Citation: TANG Haifeng, CUI Fengchao, LIU Lunyang, LI Yunqi. Insight into the Inhibitory Activities of Diverse Ligands for Tyrosinase Using Ligand- and Structure-based Approaches[J]. Chinese Journal of Applied Chemistry, ;2018, 35(7): 788-794. doi: 10.11944/j.issn.1000-0518.2018.07.170332 shu

Insight into the Inhibitory Activities of Diverse Ligands for Tyrosinase Using Ligand- and Structure-based Approaches

TANG Haifeng ^a,b,c ,
CUI Fengchao ^a,, ,
LIU Lunyang ^a,c ,
LI Yunqi ^a,,

a.
Key Laboratory of Synthetic Rubber, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, China
b.
School of Life Science, Jilin University, Changchun 130012, China
c.
University of Chinese Academy of Sciences, Beijing 100049, China

Corresponding author: CUI Fengchao, fccui@ciac.ac.cn LI Yunqi, yunqi@ciac.ac.cn
Received Date: 12 September 2017
Revised Date: 25 October 2017
Accepted Date: 10 January 2018

Fund Project: One Hundred Person Project of the Chinese Academy of Science, and the China Postdoctoral Science Foundation 2014M561310the National Natural Science Foundation of China 21374117Supported by the National Natural Science Foundation of China(No.21374117, No.21504092), One Hundred Person Project of the Chinese Academy of Science, and the China Postdoctoral Science Foundation(No.2014M561310)the National Natural Science Foundation of China 21504092

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The use of variant inhibitors to regulate the bioactivities of tyrosinase, which is the key enzyme in charge of the production of melanin and pigments, is a long-standing approach to design cosmetic and pharmaceutical products. The quantitative description of the structure-activity relationship of tyrosinase inhibitors is still unclear. In this study, we constructed descriptive models by integrating ligand-and structure-based approaches for such purpose. They provide correlation coefficients of 0.961 for implicit models and 0.775 for explicit model, respectively, to descript the activities of three tea polyphenols with the tyrosinase inhibitory activity order of (-)-Epicatechin gallate(ECG) > (-)-Epigallocatechin gallate(EGCG) > Gallic acid(G). As revealing from the descriptive models, entropy loss is more important than other features for determining inhibitory activity and thus the tyrosinase-ECG complex with the fewer conformational entropy loss has the strongest inhibitory activity in vitro among the four tea polyphenols. Moreover, residues including His57, His201, Asn202, His205 Glu192 and Val215 are the core of active sites in tyrosinase, and stabilize the tyrosinase-inhibitor complex by van der Waals and hydrogen bonding interactions.
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