Synthesis of cyclodextrin derivatives with monosacharides and their binding with ampicillin and selected lectins

Abstract

β- and γ-Cyclodextrins connected on their narrow side via 6 bond-linkers with monosaccharides (Man, GlcNAc) suitable for bacterial lectin recognition, along with reference mono-analogues were prepared. The resulting compounds: (a) posses a functional cavity forming inclusion complexes with a model guest molecule and with the antibiotic ampicillin; (b) inhibit by more than 30% the hydrolysis of ampicillin in the presence of the enzyme β-lactamase; (c) interact stronger with surface immobilized lectins than the reference mono-analogues. The present work suggests that combining the lectin recognition property of the compounds with their ability to encapsulate antibiotics could be used to target and kill bacteria.