Synthesis and Antibacterial Activity of Hybrid Supramolecular Complexes Based on Tetracycline/Doxycycline and Water-Soluble C60-Fullerene Derivatives

Abstract

Water-soluble pentasubstituted anionic and cationic C₆₀-fullerene derivatives were synthesized in highly selective reactions of chlorofullerene C₆₀Cl₆ with captopril and an aliphatic amine. Hybrid supramolecular complexes of the functionalized C₆₀-fullerene derivatives and tetracycline antibiotics (in a stoichiometric 1:1 mole ratio) with polymodal hydrodynamic-radius distributions were synthesized in aqueous solution as nano-sized micelles and vesicles. Hybrid complexes of the antibiotics and cationic amino-C₆₀-fullerene derivatives exhibited synergic antibacterial effects that were more pronounced against a tetracycline-resistant Escherichia coli strain (carrier of the Tc^R gene).