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

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

doi:10.1016/j.ijbiomac.2024.138638

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

Int J Biol Macromol. 2024 Dec 10:285:138638. doi: 10.1016/j.ijbiomac.2024.138638. Online ahead of print.

Authors

Yonggang Peng¹, Ying Yu¹, Zhongwen Su¹, Yujing Zhong¹, Yikai Chen², Sekar Vijayakumar¹, Lin Wang³, Meihua Xin⁴, Mingchun Li⁵

Affiliations

¹ College of Material Science and Engineering, Huaqiao University, Engineering Research Center of Environment-Friendly Functional Materials, Ministry of Education, Xiamen 361021, China.
² Center for Precision Medicine, School of Medicine, School of Biomedical Sciences, Huaqiao University, Xiamen 361021, China.
³ College of Material Science and Engineering, Huaqiao University, Engineering Research Center of Environment-Friendly Functional Materials, Ministry of Education, Xiamen 361021, China. Electronic address: wanglin@hqu.edu.cn.
⁴ College of Material Science and Engineering, Huaqiao University, Engineering Research Center of Environment-Friendly Functional Materials, Ministry of Education, Xiamen 361021, China. Electronic address: mhxin@hqu.edu.cn.
⁵ College of Material Science and Engineering, Huaqiao University, Engineering Research Center of Environment-Friendly Functional Materials, Ministry of Education, Xiamen 361021, China. Electronic address: mcli@hqu.edu.cn.

PMID: 39667471
DOI: 10.1016/j.ijbiomac.2024.138638

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, ¹H 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.

Keywords: Antimicrobial; Antioxidant activities; Biocompatibility; Chitosan; Novel ionic compounds.