Preparation of imidazole acids grafted chitosan with enhanced antioxidant, antibacterial and antitumor activities

Abstract

Herein, imidazole acids grafted chitosan derivatives were synthesized, including HACC, HACC derivatives, TMC, TMC derivatives, amidated chitosan and amidated chitosan bearing imidazolium salts. The prepared chitosan derivatives were characterized by FT-IR and 1H NMR. The tests evaluated the biological antioxidant, antibacterial, and cytotoxic activities of chitosan derivatives. The antioxidant capacity (DPPH radical, superoxide anion radical and hydroxyl radical) of chitosan derivatives was 2.4–8.3 times higher than that of chitosan. The antibacterial capacity against E. coli and S. aureus of cationic derivatives (HACC derivatives, TMC derivatives, and amidated chitosan bearing imidazolium salts) was more active than only imidazole-chitosan (amidated chitosan). In particular, the inhibition effect of HACC derivatives on E. coli was 15.625 μg/mL. Moreover, the series of chitosan derivatives bearing imidazole acids showed certain activity against MCF-7 and A549 cells. The present results suggest that the chitosan derivatives in this paper seem to be promising carrier materials for use in drug delivery systems.