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

文献类型：期刊论文

作者Lin, Conghao4,5; Luan, Fang3; Su, Shengjia2; Jiang, Aili4; Tan, Wenqiang1,5; Guo, Zhanyong1,5
刊名CARBOHYDRATE RESEARCH
出版日期2023-11-01
卷号533页码:11
ISSN号0008-6215
关键词Chitooligosaccharide Pyridinium cation Fluorobenzyl Antibacterial Antifungal
DOI10.1016/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.
WOS关键词BIOLOGICAL-ACTIVITIES ; ANTIFUNGAL ACTIVITY ; CHITOSAN ; ANTIBACTERIAL ; ANTIOXIDANT
WOS研究方向Biochemistry & Molecular Biology ; Chemistry
语种英语
WOS记录号WOS:001079804900001
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
源URL[http://ir.yic.ac.cn/handle/133337/32830]  
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, Yantai 264003, Peoples R China
2.Shandong Saline Alkali Land Modern Agr Co, Dongying 257300, Peoples R China
3.Shandong Jiaotong Univ, Naval Architecture & Port Engn Coll, Weihai 264200, Peoples R China
4.Yantai Univ, Coll Life Sci, Yantai 264005, Peoples R China
5.Chinese Acad Sci, Yantai Inst Coastal Zone Res, Res & Dev Ctr Efficient Utilizat Coastal Bioresour, 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.

入库方式： OAI收割

来源：烟台海岸带研究所

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