5) model Flash 1112,for C,H,N determination.1 Elemental Microanalyzer for O determination.1 Elemental Microanalyzer (A7) for C,H,N,Sdetermination.

1 Perkin-Elmer Microscale (B2) model AD6.2 Mettler Microscale (B3 and B4) models MT5and MX5.1 Metrohm Titrando model 808 for Cl,Br,I and F


The Magnetic ResonanceService is a researchsupport facility for theIQAC, other universities

and public research organisms, as well as forprivate companies. To two types of spectroscopytechniques are available:

Nuclear Magnetic Resonance (NMR Unit): TheUnit provides access to the following state-of-the-art methodologies:- Structure elucidation and quality control insynthetic chemistry by solution 1D/2D-NMR.- NMR-based drug screening.

- NMR of cells, cell extracts, and metabolomics-by-NMR.- Diffusion experiments and DOSY.

Electronic Paramagnetic Resonance (EPR Unit):The electron paramagnetic resonance spectroscopy(EPR) or electron spin resonance (ESR) studies theinteraction of a paramagnetic species with theelectromagnetic radiation (microwave radiation) inthe presence of an external magnetic field andallows detecting and studying stable or transientparamagnetic species such as free radicals, sometransition metal ions and defects in materials.

Magnetic Resonance Service

97

STAFFYOLANDA PÉREZ RUIZ (NMR UNIT MANAGER)LLUÍS FAJARÍ AGUDO (EPR UNIT TECHNICALMANAGER)LLUÍS JULIÀ BARGÉS (EPR UNIT SCIENTIFICMANAGER)

TECHNICAL ASSISTANTSMONTSERRAT SINDREU GRAÑÉ AVENCIA DÍEZ ORTEGO

The NMR Unit has two Varian/Agilent Spectrometers:- Varian Mercury 400 MHz(9.3950 T) is the walk-upinstrument for automatedheteronuclear NMR.The spectrometer has aVNMRS console with DirectDigital receiver with Performa-I Z gradients and OneNMRprobe, which can be tunedautomatically to any nucleusbetween 15N and 31P withProTune System autotuning

and is using Agilent's Chempack pulse sequencessuitable for most routine measurements. Thisspectrometer delivers routine, rapid heteronuclear-detected spectra in automation (1H, 19F, 31P, 13C,11B, 15N, 29Si, 2H, 17O, 111Cd, 113Cd, 105Pd, 77Se,27Al, 119Sn and 195Pt). An automated 100-sample

changer (for standard 8” long/5 mm Ø NMR tubes)and VnmrJ3.2 software allow performing shortacquisitions and quick access to spectra during thedaytime hours (9 am to 7 pm), while longerexperiments such as 2D HSQC or HMBC aresubmitted to run overnight or week-ends.- Varian Inova 500 MHz (11.7440 T field strength)is used for kinetics, diffusion, drug discovery andvariable temperature experiments (besidesstandard experiments).The spectrometer is equipped with a two-channelInova console, Performa-II (60 G/cm) Z gradients,and an inverse detection AutoX probe. Is theinstrument of choice for more demanding samples,and is frequently used for the full characterizationof samples where tiny amounts of material areavailable. The 500 is using DOSY/Biopack pulsesequences and VnmrJ software 2.2D version.

Nuclear Magnetic Resonance Unit (NMR Unit)

Equipped with a BrukerEPR/ESR spectrometer EMX,with a microwave bridge ofX-band (~9 GHz) EMXpremium X, magnet of 10”

ER073 with a power supply of 12 KW ER083.The following accessories are available: Standard ordouble cavity; different container samples (quartztubes, quartz capillaries, cells, flat cells for tissue);liquid nitrogen dewar and variable temperatureaccessory: cryostat, liquid nitrogen transfer line(120 K – 373 K); intelligent temperature controlerITC 503S from Oxford Instruments; continuousflow cryostat system of liquid helium (4.2 K - 300

K); gas flow controllerfrom Oxford Instruments;high vacuum unit HP40B2from Vacuubrand; "in situ"radiation source of UV-vis.500 W Oriel pressuremercury lamp. Powersupply Newport 69910;Bruker software acquisition,processing and simulationspectra WINEPR andSimFonia.

Electronic Paramagnetic Resonance (EPR Unit)


The Skin Absorption Service deals with theknowledge and quantitation of the skin absorptionof a given compound applied topically. Using an invitro methodology officially accepted by the OCDE(2004), the distribution of a chemical in thedifferent skin compartments (stratum corneum,epidermis and dermis) can be detected andquantified. The studies of percutaneous absorptioncan be fundamentally of interest for thePharmaceutical, Cosmetic, Veterinary andChemical sectors.

STAFFJOSÉ LUIS PARRA JUEZ (SUPERVISING SCIENTIST,CONTACTING PERSON)CRISTINA ALONSO MERINOLAIA RUBIO TOLEDANO

Skin Efficacy Service

The Skin Efficacy Service deals with theexperimental design, evaluation and objectivediagnostic of the skin efficacy and tolerance ofcosmetic and dermatologic formulations topicallyapplied by the use of non-invasive biophysicaltechniques. Evaluation and diagnosis of otherkeratinized tissues such as human nails and hair.

STAFFLUISA CODERCH NEGRA (SUPERVISING SCIENTIST,CONTACTING PERSON)CLARA BARBA ALBANELL ISABEL YUSTE HERNÁNDEZ ESTITXU FERNÁNDEZ

Skin Absorption Service

98


SIMchem (service of Synthesis of High added valueMolecules) is a IQAC-CSIC research facility createdin 2009 to give chemical and synthetic support to(R+D+i) activities in industry, university and publicorganizations.

It is projected to fill the gap existingbetween custom synthesis performedby companies and the syntheticresearch groups in academy. Theservice is intended to give a syntheticsupport to research projects ofchemistry, biology, biomedicineand drug discovery by providingboth skilled personnel, instrumentaland laboratory, and taking advantageof the chemical and synthetic expertise of thedifferent groups present in the Institute.

The service will be devoted to the study ofsynthetic methodologies, the development ofsynthetic sequences and small scale synthesis of

high added value organic compounds (milligram togram). The type of compounds initially envisagedconsist in broad scope bioactive molecules,including drug candidates, pharmacologicaltools and molecules directed to chemical,biological or biophysical tests in R+D activities.

Another goal of the service is toimplement new efficient synthetictechnologies in the host Institute,which could be employed by theresearch groups present in the IQAC,or external users. A special effort willbe devoted to set up high safetymethods of synthesis that couldimprove current laboratory practices

in the Institute and reach a high level ofcompetence and efficiency. SIMchem plans toreach the state-of-the-art in synthetic andpreparative purification technologies that, ingeneral, wouldn't be available to individual groupsin the IQAC.

99

LINES OF EXPERTISEMedicinal chemistryHeterocyclic and condensation chemistry, multistage synthesis.Development and optimization of reactions and processesAnalytical support to organic synthesis

CONTACTSAMADEU LLEBARIA, PhDTel. (+34) 93 400 61 00 Ext. [email protected]

CARME SERRA, PhD Tel. (+34) 93 400 61 00 Ext. [email protected]

Synthesis of High Added Value Molecules Service

INSTRUMENTAL TECHNOLOGIES

SYNTHESISCarousel reaction station.Parallel synthesis station for

solution phase chemistry andsolid supported reagent basedsynthesis

Simultaneously heats/cools, stirsand reflux´s multiple samplesunder an inert atmosphere

Hydrogenation chamber

OTHER INSTRUMENTS and FACILITIESSystems for samples evaporation: Thermo FischerSpeedVac and Stuart Sample ConcentratorKarl Fisher analysisHydrogenation Lab (microscale, low pressure)Mass spectrometry

ANALYTICAL AND PURIFICATION TECHNIQUES Analytical and preparative HPLCAutomated flash and MPLC chromatography


TAS was formally founded in 1999, in order tomeet the growing needs in this field of existingresearch groups, currently in IQAC, and collaboratein the process of innovation and industrialdevelopment.

STAFFALBERT M. MANICH BOU, SUPERVISING SCIENTISTJOSEP CARILLA AUGUET, CONTACTING PERSONNURIA ÁLVAREZ MARCOS, TECHNICIAN

100

Thermal Analysis Service

The following techniques are available:- Differential scanning calorimetry DSC- Microdifferential scanning calorimetry - Thermogravimetric analysis TGA- Dynamic vapor sorption DVS- Thermomechanical analysis TMA

The SAXS-WAXS service provides measurementswith a variety of set ups for the determination ofstructural information of ordered and semi-orderedmaterials. The range of distances of interest falls inthe nanoscale domain (0.2-100 nm). It can allowdeterminations of size, space ordering,morphology, fractal dimension and total interfacialarea. The materials comprise surfactant solutions,microemulsions, liquid crystals, mesoporousmaterials, macromolecules in solution such asproteins or DNA, nanostructured films and anyconceivable material with electronic discontinuitiesin the above mentioned range. 1D and 2Ddetectors are available. GISAXS and GISAXSconfigurations are also possible.

STAFFRAMON PONS PONS, SUPERVISING SCIENTISTJORDI ESQUENA MORET, SUPERVISING SCIENTISTJAUME CAELLES BALCELLS

SAXS-WAXS Service


101

The Proteomics Service has been recently createdto provide support to IQAC and IDAEA researchersas well as other public and private organizations.The service is focused in the analysis ofbiomolecules (proteins, peptides, oligonucleotides,sugars ...) and large organic molecules (such aspolymers, dendrimers, polyphenols and othermacromolecules) by MALDI-TOF/TOF massspectrometry.

The Service also offers separation, quantification,identification and characterization of peptides andproteins in biological and biomedical systems usingtwo-dimensional electrophoresis and massspectrometry techniques.

STAFFCARME QUERO LÓPEZ, Ph.D.

Proteomics Service

Services1) Molecular mass determination by MALDI-TOF

mass spectrometry. 2) Identification of proteins by peptide mass

fingerprint.

3) Identification of proteins by peptide massfingerprint and peptide fragmentation by massspectrometry (MALDI-TOF/TOF).

4) Electrophoresis Separation of proteins by one-and two-dimensional electrophoresis.


Life SciencesCancerIQAC_006. Aminocyclitol derivatives to regulateimmune response by stimulation of natural killerT-cells.IQAC_018. Ceramide analogues as potential anti-tumour drugs.Inflammatory diseasesIQAC_009. Modified siRNAs for silencing TNF-gene expression to treat inflammatory diseases.IQAC_011. New siRNAs conjugated tohydrophobic molecules for silencing geneexpression in the treatment of inflammatorydiseases.IQAC_012. Optimization of the therapeuticpotential of siRNA by formation of complexeswith plasma components.Rare diseasesIQAC_008. New aminocyclitols for treatment ofGaucher disease.IQAC_013. New compounds for treatment ofGaucher disease.Immunology/adjuvantsIQAC_006. Aminocyclitol derivatives to regulateimmune response by stimulation of natural killerT-cells.

PainIQAC_022. Pain treatment based on TRPV1channel blockers.Eating disordersIQAC_021. Treatment of diseases related toeating disorders.AIDSIQAC_016. Peptides derived from hepatitis G virussequence for treatment of VIH.Medical diagnosisIQAC_002. Test for cancer diagnosis based in thequantification of acid ceramidase.IQAC_019. Test for early diagnosis of rheumatoidarthritis based on chimeric fibrin and filaggrinpeptides.IQAC_020. Test for early diagnosis of rheumatoidarthritis based on chimeric vimentin peptides.Drug deliveryIQAC_007. Bicosomes: bicelles encapsulated inliposomes and their application in dilutedsystems.IQAC_010. Novel macroporous or meso/macroporous biocompatible polymers withchemical and pharmaceutical applications.Pharmacological toolsIQAC_015. Galactosidase inhibitors aspharmacological tools.

102

Knowledge Transfer encompasses the systems andprocesses by which technology, expertise andskilled people are transferred between the researchenvironment (universities, centers and institutes)and the industry, commerce and public sectors tocontribute to prosperity and society’s benefit.

In the technology transfer process different aspectsmust be considered: identification of researchwhich has potential commercial interest,adequately protection by means of patents, etc,development of strategies to transfer and finalnegotiation with companies who can exploit thefinal technology.

STAFFISABEL MASIP Ph.D Deputy Vice-Presidency for Knowledge TransferKnowledge Transfer Manager

Knowledge Transfer

Technologies AvailableWe have available a wide range of technologies in human health, diagnostic tools, cosmetics, chemicaldevices, etc. and the know-how acquired by our researchers in different technological fields.Different collaborative approaches are offered, such as exclusive and non-exclusive patent licenses, andcollaborative research and contract research with industry based on patent licenses or in innovativetechnologies.


103

Chemical TechnologyBiosensorsIQAC_003. Three-dimensional biosensor fordetection of analytes in a biological sample.IQAC_004. Biosensor device for simultaneousdetection of several biological samples insolution. Food safety testsIQAC_014. New immunochemical method fordetermination of bromopropylate in wine.IQAC_017. Immunoassay to detect residualfluoroquinolone-type antibiotics in food.

Skin careIQAC_005. Internal wool lipid extracted withsupercritical fluids for application in cosmeticsand dermo-pharmaceutics.DyesIQAC_001. Ecological liposomic disperse dyes fortextile or paper dyeing.Characterisation DevicesIQAC_023. Kratky type X-ray scattering camerasmodified to work under controlled atmosphereconditions.


7APPENDIXES CONTENTS

LIBRO IQAC. Appendix1.pags.105 a 107.qxd:Maquetación 1 11/6/12 10:33 Página 105

Research funding 110Running and granted research projects fundingContracted research and other incomeFacilities funding

Granted research projects 115National research projectsEU projectsAACC fundingOther funding

Running funded research projects and contracts 119BCMM DepartmentBMC DepartmentCBN DepartmentCST Department

Patents 122

Ph. D. Thesis 126

Masters-D.E.A. 129

Academic activities 130

Invited conferences and Key lectures 132

Oral and poster contributions 138Abroad eventsEvents in Spain

Other activitiesCBN WorkshopsScience Week

APPENDIX 2. SCIENTIFIC OUTPUTPublications in ISI journals (journals in alphabetical order) 140

Publications in non-ISI journals (journals in alphabetical order) 151

Book Chapters 152

The contents of appendixes 1 and 2 are to be found in the CD version

107

APPENDIX 1. OTHER RESULTS AND EVENTS


Research funding 110Running and granted research projects fundingContracted research and other incomeFacilities funding

Granted Research Projects 115National research projectsEU projectsAACC fundingOther funding

Running funded research projects and contracts 119BCMM DepartmentBMC DepartmentCBN DepartmentCST Department

Patents 122

Ph. D. Thesis 126

Masters-D.E.A. 129

Academic activities 129

Invited Conferences and Key Lectures 130

Oral and poster contributions 132Abroad eventsEvents in Spain

Other activities 138CBN WorkshopsScience Week

Department of Chemical and Surfactants Technology (CST)

Department of Chemical and Biomolecular Nanotechnology (CBN)

Department of Biomedicinal Chemistry (BMC)

Department of Biological Chemistry and Molecular Modelling (BCMM)

8.1. APPENDIX 1. OTHER RESULTS AND EVENTS

LIBRO IQAC. Appendix1.pags. 109-138:Maquetación 1 11/6/12 10:34 Página 109

RESEARCH FUNDING

110

GRANTED AND RUNNING RESEARCH PROJECTS FUNDING

RunningGranted in

Funds in20092010

20102010

20102011

reference PI total 2010 total 2011

PET2008-0312 BUJONS 69.085,00 9.801,00

SAF2009-05589-E FABRIAS 50.000,00

SAF2008-00706 FABRIAS 13.200,00

AGL2009-13452-C02-01 GUERRERO 136.800,00 23.200,00

CTQ2008-01426 LLEBARIA 16.200,00

CTQ2010-20541C03-01 ERITJA 107.420,00

AGL2008-05578-C05-01 SÁNCHEZ 13.200,00

SAF2008-00048 MESSEGUER 10.800,00

CTQ2008-06536 ANGLADA 7.920,00

SAF2008-03082 GALVE 12.000,00

CTQ2009-14366-C02-02 ALFONSO 95.784,00 8.126,00

CTQ2009-08223 CREHUET 30.940,00 3.060,00

MAT2010-20324-C02-02 MANICH 32.800,00

CTM2009-07435 COT 91.000,00 9.000,00

CTQ2009-08347 MARSAL 127.150,00 5.850,00

CTQ2009-13969-C02-01 HARO 135.756,17 18.243,82

CTQ2010-20517-C02-02 ARSEQUELL 48.380,00

AGL2009-12374-C03-03 TORRES 153.900,00 26.100,00

CTQ2009-07359 CLAPES 81.225,00 13.775,00

BIO2009-07866-E CAMINAL 25.000,00

CTQ2007-60409 LÓPEZ 4.530,00

CTQ2010-16964 LÓPEZ 68.060,00

CTQ2009-13967-C03-01 CODERCH 104.310,00 17.690,00

CTQ2010-14897 PONS 45.100,00

CTQ2008-01979 R. ABREU 14.040,00

CTQ2009-14151-C02-01 PÉREZ 49.140,00 4.860,00

CTQ2007-60364 GARCÍA 5.100,00

CTQ2010-17990 GARCÍA 20.000,00

CTQ2008-06892-C03-01 ESQUENA 11.052,12

ENIAC-2010-1202/

PLE-2009-0168 MARCO 214.081,00 41.202,24 Pr. CAJAL4EU

PERG05-GA-2009-249310 TORRENT 33.750

CSD2008-00005 MESSEGUER 37.600,00 37.600,00 CONSOLIDER

TRA2009_0282 CODERCH 37.006,85 25.050,00 PROVITAL

IPT-300000-2010-026 ESQUENA 75.941,54INNPACTO/ UNITEX S.A.

AIB2010DE-00405 CLAPES 7.376,00Acc.Int. ALEMANIA

IT2009-0067 HARO 9.750,00 Acc.Int. ITALIA

EUI2008-00175 MARCO 33.858,00 7.942,00

1.624.178,14 656.577,60


111


RunningGranted in

Funds in20092010

20102010

20102011


PIM2010EEI-00607 CLAPES 65.780,00

ELISHA MARCO 33.656,31

CONFFIDENCE MARCO 14.147,84 2.994,78

NANOITSELF ESQUENA 16.830,00

NANO3D ERITJA 10.030,04

DYNAMO ERITJA 17.747,35 49.080,33

FUNMOL ERITJA 108.809,73

MULTIFUN ERITJA 87.517,08

MULTIFUN SOLANS 87.517,08

INFORM SOLANS 25.274,37

NANOLYSE SOLANS 32.641,22

91.396,45 460.629,68

2009SGR1072 FABRIAS 8.944 8.944

2009SGR1212 PARRA 10.816 10.816

2009SGR1331 INFANTE 9.568 9.568

2009SGR1343 MARCO 14.144 14.144

2009SGR1472 OLIVELLA 8.736 8.736

2009SGR871 GUERRERO 7.488 7.488

2009SGR961 SOLANS 9.984 9.984

2005SGR00207 MARCO 10.540,19

2005SGR00111 OLIVELLA 10.540,19

2005SGR00812 SOLANS/AZEMAR 6.651,59

2005SGR00066 PARRA 6.805,07

Marató TV3 (070332) MESSEGUER 24.897,37

Marató TV3 (070430) VALENCIA 26.092,60

Marató TV3 (070532) LLEBARIA 14.073,75

Marató TV3 (080530) ARSEQUELL 40.500,00

155.207,01 124.253,75


112


RunningGranted in

Funds in20092010

20102010

20102011


200880I034 ABAD 4.000,00

200880I081 GOMARA 18.000,00

200980I058 CREHUET 30.000,00

200980I119 MOLINA 30.000,00

2008TW0006 SOLANS/AZEMAR 7.800,00 Coop. TAIWAN

2009TW0031 SOLANS 32.500,00 44.500,00 Coop. TAIWAN

2009PT0067 INFANTE 3.300,00 4.950,00Coop. PORTUGAL

2009MA0034 COLL 174,65 2.200,00Coop.MARRUECOS

2010IT0040 MARCO 4.000,00 Acc.Int ITALIA

2010CR0011 TORRES 11.000,00Acc.Int. COSTARICA

2011CU0003 HARO 15.800,00 Coop.CUBA

RYC-2010-06750 GIMENO 15.000,00

AGAUR A R. GHIDONI FABRIAS 4.057,00

JCLACAL FABRIAS 11.790,00 11.025,00

ORG. CONGRESO MESSEGUER 1.500,00

ORG. CONGRESO MANICH 3.000,00

CENIT REIG 30.000,00

FORMACION JARA PÉREZ TORRES 6.000,00

BENEFICIOS PATENTE INFANTE 4.100,55

AYUDA BRADLEY SCHMELKA ESQUENA 1.155,00

AYUDA GELEN RODRÍGUEZ DE LA MAZA 2.950,00

UNIDAD DE CALIDAD DE LA MAZA 600,00

MÁSTER QUÍMICA TORRES 562,50

232.121,65 117.843,05


113

CONTRACTED RESEARCH AND OTHER INCOME

CONTRACTS OTHER TOTAL

2010 2011 2010 2011

MatreyaPreparados Alimenticios

TCDBioibérica

252,72 125,176.172,20

14.732,776.301,80 27.584,66

D.G. AragónSEDEQ

Coroebus

21.302

47.866,381.275,26

70.443,94

InterquimVarios

BoehringerOmnia

49.484,5415.490,72

26,767,70

50.592,9770.302,60

5.001,37

217.640,00

Sylentis 36.450,00 24.300,00 60.750,00

UnisensorPharmasan

63.180,00 35.175,1416.946,00

48,60115.394,74

Biosciences Allinky

Bionure55.080,00 53.460,00

17.840,82

1.620,00

128.000,82

PolygrasVarios

12.966,35 15.990,1363,97 7.274,10 36.294,55

Lipotec 4.050,00 4.050,00

FIPSE 17.226,00 40.586,00 57.812,00

Barnatron 1.539,90 1.539,90

Bioglane 31.860,00 31.860,00

Varios 7.045,36 7.045,36

Thrombotargets 972,00 972,00

URV 487,50 487,50

VariosUAB

5.112,00 1.194,4110.692,00 16.998,41

Procter&GambleFirmenichMalaysianSyngenta

VariosQCI

93.153,0239.936,0022.666,04

18.319,00

33.146,88

42.480,00

93.742,205.310,00

348.753,94

Varios 4.739,54 1.572,40 6.311,94

Varios 9.639,00 9.639,00

CESIFAgr. FENIX

Varios76.145,38 69.071,60

9.647,10

12.381,74 167.245,82

537.946,73 590.402,14 47.935,19 69.315,72 1.245.599,78


114

FACILITIES FUNDING

Internal financing External financing Other

2010 2011 2010 2011 income TOTAL

MS GCMS 11.091,00 2.865,00 13.956,00

MS (TOF) 19.286,00 28.835,00 1.000,68 371,79 49.493,47

SYNTHESIS 9.414,93 11.748,58 9.545,66 80.598,70 111.307,87

MICROANALYSIS 7.659,00 6.428,50 23.791,47 14.257,72 1.326,00 53.462,69

X RAY 4.296,44 7.636,42 11.932,86

LIGHT SCATTERING 2.076,00 2.165,00 731,25 8.679,15 13.651,40

CELL CULTURE 3.225,00 2.830,00 400,00 6.455,00

NMR 17.271,15 49.737,15 4.097,04 8.447,03 76.552,37

IR-UV-Pol 3.430,50 5.230,00 8.660,50

CABS 4.008,45 15.899,65 6.261,00 8.168,00 31.337,10

PROTEOMICS 2.934,00 3.500,00 6.434,00

EPR 1.270,00 1.625,00 2.895,00

CALORIMETRY 8.790,02 10.363,44 17.125,42 28.327,52 64.606,40

PERCUTANEOUS ABSORP. 19.075,5 19.075,50

94.752,49 148.863,74 62.952,52 167.925,41 1.326,00


115

GRANTED RESEARCH PROJECTS

MINISTERIO DE CIENCIA E INNOVACIÓN

SUBPROGRAMAS DE INVESTIGACIÓN FUNDAMENTAL NO ORIENTADA Y DE ACCIONES COMPLEMENTARIAS PARA PROYECTOS DE INVESTIGACIÓN FUNDAMENTAL

NO ORIENTADA ( )…

Reference PI Dpt. TITLE 1st year2nd year3rd year

TOTAL %FEDER

2010

AGL2009-12374-C03-03

TorresSimon,Josep Ll.

BCMM Mecanismo de acción de los ácidos gra-sos poliinsaturados de origen marino enel síndrome metabólico y sinergismo conpolifenoles e iminociclitoles.

154.638,0031.581,0031.581,00

217.800 50

AGL2009-13452-C02-01

GuerreroPerez,Angel

BCMM Desarrollo de antagonistas de feromonassexuales para un control biorracional deplagas de insectos. Actividad y estudiosenzimáticos.

146.047,0029.826,5029.826,50

205.700 50

BIO2009-07866-E

CaminalSaperas,Gloria

BCMM Biotecnología de materiales lignoceluló-sicos: Retos moleculares, enzimáticos yquímicos para su aplicación industrial ymedioambiental.

25.000,000,00

---

25.000 ---

CTM2009-07435

Cot Cosp,Jaume

CST Minimización de residuos industrialescolagénicos: Biopolímeros inteligentesen la ingeniería de tejidos.

99.220,0010.890,0010.890,00

121.000 0

CTQ2009-07359

ClapesSaborit,Pere

BCMM Estrategias quimo-enzimáticas para lasíntesis orientada a la diversidad.Adiciones aldólicas biocatalíticas en cas-cada para la preparación de nuevos pro-ductos bioactivos.

81.614,5016.667,7516.667,75

114.950 50

CTQ2009-08223

Crehuet, Ramon

BCMM Acoplamiento entre dinámica y catálisisen los enzimas. Desarrollo de métodos yestudios de la familia de la kinasa deNag y de las aldolasas de clase II.

33.734,803.702,603.702,60

41.140 0

CTQ2009-08347

MarsalMonge,Agusti

CST Tecnologías limpias en tenería:Aplicación de nuevos compuestos fungi-cidas medioambientalmente sostenibles.

144.202,608.363,708.363,70

160.930 0

CTQ2009-13967-C03-01

CoderchNegra, M. Lluisa

CST Encapsulación lípida/polimérica en laproducción de tejidos biofuncionales.

104.810,2021.404,9021.404,90

147.620 50

CTQ2009-13969-C02-01

HaroVillar, Isabel

BMC Péptidos sintéticos en el estudio de lacoinfección GBV-C/HGV y HIV.

139.501,4023.419,3023.419,30

186.340 50

CTQ2009-14151-C02-01

PerezMuñoz,Lourdes

CST Estudios orientados a mejorar la seguri-dad de sistemas tensioactivos catiónicosde lisina.

53.578,805.880,60

5.880,60

65.340 0

CTQ2009-14366-C02-02

AlfonsoRodriguezIgnacio

BCMM Química combinatoria (covalente) diná-mica aplicada a la preparación de recep-tores de aniones de interés biológico.

00.672,0012.584,0012.584,00

125.840 50

SAF2009-05589-E

FabriasDomingoGemma

BMC E-2-Hexadecenal: Un nuevo lípido bioac-tivo.

50.000,000,00

---

50.000 ---


SUBPROGRAMA DE FOMENTO DE LA COOPERACIÓN CIENTÍFICA INTERNACIONAL (FCCI)PLAN E TIPO ENIAC

Reference PI Dpt. TITLE Y. Euros

PLE2009-0168

Marco ColasPilar

CBN Chip architectures by joint associatedlabs for European diagnostics(CAJAL4EU).

3 214.081 20.785 P93.296 EJ

116

MINISTERIO DE CIENCIA E INNOVACIÓN

SUBPROGRAMAS DE INVESTIGACIÓN FUNDAMENTAL NO ORIENTADA

Reference PI Dpt. TITLE 1st year2nd year3rd year

TOTAL %FEDER

2011

CTQ2010-14897

Pons,Ramon

CST Control y aplicación de nanoestructu-ras formadas por sistemas tensioacti-vos cataniónicos biocompatibles.

38.599,0015.972,0011.979,00

66.550 0

CTQ2010-16964

Lopez,Olga

CST Diseño, estabilización y optimizaciónde nanoestructuras bicelares: aplica-ción en entornos diluídos y efectosobre las estructuras de la piel.

58.249,4024.103,2018.077,40

100.430 0

CTQ2010-20517-C02-02

ArsequellGemma

BMC Activación química con metales ymetaloides dirigida al acoplamiento c-c/c-heteroatomo y a la modificaciónde biomoléculas.

41.406,2017.133,6012.850,20

71.390 0

CTQ2010-20541-C03-01

Eritja,Ramon

CBN Estudios estructurales de biomoléculasde interes biomédico y tecnológico.

91.935,8038.042,4028.531,80

158.510 0

MAT2010-20324-C02-02

Manich,Albert

CST Composites de altas prestaciones denanopartículas cerámicas en fibras depoliéster: propiedades y aplicaciones.

28.072,0011.616,008.712,00

48.400 0

SUBPROGRAMA DE PROYECTOS DE INVESTIGACIÓN FUNDAMENTAL ORIENTADA A LATRANSMISIÓN DE CONOCIMIENTO A LA EMPRESA (TRACE)


TRA2009-02820

CoderchNegra,Mª Lluisa

CST Eficacia de antioxidantes en cabellohumano.

3 60.621 24.300 P25.800 EJ10.521 CI

CONVOCATORIA 2010 DEL SUBPROGRAMA INNPACTO

IPT-300000-2010-26

EsquenaMoret, Jordi

CBN Investigación y desarrollo de textilesde uso médico y/o terapéuticomediante procesos de funcionalizaciónsuperficial.

4 395.231 184.552,43 P173.920,80 EJ36.758,08 CI


117

AACC FUNDING

GEN. CAT.- CIRIT. Ajuts a Grups de Recerca Consolidats

Reference PI Dpt. GRUPO Y. Euros

2009SGR1072 Fabrias Domingo,Gemma

BMC Research Unit on Biologically ActiveMolecules (RUBAM).

5 44.720

2009SGR1212 Parra Juez, José Luis

CST Fisicoquímica i Estructuració Vesicular deLípids i Biopolímers Bacterians.

5 54.080

2009SGR1331 Infante Martínez-Pardo, Rosa

CST Tensioactius i Química Sostenible. 5 47.840

2009SGR1343 Marco Colas, Pilar

CBN Applied Molecular Receptors Group (AMRG). 5 70.720

2009SGR1472 Olivella Nello,Santiago

BCMM Química Teòrica i Computacional. 5 43.680

2009SGR871 Guerrero Pérez,Ángel

BCMM Unidad d'Ecologia Química (UCE). 5 42.640

2009SGR961 Solans Marsa,Concepción

CBN Tensioactius. 5 49.920

Gen. Cat. CIDEM

TECCIT 10-1-0054

Solans Marsa,Concepción

CBN Pla d'actuació al centre QCI (IQAC-CSIC) peral 2010.

1 10.000

EU PROJECTS


FP-7-NMP-2010-LARGE-4MULTIFUN

Eritja, R./Solans, C.

CBN Multifunctional nanotechnology forselective detection and treatment ofcancer.

3 298.057 134.304 P54.966 EJ

108.786 OV

NANOITSELF230810Proy. MarieCurie

EsquenaMoret, Jordi

CBN Advanced functional nanocompositesby cooperative self assembly.

3 61.200

NANOLYSE245162

SolansMarsa,Concepción

CBN Nanoparticles in food: Analyticalmethods for detection and characteri-sation.

3 40.297,8060.446,7037.608,50

FP7-ICT-ENIAC-120215

Marco ColasPilar

CBN Chip architectures by joint associatedlabs for european diagnostics(CAJAL4EU).

3 308.40051.503

256.897

PIM2010EEI-00607

ClapésSaborit Pedro

BCMM Tecnologia de microrreactores parareacciones enzimáticas de formaciónde enlaces carbono-carbono.

3 73.78027.37017.850

56.000 P63.000 EJ


118

OTHER FUNDING


AIB2010DE-00405

Clapés Pedro

BCMM Síntesis enzimática de aminoácidos no protei-nogénicos para conjugaciones bioortogona-les.

2 7.376

20100111INNOCASH(INC-0588)

Solans Concepción

CBN Síntesis de materiales inorgánicos nanoes-tructurados por el método de reacciones enmicroemulsiones de tipo aceite-en-agua.

10M 15.000

201080E117 LópezOlga

CST Diseño, estabilización y optimización denanoestructuras bicelares: aplicación enentornos diluídos y efecto sobre las estructu-ras de la piel.

5M 6.600

201080E111 LlebariaAmadeo

BMC Preparation of aminocyclitol substituted cera-mides.

1 39.500

201080E039 Pons, Ramón CST Síntesis y propiedades de diacyl glicero lípidosderivados de arginina.

4M 6.500

200980I119 MolinaRicardo

CBN Obtención de capas delgadas poliméricasmediante tecnología de plasma.

1 30.000

200980I058 CrehuetRamon

BCMM Métodos computacionales para el estudio delacoplamiento entre la catálisis y la dinámicaen los enzimas.

1 30.000

RYC-2010-06750

GimenoCiril

BCMM Multifunctional metal oxide nanocatalysts forfine chemicals production.

1 15.000


119

RUNNING FUNDED RESEARCH PROJECTS AND CONTRACTS

Department of Biological Chemistry and Molecular Modelling

(SUBPROGRAMA DE INVESTIGACIÓN FUNDAMENTAL NO ORIENTADA. CONVOCATORIA: 2008; 2007)

Preparación y evaluación de inhibidores de colina-quinasa con potencial actividad antitumoralMICINN (PET2008_0312)Principal Investigator: J. BujonsPartner: Translational Cancer Drugs Pharma S.L.2009-2011

Reacciones de oxidacion de interes en quimicaatmosferica, en quimica ambiental y en procesosbiologicos. Estudio teoricoPrincipal Investigator: J. M. Anglada CTQ2008-065362008-2010

Möbius aromaticity: a new challenge for computa-tional chemistryMarie Curie Reintegration Grant (PERG05-GA-2009-249310)Principal Investigator: M. Torrent Sucarrat2009-2012

Suport a Grups de Recerca Consolidats. Generalitat de Catalunya (2005SGR00111)Grup de Química Teòrica i ComputacionalCoordinator: S. Olivella 2006-2008

Apoyo tecnológico para el desarrollo del proceso yaplicaciones en relación con la patente“Chemoenzymatic process for the preparation ofiminocyclitols"BIOGLANE, S.L.N.E.Principal Investigator: J. L. Torres2009-2010

Control biorracional de plagas del géneroCoroebus MMA-CSIC (2006X0827)Principal Investigator: A. Guerrero 2006-2010

Estudio prospectivo de control integrado de acrídi-dos plaga mediante feromonas.Diputación General de Aragón (2007x0832)Principal Investigator: C. Quero 2007-2010

Department of Biomedicinal Chemistry

Diseño y sintesis de nuevos ciclitoles para el estu-dio de procesos de señalizacion, biosintesis y meta-bolismo mediados por esfingolipidosCTQ2008-01426Principal Investigator: A. LLebaria2008-2010

Dihidroceramida desaturasa, ceramidasa lisosomaly autofagia: nuevo modo de accion de algunosagentes antitumoralesSAF2008-00706Principal Investigator: G. Fabrias 2008-2010

Disseny racional, síntesi i caracterització d'anàlegsd'opiorfi¬na i M6G: vers un millor coneixementdels mecanismes del dolor.Fundació La Marató de TV3 (070430)Coordinator, Principal Investigator: G. Valencia2008 2010

Molecular bases of neuropathic pain: An integra-ted approach to analyze the role of Group-III meta-botropic glutamate receptors.Fundació La Marató de TV3 (070532)Principal Investigator: A. LLebaria2008-2010

Drug discovery for transthyretin cardiac amyloidosisFundació La Marató de TV3 (080530)Principal Investigator: G. Arsequell2009-2011

Estudio estructural de dominios peptídicos del GBvirus C con capacidad inhibitoria del HIV-1 y deaptámeros de RNA que se unen a la proteína prpPGE Acción Integrada con Italia (IT2009-0067)Principal Investigators: I. Haro, E. Ragg2009-2010

Estudios para la mejora de procedimientos indus-triales de síntesis.Boehringer Ingelheim España, S.A. 20080173Principal Investigator: A. Llebaria2008-2011

Estudios para el desarrollo de nuevos agentesantiinfecciososOmnia Molecular, SL. 20091229Principal Investigator: A. Llebaria2009-2011

Diseño, sintesis y estudio anti-hiv-1 de dominiospeptidicos del gb virus cFIPSE- Fund. Invest. Prevencion Sida. 20100379Principal Investigator: I. Haro2010-2013


120

Department of Chemical and Biomolecular Nanotechnology

Desarrollo y demostración de nuevas tecnologíaspara la detección de residuos de antibióticos deuso veterinario a lo largo de la cadena de produc-ción de alimentos de origen animal. Control yseguridad alimentaria (Detecta) MICINN (AGL2008-05578-C05-01) Principal Investigator: F. Sánchez-Baeza 2008-2010

Obtención por organización espontánea de nue-vos nanocompuestos híbridos orgánico-inorgáni-cos para aplicaciones avanzadas en recubrimientosmultifuncionales.MICINN (CTQ2008-01979)Principal Investigators: C. Rodríguez-Abreu, C.Solans 2008-2010

Obtención y caracterización de estructurasmeso/macroporosas a partir de emulsiones alta-mente concentradas: control de la porosidad dualy aplicaciones en medio ambiente. MICINN (CTQ2008-06892-C03-01)Coordinator/Principal Investigator: J. Esquena2008-2010

Microarray de epítopos: una herramienta para eldiagnóstico y la investigación de las respuestasalérgicas a antibióticos b-lactámicos (b-Array) MICINN (SAF2008-03082) Principal Investigator: R. Galve 2008-2010

Modulación química de rutas de señalización celu-lar de relevancia en enfermedades degenerativas:generación de cabezas de serie MEC/MICINN (SAF2008-00048)Principal Investigator: A. Messeguer2008-2010

Nanobioanalytical platforms for improved diagno-sis of infections caused by pathogens(Nanomediag) Plan Nacional de Internacionalización de la I+D(EUI2008-00175) Coordinator/Principal Investigator: J. Samitier(IBEC, Barcelona).Principal Investigator: M. P. Marco2009-2011

Electronic Immuno-Interfaces and SurfaceNanobiotechnology: A Heterodoxical ApproachEU NMP2-CT-2003-505485 (ELISHA)Principal Investigator: M. P. Marco2004-2006

Multi-scale formation of functional nanocrystal-molecule assemblies and architectures (FUNMOL).EC-STREP, Focused Research Project, NMP-2007-213382Coordinator: A. Quinn (Tyndall NMRC, Cork,Ireland)IQAC participant: R. Eritja2008-2011

Design and functionality of non-linear electroche-mical nanoscale devices (Dynamo).EC-STREP, NEST-2004-ADV 028669-1Coordinator: K. Kuntturi (Helsinki Institute ofTechnology, Finland).IQAC Participant Group Leader: R. Eritja2006-2009

Precision chemical nanoengineering: integratingtop-down and bottom-up methodologies for thefabrication of 3-D adaptive nanostructured archi-tectures (Nano-3D)EC STREP, NMP4-CT2005-014006Coordinator: J. Preece (U. Birmingham, UK)IQAC Participant Group Leader: R. Eritja 2005-2008

Advances in functional organic-inorganic nano-composites by cooperative self-assembly FP7-PEOPLE IRSES 2008 Coordinator/Principal Investigator: J. Esquena 2009-2011

CONtaminants in Food and Feed: InexpensiveDEtectioN for Control of Exposure (Conffidence).EC, VII- Framework Programme. Food, Agricultureand Fisheries and Biotechnology. Proposal No.: 211326 – CP (Collaborative Project)Coordinator/Principal Investigator: Jacob de Jong(RIKILT, The Netherlands)Participant Group Leader: M. P. Marco2008-2012

Intervenció farmacològica sobre el receptor TRPV1per atenuar el dolor crònicFundació Marato de TV3 (20080123)Coordinator: A. Ferrer-Montiel (U. of Elx)IQAC Principal Investigator: A. Messeguer2008-2010

The Spanish Ion Channel Initiative MICINN CSD2008-00005, Consolider Program IQAC Participant Group Leader: A. Messeguer2009-2013

Suport a Grups de Recerca Consolidats. Generalitat de Catalunya (2005SGR00812)Grup de TensioactiusPrincipal Investigator: C. Solans2006-2008


Suport a Grups de Recerca Consolidats Generalitat de Catalunya (2005SGR00207) Applied molecular receptor group Principal Investigator: M. P. Marco2006-2008

Fundamental studies of rubber latex characteriza-tion in film formation and adhesives.Malasyan Rubber Board. 20100079Principal Investigator: J. Esquena 2008-2011

Diseño y síntesis de análogos químicos de inhibi-dores de quinasas descubiertos por AllinkyAllinky Biopharma Principal Investigator: A. Messeguer 2009-2011

Surface coatings characterization20060256The Procter & Gamble CompanyPrincipal Investigator: C. Solans2005-2012

Phase behavior of surfactants and polymers offabric and hair care interest. 20090784The Procter & Gamble CompanyPrincipal Investigator: C. Solans2009-2013

Functional polyester materials for delivery of bioac-tives 20091269Firmenich S.A.Principal Investigator: C. Solans 2009-2011

Síntesis de materiales inorgánicos nanoestructura-dos por el método de reacciones en microemulsio-nes del tipo aceite en agua 20100111INNOCASH (FECYT-MICINN)Principal Investigator: C. Solans 2009-2010

Investigación en nuevos conceptos de carreterasmás seguras y sostenibles. CDTI (CENIT2007-1014)Coordinator: C.Cortés (I+D+I, Serviá Cantó,Girona)Principal Investigator: J. EsquenaPartner: FENIX AIE2007-2010

121

Department of Chemical and Surfactants Technology

Biodegradabilidad y toxicidad acuática de líquidosiónicos como alternativa a disolventes orgánicosconvencionalesMEC (CTQ2007-60364)Principal Investigator: M. T. García2007-2010

Comportamiento fásico de sistemas bicelares:influencia de la composición lipídicaMEC (CTQ2007-60409)Principal Investigator: O. Lopez Serrano2007-2010

Caracterización, propiedades y aplicaciones de lasfibras de poli(ácido láctico)MEC (MAT 2007-66569-C02-02)Coordinator: D. Cayuela (UPC)Subproject Principal Investigator: A. M. Manich 2007-2010

Contrato de licencia y explotación de la patenteES512643/ PI9500027Principal Investigator: M. R. Infante2002-2015

Biopolymer based surfactants – stabilization andfunctionalisation of particles and surfaces COST Action n. D36/0008/06 Coordinator: M. R. Infante2006-2010

Valoración objetiva de propiedades, condicionesde mantenimiento y reciclado de diversos tipos decesped artificial para optimizar sus prestaciones.20100088POLIGRAS IBÉRICA, S.A.Principal Investigator: A. M. Manich 2010-2012


122

PATENTS

2010 Spanish Priority Application

Reference Title Inventors Assignee

P201030298 Bicelas encapsuladas en liposo-mas y su aplicación en siste-más diluídos

Olga López, Alfonso de la Maza, GelenRodríguez, Laia Rubio, Lucyana Barbosa,Guadalupe Soria

CSIC

P201030533 Composiciones textiles conhidrogeles de quitosano

Jordi Esquena, Susana Vilchez, ConcepciónSolans, Jonathan Miras, Pilar Erra

CSIC, AITEX

P201030611 Derivados lipofílicos de ácidosnucleicos

Ramon Eritja, Sandra Milena Ocampo, JoséCarlos Perales, Santiago Grijalvo, Ana Aviño

CSIC, UB,CIBER-BBN

P201030614 Oligonucleótidos modificadoscomo reguladores de la expre-sión génica

Ramon Eritja, Alvaro Somoza, Sandra MilenaOcampo, Montserrat Terrazas, Brendan JohnManning, Ana Aviño, José Carlos Perales

CSIC, UB,CIBER-BBN

P201030629 Método de administración deoligonucleótidos

Ramon Eritja, Sandra Milena Ocampo, JoséCarlos Perales, Francesc Savier Blasco

CSIC, UB

P201031008 Método de diagnóstico de laenfermedad de Farber

Gemma Fabrias, Josefina Casas, ThierryLevade, Carmen Bedia, José Luis Abad,Antonio Delgado

CSIC, UB,INSERM

P201031437 Derivados de cromeno Almudena Perona Requena, Antonio JesusMorreale de Leon, Ángel MesseguerPeypoch, Esther Carrasco Romero, BalbinoJosé Alarcón Sánchez, Irene AzaharaArellano Rojo

CSIC

P201031496 Aminociclohexanos polihidroxi-lados y su uso para el trata-miento de enfermedades liso-somales

Amadeu Llebaria, Ana Trapero CSIC

P201031553 Aminociclitoles bicíclicos y suuso para el tratamiento deenfermedades lisosomales


P201031622 Derivados de pequeños ARNde interferencia y su uso

Ramon Eritja, Sandra Milena Ocampo, JoséCarlos Perales, Carolina Romero, EsterFernández

CSIC, UB,UAB

P201031642 Derivados de aminoetanol sus-tituidos en c2 y su uso comoantitumorales

Gemma Fabrias, Josefina Casas, FabioSimbari, Luz del Carmen Camacho, José LuisAbad, María Garrido, Antonio Delgado

CSIC, UB

P201031721 Haptenos e inmunoreactivos ysu uso en la obtención de anti-cuerpos de familia e inmuno-ensayos para quinolonas

Pilar Marco, Francisco José Sánchez, DanielGonzález

CSIC

P201031878 Éteres de hidroxitirosol Jesús Joglar, Pere Clapés, Rafael de La Torre,Magi Farré, Maribes Covas, Montserrat Fitó,Bruno Almeida, Fernando Rodríguez, JuanManuel Decars, Manuel Macías, MiguelRomero

CSIC; IMIM,IMABIS


123

2010 PCT Application


PCT/ES2010/070043

Procedimiento quimo-enzimáti-co para la síntesis de 1-deoxi-d-xilulosa

Pere Clapes, Jesus Joglar, Alda Lisa, AntonioCastillo, Carles Lozano

CSIC,Bioglane

PCT/ES2010/070135

Uso de un compuesto para eltratamiento de una lesión pro-ducida por una reperfusiónpost-isquémica

Ángel Messeguer, Ana María Planas, CSIC

PCT/ES2010/070164

Compuestos aminociclitoles,procedimiento de obtención yusos

Amadeu Llebaria, Antonio Delgado, CarmenBedia, Youssef Harrak, Angel Raul Castaño,Carolina Barra

CSIC, UB,UAB

PCT/ES2010/070198

Nuevos materiales poliméricosmacroporosos y meso/macro-porosos obtenidos en emulsionesaltamente concentradas


CSIC

PCT/ES2010/070210

Péptidos sintéticos de la proteí-na de envoltura E1 del GBvirus C / HGV y uso de los mis-mos como inhibidores del HIV

Isabel Haro, Maria José Gomara CSIC

PCT/ES2010/070209

Péptidos sintéticos de de laproteína de envoltura e2 delgb virus c / hgv y uso de losmismos como inhibidores delhiv

Isabel Haro, Maria José Gomara CSIC

PCT/ES2010/070224

Dispositivo para alojar unamuestra en el interior de unacámara de dispersión o difrac-ción de rayos X

Ramon Pons CSIC

PCT/ES2010/070387

Colorantes dispersos liposoma-dos

Meritxell Martí, Luisa Coderch, José LuisParra, Alfonso de la Maza

CSIC

PCT/IB10/022340

New 3-oxopiperazinium deriva-tives agonists of nerve growthfactor and their use as medica-ments

Angel Messeguer, Pablo Villoslada, JoaquimMesseguer, Gloria Navarro,

CSIC, IDIBAPS

PCT/IB10/022351

New peptoid agonists of nervegrowth factor and their use asmedicaments

Angel Messeguer, Pablo Villoslada, JoaquimMesseguer, Gloria Navarro, Beatriz Moreno

CSIC, IDIBAPS

PCT/ES2010/000211

Conjugado polimérico para eltratamiento de infeccionesbacterianas

Angel Messeguer, Enrique Pérez-Payá, MaraiJesús Vicent, Laura Cascales

CSIC, CIPF

PCT/ES2010/070732

Formulaciones de lipoaminoa-cidos cationicos con menorpoder hemolítico basadas en laformación de pares catanioni-cos

Ramon Pons, Aurora Pinazo, Neus Lozano,Luis Ignacio Rivas, Rosario Fernández-Reyes,Juan Roman Luque, Rosa Infante, CarmenMoran

CSIC

PCT/ES2010/070824

Sistema y procedimiento mul-tianalítico basado en medicio-nes impedimétricas

Pilar Marco, Javier Ramon Azcon, FranciscoJosé Sánchez, Andrei Bratov, NataliaAbramova, Andrey Ipatov

CSIC


124



PCT/ES2010/070842

Derivados de aminociclitoles,procedimiento de obtención yusos

Amadeu Llebaria, Josefina Casas, MeritxellEgido, Lucía Díaz, Jordi Bujons, AntonioDelgado

CSIC, UB

PCT/ES2010/070857

Derivados lipófilos como sur-factantes

Francisco Comelles, Juan Carlos Morales,José Luis Parra

CSIC

PCT/ES10/070854

Derivados de amida de ácidosgrasos con anfetaminas para eltratamiento de desórdenes ali-menticios

Jesús Joglar, Pere Clapes, Rafael de La Torre,Magi Farré, Maribes Covas, Montserrat Fitó,Bruno Almeida, Fernando Rodríguez, JuanManuel Decars, Manuel Macías, MiguelRomero

CSIC; IMIM,IMABIS

2010 LICENSED

Reference Title Inventors Aplicant

EP09169036 New 3-oxopiperazinium deriva-tives agonists of nerve growthfactor and their use as medica-ments

Ángel Messeguer, Pablo Villoslada, JoaquimMesseguer, Gloria Navarro

CSIC; IIBAPS

EP09169045 New peptoid agonists of nervegrowth factor and their use asmedicaments

Ángel Messeguer, Pablo Villoslada, JoaquimMesseguer, Gloria Navarro, Beatriz Moreno

CSIC; IIBAPS

2011 Spanish Priority Application


P201130537 Antagonistas de TRPV1 y sususos

Ángel Messeguer, Antonio Ferrer, AsiaFernández, J. Manuel González, CarlosBelmonte, Felix Viana, Ana Gomis,

CSIC, UMH, CIPF

P201131002 Epoxidos y aziridinas de ciclo-hexano relacionados estructu-ralmente con la galactosa comoinhibidores selectivos de galac-tosidasas

Amadeu Llebaria, Youssef Harrak CSIC

P201131119 Amidas de 2-amino-1,3-propa-nodioles y su uso como inhibi-dores de ceramidasas

Gemma Fabrias, Josefina Casas, Luz delCarmen Camacho Castillo, José Luis Abad,Antonio Delgado

CSIC, UB

P201131310 Polipéptidos quiméricos deriva-dos de la proteína vimentinacon utilidad para el diagnosticode la artritis reumatoide

Isabel Haro, Maria José Gomara, RaimonSanmartí

CSIC, FCRB

P201131432 Dispositivo para caracterizaciónde muestras por medio dedifracción o de dispersión derayos X

Ramon Pons CSIC

P201132064 Compuestos bicíclicos inhibido-res de APAF1

Angel Messeguer, Miriam Corredor, IgnacioAlfonso, Enrique Pérez-Payá, Mar Orzáez

CSIC, CIPF


125



PCT/ES2011/070128

Bicelas encapsuladas en lipo-somas y su aplicación en siste-mas diluidos

Olga López, Alfonso de la Maza, Gelen Rodríguez,Laia Rubio, Lucyana Barbosa, Guadalupe Soria,Ana Maria Planas

CSIC

PCT/ES2011/070216

Composiciones textiles conhidrogeles de quitosano


CSIC, AITEX

PCT/ES2011/070293

Derivados lipofílicos de ácidosnucleicos

Ramon Eritja, Sandra Milena Ocampo, José CarlosPerales, Santiago Grijalvo, Ana Aviño

CSIC, UB,CIBER-BBN

PCT/ES2011/070296.

Oligonucleótidos modificadoscomo reguladores de la expre-sión génica

Ramon Eritja, Alvaro Somoza, Sandra MilenaOcampo, Montserrat Terrazas, Brendan JohnManning, Ana Aviño, José Carlos Perales

CSIC, UB,CIBER-BBN

PCT/ES2011/070295

Método de administración deoligonucleótidos

Ramon Eritja, Sandra Milena Ocampo, José CarlosPerales, Francesc Xavier Blasco

CSIC, UB

PCT/ES2011/070444

Método de diagnóstico de laenfermedad de Farber

Gemma Fabrias, Josefina Casas, Thierry Levade,Carmen Bedia, José Luis Abad, Antonio Delgado

CSIC, UB,INSERM

PCT/ES2011/070506

Derivados de cromeno Almudena Perona, Antonio Jesús Morreale, ángelMesseguer Peypoch, Esther Carrasco Romero,Balbino José Alarcon, Irene Azahara

CSIC

PCT/ES2011/070695

Aminociclohexanos polihidro-xilados y su uso para el trata-miento de enfermedades liso-somales


PCT/ES2011/070729

Aminociclitoles bicíclicos y suuso para el tratamiento deenfermedades lisosomales


PCT/ES2011/070740

Derivados de pequeños ARNde interferencia y su uso

Ramon Eritja, Sandra Milena Ocampo, José CarlosPerales, Carolina Romero, Ester Fernández

CSIC, UB,UAB

PCT/ES2011/070800

Haptenos e inmunoreactivos ysu uso en la obtención de anti-cuerpos de familia e inmuno-ensayos para quinolonas

Pilar Marco, Francisco José Sánchez, DanielGonzález

CSIC

PCT/ES2011/070880

Éteres de hidroxitirosol Jesús Joglar, Pere Clapés, Rafael de La Torre, MagíFarré, Maribel Covas, Montserrat Fitó, BrunoAlmeida, Fernando Rodríguez, Juan ManuelDecars, Manuel Macías, Miguel Romero

CSIC; IMIM,IMABIS

2011 LICENSED

Reference Title Inventors Aplicant

P200701253 Impedimentric sensor andapplications thereof

Pilar Marco, Javier Ramon Azcon, Francisco JoséSánchez, Andrei Bratov, Natalia Abramova, CarlosDomínguez , Ángel Merlos

CSIC

P200931164 Sistema y procedimiento mul-tianalítico basado en medicio-nes impedimétricas

Pilar Marco, Javier Ramon Azcón, Francisco JoséSánchez, Andrei Bratov, Natalia Abramova,Andrey Ipatov

CSIC


126

Ph. D. THESISAurora Colomer Flores. Dpt. de Tecnologia Química i de TensioactiusSíntesis y propiedades de nuevostensioactivos catiónicos derivados de lisina Directors: Aurora Pinazo Gassol, Maria LourdesPerez Muñoz21/12/2011. UB. Facultat de Química. Dpt.Ingenieria Química. Sobresaliente "cum laude"

Carolina Denise Aubery Torres. Dpt. de Nanotecnologia Química i BiomolecularNonionic water-in-oil and bicontinuousmicroemulsions as reaction media for thesynthesis of Mn-Zn ferrite nanoparticlesDirectors: Concepción Solans Marsa, MargaritaSanchez Dominguez14/11/2011. UB. Facultat de Química. Dpt.Ingenieria Química. Excel.lent "cum laude"

Mariana Gutiérrez Tejeda. Dpt. de Química Biològica i ModelitzacióMolecular.Aplicaciones sintéticas de aldolasas nativas ymodificadas genéticamente dependientes deglicina y compuestos alfa-hidroxicarbonílicos. Director: Pere Clapés Saborit. 10/11/2011. UB. Facultad de Farmacia. Dpt.Bioquímica y Biologia Molecular. Sobresaliente"cum laude"

Glòria Vendrell Navarro. Dpt. de Nanotecnologia Química i BiomolecularEstudis sobre la preparació, l’anàlisi i elcribratge de quimioteques depeptidomimèticsDirector: Àngel Messeguer Peypoch.9/11/2011. UB. Facultat de Química. Dpt.Química Orgánica. Excel.lent "cum laude"

Fabio M.M. Simbari. Dpt. de Química BiomèdicaMolecular tools for studyingsphingomyelinases and dihydroceramidedesaturaseDirector: Josefina Casas Brugulat5/10/2011. UB. Facultat de Biologia. Excel.lent "cum laude"

Raquel Obregón Núñez. Dpt. de Nanotecnologia Química i BiomolecularNuevas metodologías racionales para eldesarrollo de aplicaciones de polímeros dehuella molecular para la determinación deantibióticos en alimentos.Directores: Francisco José Sánchez Baeza, MariaPilar Marco Colás.29/09/2011. UB. Facultat de Química. Dpt.Química Analítica. Sobresaliente "cum laude"

Gerard Carot Sans. Dpt. de Química Biològica i ModelitzacióMolecular.Identificació i caracterització dels enzimsimplicats en la biosíntesi i degradació deferomones en lepidòpters nocturnsDirectors: Angel Guerrero Perez, Gloria RosellPellise.14/07/2011. UB. Facultat de Biologia, Dpt.Bioquímica y Biologia Molecular. Excel.lent "cumlaude"

Jordi Morros Camps. Dpt. de Tecnologia Química i de TensioactiusObtenció de tensioactius biopolimèrics basatsen la inulina en medi aquósDirectors: M. Rosa Infante Martínez-Pardo,Ramon Pons Pons. 04/07/2011. UB. Facultat de Química. Dpt.Ingenieria Química. Excel.lent

Clara Barba Albanell. Dpt. de Tecnologia Química i de TensioactiusEfectividad cosmética de proteínasqueratínicasDirectores: M. Luisa Coderch Negra, José LuisParra Juez01/07/2011. UB. Facultat de Farmacia. Dpt.Fisicoquimica.Sobresaliente "cum laude"

M. Jesús Sánchez-Martin. Dpt. de Química BiomèdicaEstudios biofísicos de péptidos sintéticos dela proteína de envoltura E1 del GBH-C/HGV ysu relación con el VIHDirectores: M. Asunción Alsina Esteller, IsabelHaro Villar04/07/2011. UB. Facultat Farmàcia, Dpt.Fisicoquímica.Sobresaliente "cum laude"

Benjamí Fürstenau. Dpt. de Química Biològica y ModelitzacióMolecular.Comunicación química interespecífica deCoroebus spp. (Coleoptera: Buprestidae) yDociostaurus maroccanus (Orthoptera:Acrididae), dos insectos plaga de la PenínsulaIbéricaDirectores: Angel Guerrero Pérez, Glòria RosellPellise10/06/2011. UB. Facultat de Biologia. Sobresaliente "cum laude"

José M Muñoz Olaya. Dpt. de Química BiomèdicaDihydroceramide desaturase as therapeutictarget in HIV-1 infection and cancerDirector: Gemma Fabriàs Domingo23/05/2011. UB. Facultat de Farmacia. DptGenetica. Sobresaliente "cum laude"


127

Lucía Díaz BuenoDpt. de Química BiomèdicaApplications of click chemistry and molecularmodeling to the development ofpharmacological chaperones for GaucherdeseaseDirector: Antonio Delgado Cirilo15/04/2011. UB. Facultad de Farmacia. Dpt.Farmacología y Química Terapéutica.Sobresaliente "cum laude"

Luz del Carmen Camacho Castillo. Dpt. de Química BiomèdicaAcid ceramidase and sphingosine-1-phosphate-lyase as biomarkers andtherapeutic targets in cancerDirector: Gemma Fabriàs Domingo31/03/2011. UB. Facultat de Farmacia. DptGenetica. Sobresaliente "cum laude"

Genoveva Morral Ruiz. Dpt. de Nanotecnologia Química i BiomolecularEstudi de la formació de nanoparticulespolimériques obtingudes a parti de nano-emulsions de fase externa aquosa i associaciód'antinflamatoris no esteroidalsDirectors: Concepción Solans Marsa, Maria JoséGarcia Celma15/03/2011. UB. Facultat de Farmacia. Dpt.Fisicoquímica. Sobresaliente "cum laude"

Bruno Almeida Cotrim. Dpt. de Química Biològica i ModelitzacióMolecular Synthesis of fatty acid derivatives of catecholcompounds that exhibit negative modulationof food intake and antioxidant properties Directors: Rafael de la Torre Fornell, Jesús JoglarTamargo10/01/2011. UPF. Facultad de Ciencias de la Saludy de la VidaSobresaliente

Sandra M. Ocampo. Dpt. de Nanotecnologia Química i BiomolecularDiseño y formulación de siRNAs para terapiaanti-inflamatoriaDirectors: Ramon Eritja Casadella, José CarlosPerales Losa17/12/2010. UB. Facultat de Medicina. Dpt.Ciencias Fisiológicas II.Sobresaliente "cum laude"

Ariadna Selga Pérez. Dpt. de Química Biològica i ModelitzacióMolecularObtenció de tio-conjugats de flavanols apartir de subproductes agroforestals. Anàlisi,síntesi, escalat, activitat i metabolitzacióDirectors: M. Pilar Vinardell Martínez Hidalgo,Josep Lluis Torres Simon03/12/2010. UB. Facultat de Farmàcia. Dpt.Bioquímica y Biologia Molecular. Excel.lent "cumlaude"

Jon Vilasau Sarobe. Dpt. de Nanotecnologia Química i BiomolecularInfluencia del comportamiento fásico desistemas agua/tensioactivo y del proceso deemulsificación en las propiedades deemulsiones de parafinaDirectors:Jordi Esquena Moret, Concepción SolansMarsa02/12/2010. UB. Facultat de Química. Sobresaliente "cum laude"

Margarita Alvira.Dpt. de Nanotecnologia Química i BiomolecularModified oligonucleotides for triple helixstudies and for the obtention of structureswith biomedical and technological interestDirector: Ramon Eritja Casadella26/10/2010. UB. Facultat de Química. Excel.lent "cum laude"

Juan Miguel Puertas Pérez. Dpt. de Química Biològica i ModelitzacióMolecularGenetic and process strategies for theproduction of recombinantmatallocarboxypeptidase inhibitors inEscherichia coliDirectors: Gloria Caminal Saperas, GloriaGonzález Amador08/10/2010. UAB. Dpt. Ingenieria Química. Excel.lent "cum laude"

Xavier Garrabou Pi. Dpt. de Química Biològica i ModelitzacióMolecularNew developments in the asymmetric carbon-carbon bond formation catalyzed byaldolasesDirectors: Pere Clapés Saborit, Jesús JoglarTamargo i Jordi Bujons Vilas30/07/2010. UB. Facultat de Farmàcia. Dpt.Bioquímica y Biologia Molecular. Excel.lent "cumlaude"

Esther R. Chamorro. Dpt. de Química Biològica i ModelitzacióMolecularEstudio conformacional y electrónico de laferomona sexual de la procesionaria del pino,acetato de (Z)-13-hexadecen-11-inilo y susanálogos. Relación estructura/actividadferomonalDirectors: Nélida Peruchena, Angel GuerreroPérez17/06/2010. Universidad del Nordeste(Argentina). Sobresaliente


128

Cristina Alonso Merino. Dpt. de Tecnologia Química i de TensioactiusAplicación tópica de polifenoles. Evaluaciónde su absorción percutánea y capacidadantioxidante mediante medotologías in vitro yex vivoDirectors: José Luis Parra Juez, M. Luisa CoderchNegra15/06/2010. UB. Facultat de Farmàcia. Dpt.Farmacia y Tecnologia Farmacéutica. Sobresaliente"cum laude"

Meritxell Llinàs Pons. Dpt. Nanotecnologia Química i BiomolecularEstudi d'emulsions altament concentradescom a sistemes d'alliberació controlada deprincipis actiusDirectors: Gabriela Caldero Linnhoff, ConcepciónSolans Marsa, Maria José Garcia Celma28/05/2010. UB. Facultat de Química. Dpt.Ingenieria Química. Excel.lent "cum laude"

Sonia Castellanos Ortega. Dpt. de Química Biològica i ModelitzacióMolecularRadical and non-radical carbazole derivativesfor molecular electronicsDirectors: Luis Juliá Bargès, Francisco LópezCalahorra20/05/2010. UB. Facultat de Química. Dpt.Química Orgánica. Excel.lent "cum laude"

Brendan Manning. Dpt. de Nanotecnologia Química i BiomolecularPhotopattering of surfaces using photolabilehairpin oligonucleotidesDirector: Ramon Eritja Casadella13/05/2010. UB. Facultat de Química. Apto

Aurora Jiménez Rodríguez. Dpt. de Química Biològica i ModelitzacióMolecularModelització d'aldolases de classse II: paperdel metall en el mecanisme catalític i enl'acoblament entre dinàmica i catàlisiDirector: Ramon Crehuet Simon25/03/2010. UB. Facultat de Química. Dpt.Química Física. Excel.lent "cum laude"

Neus Lozano Valdés. Dpt. de Tecnologia Química i de TensioactiusTensioactius sintétics biocompatibles:potencial aplicació en medicina pulmonarDirectors: Aurora Pinazo Gassol, Ramon PonsPons24/02/2010. UB. Facultat de Química. Excel.lent "cum laude"

Elena Herrera Carrillo. Dpto. Química BiomédicaPéptidos sintéticos derivados de la proteínaE2 del GB virus C como nuevos inhibidoresdel VIH-1Directors: María Jose Gomara Elena, Isabel HaroVillar23/02/2010. UB. Facultat de Farmacia. Dpt.Fisicoquímica. Sobresaliente "cum laude"


129

MASTER-D.E.A.

Experimental techniques in BiophysicsM. Pilar Marco ColasMaster de Biofisica (UB) 07/12/2010

Técnicas experimentales en BiofísicaRamon Eritja CasadellaPrograma de Doctorat de Física (UB) 03/12/2010

Biocatalytic carbonication cascade reactions forasymmetric synthesisPedro Clapes SaboritMaster de Biotecnologia Molecular (UB)23/11/2010

Electrónica molecular. Materiales. Procesosconductores orgánicosLuis Julia BargesMaster de Nanomateriales y Nanotecnología deTransferencia Electrónica (UB) 15/11/2010

Técnicas básicasRamon Eritja CasadellaPrograma de Doctorat de Biotecnología (UB)11/10/2010

Terapia génicaRamon Eritja CasadellaPrograma de Doctorat de Biomedicina (UB)31/05/2010

Applications in BiotechologyJosep Lluís Torres SimonPrograma de Doctorat de Biotecnología (UB)21/04/2010

Tensioactivos y polímeros en sistemas coloidalesJordi Esquena MoretMaster de Química Avanzada (UB) 25/02/2010

Estadística aplicada a la preformulación yformulación de medicamentosAlbert María Manich BouLicenciatura / Grado Especialista en FarmaciaIndustrial y Galénica (UB) 15/02/2010

Química supramolecularIgnacio Alfonso RodríguezMáster en Química Sostenible. Universitat JaumeI. 11/01/2010

Introduction to small angle X-ray scatteringtechnique and the organization of skin-collagenmolecules and other examplesOlga López SerranoSincroton Radiation Master (UAB). 11/01/2010

Biohybrid materials and biofunctional surfaces:Recent progress towards improved diagnostics.Pilar MarcoPrograma de Doctorat de Química Orgànica (UB).2/11/2011

Python applied to computational chemistry andmolecular modellingRamon Crehuet SimonXarxa de Recerca en Química Teòrica iComputacional Xarxa de Referència de Química Teòrica iComputacional Summer School. 28/06/2010

Jonathan Miras HernándezAplicación de hidrogeles de Poli(N-isopropilacrilamida) en tejidos de poliamidaDirectores: Jordi Esquena, Susana VilchezUniversidad de Barcelona, Facultad de Química02-03-2010

Gelen Rodríguez DelgadoEfecto de las bicelas sobre los lípidos delestrato corneo de la pielDirectores: Olga LópezUniversidad de Barcelona, Facultad de Química30/06/2010

Manroshan SinghInfluence of hydrophobically modifiedpolyfructose (HMP) on the stability ofvulcanizad natural rubber latexDirectores: Jordi Esquena, Conxita Solans,Tharwat TadrosUniversidad de Barcelona, Facultad de Química07/2010

Clotilde BouaoudFormulation of fluorescent polymericnanoparticles from O/W nano-emulsionsDirectores: Gabriela Calderó, Conxita SolansMaster Chimie et Ingénierie de la Formulation(CIF). Ecole Nationale Supérieure de Chimie Lille(France). Sciences de la Matière 2010

Anna Cornellas PitarchLíquids iònics derivats d'imidazoli i piridini:síntesi, autoagregació, toxicitat aquàtica iactivitat antimicrobianaDirectores: Mª Teresa García, Lourdes PérezIQAC-CSIC25- 01- 2011

Marta Escarrà SenmartíPèptids sintètics derivats de la proteïna E2 delGB virus C com a possibles inhibidors de l’HIV-1Directoras: Isabel Haro y María José GómaraMaster en Química Orgánica AvanzadaFacultad de Química, Universidad de Barcelona.31-01-2011

ACADEMIC ACTIVITIES


130

G. CalderóNanoparticles for biomedical applications:Preparation in O/W nano-emulsionsInt. Workshop on "Novel Nanotechnology andNanomaterials for Science and Human" (Taipei,Taiwan). KL. 24/11/2010.

G. CaminalSistema enzimático de Trametes versicolorimplicado en la degradación decontaminantes emergentesIII Congreso de Microbiología Industrial yBiotecnología Microbiana (Alcalá de Henares). KL.17/11/2010.

O. LópezNanomateriales y nuevas nanoestructuraslipidicas: Absorción percutáneaJornadas Científico Técnicas - Impacto de laNanotecnología en la Cosmética (SociedadEspañola de Químicos Cosméticos, Barcelona).KL. 11/11/2010.

M.R. InfanteBiocompatible cationic surfactants fromarginineSymposium in Honour of Prof. M.J. Rossen.University of New York (New York). 29/10/2010.

I. AlfonsoConstitutional dynamic chemistry withmacrocyclic pseudopeptides7th ERA-CHEMISTRY Flash Conference"Bioinspired Chemistry" (Santiago deCompostela) 26/10/2010.

A. GuerreroInhibición del catabolismo feromonal comonueva aproximación al control de plagas deinsectosCitefa-Conicet Control de Plagas e Insecticidas.(Buenos Aires). IC. 22/10/2010.

P. ClapésEl papel de la Academia a la hora de abrirnuevos mercados2º Congreso de Biotecnología y Empresa.Associació de Biotecnòlegs de Catalunya(Barcelona). 21/10/2010.

A. GuerreroInhibition of the chemical communication inInsectsChemical Communication in Insects. AsociaciónLatinoamericana de Ecología Química. (Coloniade Sacramento, Uruguay). IC. 20/10/2010.

R. EritjaSynthesis of modified oligonucleotidederivatives for biosensing applicationsWorkshop on Gold Modification and Aptamers(CICbiomaGUNE, San Sebastian). 4/10/2010.

F. FernándezBiofunctionalization of gold surfaces: Keyissues and applicationsWorkshop on Gold Modification and Aptamers(CICbiomaGUNE, San Sebastian). 4/10/2010.

P. ClapésEnzyme catalyzed asymmetric aldol additions:Carbohydrates and iminosugars from DHAPto unphoshorylated donor analoguesBIOTEC 2010 (5th Int. Meeting on Biotechnology.Sociedad Española de Biotecnología, Pamplona).29/9/2010.

INVITED CONFERENCES AND KEY LECTURES

SPECIALIZATIONTerapia genómica en BiomedicinaRamon Eritja Casadella 24/11/2010; 28/10/2010;22/06/2010Formación Continuada de Profesiones Sanitarias. Consorcio Centro de Investigación Biomédica enRed. Bioingenieria, Biomateriales y Nanomedicina(CIBER-BBN)

Análisis TermogravimétricoAlbert Maria Manich BouSeminario. T.A. Instruments 27/05/2010

Análisis térmico de fibras termofijadasAlbert María Manich BouEspecializacion en Análisis Térmico y Calorimetría. Grupo Especializado de Calorimetría y AnálisisTérmico (RSEQ-RSEF) 09/02/2010

Emulsiones y micro-emulsiones: preparación,propiedades y aplicaciones industrialesMaria José Garcia Celma 05/05/2010Jordi Esquena Moret 04/05/2010Concepción Solans Marsa 04/05/2010Especialitat de Quimica/Fisica de Materials.Colegio Químicos Cataluña

Prácticas de laboratorio en cosmética ydermofarmaciaJordi Esquena MoretMaster en Cosmética y Dermofarmacia. Centro de Estudios Superiores IndustriaFarmaceutica 24/04/2010


131

M.P. MarcoNew opportunities for diagnostics usingnanobiotechnological approachesNanospain Conf2010 (Malaga). KL. 24/07/2010.

M.P. MarcoNuevos enfoques para el análisis de residuosen alimentos utilizando anticuerpos ymicro(nano) sistemasKausal2010. IV Congreso Int. Autocontrol yAlimentos Inocuos para Proteger la Salud. KL.7/05/2010.

M.P. MarcoNuevas aproximacionesmicro(nano)biotecnológicas y biosensorespara incrementar la seguridad alimentariaSeguridad Alimentaria. Azti-Tecnalia. 7/05/2010.

M.P. MarcoBiofunctional surfaces: Selective sensing unitsfor diagnosticsBarcelona Innovation workshop:Nanobiotechnology (UAB Research Park).5/10/2010

M.P. MarcoNew developments and opportunities forcancer diagnostics using biosensorsClinical Applications of Nanotechnologies in theField of Cancer. Nanomedicine ETP Workshop(Montpellier, Francia). KL. 28/01/2010.

R. PonsSmall angle X-ray scattering as a tool for softmatter investigationFacultad de Farmacia, Universidad de Porto(Porto, Portugal). 8/11/2010

L. Pérez, A. Pinazo, M.R. InfanteBiocompatible surfactants from naturalresourcesSustainable Chemistry. Opening Doors, BritishCouncil-CSIC. (Avila). 6-10/03/2011

J. CotMinimization of collagenic waste: isolation ofhigh value-added biopolymersSustainable Chemistry. Opening Doors, BritishCouncil-CSIC. (Avila). 6-10/03/2011

Mª T. GarcíaBiodegradabilidad y toxicidad acuática delíquidos iónicos Sustainable Chemistry. Opening Doors, BritishCouncil-CSIC. (Avila), 6-10/03/2011

L. Pérez, A. Pinazo, M.R. InfanteBiobased surfactants from renewableresources102nd AOCS Annual Meeting and Expo.(Cincinnati, USA) 1-4/05/2011

Mª R. InfanteBio-based surfactants from renewableresourcesGreen Chemistry & the Consumer Symposium.(York, U.K.) 18/10/2011

Mª R. InfanteBio-based surfactants from renewableresources 58th SEPAWA Congress. (Fulda, Alemania)14/10/2011

J.L. ParraPerfil toxicológico y niveles de exposición delos cosméticosJornada EVIC Hispania. (Barcelona), 30/06/2011

L. Rubio, C Alonso, G. Rodríguez, M. Cocera, A.de la Maza, L Coderch, J.L. Parra, O. LópezBicellar systems as vehicle for impaired skinSkin Forum 12th Annual Meeting. (Frankfurt,Alemania)28-29/03/2011

O. López, G. Rodríguez, L. Barbosa Barros, L.Rubio, M. Cócera, A. de la Maza, J.L. ParraBicellar nanosystems as epidermal barrierfunction modulatorsEuropean Epidermal Barrier Research Network(E2BRN) (Barcelona), 07/09/2011


Colomer, L. Pérez, A. Pinazo, M.R. Infante, A.Mezei, R. PonsLysine based surfactants: Relationshipbetween chemical structure andadsorption/aggregation properties6/9/2011. 8th Liquid Matter Conference (Viena,Austria). Poster

R. Pons, I. Carrera, J. CaellesNascent nanoemulsions from microemulsiondilution6/9/2011. 8th Liquid Matter Conference (Viena,Austria). Poster

A.M. Manich, J. Carilla, R.A.L. Miguel, J. Lucas, F.Franco, L. Montero, D. CayuelaMechanical properties, relaxation behaviourand thermal characterization of false-twisttextured polyactide multifilament13/9/2010. 6th. Central European Conference2010. Fibre-Grade Polymers, Chemical Fibres andSpecial Textiles (Bratislava. Eslovaquia). Oral

J.M. AngladaThe reactivity of ozone versus the reactivityof carbonyl oxide. An analysis from atheoretical point of view.16/7/2010. RSC 21st. International Symposiumon Gas Kinetics (Leuwen, Bélgica). Oral

A.M. Manich, J. Carilla, B. Baena, D. CayuelaThermal stability and heat setting of PLAtextured filaments measured by DSC andTMA24-27/07/2011. 10th Mediterranean Conferenceon Calorimetry and Thermal Analysis MEDICTA2011 (Porto, Portugal). Poster

M. Ussman, D. López-Santana, J. Carilla, A.M.ManichCellulosic fibres and water sorption isotherms24-27/07/2011. 10th Mediterranean Conferenceon Calorimetry and Thermal Analysis MEDICTA(Porto, Portugal) Poster

M. Cócera, G. Rodríguez, L. Rubio, L. Barbosa-Barros, C. Sandt, P. Dumas, A. de la Maza, O. LópezFTIR and microscope with synchrotron lightto see bicellar systems in skin07-12/08/2011. Gordon Research Conference:Barrier Function of Mammalian Skin. (WatervilleValley, NH, USA). Poster

G. Rodríguez, M. Cócera, L. Rubio, C. Barba, L.Barbosa-Barros, C. Sandt, P. Dumas, A. de laMaza, O. LópezSubstituting dhpc for schol: bicellar systemsmilder for skin07-12/08/2011. Gordon Research Conference:Barrier Function of Mammalian Skin. (WatervilleValley, NH, USA) Poster

A. Moure, I. Alfonso.Pseudopeptidic molecular cages7/7/2011. 6th International Symposium onMacrocyclic and Supramolecular Chemistry (6-ISMSC) (Brighton, UK). Poster

S. Vílchez, A.M. Manich, J. Miras, R. Molina, P.Erra, J. EsquenaSurface modification of polyamide fabricswith chitosan hydrogels crosslinked withgenipin20-24/5/2011. 10th International Conference ofthe European Chitin Society (EUCHIS 2011) (S.Petersburgo, Rusia). Oral

J. Miras, S. Vílchez, C. Solans, J. Esquena Macroporous chitosan foams obtained in oil-in-water (O/W) highly concentratedemulsions20-24/5/2011. 10th International Conference ofthe European Chitin Society (EUCHIS 2011) (S. Petersburgo, Rusia). Poster

L.A. Pérez-Carrillo, S. Vílchez, C. Solans, J.EsquenaPreparation and characterization of highlyporous materials obtained by templating inwater-in-1,1-dichloroethene highlyconcentrated emulsions 3-6/5/2011. AMIDIQ (Academia Mexicana deInvestigación y Docencia en Ingeniería Química)(Riviera Maya, Quintana Roo, México). Poster

G. Rodríguez, L. Rubio, M. Cócera, A. de laMaza, O. López, C. Lopez-Iglesias, E. CollCryo-tem and freeze fracture tem in thestudy of bicellar systems8-10/06/2010. SCANDEM (Scandinavian Societyfor Electron Microscopy) (Estocolmo, Suecia).Poster

D. Cayuela, L.A. Montero and A.M. ManichVariation of microstructure of textured andfixed polylactide fibres with the texturingconditions3-6/10/2010. 5th International Textile, Clothingand Design Conference (Dubrovnik, Croacia). Oral

Advanced Materials and Nanotechnologyfor Sustainable Development (21-23/10/2011; Kathmandu, Nepal).R. Ramsch, C. Paulme, K. Pemartin, G. Calderó,M. Sánchez-Domínguez, C. SolansNanocomposites of superparamagnetic andbiocompatible polymeric nanoparticles. Oral

C. SolansNano-emulsions prepared by low-energymethods as templates for nano-biomaterials.Oral

132

ORAL AND POSTER CONTRIBUTIONS (ABROAD EVENTS)


J. Esquena.Preparation of nanostructured porousmaterials using highly concentratedemulsions as templates. Oral

Workshop on “Novel Nanotechnology andNanomaterials for “Science for Human””(21-22/11/2011; Taipei, Taiwan).C. SolansEmulsions as templates for the controlledpreparation nanometer-scale biomaterials.Oral

J. EsquenaPorous materials with controlled textureobtained in highly concentrated emulsions.Oral

M. M. AlamHigly concentrated w/o emulsions-templatefor carbonaceous porous materials. Oral

23rd Conference of the European Colloidand Interface Society (5-10/09/2010; Praga,Rep. Checa)N. Lozano, A. Pinazo, L. Pérez, C. La Mesa, R.Pons Diacyl aminoacid/diacyl phospholipidmixtures: catanionic and cationic vesicles.Poster

A. Colomer, L. Pérez, A. Pinazo, M.R. Infante, R.Pons Thermotropic and lyotropic phase behaviourof lysine based surfactants. Poster

G. Rodríguez, L. Rubio, M. Cócera, J. Estelrich, R.Pons, A. de la Maza, O. López. Changes in skin lipid arrangement by effectof bicelles. Poster

A. Colomer, L. Perez, R. Infante, R. Pons, A.PinazoLysine based surfactants: relationshipbetween chemical structure andadsorption/aggregation properties. Poster

4th Iberian Meeting on Colloids andInterfaces (RICI4) (13-15/7/2011; Oporto,Portugal). M. LLinàs, G.Caldero, M.J. García-Celma,K.Aramaki, C.SolansRelease of actives from O/W highlyconcentrated emulsions: Influence of thecontinuous phase nanostructure. Oral

N. Vilanova, C. Rodríguez-Abreu, C. SolansFormulation of multiple emulsions forproducing silicone porous microparticles. Oral

R. Ramsch, C. Paulme, K. Pemartin, G. Calderó,M. Sánchez-Domínguez, C. SolansBiocompatible polymeric nanoparticles forthe encapsulation of superparamagneticnanoparticles. Poster

A. Colomer, L. Pérez, A. Pinazo, M.R. Infante, A.Mezei, R. PonsLysine based surfactants: relationshipbetween chemical structure andadsorption/aggregation properties. Oral

Int. Conf. on Engineering UBI2011 (28-30/11/2011; Covilha, Portugal)V. Martínez, C. Alonso, A. de la Maza, M. Martí,L. CoderchSkin delivery of gallic acid from biofunctionalcotton fabric. Poster

M. Martí. C. Barba, J. Carilla, L. Coderch, A.Manich.Lipid extraction effect on moisturesorption/desorption of keratin fibres. Poster

A.M. Manich, D. López-SantanaEstudio de la influencia de las condicionesatmosféricas en la sensación térmica durantela práctica deportiva. Poster

A.M. Manich, B. Baena, D. López-Santana, M.Martí, J. Carilla, R.A.l. Miguel, J. Lucas, M.J.Santos Silva, D. CayuelaInfluencia del termofijado en las propiedadesmecánicas de los filamentos de PLA. Oral

NanoFormulation 2011 (26/6-1/7/2011;Singapore). S. Vílchez, L. Pérez-Carrillo, C. Solans, J. EsquenaHighly porous carbon materials obtained bytemplating in oil-in-alcohol highlyconcentrated emulsions. Poster.

N. Ahmad, R. Ramsch, M. Llinas, J. Esquena, C.Solans, R. Hashim, H. A. TajuddinCharacterization of ternarywater/oil/branched-chain glycoside systemsfor pharmacfeutical applications. Poster.

G. Calderó, S. Leitner, C. Bouaoud, M.J. García-Celma i C. Solans.Functionalised biocompatible nanoparticlepreparation from nano-emulsions. Poster.

25th Conference of the European Colloidand Interface Society (ECIS 2011) (4-9/09/2011; Berlin, Alemania)A. Vilchez, C. Rodríguez-Abreu, A. Menner, A.Bismarck, J. EsquenaMacroporous solid foams obtained in highlyconcentrated Pickering emulsions stabilizedwith magnetic nanoparticles. Oral

133


R. Ramsch, C. Paulme, K. Pemartin, G. Calderó,M. Sánchez-Domínguez, C. SolansNew approach for the encapsulation ofsuperparamagnetic nanoparticles in abiocompatible polymer. Poster

R. Ramsch, N. Ahmad,M. Llinas, R. Hashim, H. A.Tajuddin, J. Esquena, C. SolansBranched-chain glycolipids – versatile andbiocompatible amphiphiles for new drugcarrier systems. Oral

M. Sánchez-Domínguez, K. Pemartin, C. Tiseanu,J. Aguilar, V. Parvulescu, M. Boutonnet , C. SolansSynthesis of mixed and doped cerium oxidesby the oil-in-water microemulsion reactionmethod. Oral

K. Pemartin, H. Kusar, M. Sanchez-Dominguez,M. Boutonnet, C. SolansCuO-CeO2 and CuO-ZnO nanoparticlesprepared from a novel oil-in-water (O/W)microemulsion reaction method: their use ascatalyst in water-gas shift reaction. Poster

26th Congress IFSCC (20-23/09/2010;Buenos Aires, Argentina) L. Coderch, C. Barba, C. Alonso, M. Martí, J.L.Parra New antioxidant efficacy methods for humanhair. Poster

C. Barba, M. Martí, A. Roddick-Lanzilotta, A.Manich, J. Carilla, J.L. Parra and L. Coderch.Water sorption of hair and nails treated withwool keratin proteins and peptides. Poster

L. Coderch, S. Méndez, R. Ramírez, M. Martí, A.de la Maza, O. López, and J.L. ParraSkin and hair efficacy of internal wool lipidliposomes rich in ceramides. Poster

C. Alonso, M. Martí, V. Martínez, L. Rubio, L.Coderch and J.L. ParraCosmeto-textiles: skin assessment. Poster

13th European Student Colloid Conference(ESC2011) (14-17/06/2011; Falkenberg,Sweden)S. Leitner, G. Calderó, M. J. García-Celma, C.SolansCharacterizatioin of polymer in watercationic nano-emulsions and their use fornanoparticle preparation. Oral

S. Vílchez-Maldonado, G. Calderó, R. Molina Skin-care polymeric nanoparticles preparedfrom O/W nano-emulsions. Oral

C. Paulme, K. Pemartin, R. Ramsch, M. Sanchez,G. Caldero, C. SolansEncapsulation of magnetic nanoparticleswithin a biocompatible polymer. Poster

N. Vilanova, C. Rodriguez-Abreu, C. SolansNovel Synthesis of silicone porousmicroparticles by crosslinking multipleemulsions. Oral

J. Miras, S. Vílchez, J. Esquena, C. SolansPreparation and characterization of highlyconcentrated emulsions in the presence ofchitosan. Oral

4th Asian Conference on Colloid andInterface Science (ACCIS 2011) (23-26/11/2011; Tainan, Taiwan). C. SolansFormation of nano-emulsions by low-energymethods and application to the preparationof functional nanoparticles. Oral

J. EsquenaMacroporous foams obtained in highlyconcentrated Pickering emulsions stabilizedsolely with magnetic nanoparticles. Oral

M.M. AlamRheology of liquids crystals: Macroscopic tomicroscopic scale. Oral

12th International Conference“Perspectives in Percutaneous Penetration”(06-10/04/2010; La Grande Motte, Francia) L. Rubio, M. Martí, C. Alonso, V. Martínez, L.Coderch and J.L. ParraSkin delivery of a sun filter contained inbiofunctional textiles. Poster

G. Rodríguez, L. Rubio, M. Cócera, J. Estelrich, R.Pons, A. de la Maza, O. LópezEffect of dipalmitoyl-phosphatidylcholine/dihexanoyl-phosphatidylcholine (dppc/dhpc)bicelles on skin lipids molecular organization.Poster

G. Rodríguez, M. Cócera, L. Rubio, J. Cladera, N.Benseny, A. de la Maza, L. Coderch, J.L. Parra, O.LópezBicelles as preventive agents of thermaldamage in skin collagen. Poster

Skin Forum 12th Annual Meeting (28-29/03/2011; Frankfurt, Alemania) M. Cocera, G. Rodríguez, L. Rubio, L. Barbosa-Barros, F. Fauth, C. Sandt, A. de la Maza, O.LópezUse of synchrotron radiation for probing skinstructures and their function. Poster

G. Rodríguez, M. Cocera, L. Rubio, C. Barba, C.Lopez-Iglesias, A. de la Maza, O. López, Use two lipid nanostructures with coupledeffects on skin properties. Poster

134


O. López, G. Rodríguez, L. Barbosa-Barros, L.Rubio, M. Cocera, A. de la MazaBicellar nanosystems as barrier functionmodulators. Poster

22nd International Congress IFATCC (05-07/05/2010; Stresa, Italia)M. Martí, A. de la Maza, J.L. Parra and L.CoderchLiposomes as dispersing agent in dyeformulations. Poster

M. Martí, V. Martínez, L.Rubio, M. Lis, J.Valldeperas, J.L. Parra and L. CoderchBiofunctional textiles: skin effectiveness.Poster

M. Martí, J. Carilla, C. Barba, L. Coderch and A.ManichMoisture sorption/desorption of proteinfibres. Poster

A. Moure, J. Bujons, A. Messeguer, I. Alfonso.Chemical modulation of peptoids: NMRconformational studies on partiallyconstrained derivatives 5/4/2011. 1st Spanish French NMR Meeting(Sitges). Oral

I. García-Álvarez, M. Egido-Gabás, L. Romero, E.Doncel-Pérez, M. Nieto-Sampedro, J. Casas, A.Fernández-MayoralasAlterations in tumor cell metabolites bytreatment with antimitotic oleyl glycosides15/9/2010. X Jornadas de Carbohidratos. RSEQ(Granada). Oral

A. Colomer, L. Pérez, A. Pinazo, R. Infante, R.PonsLysine based surfactants: relationshipbetween chemical structure andadsorption/aggregation properties17/5/2011. Cost Action D36 Final Workshop(Fuengirola). Oral

M. Corredor, I. Alfonso, A. Messeguer.Towars a third generation of apoptosisinhibitors by structural modulations throughan amide/triazole isosteric substitution6/4/2011. 1st Spanish French NMR Meeting(Sitges). Poster

A. Moure, S.V. Luis, I. Alfonso.Jaulas pseudopeptídicas: Síntesis y estudiospreliminares de sus propiedades dereconocimiento molecular28/7/2011. XXXIII Bienal RSEQ (Valencia). Oral

M. Torrent-SucarratAnharmonicity as a possible explanation ofthe Eigen-Zundel dilemma in the IR spectrumof H+(H2O)21.8/7/2010. IX Girona Seminar: Electron Density,Density Matrices, and Density Functional Theory(Girona). Oral

A. Patti, S. Belli, R. van Roij, M. Dijkstra Relaxation dynamics in the columnar liquidcrystal phase of oblate hard spherocylinders:Effect of transient cages and permanentbarriers2-4/6/2011. XVII Congreso de Física Estadística(FisEs 2011) (Universidad de Barcelona, España).Oral

S. Leitner, G. Calderó, M. J. García-Celma, C.SolansStudies on cationic polymeric nano-emulsionsand nanoparticle dispersions for biomedicalapplications14/11/2011. IV Jornada IN2UB (Barcelona,España). Oral

S. Vílchez-Maldonado, G. Calderó, R. MolinaPolymeric nanoparticles obtained from O/Wnano-emulsions for the preparation of skin-care textiles14/11/2011. IV Jornada IN2UB (Barcelona,España). Poster

C. Fornaguera, G. Calderó, M. Llinàs, C. SolansDesign of dexamethasone loadednanoparticle dispersions as drugcarriers forinhalatory administration14/11/2011. IV Jornada IN2UB (Barcelona,España). Poster

J. Esquena, S. Vílchez, L. A. Pérez-Carrillo, C.SolansHighly porous carbonaceous materialsobtained in oil-in-alcohol highlyconcentrated emulsions30/3-21/4/2011. D43 COST workshop (Madrid,España). Oral

R. Ramsch, N. Ahmad, R. Hashim, H. A.rTajuddin, J. Esquena, C. SolansBranched glycolipids – Biomimeticamphiphilic molecules for promising drug-carriers30/3-21/4/2011. D43 COST workshop (Madrid,España). Oral

135

ORAL AND POSTER CONTRIBUTIONS (EVENTS IN SPAIN)


G. Morral, C. Solans, M. L. García, M. J. GarcíaIncorporation of ketoprofen in polyurea andpolyurethane nanoparticles obtained fromO/W nano-emulsions2-4/2/2011. EFIG 2011 (X Congreso de laSociedad Española de Farmacia Industrial yGalénica) (Madrid, España). Poster

R.M. Aparicio, A. Vílchez, J. Miras, S. Vílchez, J.Esquena, M.J. García-CelmaLiberación de fármacos in vitro a partir desistemas poliméricos macroporosos 2-4/2/2011. EFIG 2011 (X Congreso de laSociedad Española de Farmacia Industrial yGalénica) (Madrid, España). Poster

A. Vílchez, C. Rodríguez-Abreu, C. Solans, J.Esquena, A. Menner, A. BismarckMacroporous foams obtained in highlyconcentrated Pickering emulsions stabilizedsolely with magnetic nanoparticles 11-14/4/2011. NanoSpain 2011 (Bilbao, España).Poster

K. Pemartin, M. Sánchez-Domínguez, C. SolansSynthesis of inorganic nanoparticles via anovel O/W microemulsion reaction methodwith fluorescent properties and theirdispersion11-14/4/2011. NanoSpain 2011 (Bilbao, España).Poster

G. Calderó, S. Leitner, C. Bouaoud, M.J. García-Celma, C. SolansDesing of multifunctional nanocarriers forbiomedical applications11-14/4/2011. Nanobio&med (Bilbao, España).Poster

N. SanvicensNanotoxicología19/11/2010. VII Encuentro de Delegados dePrevención de Riesgos Laborales de UGT de LaRioja (Logroño).

G. Rodríguez, L. Rubio, M. Cócera, A. de laMaza, O. LópezBicellar nanostructures for dermal andpharmaceutical applications09/06/2010. IV Jornada Aplicaciones Industrialesde la Nanotecnología (Barcelona). Poster

A.M. Manich, F. Maldonado, J. Carilla, M.Catalina, A. MarsalIsotermas de sorción/desorción de humedaden el colágeno07-09/05/2010. LIX Congreso Nacional de laAsociación Química Española de la Industria delCuero (Arnedo, La Rioja). Oral

F. Maldonado, E. Bautista, A.M. Munich, A.MarsalAportación experimental sobre el fenómenode solubilización en superficie oadsolubilización de sustancias orgánicassobre figra de colágeno07-09/05/2010. LIX Congreso Nacional de laAsociación Química Española de la Industria delCuero (Arnedo, La Rioja). Oral

A.M. Manich, J. Carilla, R.A.L. Miguel, F.G.F.Franco, J.M. Lucas, D. Cayuela, J. Gacén, M. MartíAbsorción y desorción de humedad: Unacaracterística relevante de las fibras textiles24-25/03/2010. XXXVI Simposio de la AsociaciónEspañola de Químicos y Coloristas Textiles(Barcelona). Oral

D. Cayuela, A.M. ManichComportamiento y propiedades de las fibrasde polilactida (PLA) durante su producción yuso06/04/2011. XXXVII Simposio de la AsociaciónEspañola de Químicos y Coloristas Textiles(Barcelona). Oral

M.T. García, F. Comelles, L. Pérez, I. RibosaAggregation behavior and aquatic toxicity oflong chain oxygen-funtionalized ionic liquids2011. 9th Green Chemistry Conference, (Alcalade Henares, Madrid) Oral

M. Cócera, G. Rodríguez, L. Rubio, L. Barbosa-Barros, A. Labrador, C. Sandt, A. de la Maza, O.LópezSkin Visualised by Synchrotron Radiation06/09/2011. V Reunión AUSE (Valencia). Poster

F. Maldonado, J. Carilla, A. Marsal, A.M. ManichProcedure for the gravimetric determinationof the relative humidity in standard-conditioned test laboratories27-30/09/2011. XXXI IULTCS Congress(International Union of Leather Technologists andChemists Societies), (Valencia). Poster

M.E. Bautista, L. Pérez, S. Cuadros, M.T. García,A.M Manich, A. MarsalSurfactants obtained by acylation of theprotein fraction recovered from tanneryeffluent27-30/09/2011. XXXI IULTCS Congress(International Union of Leather Technologists andChemists Societies) (Valencia). Poster

A. Marsal, F. Maldonado, A.M. ManichAdsolubilization studies on collagen fibreswith 2-Naphtol as model substance27-30/09/2011. XXXI IULTCS Congress(International Union of Leather Technologists andChemists Societies) (Valencia). Poster

136


III Workshop CBN’11 (27/10/2011;Barcelona, España)A. PattiMolecular simulation of self-assemblingcolloidal systems). Oral

C. Aubéry, M. Sánchez-Domínguez, C. SolansNonionic water-in-oil and bicontinuousmicroemulsions as reaction media for thesynthesis of Mn-Zn ferrite nanoparticlesOral

S. Leitner, G. Calderó, M.J. García-Celma, C.SolansStudies on cationic polymeric nano-emulsionsand nanoparticle dispersions for biomedicalapplications. Poster

M. Llinàs, G. Calderó, M.J. García-Celma, A. Patti,C. SolansControlled drug release by pH from W/Ohighly concentrated emulsions. Poster

N. Vilanova, C. Rodríguez-Abreu, C. SolansLoaded porous silicone microparticles bymultiple emulsion templating. Poster

A. Vílchez, A, Menner, A. Bismarck, C. Rodríguez-Abreu, J. EsquenaTailoring pore morphology, permeability andmechanical properties of magneticmacroporous polymers foams. Oral

Solé, S. Vílchez, R. Molina, N. Montanyà, R.Aparicio, M.J. García-Celma, J.Esquena Textiles modified with chitosan hydrogels formedical andor therapeutical applications.Oral

J. Miras, S. Vílchez, C. Solans, J. EsquenaPreparation and characterization of highlyconcentrated emulsions in presence ofchitosan. Poster

M. Martínez, C. Solans, F. Valor, J. López, E.Tomás, J. EsquenaPreparation and characterization of highlyconcentrated bitumen emulsions with smalldroplet size. Poster

S. Vílchez-Maldonado, G. Calderó, R. Molina, N.Azemar, C. SolansPreparation and incorporation of functionalnanoparticles on cotton textile. Poster

41 Jornadas Anuales del CED (6-7/04/2011;Barcelona, España)R. Ramsch, N. Ahmad, R. Hashim, H.A. Tajuddin,J. Esquena, C. SolansNatural-like synthetic glycolipids exhibiting arich phase behavior. Poster

M. Martínez, J. Vilasau, C. Solans, F. Valor, J.López, E. Tomás, J. Esquena Preparacion and characterization of highlyconcentrate bitumen emulsion withcontrolled droplet sizePoster

M. Homs, M. Llinàs, C. SolansCharacterization of a polyglyceryl-derivednonionic surfactant and formation of highlyconcentrated emulsions. Poster

Manroshan, S., J. Esquena, C. Solans, B. Levecke,K. Booten, Th.F. TadrosStability of vulcanized natural rubber latexby a hydrophobically modified polyfructosesurfactant. Poster

S. Leitner, G. Calderó, M. J. García-Celma, C.SolansPreparation and characterization of polymer-in-water (P/W) cationic nano-emulsions andtheir use for nanoparticle preparation. Poster

K. Pemartin, C. Aubery, M. Sanchez-Dominguez,C. SolansSynthesis of superparamagnetic mixed oxidenanoparticles in the novel oil-in-watermicroemulsion reaction method. Poster

M.T. García, A. Cornellas, I. Ribosa, F. Comelles,MªA. Manresa, L. PérezSurfactant-like behavior and antimicrobialactivity of long-chain ionic liquids in aqueoussolution. Oral

C. Barba, M. Martí, A. Manich, J. L. Parra and L.Coderch Effectiveness of wool keratin proteins andpeptides on hair. Poster

E. Fernández, C. Barba, C. Alonso, M. Martí, J.L.Parra and L. CoderchPhotodegradation determination of humanhair. Poster

5th Annual Conference CIBER-BBN 2011(12-13/07/2011; Zaragoza, España)S. Leitner, G. Calderó, M.J. García-Celma, C.Solans Cationic polymeric nanoparticles preparedfrom nano-emulsions, suitable for genetherapy. Oral poster

C. Fornaguera, G. Calderó, M. Llinàs, C. SolansDesign of nanoparticle dispersions forinhalatory administration. Oral poster

G. Calderó, M.J. García-Celma, C. SolansAdvanced polymeric nanoparticles fromnano-emulsions. Oral poster

C. Solans, J. Esquena, M.J. García-CelmaNanocarriers for antiapoptotic drug transportacross the blood-brain-barrier (Nano-Trans-Brain). Poster

137


SETMANA DE LA CIÈNCIA 2010 (12/11/2010 a 22/11/2010) Conferències DivulgativesG. Valencia,Només afegiu aigua

J. CasasSuïcidi cel·lular: rituals per a la supervivència

J. L. TorresDarwin avui

R. PonsSabons i bombolles

A. MesseguerHi haurà química entre nosaltres?

R. EritjaADN i ordinadors

SETMANA DE LA CIÈNCIA 2011 (10/11/2011 a 24/11/2011) Conferències DivulgativesG. Valencia,Foc i flames

F. J. Sánchez Baeza Sensores para la detección de biomarcadoresde enfermedades neurológicas yneurodegenerativas. Aplicaciones para eldiagnóstico clínico de estas patologías”.

R. EritjaADN i ordinadors

A. MesseguerHi haurà química entre nosaltres?

J. CasasSuïcidi cel·lular: rituals per a la supervivència

G. Fabriàs Fàrmacs: química que cura

I. AlfonsoDe la materia inanimada a la vida:autoorganización y evolución molecular

OTHER EVENTSEL CSIC EN EL AULA (COLABORACION CON INSTITUCIONES EDUCATIVAS).

A. MesseguerHi haurà química entre nosaltres?Esparraguera. 22/04/2010

R. Eritja ADN i ordinadorsEsplugues del Llobregat. 04/03/2010

J. CasasSuïcidi cel.lularBarcelona. 23/02/2010

R. Eritja ADN i ordinadorsBarcelona. 08/02/2010

J.L. Torres Radicals lliures: envelliment saludable Mollerussa (Lleida). 04/02/2010

J.L. TorresRadicals lliures: envelliment saludableBarcelona. 02/02/2010

Química i atracció sexual en insectesConferència del Dr. Angel Guerrero (amb motiude l’Any Internacional de la Química)Museu de la Ciència i de la Tècnica de Catalunya(Terrassa)11/10/2011

Utilització de feromones d’insectes en uncontrol integrat de plagues Conferència del Dr. Ángel Guerrero (amb motiude l’Any Internacional de la Química)Museu de Mataró (Secció de Ciències Naturals).10/5/2011

Presentación del Centro Química Coloidal eInterfacialC. Solans; C. Rodríguez-Abreu; J. Esquena; G. Calderó JORNADA CIENTÍFICA. 16/06/2010

138


Publications in ISI journals (journals in alphabetical order) 140Publications in non-ISI journals (journals in alphabetical order) 151Book Chapters 152

Highlighted:

Scopus errors

Conference papers, Editorial, Erratum

8.2. APPENDIX 2. SCIENTIFIC OUTPUT

LIBRO IQAC. Appendix2.pags 139-152.qxd:Maquetación 1 11/6/12 10:35 Página 139

Characterization of perylene diimide dye self-assembliesand their use as templates for the synthesis of hybridand supermicroporous nanotubulesRodríguez Abreu, C.; Aubery, C.; Solans, C.; López-Quintela,M. A.; Tiddy, G.ACS Appl. Mater. Interfaces 3 4133–4141, 2011

Improved properties of oxygen and argon RF plasma-activated polyester fabrics loaded with TiO2nanoparticlesMihailovic, D., Saponjic, Z., Molina, R., Puac, N., Jovancic, P.,Nedeljkovic, J., Radetic, M.ACS Appl. Mater. Interfaces 2 1700-1706, 2010

The myo-1,2-diaminocyclitol scaffold defines potentglucocerebrosidase activators and promisingpharmacological chaperones for Gaucher diseaseTrapero, A., Llebaria, A.ACS Med. Chem. Lett. 2 614–619, 2011

Electronic anabolic steroid recognition with carbonnanotube field-effect transistorsMartínez, M.T., Tseng, Y.-C., Salvador, J.P., Marco, M.P.,Ormategui, N., Loinaz, I., Bokor, J.ACS Nano 4 1473-1480, 2010

The role of counterions in the membrane-disruptiveproperties of pH-sensitive lysine-based surfactantsNogueira, D.R., Mitjans, M., Infante, M.R., Vinardell, M.P.Acta Biomater. 7 2846-2856, 2011

Current trends in asymmetric synthesis with aldolasesClapés, P., Garrabou, X.Adv. Synth. Catal. 353 2263-2283, 2011

Enzymatic synthesis of α-glucosides of resveratrol withsurfactant activityTorres, P., Poveda, A., Jimenez-Barbero, J., Parra, J.L.,Comelles, F., Ballesteros, A.O., Plou, F.J.Adv. Synth. Catal. 353 1077-1086, 2011

Redesign of the phosphate binding site of L-rhamnulose-1-phosphate aldolase towards a dihydroxyacetonedependent aldolaseGarrabou, X., Joglar, J., Parella, T., Crehuet, R., Bujons, J.,Clapés, P.Adv. Synth. Catal. 353 89-99, 2011

A mutant D-fructose-6-phosphate aldolase (Ala129Ser)with improved affinity towards dihydroxyacetone forthe synthesis of polyhydroxylated compoundsCastillo, J.A., Guérard-Hélaine, C., Gutiérrez, M., Garrabou,X., Sancelme, M., Schürmann, M., Inoue, T., Hélaine, V.,Charmantray, F., Gefflaut, T., Hecquet, L., Joglar, J., Clapés, P.,Sprenger, G.A., Lemaire, M.Adv. Synth. Catal. 352 1039-1046, 2010

Diacyl glycerol arginine-based surfactants: biological andphysicochemical properties of catanionic formulations.Lozano, N., Pons, R., Pérez, L., Pinazo, A.Amino Acids 40 721-729, 2011

Drug discovery targeted at transthyretin cardiacamyloidosis: Rational design, synthesis, and biologicalactivity of new transthyretin amyloid inhibitorsBlasi, D., Pinto, M., Nieto, J., Arsequell, G., Valencia, G.,Planas, A., Centeno, N.B., Quintana, J.Amyloid 18 (SUPPL. 1) 55-57, 2011

Ligand-binding properties of human transthyretinPinto, M., Blasi, D., Nieto, J., Arsequell, G., Valencia, G.,Planas, A., Quintana, J., Centeno, N.B.Amyloid 18 (SUPPL. 1) 51-54, 2011

Quantum dot-based array for sensitive detection ofEscherichia coliSanvicens, N., Pascual, N., Fernández-Argüelles, M.T., Adrián,J., Costa-Fernández, J.M., Sánchez-Baeza, F., Sanz-Medel, A.,Marco, M.P.Anal. Bioanal. Chem. 399 2755-2762, 2011

Chemical equilibria studies using multivariate analysismethods.Jaumot, J., Eritja, R., Gargallo, R.Anal. Bioanal. Chem. 399 1983-1997, 2011

Recent advances in analytical and bioanalysisapplications of noble metal nanorodsMannelli, I., Marco, M.P.Anal. Bioanal. Chem. 398 2451-2469, 2010Erratum: Anal. Bioanal. Chem. 399 1923, 2011

A fluorescent polarization-based assay for theidentification of disruptors of the RCAN1-calcineurin Aprotein complexCarme Mulero, M., Orzáez, M., Messeguer, J., Messeguer, A.,Pérez-Payá, E., Pérez-Riba, M.Anal. Biochem. 398 99-103, 2010

Assessment of synthetic chimeric multiple antigenicpeptides for diagnosis of GB virus C infectionGómara, M.J., Fernández, L., Pérez, T., Ercilla, G., Haro, I.Anal. Biochem. 396 51-58, 2010

Gel-based immunotest for simultaneous detection of2,4,6-trichlorophenol and ochratoxin A in red wineBeloglazova, N.V., Goryacheva, I.Y., Rusanova, T.Y., Yurasov,N.A., Galve, R., Marco, M.P., De Saeger, S.Anal. Chim. Acta 672 3-8, 2010

Preliminary study for simultaneous detection andquantification of androgenic anabolic steroids usingELISA and pattern recognition techniquesCalvo, D., Tort, N., Pablo Salvador, J., Marco, M.P., Centi, F.,Marco, S.Analyst 136 4045-4052, 2011

O2 activation and selective phenolate orthohydroxylation by an unsymmetric dicopper μη1: η1-peroxido complexGarcia-Bosch, I., Company, A., Frisch, J.R., Torrent-Sucarrat,M., Cardellach, M., Gamba, I., Güell, M., Casella, L., Que Jr.,L., Luis, J.M., Costas, M.Angew. Chem. Int. Edit. 49 2406-2409, 2010

A liquid-crystalline single-molecule magnet with variablemagnetic propertiesGonidec, M., Luis, F., Vilchez, À., Esquena, J., Amabilino,D.B., Veciana, J.Angew. Chem. Int. Edit. 49 1623-1626, 2010

Regulation of autophagy by sphingolipidsBedia, C., Levade, T., Codogno, P.Anti-Cancer Agents Med. Chem. 11 844-853, 2011

Ceramidases in hematological malignancies: Senseless orneglected target?Fabriàs, G., Bedia, C., Casas, J., Abad, J.L., Delgado, A.Anti-Cancer Agents Med. Chem. 11 830-843, 2011

Inhibition of the corrosion of iron in acidic solution bythe oligomeric surfactant N, N, N′, N″, N″-pentamethyldiethyleneamine-N, N″-di-[tetradecylammoniumbromide]Bensajjay, F., Alehyen, S., Achouri, M.E., Hajjaji, N.,Bellaouchou, A., Pérez, L., Infante, M.R.Anti-Corros. Methods Mater. 58 258-266, 2011

Interaction of arginine-based cationic surfactants withlipid membranes. An experimental and molecularsimulation studyAlmeida, J.A.S., Morán, M.C., Infante, M.R., Pais, A.A.C.C.Arkivoc (part v) 34-50, 2010Almeidaa, J.A.S., Morána, M.C., Infanteb, M.R., Paisa,A.A.C.C.

Immobilization of PLP-dependent enzymes with cofactorretention and enhanced stabilityLópez, C., Ríos, S.D., López-Santín, J., Caminal, G., Álvaro G.Biochem. Eng. J. 49 414-421, 2010

PUBLICATIONS (papers in ISI journals)

140


Effect of E1(64-81) hepatitis G peptide on the in vitrointeraction of HIV-1 fusion peptide with membranemodelsSánchez-Martín, M.J., Busquets, M.A., Girona, V., Haro, I.,Alsina, M.A., Pujol, M.Biochim. Biophys. Acta-Biomembranes 1808 2178-2188,2011

Study of the inhibition capacity of an 18-mer peptidedomain of GBV-C virus on gp41-FP HIV-1 activityHaro, I., Gómara, M.J., Galatola, R., Domènech, O., Prat, J.,Girona, V., Busquets, M.A.Biochim. Biophys. Acta-Biomembranes 1808 1567-1573,2011

Acridine and quindoline oligomers linked through a 4-aminoproline backbone prefer G-quadruplexstructures.Ferreira, R., Artali, R., Farrera-Sinfreu, J., Albericio, F., Royo,M., Eritja, R., Mazzini, S.Biochim. Biophys. Acta-Gen. Subj. 1810 769-776, 2011

Synthesis and properties of oligonucleotides carryingisoquinoline imidazo[1,2-a]azine fluorescent units.Pérez-Rentero, S., Kielland, N., Terrazas, M., Lavilla, R., Eritja,R.Bioconjugate Chem. 21 1622-1628, 2010

Synthesis, cell-surface binding, and cellular uptake offluorescently labeled glucose-DNA conjugates withdifferent carbohydrate presentation.Ugarte-Uriba, B., Pérez-Rentero, S., Lucas, R., Aviñó, A.,Reina, J.J., Alkorta, I., Eritja, R., Morales, J.C.Bioconjugate Chem. 21 1280-1287, 2010

Pheromone synthesis in a biomicroreactor coated withanti-adsorption polyelectrolyte multilayerDimov, N., Muñoz, L., Carot-Sans, G., Verhoeven, M.L.P.M.,Bula, W.P., Kocer, G., Guerrero, A., Gardeniers, H.J.G.E.Biomicrofluidics 5 034102, 2011 (12 pages)http://dx.doi.org/10.1063/1.3608138

2-Aminohydroxamic acid derivatives as inhibitors ofBacillus cereus phosphatidylcholine preferredphospholipase C PC-PLC(Bc).Gonzalez-Bulnes, P., Gonzalez-Roura, A., Canals, D., Delgado,A., Casas, J., Llebaria, A.Bioorg. Med. Chem. 18 8549-8555, 2010

Synthesis and structural properties of oligonucleotidescovalently linked to acridine and quindoline derivativesthrough a threoninol linker.Aviñó, A., Mazzini, S., Ferreira, R., Eritja, R.Bioorg. Med. Chem. 18 7348-7356, 2010

Stepwise synthesis of oligonucleotide-peptideconjugates containing guanidinium and lipophilicgroups in their 3′-terminiGrijalvo, S., Terrazas, M., Aviñó, A., Eritja, R.Bioorg. Med. Chem. Lett, 20 2144-2147, 2010

Crowding induces differences in the diffusion ofthermophilic and mesophilic proteins: A new look atneutron scattering results.Marcos, E., Mestres, P., Crehuet, R.Biophys. J. 101 2782-2789, 2011

Bicosomes: Bicelles in dilute systemsRodríguez, G., Soria, G., Coll, E., Rubio, L., Barbosa-Barros, L.,López-lglesias, C., Planas, A.M., Estelrich, J., de La Maza, A.,López, O.Biophys. J. 99 480-488, 2010

Carbon nanotube composite peptide-based biosensorsas putative diagnostic tools for rheumatoid arthritisde Gracia Villa, M., Jiménez-Jorquera, C., Haro, I., Gomara,M.J., Sanmartí, R., Fernández-Sánchez, C., Mendoza, E.Biosens. Bioelectron. 27 113-118, 2011

Competitive multi-immunosensing of pesticides basedon the particle manipulation with negativedielectrophoresisRamón-Azcón, J., Yasukawa, T., Lee, H.J., Matsue, T.,Sánchez-Baeza, F., Marco, M.P., Mizutani, F.Biosens. Bioelectron. 25 1928-1933, 2010

A label-free and portable multichannel surface plasmonresonance immunosensor for on site analysis ofantibiotics in milk samplesFernández, F., Hegnerová, K., Piliarik, M., Sanchez-Baeza, F.,Homola, J., Marco, M.P.Biosens. Bioelectron. 26 1231-1238, 2010

(E)-Pityol as aggregation pheromone of Pityophthoruspubescens (Marsham) (Coleoptera: Scolytinae): Biologicalactivity in the laboratory and in the fieldLópez, S., Quero, C., Iturrondobeitia, J.C., Guerrero, A.,Goldarazena, A.Can. Entomol. 143 447-454, 2011

Hydrophobically modified inulin from alkenyl succinicanhydride in aqueous mediaMorros, J., Levecke, B., Infante, M.R.Carbohydr. Polym. 84 1110-1116, 2011

Synthesis of β-hydroxyalkyl ethers of inulin in aqueoussurfactant mediaMorros, J., Levecke, B., Infante, M.R.Carbohydr. Polym. 82 1168-1173, 2010

Chemical hydrophobic modification of inulin in aqueousmedia: Synthesis of β-hydroxyalkyl ethers of inulinMorros, J., Levecke, B., Infante, M.R.Carbohydr. Polym. 81 681-686, 2010

Synthesis of CeO2, ZrO2, Ce0.5Zr0.5O2, and TiO2nanoparticles by a novel oil-in-water microemulsionreaction method and their use as catalyst support for COoxidationSánchez-Domínguez, M., Liotta, L.F., Di Carlo, G., Pantaleo,G., Venecia, A.M., Solans, C., Boutonnet, M.Catal. Today 158, 35-46, 2010

Effect of North bicyclo[3.1.0]hexane 2'-deoxy-pseudosugars on RNA interference: A novel class ofsiRNA modificationTerrazas, M., Ocampo, S.M., Perales, J.C., Marquez, V.E.,Eritja, R.ChemBioChem 12 1056-1065, 2011

Redesigning the active site of transaldolase TalB fromescherichia coli: New variants with improved affinitytowards nonphosphorylated substratesSchneider, S., Gutiérrez, M., Sandalova, T., Schneider, G.,Clapés, P., Sprenger, G.A., Samland, A.K.ChemBioChem 11 681-690, 2010

Synthesis of lipid-oligonucleotide conjugates for RNAinterference studies.Grijalvo, S., Ocampo, S.M., Perales, J.C., Eritja, R.Chem. Biodivers. 8 287-299, 2011

Triplex-stabilizing properties of parallel clamps carryingLNA derivatives at the Hoogsteen strandAlvira, M., Eritja, R.Chem. Biodivers. 7 376–382, 2010

Dihydrosphingomyelin impairs HIV-1 infection byrigidifying liquid-ordered membrane domainsVieira, C.R., Munoz-Olaya, J.M., Sot, J., Jiménez-Baranda, S.,Izquierdo-Useros, N., Abad, J.L., Apellániz, B., Delgado, R.,Martinez-Picado, J., Alonso, A., Casas, J., Nieva, J.L., Fabriás,G., Mañes, S., Goñi, F.M.Chem. Biol. 17 766-775, 2010

Diagnostic value of anti-GBV-C antibodies in HIV-infected patientsGómara, M.J., Fernández, L., Pérez, T., Tenckhoff, S.,Casanovas, A., Tillmann, H.L., Haro, I.Chem. Biol. Drug Des. 78 277-282, 2011

141


Potential implication of aniline derivatives in the ToxicOil Syndrome (TOS)Messeguer, A.Chem-Biol. Interact. 192 136-141, 2011 (Proceedings of the8th International Symposium on Biological ReactiveIntermediates. Conference Paper)

Proteomics of toxic oil syndrome in humans: Phenotypedistribution in a population of patientsQuero, C., Colomé, N., Rodríguez, C., Eichhorn, P., Posada DeLa Paz, M., Gelpi, E., Abian, J.Chem-Biol. Interact. 192 129-135, 2011 (Proceedings of the8th International Symposium on Biological ReactiveIntermediates. Conference Paper)

Enantiopure triazolium salts: Chemoenzymatic synthesisand applications in organocatalysisRíos-Lombardía, N., Porcar, R., Busto, E., Alfonso, I., Montejo-Bernardo, J., García-Granda, S., Gotor, V., Luis, S.V., García-Verdugo, E., Gotor-Fernández, V.ChemCatChem 3 1921-1928, 2011

Structure-guided redesign of D-fructose-6-phosphatealdolase from E. coli: Remarkable activity and selectivitytowards acceptor substrates by two-point mutationGutierrez, M., Parella, T., Joglar, J., Bujons, J., Clapés, P.Chem. Commun. 47 5762-5764, 2011

Formation of vesicles with an organometallic lipidbilayer by supramolecular arrangement of metalcarbonyl metallosurfactantParera, E., Comelles, F., Barnadas, R., Suades, J.Chem. Commun. 47 4460-4462, 2011

Structurally disfavoured pseudopeptidic macrocyclesthrough anion templationBru, M., Alfonso, I., Bolte, M., Burguete, M.I., Luis, S.V.Chem. Commun. 47 283-285, 2011

Stable radical cores: A key for bipolar charge transportin glass forming carbazole and indole derivatives.Castellanos, S., Gaidelis, V., Jankauskas, V., Grazulevicius, J.V.,Brillas, E., López-Calahorra, F., Juliá, L., Velasco, D.Chem. Commun. 46 5130-5132, 2010

Modified siRNAs for the study of the PAZ domainSomoza, A., Terrazas, M., Eritja, R.Chem. Commun. 46 4270-4272, 2010

Chemical modulation of peptoids: synthesis andconformational studies on partially constrainedderivativesMoure, A., Sanclimens, G., Bujons, J., Masip, I., Alvarez-Larena, A., Pérez-Payá, E., Alfonso, I., Messeguer, A.Chem. Eur. J. 17 7927-7939, 2011

Protonation of water clusters induced by thehydroperoxyl radical surfaceTorrent-Sucarrat, M., Ruiz-López, M.F., Martins-Costa, M.,Francisco, J.S., Anglada, J.M.Chem.-Eur. J. 17 5076-5085, 2011

Structure-guided minimalist redesign of L-fuculose-1-phosphate aldolase active site. Expedient synthesis ofnovel polyhydroxylated pyrrolizidines and theirinhibitory properties against glycosidases and intestinaldisaccharidases.Garrabou, X.; Gomez, L.; Joglar, J.; Gil, S.; Parella, T.; Bujons,J.; Clapés, P.Chem.-Eur. J. 16, 10691-10706, 2010

The bipyridyl derivatives as photomemory devices. Acomparative electronic-structure study.Ortiz-Sáhez, J.M., Gelabert, R., Moreno, M., Lluch J.,Anglada, J.M., Bofill J.M.Chem.-Eur. J. 16 6693-6703, 2010

Structural diversity in the self-assembly ofpseudopeptidic macrocyclesAlfonso, I., Bru, M., Isabel Burguete, M., García-Verdugo, E.,Luis, S.V.Chem.-Eur. J. 16 1246-1255, 2010

From salts to ionic liquids by systematic structuralmodifications: A rational approach towards the efficientmodular synthesis of enantiopure imidazolium saltsRíos-Lombardía, N., Busto, E., Gotor-Fernández, V., Gotor, V.,Porcar, R., García-Verdugo, E., Luis, S.V., Alfonso, I., Garcia-Granda, S., Menéndez-Velázquez, A.Chem.-Eur. J. 16 836-847, 2010

Development of stable, water dispersible andbiofunctionalizable superparamagnetic iron oxidenanoparticlesMiguel, N., Bomatí-Miguel, O., Colom, G., Salvador, J.,Marco, M.P., Santamaría, J.Chem. Mat. 23 2795-2802, 2011

Integrated synthetic, pharmacological, andcomputational investigation of cis-2-(3,5-dichlorophenylcarbamoyl) cyclohexanecarboxylic acidenantiomers as positive allosteric modulators ofmetabotropic glutamate receptor subtype 4.Christov, C., González-Bulnes, P., Malhaire, F., Karabencheva,T., Goudet, C., Pin, J.P., Llebaria, A., Giraldo, J.ChemMedChem. 6 131-140, 2011

Synthesis of fatty acid amides of catechol metabolitesthat exhibit antiobesity propertiesAlmeida, B., Joglar, J., Luque Rojas, M.J., Decara, J.M.,Bermúdez-Silva, F.J., Macias-González, M., Fitó, M., Romero-Cuevas, M., Farré, M., Covas, M.I., Rodríguez De Fonseca, F.,De La Torre, R.ChemMedChem 5 1781-1787, 2010

Identification of new ozonation disinfection byproductsof 17β-estradiol and estrone in waterPereira, R.D.O., de Alda, M.L., Joglar, J., Daniel, L.A., Barceló,D.Chemosphere 84 1535-1541, 2011

White-rot fungus-mediated degradation of theanalgesic ketoprofen and identification of intermediatesby HPLC-DAD-MS and NMRMarco-Urrea, E., Pérez-Trujillo, M., Cruz-Morató, C., Caminal,G., Vicent, T.Chemosphere 78 474-481, 2010

Biophysical investigations of GBV-C E1 peptides aspotential inhibitors of HIV-1 fusion peptideSánchez-Martín, M.J., Urbán, P., Pujol, M., Haro, I., Alsina,M.A., Busquets, M.A.ChemPhysChem 12 2816-2822, 2011

Differential behavior of amino-imino constitutionalisomers in nonlinear optical processes.Latorre, S., de Moreira, I.P.R., Villacampa, B., Julià, L., Velasco,D., Bofill, J.M., López-Calahorra, F.ChemPhysChem. 11 912-919, 2010

Update 1 of: Enantioselective enzymaticdesymmetrizations in organic synthesisGarcía-Urdiales, E., Alfonso, I., Gotor, V.Chem. Rev. 111 PR110-PR180, 2011

Solution behavior of aqueous mixtures of low and highmolecular weight hydrophobic amphiphilesRodríguez-Abreu, C., Sánchez-Domínguez, M., Šarac, B.,Bešter Roga , M., Shrestha, R.G., Shrestha, L.K., Varade, D.,Ghosh, G., Aswal, V.K.Colloid Polym. Sci. 288 923-935, 2010. Erratum to 288 739-751:

Influence of a mixed ionic/nonionic surfactant systemand the emulsification process on the properties ofparaffin emulsionsVilasau, J., Solans, C., Gómez, M.J., Dabrio, J., Mújika-Garai,R., Esquena, J.Colloid Surf. A-Physicochem. Eng. Asp. 392, 38-44, 2011

Stability of oil-in-water paraffin emulsions prepared in amixed ionic/nonionic surfactant system Vilasau, J., Solans, C., Gómez, M.J., Dabrio, J., Mújika-Garai,R., Esquena, J.Colloid Surf. A-Physicochem. Eng. Asp. 389 222-229, 2011

142


Phase behaviour of a mixed ionic/nonionic surfactantsystem used to prepare stable oil-in-water paraffinemulsions Vilasau, J., Solans, C., Gómez, M.J., Dabrio, J., Mújika-Garai,R., Esquena, J.Colloid Surf. A-Physicochem. Eng. Asp. 384 473-481, 2011

Nonaqueous foam with outstanding stability indiglycerol monomyristate/olive oil system Shrestha, R.G., Shrestha, L.K., Solans, C., Gonzalez, C.,Aramaki, K. Colloid Surf. A-Physicochem. Eng. Asp. 353 157-165, 2010

Bicellar systems as modifiers of skin lipid structure Rodríguez, G., Barbosa-Barros, L., Rubio, L., Cócera, M.,López-Iglesias, C., de la Maza, A., López, O. Colloid Surf. B-Biointerfaces 84 390-394, 2011

The gas phase reaction of carbonyl oxide with hydroxylradical in presence of water vapor. A theoretical studyon the reaction mechanism Mansergas, A., González, J., Ruiz-López, M., Anglada, J.M. Comput. Theor. Chem. 965 313-320, 2011

Foreword Anglada, J.M., Ruiz-López, M.F.Comput. Theor. Chem. 965 247, 2011. Document Type:Editorial

Arginine diacyl-glycerolipid conjugates asmultifunctional biocompatible surfactants Pinazo, A., Lozano, N., Pérez, L., Morán, M.C., Infante, M.R.,Pons, R. C. R. Chim. 14 726-735, 2011

Medicinal chemistry of aminocyclitols Díaz, L., Delgado, A.Curr. Med. Chem. 17 2393-2418, 2010

Recent progress in stereoselective synthesis withaldolases Clapés, P., Fessner, W.-D., Sprenger, G.A., Samland, A.K. Curr. Opin. Chem. Biol. 14 154-167, 2010

Chiral molecular receptors based on trans-cyclohexane-1,2-diamine Alfonso, I. Curr. Org. Synth. 7 1-23, 2010

Absorption and metabolization of cytoprotectiveepicatechin thio conjugates in rats. Selga, A., Vinardell, M.P., Martín-Venegas, R., Jáuregui, O.,Casas, J., Torres, J.L.Drug Metab. Dispos. 38 2188-2194, 2010

Antioxidant activities of hydroxytyrosol mainmetabolites do not contribute to beneficial healtheffects after olive oil ingestion Khymenets, O., Fitó, M., Touriño, S., Muñoz-Aguayo, D.,Pujadas, M., Torres, J.L., Joglar, J., Farré, M., Covas, M.-I., DeLa Torre, R. Drug Metab. Dispos. 38 1417-1421, 2010

Biocompatible surfactants from renewable hydrophiles Infante, M.R., Pérez, L., Morán, M.C., Pons, R., Mitjans, M.,Vinardell, M.P., Garcia, M.T., Pinazo, A. Eur. J. Lipid Sci. Technol. 112 110-121, 2010

Antibodies against β-fibrin synthetic peptides: A studyof their association with the immunogeneticbackground and disease course of rheumatoid arthritispatients Haro, I., Gómara, M.J., Pérez, M.L., Viñas, O., Ercilla, G.,Gómez-Puerta, J.A., Sanmartí, R. Eur. J. Med. Chem. 46 1095-1102, 2011

A novel free radical scavenger rescues retinal cells invivo.O’Driscoll, C., Doonan, F., Sanvicens, N., Messeguer, A., Cott,T.G.Exp. Eye Res. 93 65-74, 2011

Restoring important hair properties with wool keratinproteins and peptidesBarba, C., Scott, S., Roddick-Lanzilotta, A., Kelly, R., Manich,A.M., Parra, J.L., Coderch, L. Fiber. Polym. 11 1055-1061, 2010

Influence of chitosan on the effects of proteases onwool fibers Vílchez, S., Jovan i , P., Erra. P.Fiber. Polym. 11 28-35, 2010

Direct analysis of glucuronidated metabolites of mainolive oil phenols in human urine after dietaryconsumption of virgin olive oil Khymenets, O., Farré, M., Pujadas, M., Ortiz, E., Joglar, J.,Covas, M.I., De La Torre, R. Food Chem. 126 306-314, 2011

Determination of atrazine residues in red wine samples.A conductimetric solutionValera, E., Ramón-Azcón, J., Barranco, A., Alfaro, B., Sánchez-Baeza, F., Marco, M.P., Rodríguez, A. Food Chem. 122 888-894, 2010

Matrix effects on the bioavailability of resveratrol inhumans.Ortuño, J., Covas, M.-I., Farre, M., Pujadas, M., Fito, M.,Khymenets, O., Andrés Lacueva, C., Roset, P., Joglar, J.,Lamuela Raventós, R., de la Torre, R.Food Chem. 120 1123-1130, 2010

Low-frequency sounds induce acoustic trauma incephalopods André, M., Solé, M., Lenoir, M., Durfort, M., Quero, C., Mas,A., Lombarte, A., Van Der Schaar, M., López-Bejar, M., Morell,M., Zaugg, S., Houégnigan, L. Front. Ecol. Environ. 9 489-493, 2011

Cytotoxicity and enzymatic activity inhibition in cell linestreated with novel iminosugar derivatives.Padró, M., Castillo, J.A., Gómez, l., Joglar, J., Clapés, P., deBolós, C.Glycoconj. J. 27 277-285, 2010

Magnetically separable nanocomposites withphotocatalytic activity under visible light for theselective transformation of biomass-derived platformmoleculesBalu, A., Cot, J., Baruwati, B., Serrano, E., García-Martínez, J.,Barma, S., Luque, R.Green Chem. 13 2750-2758, 2011

Further studies on the biodegradation of ionic liquidsFord, L., Harjani, J.R., Atefi, F., Garcia, M.T., Singer, R.D.,Scammells, P.J.Green Chem. 12 1783-1789, 2010

Sonogashira coupling reactions in biodegradable ionicliquids derived from nicotinic acidHarjani, J.R., Abraham, T.J., Gomez, A.T., Garcia, M.T., Singer,R.D., Scammells, P.J.Green Chem. 12 650-655, 2010

Amino acids as raw material for biocompatiblesurfactants Pinazo, A., Pons, R., Pérez, L., Infante, M.R. Ind. Eng. Chem. Res. 50 4805-4817, 2011

Juvenile hormone and allatostatins in the Germancockroach embryoMaestro, J.L., Pascual, N., Treiblmayr, K., Lozano, J., Bellés, X.Insect Biochem. Mol. Biol. 40 660-665, 2010

A diversity of putative carboxylesterases are expressed inthe antennae of the noctuid moth Spodoptera littoralisDurand, N., Carot-Sans, G., Chertemps, T., Montagné, N.,Jacquin-Joly, E., Debernard, S., Maïbèche-Coisne, M.Insect Mol. Biol. 19 87-97, 2010

Influence of pH, temperature and the cationic porphyrinTMPyP4 on the stability of the i-motif formed by the 5’-(C3TA2)4-3’ sequence of the human telomere. Fernández, S., Eritja, R., Aviñó, A., Jaumot, J. Gargallo, R.Int. J. Biol. Macromol. 49 729-736, 2011

143


144

Barrier function of intact and impaired skin:Percutaneous penetration of caffeine and salicylic acid Rubio, L., Alonso, C., López, O., Rodríguez, G., Coderch, L.,Notario, J., de la Maza, A., Parra, J.L. Int. J. Dermatol. 50 881-889, 2011

Compatibility of plastic with phase change materials(PCM)Castellón, C., Martorell, I., Cabeza, L.F., Fernández, A.I.,Manich, A.M.Int. J. Energy Res. 35 765-771, 2011

Use of oligonucleotides carrying photolabile groups forthe control of the deposition of nanoparticles insurfaces and nanoparticle association. Manning, B., Eritja, R. Int. J. Mol. Sci. 12 7238-7249, 2011

Functionalization and self-assembly of DNAbidimensional arrays. Garibotti, A.V., Pérez-Rentero, S., Eritja, R.Int. J. Mol. Sci. 12 5641-5651, 2011

Comparative sensitivity of tumor and non-tumor celllines as a reliable approach for in vitro cytotoxicityscreening of lysine-based surfactants with potentialpharmaceutical applicationsNogueira, D.R., Mitjans, M., Infante, M.R., Vinardell, M.P. Int. J. Pharm. 420 51-58, 2011

Bicellar systems for in vitro percutaneous absorption ofdiclofenac .Rubio, L., Alonso, C., Rodríguez, G., Barbosa-Barros, L.,Coderch, L., de la Maza, A., Parra, J.L., López, O.Int. J. Pharm. 386 108-113, 2010

Structure, stability and dynamics of hydrogenpolyoxides.Martins-Costa, M., Anglada, J.M., Ruiz-López, M.F. Int. J. Quantum Chem. 111 1543-1554, 2011

Water effects on atmospheric reactions. Buszek, R.J., Francisco, J.S., Anglada. J.M.Int. Rev. Phys. Chem. 30 335–369, 2011

Interfacial processes in textile materials: Relevance toadhesion Molina, R., Esquena, J., Erra, P. J. Adhes. Sci. Technol. 24 7-33, 2010

Analysis of nonextractable phenolic compounds infoods: the current state of the artPérez-Jiménez, J., Torres, J.L.J. Agric. Food Chem. 59 12713-12724, 2011

Metabolites in contact with the rat digestive tract afteringestion of a phenolic-rich dietary fiber matrix. Touriño, S., Pérez-Jiménez, J., Mateos-Martín, M.L., Fuguet,E., Vinardell, M.P., Cascante, M., Torres, J.L. J. Agric. Food Chem. 59 5955–5963, 2011

Galloylated polyphenols as inhibitors of hemoglobin-catalyzed lipid oxidation in fish muscleIglesias Neira, J., Pazos, M., Maestre, R., Torres, J.L., Medina, I.J. Agric. Food Chem. 59 5684-5691, 2011

Portable surface plasmon resonance immunosensor fordetection of fluoroquinolone antibiotic residues in milkFernandez, F., Pinacho, D.G., Sánchez-Baeza, F., Marco, M.P.J. Agric. Food Chem. 59 5036-5043, 2011

Protective effect of structurally diverse grapeprocyanidin fractions against UV-induced cell damageand deathMatito, C., Agell, N., Sánchez-Tena, S., Torres, J.L., Cascante,M.J. Agric. Food Chem. 59 4489-4495, 2011

Role of galloylation and polymerization incytoprotective effects of polyphenolic fractions againsthydrogen peroxide insultMitjans, M., Ugartondo, V., Martínez, V.,Touriño, S., Torres,J.L.; Vinardell, M.P.J. Agric. Food Chem. 59 2113-2119, 2011

Surface-active properties of lipophilic antioxidantstyrosol and hydroxytyrosol fatty acid esters: A potentialexplanation for the nonlinear hypothesis of theantioxidant activity in oil-in-water emulsions Lucas, R., Comelles, F., Alcántara, D., Maldonado, O.S.,Curcuroze, M., Parra, J.L., Morales, J.C. J. Agric. Food Chem. 58 8021-8026, 2010

Validation of an enzyme-linked immunosorbent assayfor detecting sulfonamides in feed resourcesJimenez, V., Adrian, J., Guiteras, J., Marco, M.P., Companyo, R.J. Agric. Food Chem. 58 7526-7531, 2010

Impact of thermal processing on the activity ofgallotannins and condensed tannins from Hamamelisvirginiana used as functional ingredients in seafood. González, M.J., Torres, J.L., Medina, I.J. Agric. Food Chem. 58 4274–4283, 2010

Galacto-configured aminocyclitol phytoceramides arepotent in vivo invariant natural killer T cell stimulators.Harrak, Y., Barra, C.M., Delgado, A., Castano, A. R., Llebaria, A. J. Am. Chem. Soc. 133 12079-12084, 2011

Polyhydroxylated bicyclic isoureas and guanidines arepotent glucocerebrosidase inhibitors and nanomolarenzyme activity enhancers in gaucher cells Trapero, A., Alfonso, I., Butters, T.D., Llebaria, A. J. Am. Chem. Soc. 133 5474-5484, 2011

The Impact of water on the OH + HOCl reaction. Gonzalez, J., Anglada, J.M., Buszek, R.J., Francisco, J.S. J. Am. Chem. Soc. 133 3345-3353, 2011

Highly polar carbohydrates stack onto DNA duplexes viaCH/π interactionsLucas, R., Gómez-Pinto, I., Aviñó, A., Reina, J.J., Eritja, R.,González, C., Morales, J.C.J. Am. Chem. Soc. 133 1909-1916, 2011

Determination of TCMTB and other fungicides in leatherFont, J., Reyes, M., Cuadros, S., Bacardit, A., Marsal, A. J. Am. Leather Chem. As. 106 341-348, 2011

Tailor-made biomaterials from collagenic wastes Catalina, M., Celma, P., Cot, J., Manich, A., Marsal, A. J. Am. Leather Chem. As. 106 153-160, 2011

Determination of dimethylfumarate in leather andfootwear by solid-phase micro extraction and gaschromatography-mass spectrometryCuadros, R.M., Font, J., Reyes, M., Ollé, Ll., Marsal, A.J. Am. Leather Chem. As. 105 395-400, 2010

Moisture sorption/desorption of collagen Manich, A.M., Maldonado, F., Carilla, J., Catalina, M., Marsal, A. J. Am. Leather Chem. As. 105 229-241, 2010

Application of gelatin extracted from chrome shavingson the glazed finishing of leatherCatalina, M., Attenburrow, G.E., Cot, J., Covington, A.D.,Antunes, A.P.M.J. Am. Leather Chem. As. 105 138-144, 2010

Synthesis and properties of ascorbyl esters catalyzed bylipozyme TL im using triglycerides as acyl donors Reyes-Duarte, D., López-Cortes, N., Torres, P., Comelles, F.,Parra, J.L., Peña, S., Ugidos, A.V., Ballesteros, A., Plou, F.J. J. Am. Oil Chem. Soc. 88 57-64, 2011

Evaluation of immunoassays as an alternative for therapid determination of pesticides in wine and grapesamples Argarate, N., Arestin, M., Ramón-Azcón, J., Alfaro, B.,Barranco, A., Sánchez-Baeza, F., Marco, M.P. J. AOAC Int. 93 2-11, 2010

Spectrally and temporarily resolved luminescence studyof short-range order in nanostructured amorphous ZrO2Tiseanu, C., Parvulescu, V.I., Sanchez-Dominguez, M.,Boutonnet, M.J. Appl. Phys. 110 103521, 2011


Influence of crosslinkers and crosslinking method on theproperties of gelatin films extracted from leather solidwasteCatalina, M., Attenburrow, G.E., Cot, J., Covington, A.D.,Antunes, A.P.M. J. Appl. Polym. Sci. 119 2105-2111, 2011

New anionic surface-active agent derived from woolproteins for hair treatment.Barba, C., Scott, S., Kelly, R., Parra, J.L., Coderch, L.J. Appl. Polym. Sci. 115 1461-1467, 2010

A phospholipid analog with potent antimalarial activity,inhibits Plasmodium falciparum CTP:phosphocholinecytidylyltransferase activityGonzález-Bulnes, P., Bobenchik, A.M., Augagneur, Y., Cerdan,R., Vial, H.J., Llebaria, A., Ben Mamoun, C. J. Biol. Chem. 286 28940-28947, 2011

Acid ceramidase expression modulates the sensitivity ofA375 melanoma cells to dacarbazine Bedia, C., Casas, J., Andrieu-Abadie, N., Fabriàs, G., Levade, T. J. Biol. Chem. 286 28200-28209, 2011

Regulation of CC ligand 5/RANTES by acidsphingomyelinase and acid ceramidase. Jenkins, R.W., Clarke, C.J., Canals, D., Snider, A.J., Gault,C.R., Heffernan-Stroud, L., Wu, B.X., Simbari, F., Roddy, P.,Kitatani, K., Obeid, L.M., Hannun, Y.A.J. Biol. Chem. 286 13292-13303. 2011

A novel mechanism of lysosomal acid sphingomyelinasematuration: requirement for carboxyl-terminalproteolytic processing. Jenkins, R.W., Idkowiak-Baldys, J., Simbari, F., Canals, D.,Roddy, P., Riner, C.D., Clarke, C.J., Hannun, Y.A. J. Biol. Chem. 286 3777-3788, 2011

Syntaxin 4 is required for acid sphingomyelinase activityand apoptotic functionPerrotta, C., Bizzozero, L., Cazzato, D., Morlacchi, S., Assi, E.,Simbari, F., Zhang, Y., Gulbins, E., Bassi, M.T., Rosa, P.,Clementi, E.J. Biol. Chem. 285 40240-40251, 2010

Regulated secretion of acid sphingomyelinase:Implications for selectivity of ceramide formationJenkins, R.W., Canals, D., Idkowiak-Baldys, J., Simbari, F.,Roddy, P., Perry, D.M., Kitatani, K., Luberto, C., Hannun, Y.A.J. Biol. Chem. 285 35706-35718, 2010

Antioxidant CR-6 protects against reperfusion injuryafter a transient episode of focal brain ischemia in ratsPérez-Asensio, F.J., De La Rosa, X., Jiménez-Altayó, F., Gorina,R., Martínez, E., Messeguer, A., Vila, E., Chamorro, A., Planas, A.M. J. Cerebr. Blood Flow Met. 30 638-652, 2010

Sex pheromone of the Spanish population of the beetarmyworm Spodoptera exiguaAcín, P., Rosell, G., Guerrero, A., Quero, C. J. Chem. Ecol. 36 778-786, 2010

Computational prediction of structure-Activityrelationships for the binding of aminocyclitols to β-glucocerebrosidase Díaz, L., Bujons, J., Delgado, A., Gutiérrez-De-Terán, H.,Åqvist, J. J. Chem. Inf. Model. 51 601-611, 2011

Evaluation of the nonlinear optical properties forannulenes with Hückel and Möbius topologies Torrent-Sucarrat, M., Anglada, J.M., Luis, J.M. J. Chem. Theor. Comput. 7 3935-3943, 2011

Anharmonicity and the Eigen-Zundel dilemma in the IRspectrum of the protonated 21 water cluster Torrent-Sucarrat, M., Anglada, J.M. J. Chem. Theory Comput. 7 467-472, 2011

On the dissociation of ground state trans -HOOO radical:A theoretical study Anglada, J.M., Olivella, S., Solé, A. J. Chem. Theory Comput. 6 2743-2750, 2010

Mass spectrometric characterization of urinarytoremifene metabolites for doping control analyses Gómez, C., Pozo, O.J., Diaz, R., Sancho, J.V., Vilaroca, E.,Salvador, J.P., Marco, M.P., Hernandez, F., Segura, J., Ventura,R. J. Chromatogr. A 1218 4727-4737, 2011

A high-throughput screening (HTS) immunochemicalmethod for the analysis of stanozolol metabolites incattle urine samplesSalvador, J.-P., Sánchez-Baeza, F., Marco, M.P. J. Chromatogr. B 878 243-252, 2010

Isolation and partial characterization of a biosurfactantmixture produced by Sphingobacterium sp. isolatedfrom soilBurgos-Díaz, C., Pons, R., Espuny, M.J., Aranda, F.J., Teruel,J.A., Manresa, A., Ortiz, A., Marqués, A.M.J. Colloid Interface Sci. 361 195-204, 2011

Analysis of HIV-1 fusion peptide inhibition by syntheticpeptides from E1 protein of GB virus C Sánchez-Martín, M.J., Hristova, K., Pujol, M., Gómara, M.J.,Haro, I., Alsina, M.A., Busquets, M.A. J. Colloid Interf. Sci. 360 124-131, 2011

Self-aggregation and antimicrobial activity ofimidazolium and pyridinium based ionic liquids inaqueous solution. Cornellas, A., Pérez, L., Comelles, F., Ribosa, I., Manresa, A.,García, M.T. J. Colloid Interface Sci. 355 164-171, 2011

Formation of polymeric nano-emulsions by a low-energymethod and their use for nanoparticle preparation Calderó, G., García-Celma, M.J., Solans, C. J. Colloid Interf. Sci. 353 406-411, 2011

Adsolubilisation of organic compounds onto collagenfibres Maldonado, F., Bautista, E., Manich, A.M., Marsal, A. J. Colloid Interf. Sci. 351 466-471, 2010

Nano-emulsions prepared by the phase inversioncomposition method: Preparation variables and scale up Solè, I., Pey, C.M., Maestro, A., González, C., Porras, M.,Solans, C., Gutiérrez, J.M.J. Colloid Interface Sci. 344 417-423, 2010

Effect of alkyl chain asymmetry on catanionic mixturesof hydrogenated and fluorinated surfactants Blanco, E., Rodríguez-Abreu, C., Schulz, P., Ruso, J.M.J. Colloid Interface Sci. 341, 261-266, 2010

Nanoconjugates as intracorporeal neutralizers ofbacterial endotoxins Vicent, M.J., Cascales, L., Carbajo, R.J., Cortés, N.,Messeguer, A., Pérez Payá, E. J. Control. Release 142 277-285, 2010

Damaged retrival with ceramide rich liposomes.Méndez, S., Manich, A.M., Martí, M., Parra, J.L., Coderch, L.J. Cosmet. Sci. 62 565-577, 2011

Skin efficacy of liposomes composed of internal woollipids rich in ceramides Ramírez, R., Martí, M., Barba, C., Méndez, S., Parra, J.L.,Coderch, L. J. Cosmet. Sci. 61 235-245, 2010

Synthesis of Pt nanoparticles in oil-in-watermicroemulsions: Phase behavior and effect offormulation parameters on nanoparticle characteristicsSanchez-Dominguez, M., Koleilat, H., Boutonnet, M., Solans, C.J. Dispersion Sci. Technol. 32 1765-1770, 2011

145


Evaluation of the structure-activity relationship ofthrombin binding aptamers by voltammetry and atomicforce microscopy. Diculescu, V.C., Chiorcea-Paquim, A.M., Eritja, R., Oliveira-Brett, A.M. J. Electroanal. Chem. 656 159-166, 2011

Fabrication of patterned surfaces by photo-lithographicexposure of DNA-hairpins carrying a novel photolabilegroup.Manning, B., Leigh, S.J., Ramos, R., Preece, J., Eritja, R.J. Exp. Nanosci. 5 26-39, 2010

Advanced oxidation of benzene, toluene, ethylbenzeneand xylene isomers (BTEX) by Trametes versicolor Aranda, E., Marco-Urrea, E., Caminal, G., Arias, M.E., García-Romera, I., Guillén, F. J. Hazard. Mater. 181 181-186, 2010

Naproxen degradation test to monitor Trametesversicolor activity in solid-state bioremediation processes Rodríguez-Rodríguez, C.E., Marco-Urrea, E., Caminal, G.J. Hazard. Mater. 179 1152–1155, 2010

Degradation of the drug sodium diclofenac by Trametesversicolor pellets and identification of someintermediates by NMRMarco-Urrea, E., Pérez-Trujillo, M., Cruz-Morató, C., Caminal,G., Vicent, T.J. Hazard. Mater. 176 836–842, 2010

Recognition of CD1d-{alpha}-C-galactosylceramide.Patel, O., Cameron, G., Pellicci, D.G., Liu, Z., Byun, H.S.,Beddoe, T., McCluskey, J., Franck, R.W., Castaño, A.R.,Harrak, Y., Llebaria, A., Bittman, R., Porcelli, S.A., Godfrey,D.I., Rossjohn, J. J. Immunol. 187 4705-4713, 2011

Bioassays of compounds with potential juvenoid activityon Drosophila melanogaster: Juvenile hormone III,bisepoxide juvenile hormone III and methyl farnesoatesHarshman, L.G., Song, K.-D., Casas, J., Schuurmans, A.,Kuwano, E., Kachman, S.D., Riddiford, L.M., Hammock, B.D.J. Insect Physiol. 56 1465-1470, 2010

A simple fluorogenic method for determination of acidceramidase activity and diagnosis of Farber disease Bedia, C., Camacho, L., Abad, J.L., Fabriàs, G., Levade, T. J. Lipid Res. 51 3542-3547, 2010

Inhibition of glucosylceramide synthesis affects cell cycleprogression, membrane trafficking and stagedifferentiation in the minimized protozoan Giardialamblia. Štefanic, S., Spycher, C., Morf, L., Fabriàs, G., Casas, J.,Schraner, E., Wild, P., Hehl, A.B., Sonda, S.J. Lipid Res. 51 2527-2545, 2010

The use of chimeric vimentin citrullinated peptides forthe diagnosis of rheumatoid arthritis Malakoutikhah, M., Gómara, M.J., Gómez-Puerta, J.A.,Sanmartí, R., Haro, I. J. Med. Chem. 54 7486-7492, 2011

Triazine-based vanilloid 1 receptor open channelblockers: Design, synthesis, evaluation, and SAR analysis Vidal-Mosquera, M., Fernández-Carvajal, A., Moure, A.,Valente, P., Planells-Cases, R., González-Ros, J.M., Bujons, J.,Ferrer-Montiel, A., Messeguer, A.J. Med. Chem. 54 7441-7452, 2011

Synthesis of antimitotic thioglycosides: in vitro and invivo evaluation of their anticancer activityGarcia-Alvarez, I., Groult, H., Casas, J., Barreda-Manso, M.A.,Yanguas-Casas, N., Nieto-Sampedro, M., Romero-Ramirez, L.,Fernandez-Mayoralas, A.J. Med. Chem. 54, 6949-6955, 2011

New glucocerebrosidase inhibitors by exploration ofchemical diversity of N-substituted aminocyclitols usingclick chemistry and in situ screening Díaz, L., Casas, J., Bujons, J., Llebaria, A., Delgado, A. J. Med. Chem. 54 2069-2079, 2011

Cationic surfactants derived from lysine: Effects of theirstructure and charge type on antimicrobial andhemolytic activities Colomer, A., Pinazo, A., Manresa, M.A., Vinardell, M.P.,Mitjans, M., Infante, M.R., Pérez, L. J. Med. Chem. 54 989-1002, 2011

Effect of synthetic peptides belonging to E2 envelopeprotein of GB virus C on human immunodeficiency virustype 1 infection Herrera, E., Tenckhoff, S., Gómara, M.J., Galatola, R., Bleda,M.J., Gil, C., Ercilla, G., Gatell, J.M., Tillmann, H.L., Haro, I. J. Med. Chem. 53 6054-6063, 2010

Click chemistry approach to new N-substitutedaminocyclitols as potential pharmacological chaperonesfor gaucher disease Díaz, L., Bujons, J., Casas, J., Llebaria, A., Delgado, A. J. Med. Chem. 53 5248-5255, 2010

Biofunctional textiles prepared with liposomes: In vivoand in vitro assessment Marti, M., Martínez, V., Rubio, L., Coderch, L., Parra, J.L. J. Microencapsul. 28 799-806, 2011

Effects of commercial non-ionic alkyl oxyethylene and ionic biocompatible arginine-based surfactants on the photophysical behaviour of severalpoly(fluorene-1,4-phenylene)Tapia, M.J., Monteserín, M., Costoyas, A., Burrows, H.D.,Marques, A.T., Pais, A.A.C.C., Valente, A.J.M., Mallavia, R.,Scherf, U., Pinazo, A., Pérez, L., Morán, M.C.J. Mol. Liq. 156 18-27, 2010

Reactivity versus steric effects in fluorinated ketones asesterase inhibitors: A quantum mechanical andmolecular dynamics study Rayo, J., Muñoz, L., Rosell, G., Hammock, B.D., Guerrero, A.,Luque, F.J., Pouplana, R. J. Mol. Model. 16 1753-1764, 2010. Int. workshop on“Modeling interaction in biomolecules IV”, 2009. ConferencePaper

neo-Clerodane diterpenoids from Ajuga bracteosaCastro, A., Coll, J., Arfan, M. J. Nat. Prod. 74 1036-1041, 2011

LC-MS-SPE-NMR for the isolation and characterization ofneo-clerodane diterpenoids from Teucrium luteumsubsp. flavovirens Castro, A., Moco, S., Coll, J., Vervoort, J. J. Nat. Prod. 73 962-965, 2010

A lyophilized red grape pomace containingproanthocyanidin-rich dietary fiber induces genetic andmetabolic alterations in colon mucosa of femaleC57BL/6J miceLizárraga, D., Vinardell, M.P., Noé, V., van Delft, J.H., Alcarraz-Vizán, G., van Breda, S.G., Staal, Y., Günter, U.L., Reed, M.A.,Ciudad, C.J., Torres, J.L., Cascante, M.J. Nutr. 141 1597-1604, 2011

Synthesis of oligonucleotides carrying amino lípidogroups at the 3’-end for RNA interference studies. Grijalvo, S., Ocampo, S.M., Perales, J.C., Eritja, R. J. Org. Chem. 75 6803-6813, 2010

Improved therapeutic responses for liposomaldoxorubicin targeted via thrombospondinpeptidomimetics versus untargeted doxorubicinRivera-Fillat, M.P., Reig, F., Martínez, E.M., Grau-Oliete, M.R.J. Pept. Sci. 16 315-321, 2010

Inhibition of electrophysiological response to thepheromone of the fall armyworm, SpodopterafrugiperdaPérez Luis, C.P., Guerrero, A., Malo, E.A.J. Pest. Sci. 35 23-26, 2010

Studies on controlled release of hydrophilic drugs fromW/O high internal phase ratio emulsions Calderó, G., Llinàs, M., García-Celma, M.J., Solans, C. J. Pharm. Sci. 99 701-711, 2010

146


Gas phase reaction of nitric acid with hydroxyl radicalwithout and with water. A theoretical investigation Gonzalez, J., Anglada, J.M. J. Phys. Chem. A 114 9151-9162, 2010

A Langmuir monolayer study of the interaction ofE1(145-162) hepatitis G virus peptide with phospholipidmembranes Sánchez-Martin, M.J., Haro, I., Alsina, M.A., Busquets, M.A.,Pujol, M. J. Phys. Chem. B 114 448-456, 2010

Modifying the heat transfer and capillary pressure ofloop heat pipe wicks with carbon nanotubesTerrado, E., Molina, R., Natividad, E., Castro, M., Erra, P.,Mishkinis, D., Torres, A., Martinez, M.T.J. Phys. Chem. C 115 9312–9319, 2011

Effects of smoking on disease activity and radiographicprogression in early rheumatoid arthritis Ruiz-Esquide, V., Gómez-Puerta, J.A., Cañete, J.D., Graell, E.,Vazquez, I., Ercilla, M.G., Viñas, O., Gómez-Centeno, A.,Haro, I., Sanmartí, R. J. Rheumatol. 38 2536-2539, 2011

Alternative fungicides: Comparisons with conventionalchemicalsCuadros, S., Manresa, Mª A., Font, J., Bautista, Mª E.,Maldonado, F., Marsal, A.J. Soc. Leath. Tech. Chem. 95 263-269, 2011

Leather ageing and hexavalent chromium formation asa function of the fatliquoring agent. Part III: Interactionwith synthetic and vegetable retanning agents Palop, R., Ballús, O., Manich, A.M., Marsal, A. J. Soc. Leath. Tech. Chem. 94 70-76, 2010

Moisture adsorption/desorption kinetics of bovine hidepowder Manich, A.M., Maldonado, F., Carilla, J., Catalina, M., Marsal, A. J. Soc. Leath. Tech. Chem. 94 15-20, 2010

Surfactants based on bis-galactobenzimidazolones:Synthesis, self-assembly and ion sensing properties Lakhrissi, L., Hassan, N., Lakhrissi, B., Massoui, M., Essassi,E.M., Ruso, J.M., Solans, C., Rodríguez-Abreu, C.J. Surfactants Deterg. 14 487-495, 2011

Preparation of a new oligomeric surfactant:N,N,N′,N″,N″-pentamethyl diethyleneamine—N,N″-di-[tetradecylammonium bromide] and the study of itsthermodynamic properties Alehyen, S., Bensajjay, F., El Achouri, M., Pérez, L., Pinazo, A.,Infante, M.R.J. Surfact. Deterg. 13 339-348, 2010

Surface and self-aggregation properties of bis-benzimidazolones derivatives of D-glucose Lakhrissi, B., Lakhrissi, L., Massoui, M., Essassi, E.M.,Comelles, F., Esquena, J., Solans, C., Rodríguez-Abreu, C. J. Surfact. Deterg.13 329-338, 2010

Study of the interaction between methyl orange andmono and bis-quaternary ammonium surfactants Alehyen, S., Bensejjay, F., El Achouri, M., Pérez, L., Infante, M.R.J. Surfact. Deterg. 13, 225-231, 2010

Water sorption of nails treated with wool keratinproteins and peptides Barba, C., Martí, M., Roddick-Lanzilotta, A., Manich, A.M.,Carilla, J., Parra, J.L., Coderch, L. J. Therm. Anal. Calorim. 104 323-329, 2011. (XVIth ISBCConference Paper)

Effect of wool keratin proteins and peptides on hairwater sorption kinetics Barba, C., Martí, M., Roddick-Lanzilotta, A., Manich, A.,Carilla, J., Parra, J.L., Coderch, L. J. Therm. Anal. Calorim. 102 43-48, 2010

Thermal transitions of polylactide false-twist texturedmultifilaments determined by DSC and TMA Manich, A.M., Carilla, J., Miguel, R.A.L., Lucas, J.M., Franco,F.G.F., Montero, L.A., Cayuela, D. J. Therm. Anal. Calorim. 99 723-731, 2010

Tuning high aqueous phase uptake in nonionic water-in-oil microemulsions for the synthesis of Mn-Zn ferritenanoparticles: Phase behavior, characterization, andnanoparticle synthesisAubery, C., Solans, C., Sanchez-Dominguez, M.Langmuir 27 14005-14013, 2011

Macroporous polymers obtained in highly concentratedemulsions stabilized solely with magnetic nanoparticles Vílchez, A., Rodríguez-Abreu, C., Esquena, J., Menner, A,Bismarck, A.Langmuir 27 13342-13352, 2011

Chromonic liquid crystalline phases of pinacyanolacetate: Characterization and use as templates for thepreparation of mesoporous silica nanofibers Rodríguez-Abreu, C., Torres, C.A., Tiddy, G.J.T.Langmuir, 27 3067-3073, 2011

Novel biocompatible DNA gel particles Morán, M.C., Infante, M.R., Miguel, M.G., Lindman, B., Pons, R. Langmuir 26 10606-10613, 2010

Application of bicellar systems on skin: Diffusion andmolecular organization effects Rodríguez, G., Rubio, L., Cócera, M., Estelrich, J., Pons, R., DeLa Maza, A., López, O. Langmuir 26 10578-10584, 2010

Use of hydrophobically modified inulin for thepreparation of polymethyl methacrylate/polybutylacrylate latex particles using a semicontinuous reactor Obiols-Rabasa, M., Ramos, J., Forcada, J., Esquena, J., Solans,C., Levecke, B., Booten, K., Tadros, T.F. Langmuir 26 7717-7724, 2010

Headgroup effects on the unusual lamellar-lamellarcoexistence and vesicle-to-micelle transition of salt-freecatanionic amphiphiles Silvas, B.F.B., Marques, E.F., Olsson, U., Pons, R. Langmuir 26 3058-3066, 2010

Dynamic properties of cationic diacyl-glycerol-arginine-based surfactant/phospholipid mixtures at the air/waterinterface Lozano, N., Pinazo, A., Pérez, L., Pons, R. Langmuir 26 2559-2566, 2010

Structure of aggregates in diluted aqueous octylglucoside/tetraethylene glycol monododecyl ethermixtures with different alkanols Pons, R., Valiente, M., Montalvo, G. Langmuir 26 2256-2262, 2010

New surfactant phosphine ligands and platinum(II)metallosurfactants. influence of metal coordination onthe critical micelle concentration and aggregationproperties Parera, E., Comelles, F., Barnadas, R., Suades, J. Langmuir 26 743-751, 2010

An EPR analysis of β-dimerization in α-blocked pyrrolesin oxidant conditions. Juliá, L., Rius, J., Torrelles, X. Magn. Reson. Chem. 49 164–167, 2011. ConferencePaper???

EPR/Spin-trapping study of free radical intermediates inthe photolysis of trifluoromethyl ketones with initiators. Rosa, E., Guerrero, A., Bosch, M.P., Julià, L.Magn. Reson. Chem. 48 198–204, 2010

Preparation of ultra-light magnetic nanocompositesusing highly concentrated emulsions Ghosh, G., Vilchez, A., Esquena, J., Solans, C., Rodríguez-Abreu, C. Mater. Chem. Phys. 130 786-793, 2011

147


Molecules that modulate Apaf-1 activity Pérez-Payá, E., Orzáez, M., Mondragón, L., Wolan, D., Wells,J.A., Messeguer, A., Vicent, M.J. Med. Res. Rev. 31 649-675, 2011

Synthesis and evaluation of xylopyranoside derivatives as "decoy acceptors" of human beta-1,4-galactosyltransferase 7Garcia-Garcia, J. F., Corrales, G., Casas, J., Fernandez-Mayoralas, A., Garcia-Junceda, E.Mol. Biosyst. 7 1312-1321, 2011

Lipid and ganglioside alterations in tumor cells treatedwith antimitotic oleyl glycoside. Garcia-Alvarez, I., Egido-Gabas, M., Romero-Ramirez, L.,Doncel-Pérez, E., Nieto-Sampedro, M., Casas, J., Fernandez-Mayoralas, A.Mol. Biosyst. 7 129-138, 2011

Synthesis and in vitro inhibition properties of siRNAconjugates carrying glucose and galactose with differentpresentation. Aviñó, A., Ocampo, S., Lucas, R., Reina, J.J., Morales, J.C.,Perales, J. C., Eritja, R. Mol. Divers. 15 751-757, 2011

Synthesis and properties of small interfering RNAduplexes carrying 5-ethyl residues. Terrazas M., Eritja R. Mol. Divers. 15 677-686, 2011

Retrospective mapping of SAR data for TTR protein inchemico-biological space using ligand efficiency indicesas a guide to drug discovery strategies Blasi, D., Arsequell, G., Valencia, G., Nieto, J., Planas, A.,Pinto, M., Centeno, N.B., Abad-Zapatero, C., Quintana, J. Mol. Inform. 30 161-167, 2011 (18th European Symposiumon Quantitative Structure-Activity Relationships, EuroQSAR2010. Conference Paper)

Proanthocyanidin metabolites associated with dietaryfibre from in vitro colonic fermentation andproanthocyanidin metabolites in human plasma.Saura-Calixto, F., Pérez-Jiménez, J., Touriño, S., Serrano, J.,Fuguet, E., Torres, J.L., Goñi, I.Mol. Nutr. Food Res. 54 939–946, 2010

Functionally enhanced siRNA targeting TNFα attenuatesDSS-induced colitis and TLR-mediatedimmunostimulation in miceOcampo, S.M., Romero, C., Aviñó, A., Burgueño, J., Gassull,M.A., Bermúdez, J., Eritja, R., Fernandez, E., Perales, J.C.Mol. Ther. 20 382-390, 2011

Solid-phase synthesis of oligodeoxynucleotidescontaining N 4-[2-(t-butyldisulfanyl)ethyl]-5-methylcytosine moietiesPérez-Rentero, S., Garibotti, A.V., Eritja, R.Molecules 15 5692-5707, 2010

A combination of hard and soft templating for thefabrication of silica hollow microcoils withnanostructured walls Rodríguez-Abreu, C., Vilanova, N., Solans, C., Ujihara, M.,Imae, T., López-Quintela, A., Motojima, S. Nanoscale Res. Lett. 6 330-337, 2011

Phytotoxic activity of flavonoids from DicranostylesamplaCastro, A., Cantrell, C.L., Hale, A.L., Duke, S.O. Nat. Prod. Commun. 5 1233-1237, 2010

Highly efficient aldol additions of DHA and DHAP to N-Cbz-amino aldehydes catalyzed by L-rhamnulose-1-phosphate and L-fuculose-1-phosphatealdolases in aqueous borate buffer.Garrabou, X., Joglar, J., Parella, T., Bujons J., Clapés, P.Org. Biomol. Chem. 9 8430-8436, 2011

Enzymatic enantiomeric resolution of phenylethylaminesstructurally related to amphetamine Muñoz, L., Rodríguez, A.M., Rosell, G., Bosch, M.P., Guerrero, A. Org. Biomol. Chem. 9 8171-8177, 2011

Synthesis, biological evaluation and structuralcharacterization of novel glycopeptide analogues ofnociceptin N/OFQ Arsequell, G., Rosa, M., Mayato, C., Dorta, R.L., Gonzalez-Nunez, V., Barreto-Valer, K., Marcelo, F., Calle, L.P., Vázquez,J.T., Rodríguez, R.E., Jiménez-Barbero, J., Valencia, G. Org. Biomol. Chem. 9 6133-6142, 2011

Bicyclic (galacto)nojirimycin analogues as glycosidaseinhibitors: effect of structural modifications in theirpharmacological chaperone potential towards β-glucocerebrosidaseAguilar-Moncayo, M., García-Moreno, M.I., Trapero, A.,Egido-Gabás, M., Llebaria, A., Fernández, J.M., Mellet, C.O. Org. Biomol. Chem. 3698-3713, 2011

Molecular recognition of N-protected dipeptides bypseudopeptidic macrocycles: A comparative study of thesupramolecular complexes by ESI-MS and NMR Alfonso, I., Bolte, M., Bru, M., Burguete, M.I., Luis, S.V.,Vicent, C. Org. Biomol. Chem. 8 1329-1339, 2010

A direct, efficient method for the preparation of siRNAscontaining ribo-like north bicyclo[3.1.0]hexanepseudosugarsTerrazas, M., Aviñò, A., Siddiqui, M.A., Marquez, V.E., Eritja, R.Org. Lett. 13 2888-2891, 2011

Synthesis of allylic trifluoromethyl ketones and activityas inhibitors of the sex pheromone of the leopard moth,Zeuzera pyrina L. (Lepidoptera: Cossidae)Muñoz, L., Bosch, M.P., Batllori, Ll., Rosell, G., Bosch, D.,Guerrero, A., Avilla, J.Pest Manag. Sci. 67 956-964, 2011

Structural versatility of bicellar systems and theirpossibilities as colloidal carriers Barbosa, L., Rodríguez, G., Cócera, M., Rubio, L., López-Iglesias, C., de la Maza, A., López, O. Pharmaceutics 3 636-664, 2011Lucyanna, B.-B., Gelen, R., Merce, C., Laia, R., Carmen, L., dela Alfons, M., Olga, L.

Surface versus volume effects in luminescent ceriananocrystals synthesized by an oil-in-watermicroemulsion method Tiseanu, C., Parvulescu, V.I., Boutonnet, M., Cojocaru, B.,Primus, P.A., Teodorescu, C.M., Solans C., SánchezDomínguez, M.Phys. Chem. Chem. Phys. 13 17135-17145, 2011

A new approach to local hardness.Gál, T., Geerlings, P., De Proft F., Torrent-Sucarrat, M.Phys. Chem. Chem. Phys. 13 15003-15015, 2011

Effect of the substituents on the reactivity of carbonyloxides. A theoretical study on the reaction ofsubstituted carbonyl oxides with water. Anglada, J.M., González, J., Torrent-Sucarrat, M.Phys. Chem. Chem. Phys. 13 13034-13045, 2011

The reactions of SO3 with HO2 radical and H2O…HO2radical complex. Theoretical study on the atmosphericformation of HSO5 and H2SO4Gonzalez, J., Torrent-Sucarrat, M., Anglada, J.M. Phys. Chem. Chem. Phys. 12 2116-2125, 2010

On the applicability of local softness and hardness Torrent-Sucarrat, M., De Proft, F., Ayers, P.W., Geerlings, P. Phys. Chem. Chem. Phys. 12 1072-1080, 2010

Behavioural and electrophysiological responses of theEuropean corn borer Ostrinia nubilalis to host-plantvolatiles and related chemicals Solé, J., Sans, A., Riba, M., Guerrero, A. Physiol. Entomol. 35 354-363, 2010

Polydispersity stabilizes biaxial nematic liquid crystalsBelli, S., Patti, A., Dijkstra, M., van Roij, R.Phys. Rev. Lett. 107 148303, 2011

148


ZmMYB31 directly represses maize lignin genes andredirects the phenylpropanoid metabolic flux. Fornal, Shi, X., Chai, C., Encina, A., Irar, S., Capellades, M.,Fuguet, E., Torres, J.L., Rovira, P., Puigdomènech, P., Rigau, J.,Grotewold, E., Gray, J., Caparrós-Ruiz, D.Plant J. 64 633-644, 2010

Changes in dynamics upon oligomerization regulatesubstrate binding and allostery in amino acid kinasefamily members.Marcos, M., Crehuet, R., Bahar I. PLoS Comput. Biol. 7 e1002201, 2011.doi:10.1371/journal.pcbi.1002201

On the conservation of the slow conformationaldynamics within the amino acid kinase family: NAGK theparadigm Marcos, E., Crehuet, R., Bahar, I. Plos Comput. Biol. 6 e1000738, 2010. doi: 10.1371/journal.pcbi.1000738

Characterization of an antennal carboxylesterase fromthe pest moth Spodoptera littoralis degrading a hostplant odorantDurand, N., Carot-Sans, G., Chertemps, T., Bozzolan, F., Party,V., Renou, M., Debernard, S., Rosell, G., Maïbèche-Coisne, M.PLoS ONE 6: e29147. doi:10.1371/journal.pone.0029147, 2010

Protein-protein interaction antagonists as novelinhibitors of non-canonical polyubiquitylation Scheper, J., Guerra-Rebollo, M., Sanclimens, G., Moure, A.,Masip, I., González-Ruiz, D., Rubio, N., Crosas, B., Meca-Cortés, O., Loukili, N., Plans, V., Morreale, A., Blanco, J.,Ortiz, A.R., Messeguer, A., Thomson, T.M. PLoS ONE 5 e11403, 2010.doi:10.1371/journal.pone.0011403, 2010

Novel properties of PES fabrics modified by coronadischarge and colloidal TiO2 nanoparticles Mihailovic, D., Šaponjic, Z., Radoicic, M., Molina, R., Radetic,T., Jovancic, P., Nedeljkovic, J., Radetic, M. Polym. Advan. Technol. 22 703–709, 2011

Multifunctional properties of polyester fabrics modifiedby corona discharge/air RF plasma and colloidal TiO2nanoparticles Mihailovic , D., Šaponjic, Z., Molina, R., Radoicic, M.,Esquena, J., Jovancic, P., Nedeljkovic, J., Radetic, M. Polym. Compos. 32 390-397, 2011

Control of metabolism and signaling of simple bioactivesphingolipids: Implications in disease Gangoiti, P., Camacho, L., Arana, L., Ouro, A., Granado,M.H., Brizuela, L., Casas, J., Fabriás, G., Abad, J.L., Delgado,A., Gómez-Muñoz, A. Prog. Lipid Res. 49 316-334, 2010

Inhibition of acid ceramidase by a 2-substitutedaminoethanol amide synergistically sensitizes prostatecancer cells to N-(4-hydroxyphenyl) retinamide Gouazé-Andersson, V., Flowers, M., Karimi, R., Fabriás, G.,Delgado, A., Casas, J., Cabot, M.C. Prostate 71 1064-1073, 2011

Pentacoordinated phosphorus revisited by high-levelQM/MM calculations Marcos, E., Field, M.J., Crehuet, R. Proteins 78 2405-2411, 2010

Spectrometric study of the oligodeoxyribonucleotideprotonation in aqueous solution. Gargallo, R., Eritja, R., Kudrev, A.G.Russ. J. Gen. Chem. 80 (3) 485-492, 2010

Capture and culturing of living cells on microstructuredDNA substrates.Reisewitz, S., Schroeder, H., Tort, N., Edwards, K.A.,Baeumner, A.J., Niemeyer, C.M.Small 6 2162-2168, 2010

Intracellular silicon chips in living cellsGómez-Martínez, R., Vázquez, P., Duch, M., Muriano, A.,Pinacho, D., Sanvicens, N., Sánchez-Baeza, F., Boya, P., de laRosa, E.J., Esteve, J., Suárez, T., Plaza, J.A.Small 6 499-502, 2010

Stimulus responsive self-assembly of Gemini AmphiphilicPseudopeptides Rubio, J., Alfonso, I., Burguete, M.I., Luis, S.V. Soft Matter 7 10737-10748, 2011

Characterisation of skin states by non-crystallinediffraction Cócera, M., Rodríguez, G., Rubio, L., Barbosa-Barros, L.,Benseny-Cases, N., Cladera, J., Sabés, M., Fauth, F., de LaMaza, A., López, O. Soft Matter 7 8605-8611, 2011

Structural effects of flufenamic acid in DPPC/DHPCbicellar systems Rubio, L., Rodríguez, G., Alonso, C., López-Iglesias, C.,Cócera, M., Coderch, L., de La Maza, A., Parra, J.L., López, O. Soft Matter 7 8488-8497, 2011

Aqueous phase behaviour of choline carboxylatesurfactants-exceptional variety and extent of cubicphases Klein, R., Tiddy, G.J.T., Maurer, E., Touraud, D., Esquena, J.,Tache, O., Kunz, W. Soft Matter 7 6973-6983, 2011

An unexpected access to a new sphingoid basecontaining a vinyl sulfide unit.Nieves, I., Garrido, M., Abad, J. L., Delgado, A.Synlett 2950-2952, 2010

Improved microwave-assisted ring opening of 1,1,1-trifluoro-2,3-epoxypropane: Synthesis of new 3-alkoxy-1,1,1-trifluoropropan-2-ols Rayó, J., Muñoz, L., Rosell, G., Bosch, M.P., Guerrero, A. Synthesis 3117-3120, 2010

Development of an immunoassay for terbutryn: Study ofthe influence of the immunization protocol.Sanvicens, N., Varela, B., Ballesteros, B., Marco, M.P. Talanta 89 310-316, 2011

Development of a cellular biosensor for the detection of2,4,6-trichloroanisole (TCA) Varelas, V., Sanvicens, N., Marco, M.P., Kintzios, S. Talanta 84 936-940, 2011

Synthesis and characterization of phenolic antioxidantswith surfactant properties: Glucosyl- and glucuronosylalkyl gallates Maldonado, O.S., Lucas, R., Comelles, F., Jesús González, M.,Parra, J.L., Medina, I., Morales, J.C. Tetrahedron 67 7268-7279, 2011

Synthesis of a new stable and water-soluble tris(4-hydroxysulfonyltetrachlorophenyl)methyl radicalwith selective oxidative capacity. Mesa, J.A., Velázquez-Palenzuela, A., Brillas, E., Torres, J.L.,Juliá, L.Tetrahedron 67 3119-3123, 2011

Optically active macrocyclic hexaazapyridinophanesdecorated at the periphery: Synthesis and applications inthe NMR enantiodiscrimination of carboxylic acids Busto, E., González-Álvarez, A., Gotor-Fernández, V., Alfonso,I., Gotor, V. Tetrahedron 66 6070-6077, 2010

Peptoids bearing tertiary amino residues in the n-alkylside chains: synthesis of a potent inhibitor ofSemaphorin 3A Messeguer, J., Masip, I., Montolio, M., del Rio, J.A., Soriano,E., Messeguer, A. Tetrahedron 66 2444-2454, 2010

Gemini amphiphilic pseudopeptides: Synthesis andpreliminary study of their self-assembling properties Rubio, J., Alfonso, I., Bru, M., Burguete, M.I., Luis, S.V. Tetrahedron Lett. 51 5861-5867, 2010

149


Texturing, stretching and relaxation behaviour ofpolylactide multifilament yarns Manich, A.M., Miguel, R., Lucas, J., Franco, F., Baena, B.,Carilla, J., Montero, L., Cayuela, D. Text. Res. J. 81 1788-1795, 2011

Liposome as dispersing agent into disperse dyeformulation Marti, M., de la Maza, A., Parra, J.L., Coderch, L. Text. Res. J. 81 379-387, 2011

Skin delivery of caffeine contained in biofunctionaltextiles Rubio, L., Alonso, C., Coderch, L., Parra, J.L., Martí, M.,Cebrián, J., Navarro, J.A., Lis, M., Valldeperas, J. Text. Res. J. 80 1214-1221, 2010

Influence of internal lipids on dyeing of wool fibres .Martí, M., Ramírez, R., Barba, C., Coderch, L., Parra, J.L.Text. Res. J. 80 365-373, 2010

The reaction between HO and (H2O)n (n 5 1, 3) clusters:reaction mechanisms and tunneling effects.Gonzalez, J., Caballero, M., Aguilar-Mogas, A., Torrent-Sucarrat, M., Crehuet, R., Solé, A., Giménez, X., Olivella, S.,Bofill, J.M., Anglada, J.M. Theor. Chem. Acc. 128 579-592, 2011

Water absorption/desorption of human hair and nails Barba, C., Martí, M., Manich, A.M., Carilla, J., Parra, J.L.,Coderch, L. Thermochim. Acta 503-504 33-39, 2010

Biosensors for pharmaceuticals based on noveltechnology Sanvicens, N., Mannelli, I., Salvador, J.-P., Valera, E., Marco,M.-P. Trac-Trend. Anal. Chem.30 541-553, 2011

Identification and characterization of organicnanoparticles in food Peters, R., ten Dam, G., Bouwmeester, H., Helsper, H., Weigel,S., Allmaier, G., vd Kammer, F., Ramsch, R., Solans, C.,Tomaniová, M., Hajslova, J.TrAC-Trend. Anal. Chem. 30 100-112, 2011

Reference materials for measuring the size ofnanoparticles Linsinger, T.P.J., Roebben, G., Solans, C., Ramsch, R.TrAC- Trend. Anal. Chem. 30 19-27, 2011

Oxidation of atenolol, propranolol, carbamazepine andclofibric acid by a biological Fenton-like systemmediated by the white-rot fungus Trametes versicolorMarco-Urrea, E., Radjenovic, J., Caminal, G., Petrovic, M.,Vicent, T., Barceló, D.Water Res. 44 521–532, 2010

Recovery of proteins from wastewater of tannerybeamhouse operations: Influence on the main pollutionparameters Marsal, A., Hernández, E., Cuadros, S., Puig, R., Bautista, E.,Font, J. Water Sci. Technol. 62 658-666, 2010

150


The new EULAR/ACR classification ACPA cutoff levels aremarkers of poor radiological outcome in earlyrheumatoid arthritis.Gomez-Puerta, J.A, Ruiz-Esquide, V., Hernández, M.V., Graell,E., Cabrera, S. Gómara, M.J., Cañete, J.D., Haro, I andSanmartí, R.Arthritis Rheum. 63, S118, 2011

Smoking impact on radiographic progression in an earlyrheumatoid arthritis cohortRuiz-Esquide, V., Gomez-Puerta, J.A., Cabrera, S., Cañete,J.D., Hernández, M.V., Graell, E., Ercilla, G., Viñas, O.,Gómara, M.J., Haro, I and Sanmartí, R.Arthritis Rheum. 63, S831-S832, 2011

Crystal structure of the N-benzyloxycarbonyl-alanyl-phenylalanyl-methyl ester: the importance of the H-bonding patternAlfonso, I., Bolte, M., Burguete, M.I., Luis, S.V.Crystals 1 163-170, 2011

Differential scanning calorimetry and elasticity oftextured, heat set and mechanical strained polylactidemultifilamentsManich, A.M., Carilla, J., Miguel, R.A.L., Baena, B., Lucas, J.,Martí, M., Cayuela, D.Fib. Text. East Eur. 89 22-27, 2011

Preparation and AFM-characterization of self-assembledmonolayers functionalized with a thrombin bindingaptamer. Manning, B., Gállego, I., Tintoré, M., Fàbrega, C., Aviñó, A.,Eritja, R.Int. Rev. Biophys. Chem. 2 74-77, 2011

Branched RNA: a new architecture for RNA interference.Aviñó, A., Ocampo, S.M., Perales, J.C., Eritja, R. J. Nucleic Acids, ID 586935, 7 pages, 2011.doi:10.4061/2011/586935 (2011). PMID: 21461398.

G-quadruplex Nucleic Acids Eritja, R., Mergny, J.L., Montesarchio, D., Spindler, L., Webbada Silva, M. J. Nucleic Acids, ID 147650, 2 pages, 2010.doi:10.4061/2010/147650; PMID: 20814544. Editorial.

Development of a novel fluorescence assay based on theuse of the thrombin binding aptamer for the detectionof O6-alkylguanine-DNA alkyltransferase activity Tintoré, M., Aviñó, A., Ruiz, F.M., Eritja, R., Fàbrega, C. J. Nucleic Acids, ID 632041, 9 pages, 2010.doi:10.4061/2010/632041, PMID: 20936180.

Synthesis and structural properties of G,T-parallel clampscarrying 8-aminopurine residues Aviñó, A., Cubero, E., Gargallo, R., González, C., Orozco, M.,Eritja, R. J. Nucleic Acids, ID 763658, 11 pages, 2010.doi:10.4061/2010/763658; PMID: 20798879.

Thrombin binding aptamer quadruplex formation: AFMand voltammetric characterization.Diculescu, V.C., Chiorcea-Paquim, A.M., Eritja, R., Oliveira-Brett, A.M.J. Nucleic Acids, ID 841932, 8 pages, 2010.doi:10.4061/2010/841932; PMID: 20798847.

Synthesis and G-quadruplex binding properties ofdefined acridine oligomers.Ferreira, R., Aviñó, A., Pérez-Tomás, R., Gargallo, R., Eritja, R. J. Nucleic Acids, ID 489060, 10 pages, 2010.doi:10.4061/2010/489060; PMID: 20725626.

Synthesis and properties of oligodeoxynucleotidescarrying 2-aminopurine.Fàbrega, C., Grijalvo, S., Eritja, R. Open Org. Chem. J. 5 1-8, 2011

Mechanical properties, relaxation behaviour andthermal characterization of false-twist texturedpolylactide multifilament Manich, A.M., Carilla, J., Miguel, R.A.L., Lucas, J., Franco, F.,Montero, L., Cayuela, D. Vlakna a Textil 17 14-20, 2010

PUBLICATIONS (papers in NON-ISI journals, international)

151

Els químics i el descobriment de fàrmacs: un repte i unanecessitatMesseguer, A.Educació Química: EduQ. 5 4-10, 2010

La Comissió Lexicogràfica de Ciències. Un record encaraviu.Messeguer, A.Terminàlia 4, pp. 70-71 (2011).

Liposomas de fosfatidilcolina: un tensioactivo natural ybiológico como agente dispersanteMartí, M., Coderch, L., de la Maza, A., Parra, J.L.Boletin de la Asociación Química Española de la Industria delCuero 61 50-55, 2010

PUBLICATIONS (papers in NON-ISI journals, Spanish/Catalan)

Acerola and cashew apple as sources of antioxidants anddietary fibre Rufino, M.D.S.M., Pérez-Jiménez, J., Tabernero, M., Alves,R.E., De Brito, E.S., Saura-Calixto, F.Int. J. Food Sci. Technol. 45 2227–2233, 2010

Current-voltage characteristic of electrospray processesin microfluidicsGundabala, V.R., Vilanova, N., Fernández-Nieves, A.Phys. Rev. Lett. 105, 154503, 2010

Relaxation dynamics in the columnar liquid crystal phaseof hard plateletsPatti, A., Belli, S., van Roij, R., Dijkstra, M.Soft Matter 7 3533-3545, 2011

PUBLICATIONS (of new IQAC members)


Rodríguez-Abreu, C., Esquena, J. Preparation of Mesoporous Materials withNonhydrocarbon Surfactants,in Self-Organized Surfactant Structures (ed T. F. Tadros). Ch11, 213-238, 2010Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany.doi:10.1002/9783527632633.

Maestro, A., Nolla, J., González, C., Gutiérrez, J. M. Worm-Like Micelles in Diluted Mixed SurfactantSolutions: Formation and Rheological Behavior,in Self-Organized Surfactant Structures (ed T. F. Tadros). Ch12, 239-257, 2010Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany.doi:10.1002/9783527632633.

Reddy, G.V.P., Guerrero, A. New Pheromones and Insect Control Strategiesin Pheromones (ed G. Litwack). Vitamins and Hormones, Vol.83, Ch 20, 493-519, 2010Academic Press (Elsevier). ISBN: 978-0-12-381516-3.

Mondragón, L., Orzáez, M., Gortat, A., Sancho, M.,Messeguer, A., Vicent, M.J., Pérez-Payá, E. Molecules that Bind a Central Protein Component of theApoptosome, Apaf-1, and Modulate its Activity. in Apoptosome: An-up-and-coming therapeutical tool (eds F.Cecconi, M. D'Amelio). Ch 4, 75-94, 2010Springer (Springer Science+Business Media)ISBN 978-90-481-3414-4

Benincasa, M., Marqués, A., Pinazo, A., Manresa, A. Rhamnolipid Surfactants: Alternative Substrates, NewStrategies in Biosurfactants (ed R. Sen). Section III, 170-184, 2010Advances in Experimental Medicine and Biology, Vol. 672Springer New York. DOI: 10.1007/978-1-4419-5979-9_13

Pons, R., Moran, M.C., Infante, M.R., Pinazo, A., Pérez, L. Lysine-Based Surfactantsin Colloids in Biotechnology (ed M. Fanun). Surfactant ScienceSeries, Vol. 152, 125-138, 2010CRC Press (Taylor and Francis). ISBN 9781439830802

Moran, C., Pérez, L., Pons, R., Pinazo, A., Infante, M.R. Amino Acids, Lactic Acid and Ascorbic Acid as RawMaterials for Biocompatible Surfactantin Surfactants from Renewable Resources (eds M. Kjellin, I.Johansson). Ch 5, 85-107, 2010John Wiley & Sons, Ltd, Chichester, UK.doi:10.1002/9780470686607.

De Persiis, F., Pons, R., Pucci, C., Tardani, F., La Mesa, C. Binding of Protein-Functionalized Entities onto SyntheticVesicles in Non-Viral Gene Therapy, (ed. Xu-bo Yuan). 645-660, 2011InTech (Available from:http://www.intechopen.com/articles/show/title/binding-of-protein-functionalized-entities-onto-synthetic-vesicles)ISBN: 978-953-307-538-9

Pinazo, A., Pérez, L., Infante, M.R., Vinardell, M.P., Mitjans,M., Morán, M.C., Martínez, V. Chemical Structure and Toxicity in Arginine-BasedSurfactantsin Arginine Amino Acid (ed N.L. Jacobs). MicrobiologyResearch Advances Series 125-142, 2011Nova Science Publishers Inc. ISBN: 978-1-61761-981-6

Sanvicens, N., Fernández, F., Salvador, J.P., Marco, M.P. Current Status and Future Prospects for Nanoparticle-Based Technology in Human Medicinein Nanoplatform-Based Molecular Imaging (ed X. Chen). Ch32, 781-813, 2011John Wiley & Sons, Inc., Hoboken, NJ, USA. doi: 10.1002/9780470767047.

Ghosh, G., Vílchez, A., Esquena, J., Solans, C., Rodríguez-Abreu, C.Preparation of porous magnetic nanocompositematerials using highly concentrated emulsions astemplatesin Trends in Colloid and Interface Science XXIV (eds V. Starov,K. Procházka). Progress in Colloid and Polymer Science, Vol.138, 161-164, 2011Springer. ISBN 978-3-642-19037-7

Clapés, P., Fessner, W.-D. Enzymatic direct aldol additionsin Science of Synthesis. Stereoselective Synthesis, Vol 2:Stereoselective Reactions of Carbonyl and Imino Groups (edG.A. Molander), Ch. 14, 677-734, 2011Georg Thieme Verlag KG, Stuttgart (Germany) ISBN: 9783131664211

Barba, C., Martí, M., Roddick-Lanzilotta, A., Manich, A.,Carilla, J., Parra, J.L., Coderch, L. Water Sorption of Human Keratinized Fibers: Effect ofWool Keratin Proteins and Peptides. in Keratin: Structure, Properties and Applications (eds R.Dullaart, J. Mousquès) Protein Biochemistry, Synthesis,Structure and Cellular Functions Series, Ch. 4, 89-111, 2011Nova Science Publishers, Inc. ISBN: 978-1-62100-336-6

Martí, M., Parra, J.L., Coderch, L. Lipid Role in Wool Dyeing in Natural Dyes (ed E. Perrin Akçakoca Kumbasar) Ch. 5, 80-100, 2011InTech. ISBN: 978-953-307-783-3.

Barba, C., Scott, S., Roddick-Lanzilotta, A., Parra, J.L.,Coderch, L.Keratin Proteins and Peptides from Wool, for HairRestoration. in Advances in Medicine and Biology (ed. L.V Berhardt) Vol. 5,Ch. 13, 237-242, 2011Nova Science Publishers, Inc. ISBN: 978-1-60456-557-7

Muriano, A., Salvador, J.P., Galve, R., Marco, M.P., Anisha,T.K.N., Loza-Alvarez, P., Soria, S. High sensitive non-linear detection of steroids byresonant double grating waveguide structures basedimmunosensors in Integrated Optics: Devices, Materials, and Technologies XV(eds J.E. Broquin, G. Nunzi Conti). Proc. SPIE 7941, 794114,2011http://dx.doi.org/10.1117/12.876456

Aviñó, A., Grijalvo, S., Pérez-Rentero, S., Garibotti, A.,Terrazas, M., Eritja, R.Synthesis of oligonucleotide-peptide conjugates forbiomedical and technological applications. in Bioconjugation Protocol: Strategies and Methods 2nd ed.(ed S. Mark). Methods in Molecular Biology Series Vol. 751Ch 14, 223-238, 2011Humana Press, Springer, New York. ISBN 978-1-61779-150-5

Messeguer, A.Fronteras del Conocimiento Actual en Químicain Física y Química. Complementos de formación disciplinar(Caamaño, A. coord.). Ch 5, 89-100, 2011 "Materiales parala formación del profesorado de la Educación Secundaria"Editorial Graó

BOOK CHAPTERS

152


institute of advanced chemistry of catalonia - IQAC-CSIC

Documents

Transcript of institute of advanced chemistry of catalonia - IQAC-CSIC