Pentavalent pillar[5]arene-based glycoclusters and their multivalent binding to pathogenic bacterial lectins. Issue 13 (14th March 2016)

• Record Type: Journal Article
• Authors: Galanos, Nicolas; Gillon, Emilie; Imberty, Anne; Matthews, Susan E.; Vidal, Sébastien
• Is Part Of: Organic & biomolecular chemistry. Volume 14:Issue 13(2016)
• Page Start: 3476
• Page End: 3481
• Publication Date: 2016-03-14
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c6ob00220j
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Anti-adhesive glycoclusters offer potential as therapeutic alternatives to classical antibiotics in treating infections. 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.