Synthesis of N-succinyl- and N-glutaryl-chitosan derivatives and their antioxidant, antiplatelet, and anticoagulant activity

• Published in: Carbohydrate polymers 2017-06, Vol.166, p.166-172
• Main Authors: Skorik, Yury A., Kritchenkov, Andreii S., Moskalenko, Yulia E., Golyshev, Anton A., Raik, Sergei V., Whaley, Andrei K., Vasina, Lyubov V., Sonin, Dmitry L.
• Format: Article
• Language: English
• Subjects: Adult; Anticoagulant activity; Anticoagulants - pharmacology; Antioxidant activity; Antioxidants - pharmacology; Antiplatelet activity; Chitosan - chemical synthesis; Female; Glutaryl-chitosan; Humans; Magnetic Resonance Spectroscopy; Male; Platelet Aggregation Inhibitors - pharmacology; Succinyl-chitosan; Temperature
• ISSN: 0144-8617; 1879-1344
• DOI: 10.1016/j.carbpol.2017.02.097

•Succinyl-chitosan (SC) and glutaryl-chitosan (GC) were prepared and characterized.•Protocols were developed for synthesis of SC and GC with specific degree of substitution.•SC and GC showed pronounced antioxidant, antiplatelet and anticoagulant activity. The effects of temperature, reactant ratio, pH, and reaction time were studied on the polymers formed by the reactions of succinic and glutaric anhydrides with chitosan under both homogeneous and heterogeneous conditions. As a result, protocols were developed for the synthesis of succinyl- and glutaryl-chitosan derivatives (SC and GC, respectively) with a specific degree of substitution. The polymers were characterized by NMR spectroscopy, including two-dimensional NMR techniques, that confirms N-substitution of chitosan under reaction conditions used. SC and GC both show pronounced and similar antioxidant activity, which slightly increases with an increase in the degree of substitution. Both SC and GC showed antiplatelet and anticoagulant activity. The platelet aggregation is suppressed more strongly in the experiments with GC than with SC, although the latter exhibits a more pronounced anticoagulant activity.