Pillar[5]arene-based glycoclusters: synthesis and multivalent binding to pathogenic bacterial lectins

Buffet, Kevin, Nierengarten, Iwona, Galanos, Nicolas, Gillon, Emilie, Holler, Michel, Imberty, Anne, Matthews, Susan E., Vidal, Sébastien, Vincent, Stéphane P. and Nierengarten, Jean-François (2016) Pillar[5]arene-based glycoclusters: synthesis and multivalent binding to pathogenic bacterial lectins. Chemistry - A European Journal, 22 (9). pp. 2955-2963. ISSN 0947-6539

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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 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.

Item Type:	Article
Faculty \ School:	Faculty of Science > School of Pharmacy (former - to 2024) Faculty of Science > School of Natural Sciences (former - to 2024)
UEA Research Groups:	Faculty of Science > Research Groups > Medicinal Chemistry (former - to 2017) Faculty of Science > Research Groups > Chemical Biology and Medicinal Chemistry (former - to 2021)
Depositing User:	Pure Connector
Date Deposited:	18 Feb 2016 17:00
Last Modified:	06 Feb 2025 06:12
URI:	https://ueaeprints.uea.ac.uk/id/eprint/57196
DOI:	10.1002/chem.201504921

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