Multivalent glycoconjugates as anti-pathogenic agents

Anna Bernardi; Jesus Jiménez-Barbero; Alessandro Casnati; Cristina De Castro; Tamis Darbre; Franck Fieschi; Jukka Finne; Horst Funken; Karl-Erich Jaeger; Martina Lahmann; Thisbe K. Lindhorst; Marco Marradi; Paul Messner; Antonio Molinaro; Paul V. Murphy; Cristina Nativi; Stefan Oscarson; Soledad Penadés; Francesco Peri; Roland J. Pieters; Olivier Renaudet; Jean-Louis Reymond; Barbara Richichi; Javier Rojo; Francesco Sansone; Christina Schäffer; W. Bruce Turnbull; Trinidad Velasco-Torrijos; Sébastien Vidal; Stéphane Vincent; Tom Wennekes; Han Zuilhof; Anne Imberty

doi:10.1039/C2CS35408J

Multivalent glycoconjugates as anti-pathogenic agents†

Anna Bernardi,^a Jesus Jiménez-Barbero,^b Alessandro Casnati,^c Cristina De Castro,^d Tamis Darbre,^e Franck Fieschi,^f Jukka Finne,^g Horst Funken,^h Karl-Erich Jaeger,^h Martina Lahmann,ⁱ Thisbe K. Lindhorst,^j Marco Marradi,^k Paul Messner,^l Antonio Molinaro,^d Paul V. Murphy,^m Cristina Nativi,ⁿ Stefan Oscarson,^o Soledad Penadés,^k Francesco Peri,^p Roland J. Pieters,^q Olivier Renaudet,^r Jean-Louis Reymond,^e Barbara Richichi,ⁿ Javier Rojo,^s Francesco Sansone,^c Christina Schäffer,^l W. Bruce Turnbull,^t Trinidad Velasco-Torrijos,^u Sébastien Vidal,^v Stéphane Vincent,^w Tom Wennekes,^x Han Zuilhof^xy and Anne Imberty*^z

Author affiliations

* Corresponding authors

^a Università di Milano, Dipartimento di Chimica Organica e Industriale and Centro di Eccellenza CISI, via Venezian 21, 20133 Milano, Italy

^b Centro de Investigaciones Biológicas, CSIC, 28040 Madrid, Spain

^c Università degli Studi di Parma, Dipartimento di Chimica, Parco Area delle Scienze 17/a, 43100 Parma, Italy

^d Department of Chemical Sciences, Università di Napoli Federico II, Complesso Universitario Monte Santangelo, Via Cintia 4, I-80126 Napoli, Italy

^e Department of Chemistry and Biochemistry, University of Berne, Freiestrasse 3, Berne, Switzerland

^f Institut de Biologie Structurale, 41 rue Jules Horowitz, 38027 Grenoble Cedex 1, France

^g Department of Biosciences, University of Helsinki, P. O. Box 56, FI-00014 Helsinki, Finland

^h Institute of Molecular Enzyme Technology, Heinrich-Heine-University Düsseldorf, Forschungszentrum Jülich, D-42425 Jülich, Germany

ⁱ School of Chemistry, Bangor University, Deiniol Road Bangor, Gwynedd LL57 2UW, UK

^j Otto Diels Institute of Organic Chemistry, Christiana Albertina University of Kiel, Otto-Hahn-Platz 3-4, D-24098 Kiel, Germany

^k Laboratory of GlycoNanotechnology, CIC biomaGUNE and CIBER-BBN, P° de Miramón 182, 20009 San Sebastián, Spain

^l Department of NanoBiotechnology, NanoGlycobiology Unit, University of Natural Resources and Life Sciences, Muthgasse 11, A-1190 Vienna, Austria

^m School of Chemistry, National University of Ireland, Galway, University Road, Galway, Ireland

ⁿ Dipartimento di Chimica, Universitá degli Studi di Firenze, Via della Lastruccia, 13, I-50019 Sesto Fiorentino – Firenze, Italy

^o Centre for Synthesis and Chemical Biology, UCD School of Chemistry and Chemical Biology, University College Dublin, Belfield, Dublin 4, Ireland

^p Organic and Medicinal Chemistry, University of Milano-Bicocca, Piazza della Scienza, 2, 20126 Milano, Italy

^q Department of Medicinal Chemistry and Chemical Biology, Utrecht Institute for Pharmaceutical Sciences, Utrecht University, P.O. Box 80082, 3508 TB Utrecht, The Netherlands

^r Département de Chimie Moléculaire, UMR-CNRS 5250 & ICMG FR 2607, Université Joseph Fourier, 38041 Grenoble Cedex 9, France

^s Glycosystems Laboratory, Instituto de Investigaciones Químicas, CSIC – Universidad de Sevilla, Av. Américo Vespucio, 49, Seville 41092, Spain

^t School of Chemistry and Astbury Centre for Structural Molecular Biology, University of Leeds, Leeds, UK

^u Department of Chemistry, National University of Ireland, Maynooth, Maynooth Co. Kildare, Ireland

^v Institut de Chimie et Biochimie Moléculaires et Supramoléculaires UMR 5246, CNRS, Université Claude Bernard Lyon 1, 43 Boulevard du 11 Novembre 1918, F-69622 Villeurbanne, France

^w University of Namur (FUNDP), Département de Chimie, Laboratoire de Chimie Bio-Organique, rue de Bruxelles 61, B-5000 Namur, Belgium

^x Laboratory of Organic Chemistry, Wageningen University, Dreijenplein 8, 6703 HB Wageningen, The Netherlands

^y Department of Chemical and Materials Engineering, King Abdulaziz University, Jeddah, Saudi Arabia

^z Centre de Recherche sur les Macromolécules Végétales (CERMAV – CNRS), affiliated with Grenoble-Université and ICMG, F-38041 Grenoble, France
E-mail: Imberty@cermav.cnrs.fr

Abstract

Multivalency plays a major role in biological processes and particularly in the relationship between pathogenic microorganisms and their host that involves protein–glycan recognition. These interactions occur during the first steps of infection, for specific recognition between host and bacteria, but also at different stages of the immune response. The search for high-affinity ligands for studying such interactions involves the combination of carbohydrate head groups with different scaffolds and linkers generating multivalent glycocompounds with controlled spatial and topology parameters. By interfering with pathogen adhesion, such glycocompounds including glycopolymers, glycoclusters, glycodendrimers and glyconanoparticles have the potential to improve or replace antibiotic treatments that are now subverted by resistance. Multivalent glycoconjugates have also been used for stimulating the innate and adaptive immune systems, for example with carbohydrate-based vaccines. Bacteria present on their surfaces natural multivalent glycoconjugates such as lipopolysaccharides and S-layers that can also be exploited or targeted in anti-infectious strategies.

This article is part of the themed collection: Multivalent scaffolds in glycosciences

Chemical Society Reviews

Multivalent glycoconjugates as anti-pathogenic agents†

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