Synthesis of N-isonicotinic sulfonate chitosan and its antibiofilm activity against E. coli and S. aureus

IF 2.4 3区化学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY

Carbohydrate Research Pub Date : 2024-06-17 DOI:10.1016/j.carres.2024.109194

Lin Wang , Yu Pang , Zhongwen Su , Meihua Xin , Mingchun Li , Yangfan Mao

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Abstract

N-(sodium 2-hydroxypropylsulfonate) chitosan (HSCS), N-sulfonate chitosan (SCS) and N-isonicotinic sulfonate chitosan (ISCS) were prepared. The structures of the prepared chitosan derivatives were characterized by nuclear magnetic resonance (¹H NMR) spectroscopy, Fourier transform infrared (FTIR) spectroscopy, ultraviolet–visible (UV–vis) spectroscopy and elemental analysis (EA). Antibacterial and antibiofilm activities of these chitosan derivatives were evaluated in vitro. The minimum inhibitory concentration (MIC) of HSCS and SCS against Escherichia coli (E. coli) and Staphylococcus aureus (S. aureus) were 0.625 mg/mL and 0.156 mg/mL, respectively. ISCS exhibited MIC values of 0.313 mg/mL and 0.078 mg/mL against E. coli and S. aureus, respectively. ISCS demonstrated superior antibacterial and antibiofilm properties compared to SCS and HSCS. These findings suggest that the incorporation of a pyridine structure into sulfonate chitosan enhances its antibacterial and antibiofilm activities, and the prepared ISCS has a promising application prospect for controlling the reproduction of microorganisms in the field of food packaging.

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N- 异烟酸磺酸盐壳聚糖的合成及其对大肠杆菌和金黄色葡萄球菌的抗生物膜活性

制备了 N-（2-羟基丙基磺酸钠）壳聚糖（HSCS）、N-磺酸盐壳聚糖（SCS）和 N-异烟酸磺酸盐壳聚糖（ISCS）。通过核磁共振（1H NMR）光谱、傅立叶变换红外（FTIR）光谱、紫外-可见（UV-vis）光谱和元素分析（EA）对所制备壳聚糖衍生物的结构进行了表征。对这些壳聚糖衍生物的抗菌和抗生物膜活性进行了体外评估。HSCS 和 SCS 对大肠杆菌（E. coli）和金黄色葡萄球菌（S. aureus）的最小抑菌浓度（MIC）分别为 0.625 mg/mL 和 0.156 mg/mL。ISCS 对大肠杆菌和金黄色葡萄球菌的 MIC 值分别为 0.313 mg/mL 和 0.078 mg/mL。与 SCS 和 HSCS 相比，ISCS 表现出更优越的抗菌和抗生物膜特性。这些研究结果表明，在磺酸盐壳聚糖中加入吡啶结构可增强其抗菌和抗生物膜活性，所制备的 ISCS 在食品包装领域控制微生物繁殖方面具有广阔的应用前景。

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来源期刊

Carbohydrate Research 化学-生化与分子生物学

CiteScore

5.00

自引率

3.20%

发文量

183

审稿时长

3.6 weeks

期刊介绍： Carbohydrate Research publishes reports of original research in the following areas of carbohydrate science: action of enzymes, analytical chemistry, biochemistry (biosynthesis, degradation, structural and functional biochemistry, conformation, molecular recognition, enzyme mechanisms, carbohydrate-processing enzymes, including glycosidases and glycosyltransferases), chemical synthesis, isolation of natural products, physicochemical studies, reactions and their mechanisms, the study of structures and stereochemistry, and technological aspects. Papers on polysaccharides should have a "molecular" component; that is a paper on new or modified polysaccharides should include structural information and characterization in addition to the usual studies of rheological properties and the like. A paper on a new, naturally occurring polysaccharide should include structural information, defining monosaccharide components and linkage sequence. Papers devoted wholly or partly to X-ray crystallographic studies, or to computational aspects (molecular mechanics or molecular orbital calculations, simulations via molecular dynamics), will be considered if they meet certain criteria. For computational papers the requirements are that the methods used be specified in sufficient detail to permit replication of the results, and that the conclusions be shown to have relevance to experimental observations - the authors'' own data or data from the literature. Specific directions for the presentation of X-ray data are given below under Results and "discussion".