Su Zhongwen, Peng Yonggang, Yu Ying, Zhong Yujing, Zeng Junyue, Chen Yikai, Vijayakumar Sekar, Mao Yangfan, Wang Lin, Xin Meihua, Li Mingchun
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 and School of Biomedical Sciences, Huaqiao University, Xiamen 361021, China.
Int J Biol Macromol. 2025 May;307(Pt 3):142098. doi: 10.1016/j.ijbiomac.2025.142098. Epub 2025 Mar 13.
In this study, three chitosan quaternary phosphonium salts and three chitosan quaternary ammonium salts with varying spacer chain lengths were synthesized. Structure characterization of the obtained products was conducted using Fourier-transform infrared spectroscopy, nuclear magnetic resonance, thermogravimetric analysis, and elemental analysis. Additionally, the in vitro scavenging efficiency of these derivatives against 2,2-diphenyl-1-picrylhydrazyl (DPPH) and superoxide radicals, as well as their antibacterial activities against Escherichia coli (E. coli) and Staphylococcus aureus (S. aureus), were evaluated. The results indicated that the scavenging efficiency of the chitosan quaternary phosphonium salt at a concentration of 1.6 mg/mL ranged from 36.9 % to 48.7 % for DPPH free radicals and from 48.3 % to 66.3 % for superoxide free radicals, outperforming that of the chitosan quaternary ammonium salt with long alkyl chains. Furthermore, an increase in the length of the spacer alkyl chain was associated with enhanced antibacterial activities of the corresponding chitosan derivatives. At a concentration of 1.0 mg/mL, the synthesized chitosan derivatives demonstrated antibacterial rates exceeding 90 % against both E. coli and S. aureus. Notably, the CCK-8 assay confirmed that these derivatives are non-toxic to 293 T cells. Among the six derivatives, TPPBOC and DMDOC, characterized by longer spacer alkyl chains, demonstrated superior antioxidant and antibacterial activities. This research establishes a robust theoretical foundation for the development of more effective and safer antioxidants and antibacterial agents, thereby enriching the knowledge base in chitosan chemistry and functional materials, and paving new pathways for the innovation of novel antioxidant and antibacterial materials.
在本研究中，合成了三种具有不同间隔链长度的壳聚糖季鏻盐和三种壳聚糖季铵盐。使用傅里叶变换红外光谱、核磁共振、热重分析和元素分析对所得产物进行结构表征。此外，评估了这些衍生物对2,2-二苯基-1-苦基肼自由基（DPPH）和超氧自由基的体外清除效率，以及它们对大肠杆菌（E. coli）和金黄色葡萄球菌（S. aureus）的抗菌活性。结果表明，浓度为1.6 mg/mL的壳聚糖季鏻盐对DPPH自由基的清除效率为36.9%至48.7%，对超氧自由基的清除效率为48.3%至66.3%，优于具有长烷基链的壳聚糖季铵盐。此外，间隔烷基链长度的增加与相应壳聚糖衍生物抗菌活性的增强相关。在浓度为1.0 mg/mL时，合成的壳聚糖衍生物对大肠杆菌和金黄色葡萄球菌的抗菌率均超过90%。值得注意的是，CCK-8试验证实这些衍生物对293 T细胞无毒。在六种衍生物中，具有较长间隔烷基链的TPPBOC和DMDOC表现出优异的抗氧化和抗菌活性。本研究为开发更有效、更安全的抗氧化剂和抗菌剂奠定了坚实的理论基础，从而丰富了壳聚糖化学和功能材料的知识基础，并为新型抗氧化和抗菌材料的创新开辟了新途径。
