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Quaternary ammonium salts of chitosan containing aromatic ring: Synthesis, characterization, antimicrobial, antioxidant and cytotoxicity

文献类型：期刊论文

作者Cui, Jingmin1,3; Sun, Yan1,3; Wang, Linqing1,3; Ji, Yuting1,3; Zhao, Huishuang4; Sun, Mingzhi5; Guo, Zhanyong1,2; Dong, Fang1,3
刊名CARBOHYDRATE RESEARCH
出版日期2025-06-01
卷号552页码:10
ISSN号0008-6215
DOI10.1016/j.carres.2025.109431
通讯作者Guo, Zhanyong(zhanyongguo@hotmail.com) ; Dong, Fang(fdong@yic.ac.cn)
英文摘要Quaternary ammonium salts of chitosan have been widely used in the development of anti-microbial biomaterials for their important role in inhibiting the growth microorganisms. However, it is important to modify its structure to obtain more efficient and biologically active derivatives. Herein, a series of chitosan derivatives with antibacterial, antifungal, antioxidant, and non-cytotoxic properties was synthesized. These four quaternary ammonium salts of chitosan were prepared incorporating 2-thiophenecarboxaldehyde, 2-furancarboxaldehyde, 2-pyridinecarboxaldehyde and benzaldehyde to form Schiff bases, followed by a reductive amination to obtain the chitosan N-derivatives, and quaternized by iodomethane. The inhibition rate of thiophenecarboxaldehyde chitosan trimethyl ammonium iodide (TpTMC) to B. cinerea could reach 93.78 % and the inhibition ability of pyridinecarboxaldehyde chitosan trimethyl ammonium iodide (PyTMC) F. graminearum could reach 98.08 % at the concentration of 1.0 mg/mL. Furthermore, furancarboxaldehyde chitosan trimethyl ammonium iodide (FrTMC) exhibited a strong ability to scavenge hydroxyl radicals and DPPH radicals, especially the DPPH radicals scavenging ability was comparable to that of L-ascorbic acid at concentration of 1.6 mg/mL. The B3LYP/6-311++G (d,p) basis set was employed to determine electronic properties, including HOMO-LUMO energies, and analyze the chemical reactivity of the compounds. L929 cells were used to evaluate the cytotoxicity of the compounds at different concentrations (1-1000 mu g/mL). The results demonstrated the diverse applications of aromatic ring-modified quaternary ammonium salts of chitosan, along with their significant antioxidant and antifungal effects against plant fungi. Therefore, these compounds have potential applications in the preparation of agricultural, biological, and medical materials.
WOS关键词DENSITY-FUNCTIONAL THEORY ; N,N,N-TRIMETHYL CHITOSAN ; AGENT ; DERIVATIVES ; PREDICTION ; PRODUCTS
WOS研究方向Biochemistry & Molecular Biology ; Chemistry
语种英语
WOS记录号WOS:001435741600001
源URL[http://ir.yic.ac.cn/handle/133337/40337]  
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Guo, Zhanyong; Dong, Fang
作者单位1.Chinese Acad Sci, Yantai Inst Coastal Zone Res, Key Lab Coastal Biol & Bioresource Utilizat, Yantai 264003, Peoples R China
2.Jiangsu Ocean Univ, Coll Marine Life & Fisheries, Lianyungang 222005, Peoples R China
3.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
4.Yantai Univ, Sch Chem & Chem Engn, Yantai 264005, Peoples R China
5.Yantai Fuhui Agr Technol Co Ltd, Yantai 264000, Peoples R China
推荐引用方式
GB/T 7714		 Cui, Jingmin,Sun, Yan,Wang, Linqing,et al. Quaternary ammonium salts of chitosan containing aromatic ring: Synthesis, characterization, antimicrobial, antioxidant and cytotoxicity[J]. CARBOHYDRATE RESEARCH,2025,552:10.
APA Cui, Jingmin.,Sun, Yan.,Wang, Linqing.,Ji, Yuting.,Zhao, Huishuang.,...&Dong, Fang.(2025).Quaternary ammonium salts of chitosan containing aromatic ring: Synthesis, characterization, antimicrobial, antioxidant and cytotoxicity.CARBOHYDRATE RESEARCH,552,10.
MLA Cui, Jingmin,et al."Quaternary ammonium salts of chitosan containing aromatic ring: Synthesis, characterization, antimicrobial, antioxidant and cytotoxicity".CARBOHYDRATE RESEARCH 552(2025):10.

入库方式： OAI收割

来源：烟台海岸带研究所

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