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Kinetics and Computational Docking Studies on the Inhibition of Tyrosinase Induced by Oxymatrine

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Abstract

A combination of enzymatic inhibition kinetics and computational prediction was employed to search for an effective inhibitor of tyrosinase. We found that oxymatrine significantly inhibited tyrosinase, and that this reaction was not accompanied by detectable conformational changes. Kinetic analysis showed that oxymatrine reversibly inhibited tyrosinase in a mixed-type manner. Measurements of intrinsic and ANS-binding fluorescences showed that oxymatrine did not induce any conspicuous changes in the tertiary structure. We also conducted a docking simulation between tyrosinase and oxymatrine using two docking programs, Dock6.3 and AutoDock4.2 (binding energy was −118.81 kcal/mol for Dock6 and −8.04 kcal/mol for AutoDock4). The results also suggested that oxymatrine interacts mostly with the residues of CYS83 and HIS263 in the active site of tyrosinase. This strategy of predicting tyrosinase inhibition by simulation of docking coupling with kinetics may prove useful in screening for potential tyrosinase inhibitors. Knowledge of tyrosinase inhibition can provide medical, cosmetic, and agricultural applications. Our study suggests that oxymatrine is an important agent for various applications related to pigment formation.

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Abbreviations

DOPA:

3,4-Dihydroxyphenylalanine

ANS:

1-Anilinonaphthalene-8-sulfonate

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Acknowledgments

Dr. Xiao-Xia Liu was supported by the National Natural Science Foundation of China (No. 31100053) and Zhejiang Science & Technology Innovation Team Project (2012R10012-08). Dr. Hong-Yan Han was supported by the National Natural Science Foundation of China (No. 81071306). Dr. Hai-Meng Zhou was supported by a grant from the 624 project supported by Zhejiang leading team of Science & Technology innovation (Team No. 2010R50019).

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Authors and Affiliations

  1. College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing, 314001, People’s Republic of China

    Xiao-Xia Liu, Shi-Qing Sun, Yu-Jie Wang, Wei Xu & Yi-Fang Wang

  2. Molecular Inflammation Research Center for Aging Intervention (MRCA), College of Pharmacy, Pusan National University, Busan, 609-735, Korea

    Daeui Park

  3. Zhejiang Provincial Key Laboratory of Applied Enzymology, Yangtze Delta Region Institute of Tsinghua University, Jiaxing, 314006, People’s Republic of China

    Hai-Meng Zhou

  4. School of Biology and Basic Medical Sciences, Soochow University, Suzhou, 215123, People’s Republic of China

    Hong-Yan Han

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  1. Xiao-Xia Liu
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  2. Shi-Qing Sun
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  4. Wei Xu
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Correspondence to Xiao-Xia Liu or Hong-Yan Han.

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Liu, XX., Sun, SQ., Wang, YJ. et al. Kinetics and Computational Docking Studies on the Inhibition of Tyrosinase Induced by Oxymatrine. Appl Biochem Biotechnol 169, 145–158 (2013). https://doi.org/10.1007/s12010-012-9960-9

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  • DOI: https://doi.org/10.1007/s12010-012-9960-9

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