Preparation of N-(2-hydroxypropyltrimonium chloride)-O-dodecylylpyridine chitosan quaternary ammonium salt and its antibacterial activities

Yu Pang; Lulu Shi; Lin Wang; Tao Zhang; Meihua Xin; Mingchun Li; Yangfan Mao

doi:10.1016/j.carres.2024.109306

Preparation of N-(2-hydroxypropyltrimonium chloride)-O-dodecylylpyridine chitosan quaternary ammonium salt and its antibacterial activities

Carbohydr Res. 2024 Dec:546:109306. doi: 10.1016/j.carres.2024.109306. Epub 2024 Nov 5.

Authors

Yu Pang¹, Lulu Shi¹, Lin Wang², Tao Zhang¹, Meihua Xin³, Mingchun Li⁴, Yangfan Mao⁵

Affiliations

¹ College of Material Science and Engineering, Huaqiao University, Engineering Research Center of Environment-Friendly Functional Materials, Ministry of Education, Xiamen, 361021, Fujian, PR China.
² College of Material Science and Engineering, Huaqiao University, Engineering Research Center of Environment-Friendly Functional Materials, Ministry of Education, Xiamen, 361021, Fujian, PR China; School of Chemistry and Environment, Ankang University, The Youth Innovation Team of Shaanxi Universities of Development and Utilization of Qinba Chinese Medicine Resources, Qinba Chinese Medicine Resources R&D Center, Ankang, 725000, Shaanxi, PR China. Electronic address: [email protected].
³ College of Material Science and Engineering, Huaqiao University, Engineering Research Center of Environment-Friendly Functional Materials, Ministry of Education, Xiamen, 361021, Fujian, PR China. Electronic address: [email protected].
⁴ College of Material Science and Engineering, Huaqiao University, Engineering Research Center of Environment-Friendly Functional Materials, Ministry of Education, Xiamen, 361021, Fujian, PR China. Electronic address: [email protected].
⁵ The Instrumental Analysis Center, Huaqiao University, Xiamen, 361021, Fujian, PR China.

PMID: 39520806
DOI: 10.1016/j.carres.2024.109306

Abstract

Chitosan derivatives, including O-carboxymethyl chitosan (CMC), N-(2-hydroxypropyltrimonium chloride)-O-carboxymethyl chitosan (QCMC), and N-(2-hydroxypropyltrimonium chloride)-O-dodecylylpyridine chitosan quaternary ammonium salt (DQCMC), were synthesized and characterized using Fourier transform infrared (FTIR) spectroscopy, ¹H nuclear magnetic resonance (¹H NMR) spectroscopy, Ultraviolet-visible (UV-vis) spectroscopy, and element analysis (EA). The antibacterial activities of chitosan and chitosan derivatives against Escherichia coli (E. coli) and Staphylococcus aureus (S. aureus) were evaluated through the minimum inhibitory concentration (MIC), minimum bactericidal concentration (MBC), and antibacterial rate assays. Results demonstrated that DQCMC exhibited significantly higher antibacterial efficacy compared to chitosan, CMC, and QCMC. The MIC of DQCMC against E. coli and S. aureus were 31 μg/mL and 7 μg/mL, respectively, with a 100 % antibacterial rate at a concentration of 0.5 mg/mL. Furthermore, assessment of mouse fibroblast (L929) cell viability using cell counting kit-8 (CCK-8) methods revealed no toxicity associated with the material.

Keywords: Amphiphilic; Antibacterial; Cytotoxicity; Micelle; Modified chitosan; Self-assembly.

MeSH terms

Animals
Anti-Bacterial Agents* / chemical synthesis
Anti-Bacterial Agents* / chemistry
Anti-Bacterial Agents* / pharmacology
Cell Line
Chitosan* / analogs & derivatives
Chitosan* / chemical synthesis
Chitosan* / chemistry
Chitosan* / pharmacology
Escherichia coli* / drug effects
Mice
Microbial Sensitivity Tests*
Pyridines / chemical synthesis
Pyridines / chemistry
Pyridines / pharmacology
Quaternary Ammonium Compounds* / chemical synthesis
Quaternary Ammonium Compounds* / chemistry
Quaternary Ammonium Compounds* / pharmacology
Staphylococcus aureus* / drug effects

Substances

Anti-Bacterial Agents
Chitosan
Quaternary Ammonium Compounds
Pyridines