Synthesis and characterization of protocatechuic acid grafted carboxymethyl chitosan with oxidized sodium alginate hydrogel through the Schiff's base reaction

Abstract

Excessive accumulation of free radicals is closely related to the occurrence and development of various neurodegenerative diseases. In this study, a novel protocatechuic acid grafted carboxymethyl chitosan with oxidized sodium alginate (PCA-g-CMCS/OSA) hydrogel was developed to maintain the oxidation-antioxidation balance activities. By optimizing the pH-soluble range (pH > 6.4) of CMCS, PCA was grafted onto CMCS skeleton via EDC/NHS, and then conjugated with aldehyde group of OSA to form Schiff's base hydrogel at physiological temperature. The gelation time can be adjusted rapidly within 1-3 min by controlling the content of OSA. The shaped hydrogel exhibited porous network structure with high porosity (>90 %), swelling ratio (2000-3000 %) and rheological property, which is beneficial to cell growth and proliferation. The conjugates preserved excellent DPPH and ABTS radicals scavenging abilities and adequate biodegradability within 5 weeks. Moreover, with the release of PCA monomer due to degradation of the PCA-g-CMCS/OSA, the hydrogel also exhibited excellent biocompatibility and protective effect on H₂O₂-induced oxidative damage in PC12 cells. These results suggested that the PCA-g-CMCS/OSA hydrogel would appear to be a more attractive candidate for potential biomedical applications such as antioxidant drug release and tissue engineering implant material.

Keywords: Carboxymethyl chitosan; Hydrogel; Oxidized sodium alginate; Protocatechuic acid; Schiff's base reaction.