Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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3D-QSAR Study of Melanin Inhibiting (S)-(+)-Decursin and its Analogues by Pharmacophore Mapping

  • Lee, Kyeong (College of pharmacy, Dongguk University) ;
  • Jung, Sang-Won (Department of Bioinformatics, Korea University) ;
  • Naik, Ravi (College of pharmacy, Dongguk University) ;
  • Cho, Art E. (Department of Bioinformatics, Korea University)
  • Received : 2011.09.30
  • Accepted : 2011.11.15
  • Published : 2012.01.20
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Abstract

The (S)-(+)-decursin and its analogues are reported as potent inhibitors of melanin production in B16 murine melanoma cells. In order to understand the factors responsible for potency as well as inhibition of potency of (S)-(+)-decursin and its analogues, three-dimensional quantitative structure-activity relationship (3D-QSAR) studies were performed. Since receptor structures are not available, a pharmacophore model was constructed. Using PHASE, we generated 3 different models and selected the seven-site model, which returned excellent statistical values ($r^2$ = 0.9127, $Q^2$ = 0.6878, Pearson-R = 0.9014). Using the generated pharmacophore model, we screened a natural products library and obtained 4'-epi-decursin as the most related compound. 4'-epidecursin is similar to (S)-(+)-decursin, but shows additional interaction possibilities with tyrosinase. The study thus sheds some light on possibility of developing more potent tyrosinase inhibitors.

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