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

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  • Lee Kun Ho
    Graduate School of East-West Medical Science, Kyung Hee University
  • Koketsu Mamoru
    Division of Instrumental Analysis, Life Science Research Laboratory, Gifu University
  • Choi Sang Yoon
    Korea Food Research Institute
  • Lee Kang Jin
    Graduate School of East-West Medical Science, Kyung Hee University
  • Lee Pyeongjae
    Rural Development Administration, National Institute of Agricultural Science and Technology, Korea
  • Ishihara Hideharu
    Department of Chemistry, Faculty of Engineering, Gifu University
  • Kim Sun Yeou
    Graduate School of East-West Medical Science, Kyung Hee University

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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.

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