Anticoagulant activity of a sulfated chitosan.
Chitin prepared from the shells of rice-field crabs (Somanniathelphusa dugasti) was converted into chitosan with a degree of acetylation of 0.21 and then sulfated with chlorosulfonic acid in N,N-dimethylformamide under semi-heterogeneous conditions to give 87% of water-soluble sulfated chitosan with degree of substitution (d.s) of 2.13. 1H NMR revealed the sulfate substitution at C-2, C-3 and C-6. Gel filtration on Sepharose CL-6B of the sulfated chitosan gave three fractions with average molecular weights of 7.1, 3.5, and 1.9 x 10(4). The three sulfated chitosan preparations showed strong anticoagulant activities, with the same mechanism of action observed for standard therapeutic heparin.
Vongchan
Preeyanat
P
Department of Biochemistry, Faculty of Medicine, Chiang Mai University, Chiang Mai, 50200, Thailand. pvongchan@hotmail.com
Sajomsang
Warayuth
W
Subyen
Dumrat
D
Kongtawelert
Prachya
P
D000107:Acetylation; D000818:Animals; D000925:Anticoagulants / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D001777:Blood Coagulation / Q000187:drug effects; D002686:Chitin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D048271:Chitosan; D002850:Chromatography, Gel; D006493:Heparin / Q000494:pharmacology; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013431:Sulfates / Q000737:chemistry*; D013451:Sulfonic Acids / Q000737:chemistry; D013917:Thrombin / Q000037:antagonists & inhibitors
D000925:Anticoagulants; D013431:Sulfates; D013451:Sulfonic Acids; D002686:Chitin; C013880:chlorosulfonic acid; D006493:Heparin; D048271:Chitosan; D013917:Thrombin