Synthesis, Characterization, and the Antioxidant Activity of Carboxymethyl Chitosan Derivatives Containing Thiourea Salts

Abstract

A new class of chitosan derivatives possessing thiourea salts were synthesized to improve the solubility and the antioxidant activity of chitosan. Firstly, chitosan was modified to carboxymethyl chitosan, combining carboxymethyl chitosan with thiourea salts that have different structures to form new chitosan derivatives. The chitosan and chitosan derivatives were characterized by FT-IR, 13C NMR, TGA, and elemental analyses. The new peaks of thiourea salts could be clearly observed at about 1240 cm–1 in the IR spectra, and the peak of C=S was clearly observed at around 180 ppm in the 13C NMR. IR spectra and 13C NMR of the structural units of these polymers validated the chitosan derivatives possessing thiourea salts were successfully synthesized. Their antioxidant properties were tested, including DPPH-radical scavenging ability, superoxide-radical scavenging ability, and hydroxyl-radical scavenging ability. Our results suggested the increase of thiourea salt groups in chitosan derivatives promotes the scavenging effect. The scavenging activity of 4TMCMCS, TMCMCS. 4,4DCMCS, and 4ACMCS against DPPH-radical and superoxide-radical were more than 90% at 1.6 mg/mL, respectively. In the cytotoxicity assay, no cytotoxicity was observed for the L929 cells with chitosan and its derivatives at all testing concentrations. These results demonstrated that the combination of chitosan and thiourea salt groups improved the antioxidant activity of chitosan, and the antioxidants or free radical scavengers based on natural polymers and thiourea salts showed potential applications.