Water-soluble fluorine-functionalized chitooligosaccharide derivatives: Synthesis, characterization and antimicrobial activity

doi:10.1016/j.carres.2023.108935

	Water-soluble fluorine-functionalized chitooligosaccharide derivatives: Synthesis, characterization and antimicrobial activity
	Lin, Conghao 1,2; Luan, Fang 3; Su, Shengjia 4; Jiang, Aili 2; Tan, Wenqiang1,5 ; Guo, Zhanyong1,5
发表期刊	CARBOHYDRATE RESEARCH
ISSN	0008-6215
	2023-11-01
卷号	533 页码:11
关键词	Chitooligosaccharide Pyridinium cation Fluorobenzyl Antibacterial Antifungal
DOI	10.1016/j.carres.2023.108935
通讯作者	Tan, Wenqiang(wqtan@yic.ac.cn) ; Guo, Zhanyong(zyguo@yic.ac.cn)
英文摘要	In this work, a series of water-soluble fluorine-functionalized chitooligosaccharide derivatives were synthesized by conjugating nicotinic acid to chitooligosaccharide via nicotinylation reaction, followed by nucleophilic reaction with ethyl bromide, benzyl bromide and fluorobenzyl bromides. Synthesized derivatives were identified structurally by Fourier Transform Infrared Spectroscopy and Nuclear Magnetic Resonance. In addition, the antibacterial activities of chitooligosaccharide derivatives against several disease-causing bacteria were assessed by the broth dilution method and Kirby-Bauer method, the mycelium growth rate method was used to assessing the antifungal properties of samples against three plant-threatening fungi. Among the chitooligosaccharide derivatives, those containing benzyl or fluorobenzyl exhibited noteworthy antimicrobial activity. Specifically, the chitooligosaccharide derivative containing 2,3,4-trifluorobenzyl displayed remarkable antimicrobial activity, with an inhibition index of 84.35% against Botryis cinerea at a concentration of 1.0 mg/mL. Additionally, its MIC value against Staphylococcus aureus was found to be 0.03125 mg/mL, while the MBC value was determined to be 0.0625 mg/mL. The findings of the study revealed that the incorporation of pyridinium cations and fluorine into the chitooligosaccharide backbone may play a critical role in strengthening its ability to combat harmful microorganisms. Furthermore, the cytotoxicities of chitooligosaccharide derivatives against Huvec cells were evaluated through MTT assay, and all samples were not toxic. As a consequence, the water-soluble fluorinefunctionalized chitooligosaccharide derivatives possessed rapid microbicidal properties and good biocompatibility, which provided promising prospects for the development of a more effective and environmentally friendly antimicrobial agent.
资助机构	Youth Innovation Promotion Association CAS ; Natural Science Foundation of Shandong Province of China ; Science & Technology Specific Projects in Agricultural High-tech Industrial Demonstration Area of the Yellow River Delta ; Shandong Key R&D Plan, Major Scientific and Technological Innovation Project ; Science & Technology Specific Projects in Agricultural High-tech Industrial Demonstration Area of the Yellow River Delta
收录类别	SCI
语种	英语
关键词[WOS]	BIOLOGICAL-ACTIVITIES ; ANTIFUNGAL ACTIVITY ; CHITOSAN ; ANTIBACTERIAL ; ANTIOXIDANT
研究领域[WOS]	Biochemistry & Molecular Biology ; Chemistry
WOS记录号	WOS:001079804900001
引用统计
文献类型	期刊论文
条目标识符	http://ir.yic.ac.cn/handle/133337/32831
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	Tan, Wenqiang; Guo, Zhanyong
作者单位	1.Chinese Acad Sci, Yantai Inst Coastal Zone Res, Res & Dev Ctr Efficient Utilizat Coastal Bioresour, Yantai 264003, Peoples R China 2.Yantai Univ, Coll Life Sci, Yantai 264005, Peoples R China 3.Shandong Jiaotong Univ, Naval Architecture & Port Engn Coll, Weihai 264200, Peoples R China 4.Shandong Saline Alkali Land Modern Agr Co, Dongying 257300, Peoples R China 5.Chinese Acad Sci, Yantai Inst Coastal Zone Res, Yantai 264003, Peoples R China
推荐引用方式 GB/T 7714	Lin, Conghao,Luan, Fang,Su, Shengjia,et al. Water-soluble fluorine-functionalized chitooligosaccharide derivatives: Synthesis, characterization and antimicrobial activity[J]. CARBOHYDRATE RESEARCH,2023,533:11.
APA	Lin, Conghao,Luan, Fang,Su, Shengjia,Jiang, Aili,Tan, Wenqiang,&Guo, Zhanyong.(2023).Water-soluble fluorine-functionalized chitooligosaccharide derivatives: Synthesis, characterization and antimicrobial activity.CARBOHYDRATE RESEARCH,533,11.
MLA	Lin, Conghao,et al."Water-soluble fluorine-functionalized chitooligosaccharide derivatives: Synthesis, characterization and antimicrobial activity".CARBOHYDRATE RESEARCH 533(2023):11.