Inhibition of tyrosinase by 4H-chromene analogs: Synthesis, kinetic studies, and computational analysis

被引：16

作者：

Brasil, Edikarlos M. ^{[1
,2
]}

Canavieira, Luciana M. ^{[1
]}

Cardoso, Erica T. C. ^{[3
]}

Silva, Edilene O. ^{[4
]}

Lameira, Jeronimo ^{[1
,5
]}

Nascimento, Jose L. M. ^{[3
,5
]}

Eifler-Lima, Vera L. ^{[6
]}

Macchi, Barbarella M. ^{[3
,5
]}

Sriram, Dharmarajan ^{[7
]}

Bernhardt, Paul V. ^{[2
]}

Araujo Silva, Jose Rogerio ^{[1
]}

Williams, Craig M. ^{[2
]}

Alves, Claudio N. ^{[1
,5
]}

机构：

[1] Univ Fed Para, Lab Planejamento & Desenvolvimento Farmacos, Inst Ciencias Exactas & Nat, Belem, PA, Brazil

[2] Univ Queensland, Sch Chem & Mol Biosci, Brisbane, Qld, Australia

[3] Univ Fed Para, Lab Neuroquim Mol & Celular, Inst Ciencias Biol, Belem, PA, Brazil

[4] Univ Fed Para, Lab Biol Estrutural, Inst Ciencias Biol, Belem, PA, Brazil

[5] Univ Fed Para, Programa Posgrad Quim Med, Belem, PA, Brazil

[6] Univ Fed Rio Grande do Sul, Fac Farm, Porto Alegre, RS, Brazil

[7] Birla Inst Technol & Sci, Med Chem & Antimycobacterial Res Lab, Dept Pharm, Hyderabad, Andhra Pradesh, India

来源：

CHEMICAL BIOLOGY & DRUG DESIGN | 2017年 / 90卷 / 05期

基金：

澳大利亚研究理事会;

关键词：

inhibitor; kinetic assays; kojic acid; molecular modeling; multicomponent reaction; tyrosinase; MUSHROOM TYROSINASE; MOLECULAR DOCKING; KOJIC ACID; MECHANISM; DESIGN; SKIN; TROPOLONE; AGENT;

D O I：

10.1111/cbdd.13001

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Inhibition of mushroom tyrosinase was observed with synthetic dihydropyrano[3,2-b]chromenediones. Among them, DHPC04 displayed the most potent tyrosinase inhibitory activity with a K-i value of 4m, comparable to the reference standard inhibitor kojic acid. A kinetic study suggested that these synthetic heterocyclic compounds behave as competitive inhibitors for the L-DOPA binding site of the enzyme. Furthermore, molecular modeling provided important insight into the mechanism of binding interactions with the tyrosinase copper active site.

引用

页码：804 / 810

页数：7

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