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Sulfonation of papain-treated chitosan and its mechanism for anticoagulant activity |
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| Authors: | Jiraporn Suwan Boyangzi Li Puttinan Meepowpan Shaker A Mousa Bhusana Premanode Robert J Linhardt |
| Institution: | a Thailand Excellence Center for Tissue Engineering, Department of Biochemistry, Faculty of Medicine, Chiang Mai University, Chiang Mai 50200, Thailand b Division of Transfusion Science, Department of Medical Technology, Faculty of Associated Medical Sciences, Chiang Mai University, Chiang Mai 50200, Thailand c Department of Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai 50200, Thailand d Department of Chemistry and Chemical Biology, Center for Biotechnology and Interdisciplinary Studies, Rensselaer Polytechnic Institute, 110, 8th Street, Troy, NY 12180, USA e Department of Chemical and Biological Engineering, Center for Biotechnology and Interdisciplinary Studies, Rensselaer Polytechnic Institute, 110, 8th Street, Troy, NY 12180, USA f Department of Biology, Center for Biotechnology and Interdisciplinary Studies, Rensselaer Polytechnic Institute, 110, 8th Street, Troy, NY 12180, USA g Institute of Biomedical Engineering, Imperial College, Sherfield Building Suite 5, South Kensington, London SW7 2AZ, United Kingdom h Pharmaceutical Research Institute, Albany College of Pharmacy, 1 Discovery Drive, Rensselaer, NY 12144, USA |
| Abstract: | The novel low-molecular-weight chitosan polysulfate (MW 5120-26,200 Da) was prepared using the depolymerization of chitosan with papain (EC. 3.4.22.2). The sulfonation of depolymerized products was performed using chlorosulfonic acid in N,N-dimethylformamide under semi-heterogeneous conditions. The structures of the products were characterized by FTIR, 13C NMR, and 1H NMR (1D, 2D NMR) spectroscopy. The present study sheds light on the mechanism of anticoagulant activity of chitosan polysulfate. Anticoagulant activity was investigated by an activated partial thromboplastin assay, a thrombin time assay, a prothrombin time assay, and thrombelastography. Surface plasmon resonance also provided valuable data for understanding the relationship between the molecular binding of sulfated chitosan to two important blood clotting regulators, antithrombin III and heparin cofactor II. These results show that the principal mechanism by which this chitosan polysulfate exhibits anticoagulant activity is mediated through heparin cofactor II and is dependent on polysaccharide molecular weight. |
| Keywords: | Chitin Chitosan polysulfate Sulfonation Anticoagulant activity |
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