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

Nicolas Galanos, Emilie Gillon, Anne Imberty, Susan Matthews, Sebastien Vidal

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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.
Original languageEnglish
Pages (from-to)3476-3481
Number of pages6
JournalOrganic & Biomolecular Chemistry
Early online date8 Mar 2016
Publication statusPublished - 7 Apr 2016

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