Preparation of cationic chitooligosaccharide derivatives bearing N-halogenated benzyl pyridinium and assessment of their antimicrobial activities

doi:10.1007/s00289-022-04650-z

CORC > 烟台海岸带研究所 > 中国科学院烟台海岸带研究所 > 海岸带生物学与生物资源利用重点实验室

	Preparation of cationic chitooligosaccharide derivatives bearing N-halogenated benzyl pyridinium and assessment of their antimicrobial activities
	Lin, Conghao 3; Yuan, Yuting 1,3; Tan, Wenqiang 2; Guo, Zhanyong 1,2; Jiang, Aili 3
刊名	POLYMER BULLETIN
	2022-12-21
页码	18
关键词	Cationic chitooligosaccharide derivatives N-Halogenated benzyl pyridinium Antimicrobial
ISSN号	0170-0839
DOI	10.1007/s00289-022-04650-z
通讯作者	Tan, Wenqiang(wqtan@yic.ac.cn) ; Jiang, Aili(jal9035@163.com)
英文摘要	As one of the most promising and eco-friendly oligosaccharides with a variety of potential biological activities, chitooligosaccharide has attracted much attention because of its unique properties. The modification of chitooligosaccharide has been used for synthesizing novel chitooligosaccharide derivatives with excellent antimicrobial activities. In this work, chitooligosaccharide-niacin acid conjugate was firstly synthesized by using N,N & PRIME;-carbonyldiimidazole as catalyst and its cationic derivatives were obtained by further nucleophilic reaction between chitooligosaccharide-niacin acid conjugate and halogenated benzyl bromide. The structural characteristics of chitooligosaccharide derivatives were investigated by FTIR and NMR. In addition, the antimicrobial property of three end products against three plant-threatening fungal pathogens and four harmful bacteria was evaluated by the disc diffusion method. The in vitro antimicrobial activities results presented a significantly improved inhibition capability against pathogenic microorganisms of cationic chitooligosaccharide derivatives bearing N-halogenated benzyl pyridinium as compared to chitooligosaccharide and chitooligosaccharide-niacin acid conjugate. Specifically, all end products possessed significant enhancement in antimicrobial activities, the inhibition zones of the derivatives were from 6.3 to 19.4 mm against fungi and compounds also had excellent bacteriostatic activity (7.7-20.8 mm). Specially, chitooligosaccharide derivative bearing 4-chlorobenzyl showed the strongest antifungal activity, its inhibition zone reached up to 19.4 mm against F. oxysporum, which was close to the carbendazim (22.3 mm), it also showed excellent antibacterial activity against harmful bacterial, its bacteriostatic diameter was astonishingly 20.8 mm. These data indicated that the introduction of pyridinium salt with halogenated benzyl by the reaction of halogenated benzyl bromide groups and chitooligosaccharide-niacin acid conjugate could conspicuously enhance the antimicrobial effect. Chitooligosaccharide derivatives with enhanced antimicrobial activities could serve as potential biomaterial for antimicrobial applications.
WOS关键词	ANTIFUNGAL ACTIVITY ; ANTIBACTERIAL ACTIVITY ; BIOLOGICAL-ACTIVITIES ; CHITOSAN
WOS研究方向	Polymer Science
语种	英语
WOS记录号	WOS:000900093200001
资助机构	Youth Innovation Promotion Association CAS ; Key Deployment Project of Center for Ocean Mega-Science of CAS ; National Key Research and Development Program of China
内容类型	期刊论文
源URL	[http://ir.yic.ac.cn/handle/133337/32422]
专题	海岸带生物学与生物资源利用重点实验室
通讯作者	Tan, Wenqiang; Jiang, Aili
作者单位	1.Univ Chinese Acad Sci, Beijing 100049, Peoples R China 2.Chinese Acad Sci, Yantai Inst Coastal Zone Res, Res & Dev Ctr Efficient Utilizat Coastal Bioresour, Yantai 264003, Peoples R China 3.Yantai Univ, Coll Life Sci, Yantai 264005, Peoples R China
推荐引用方式 GB/T 7714	Lin, Conghao,Yuan, Yuting,Tan, Wenqiang,et al. Preparation of cationic chitooligosaccharide derivatives bearing N-halogenated benzyl pyridinium and assessment of their antimicrobial activities[J]. POLYMER BULLETIN,2022:18.
APA	Lin, Conghao,Yuan, Yuting,Tan, Wenqiang,Guo, Zhanyong,&Jiang, Aili.(2022).Preparation of cationic chitooligosaccharide derivatives bearing N-halogenated benzyl pyridinium and assessment of their antimicrobial activities.POLYMER BULLETIN,18.
MLA	Lin, Conghao,et al."Preparation of cationic chitooligosaccharide derivatives bearing N-halogenated benzyl pyridinium and assessment of their antimicrobial activities".POLYMER BULLETIN (2022):18.