Preparation, characterization and antioxidant activity of protocatechuic acid grafted carboxymethyl chitosan and its hydrogel

Chao Xu; Shui Guan; Jianqiang Xu; Weitao Gong; Tianqing Liu; Xuehu Ma; Changkai Sun

doi:10.1016/j.carbpol.2020.117210

Preparation, characterization and antioxidant activity of protocatechuic acid grafted carboxymethyl chitosan and its hydrogel

Carbohydr Polym. 2021 Jan 15:252:117210. doi: 10.1016/j.carbpol.2020.117210. Epub 2020 Oct 13.

Authors

Chao Xu¹, Shui Guan², Jianqiang Xu³, Weitao Gong⁴, Tianqing Liu¹, Xuehu Ma¹, Changkai Sun⁵

Affiliations

¹ State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, China; Dalian R&D Center for Stem Cell and Tissue Engineering, Dalian University of Technology, Dalian 116024, China.
² State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, China; Dalian R&D Center for Stem Cell and Tissue Engineering, Dalian University of Technology, Dalian 116024, China; Research & Educational Center for the Control Engineering of Translational Precision Medicine (R-ECCE-TPM), School of Biomedical Engineering, Faculty of Electronic Information and Electrical Engineering, Dalian University of Technology, Dalian 116024, China. Electronic address: guanshui@dlut.edu.cn.
³ State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, China; School of Life Science and Medicine, Dalian University of Technology, Panjin Campus, Panjin 124221, China.
⁴ State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, China.
⁵ State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, China; Research & Educational Center for the Control Engineering of Translational Precision Medicine (R-ECCE-TPM), School of Biomedical Engineering, Faculty of Electronic Information and Electrical Engineering, Dalian University of Technology, Dalian 116024, China.

PMID: 33183643
DOI: 10.1016/j.carbpol.2020.117210

Abstract

In this study, protocatechuic acid (PCA) was grafted onto carboxymethyl chitosan (CMCS) via EDC/NHS to improve the antioxidant effect. The grafting ratio of PCA-g-CMCS conjugates could be controlled by adjusting the pH value and feed ratio of raw materials. The conjugates exhibited similar pH sensitivity to CMCS and showed dramatic enhancements of DPPH and ABTS radicals scavenging activities, total antioxidant capacity, reducing power, and Fe²⁺-chelating activity. Three-dimensional porous PCA-g-CMCS hydrogel was prepared by lyophilization and secondary cross-linking. The shaped hydrogel preserved its antioxidant activity, and the sustained release of PCA-containing degraded fragment from biodegradable hydrogel could be achieved with the aid of lysozyme in vitro (15 days). PCA-g-CMCS hydrogel also showed excellent biocompatibility and protective effect on H₂O₂-induced oxidative damage in SH-SY5Y cells. These results suggested that PCA-g-CMCS conjugates and its hydrogel would appear to be a promising oxidation-resistant material for applications such as drug release and tissue engineering.

Keywords: Antioxidant; Carboxymethyl chitosan; Hydrogel; Protocatechuic acid.

MeSH terms

Antioxidants* / chemical synthesis
Antioxidants* / chemistry
Antioxidants* / pharmacology
Biocompatible Materials / chemistry*
Cell Line
Chitosan / analogs & derivatives*
Chitosan / chemistry
Humans
Hydrogels / chemistry*
Hydroxybenzoates / chemistry*
Mechanical Phenomena
Neuroprotective Agents* / chemical synthesis
Neuroprotective Agents* / chemistry
Neuroprotective Agents* / pharmacology
Oxidation-Reduction / drug effects

Substances

Antioxidants
Biocompatible Materials
Hydrogels
Hydroxybenzoates
Neuroprotective Agents
carboxymethyl-chitosan
protocatechuic acid
Chitosan