The antioxidant activity of 2-(4(or 2)-hydroxyl-5-chloride-1,3-benzene-di-sulfanimide)-chitosan.
Chitosan (CS) with two different molecular weights was modified by reacting with 4-hydroxyl-5-chloride-1,3-benzene-disulfo-chloride or 2-hydroxyl-5-chloride-1,3-benzene-disulfo-chloride to give new 2-(4(or 2)-hydroxyl-5-chloride-1,3-benzene-di-sulfanimide)-chitosan (2-HCBSAHCS, 2-HCBSALCS, 4-HCBSAHCS, 4-HCBSALCS). The structure of the derivatives was characterized by FT-IR and 13C NMR spectroscopy. The antioxidant activities of the derivatives were investigated employing various established systems, such as hydroxyl radical (.OH)/superoxide anion (O2.-) scavenging/reducing power and chelating activity. All the derivatives showed stronger scavenging activity on hydroxyl radical than chitosan and ascorbic acid (Vc), and IC50 of 4-HCBSAHCS, 4-HCBSALCS, 2-HCBSAHCS and 2-HCBSALCS was 0.334, 0.302, 0.442, 0.346 mg/mL, respectively. The inhibitory activities of the derivatives toward superoxide radical by the PMS-NADH system were strong. The results showed that the superoxide radical scavenging effect of 2-(4(or 2)-hydroxyl-5-chloride-1,3-benzene-di-sulfanimide)-chitosan was higher than chitosan. The derivatives had obviously reducing power and slight chelating activity. The data obtained in in vitro models clearly establish the antioxidant potency of 2-(4(or 2)-hydroxyl-5-chloride-1,3-benzene-disulfanimide)-chitosan.
Institute of Oceanology, The Chinese Academy of Sciences, Qingdao 266071, China. zhimeihappy@126.com
Zhimei
Z
Zhong
Ronge
R
Xing
Song
S
Liu
Lin
L
Wang
Shengbao
S
Cai
Pengcheng
P
Li
D002614:Chelating Agents / Q000737:chemistry / Q000494:pharmacology; D048271:Chitosan / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology*; D016166:Free Radical Scavengers / Q000737:chemistry / Q000494:pharmacology*; D017665:Hydroxyl Radical / Q000378:metabolism; D010084:Oxidation-Reduction; D013449:Sulfonamides / Q000737:chemistry / Q000494:pharmacology*; D013481:Superoxides / Q000378:metabolism
C534061:2-(2-hydroxy-5-chloro-1,3-benzenedisulfonamide)chitosan; C534060:2-(4-hydroxy-5-chloro-1,3-benzenedisulfonamide)chitosan; D002614:Chelating Agents; D016166:Free Radical Scavengers; D013449:Sulfonamides; D013481:Superoxides; D017665:Hydroxyl Radical; D048271:Chitosan