Preparation, characterization and anticoagulant activity in vitro of heparin-like 6-carboxylchitin derivative

A series of heparin-like 6-carboxylchitin derivatives with different N-acetyl group and sulfate group contents were prepared. Their structures were characterized by element analysis, FT-IR, 13C NMR, and gel permeation chromatography. Their anticoagulant activity in vitro was investigated for human plasma with respect to activated partial thromboplastin time (APTT). The results showed all 6-carboxylchitin derivatives prolonged APTT within the scope of studied degree of sulfation (0.28–1.03) and Mws (4.3–13.7 kDa). Their anticoagulant activity strongly depended on their structures. 3,6-O-sulfated group promoted the anticoagulant activity. Only incorporation of N-sulfated group into deacetylated 6-carboxylchitin could not improve the anticoagulant activity. But, N-sulfated group and O-sulfated group had the synergistic action, and N-sulfated group could promote the anticoagulant activity for the N,O-sulfated chitin derivatives. In addition, acetyl group took a role in the anticoagulant activity, too.

► Heparin-like 6-carboxylchitin derivatives were prepared via oxidation and sulfation. ► They could inhibit the intrinsic coagulant pathway. ► N-sulfonate groups could not improve the activity for only N-sulfonated derivatives. ► N-sulfonate groups could promote the activity for O-sulfated chitin derivatives. ► Acetyl groups took a role in the anticoagulant activity.