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基于磺酸吡啶鎓的新型离子型壳聚糖衍生物:合成、表征及抗菌、抗氧化和生物相容性性能研究

Novel ionic chitosan derivatives based on pyridinium sulfonate: Synthesis, characterization, and studies on antimicrobial, antioxidant, and biocompatibility properties.

作者信息

Peng Yonggang, Yu Ying, Su Zhongwen, Zhong Yujing, Chen Yikai, Vijayakumar Sekar, Wang Lin, Xin Meihua, Li Mingchun

机构信息

College of Material Science and Engineering, Huaqiao University, Engineering Research Center of Environment-Friendly Functional Materials, Ministry of Education, Xiamen 361021, China.

Center for Precision Medicine, School of Medicine, School of Biomedical Sciences, Huaqiao University, Xiamen 361021, China.

出版信息

Int J Biol Macromol. 2025 Jan;285:138638. doi: 10.1016/j.ijbiomac.2024.138638. Epub 2024 Dec 10.

Abstract

To improve the solubility, antimicrobial efficacy, antioxidant capacity, and biocompatibility of chitosan for broader applications, a series of novel ionic chitosan derivatives were synthesized in this study by amidating chitosan with carboxyl pyridinium sulfonate. These derivatives were characterized through various analytical techniques, including FTIR, H NMR, UV, TGA, and XRD. Proton NMR was particularly utilized to determine the degree of substitution. The modified chitosans showed improved water solubility. Their antimicrobial activity against gram negative E. coli and gram positive S. aureus was evaluated in vitro through inhibition rates, minimum inhibitory concentrations (MIC), and minimum bactericidal concentrations (MBC), demonstrating high effectiveness at low concentrations. Additionally, antioxidant tests indicated that these derivatives possess significantly greater antioxidant activities compared to original chitosan, particularly the 5OHNASCS derivative which showed exceptional radical scavenging and reducing capabilities. Furthermore, the CCK-8 assay was employed to assess cytotoxicity in 293 T cells (human embryonic kidney cells), with all samples exhibiting no toxicity. Hemolysis tests were also conducted, revealing that the newly synthesized series of ionic chitosan derivatives showed no hemolytic activity, indicating good biocompatibility and potential for application as wound dressings. In summary, these newly developed ionic chitosan derivatives demonstrated excellent water solubility, antimicrobial activity, antioxidant capacity, and biocompatibility, suggesting their potential use in food and biomedical materials.

摘要

为了提高壳聚糖的溶解度、抗菌效果、抗氧化能力和生物相容性,以便更广泛地应用,本研究通过壳聚糖与羧基吡啶鎓磺酸盐酰胺化反应合成了一系列新型离子型壳聚糖衍生物。通过包括傅里叶变换红外光谱(FTIR)、氢核磁共振(H NMR)、紫外光谱(UV)、热重分析(TGA)和X射线衍射(XRD)在内的各种分析技术对这些衍生物进行了表征。尤其利用质子核磁共振来确定取代度。改性壳聚糖的水溶性有所提高。通过抑制率、最低抑菌浓度(MIC)和最低杀菌浓度(MBC)在体外评估了它们对革兰氏阴性大肠杆菌和革兰氏阳性金黄色葡萄球菌的抗菌活性,结果表明在低浓度下具有高效性。此外,抗氧化测试表明,这些衍生物与原始壳聚糖相比具有显著更高的抗氧化活性,特别是5OHNASCS衍生物表现出卓越的自由基清除和还原能力。此外,采用CCK-8法评估了对293 T细胞(人胚胎肾细胞)的细胞毒性,所有样品均无毒性。还进行了溶血试验,结果表明新合成的一系列离子型壳聚糖衍生物无溶血活性,表明其具有良好的生物相容性,有作为伤口敷料应用的潜力。总之,这些新开发的离子型壳聚糖衍生物表现出优异的水溶性、抗菌活性、抗氧化能力和生物相容性,表明它们在食品和生物医学材料方面具有潜在用途。

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