Potent Inhibitory Effects of N-Aryl S-Alkylthiocarbamate Derivatives on the Dopa Oxidase Activity of Mushroom Tyrosinase

Abstract

This study reports the potent inhibitory effect of N-aryl S-alkylthiocarbamate derivatives on mushroom tyrosinase (MT) activity. N-Aryl S-alkylthiocarbamate derivatives were found to exhibit a potent inhibitory effect on the dopa (3,4-dihydroxyphenylalanine) oxidase activity of mushroom tyrosinase. Most of the N-aryl S-alkylthiocarbamate derivatives (compounds from A to J) exhibited higher inhibitory effects than kojic acid (IC₅₀=318 μm), a well known tyrosinase inhibitor. Tyrosinase was the most inhibited by S-phenetyl N-phenylthiocarbamate (compound E, IC₅₀=7.25 μM), and this inhibition was 44 times stronger than that of kojic acid. Compound E exhibited 95.0% of inhibition at 100 μM. A kinetic study of MT inhibition by compound E using the Lineweaver–Burk plots analysis was performed. And the kinetics profiles observed suggest that compound E competitively inhibits MT.