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

Nicolas Galanos (1) , Emilie Gillon (2) , Anne Imberty (2) , Susan Matthews , Sébastien Vidal (1)

1 CO2GLYCO - Chimie Organique 2-Glycochimie
2 CERMAV - Centre de Recherches sur les Macromolécules Végétales

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.

Domains: Chemical Sciences; Organic chemistry

Nicolas Galanos, Emilie Gillon, Anne Imberty, Susan Matthews, Sébastien Vidal. Pentavalent pillar[5]arene-based glycoclusters and their multivalent binding to pathogenic bacterial lectins. Organic & Biomolecular Chemistry, 2016, 14 (13), pp.3476-3481. ⟨10.1039/C6OB00220J⟩. ⟨hal-02123866⟩