Antifouling Surface Coating on Various Substrates by Inducing Tyrosinase-Mediated Oxidation of a Tyrosine-Conjugated Sulfobetaine Derivative

Inspired by the melanogenesis occurring in nature, we report tyrosinase-mediated antifouling surface coating by synthesizing a tyrosine-conjugated sulfobetaine derivative (Tyr-SB). Synthetic Tyr-SB contains zwitterionic sulfobetaine and tyrosine, whose phenolic amine group acts as a dormant coating precursor. In contrast to catecholamine derivatives, tyrosine derivatives are stable against auto-oxidation and are enzymatically oxidized only in the presence of tyrosinase to initiate melanin-like oxidation. When the surface of interest was applied during the course of Tyr-SB oxidation, a superhydrophilic poly­(Tyr-SB) film was coated on the surfaces, thereby showing antifouling performance against proteins or adherent cells. Because the oxidation of Tyr-SB occurred under mild aqueous conditions (pH 6–7) without the use of any chemical oxidants, such as sodium periodate or ammonium persulfate, we anticipate that the coating method described herein will serve as a biocompatible tool in the field of biosensors, cell surface engineering, and medical devices, whose interfaces differ in chemistry.