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Mixed-Type Inhibition of Tyrosinase from Agaricus bisporus by Terephthalic Acid: Computational Simulations and Kinetics

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Abstract

Tyrosinase inhibition studies are needed due to the agricultural and medicinal applications. For probing effective inhibitors of tyrosinase, a combination of computational prediction and enzymatic assay via kinetics were important. We predicted the 3D structure of tyrosinase from Agaricus bisporus, used a docking algorithm to simulate binding between tyrosinase and terephthalic acid (TPA) and studied the reversible inhibition of tyrosinase by TPA. Simulation was successful (binding energies for Autodock4 = −1.54 and Fred2.0 = −3.19 kcal/mol), suggesting that TPA interacts with histidine residues that are known to bind with copper ions at the active site. TPA inhibited tyrosinase in a mixed-type manner with a K i  = 11.01 ± 2.12 mM. Measurements of intrinsic and ANS-binding fluorescences showed that TPA induced no changes in tertiary structure. The present study suggested that the strategy of predicting tyrosinase inhibition based on hydroxyl groups and orientation may prove useful for screening of potential tyrosinase inhibitors.

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Abbreviations

DOPA:

3,4-Dihydroxyphenylalanine

TPA:

Terephthalic acid

ANS:

1-Anilinonaphthalene-8-sulfonate

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Acknowledgments

This research was supported by Consultation Program funded by the Science and Technology Department of Zhejiang Province (2008C0200-2). Dr. Jun-Mo Yang was supported by the grants of the Korea Health 21 R&D Project (Ministry of Health, Welfare and Family Affairs, Republic of Korea, 01-PJ3-PG6-01GN12-0001 and A030003). Dr. Yong-Doo Park was supported by a grant from the project of Zhejiang Provincial Natural Science Foundation of China (Grant No. Y2091212).

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Authors and Affiliations

  1. College of Biological and Environmental Sciences, Zhejiang Wanli University, Ningbo, 315100, P. R. China

    Shang-Jun Yin, Yue-Xiu Si, Yong-Fu Chen & Guo-Ying Qian

  2. Zhejiang Provincial Key Laboratory of Applied Enzymology, Yangtze Delta Region Institute of Tsinghua University, Jiaxing, 314006, P. R. China

    Zhi-Rong Lü & Yong-Doo Park

  3. Korean BioInformation Center (KOBIC), Korea Research Institute of Bioscience and Biotechnology (KRIBB), Daejeon, 305-806, Korea

    Sangho Oh, Jinhyuk Lee & Sanghyuk Lee

  4. Ewha Research Center for Systems Biology and Division of Life and Pharmaceutical Sciences, Ewha Womans University, Seoul, 120-750, Korea

    Sanghyuk Lee

  5. Department of Dermatology, Samsung Medical Center, Sungkyunkwan University School of Medicine, Seoul, 135-710, Korea

    Jun-Mo Yang & Dong-Youn Lee

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  1. Shang-Jun Yin
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  2. Yue-Xiu Si
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  5. Zhi-Rong Lü
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  7. Jinhyuk Lee
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  8. Sanghyuk Lee
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  9. Jun-Mo Yang
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  10. Dong-Youn Lee
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  11. Yong-Doo Park
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Correspondence to Dong-Youn Lee or Yong-Doo Park.

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Yin, SJ., Si, YX., Chen, YF. et al. Mixed-Type Inhibition of Tyrosinase from Agaricus bisporus by Terephthalic Acid: Computational Simulations and Kinetics. Protein J 30, 273–280 (2011). https://doi.org/10.1007/s10930-011-9329-x

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  • DOI: https://doi.org/10.1007/s10930-011-9329-x

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