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

  title={Inhibition of tyrosinase by 4H‐chromene analogs: Synthesis, kinetic studies, and computational analysis},
  author={Edikarlos Macedo Brasil and Luciana Morais Canavieira and {\'E}rica T C Cardoso and Edilene Oliveira Silva and Jer{\^o}nimo Lameira and Jos{\'e} Luiz M. Nascimento and Vera L{\'u}cia Eifler-Lima and Barbarella de Matos Macchi and Dharmarajan Sriram and Paul V. Bernhardt and Jos{\'e} Rog{\'e}rio Ara{\'u}jo Silva and Craig M. Williams and Cl{\'a}udio Nahum Alves},
  journal={Chemical Biology \& Drug Design},
  pages={804 - 810}
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… 
Experimental and theoretical approaches for the development of 4H-Chromene derivatives as inhibitors of tyrosinase
This study evaluated a series of dihydropyrano[3,2-b] chromenedione and 1,8-dioxooctahydroxanthene derivatives and suggested that these synthetic heterocyclic compounds may behave as competitive inhibitors for the L-DOPA binding site of the TYR.
Analysis of Kojic Acid Derivatives as Competitive Inhibitors of Tyrosinase: A Molecular Modeling Approach
The results suggest that these kojic acid derivatives could be potent competitive inhibitors of the natural substrates of L-DOPA and L-tyrosine in melanogenesis and melanogenesis respectively.
Theoretical Studies of Cyanophycin Dipeptides as Inhibitors of Tyrosinases
The AlphaFold structure of human tyrosinase and the previous model were compared and a new set of cyanophycin-derived dipeptides was evaluated as potential inhibitors; Aspartate–glutamate showed the strongest interaction and was chosen as a leading compound for future studies.
Investigation of tyrosinase inhibition by some 1,2,4 triazole derivative compounds: in vitro and in silico mechanisms
It is suggested that B9 compound is a potential tyrosinase inhibitor, and is an alternative method for keeping insects under control.
The Role of Anthocyanins, Deoxyanthocyanins and Pyranoanthocyanins on the Modulation of Tyrosinase Activity: An In Vitro and In Silico Approach
Assessment of tyrosinase inhibitory activity of eight purified compounds with a variable degree of structural complexity support the applicability of these compounds as pigmentation modulators.
Three-Component Synthesis of 2-Amino-3-cyano-4H-chromenes, In Silico Analysis of Their Pharmacological Profile, and In Vitro Anticancer and Antifungal Testing
Compounds 4a–o and 6a–h are good candidates for further research, having demonstrated their dual inhibition of enzymes that participate in the growth of cancer and fungal cells.
Pellucidin A promotes antinociceptive activity by peripheral mechanisms inhibiting COX-2 and NOS: In vivo and in silico study
In vivo and in silico results show that Pellucidin A’s mechanism of action in the inflammatory pain occurs most likely through interaction with the nitric oxide (NO) pathway, and demonstrates that the antinociceptive activities of Pellucin A operate under mechanism(s) of peripheral action, involving inflammatory mediators.


Molecular design of tyrosinase inhibitors: A critical review of promising novel inhibitors from synthetic origins
The importance and applications of the recently designed synthetic tyrosinase inhibitors from the and other leading laboratories of the world, which have been published in recent years are reviewed.
Tyrosinase inhibitors from natural and synthetic sources: structure, inhibition mechanism and perspective for the future
  • Y. Kim, H. Uyama
  • Chemistry, Medicine
    Cellular and Molecular Life Sciences CMLS
  • 2005
This article overviews the various inhibitors obtained from natural and synthetic sources with their industrial importance, and examines the role of tyrosinase in melanin biosynthesis and its role in dermatological disorders.
Tyrosinase inhibition by isophthalic acid: kinetics and computational simulation.
Suicide inactivation of the diphenolase and monophenolase activities of tyrosinase
Kinetic analysis of the proposed mechanism during the transition phase provides explicit analytical expressions for the concentrations of o‐quinone versus time and one possible application of this property could be the use of these suicide substrates as skin depigmenting agents.
Combined Kinetic Studies and Computational Analysis on Kojic Acid Analogs as Tyrosinase Inhibitors
The results showed that the electrostatic binding free energy are correlated with values of constant inhibition (r2 = 0.97) and could contribute to future studies of this important system and eventually facilitate development of tyrosinase inhibitors.
An Updated Review of Tyrosinase Inhibitors
This article surveys tyrosinase inhibitors newly discovered from natural and synthetic sources and the inhibitory strength is compared with that of a standard inhibitor, kojic acid, and their inhibitory mechanisms are discussed.