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.
Department of Biochemistry, Faculty of Medicine, Chiang Mai University, Chiang Mai, 50200, Thailand. pvongchan@hotmail.com
Preeyanat
P
Vongchan
Warayuth
W
Sajomsang
Dumrat
D
Subyen
Prachya
P
Kongtawelert
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