Resveratrol as a kcat type inhibitor for tyrosinase: Potentiated melanogenesis inhibitor

Satooka, Hiroki; Kubo, Isao

doi:10.1016/j.bmc.2011.11.030

Cited by 62 publications

(54 citation statements)

References 40 publications

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“…Because tyrosinase is produced only by melanoma cells, tyrosinase inhibitors also have high specificity for melanogenic cells without other adverse effects. Despite reports on a large number of tyrosinase inhibitors, only a few are used in cosmetic and medicinal products due to their cytotoxicity, and lack of selectivity and stability (Karioti et al 2007;Tocco et al 2009;Satooka and Kubo 2012). Thus, it is necessary to develop new tyrosinase inhibitors without such limitations.…”

Section: Introductionmentioning

confidence: 96%

Inhibition of melanogenesis by 2-[4-(5-chlorobenzo[d]thiazol-2-yl)phenoxy]-2-methylpropanoic acid (MHY908)

et al. 2014

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Tyrosinase inhibitors might have potential use in cosmetic and medicinal products for the prevention of pigmentation disorders. However, only a few inhibitors are currently used due to their cytotoxicity, and lack of selectivity and stability. In this study, we synthesized several tyrosinase inhibitors and investigated their activity. To investigate the action of 2-[4-(5-chlorobenzo[d]thiazol-2-yl)phenoxy]-2-methylpropanoic acid (MHY908) specifically in the inhibition of melanogenesis, a mushroom tyrosinase activity assay was performed. We confirmed the inhibitory effect of MHY908 at various melanin concentrations using α-MSH-induced melanoma cells. Our results indicate that MHY908 potently inhibited mushroom tyrosinase activity (IC50 = 8.19 μM) in a dose-dependent manner. Through a docking simulation, we also analyzed its binding mode to inhibit tyrosinase activity. MHY908 also decreased melanin synthesis without inducing cytotoxicity. These results suggest that MHY908 is a good candidate for prevention and treatment of pigmentation disorders.

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Section: Introductionmentioning

confidence: 96%

Inhibition of melanogenesis by 2-[4-(5-chlorobenzo[d]thiazol-2-yl)phenoxy]-2-methylpropanoic acid (MHY908)

et al. 2014

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“…The substances in this drug class act as competitive inhibitors of tyrosinase, in the presence of tyrosine and L -DOPA. After undergoing the enzymatic reaction, its metabolites act as noncompetitive inhibitors of tyrosinase, considering the substrate L -DOPA [13,28]. Furthermore, an investigation using B16-F10 murine melanoma cells showed cellular melanin production was significantly suppressed by resveratrol without any cytotoxicity up to 200 μM [28].…”

Section: Introductionmentioning

confidence: 99%

“…However, some studies have demonstrated that resveratrol does not inhibit the synthesis of melanin to such a degree that enables it to be utilized alone as skin whitening agent in pharmaceutical formulations, and so its use as a coadjuvant in hyperpigmentation treatments is suggested [13,28]. …”

Section: Introductionmentioning

confidence: 99%

Inhibitory Effects of Resveratrol Analogs on Mushroom Tyrosinase Activity

et al. 2012

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Skin pigmentation disorders typically involve an overproduction or uneven distribution of melanin, which results in skin spots. Resveratrol can inhibit tyrosinase, the active enzyme in the synthesis of melanin, but it does not inhibit the synthesis of melanin to an extent that enables its use alone as a skin whitening agent in pharmaceutical formulations, so its use as a coadjuvant in treatment of hyperpigmentation is suggested. Six resveratrol analogs were tested for tyrosinase inhibitory activity in vitro. Among the analogs tested, compound D was the most powerful tyrosinase inhibitor (IC50 = 28.66 µg/mL), two times more active than resveratrol (IC50 = 57.05 µg/mL), followed by the analogs A, E, B, F and C, respectively. This demonstrated that the hydroxylation at C4' on the phenolic ring was the molecular modification with most importance for the observed activity.

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“…These UVvis observations are consistent with the tyrosinase-catalyzed oxidation of resveratrol. [ 33,34 ] To demonstrate that the product generated from the tyrosinase reaction with resveratrol grafts to the chitosan fi lm we performed reactions with resveratrol (0.12 m M ) and tyrosinase (50 U mL −1 ) in the presence of cast chitosan fi lms. At specifi c times, the fi lms were removed from the reaction solution, rinsed and then the fi lms' UV-vis spectra were measured.…”

Section: Optical Information Stored In the Filmsmentioning

confidence: 99%

Enzymatic Writing to Soft Films: Potential to Filter, Store, and Analyze Biologically Relevant Chemical Information

Liu

Kim

Lee

et al. 2013

Adv Funct Materials

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Sensor‐based chemical analyses commonly enlist either the molecular recognition capabilities of biology (e.g., enzyme biosensors) or advanced information processing algorithms (e.g., the electronic nose). Here, a hybrid approach is proposed in which an enzyme is used to “filter” chemical information and write this information to a film which then serves as a permanent storage medium that can be ‘read’ repeatedly, interactively, and by multiple sensor modalities. This approach is demonstrated by analyzing common dietary phenols that are reported to offer health benefits. Specifically, the enzyme tyrosinase is used to convert these phenols into reactive quinones that graft (i.e., write) to a chitosan film. Grafting can be detected by optical, mechanical, and electrochemical sensors. Importantly, grafting confers redox activity to the films and this redox activity can be probed interactively by advanced electrochemical methods that allow the intrinsic redox reactivities to be compared, redox interactions to be identified, and biologically relevant redox activities to be examined. The transfer of chemical and biological information to a film is envisioned to provide broader access to the extensive capabilities offered by sensor technologies and signal processing methodologies.

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Resveratrol as a kcat type inhibitor for tyrosinase: Potentiated melanogenesis inhibitor

Cited by 62 publications

References 40 publications

Inhibition of melanogenesis by 2-[4-(5-chlorobenzo[d]thiazol-2-yl)phenoxy]-2-methylpropanoic acid (MHY908)

Inhibition of melanogenesis by 2-[4-(5-chlorobenzo[d]thiazol-2-yl)phenoxy]-2-methylpropanoic acid (MHY908)

Inhibitory Effects of Resveratrol Analogs on Mushroom Tyrosinase Activity

Enzymatic Writing to Soft Films: Potential to Filter, Store, and Analyze Biologically Relevant Chemical Information

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