Pentavalent pillar[5]arene-based glycoclusters and their multivalent binding to pathogenic bacterial lectins

Galanos, Nicolas, Gillon, Emilie, Imberty, Anne, Matthews, Susan ORCID: https://orcid.org/0000-0001-8821-0851 and Vidal, Sebastien (2016) Pentavalent pillar[5]arene-based glycoclusters and their multivalent binding to pathogenic bacterial lectins. Organic & Biomolecular Chemistry, 14. pp. 3476-3481. ISSN 1477-0520

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Abstract

Anti-adhesive glycoclusters offer potential as therapeutic alternatives to classical antibiotics in treating infections. Pillar[5]arenes functionalised with either five galactose or five fucose residues were readily prepared using CuAAC reactions and evaluated for their binding to three therapeutically relevant bacterial lectins: LecA and Lec B from Pseudomonas aeuruginosa and BambL from Burkholderia ambifaria. Steric interactions were demonstrated to be a key factor in achieving good binding to LecA with more flexible galactose glycoclusters showing enhanced activity. In contrast binding to the fucose-selective lectins confirmed the importance of topology of the glycoclusters for activity with the pillar[5]arene ligand proving a selective ligand for BambL.

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:	01 Apr 2016 10:14
Last Modified:	04 May 2024 01:31
URI:	https://ueaeprints.uea.ac.uk/id/eprint/58043
DOI:	10.1039/C6OB00220J

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