Benzylamide derivative compound attenuates the ultraviolet B-induced hyperpigmentation in the brownish guinea pig skin

Biochemical Pharmacology

Volumn 67, Issue 4, 2004, Pages 707-715

  Choi, Sang Yoon ^a   Kim, Sanghee ^b   Hwang, Jae Sung ^c   Lee, Byeong Gon ^c   Kim, Hocheol ^a   Kim, Sun Yeou ^a  

^a Kyung Hee University   (South Korea)

^b Seoul National University   (South Korea)

^c AmorePacific Corporation   (South Korea)

Author keywords

Benzylamide; Melanogenesis; Whitening agents

Indexed keywords

2,6 DIMETHOXY N PHENYLBENZAMIDE; 5,6 DIHYDROXYINDOLE 2 CARBOXYLIC ACID; BENZAMIDE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; DOPACHROME; DOPACHROME TAUTOMERASE; MELANIN; MONOPHENOL MONOOXYGENASE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CATALYSIS; CELL CULTURE; CONTROLLED STUDY; DRUG EFFECT; DRUG SCREENING; ENZYME ACTIVATION; EXPERIMENT; GUINEA PIG; HUMAN; HUMAN CELL; HYPERPIGMENTATION; IMMUNOHISTOCHEMISTRY; IN VITRO STUDY; INHIBITION KINETICS; LIGHT; MELANOCYTE; MELANOGENESIS; METHODOLOGY; NONHUMAN; PRIORITY JOURNAL; PROTEIN FUNCTION; SKIN PIGMENTATION; STAINING; STIMULATION; ULTRAVIOLET B RADIATION;

EID: 1642493656     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bcp.2003.09.045     Document Type: Article

References (29)

1. Korner A., Pawelek J. Mammalian tyrosinase catalases three reactions in the biosynthesis of melanin. Science. 217:1982;1163-1165.
2. Pawelek J.M. After dopachrome? Pigment Cell Res. 4:1991;53-62.
3. Chen J.S., Wei C., Marshall M.R. Inhibition mechanism of kojic acid on polyphenol oxidase. J. Agric. Food Chem. 39:1991;1897-1901.
4. Maeda K., Fukuda M. In vivo effectiveness of several whitening cosmetic components in human melanocytes. J. Soc. Cosmet. Chem. 42:1991;361-368.
5. Ernest V.C., Cecil K., Heino H., Hansruedi G., Chie S., Victoria V., Vincent J.H.J., Thomas P.D. Inhibitors of mammalian melanocyte tyrosinase: in vitro comparisons of alkyl esters of gentisic acid with other putative inhibitors. Biochem. Pharmacol. 57:1999;663-672.
6. Iozumi K., Hoganson G.E., Pemella R., Everett M.A., Fuller B.B. Role of tyrosinase as the determinant of pigmentation in cultured human melanocytes. J. Invest. Dermatol. 100:1993;806-811.
7. Aroca P., Urabe K., Kobayashi T., Tsukamoto K., Hearing V.J. Melanin biosynthesis patterns following hormonal stimulation. J. Biol. Chem. 268:1993;25650-25655.
8. Shin N.H., Ryu S.Y., Choi E.J., Kang S.H., Chang I.M., Min K.R., Kim Y.S. Oxyresveratrol as potent inhibitor on dopa oxidase activity of mushroom tyrosinase. Biochem. Biophys. Res. Commun. 243:1998;801-803.
9. Kim Y.M., Yun J., Lee C.K., Lee H., Min K.R., Kim Y.S. Oxyresveratrol and hydrostilbene compounds: inhibitory effect on tyrosinase and mechanism of action. J. Biol. Chem. 277:2002;16340-16344.
10. Gomez-Cordoves C., Bartolome B., Vieira W., Virador V.M. Effects of wine phenolics and sorghum tannins on tyrosinase activity and growth of melanoma cells. J. Agric. Food Chem. 49:2001;1620-1624.
11. Borger D., Jiang W., Goldberg J. Convergent solution-phase combinatorial synthesis with multiplication of diversity though rigid biaryl and diarylacetylene couplings. J. Org. Chem. 64:1999;7094-7100.
12. Oka M., Ogita K., Ando H., Horikawa T., Hayashibe K., Saito N., Kikkawa U., Ichihashi M. Deletion of specific protein kinase C subspecies in human melanoma cells. J. Cell. Physiol. 167:1996;406-412.
13. Fuller B.B., Drake M.A., Spaulding D.T., Chaudhry F. Downregulation of tyrosinase activity in human melanocyte cell culture by yohimbine. J. Invest. Dermatol. 114:2000;268-276.
14. Shono S, Toda K. The effect of fatty acids on tyrosinase activity. In: Seiji M, editor. Pigment cell. Tokyo: University of Tokyo Press; 1981. p. 263-8.
15. Barber J., Townsend D., David P., Olds M.S., King R.A. Dopachrome oxidoreductase: a new enzyme in the pigment pathway. J. Invest. Dermatol. 83:1984;145-149.
16. Wright S. Dietary supplementation with n - 6 essential fatty acids in atopic eczema. J. Dermatol. Treat. 1:1990;47-49.
17. Hosoi J., Abe E., Suda T., Kuroki T. Regulation of melanin synthesis of B16 mouse melanoma cells by 1,2,5-dihydroxy vitamin D and retinoic acid. Cancer Res. 45:1985;1474-1478.
18. Poma A., Bianchini S., Miranoa M. Inhibition of L-tyrosine-induced micronuclei production by phenylthiourea in human melanoma cells. Mutat. Res. 446:1999;143-148.
19. Nordlund, Boissy, Hearing, King, Ortonne. The pigmentary system. Oxford University Press; 1998. p. 406.
20. Hideya A., Atsuko R., Akira H., Masahiro O., Masamitsu I. Linoleic acid and α-linoleic acid lightens ultraviolet-induced hyperpigmentation of the skin. Arch. Dermatol. Res. 290:1998;375-381.
21. Imokawa G., Kawai M., Mishima Y., Motegi I. Differential analysis of experimental hypermelanogenesis induced by UVB, PUVA and allergic dermatitis using a brownish guinea pig model. Arch. Dermatol. Res. 278:1986;352-362.
22. Ludger K., Albert M.K., Tracy S. The sodium hydroxide erosion assay: a revision of alkali resistance test. Arch. Dermatol. Res. 290:1998;382-387.
23. Alonso E., Ramon D., Yus M. Simple synthesis of 5-substituted resorcinols. J. Org. Chem. 62:1997;417-421.
24. Zang J., Doi W., Ronald G. Synthesis of higher oxidized metabolites of dibenz[a,j]anthracene implicated in the mechanism of carcinogenesis. J. Org. Chem. 63:1998;8125-8132.
25. Aroca P., Solano F., Jose C., Borron G., Lozano J.A. A new spectrophotometric assay for dopachrome tautomerase. J. Biochem. Biophys. Methods. 21:1990;35-46.
26. Bennett D., Cooper P., Hart I. A line of non-tumorigenic mouse melanocytes, syngeneic with the B16 melanoma and requiring a tumour promoter for growth. Int. J. Cancer. 39:1987;414-418.
27. Sugumaran M. Comparative biochemistry of eumelanogenesis and the protective roles of phenoloxidase and melanin in insects. Pigment Cell Res. 15:2002;2-9.
28. Jose H., Solano F., Jose C., Borron G., Jose R., Jose A. α-MSH and other melanogenic activators mediate opposite effects on tyrosinase and dopachrome tautomerase in B16/F10 mouse melanoma cells. J. Invest. Dermatol. 99:1992;435-439.
29. Fang J., Han Q., Johnson J.K., Christensen B.M., Li J. Functional expression and characterization of Aedes aegypi dopachrome conversion enzyme. Biochem. Biophys. Res. Commun. 290:2002;287-293.