Molecular docking and biological evaluation of hydroxy-substituted (Z)-3-benzylideneindolin-2-one chalcones for the lead identification as tyrosinase inhibitors

被引：4

作者：

Suthar, Sharad Kumar ^{[1
]}

Aggarwal, Vaibhav ^{[1
]}

Chauhan, Monika ^{[1
]}

Sharma, Ankesh ^{[1
]}

Bansal, Sumit ^{[1
]}

Sharma, Manu ^{[1
]}

机构：

[1] Jaypee Univ Informat Technol, Dept Pharm, Waknaghat 173234, Himachal Prades, India

来源：

MEDICINAL CHEMISTRY RESEARCH | 2015年 / 24卷 / 03期

关键词：

Tyrosinase; Melanization; (Z)-3-Benzylideneindolin-2-one chalcones; Molecular docking studies; DERIVATIVES; DISCOVERY;

D O I：

10.1007/s00044-014-1225-4

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The increased cases of hyperpigmentation and other related dermatological problems in human beings have led to the development of a number of tyrosinase inhibitors. In the present study, we have used a docking algorithm to simulate binding between tyrosinase and hydroxy-substituted (Z)-3-benzylideneindolin-2-one chalcones and studied the inhibition of tyrosinase. The results of virtual screening studies indicated that the estimated free energy of binding of all the docked ligands ranged between -8.08 and -4.27 kcal/mol, while their estimated inhibition constants (Ki) were found to be between 1.20 and 736.75 A mu M. Among all the compounds docked, 2,4,6-trihydroxy-substituted chalcone (11) showed the lowest estimated free energy of binding followed by dihydroxy and monohydroxy-substituted analogs. In the in vitro tyrosinase inhibition assay, 11 displayed an IC50 of 46.26 A mu M. Moreover, in ADMET study, 11 was found to be safe and non-toxic. The present study suggested that the strategy of predicting tyrosinase inhibition based on hydroxy-substituted (Z)-3-benzylideneindolin-2-one chalcones and their orientation would be useful for developing novel potent tyrosinase inhibitors.

引用

页码：1331 / 1341

页数：11

共 32 条

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Ran, Yan ;

Pei, Heying ;

Shao, Mingfeng ;

Chen, Lijuan .

CHEMICAL BIOLOGY & DRUG DESIGN, 2016, 87 (02) :290-295

[32] Identification of new 5-(2,6-dichlorophenyl)-3-oxo-2,3-dihydro-5H-thiazolo[3,2-a] pyrimidine-7-carboxylic acids as p38α MAPK inhibitors: Design, synthesis, antitumor evaluation, molecular docking and in silico studies [J].

El-Wakil, Marwa H. ;

El-Dershaby, Hadeel A. ;

Ghazallah, Rasha A. ;

El-Yazbi, Amira F. ;

Abd El-Razik, Heba A. ;

Soliman, Farid S. G. .

BIOORGANIC CHEMISTRY, 2024, 145

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