Inhibition of Tyrosinase by 4H-Chromene Analogues: Synthesis, Kinetic Studies and Computational Analysis

Brasil, Edikarlos M., Canavieira, Luciana M., Cardoso, Érica T. C., Silva, Edilene O., Lameira, Jeronimo, Nascimento, Jose L. M., Eifler-Lima, Vera L., de Matos Macchi, Barbarella, Sriram, Dharmarajan, Bernhardt, Paul V., Silva, Jose Rogerio Araujo, Williams, Craig M. and Alves, Claudio N. (2017) Inhibition of Tyrosinase by 4H-Chromene Analogues: Synthesis, Kinetic Studies and Computational Analysis. Chemical Biology and Drug Design, . doi:10.1111/cbdd.13001

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Author Brasil, Edikarlos M.
Canavieira, Luciana M.
Cardoso, Érica T. C.
Silva, Edilene O.
Lameira, Jeronimo
Nascimento, Jose L. M.
Eifler-Lima, Vera L.
de Matos Macchi, Barbarella
Sriram, Dharmarajan
Bernhardt, Paul V.
Silva, Jose Rogerio Araujo
Williams, Craig M.
Alves, Claudio N.
Title Inhibition of Tyrosinase by 4H-Chromene Analogues: Synthesis, Kinetic Studies and Computational Analysis
Journal name Chemical Biology and Drug Design   Check publisher's open access policy
ISSN 1747-0285
Publication date 2017-04-08
Year available 2017
Sub-type Article (original research)
DOI 10.1111/cbdd.13001
Open Access Status File (Author Post-print)
Total pages 7
Place of publication Hoboken, NJ United States
Publisher Wiley-Blackwell Publishing
Collection year 2018
Language eng
Abstract 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 Ki value of 4μM, 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.
Keyword Inhibitor
Kinetic assays
Kojic acid
Molecular modeling
Multicomponent reaction
Tyrosinase
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: HERDC Pre-Audit
School of Chemistry and Molecular Biosciences
 
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Created: Fri, 21 Apr 2017, 11:43:21 EST by Mrs Louise Nimwegen on behalf of School of Chemistry & Molecular Biosciences