Rapid in situ cross-linking of hydrogel adhesives based on thiol-grafted bio-inspired catechol-conjugated chitosan

Abstract

In this paper, a novel chitosan derivative, thiol-grafting bio-inspired catechol-conjugated chitosan was synthesized. The chemical structure of the synthesized catechol-conjugated chitosan was verified by 1H NMR, and its contents of thiol group and catechol group were determined by UV-vis spectrum. Four percent of catechol-conjugated chitosan aqueous solution could form hydrogels rapidly in situ in 1 min or less with the addition of sodium periodate. Rheological studies showed that the mechanical properties depend on the concentrations of catechol-conjugated chitosan and the molar ratio of sodium periodate to catechol groups. Additionally, the adhesive properties of the resulting adhesives were evaluated, and the adhesion strength of obtained adhesives was as high as 50 kPa because of the complex and multiple interactions, especially the anti-oxidation mechanism of thiol group. The in vitro cytotoxicity assays demonstrated an excellent biocompatibility of the catechol-conjugated chitosan hydrogels. Benefiting from the in situ fast cured, desired mechanical strength, biocompatibility and relatively high adhesion performance, these properties suggested that catechol-conjugated chitosan hydrogel adhesives have potential applications as tissue adhesive for soft tissues.