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

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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 in order 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 - A European Journal
Issue number9
Early online date4 Feb 2016
Publication statusPublished - 24 Feb 2016

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