Tyrosinase-catalyzed metabolism of rhododendrol (RD) in B16 melanoma cells: production of RD-pheomelanin and covalent binding with thiol proteins.

Abstract:

:RS-4-(4-Hydroxyphenyl)-2-butanol (rhododendrol, RD) was reported to induce leukoderma of the skin. To explore the mechanism underlying that effect, we previously showed that oxidation of RD with mushroom tyrosinase produces RD-quinone, which is converted to secondary quinone products, and we suggested that those quinones are cytotoxic because they bind to cellular proteins and produce reactive oxygen species. We then confirmed that human tyrosinase can oxidize both enantiomers of RD. In this study, we examined the metabolism of RD in B16F1 melanoma cells in vitro. Using 4-amino-3-hydroxy-n-butylbenzene as a specific indicator, we detected moderate levels of RD-pheomelanin in B16F1 cells exposed to 0.3 to 0.5 mM RD for 72 h. We also confirmed the covalent binding of RD-quinone to non-protein thiols and proteins through cysteinyl residues. The covalent binding of RD-quinone to proteins was 20- to 30-fold greater than dopaquinone. These results suggest that the tyrosinase-induced metabolism of RD causes melanocyte toxicity.

authors

Ito S,Okura M,Nakanishi Y,Ojika M,Wakamatsu K,Yamashita T

doi

10.1111/pcmr.12363

subject

Has Abstract

pub_date

2015-05-01 00:00:00

pages

295-306

issue

3

eissn

1755-1471

issn

1755-148X

journal_volume

28

pub_type

杂志文章
  • The 308-nm excimer laser treatment does not increase the risk of skin cancer in patients with vitiligo: A population-based retrospective cohort study.

    abstract::A 308-nm excimer laser (EL) has been widely used to treat patients with localized vitiligo. However, data are rare on the influence of EL treatment on the risks of skin cancer. To evaluate the skin cancer risks after long-term EL treatment, we performed a nationwide population-based retrospective cohort study using th...

    journal_title:Pigment cell & melanoma research

    pub_type: 杂志文章

    doi:10.1111/pcmr.12781

    authors: Bae JM,Eun SH,Oh SH,Shin JH,Kang HY,Kim KH,Lee SC,Choi CW

    更新日期:2019-09-01 00:00:00

  • Distinct microRNA expression signatures are associated with melanoma subtypes and are regulated by HIF1A.

    abstract::The complex genetic changes underlying metastatic melanoma need to be deciphered to develop new and effective therapeutics. Previously, genome-wide microarray analyses of human melanoma identified two reciprocal gene expression programs, including transcripts regulated by either transforming growth factor, beta 1 (TGF...

    journal_title:Pigment cell & melanoma research

    pub_type: 杂志文章

    doi:10.1111/pcmr.12255

    authors: Hwang HW,Baxter LL,Loftus SK,Cronin JC,Trivedi NS,Borate B,Pavan WJ

    更新日期:2014-09-01 00:00:00

  • Bimodal effect of retinoic acid on melanocyte differentiation identified by time-dependent analysis.

    abstract::Retinoic acid (RA) is considered to control melanocytes; however, its precise mechanism remains unclear because of a bimodal effect, which promotes or inhibits melanin synthesis depending on the cell type, culture condition of melanocytes and skin conditions. In this study, we examined the effects of RA throughout eac...

    journal_title:Pigment cell & melanoma research

    pub_type: 杂志文章

    doi:10.1111/j.1755-148X.2012.00988.x

    authors: Inoue Y,Hasegawa S,Yamada T,Date Y,Mizutani H,Nakata S,Matsunaga K,Akamatsu H

    更新日期:2012-05-01 00:00:00

  • ABCB5 is activated by MITF and β-catenin and is associated with melanoma differentiation.

    abstract::Defining markers of different phenotypic states in melanoma is important for understanding disease progression, determining the response to therapy, and defining the molecular mechanisms underpinning phenotype-switching driven by the changing intratumor microenvironment. The ABCB5 transporter is implicated in drug-res...

    journal_title:Pigment cell & melanoma research

    pub_type: 杂志文章

    doi:10.1111/pcmr.12830

    authors: Louphrasitthiphol P,Chauhan J,Goding CR

    更新日期:2020-01-01 00:00:00

  • The interaction between vitamin D receptor polymorphisms and sun exposure around time of diagnosis influences melanoma survival.

    abstract::Evidence on the relationship between the vitamin D pathway and outcomes in melanoma is growing, although it is not always clear. We investigated the impact of measured levels of sun exposure at diagnosis on associations of vitamin D receptor gene (VDR) polymorphisms and melanoma death in 3336 incident primary melanoma...

    journal_title:Pigment cell & melanoma research

    pub_type: 杂志文章

    doi:10.1111/pcmr.12653

    authors: Orlow I,Shi Y,Kanetsky PA,Thomas NE,Luo L,Corrales-Guerrero S,Cust AE,Sacchetto L,Zanetti R,Rosso S,Armstrong BK,Dwyer T,Venn A,Gallagher RP,Gruber SB,Marrett LD,Anton-Culver H,Busam K,Begg CB,Berwick M,GEM Study

    更新日期:2018-03-01 00:00:00

  • PMEL: a pigment cell-specific model for functional amyloid formation.

    abstract::PMEL is a pigment cell-specific protein responsible for the formation of fibrillar sheets within the pigment organelle, the melanosome. The fibrillar sheets serve as a template upon which melanins polymerize as they are synthesized. The PMEL fibrils are required for optimal pigment cell function, as animals that eithe...

    journal_title:Pigment cell & melanoma research

    pub_type: 杂志文章,评审

    doi:10.1111/pcmr.12067

    authors: Watt B,van Niel G,Raposo G,Marks MS

    更新日期:2013-05-01 00:00:00

  • Raman spectroscopy as a non-invasive technique for the quantification of melanins in feathers and hairs.

    abstract::The quantification of melanins is a complex task due to the chemical heterogeneity of the pigments and the difficulty of their isolation. The best accepted procedure currently consists in the chemical cleavage of melanins and the subsequent detection of degradation products by HPLC, which implies the destruction of sa...

    journal_title:Pigment cell & melanoma research

    pub_type: 杂志文章

    doi:10.1111/pcmr.12140

    authors: Galván I,Jorge A,Ito K,Tabuchi K,Solano F,Wakamatsu K

    更新日期:2013-11-01 00:00:00

  • Identification of PLX4032-resistance mechanisms and implications for novel RAF inhibitors.

    abstract::BRAF inhibitors improve melanoma patient survival, but resistance invariably develops. Here we report the discovery of a novel BRAF mutation that confers resistance to PLX4032 employing whole-exome sequencing of drug-resistant BRAF(V600K) melanoma cells. We further describe a new screening approach, a genome-wide pigg...

    journal_title:Pigment cell & melanoma research

    pub_type: 杂志文章

    doi:10.1111/pcmr.12197

    authors: Choi J,Landrette SF,Wang T,Evans P,Bacchiocchi A,Bjornson R,Cheng E,Stiegler AL,Gathiaka S,Acevedo O,Boggon TJ,Krauthammer M,Halaban R,Xu T

    更新日期:2014-03-01 00:00:00

  • Induced pluripotent stem cell-derived melanocyte precursor cells undergoing differentiation into melanocytes.

    abstract::Induced pluripotent stem cell (iPSC) technology offers a novel approach for conversion of human primary fibroblasts into melanocytes. During attempts to explore various protocols for differentiation of iPSCs into melanocytes, we found a distinct and self-renewing cell lineage that could differentiate into melanocytes,...

    journal_title:Pigment cell & melanoma research

    pub_type: 杂志文章

    doi:10.1111/pcmr.12779

    authors: Hosaka C,Kunisada M,Koyanagi-Aoi M,Masaki T,Takemori C,Taniguchi-Ikeda M,Aoi T,Nishigori C

    更新日期:2019-09-01 00:00:00

  • Advances in melanoma senescence and potential clinical application.

    abstract::Normal cells possess a limited proliferative life span, after which they enter a state of irreversible growth arrest, called replicative senescence, which acts as a potent barrier against transformation. Transformed cells have escaped the process of replicative senescence and theoretically can not re-enter senescence....

    journal_title:Pigment cell & melanoma research

    pub_type: 杂志文章,评审

    doi:10.1111/j.1755-148X.2010.00820.x

    authors: Giuliano S,Ohanna M,Ballotti R,Bertolotto C

    更新日期:2011-04-01 00:00:00

  • High frequency of PTEN mutations in nevi and melanomas from xeroderma pigmentosum patients.

    abstract::We examined nevi and melanomas in 10 xeroderma pigmentosum (XP) patients with defective DNA repair. The lesions had a lentiginous appearance with markedly increased numbers of melanocytes. Using laser capture microdissection, we performed DNA sequencing of 18 benign and atypical nevi and 75 melanomas (melanoma in situ...

    journal_title:Pigment cell & melanoma research

    pub_type: 杂志文章

    doi:10.1111/pcmr.12226

    authors: Masaki T,Wang Y,DiGiovanna JJ,Khan SG,Raffeld M,Beltaifa S,Hornyak TJ,Darling TN,Lee CC,Kraemer KH

    更新日期:2014-05-01 00:00:00

  • Current opportunities and challenges: genome-wide association studies on pigmentation and skin cancer.

    abstract::Genome-wide association studies (GWAS) have become a widely used approach for genetic association studies of various human traits. A few GWAS have been conducted with the goal of identifying novel loci for pigmentation traits, melanoma, and non-melanoma skin cancer. Nevertheless, the phenotype variation explained by t...

    journal_title:Pigment cell & melanoma research

    pub_type: 杂志文章,评审

    doi:10.1111/j.1755-148X.2012.01023.x

    authors: Meng S,Zhang M,Liang L,Han J

    更新日期:2012-09-01 00:00:00

  • Melanocortin-1 receptor-mediated signalling pathways activated by NDP-MSH and HBD3 ligands.

    abstract::Binding of melanocortin peptide agonists to the melanocortin-1 receptor of melanocytes results in eumelanin production, whereas binding of the agouti signalling protein inverse agonist results in pheomelanin synthesis. Recently, a novel melanocortin-1 receptor ligand was reported. A β-defensin gene mutation was found ...

    journal_title:Pigment cell & melanoma research

    pub_type: 杂志文章

    doi:10.1111/j.1755-148X.2012.00990.x

    authors: Beaumont KA,Smit DJ,Liu YY,Chai E,Patel MP,Millhauser GL,Smith JJ,Alewood PF,Sturm RA

    更新日期:2012-05-01 00:00:00

  • NF1 loss induces senescence during human melanocyte differentiation in an iPSC-based model.

    abstract::Neurofibromatosis type 1 (NF1) is a frequent genetic disease leading to the development of Schwann cell-derived neurofibromas or melanocytic lesions called café-au-lait macules (CALMs). The molecular mechanisms involved in CALMs formation remain largely unknown. In this report, we show for the first time pathophysiolo...

    journal_title:Pigment cell & melanoma research

    pub_type: 杂志文章

    doi:10.1111/pcmr.12369

    authors: Larribere L,Wu H,Novak D,Galach M,Bernhardt M,Orouji E,Weina K,Knappe N,Sachpekidis C,Umansky L,Beckhove P,Umansky V,De Schepper S,Kaufmann D,Ballotti R,Bertolotto C,Utikal J

    更新日期:2015-07-01 00:00:00

  • Vitiligo as an inflammatory skin disorder: a therapeutic perspective.

    abstract::From a therapeutic standpoint, vitiligo is still regarded by many physicians as a simple problem of regenerative medicine, with the main aim to repopulate the depigmented skin with functional melanocytes from the margins of the lesions or from intact progenitors in hair follicles. However, recent research in vitiligo ...

    journal_title:Pigment cell & melanoma research

    pub_type: 杂志文章,评审

    doi:10.1111/j.1755-148X.2011.00939.x

    authors: Taïeb A

    更新日期:2012-01-01 00:00:00

  • Loss of Klotho during melanoma progression leads to increased filamin cleavage, increased Wnt5A expression, and enhanced melanoma cell motility.

    abstract::We have previously shown that Wnt5A-mediated signaling can promote melanoma metastasis. It has been shown that Wnt signaling is antagonized by the protein Klotho, which has been implicated in aging. We show here that in melanoma cells, expressions of Wnt5A and Klotho are inversely correlated. In the presence of recomb...

    journal_title:Pigment cell & melanoma research

    pub_type: 杂志文章

    doi:10.1111/j.1755-148X.2010.00792.x

    authors: Camilli TC,Xu M,O'Connell MP,Chien B,Frank BP,Subaran S,Indig FE,Morin PJ,Hewitt SM,Weeraratna AT

    更新日期:2011-02-01 00:00:00

  • Novel regulation of melanogenesis by adiponectin via the AMPK/CRTC pathway.

    abstract::Several studies observed that adiponectin, an important adipokine that improves glucose metabolism by regulating AMP-activated protein kinase (AMPK) signaling, is dermatologically beneficial. In our recent microarray data, we found that adiponectin expression was lower in lesional skin than in non-lesional skin of mel...

    journal_title:Pigment cell & melanoma research

    pub_type: 杂志文章

    doi:10.1111/pcmr.12596

    authors: Bang S,Won KH,Moon HR,Yoo H,Hong A,Song Y,Chang SE

    更新日期:2017-01-01 00:00:00

  • Re-evaluation of insect melanogenesis research: Views from the dark side.

    abstract::Melanins (eumelanin and pheomelanin) are synthesized in insects for several purposes including cuticle sclerotization and color patterning, clot formation, organogenesis, and innate immunity. Traditional views of insect immunity detail the storage of pro-phenoloxidases inside specialized blood cells (hemocytes) and th...

    journal_title:Pigment cell & melanoma research

    pub_type: 杂志文章,评审

    doi:10.1111/pcmr.12590

    authors: Whitten MMA,Coates CJ

    更新日期:2017-07-01 00:00:00

  • The melanomas: a synthesis of epidemiological, clinical, histopathological, genetic, and biological aspects, supporting distinct subtypes, causal pathways, and cells of origin.

    abstract::Converging lines of evidence from varied scientific disciplines suggest that cutaneous melanomas comprise biologically distinct subtypes that arise through multiple causal pathways. Understanding the respective relationships of each subtype with etiologic factors such as UV radiation and constitutional factors is the ...

    journal_title:Pigment cell & melanoma research

    pub_type: 杂志文章,评审

    doi:10.1111/j.1755-148X.2011.00880.x

    authors: Whiteman DC,Pavan WJ,Bastian BC

    更新日期:2011-10-01 00:00:00

  • Decreased regulatory T-cells and CD4(+) /CD8(+) ratio correlate with disease onset and progression in patients with generalized vitiligo.

    abstract::The aim of present study was to evaluate CD4(+) /CD8(+) ratio and CD4(+) CD25(hi) FoxP3(+) Tregs in GV patients with reference to their effect on disease onset and progression. Flow cytometry was used for determination of CD4(+) /CD8(+) ratio and Tregs in 82 patients and 50 controls. CD8(+) T-cell counts were signific...

    journal_title:Pigment cell & melanoma research

    pub_type: 杂志文章

    doi:10.1111/pcmr.12105

    authors: Dwivedi M,Laddha NC,Arora P,Marfatia YS,Begum R

    更新日期:2013-07-01 00:00:00

  • Keratinocytes in culture accumulate phagocytosed melanosomes in the perinuclear area.

    abstract::There are many techniques for evaluating melanosome transfer to keratinocytes but the spectrophotometric quantification of melanosomes incorporated by keratinocyte phagocytosis has not been previously reported. Here we describe a new method that allows the spectrophotometric visualization of melanosome uptake by norma...

    journal_title:Pigment cell & melanoma research

    pub_type: 杂志文章

    doi:10.1111/j.1755-148X.2009.00640.x

    authors: Ando H,Niki Y,Yoshida M,Ito M,Akiyama K,Kim JH,Yoon TJ,Lee JH,Matsui MS,Ichihashi M

    更新日期:2010-02-01 00:00:00

  • The mouse ruby-eye 2(d) (ru2(d) /Hps5(ru2-d) ) allele inhibits eumelanin but not pheomelanin synthesis.

    abstract::The novel mutation named ru2(d) /Hps5(ru2-d) , characterized by light-colored coats and ruby-eyes, prohibits differentiation of melanocytes by inhibiting tyrosinase (Tyr) activity, expression of Tyr, Tyr-related protein 1 (Tyrp1), Tyrp2, and Kit. However, it is not known whether the ru2(d) allele affects pheomelanin s...

    journal_title:Pigment cell & melanoma research

    pub_type: 杂志文章

    doi:10.1111/pcmr.12118

    authors: Hirobe T,Ito S,Wakamatsu K

    更新日期:2013-09-01 00:00:00

  • The state of melanoma: challenges and opportunities.

    abstract::The Melanoma Research Foundation (MRF) has charted a comprehensive assessment of the current state of melanoma research and care. Intensive discussions among members of the MRF Scientific Advisory Council and Breakthrough Consortium, a group that included clinicians and scientists, focused on four thematic areas - dia...

    journal_title:Pigment cell & melanoma research

    pub_type: 杂志文章

    doi:10.1111/pcmr.12475

    authors: Merlino G,Herlyn M,Fisher DE,Bastian BC,Flaherty KT,Davies MA,Wargo JA,Curiel-Lewandrowski C,Weber MJ,Leachman SA,Soengas MS,McMahon M,Harbour JW,Swetter SM,Aplin AE,Atkins MB,Bosenberg MW,Dummer R,Gershenwald JE,Ha

    更新日期:2016-07-01 00:00:00

  • Independent regulation of hair and skin color by two G protein-coupled pathways.

    abstract::Hair color and skin color are frequently coordinated in mammalian species. To explore this, we have studied mutations in two different G protein coupled pathways, each of which affects the darkness of both hair and skin color. In each mouse mutant (Gnaq(Dsk1), Gna11(Dsk7), and Mc1r(e)), we analyzed the melanocyte dens...

    journal_title:Pigment cell & melanoma research

    pub_type: 杂志文章

    doi:10.1111/j.1755-148X.2009.00609.x

    authors: Van Raamsdonk CD,Barsh GS,Wakamatsu K,Ito S

    更新日期:2009-12-01 00:00:00

  • Pigmentation PAX-ways: the role of Pax3 in melanogenesis, melanocyte stem cell maintenance, and disease.

    abstract::Transcription factors initiate programs of gene expression and are catalysts in downstream molecular cascades that modulate a variety of cellular processes. Pax3 is a transcription factor that is important in the melanocyte and influences melanocytic proliferation, resistance to apoptosis, migration, lineage specifici...

    journal_title:Pigment cell & melanoma research

    pub_type: 杂志文章,评审

    doi:10.1111/j.1755-148X.2008.00514.x

    authors: Kubic JD,Young KP,Plummer RS,Ludvik AE,Lang D

    更新日期:2008-12-01 00:00:00

  • Pharmacologic suppression of MITF expression via HDAC inhibitors in the melanocyte lineage.

    abstract::Melanoma incidence continues to rise at an alarming rate while effective systemic therapies remain very limited. Microphthalmia-associated transcription factor (MITF) is required for development of melanocytes and is an amplified oncogene in a fraction of human melanomas. Microphthalmia-associated transcription factor...

    journal_title:Pigment cell & melanoma research

    pub_type: 杂志文章

    doi:10.1111/j.1755-148X.2008.00480.x

    authors: Yokoyama S,Feige E,Poling LL,Levy C,Widlund HR,Khaled M,Kung AL,Fisher DE

    更新日期:2008-08-01 00:00:00

  • BRG1 promotes survival of UV-irradiated melanoma cells by cooperating with MITF to activate the melanoma inhibitor of apoptosis gene.

    abstract::Microphthalmia-associated transcription factor (MITF) is a survival factor in melanocytes and melanoma cells. MITF regulates expression of antiapoptotic genes and promotes lineage-specific survival in response to ultraviolet (UV) radiation and to chemotherapeutics. SWI/SNF chromatin-remodeling enzymes interact with MI...

    journal_title:Pigment cell & melanoma research

    pub_type: 杂志文章

    doi:10.1111/pcmr.12088

    authors: Saladi SV,Wong PG,Trivedi AR,Marathe HG,Keenen B,Aras S,Liew ZQ,Setaluri V,de la Serna IL

    更新日期:2013-05-01 00:00:00

  • NLRP1, a regulator of innate immunity associated with vitiligo.

    abstract::Some familial forms of the dermatological condition vitiligo have recently been linked to polymorphisms in the innate immunity gene, NLRP1. Here, we review what is currently known about the mechanisms that regulate activation of the NLRP1 protein and the downstream effects of NLRP1 on pathways impacting inflammation a...

    journal_title:Pigment cell & melanoma research

    pub_type: 杂志文章,评审

    doi:10.1111/j.1755-148X.2011.00942.x

    authors: D'Osualdo A,Reed JC

    更新日期:2012-01-01 00:00:00

  • Reverse TCA cycle flux through isocitrate dehydrogenases 1 and 2 is required for lipogenesis in hypoxic melanoma cells.

    abstract::The tricarboxylic acid (TCA) cycle is the central hub of oxidative metabolism, running in the classic forward direction to provide carbon for biosynthesis and reducing agents for generation of ATP. Our metabolic tracer studies in melanoma cells showed that in hypoxic conditions the TCA cycle is largely disconnected fr...

    journal_title:Pigment cell & melanoma research

    pub_type: 杂志文章

    doi:10.1111/j.1755-148X.2012.00989.x

    authors: Filipp FV,Scott DA,Ronai ZA,Osterman AL,Smith JW

    更新日期:2012-05-01 00:00:00

  • D-tyrosine negatively regulates melanin synthesis by competitively inhibiting tyrosinase activity.

    abstract::Although L-tyrosine is well known for its melanogenic effect, the contribution of D-tyrosine to melanin synthesis was previously unexplored. Here, we reveal that, unlike L-tyrosine, D-tyrosine dose-dependently reduced the melanin contents of human MNT-1 melanoma cells and primary human melanocytes. In addition, 500 μM...

    journal_title:Pigment cell & melanoma research

    pub_type: 杂志文章

    doi:10.1111/pcmr.12668

    authors: Park J,Jung H,Kim K,Lim KM,Kim JY,Jho EH,Oh ES

    更新日期:2018-05-01 00:00:00