title: Preparation, characterization and antibacterial activity of O-acetyl-chitosan-N-2-hydroxypropyl trimethyl ammonium chloride.
abstract: Chitosan-N-2-hydroxypropyl trimethyl ammonium chloride (QTS) was prepared by reaction of chitosan (CS) and glycidyl trimethylammonium chloride. Later, O-acetyl-chitosan-N-2-hydroxypropyl trimethyl ammonium chloride (AQTS) was synthesized by reaction of QTS with acetic acid in the presence of SOCl2. Both derivatives were characterized by FTIR, (1)H NMR, TGA, and XRD techniques. The degree of quaternization of QTS was 85.5%, and the degree of acetyl (DA) of AQTS was from 1.63 to 2.31. Compared with CS, the solubility of QTS and AQTS was improved at different levels, especially AQTS, it could be dissolved in many organic solvents, water, and aqueous solution. Notably, the solubility of AQTS in organic solvents increased as DA increased, while the solubility in water was reversed. The results of CS, QTS, and AQTS against Escherichia coli and Staphylococcus aureus showed that QTS and AQTS exhibited higher antibacterial activity than CS, and the antibacterial activity of AQTS decreased with increased DA. Moreover, the inhibition effect was AQTS1 (DA 1.63)>AQTS2 (DA 2.02)>QTS>AQTS3 (DA 2.31). On the basis of the results of the present study, it could be emphasized that hydrophobicity and positive charge density might strongly affect the antibacterial activity of quaternary ammonium chitosan derivatives.
authors.affiliation: College of Marine Life Science, Ocean University of China, 5 Yushan Road, Qingdao 266003, PR China.
authors.forename: Jinping
authors.initials: J
authors.lastname: Cai
authors.affiliation: College of Marine Life Science, Ocean University of China, 5 Yushan Road, Qingdao 266003, PR China.
authors.forename: Qifeng
authors.initials: Q
authors.lastname: Dang
authors.affiliation: College of Marine Life Science, Ocean University of China, 5 Yushan Road, Qingdao 266003, PR China. Electronic address: liucsouc@126.com.
authors.forename: Chengsheng
authors.initials: C
authors.lastname: Liu
authors.affiliation: College of Marine Life Science, Ocean University of China, 5 Yushan Road, Qingdao 266003, PR China.
authors.forename: Teng
authors.initials: T
authors.lastname: Wang
authors.affiliation: Qingdao Aorun Biotechnology Co. Ltd., Room 602, Century Mansion, 39 Donghaixi Road, Qingdao 266071, PR China.
authors.forename: Bing
authors.initials: B
authors.lastname: Fan
authors.affiliation: School of Medicine and Pharmacy, Ocean University of China, 5 Yushan Road, Qingdao 266003, PR China.
authors.forename: Jingquan
authors.initials: J
authors.lastname: Yan
authors.affiliation: College of Marine Life Science, Ocean University of China, 5 Yushan Road, Qingdao 266003, PR China.
authors.forename: Yanyan
authors.initials: Y
authors.lastname: Xu
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D048271:Chitosan / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D004926:Escherichia coli / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D000644:Quaternary Ammonium Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D012995:Solubility; D017550:Spectroscopy, Fourier Transform Infrared; D013211:Staphylococcus aureus / Q000187:drug effects
chemical_list: D000900:Anti-Bacterial Agents; C000608258:O-acetylchitosan-N-2-hydroxypropyl trimethyl ammonium; D000644:Quaternary Ammonium Compounds; D048271:Chitosan
keywords: Antibacterial activity; Characterization; O-acetyl-chitosan-N-2-hydroxypropyl trimethyl ammonium chloride; Solubility