Biological interactions of fluorinated chalcones: Stimulation of tyrosinase activity and binding to bovine serum albumin

Chaves, Otávio Augusto; Barros, Leonardo Santos de; Oliveira, Márcia C.C. de; Sant’Anna, Carlos Maurício R.; Ferreira, Aurélio B. B.; Silva, Francisco Assis da; Cesarín-Sobrinho, Darí; Netto‐Ferreira, José Carlos

doi:10.1016/j.jfluchem.2017.04.007

Cited by 34 publications

(12 citation statements)

References 46 publications

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“…The mechanism of fluorescence quenching was usually classified as static quenching and dynamic quenching 19 . The fluorescence data were determined using the Stern–Volmer equation to distinguish these two quenching mechanisms.…”

Section: Resultsmentioning

confidence: 99%

Kinetic and computational molecular docking simulation study of novel kojic acid derivatives as anti-tyrosinase and antioxidant agents

Chen

Zhang

et al. 2019

Journal of Enzyme Inhibition and Medicinal Chemistry

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The novel kojic acid derivatives KAD1 and KAD2 have been demonstrated that they exhibited potent antimelanogenesis activity in our previous report. In this study, we further study the inhibitory mechanism on mushroom tyrosinase. The inhibitory types of both KADs on diphenolase were classified as mixed type based on the results of the kinetic model. The interaction between KADs and tyrosinase was illustrated by fluorescence quenching, molecular docking and copper chelate activity. The KADs were also evaluated with respect to their antioxidant activities by DPPH and ABTS þ assays. The results showed that KADs have more potent antioxidant activities than kojic acid. Our study could provide new ideas for the development of new anti-tyrosinase and antioxidant agents.

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Section: Resultsmentioning

confidence: 99%

Kinetic and computational molecular docking simulation study of novel kojic acid derivatives as anti-tyrosinase and antioxidant agents

Chen

Zhang

et al. 2019

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…The reason for the weak activity may be that lithospermic acid and salvianolic acid A do not combine with the active amino acid residues (such as GLU322 and THR324) or do not act on the active center (Cu 2+ ) of tyrosinase. As tyrosinase is a copper-containing enzyme, it is expected that potential tyrosinase inhibitors should show high binding affinity for copper ions [ 26 ].…”

Section: Resultsmentioning

confidence: 99%

Screening and Characterizing Tyrosinase Inhibitors fromSalvia miltiorrhizaandCarthamus tinctoriusby Spectrum-Effect Relationship Analysis and Molecular Docking

Wang

Zhang

et al. 2018

Journal of Analytical Methods in Chemistry

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Tyrosinase (TYR) is a rate-limiting enzyme in the synthesis of melanin, while direct TYR inhibitors are a class of important clinical antimelanoma drugs. This study established a spectrum-effect relationship analysis method and high-performance liquid chromatography-mass spectrometry (LC-MS) analysis method to screen and identify the active ingredients that inhibited TYR in Salvia miltiorrhiza–Carthamus tinctorius (Danshen–Honghua, DH) herbal pair. Seventeen potential active compounds (peaks) in the extract of DH herbal pair were predicted, and thirteen of them were tentatively identified by LC-MS analysis. Furthermore, TYR inhibitory activities of five pure compounds obtained from the DH herbal pair were validated in the test in which kojic acid served as a positive control drug. Among them, three compounds including protocatechuic aldehyde, hydroxysafflor yellow A, and tanshinone IIA were verified to have high TYR inhibitory activity (IC50 value of 455, 498, and 1214 μM, resp.) and bind to the same amino acid residues in TYR catalytic pocket according to the results of the molecular docking test. However, the other two compounds lithospermic acid and salvianolic acid A had a weak effect on TYR, as they do not combine with the active amino acid residues or act on the active center of TYR. Therefore, the developed methods (spectrum-effect relationship analysis and molecular docking) could be used to effectively screen TYR inhibitors in complex mixtures such as natural products.

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“…According to the new classification of polyphenols (Phenol-Explorer Version 3.6 database, ), chalcones are considered as a subclass of flavonoids [ 47 ]. In addition to the anti-tyrosinase property [ 40 , 48 , 49 ], chalcones and their derivatives have been reported to possess various biological and pharmacological activities including anti-inflammatory, antipyretic, analgesic, bactericidal, insecticidal, anti-fungal anticancer and antioxidant [ 50 ]. Flavokawains used in the study are a class of chalcones found on kava plants, which were synthesized by base catalyzed Claisen–Schmidt condensation ( Figure 7 A).…”

Section: Discussionmentioning

confidence: 99%

Melanogenic Inhibition and Toxicity Assessment of Flavokawain A and B on B16/F10 Melanoma Cells and Zebrafish (Danio rerio)

et al. 2020

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Excessive production of melanin implicates hyperpigmentation disorders. Flavokawain A (FLA) and flavokawain B (FLB) have been reported with anti-melanogenic activity, but their melanogenic inhibition and toxicity effects on the vertebrate model of zebrafish are still unknown. In the present study, cytotoxic as well as melanogenic effects of FLA and FLB on cellular melanin content and tyrosinase activity were evaluated in α-MSH-induced B16/F10 cells. Master regulator of microphthalmia-associated transcription factor (Mitf) and the other downstream melanogenic-related genes were verified via quantitative real time PCR (qPCR). Toxicity assessment and melanogenesis inhibition on zebrafish model was further observed. FLA and FLB significantly reduced the specific cellular melanin content by 4.3-fold and 9.6-fold decrement, respectively in α-MSH-induced B16/F10 cells. Concomitantly, FLA significantly reduced the specific cellular tyrosinase activity by 7-fold whilst FLB by 9-fold. The decrement of melanin production and tyrosinase activity were correlated with the mRNA suppression of Mitf which in turn down-regulate Tyr, Trp-1 and Trp-2. FLA and FLB exhibited non-toxic effects on the zebrafish model at 25 and 6.25 µM, respectively. Further experiments on the zebrafish model demonstrated successful phenotype-based depigmenting activity of FLA and FLB under induced melanogenesis. To sum up, our findings provide an important first key step for both of the chalcone derivatives to be further studied and developed as potent depigmenting agents.

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Biological interactions of fluorinated chalcones: Stimulation of tyrosinase activity and binding to bovine serum albumin

Cited by 34 publications

References 46 publications

Kinetic and computational molecular docking simulation study of novel kojic acid derivatives as anti-tyrosinase and antioxidant agents

Kinetic and computational molecular docking simulation study of novel kojic acid derivatives as anti-tyrosinase and antioxidant agents

Screening and Characterizing Tyrosinase Inhibitors fromSalvia miltiorrhizaandCarthamus tinctoriusby Spectrum-Effect Relationship Analysis and Molecular Docking

Melanogenic Inhibition and Toxicity Assessment of Flavokawain A and B on B16/F10 Melanoma Cells and Zebrafish (Danio rerio)

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