Synthesis, characterization, and biological evaluation of novel selenium-containing chitosan derivatives

Wanwen Chen; Hao Cheng; Lingyun Chen; Xiaobei Zhan; Wenshui Xia

doi:10.1016/j.carbpol.2022.119185

Synthesis, characterization, and biological evaluation of novel selenium-containing chitosan derivatives

Carbohydr Polym. 2022 May 15:284:119185. doi: 10.1016/j.carbpol.2022.119185. Epub 2022 Jan 29.

Authors

Wanwen Chen¹, Hao Cheng², Lingyun Chen³, Xiaobei Zhan⁴, Wenshui Xia⁵

Affiliations

¹ School of Food Science and Technology, State Key Laboratory of Food Science and Technology, Jiangnan University, Jiangsu, China; Department of Agricultural, Food and Nutritional Science, University of Alberta, Edmonton, AB, Canada; Collaborative Innovation Center of Food Safety and Quality Control in Jiangsu Province, Jiangnan University, Jiangsu, China; Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, Jiangsu, China.
² School of Food Science and Technology, State Key Laboratory of Food Science and Technology, Jiangnan University, Jiangsu, China; Department of Agricultural, Food and Nutritional Science, University of Alberta, Edmonton, AB, Canada.
³ Department of Agricultural, Food and Nutritional Science, University of Alberta, Edmonton, AB, Canada.
⁴ Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, Jiangsu, China.
⁵ School of Food Science and Technology, State Key Laboratory of Food Science and Technology, Jiangnan University, Jiangsu, China; Collaborative Innovation Center of Food Safety and Quality Control in Jiangsu Province, Jiangnan University, Jiangsu, China. Electronic address: xiaws@jiangnan.edu.cn.

PMID: 35287904
DOI: 10.1016/j.carbpol.2022.119185

Abstract

Though great efforts have been made to develop selenium polysaccharides with unique properties using HNO₃-Na₂SeO₃ methods, the Se content is still low due to the poor esterification efficiency of H₂SeO₃. Herein, selenodiacetic acid (SA) was introduced into chitosan (CS) to synthesize O-selenodiacetyl chitosan (OSAC) and chitosan-ammonium selenodiacetate (CASA) by covalent and non-covalent interaction, respectively. The obtained CS derivatives were characterized by UV-vis, FTIR, ¹H NMR, XPS, TGA, and XRD spectra, and the OSAC and CASA showed high Se content up to 15,720 ± 475 and 26,363 ± 698 μg/g. The OSAC and CASA demonstrated increased antioxidant activities compared to the CS in DPPH and ABTS free radical scavenging assays. Moreover, they exhibited a potent anticancer effect on HepG2 cells with the IC₅₀ values of 0.918 and 1.459 μg/mL. Taken together, this study provides a promising strategy for the design of novel selenium polysaccharides with high Se content and greater biological activity.

Keywords: Anticancer; Antioxidant; Chitosan; Selenium content; Selenium polysaccharides; Selenodiacetic acid.

MeSH terms

Antioxidants / chemistry
Chitosan* / chemistry
Hep G2 Cells
Humans
Polysaccharides
Selenium* / chemistry

Substances

Antioxidants
Polysaccharides
Chitosan
Selenium