To improve the solubility and bioactivity of chitosan,a new class of carboxymethyl chitosan derivatives possessing sulfonium salts was successfully designed and synthesized,including Methyl sulfi de carboxymethyl chit...To improve the solubility and bioactivity of chitosan,a new class of carboxymethyl chitosan derivatives possessing sulfonium salts was successfully designed and synthesized,including Methyl sulfi de carboxymethyl chitosan(MCMCS),Ethyl sulfi de carboxymethyl chitosan(ECMCS),Propyl sulfi de carboxymethyl chitosan(PCMCS),and Butyl sulfi de carboxymethyl chitosan(BCMCS).To determine the structure of the new class of the derivatives,methods of the Fourier transform infrared spectroscopy(FT-IR),^(1)H nuclear magnetic resonance spectrometer(^(1)H NMR),and^(13)C nuclear magnetic resonance spectrometer(^(13)C NMR)were used.Moreover,the antioxidant activity of the derivatives for three types of free radicals,i.e.,hydroxyl radical,superoxide radical,and 1,1-diphenyl-2-picrylhydrazyl(DPPH)radical was evaluated in vitro.In addition,the L929 cells were adopted to test the cytotoxicity of chitosan and its derivatives by CCK-8 assay.The class of the carboxymethyl chitosan derivatives showed a strong scavenging ability against the three free radicals at 1.6 mg/mL,with scavenging rate of over 70%and some up to 100%.At this high rate,the overall cell viability in the toxicity test reached more than 80%,indicating that the synthetic derivative had a little cytotoxicity.The results show that the introduction of carboxymethyl group to chitosan increased the water-solubility of chitosan,and the combination of sulfonate ions with diff erent chain lengths further enhanced the antioxidant activity of chitosan.Therefore,the sulfonium-containing carboxymethyl chitosan derivatives had excellent bioactivity with good application prospects in food,biomedicine,and medical fi elds.展开更多
基金Supported by the National Key R&D Program of China(No.2019YFD0900705)the Key Deployment Projects of the Marine Science Research Center of the Chinese Academy of Sciences(No.COMS2020J04)the Natural Science Foundation of Shandong Province of China(No.ZR2019BD064)。
文摘To improve the solubility and bioactivity of chitosan,a new class of carboxymethyl chitosan derivatives possessing sulfonium salts was successfully designed and synthesized,including Methyl sulfi de carboxymethyl chitosan(MCMCS),Ethyl sulfi de carboxymethyl chitosan(ECMCS),Propyl sulfi de carboxymethyl chitosan(PCMCS),and Butyl sulfi de carboxymethyl chitosan(BCMCS).To determine the structure of the new class of the derivatives,methods of the Fourier transform infrared spectroscopy(FT-IR),^(1)H nuclear magnetic resonance spectrometer(^(1)H NMR),and^(13)C nuclear magnetic resonance spectrometer(^(13)C NMR)were used.Moreover,the antioxidant activity of the derivatives for three types of free radicals,i.e.,hydroxyl radical,superoxide radical,and 1,1-diphenyl-2-picrylhydrazyl(DPPH)radical was evaluated in vitro.In addition,the L929 cells were adopted to test the cytotoxicity of chitosan and its derivatives by CCK-8 assay.The class of the carboxymethyl chitosan derivatives showed a strong scavenging ability against the three free radicals at 1.6 mg/mL,with scavenging rate of over 70%and some up to 100%.At this high rate,the overall cell viability in the toxicity test reached more than 80%,indicating that the synthetic derivative had a little cytotoxicity.The results show that the introduction of carboxymethyl group to chitosan increased the water-solubility of chitosan,and the combination of sulfonate ions with diff erent chain lengths further enhanced the antioxidant activity of chitosan.Therefore,the sulfonium-containing carboxymethyl chitosan derivatives had excellent bioactivity with good application prospects in food,biomedicine,and medical fi elds.
