Synthesis, characterization, and anti-tumor properties of O-benzoylselenoglycolic chitosan

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

doi:10.1016/j.ijbiomac.2021.10.086

Synthesis, characterization, and anti-tumor properties of O-benzoylselenoglycolic chitosan

Int J Biol Macromol. 2021 Dec 15;193(Pt A):491-499. doi: 10.1016/j.ijbiomac.2021.10.086. Epub 2021 Oct 20.

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. Electronic address: lingyun.chen@ualberta.ca.
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: 34678382
DOI: 10.1016/j.ijbiomac.2021.10.086

Abstract

This study introduces a facile method for synthesizing O-benzoylselenoglycolic chitosan with a high selenium concentration of 45.32 mg/g. The characterizations of the chemical structure via FTIR, ¹H NMR, ¹³C NMR, TGA, and XRD analyses indicated that benzoylselenoglycolic acid was successfully grafted onto the C6 hydroxyl group of chitosan. The anti-cancer activity of the O-benzoylselenoglycolic chitosan was investigated in vitro using a HepG2 cell model, and the results indicated that it has excellent anticancer activity against HepG2 cancer cells with an IC₅₀ value of 0.53 μg/mL while exhibiting non-toxicity against normal cells (L-02). Furthermore, a mechanistic study revealed that the O-benzoylselenoglycolic chitosan could induce early apoptosis, G2/M, S phase arrest, and activation of caspase-3 activity to inhibit the HepG2 cell growth. This study has led to novel organic selenium species, and the results suggest its potential to be used as an effective ingredient for cancer prevention and therapy in the food and pharmaceutical fields.

Keywords: Anti-cancer activity; Benzoylselenoglycolic acid; Chitosan; HepG2 cells; Selenium.

MeSH terms

Antineoplastic Agents* / chemistry
Antineoplastic Agents* / pharmacology
Apoptosis / drug effects*
Chitosan* / chemistry
Chitosan* / pharmacology
Hep G2 Cells
Humans
Neoplasms / drug therapy*
Selenium* / chemistry
Selenium* / pharmacology

Substances

Antineoplastic Agents
Chitosan
Selenium