title: Enhanced water-solubility, antibacterial activity and biocompatibility upon introducing sulfobetaine and quaternary ammonium to chitosan.
abstract: Chitosan (CS) has attracted much attention due to its good antibacterial activity and biocompatibility. However, CS is insoluble in neutral and alkaline aqueous solution, limiting its biomedical application to some extent. To circumvent this drawback, we have synthesized a novel N-quaternary ammonium-O-sulfobetaine-chitosan (Q3BCS) by introducing quaternary ammonium compound (QAC) and sulfobetaine, and its water-solubility, antibacterial activity and biocompatibility were evaluated compare to N-quaternary ammonium chitosan and native CS. The results showed that by introducing QAC, antibacterial activities and water-solubilities increase with degrees of substitution. The largest diameter zone of inhibition (DIZ) was improved from 0 (CS) to 15mm (N-Q3CS). And the water solution became completely transparent from pH 6.5 to pH 11; the maximal waters-solubility was improved from almost 0% (CS) to 113% at pH 7 (N-Q3CS). More importantly, by further introducing sulfobetaine, cell survival rate of Q3BCS increased from 30% (N-Q3CS) to 85% at 2000μg/ml, which is even greater than that of native CS. Furthermore, hemolysis of Q3BCS was dropped sharply from 4.07% (N-Q3CS) to 0.06%, while the water-solution and antibacterial activity were further improved significantly. This work proposes an efficient strategy to prepare CS derivatives with enhanced antibacterial activity, biocompatibility and water-solubility. Additionally, these properties can be finely tailored by changing the feed ratio of CS, glycidyl trimethylammonium chloride and NCO-sulfobetaine.
authors.affiliation: Nanshan District Key Lab for Biopolymers and Safety Evaluation, Shenzhen Key Laboratory of Polymer Science and Technology, Guangdong Research Center for Interfacial Engineering of Functional Materials, College of Materials Science and Engineering, Shenzhen University, Shenzhen 518060, PR China.
authors.forename: Yuxiang
authors.initials: Y
authors.lastname: Chen
authors.affiliation: Shenzhen University Health Science Center, Shenzhen 518060, PR China.
authors.forename: Jianna
authors.initials: J
authors.lastname: Li
authors.affiliation: Nanshan District Key Lab for Biopolymers and Safety Evaluation, Shenzhen Key Laboratory of Polymer Science and Technology, Guangdong Research Center for Interfacial Engineering of Functional Materials, College of Materials Science and Engineering, Shenzhen University, Shenzhen 518060, PR China.
authors.forename: Qingqing
authors.initials: Q
authors.lastname: Li
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, Shenzhen Key Laboratory of Polymer Science and Technology, Guangdong Research Center for Interfacial Engineering of Functional Materials, College of Materials Science and Engineering, Shenzhen University, Shenzhen 518060, PR China.
authors.forename: Zaochuan
authors.initials: Z
authors.lastname: Ge
authors.affiliation: North Carolina State University, Raleigh, NC 27695, USA.
authors.forename: Wenwen
authors.initials: W
authors.lastname: Zhang
authors.affiliation: Nanshan District Key Lab for Biopolymers and Safety Evaluation, Shenzhen Key Laboratory of Polymer Science and Technology, Guangdong Research Center for Interfacial Engineering of Functional Materials, 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 / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology* / Q000633:toxicity; D001622:Betaine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology / Q000633:toxicity; D001672:Biocompatible Materials / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology* / Q000633:toxicity; D002460:Cell Line; D048271:Chitosan / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000494:pharmacology* / Q000633:toxicity; D004912:Erythrocytes / Q000166:cytology / Q000187:drug effects; D004926:Escherichia coli / Q000187:drug effects; D005347:Fibroblasts / Q000166:cytology / Q000187:drug effects; D006461:Hemolysis; D006801:Humans; D012995:Solubility; D013211:Staphylococcus aureus / Q000187:drug effects
chemical_list: D000900:Anti-Bacterial Agents; D001672:Biocompatible Materials; D001622:Betaine; C483727:sulfobetaine; D048271:Chitosan
keywords: Antibacterial; Biocompatibility; Biomaterials; Chitosan; Zwitterion