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Volumn 80, Issue 1, 2015, Pages 18-24

A convenient screening method to differentiate phenolic skin whitening tyrosinase inhibitors from leukoderma-inducing phenols

Author keywords

Melanocyte toxicity; Rhododendrol; Tyrosinase; Tyrosinase inhibitor; Whitening agent

Indexed keywords

2,2' DIHYDROXY 5,50 DI N PROPYLBIPHENYL; 4 N BUTYLRESORCINOL; 4 TERT BUTYLCATECHOL; 4 TERT BUTYLPHENOL; ARBUTIN; DEPIGMENTING AGENT; ELLAGIC ACID; MEQUINOL; MONOBENZONE; MONOPHENOL MONOOXYGENASE; PHENOL; POTASSIUM 4 METHOXYSALICYLATE; RASPBERRY KETONE; RHODODENDROL; UNCLASSIFIED DRUG; ENZYME INHIBITOR; PHENOL DERIVATIVE; QUINONE DERIVATIVE;

EID: 84937859832     PISSN: 09231811     EISSN: 1873569X     Source Type: Journal    
DOI: 10.1016/j.jdermsci.2015.07.007     Document Type: Article
Times cited : (37)

References (43)
  • 1
    • 42549092546 scopus 로고    scopus 로고
    • Chemistry of mixed melanogenesis-pivotal roles of dopaquinone
    • Ito S., Wakamatsu K. Chemistry of mixed melanogenesis-pivotal roles of dopaquinone. Photochem. Photobiol. 2008, 84:582-592.
    • (2008) Photochem. Photobiol. , vol.84 , pp. 582-592
    • Ito, S.1    Wakamatsu, K.2
  • 2
    • 84897972480 scopus 로고    scopus 로고
    • Tyrosinase the four oxidation states of the active site and their relevance to enzymatic activation, oxidation and inactivation
    • Ramsden C.A., Riley P.A. Tyrosinase the four oxidation states of the active site and their relevance to enzymatic activation, oxidation and inactivation. Bioorg. Med. Chem. 2014, 22:2388-2395.
    • (2014) Bioorg. Med. Chem. , vol.22 , pp. 2388-2395
    • Ramsden, C.A.1    Riley, P.A.2
  • 4
    • 0018148688 scopus 로고
    • Autoxidation versus covalent binding of quinones as the mechanism of toxicity of dopamine, 6-hydroxydopamine, and related compounds toward C1300 neuroblastoma cells in vitro
    • Graham D.G., Tiffany S.M., Bell W.R., Gutknecht W.F. Autoxidation versus covalent binding of quinones as the mechanism of toxicity of dopamine, 6-hydroxydopamine, and related compounds toward C1300 neuroblastoma cells in vitro. Mol. Pharmacol. 1978, 14:644-653.
    • (1978) Mol. Pharmacol. , vol.14 , pp. 644-653
    • Graham, D.G.1    Tiffany, S.M.2    Bell, W.R.3    Gutknecht, W.F.4
  • 5
    • 78751684758 scopus 로고    scopus 로고
    • The haptenation theory of vitiligo and melanoma rejection: a close-up
    • Westerhof W., Manini P., Napolitano A., d'Ischia M. The haptenation theory of vitiligo and melanoma rejection: a close-up. Exp. Dermatol. 2011, 20:92-96.
    • (2011) Exp. Dermatol. , vol.20 , pp. 92-96
    • Westerhof, W.1    Manini, P.2    Napolitano, A.3    d'Ischia, M.4
  • 6
    • 84922677651 scopus 로고    scopus 로고
    • Guide for medical professionals (i.e., dermatologists) for the management of Rhododenol-induced leukoderma
    • Nishigori C., Aoyama Y., Ito A., Suzuki K., Suzuki T., Tanemura A., et al. Guide for medical professionals (i.e., dermatologists) for the management of Rhododenol-induced leukoderma. J. Dermatol. 2015, 42:113-128.
    • (2015) J. Dermatol. , vol.42 , pp. 113-128
    • Nishigori, C.1    Aoyama, Y.2    Ito, A.3    Suzuki, K.4    Suzuki, T.5    Tanemura, A.6
  • 7
    • 84922397128 scopus 로고    scopus 로고
    • Depigmentation caused by application of the active brightening material, rhododendrol, is related to tyrosinase activity at a certain threshold
    • Kasamatsu S., Hachiya A., Nakamura S., Yasuda Y., Fujimori T., et al. Depigmentation caused by application of the active brightening material, rhododendrol, is related to tyrosinase activity at a certain threshold. J. Dermatol. Sci. 2014, 76:16-24.
    • (2014) J. Dermatol. Sci. , vol.76 , pp. 16-24
    • Kasamatsu, S.1    Hachiya, A.2    Nakamura, S.3    Yasuda, Y.4    Fujimori, T.5
  • 8
    • 84907980722 scopus 로고    scopus 로고
    • Rhododendrol, a depigmentation-inducing phenolic compound, exerts melanocyte cytotoxicity via a tyrosinase-dependent mechanism
    • Sasaki M., Kondo M., Sato K., Umeda M., Kawabata K., Takahashi Y., et al. Rhododendrol, a depigmentation-inducing phenolic compound, exerts melanocyte cytotoxicity via a tyrosinase-dependent mechanism. Pigm. Cell Melanoma Res. 2014, 27:754-763.
    • (2014) Pigm. Cell Melanoma Res. , vol.27 , pp. 754-763
    • Sasaki, M.1    Kondo, M.2    Sato, K.3    Umeda, M.4    Kawabata, K.5    Takahashi, Y.6
  • 9
    • 84908012884 scopus 로고    scopus 로고
    • Tyrosinase-catalyzed oxidation of rhododendrol produces 2-methylchromane-6,7-dione, the putative ultimate toxic metabolite: implications for melanocyte toxicity
    • Ito S., Yamashita T., Ojika M., Wakamatsu K. Tyrosinase-catalyzed oxidation of rhododendrol produces 2-methylchromane-6,7-dione, the putative ultimate toxic metabolite: implications for melanocyte toxicity. Pigm. Cell Melanoma Res. 2014, 27:744-753.
    • (2014) Pigm. Cell Melanoma Res. , vol.27 , pp. 744-753
    • Ito, S.1    Yamashita, T.2    Ojika, M.3    Wakamatsu, K.4
  • 12
    • 84926628095 scopus 로고    scopus 로고
    • Tyrosinase-catalyzed metabolism of rhododendrol (RD) in B16 melanoma cells: production of RD-pheomelanin and covalent binding with thiol proteins
    • Ito S., Okura M., Nakanishi Y., Ojika M., Wakamatsu K., Yamashita T. Tyrosinase-catalyzed metabolism of rhododendrol (RD) in B16 melanoma cells: production of RD-pheomelanin and covalent binding with thiol proteins. Pigm. Cell Melanoma Res. 2015, 28:296-306.
    • (2015) Pigm. Cell Melanoma Res. , vol.28 , pp. 296-306
    • Ito, S.1    Okura, M.2    Nakanishi, Y.3    Ojika, M.4    Wakamatsu, K.5    Yamashita, T.6
  • 13
    • 3142624687 scopus 로고    scopus 로고
    • Occupational leukoderma in workers engaged in 4-(p-hydroxyphenyl)-2-butanone manufacturing
    • Fukuda Y., Nagano M., Futatsuka M. Occupational leukoderma in workers engaged in 4-(p-hydroxyphenyl)-2-butanone manufacturing. J. Occup. Health 1998, 40:118-122.
    • (1998) J. Occup. Health , vol.40 , pp. 118-122
    • Fukuda, Y.1    Nagano, M.2    Futatsuka, M.3
  • 14
    • 0014465018 scopus 로고
    • Hydroxyanisole depigmentation: in vivo studies
    • Riley P.A. Hydroxyanisole depigmentation: in vivo studies. J. Pathol. 1969, 97:185-191.
    • (1969) J. Pathol. , vol.97 , pp. 185-191
    • Riley, P.A.1
  • 15
    • 33749452223 scopus 로고    scopus 로고
    • Biochemical basis of 4-hydroxyanisole induced cell toxicity towards B16-F0 melanoma cells
    • Moridani M.Y. Biochemical basis of 4-hydroxyanisole induced cell toxicity towards B16-F0 melanoma cells. Cancer Lett. 2006, 243:235-245.
    • (2006) Cancer Lett. , vol.243 , pp. 235-245
    • Moridani, M.Y.1
  • 16
    • 0021800813 scopus 로고
    • Dermatitis produced by applications of monobenzone in patients with active vitiligo
    • Nordlund J.J., Forget B., Kirkwood J., Lerner A.B. Dermatitis produced by applications of monobenzone in patients with active vitiligo. Arch. Dermatol. 1985, 121:1141-1144.
    • (1985) Arch. Dermatol. , vol.121 , pp. 1141-1144
    • Nordlund, J.J.1    Forget, B.2    Kirkwood, J.3    Lerner, A.B.4
  • 17
    • 0017695235 scopus 로고
    • Occupational vitiligo induced by p-tert-butylphenol: a systemic disease?
    • James O., Mayes R.W., Stevenson C.J. Occupational vitiligo induced by p-tert-butylphenol: a systemic disease?. Lancet 1977, 2:1217-1219.
    • (1977) Lancet , vol.2 , pp. 1217-1219
    • James, O.1    Mayes, R.W.2    Stevenson, C.J.3
  • 18
    • 0014851302 scopus 로고
    • Depigmentation from 4-tertiary butyl catechol -an experimental study
    • Gellin G.A., Possick P.A., Perone V.B. Depigmentation from 4-tertiary butyl catechol -an experimental study. J. Invest. Dermatol. 1970, 55:190-197.
    • (1970) J. Invest. Dermatol. , vol.55 , pp. 190-197
    • Gellin, G.A.1    Possick, P.A.2    Perone, V.B.3
  • 19
    • 84907389925 scopus 로고    scopus 로고
    • Hydroquinone-induced depigmentation: case report and review of the literature
    • Jow T., Hantash B.M. Hydroquinone-induced depigmentation: case report and review of the literature. Dermatitis 2014, 25:e1-e5.
    • (2014) Dermatitis , vol.25 , pp. e1-e5
    • Jow, T.1    Hantash, B.M.2
  • 20
    • 84953320320 scopus 로고    scopus 로고
    • Natural, semisynthetic and synthetic tyrosinase inhibitors
    • Lee S.Y., Baek N., Nam T.G. Natural, semisynthetic and synthetic tyrosinase inhibitors. J. Enzyme Inhib. Med. Chem. 2015, (16 Feb):1-13.
    • (2015) J. Enzyme Inhib. Med. Chem. , Issue.16 FEB , pp. 1-13
    • Lee, S.Y.1    Baek, N.2    Nam, T.G.3
  • 21
    • 0030076508 scopus 로고    scopus 로고
    • Arbutin: mechanism of its depigmenting action in human melanocyte culture
    • Maeda K., Fukuda M. Arbutin: mechanism of its depigmenting action in human melanocyte culture. J. Pharmacol. Exp. Ther. 1996, 276:765-769.
    • (1996) J. Pharmacol. Exp. Ther. , vol.276 , pp. 765-769
    • Maeda, K.1    Fukuda, M.2
  • 22
    • 29344460420 scopus 로고    scopus 로고
    • Inhibitory effect of an ellagic acid-rich pomegranate extract on tyrosinase activity and ultraviolet-induced pigmentation
    • Yoshimura M., Watanabe Y., Kasai K., Yamakoshi J., Koga T. Inhibitory effect of an ellagic acid-rich pomegranate extract on tyrosinase activity and ultraviolet-induced pigmentation. Biosci. Biotechnol. Biochem. 2005, 69:2368-2373.
    • (2005) Biosci. Biotechnol. Biochem. , vol.69 , pp. 2368-2373
    • Yoshimura, M.1    Watanabe, Y.2    Kasai, K.3    Yamakoshi, J.4    Koga, T.5
  • 24
    • 84962954513 scopus 로고    scopus 로고
    • A novel approach for whitening with potassium 4-methoxysalicylate
    • (in Japanese)
    • Fujiwara R., Yoshida Y., Aoki H., Sato K. A novel approach for whitening with potassium 4-methoxysalicylate. Fragrance J. 2008, 9:37-41. (in Japanese).
    • (2008) Fragrance J. , vol.9 , pp. 37-41
    • Fujiwara, R.1    Yoshida, Y.2    Aoki, H.3    Sato, K.4
  • 25
    • 0042337124 scopus 로고    scopus 로고
    • Down-regulation of melanin synthesis by a biphenyl derivative and its mechanism
    • Nakamura K., Yoshida M., Uchiwa H., Kawa Y., Mizoguchi M. Down-regulation of melanin synthesis by a biphenyl derivative and its mechanism. Pigm. Cell Res. 2003, 16:494-500.
    • (2003) Pigm. Cell Res. , vol.16 , pp. 494-500
    • Nakamura, K.1    Yoshida, M.2    Uchiwa, H.3    Kawa, Y.4    Mizoguchi, M.5
  • 26
    • 0027476649 scopus 로고
    • Reactivity of orthoquinones involved in tyrosinase-dependent cytotoxicity: differences between alkylthio- and alkoxy-substituents
    • Cooksey C.J., Jimbow K., Land E.J., Riley P.A. Reactivity of orthoquinones involved in tyrosinase-dependent cytotoxicity: differences between alkylthio- and alkoxy-substituents. Melanoma Res. 1992, 2:283-293.
    • (1992) Melanoma Res. , vol.2 , pp. 283-293
    • Cooksey, C.J.1    Jimbow, K.2    Land, E.J.3    Riley, P.A.4
  • 27
    • 0037841882 scopus 로고    scopus 로고
    • Tyrosinase autoactivation and the chemistry of ortho-quinone amines
    • Land E.J., Ramsden C.A., Riley P.A. Tyrosinase autoactivation and the chemistry of ortho-quinone amines. Acc. Chem. Res. 2003, 36:300-308.
    • (2003) Acc. Chem. Res. , vol.36 , pp. 300-308
    • Land, E.J.1    Ramsden, C.A.2    Riley, P.A.3
  • 28
    • 0026641501 scopus 로고
    • Oxidative coupling of dichloroaluminium phenolates: highly selective synthesis of hydroxylated bi- and tetraaryls
    • Sartori G., Maggi R., Bigi F., Arienti A., Casnati G., Bocelli G., Mori G. Oxidative coupling of dichloroaluminium phenolates: highly selective synthesis of hydroxylated bi- and tetraaryls. Tetrahedron 1992, 48:9483-9494.
    • (1992) Tetrahedron , vol.48 , pp. 9483-9494
    • Sartori, G.1    Maggi, R.2    Bigi, F.3    Arienti, A.4    Casnati, G.5    Bocelli, G.6    Mori, G.7
  • 29
    • 84866239440 scopus 로고    scopus 로고
    • Synthesis of magnolignan, a new pigment lightening component, via a Suzuki-Miyaura reaction
    • 686242
    • Narita S., Ogura T., Usuki T. Synthesis of magnolignan, a new pigment lightening component, via a Suzuki-Miyaura reaction. J. Chem. 2013, 686242.
    • (2013) J. Chem.
    • Narita, S.1    Ogura, T.2    Usuki, T.3
  • 31
    • 0024257672 scopus 로고
    • Initial mushroom tyrosinase-catalysed oxidation product of 4-hydroxyanisole is 4-methoxy-ortho-benzoquinone
    • Naish S., Cooksey C.J., Riley P.A. Initial mushroom tyrosinase-catalysed oxidation product of 4-hydroxyanisole is 4-methoxy-ortho-benzoquinone. Pigm. Cell Res. 1988, 1:379-381.
    • (1988) Pigm. Cell Res. , vol.1 , pp. 379-381
    • Naish, S.1    Cooksey, C.J.2    Riley, P.A.3
  • 32
    • 68949127025 scopus 로고    scopus 로고
    • A reactive ortho-quinone generated by tyrosinase-catalyzed oxidation of the skin depigmenting agent monobenzone: self-coupling and thiol-conjugation reactions and possible implications for melanocyte toxicity
    • Manini P., Napolitano A., Westerhof W., Riley P.A., d'Ischia M. A reactive ortho-quinone generated by tyrosinase-catalyzed oxidation of the skin depigmenting agent monobenzone: self-coupling and thiol-conjugation reactions and possible implications for melanocyte toxicity. Chem. Res. Toxicol. 2009, 22:1398-1405.
    • (2009) Chem. Res. Toxicol. , vol.22 , pp. 1398-1405
    • Manini, P.1    Napolitano, A.2    Westerhof, W.3    Riley, P.A.4    d'Ischia, M.5
  • 33
    • 0343239102 scopus 로고    scopus 로고
    • Tyrosinase-mediated formation of a reactive quinone from the depigmenting agents, 4-tert-butylphenol and 4-tert-butylcatechol
    • Thörneby-Andersson K., Sterner O., Hansson C. Tyrosinase-mediated formation of a reactive quinone from the depigmenting agents, 4-tert-butylphenol and 4-tert-butylcatechol. Pigm. Cell Res. 2000, 13:33-38.
    • (2000) Pigm. Cell Res. , vol.13 , pp. 33-38
    • Thörneby-Andersson, K.1    Sterner, O.2    Hansson, C.3
  • 34
    • 0346558403 scopus 로고    scopus 로고
    • In vitro studies on the depigmenting activity of 4-(p-hydroxyphenyl)-2-butanone
    • Fukuda Y., Nagano M., Tsukamoto K., Futatsuka M. In vitro studies on the depigmenting activity of 4-(p-hydroxyphenyl)-2-butanone. J. Occup. Health 1998, 40:137-142.
    • (1998) J. Occup. Health , vol.40 , pp. 137-142
    • Fukuda, Y.1    Nagano, M.2    Tsukamoto, K.3    Futatsuka, M.4
  • 36
    • 0034040624 scopus 로고    scopus 로고
    • The cytotoxicity and apoptosis induced by 4-tertiary butylphenol in human melanocytes are independent of tyrosinase activity
    • Yang F., Sarangarajan R., Le Poole I.C., Medrano E.E., Boissy R.E. The cytotoxicity and apoptosis induced by 4-tertiary butylphenol in human melanocytes are independent of tyrosinase activity. J. Invest. Dermatol. 2000, 114:157-164.
    • (2000) J. Invest. Dermatol. , vol.114 , pp. 157-164
    • Yang, F.1    Sarangarajan, R.2    Le Poole, I.C.3    Medrano, E.E.4    Boissy, R.E.5
  • 40
    • 84899903650 scopus 로고    scopus 로고
    • Mechanistic aspects of the tyrosinase oxidation of hydroquinone
    • Ramsden C.A., Riley P.A. Mechanistic aspects of the tyrosinase oxidation of hydroquinone. Bioorg. Med. Chem. Lett. 2014, 24:2463-2464.
    • (2014) Bioorg. Med. Chem. Lett. , vol.24 , pp. 2463-2464
    • Ramsden, C.A.1    Riley, P.A.2
  • 41
    • 0038680412 scopus 로고    scopus 로고
    • Identification of oxidation product of arbutin in mushroom tyrosinase assay system
    • Nihei K., Kubo I. Identification of oxidation product of arbutin in mushroom tyrosinase assay system. Bioorg. Med. Chem. Lett. 2003, 13:2409-2412.
    • (2003) Bioorg. Med. Chem. Lett. , vol.13 , pp. 2409-2412
    • Nihei, K.1    Kubo, I.2
  • 43
    • 84873708098 scopus 로고    scopus 로고
    • Mechanistic studies of the inactivation of tyrosinase by resorcinol
    • Stratford M.R.L., Ramsden C.A., Riley P.A. Mechanistic studies of the inactivation of tyrosinase by resorcinol. Bioorg. Med. Chem. 2013, 21:1166-1173.
    • (2013) Bioorg. Med. Chem. , vol.21 , pp. 1166-1173
    • Stratford, M.R.L.1    Ramsden, C.A.2    Riley, P.A.3


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