Cationic Chitooligosaccharide Derivatives Bearing Pyridinium and Trialkyl Ammonium: Preparation, Characterization and Antimicrobial Activities

doi:10.3390/polym15010014

	Cationic Chitooligosaccharide Derivatives Bearing Pyridinium and Trialkyl Ammonium: Preparation, Characterization and Antimicrobial Activities
	Lin, Conghao 1,2; Guo, Zhanyong1 ; Jiang, Aili 2; Liang, Xiaorui 3; Tan, Wenqiang1
发表期刊	POLYMERS
	2023
卷号	15 期号:1 页码:15
关键词	chitooligosaccharide nicotinylation pyridinium cation antibacterial antifungal
DOI	10.3390/polym15010014
通讯作者	Guo, Zhanyong(zyguo@yic.ac.cn) ; Tan, Wenqiang(wqtan@yic.ac.cn)
英文摘要	In this study, chitooligosaccharide-niacin acid conjugate was designed and synthesized through the reaction of chitooligosaccharide and nicotinic acid with the aid of N,N '-carbonyldiimidazole. Its cationic derivatives were prepared by the further nucleophilic substitution reaction between the chitooligosaccharide-niacin acid conjugate and bromopropyl trialkyl ammonium bromide with different alkyl chain lengths. The specific structural characterization of all derivatives was identified using Fourier Transform Infrared Spectroscopy (FTIR) and Nuclear Magnetic Resonance (NMR), and the degree of substitution was obtained using the integral area ratio of the hydrogen signals. Specifically, the antibacterial activities against Escherichia coli, Staphylococcus aureus, Pseudoalteromonas citrea and Vibrio harveyi were evaluated using broth dilution methods. In addition, their antifungal activities, including Botrytis cinerea, Glomerella cingulate and Fusarium oxysporum f. sp. cubense were assayed in vitro using the mycelium growth rate method. Experimental data proved that the samples showed antibacterial activity against four pathogenic bacteria (MIC = 1-0.125 mg/mL, MBC = 8-0.5 mg/mL) and enhanced antifungal activity (50.30-68.48% at 1.0 mg/mL) against Botrytis cinerea. In particular, of all chitooligosaccharide derivatives, the chitooligosaccharide derivative containing pyridinium and tri-n-butylamine showed the strongest antibacterial capacity against all of the test pathogenic bacteria; the MIC against Vibrio harveyi was 0.125 mg/mL and the MBC was 1 mg/mL. The experimental results above showed that the introduction of pyridinium salt and quaternary ammonium salt bearing trialkyl enhanced the antimicrobial activity. In addition, the cytotoxicity against L929 cells of the chitooligosaccharide derivatives was evaluated, and the compounds exhibited slight cytotoxicity. Specifically, the cell viability was greater than 91.80% at all test concentrations. The results suggested that the cationic chitooligosaccharide derivatives bearing pyridinium and trialkyl ammonium possessed better antimicrobial activity than pure chitooligosaccharide, indicating their potential as antimicrobial agents in food, medicine, cosmetics and other fields.
收录类别	SCI
语种	英语
关键词[WOS]	BIOLOGICAL-ACTIVITIES ; QUATERNIZED CHITOSAN ; GRAFTED CHITOSAN ; ALKYL ; ANTIBACTERIAL
研究领域[WOS]	Polymer Science
WOS记录号	WOS:000908745000001
引用统计	被引频次：3[WOS] [WOS记录] [WOS相关记录]
文献类型	期刊论文
条目标识符	http://ir.yic.ac.cn/handle/133337/32505
专题	海岸带生物学与生物资源利用重点实验室海岸带生物学与生物资源利用重点实验室_海岸带生物资源高效利用研究与发展中心
通讯作者	Guo, Zhanyong; Tan, Wenqiang
作者单位	1.Chinese Acad Sci, Yantai Inst Coastal Zone Res, Yantai 264003, Peoples R China 2.Yantai Univ, Coll Life Sci, Yantai 264005, Peoples R China 3.Naval Aviat Univ, Sch Basic Sci Aviat, Yantai 264001, Peoples R China
推荐引用方式 GB/T 7714	Lin, Conghao,Guo, Zhanyong,Jiang, Aili,et al. Cationic Chitooligosaccharide Derivatives Bearing Pyridinium and Trialkyl Ammonium: Preparation, Characterization and Antimicrobial Activities[J]. POLYMERS,2023,15(1):15.
APA	Lin, Conghao,Guo, Zhanyong,Jiang, Aili,Liang, Xiaorui,&Tan, Wenqiang.(2023).Cationic Chitooligosaccharide Derivatives Bearing Pyridinium and Trialkyl Ammonium: Preparation, Characterization and Antimicrobial Activities.POLYMERS,15(1),15.
MLA	Lin, Conghao,et al."Cationic Chitooligosaccharide Derivatives Bearing Pyridinium and Trialkyl Ammonium: Preparation, Characterization and Antimicrobial Activities".POLYMERS 15.1(2023):15.