Chem. Pharm. Bull., 53(7),747-749, July 2005

Regular Articles

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

Kun Ho LEE,^a Mamoru KOKETSU,^b Sang Yoon CHOI,^c Kang Jin LEE,^a Pyeongjae LEE,^d Hideharu ISHIHARA,^e and Sun Yeou KIM^*,a

^a Graduate School of East-West Medical Science, Kyung Hee University; Yongin 449-701, Korea: ^b Division of Instrumental Analysis, Life Science Research Laboratory, Gifu University; Gifu 501-1193, Japan: ^c Korea Food Research Institute; Songnam 463-746, Korea: ^d Rural Development Administration, National Institute of Agricultural Science and Technology; Suwon 441-857, Korea: and ^e Department of Chemistry, Faculty of Engineering, Gifu University; Gifu 501-1193, Japan. * To whom correspondence should be addressed. e-mail: sunnykim@khu.ac.kr

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.

Key words N-aryl S-alkylthiocarbamate; mushroom tyrosinase; diethyldithiocarbamate