Potent inhibitory effects of N-aryl S-alkylthiocarbamate derivatives on the dopa oxidase activity of mushroom tyrosinase.
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 microM), a well known tyrosinase inhibitor. Tyrosinase was the most inhibited by S-phenetyl N-phenylthiocarbamate (compound E, IC50=7.25 microM), and this inhibition was 44 times stronger than that of kojic acid. Compound E exhibited 95.0% of inhibition at 100 microM. 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.
Lee
Kun Ho
KH
Graduate School of East-West Medical Science, Kyung Hee University, Yongin, Korea.
Koketsu
Mamoru
M
Choi
Sang Yoon
SY
Lee
Kang Jin
KJ
Lee
Pyeongjae
P
Ishihara
Hideharu
H
Kim
Sun Yeou
SY
D000363:Agaricales / Q000201:enzymology*; D004791:Enzyme Inhibitors / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors*; D013055:Spectrophotometry, Infrared; D013329:Structure-Activity Relationship; D013859:Thiocarbamates / Q000494:pharmacology*
D004791:Enzyme Inhibitors; D013859:Thiocarbamates; D014442:Monophenol Monooxygenase