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. ORCID: https://orcid.org/0000-0001-8821-0851, 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

Microsoft Word (SweetPillarCEJRevised) - Accepted Version Download (3MB)

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 Faculty of Science > School of Natural Sciences
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:	04 May 2024 01:28
URI:	https://ueaeprints.uea.ac.uk/id/eprint/57196
DOI:	10.1002/chem.201504921

Downloads

Actions (login required)

View Item