title: Selective carboxypropionylation of chitosan: synthesis, characterization, blood compatibility, and degradation.
abstract: Two water-soluble chitosan (WSC) derivatives of N-succinyl-chitosan (NSCS) and N,O-succinyl-chitosan (NOSCS) with a degree of substitution (DS) that ranged form 0.28 to 0.61 were selectively synthesized by varying the molar ration of succinic anhydride and chitosan. The chemical structure and physical properties of the chitosan derivatives were characterized by FT-IR, 1H NMR, and XRD. XRD analysis showed that the derivatives were amorphous. The lysozyme enzymatic degradation results revealed that the NSCS was of higher susceptibility to lysozyme. The degradation rate and the solubility of the chitosan derivatives were strongly determined by the degree of substitution and the position of the substitution. The results of antithrombotic properties, hemolytic properties and anticoagulant properties of WSCs indicated that the blood compatibility was dramatically improved, and the carboxyl group introduced on the C-6 or C-2 hydroxyl group appeared to impact anticoagulant activity in different ways.
authors.affiliation: College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, Chaowang Road 18, 310014, PR China.
authors.forename: Wen-yue
authors.initials: WY
authors.lastname: Xiong
authors.forename: Yu
authors.initials: Y
authors.lastname: Yi
authors.forename: Hua-zhang
authors.initials: HZ
authors.lastname: Liu
authors.forename: Hong
authors.initials: H
authors.lastname: Wang
authors.forename: Jin-hua
authors.initials: JH
authors.lastname: Liu
authors.forename: Guo-qing
authors.initials: GQ
authors.lastname: Ying
mesh_terms: D000818:Animals; D000925:Anticoagulants / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001777:Blood Coagulation / Q000187:drug effects*; D002264:Carboxylic Acids / Q000737:chemistry*; D048271:Chitosan / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D006461:Hemolysis / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D011422:Propionates / Q000737:chemistry*; D011817:Rabbits; D012995:Solubility; D017550:Spectroscopy, Fourier Transform Infrared; D014867:Water / Q000737:chemistry; D014961:X-Ray Diffraction
chemical_list: D000925:Anticoagulants; D002264:Carboxylic Acids; C118639:N-succinyl-chitosan; D011422:Propionates; D014867:Water; D048271:Chitosan