Issue 13, 2016

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

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
27 Jan 2016
Accepted
04 Mar 2016
First published
08 Mar 2016

Org. Biomol. Chem., 2016,14, 3476-3481

Author version available

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

N. Galanos, E. Gillon, A. Imberty, S. E. Matthews and S. Vidal, Org. Biomol. Chem., 2016, 14, 3476 DOI: 10.1039/C6OB00220J

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