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New insights into highly potent tyrosinase inhibitors based on 3-heteroarylcoumarins: Anti-melanogenesis and antioxidant activities, and computational molecular modeling studies

dc.contributor.authorPintus F.
dc.contributor.authorMatos M.J.
dc.contributor.authorVilar S.
dc.contributor.authorHripcsak G.
dc.contributor.authorVarela C.
dc.contributor.authorUriarte E.
dc.contributor.authorSantana L.
dc.contributor.authorBorges F.
dc.contributor.authorMedda R.
dc.contributor.authorDi Petrillo A.
dc.contributor.authorEra B.
dc.contributor.authorFais A.
dc.date.accessioned2020-09-02T22:25:51Z
dc.date.available2020-09-02T22:25:51Z
dc.date.issued2017
dc.identifier10.1016/j.bmc.2017.01.037
dc.identifier.citation25, 5, 1687-1695
dc.identifier.issn09680896
dc.identifier.urihttps://hdl.handle.net/20.500.12728/5811
dc.descriptionMelanogenesis is a physiological pathway for the formation of melanin. Tyrosinase catalyzes the first step of this process and down-regulation of its activity is responsible for the inhibition of melanogenesis. The search for molecules capable of controlling hyperpigmentation is a trend topic in health and cosmetics. A series of heteroarylcoumarins have been synthesized and evaluated. Compounds 4 and 8 exhibited higher tyrosinase inhibitory activities (IC50= 0.15 and 0.38 μM, respectively), than the reference compound, kojic acid (IC50= 17.9 μM). Compound 4 acts as competitive, while compound 8 as uncompetitive inhibitor of mushroom tyrosinase. Furthermore, compounds 2 and 8 inhibited tyrosinase activity and melanin production in B16F10 cells. In addition, compounds 2–4 and 8 proved to have an interesting antioxidant profile in both ABTS and DPPH radicals scavenging assays. Docking experiments were carried out in order to study the interactions between these heteroarylcoumarins and mushroom tyrosinase. © 2017 Elsevier Ltd
dc.language.isoen
dc.publisherElsevier Ltd
dc.subject3-Heteroarylcoumarins
dc.subjectB16F10 melanoma cells
dc.subjectMelanogenesis
dc.subjectTyrosinase inhibitors
dc.subject3 (4 bromothiophen 2 yl) 5,7 dihydroxycoumarin
dc.subject3 (4 bromothiophen 2 yl) 6 methoxycoumarin
dc.subject3 (4 bromothiophen 2 yl) 7 hydroxycoumarin
dc.subject3 (4 bromothiophen 2 yl) 7,8 dihydroxycoumarin
dc.subject3 (4 bromothiophen 2 yl) 8 hydroxycoumarin
dc.subject3 heteroarylcoumarin derivative
dc.subject5,7 dihydroxy 3 (thiophen 2 yl)coumarin
dc.subject6 hydroxy 3 (thiophen 2 yl)coumarin
dc.subject6 methoxy 3 (thiophen 2 yl)coumarin
dc.subject7 hydroxy 3 (thiophen 2 yl)coumarin
dc.subjectantioxidant
dc.subjectcoumarin derivative
dc.subjectkojic acid
dc.subjecttrolox C
dc.subjectunclassified drug
dc.subjectantioxidant
dc.subjectenzyme inhibitor
dc.subjectmelanin
dc.subjectmonophenol monooxygenase
dc.subjectABTS radical scavenging assay
dc.subjectanimal cell
dc.subjectantimelanogenesis activity
dc.subjectantioxidant activity
dc.subjectArticle
dc.subjectcontrolled study
dc.subjectDPPH radical scavenging assay
dc.subjectdrug activity
dc.subjectdrug design
dc.subjectdrug synthesis
dc.subjectEC50
dc.subjectIC50
dc.subjectlimit of quantitation
dc.subjectmolecular docking
dc.subjectmolecular model
dc.subjectmouse
dc.subjectnonhuman
dc.subjectanimal
dc.subjectantagonists and inhibitors
dc.subjectbiosynthesis
dc.subjectcarbon nuclear magnetic resonance
dc.subjectmass spectrometry
dc.subjectproton nuclear magnetic resonance
dc.subjecttumor cell line
dc.subjectAnimals
dc.subjectAntioxidants
dc.subjectCarbon-13 Magnetic Resonance Spectroscopy
dc.subjectCell Line, Tumor
dc.subjectEnzyme Inhibitors
dc.subjectMass Spectrometry
dc.subjectMelanins
dc.subjectMice
dc.subjectModels, Molecular
dc.subjectMolecular Docking Simulation
dc.subjectMonophenol Monooxygenase
dc.subjectProton Magnetic Resonance Spectroscopy
dc.titleNew insights into highly potent tyrosinase inhibitors based on 3-heteroarylcoumarins: Anti-melanogenesis and antioxidant activities, and computational molecular modeling studies
dc.typeArticle


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