title: Enhanced water-solubility and antibacterial activity of novel chitosan derivatives modified with quaternary phosphonium salt.
abstract: Chitosan (CS) has been widely recognized as an important biomaterial due to its good antimicrobial activity, biocompatibility and biodegradability. However, CS is insoluble in water in neutral and alkaline aqueous solution due to the linear aggregation of chain molecules and the formation of crystallinity. This is one of the key factors that limit its practical applications. Therefore, improving the solubility of CS in neutral and alkaline aqueous solution is a primary research direction for biomedical applications. In this paper, a reactive antibacterial compound (4-(2,5-Dioxo-pyrrolidin-1-yloxycarbonyl)-benzyl)-triphenyl-phosphonium bromide (NHS-QPS) was synthesized for chemical modification of CS, and a series of novel polymeric antimicrobial agents, N-quaternary phosphonium chitosan derivatives (N-QPCSxy, x=1-2,y=1-4) were obtained. The water solubilities and antibacterial activities of N-QPCSxy against Escherichia coli and Staphylococcus aureus were evaluated compare to CS. The water solubility of N-QPCSxy was all better than that of CS at neutral pH aqueous solution, particularly, N-QPCS14 can be soluble in water over the pH range of 3 to 12. The antibacterial activities of CS derivatives were improved by introducing quaternary phosphonium salt, and antibacterial activity of N-QPCSxy increases with degree of substitution. Overall, N-QPCS14 represents a novel antibacterial polymer material with good antibacterial activity, waters solubility and low cytotoxicity.
authors.affiliation: Nanshan District Key Lab for Biopolymers and Safety Evaluation, College of Materials Science and Engineering, Shenzhen University, Shenzhen 518060, PR China.
authors.forename: Dan
authors.initials: D
authors.lastname: Zhu
authors.affiliation: Nanshan District Key Lab for Biopolymers and Safety Evaluation, College of Materials Science and Engineering, Shenzhen University, Shenzhen 518060, PR China.
authors.forename: Honghao
authors.initials: H
authors.lastname: Cheng
authors.affiliation: Shenzhen University Health Science Center, Shenzhen 518060, PR China.
authors.forename: Jianna
authors.initials: J
authors.lastname: Li
authors.affiliation: North Carolina State University, Raleigh, NC 27695, USA.
authors.forename: Wenwen
authors.initials: W
authors.lastname: Zhang
authors.affiliation: Shenzhen University Health Science Center, Shenzhen 518060, PR China.
authors.forename: Yuanyuan
authors.initials: Y
authors.lastname: Shen
authors.affiliation: Nanshan District Key Lab for Biopolymers and Safety Evaluation, College of Materials Science and Engineering, Shenzhen University, Shenzhen 518060, PR China.
authors.forename: Shaojun
authors.initials: S
authors.lastname: Chen
authors.affiliation: Nanshan District Key Lab for Biopolymers and Safety Evaluation, College of Materials Science and Engineering, Shenzhen University, Shenzhen 518060, PR China.
authors.forename: Zaochuan
authors.initials: Z
authors.lastname: Ge
authors.affiliation: Nanshan District Key Lab for Biopolymers and Safety Evaluation, College of Materials Science and Engineering, Shenzhen University, Shenzhen 518060, PR China. Electronic address: csg@szu.edu.cn.
authors.forename: Shiguo
authors.initials: S
authors.lastname: Chen
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000494:pharmacology; D048271:Chitosan / Q000737:chemistry / Q000494:pharmacology; D004926:Escherichia coli / Q000254:growth & development*; D009943:Organophosphorus Compounds / Q000737:chemistry / Q000494:pharmacology; D012995:Solubility; D013211:Staphylococcus aureus / Q000254:growth & development*
chemical_list: D000900:Anti-Bacterial Agents; D009943:Organophosphorus Compounds; D048271:Chitosan
keywords: Antibacterial; Chitosan; Quaternary phosphonium; Water solubility