Pillar[5]arene-Based Glycoclusters: Synthesis and Multivalent Binding to Pathogenic Bacterial Lectins

Kevin Buffet, Iwona Nierengarten, Nicolas Galanos, Emilie Gillon, Michel Holler, Anne Imberty, Susan E. Matthews, Sébastien Vidal, Stéphane P. Vincent, Jean François Nierengarten

Research output: Contribution to journalArticle

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.

Original languageEnglish
Pages (from-to)2955-2963
Number of pages9
JournalChemistry (Weinheim an der Bergstrasse, Germany)
Volume22
Issue number9
DOIs
Publication statusPublished - 24 Feb 2016

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Keywords

  • click chemistry
  • cycloadditions
  • glycoconjugates
  • ligand effects
  • medicinal chemistry

Cite this

Buffet, K., Nierengarten, I., Galanos, N., Gillon, E., Holler, M., Imberty, A., Matthews, S. E., Vidal, S., Vincent, S. P., & Nierengarten, J. F. (2016). Pillar[5]arene-Based Glycoclusters: Synthesis and Multivalent Binding to Pathogenic Bacterial Lectins. Chemistry (Weinheim an der Bergstrasse, Germany), 22(9), 2955-2963. https://doi.org/10.1002/chem.201504921