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http://dx.doi.org/10.3839/jabc.2010.040

3D-QSARs analyses for Tyrosinase Inhibitory Activity of 2-Phenyl-1,4-benzopyrone (Flavones) Analogues and Molecular Docking  

Park, Joon-Ho (Department of Biology, Queen's University Kingston)
Sung, Nack-Do (Department of Applied Biology and Chemistry, College of Agriculture and Life Science, Chungnam National University)
Publication Information
Journal of Applied Biological Chemistry / v.53, no.4, 2010 , pp. 225-231 More about this Journal
Abstract
To understand the inhibitory activity with changing hydroxyl substituents ($R_l-R_9$) of polyhydroxy substituted 2-phenyl-l,4-benzopyrone analogues (1-25) against tyrosinase (PDB ID: oxy-form; 1WX2), molecular docking and the three dimensional quantitative structure-activity relationships (3D-QSARs: Comparative molecular field analysis (CoMFA) & Comparative molecular similarity indices analysis (CoMSIA)) were studied quantitatively. The statistically best models were CoMFA 1 and CoMSIA 1 model from the results. The optimized CoMSIA 1 model with the sensitivity of the perturbation and the prediction produced ($dq^2=1.009 & $q^2$=0.51l) by a progressive scrambling analysis were not dependent on chance correlation. The inhibitory activities with optimized CoMSIA 1 model were dependent upon electrostatic factor (51.4%) of substrate molecules. Contour mapping the 3D-QSAR models to the active site of tyrosinase provides new insight into the interaction between tyrosinase as receptor and 2-phenyl-l,4-benzopyrone analogues as inhibitor. Therefore, the results will he able to apply to the optimization of a new potent tyrosinase inhibitors.
Keywords
2-phenyl-l,4-benzopyrone (Flavones) analogues; 3D-QSARs (CoMFA & CoMSIA); molecular docking; tyrosinase inhibition;
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