title: Synthesis and antifungal properties of sulfanilamide derivatives of chitosan.
abstract: Sulfanilamide derivatives of chitosan (2-(4-acetamido-2-sulfanimide)-chitosan (HSACS, LSACS), 2-(4-acetamido-2-sulfanimide)-6-sulfo-chitosan (HSACSS, LSACSS) and 2-(4-acetamido-2-sulfanimide)-6-carboxymethyl-chitosan (HSACMCS, LSACMCS)) were prepared using different molecular weights of chitosan (CS), carboxymethyl chitosan (CMCS) and chitosan sulfates (CSS) reacted with 4-acetamidobenzene sulfonyl chloride in dimethylsulfoxide solution. The structures of the derivatives were characterized by FT-IR spectroscopy and elemental analysis, which showed that the substitution degree of sulfanilamide group of HSACS, HSACSS, HSACMCS, LSACS, LSACSS and LSACMCS were 0.623, 0.492, 0.515, 0.576, 0.463 and 0.477, respectively. The solubility of the derivatives (pH<7.5) was higher than that of chitosan (pH<6.5). The antifungal activities of the derivatives against Aiternaria solani and Phomopsis asparagi were evaluated based on the method of Jasso et al. in the experiment. The results indicated that all the prepared sulfanilamide derivatives had a significant inhibiting effect on the investigated fungi in the polymer concentration range from 50 to 500 microg mL(-1). The antifungal activities of the derivatives increased with increasing the molecular weight, concentration or the substitution degree. The sulfanilamide derivatives of CS, CMCS and CSS show stronger antifungal activities than CS, CMCS and CSS.
authors.affiliation: Institute of Oceanology, Chinese Academy of Sciences, Qingdao 266071, China.
authors.forename: Zhimei
authors.initials: Z
authors.lastname: Zhong
authors.forename: Rong
authors.initials: R
authors.lastname: Chen
authors.forename: Ronge
authors.initials: R
authors.lastname: Xing
authors.forename: Xiaolin
authors.initials: X
authors.lastname: Chen
authors.forename: Song
authors.initials: S
authors.lastname: Liu
authors.forename: Zhanyong
authors.initials: Z
authors.lastname: Guo
authors.forename: Xia
authors.initials: X
authors.lastname: Ji
authors.forename: Lin
authors.initials: L
authors.lastname: Wang
authors.forename: Pengcheng
authors.initials: P
authors.lastname: Li
mesh_terms: D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001203:Ascomycota / Q000187:drug effects; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D048271:Chitosan / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D015394:Molecular Structure; D017550:Spectroscopy, Fourier Transform Infrared; D000077145:Sulfanilamide; D013424:Sulfanilamides / Q000737:chemistry*
chemical_list: D000935:Antifungal Agents; D013424:Sulfanilamides; D000077145:Sulfanilamide; D048271:Chitosan