A Novel Synthesized Tyrosinase Inhibitor: (<i>E</i>)-2-((2,4-Dihydroxyphenyl)diazenyl)phenyl 4-Methylbenzenesulfonate as an Azo-Resveratrol Analog

Bae, Sung Jin; Ha, Young Mi; Kim, Jinah; Park, Ji Young; Ha, Tae Kwon; Park, Daeui; Chun, Pusoon; Park, Nam Hee; Moon, Hyung Ryong; Chung, Hae Young

doi:10.1271/bbb.120547

Cited by 34 publications

(31 citation statements)

References 44 publications

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“…Recent reports have shown that resveratrol produced therapeutic effects against hyperplastic skin disorders by inhibiting keratinocyte proliferation , inhibited skin photoaging by acting as a Sirt-1 agonist (Lee et al, 2010), and showed anti-cancer effects in human melanoma cell lines (Niles et al, 2003). The anti-melanogenic effects of resveratrol and resveratrol analogs have already been reported by many other groups (Ohguchi et al, 2003;Song et al, 2012;Bae et al, 2013;Park and Boo, 2013;Park et al, 2014). We previously demonstrated the depigmentation effects of resveratrol in UVB-treated guinea pigs , too.…”

Section: Introductionsupporting

confidence: 55%

“…Interestingly, RR shows synergistic effects in comparison that of each resveratrol or rice alone (Baek et al, 2013;Baek et al, 2014). Several reports show that resveratrol decreases the expression of tyrosinase (Franco et al, 2012;Zheng et al, 2012;Bae et al, 2013;Park and Boo, 2013;Park et al, 2014), and Jun et al reported that gamma-oryzanol from rice extract dually inhibited cellular melanogenesis, too (Jun et al, 2012). Because each of resveratrol and rice had anti-melanogenic effects, we expected that RR would produce synergistic antimelanogenic effects and thus have some advantages over treatment with rice or resveratrol alone.…”

Section: Discussionmentioning

confidence: 95%

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Resveratrol-Enriched Rice Down-Regulates Melanin Synthesis in UVB-Induced Guinea Pigs Epidermal Skin Tissue

Lee¹,

Seo²,

Ho³

et al. 2014

Biomol Ther

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This is an Open Access article distributed under the terms of the Creative Commons Attribution Non-Commercial License (http://creativecommons.org/licenses/by-nc/3.0/) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited. www.biomolther.orgSynthetic compounds that are used in the clinic to regulate skin hyperpigmentation, such as arbutin, hydroquinone, and kojic acid, are only moderately effective. But, their use is limited by side effects. As part of an effort to overcome the limitations, we developed resveratrol-enriched rice (RR) using genetic engineering technique. Each of resveratrol and rice has been reported to produce anti-melanogenic effects. Therefore, we hypothesized that RR would show more anti-melanogenic effects than those of resveratrol or rice alone. Anti-melanogenic effect of RR was done by using melan-a mouse melanocytes. The depigmenting efficacy was then observed following topical application of the RR to UVB-stimulated hyperpigmented dorsal skin of guinea pigs. Treatment with RR extract resulted a 21.4 ± 0.7% decrease in tyrosinase expression at melan-a cells. Colorimetric analysis showed a significantly lower depigmenting value by day 9 following treatment with RR in UVB-irradiated guinea pigs the dorsal skin (p<0.01), indicating that RR produced a depigmentation effect. By staining with Fontana-Masson stain, we found that the RR-treated group had more effect histopathologically in epidermal melanin production than resveratrol or rice alone-treated group. RR was associated with reduction in the levels of microphthalmia-associated transcription factor (MITF), and downregulation of tyrosinase and tyrosinaserelated protein (TRP-2) expression, leading to inhibit epidermal melanin production by western blot analysis. This study suggests that the resveratrol-enriched rice may be a promising candidate in regulating skin pigmentation with UVB exposure.

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Section: Introductionsupporting

confidence: 55%

Section: Discussionmentioning

confidence: 95%

Resveratrol-Enriched Rice Down-Regulates Melanin Synthesis in UVB-Induced Guinea Pigs Epidermal Skin Tissue

Lee¹,

Seo²,

Ho³

et al. 2014

Biomol Ther

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“…By estimating the oxidation rate of l -dopa, tyrosinase activities were evaluated with minor modifications, as described in previous work 20. Cells seeded at a density of 5×10 4 cell/well in a 24-well plate were allowed to adhere at 37°C in a humidified atmosphere containing 5% CO 2 for 24 hours.…”

Section: Methodsmentioning

confidence: 99%

Design, synthesis, and antimelanogenic effects of (2-substituted phenyl-1,3-dithiolan-4-yl)methanol derivatives

Kim

Ullah

et al. 2017

DDDT

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The authors designed and synthesized 17 (2-substituted phenyl-1,3-dithiolan-4-yl) methanol (PDTM) derivatives to find a new chemical scaffold, showing excellent tyrosinase-inhibitory activity. Their tyrosinase-inhibitory activities were evaluated against mushroom tyrosinase at 50 μM, and five of the PDTM derivatives (PDTM3, PDTM7–PDTM9, and PDTM13) were found to inhibit mushroom tyrosinase more than kojic acid or arbutin, the positive controls. Of seventeen PDTMs, PDTM3 (half-maximal inhibitory concentration 13.94±1.76 μM), with a 2,4-dihydroxyphenyl moiety, exhibited greatest inhibitory effects (kojic acid half-maximal inhibitory concentration 18.86±2.14 μM). Interestingly, PDTM compounds with no hydroxyl group, PDTM7–PDTM9, also had stronger inhibitory activities than kojic acid. In silico studies of interactions between tyrosinase and the five PDTMs suggested their binding affinities were closely related to their tyrosinase-inhibitory activities. Cell-based experiments performed using B16F10 mouse-skin melanoma cells showed that PDTM3 effectively inhibited melanogenesis and cellular tyrosinase activity. A cell-viability study conducted using B16F10 cells indicated that the antimelanogenic effect of PDTM3 was not attributable to its cytotoxicity. Kinetic studies showed PDTM3 competitively inhibited tyrosinase, indicating binding to the tyrosinase-active site. We found that PDTM3 with a new chemical scaffold could be a promising candidate for skin-whitening agents, and that the 1,3-dithiolane ring could be used as a chemical scaffold for potent tyrosinase inhibition.

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“…Resveratrol is a polyphenolic compound found in grapes, nuts, and berries [162] that increases mitochondrial biogenesis, acting as an anti-inflammatory, anti-diabetic, and anti-cancer compound [163], skin-depigmenting agent [162, 164, 165], anti-psoriatic [166], and wound-healing agent [167], among other properties.…”

Section: Resveratrolmentioning

confidence: 99%

“…Moreover, it has anti-inflammatory effects on macrophage, adipocyte, cultured adipocytes, and adipose tissue [162], as well as down-regulating tyrosinase [168] on melanocytes [166–171]. …”

Section: Resveratrolmentioning

confidence: 99%

Use of Polyphenolic Compounds in Dermatologic Oncology

2016

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Polyphenols are a widely used class of compounds in dermatology. While phenol itself, the most basic member of the phenol family, is chemically synthesized, most polyphenolic compounds are found in plants and form part of their defense mechanism against decomposition. Polyphenolic compounds, which include phenolic acids, flavonoids, stilbenes, and lignans, play an integral role in preventing the attack on plants by bacteria and fungi, as well as serving as cross-links in plant polymers. There is also mounting evidence that polyphenolic compounds play an important role in human health as well. One of the most important benefits, which puts them in the spotlight of current studies, is their antitumor profile. Some of these polyphenolic compounds have already presented promising results in either in vitro or in vivo studies for non-melanoma skin cancer and melanoma. These compounds act on several biomolecular pathways including cell division cycle arrest, autophagy, and apoptosis. Indeed, such natural compounds may be of potential for both preventive and therapeutic fields of cancer. This review evaluates the existing scientific literature in order to provide support for new research opportunities using polyphenolic compounds in oncodermatology.

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A Novel Synthesized Tyrosinase Inhibitor: (E)-2-((2,4-Dihydroxyphenyl)diazenyl)phenyl 4-Methylbenzenesulfonate as an Azo-Resveratrol Analog

Cited by 34 publications

References 44 publications

Resveratrol-Enriched Rice Down-Regulates Melanin Synthesis in UVB-Induced Guinea Pigs Epidermal Skin Tissue

Resveratrol-Enriched Rice Down-Regulates Melanin Synthesis in UVB-Induced Guinea Pigs Epidermal Skin Tissue

Design, synthesis, and antimelanogenic effects of (2-substituted phenyl-1,3-dithiolan-4-yl)methanol derivatives

Use of Polyphenolic Compounds in Dermatologic Oncology

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