Synthesis of catechol and thiol containing compound for developing dental adhesive mimicking mussel adhesive protein

Abstract

Two key mechanisms among many adhesion forms known from mussel are cross-linking of DOPA with substrate and redox reactions of thiol that control activity of DOPA. DOPA can adhere on several surfaces via not only coordination but also redox reaction of thiol, which maintains unique property, adhesiveness, of catechol. Inspired from this, a compound containing catechol and thiol in one molecule was successfully synthesized. According to the result of degree of conversion measurement, thiol enhanced polymerization of methacrylate by cross-linking each bond through thiol-ene reaction. And the developed adhesive even showed higher property than that of the standard when metal ion or oxidant was present. The compound of this work is mimicking Mfp-6 system which has not been tried before, and it might be applied into practical dental adhesive field.