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Inhibition of tyrosinase by 4H-chromene analogs: Synthesis, kinetic studies, and computational analysis.
Chem Biol Drug Des. 2017 Nov; 90(5):804-810.CB

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 4 μm, 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.

Authors+Show Affiliations

Laboratório de Planejamento e Desenvolvimento de Fármacos, Instituto de Ciências Exatas e Naturais, Universidade Federal do Pará, Belém, PA, Brazil. School of Chemistry and Molecular Biosciences, University of Queensland, Brisbane, Queensland, Australia.Laboratório de Planejamento e Desenvolvimento de Fármacos, Instituto de Ciências Exatas e Naturais, Universidade Federal do Pará, Belém, PA, Brazil.Laboratório de Neuroquímica Molecular e Celular, Instituto de Ciências Biológicas, Universidade Federal do Pará, Belém, PA, Brazil.Laboratório de Biologia Estrutural, Instituto de Ciências Biológicas, Universidade Federal do Pará, Belém, PA, Brazil.Laboratório de Planejamento e Desenvolvimento de Fármacos, Instituto de Ciências Exatas e Naturais, Universidade Federal do Pará, Belém, PA, Brazil. Programa de Pós-Graduação em Química Medicinal, Universidade Federal do Pará, Belém, PA, Brazil.Laboratório de Neuroquímica Molecular e Celular, Instituto de Ciências Biológicas, Universidade Federal do Pará, Belém, PA, Brazil. Programa de Pós-Graduação em Química Medicinal, Universidade Federal do Pará, Belém, PA, Brazil.Faculdade de Farmácia, Universidade Federal do Rio Grande do Sul, Porto Alegre, Rio Grande do Sul, Brazil.Laboratório de Neuroquímica Molecular e Celular, Instituto de Ciências Biológicas, Universidade Federal do Pará, Belém, PA, Brazil. Programa de Pós-Graduação em Química Medicinal, Universidade Federal do Pará, Belém, PA, Brazil.Medicinal Chemistry and Antimycobacterial Research Laboratory, Department of Pharmacy, Birla Institute of Technology and Science, Hyderabad, India.School of Chemistry and Molecular Biosciences, University of Queensland, Brisbane, Queensland, Australia.Laboratório de Planejamento e Desenvolvimento de Fármacos, Instituto de Ciências Exatas e Naturais, Universidade Federal do Pará, Belém, PA, Brazil.School of Chemistry and Molecular Biosciences, University of Queensland, Brisbane, Queensland, Australia.Laboratório de Planejamento e Desenvolvimento de Fármacos, Instituto de Ciências Exatas e Naturais, Universidade Federal do Pará, Belém, PA, Brazil. Programa de Pós-Graduação em Química Medicinal, Universidade Federal do Pará, Belém, PA, Brazil.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

28390091

Citation

Brasil, Edikarlos M., et al. "Inhibition of Tyrosinase By 4H-chromene Analogs: Synthesis, Kinetic Studies, and Computational Analysis." Chemical Biology & Drug Design, vol. 90, no. 5, 2017, pp. 804-810.
Brasil EM, Canavieira LM, Cardoso ÉTC, et al. Inhibition of tyrosinase by 4H-chromene analogs: Synthesis, kinetic studies, and computational analysis. Chem Biol Drug Des. 2017;90(5):804-810.
Brasil, E. M., Canavieira, L. M., Cardoso, É. T. C., Silva, E. O., Lameira, J., Nascimento, J. L. M., Eifler-Lima, V. L., Macchi, B. M., Sriram, D., Bernhardt, P. V., Silva, J. R. A., Williams, C. M., & Alves, C. N. (2017). Inhibition of tyrosinase by 4H-chromene analogs: Synthesis, kinetic studies, and computational analysis. Chemical Biology & Drug Design, 90(5), 804-810. https://doi.org/10.1111/cbdd.13001
Brasil EM, et al. Inhibition of Tyrosinase By 4H-chromene Analogs: Synthesis, Kinetic Studies, and Computational Analysis. Chem Biol Drug Des. 2017;90(5):804-810. PubMed PMID: 28390091.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Inhibition of tyrosinase by 4H-chromene analogs: Synthesis, kinetic studies, and computational analysis. AU - Brasil,Edikarlos M, AU - Canavieira,Luciana M, AU - Cardoso,Érica T C, AU - Silva,Edilene O, AU - Lameira,Jerônimo, AU - Nascimento,José L M, AU - Eifler-Lima,Vera L, AU - Macchi,Barbarella M, AU - Sriram,Dharmarajan, AU - Bernhardt,Paul V, AU - Silva,José Rogério Araújo, AU - Williams,Craig M, AU - Alves,Cláudio N, Y1 - 2017/06/12/ PY - 2016/10/07/received PY - 2017/04/03/revised PY - 2017/04/04/accepted PY - 2017/4/9/pubmed PY - 2017/11/14/medline PY - 2017/4/9/entrez KW - inhibitor KW - kinetic assays KW - kojic acid KW - molecular modeling KW - multicomponent reaction KW - tyrosinase SP - 804 EP - 810 JF - Chemical biology & drug design JO - Chem Biol Drug Des VL - 90 IS - 5 N2 - 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 4 μm, 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. SN - 1747-0285 UR - https://www.unboundmedicine.com/medline/citation/28390091/Inhibition_of_tyrosinase_by_4H_chromene_analogs:_Synthesis_kinetic_studies_and_computational_analysis_ L2 - https://doi.org/10.1111/cbdd.13001 DB - PRIME DP - Unbound Medicine ER -