Glycine hydroxamate inhibits tyrosinase activity and melanin contents through downregulating cAMP/PKA signaling pathways

Lin, Yin Shiou; Wu, Wen Chung; Lin, Shyr Yi; Hou, Wen Chi

doi:10.1007/s00726-014-1895-8

Cited by 14 publications

(13 citation statements)

References 29 publications

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“…Melanin is generated through a process, called as melanogenesis within the intracellular melanosomes of melanocytes, and the production and distribution of melanin determines the skin, eyes and hair color. In addition, melanin plays a vital role in protecting skin from various molecules and stimuli such as ultraviolet (UV) radiation, reactive oxygen species (ROS), α-melanocyte-stimulating hormone (α-MSH) and cyclic adenosine monophosphate (cAMP) elevating agents including forskolin and IBMX [1]. In particular, UV radiation directly and indirectly damages skin cells via ROS generation such as hydroxyl radicals, superoxide anions, and hydrogen peroxide [2].…”

Section: Introductionmentioning

confidence: 99%

Anti-Melanogenic Effect of Ethanolic Extract of Sorghum bicolor on IBMX–Induced Melanogenesis in B16/F10 Melanoma Cells

et al. 2020

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To evaluate possibility as a skin whitening agent of Sorghum bicolor (S. bicolor), its antioxidant activity and anti-melanogenic effect on 3-isobutyl-1-methylxanthine (IBMX)-induced melanogenesis in B16/F10 melanoma cells were investigated. The result of total phenolic contents (TPC) indicated that 60% ethanol extract of S. bicolor (ESB) has the highest contents than other ethanol extracts. Antioxidant activity was evaluated using the 2,2’-azino-bis-(3-ethylbenzothiazolin-6-sulfonic acid) diammonium salt (ABTS)/1,1-diphenyl-2-picryl-hydrazyl (DPPH) radical scavenging activities and malondialdehyde (MDA) inhibitory effect. These results showed ESB has significant antioxidant activities. Inhibitory effect against tyrosinase was also assessed using L-tyrosine (IC50 value = 89.25 μg/mL) and 3,4-dihydroxy-L-phenylalanine (L-DOPA) as substrates. In addition, ESB treatment effectively inhibited melanin production in IBMX-induced B16/F10 melanoma cells. To confirm the mechanism on anti-melanogenic effect of ESB, we examined melanogenesis-related proteins. ESB downregulated melanogenesis by decreasing expression of microphthalmia-associated transcription factor (MITF), tyrosinase and tyrosinase-related protein (TRP)-1. Finally, 9-hydroxyoctadecadienoic acid (9-HODE), 1,3-O-dicaffeoylglycerol and tricin as the main compounds of ESB were analyzed using the ultra-performance liquid chromatography-ion mobility separation-quadrupole time of flight/tandem mass spectrometry (UPLC-IMS-QTOF/MS2). These findings suggest that ESB may have physiological potential to be used skin whitening material.

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Section: Introductionmentioning

confidence: 99%

Anti-Melanogenic Effect of Ethanolic Extract of Sorghum bicolor on IBMX–Induced Melanogenesis in B16/F10 Melanoma Cells

et al. 2020

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“…Therefore, the phenolic moiety can act as an MBG to directly interact with tyrosinase. An extensive survey indicated three reports on tyrosinase inhibition by hydroxamate-containing molecules [ 37 , 38 , 39 ]. The compounds include glycine hydroxamate [ 37 ], HCA-Phe-NHOH and HCA-Pro-NHOH [ 38 ], and caffeoyl-amino acidyl-hydroxamic acid [ 39 ].…”

Section: Resultsmentioning

confidence: 99%

Hydroxamic Acid as a Potent Metal-Binding Group for Inhibiting Tyrosinase

et al. 2022

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Tyrosinase, a metalloenzyme containing a dicopper cofactor, plays a central role in synthesizing melanin from tyrosine. Many studies have aimed to identify small-molecule inhibitors of tyrosinase for pharmaceutical, cosmetic, and agricultural purposes. In this study, we report that hydroxamic acid is a potent metal-binding group for interacting with dicopper atoms, thereby inhibiting tyrosinase. Hydroxamate-containing molecules, including anticancer drugs targeting histone deacetylase, vorinostat and panobinostat, significantly inhibited mushroom tyrosinase, with inhibitory constants in the submicromolar range. Of the tested molecules, benzohydroxamic acid was the most potent. Its inhibitory constant of 7 nM indicates that benzohydroxamic acid is one of the most potent tyrosinase inhibitors. Results from differential scanning fluorimetry revealed that direct binding mediates inhibition. The enzyme kinetics were studied to assess the inhibitory mechanism of the hydroxamate-containing molecules. Experiments with B16F10 cell lysates confirmed that the new inhibitors are inhibitory against mammalian tyrosinase. Docking simulation data revealed intermolecular contacts between hydroxamate-containing molecules and tyrosinase.

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“…However, excessive melanin can cause skin aging [ 23 , 24 ]. Abundant production and excessive activation of TYR can cause excess formation of melanin [ 25 ]. The results presented here show that UV irradiation could significantly upregulate TYR activity and melanin content in the skin.…”

Section: Discussionmentioning

confidence: 99%

Therapeutic Effect of Seawater Pearl Powder on UV-Induced Photoaging in Mouse Skin

Han

Huang

Lan

et al. 2021

Evidence-Based Complementary and Alternative Medicine

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The objective of this study was to investigate the therapeutic effect of seawater pearl powder (SPP) on ultraviolet (UV) irradiation-induced photoaging in mouse skin. The protein and trace elements in SPP were detected by liquid chromatography-mass spectrometry, atomic fluorescence spectrometry, and inductively coupled plasma-atomic emission spectrometry. The effect of SPP on treating skin damage resulting from UV-induced photoaging was observed by gross physical appearance and histopathological analysis. Oxidative stress and melanin synthesis were analyzed using biochemical method. Western blotting was applied to analyze the phosphorylation and expression levels of matrix metalloproteinase-1 (MMP-1), collagen I, and proteins involved in the mitogen-activated protein kinase (MAPK) signaling pathways (p38, ERK, and JNK). The results show that SPP has a significant therapeutic effect on UV-induced photoaging of skin and improves and restores appearance and tissue structure of mouse skin. The major mechanism may be related to reduction of expression level of MMP-1 and enhancement of collagen I production via inhibition of MAPK signaling pathway after scavenging of excess reactive oxygen species (ROS) in the UV-induced photoaged skin of mice. Meanwhile, it may also be involved in reducing melanin content by inhibiting tyrosinase activity after scavenging excess ROS in the UV-induced photoaged skin of mice. Therefore, SPP could be a good substance to treat photoaging skin. Taking cost-effectiveness and efficacy into consideration, the optimal concentration of SPP for treating photoaging skin could be 100 mg/g.

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Glycine hydroxamate inhibits tyrosinase activity and melanin contents through downregulating cAMP/PKA signaling pathways

Cited by 14 publications

References 29 publications

Anti-Melanogenic Effect of Ethanolic Extract of Sorghum bicolor on IBMX–Induced Melanogenesis in B16/F10 Melanoma Cells

Anti-Melanogenic Effect of Ethanolic Extract of Sorghum bicolor on IBMX–Induced Melanogenesis in B16/F10 Melanoma Cells

Hydroxamic Acid as a Potent Metal-Binding Group for Inhibiting Tyrosinase

Therapeutic Effect of Seawater Pearl Powder on UV-Induced Photoaging in Mouse Skin

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