title: Pillar[5]arene-Based Glycoclusters: Synthesis and Multivalent Binding to Pathogenic Bacterial Lectins.
abstract: The synthesis of pillar[5]arene-based glycoclusters has been readily achieved by CuAAC conjugations of azido- and alkyne-functionalized precursors. The lectin binding properties of the resulting glycosylated multivalent ligands have been studied by at least two complementary techniques to provide a good understanding. Three lectins were selected from bacterial pathogens based on their potential therapeutic applications as anti-adhesives, namely LecA and LecB from Pseudomonas aeruginosa and BambL from Burkholderia ambifaria. As a general trend, multivalency improved the binding to lectins and a higher affinity can be obtained by increasing to a certain limit the length of the spacer arm between the carbohydrate subunits and the central macrocyclic core.
authors: University of Namur (UNamur), Académie Louvain, Département de Chimie, Laboratoire de Chimie Bio-Organique, rue de Bruxelles 61, 5000, Belgium.
authors: Kevin
authors: K
authors: Buffet
authors: Laboratoire de Chimie des Matériaux Moléculaires, Université de Strasbourg et CNRS (UMR 7509), Ecole Européenne de Chimie, Polymères et Matériaux (ECPM), 25 rue Becquerel, 67087, Strasbourg Cedex 2, France.
authors: Iwona
authors: http://orcid.org/0000-0003-0501-6768
authors: I
authors: Nierengarten
authors: Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, CO2-Glyco, UMR 5246, CNRS, Université Claude Bernard Lyon 1, 43 Boulevard du 11 Novembre 1918, 6922, Villeurbanne, France.|CERMAV-CNRS, Université Grenoble Alpes, BP 53, 38041, Grenoble, France.
authors: Nicolas
authors: N
authors: Galanos
authors: CERMAV-CNRS, Université Grenoble Alpes, BP 53, 38041, Grenoble, France.
authors: Emilie
authors: E
authors: Gillon
authors: Laboratoire de Chimie des Matériaux Moléculaires, Université de Strasbourg et CNRS (UMR 7509), Ecole Européenne de Chimie, Polymères et Matériaux (ECPM), 25 rue Becquerel, 67087, Strasbourg Cedex 2, France.
authors: Michel
authors: M
authors: Holler
authors: CERMAV-CNRS, Université Grenoble Alpes, BP 53, 38041, Grenoble, France. anne.imberty@cermav.cnrs.fr.
authors: Anne
authors: http://orcid.org/0000-0001-6825-9527
authors: A
authors: Imberty
authors: School of Pharmacy, University of East Anglia, Norwich, NR4 7TJ, United Kingdom.
authors: Susan E
authors: http://orcid.org/0000-0001-8821-0851
authors: SE
authors: Matthews
authors: Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, CO2-Glyco, UMR 5246, CNRS, Université Claude Bernard Lyon 1, 43 Boulevard du 11 Novembre 1918, 6922, Villeurbanne, France. sebastien.vidal@univ-lyon1.fr.
authors: Sébastien
authors: S
authors: Vidal
authors: University of Namur (UNamur), Académie Louvain, Département de Chimie, Laboratoire de Chimie Bio-Organique, rue de Bruxelles 61, 5000, Belgium. stephane.vincent@unamur.be.
authors: Stéphane P
authors: SP
authors: Vincent
authors: Laboratoire de Chimie des Matériaux Moléculaires, Université de Strasbourg et CNRS (UMR 7509), Ecole Européenne de Chimie, Polymères et Matériaux (ECPM), 25 rue Becquerel, 67087, Strasbourg Cedex 2, France. nierengarten@unistra.fr.
authors: Jean-François
authors: http://orcid.org/0000-0002-3333-9372
authors: JF
authors: Nierengarten
mesh_terms: D001426:Bacterial Proteins / Q000737:chemistry* / Q000378:metabolism; D047250:Calixarenes; D006001:Glycoconjugates / Q000737:chemistry*; D037102:Lectins / Q000737:chemistry* / Q000378:metabolism; D008958:Models, Molecular; D011485:Protein Binding; D011550:Pseudomonas aeruginosa / Q000737:chemistry*; D000644:Quaternary Ammonium Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001426:Bacterial Proteins; D006001:Glycoconjugates; D037102:Lectins; D000644:Quaternary Ammonium Compounds; C570642:pillar(5)arene; D047250:Calixarenes
keywords: click chemistry; cycloadditions; glycoconjugates; ligand effects; medicinal chemistry