Bioorthogonal Functionalization of Material Surfaces with Bioactive Molecules

Abstract

The ability to control and modify the bioactivity of surfaces is pivotal to the success of many medical devices. A biocompatible and bioorthogonal method to functionalize surfaces with a wide variety of bioactive molecules is an important tool for enabling innovative biotechnology and medical applications. We report herein a novel, catecholamine-based surface functionalization method that is chemoselective and free of a metal catalyst. This method utilizes the ligation between a coating formed from the tyrosinase-catalyzed polymerization of a tetrazine-containing catecholamine and one or more strained alkene-containing molecules of interest. The process is achieved under conditions ideal for biological applications. Using this method, we graft surfaces with a variety of active molecules, including a small molecule fluorophore, enzymes, and a cyclic peptide with the RGD motif, and demonstrate the maintenance of their activity on the surface. Additionally, we establish the cytocompatibility of grafted ECM-mimicking surfaces with fibroblasts and show improved cell adhesion and cytoskeletal organization.