Dextran hydrogels via disulfide-containing Schiff base formation: Synthesis, stimuli-sensitive degradation and release behaviors

Hongying Su; Rong Zheng; Linrui Jiang; Ni Zeng; Kun Yu; Yunfei Zhi; Shaoyun Shan

doi:10.1016/j.carbpol.2021.118085

Dextran hydrogels via disulfide-containing Schiff base formation: Synthesis, stimuli-sensitive degradation and release behaviors

Carbohydr Polym. 2021 Aug 1:265:118085. doi: 10.1016/j.carbpol.2021.118085. Epub 2021 Apr 16.

Authors

Hongying Su¹, Rong Zheng², Linrui Jiang², Ni Zeng², Kun Yu², Yunfei Zhi², Shaoyun Shan²

Affiliations

¹ Faculty of Chemical Engineering, Kunming University of Science and Technology, 727 South Jingming Road, Kunming, 650500, China. Electronic address: hongyingsu@kust.edu.cn.
² Faculty of Chemical Engineering, Kunming University of Science and Technology, 727 South Jingming Road, Kunming, 650500, China.

PMID: 33966849
DOI: 10.1016/j.carbpol.2021.118085

Abstract

Dextran hydrogels (Dex-SS) containing both disulfide and Schiff base bonds were developed via facile method based on the dextran oxidation and subsequent formation of Schiff base linkages between polyaldehyde dextran and cystamine, denoted as the disulfide-containing Schiff base reactions. Results of rheology, swelling and ¹³C CP/MAS NMR study indicated that cross-linking degree of Dex-SS hydrogels depended strongly on the molar ratio of -CHO/-NH₂. Acidic and reductive (GSH) environment sensitive degradation behaviors of Dex-SS hydrogels were then evidenced by SEM, rheology study and Ellman's assay. Moreover, doxorubicin (DOX) was loaded into the hydrogel matrix and pH/GSH-responsive release behaviors were demonstrated. Cytocompatibility of Dex-SS hydrogel and effective cell uptake of released DOX was finally proved by transwell assay with HepG2 cells. Take advantages of the abundance of vicinal hydroxyl on a variety of polysaccharides, the disulfide-containing Schiff base reactions is considered as versatile method to develop stimuli-sensitive hydrogels for local drug delivery.

Keywords: (13)C CP/MAS NMR; Dextran; Doxorubicin; Ellman’s assay; Stimuli-sensitive hydrogel; Triggered drug release.