Nicotinic acid hydroxamate downregulated the melanin synthesis and tyrosinase activity through activating the MEK/ERK and AKT/GSK3β signaling pathways

Journal of Agricultural and Food Chemistry

Volumn 60, Issue 19, 2012, Pages 4859-4864

  Lin, Yin Shiou ^a   Chuang, Mao Te ^b   Chen, Chao Hsiang ^c   Chien, Mei Yin ^c   Hou, Wen Chi ^a,d  

^a TAIPEI MEDICAL UNIVERSITY   (Taiwan)

^b ST MARTIN DE PORRES HOSPITAL   (Taiwan)

^c KO DA PHARMACEUTICAL CO LTD   (Taiwan)

^d TAIPEI MEDICAL UNIVERSITY HOSPITAL   (Taiwan)

Author keywords

extracellular signal regulated kinase (ERK); glycogen synthase kinase 3 (GSK3 ); melanogenesis; microphthalmia associated transcription factor (MITF); nicotinic acid hydroxamate (NAH); tyrosinase

Indexed keywords

EXTRACELLULAR SIGNAL-REGULATED KINASE; GLYCOGEN SYNTHASE KINASE-3; HYDROXAMATE; MELANOGENESIS; MICROPHTHALMIA-ASSOCIATED TRANSCRIPTION FACTOR (MITF); TYROSINASE;

PHOSPHORYLATION; TRANSCRIPTION FACTORS;

ENZYME ACTIVITY;

ENZYME INHIBITOR; GLYCOGEN SYNTHASE KINASE 3; GLYCOGEN SYNTHASE KINASE 3 BETA; MELANIN; MITOGEN ACTIVATED PROTEIN KINASE KINASE; MONOPHENOL MONOOXYGENASE; NICOTINIC ACID; ONCOPROTEIN;

ANIMAL; ARTICLE; BIOSYNTHESIS; CHEMISTRY; DOWN REGULATION; DRUG ANTAGONISM; DRUG EFFECT; GENETICS; HUMAN; METABOLISM; MOUSE; SIGNAL TRANSDUCTION; TUMOR CELL LINE;

ANIMALS; CELL LINE, TUMOR; DOWN-REGULATION; ENZYME INHIBITORS; GLYCOGEN SYNTHASE KINASE 3; HUMANS; MAP KINASE SIGNALING SYSTEM; MELANINS; MICE; MITOGEN-ACTIVATED PROTEIN KINASE KINASES; MONOPHENOL MONOOXYGENASE; NIACIN; ONCOGENE PROTEIN V-AKT;

MURINAE;

EID: 84861121315     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf301109p     Document Type: Article

References (30)

1. Boissy, R. E. Melanosome transfer to and translocation in the keratinocyte Exp. Dermatol. 2003, 12 (Suppl. 2) 5-12
2. Gilchrest, B. A.; Park, H. Y.; Eller, M. S.; Yaar, M. Mechanisms of ultraviolet light-induced pigmentation Photochem. Photobiol. 1996, 63, 1-10
3. Hearing, V. J.; Tsukamoto, K. Enzymatic control of pigmentation in mammals FASEB J. 1991, 5, 2902-2909
4. Steingrimsson, E.; Copeland, N. G.; Jenkins, N. A. Melanocytes and the microphthalmia transcription factor network Annu. Rev. Genet. 2004, 38, 365-411
5. Busca, R.; Ballotti, R. Cyclic AMP a key messenger in the regulation of skin pigmentation Pigment Cell Res. 2000, 13, 60-69
6. Halaban, R.; Pomerantz, S. H.; Marshall, S.; Lambert, D. T.; Lerner, A. B. Regulation of tyrosinase in human melanocytes grown in culture J. Cell Biol. 1983, 97, 480-488
7. Hunt, G.; Todd, C.; Cresswell, J. E.; Thody, A. J. Alpha-melanocyte stimulating hormone and its analogue Nle4DPhe7 alpha-MSH affect morphology, tyrosinase activity and melanogenesis in cultured human melanocytes J. Cell Sci. 1994, 107 (Part 1) 205-211
8. Kono, M.; Dunn, I. S.; Durda, P. J.; Butera, D.; Rose, L. B.; Haggerty, T. J.; Benson, E. M.; Kurnick, J. T. Role of the mitogen-activated protein kinase signaling pathway in the regulation of human melanocytic antigen expression Mol. Cancer Res. 2006, 4, 779-792
9. Oka, M.; Nagai, H.; Ando, H.; Fukunaga, M.; Matsumura, M.; Araki, K.; Ogawa, W.; Miki, T.; Sakaue, M.; Tsukamoto, K. Regulation of melanogenesis through phosphatidylinositol 3-kinase-Akt pathway in human G361 melanoma cells J. Invest. Dermatol. 2000, 115, 699-703
10. Kobashi, K.; Kumaki, K.; Hase, J. I. Effect of acyl residues of hydroxamic acids on urease inhibition Biochim. Biophys. Acta 1971, 227, 429-441
11. Lin, Y. S.; Chen, S. H.; Huang, W. J.; Chen, C. H.; Chien, M. Y.; Lin, S. Y.; Hou, W. C. Effects of nicotinic acid derivatives on tyrosinase inhibitory and antioxidant activities Food Chem. 2012, 132, 2074-2080
12. Rich, P. R.; Wiegand, N. K.; Blum, H.; Moore, A. L.; Bonner, W. D., Jr. Studies on the mechanism of inhibition of redox enzymes by substituted hydroxamic acids Biochim. Biophys. Acta, Enzymol. 1978, 525, 325-337
13. Rho, H.; Baek, H.; Ahn, S.; Yoo, J.; Kim, D.; Kim, H. Hydroxamic acid derivatives as anti-melanogenic agents: the importance of a basic skeleton and hydroxamic acid moiety Bull. Korean Chem. Soc. 2009, 30, 475-478
14. Apfel, C.; Banner, D. W.; Bur, D.; Dietz, M.; Hirata, T.; Hubschwerlen, C.; Locher, H.; Page, M. G.; Pirson, W.; Rosse, G.; Specklin, J. L. Hydroxamic acid derivatives as potent peptide deformylase inhibitors and antibacterial agents J. Med. Chem. 2000, 43, 2324-2331
15. Holland, K. P.; Elford, H. L.; Bracchi, V.; Annis, C. G.; Schuster, S. M.; Chakrabarti, D. Antimalarial activities of polyhydroxyphenyl and hydroxamic acid derivatives Antimicrob. Agents Chemother. 1998, 42, 2456-2458
16. Scott, G.; Leopardi, S. The cAMP signaling pathway has opposing effects on Rac and Rho in B16F10 cells: implications for dendrite formation in melanocytic cells Pigment Cell Res. 2003, 16, 139-148
17. Seamon, K. B.; Padgett, W.; Daly, J. W. Forskolin: unique diterpene activator of adenylate cyclase in membranes and in intact cells Proc. Natl. Acad. Sci. U.S.A. 1981, 78, 3363-3367
18. Yasumoto, K.; Yokoyama, K.; Takahashi, K.; Tomita, Y.; Shibahara, S. Functional analysis of microphthalmia-associated transcription factor in pigment cell-specific transcription of the human tyrosinase family genes J. Biol. Chem. 1997, 272, 503-509
19. Englaro, W.; Bertolotto, C. Inhibition of the mitogen-activated protein kinase pathway triggers B16 melanoma cell differentiation J. Biol. Chem. 1998, 273, 9966-9970
20. Khaled, M.; Larribere, L.; Bille, K.; Aberdam, E.; Ortonne, J.; Ballotti, R.; Bertolotto, C. Glycogen synthase kinase 3β is activated by cAMP and plays an active role in the regulation of melanogenesis J. Biol. Chem. 2002, 277, 33690-33697
21. Jin, S.; Lee, Y.; Kang, H. Methyl-β-cyclodextrin, a specific cholesterol-binding agent, inhibits melanogenesis in human melanocytes through activation of ERK Arch. Dermatol. Res. 2008, 300, 451-454
22. Kim, D. S.; Kim, S. Y.; Lee, J. E.; Kwon, S. B.; Joo, Y. H.; Youn, S. W.; Park, K. C. Sphingosine-1-phosphate-induced ERK activation protects human melanocytes from UVB-induced apoptosis Arch. Pharmacal Res. 2003, 26, 739-746
23. Kim, J.; Baek, S.; Kim, D.; Choi, T.; Yoon, T.; Hwang, J.; Kim, M.; Kwon, H.; Lee, C. Downregulation of melanin synthesis by haginin A and its application to in vivo lightening model J. Invest. Dermatol. 2007, 128, 1227-1235
24. Wu, M.; Hemesath, T.; Takemoto, C.; Horstmann, M.; Wells, A.; Price, E.; Fisher, D.; Fisher, D. c-Kit triggers dual phosphorylations, which couple activation and degradation of the essential melanocyte factor Mi Genes Dev. 2000, 14, 301-312
25. Sato, S.; Roberts, K.; Gambino, G.; Cook, A.; Kouzarides, T.; Goding, C. CBP/p300 as a co-factor for the Microphthalmia transcription factor Oncogene 1997, 14, 3083-3092
26. Busca, R.; Bertolotto, C.; Ortonne, J.; Ballotti, R. Inhibition of the phosphatidylinositol 3-kinase/p70S6-kinase pathway induces B16 melanoma cell differentiation J. Biol. Chem. 1996, 271, 31824-31830
27. Lau, S.; Monks, T.; Everitt, J.; Kleymenova, E.; Walkers, C. Carcinogenicity of a nephrotoxic metabolite of the "nongenotoxic" carcinogen hydroquinone Chem. Res. Toxicol. 2001, 14, 25-33
28. Sugihara, K.; Tatsumi, K. Participation of liver aldehyde oxidase in reductive metabolism of hydroxamic acids to amides Arch. Biochem. Biophys. 1986, 247, 289-293
29. Harada, K.; Murawaki, Y.; Hirayama, C. Comparative studies of nicotinohydroxamic acid and neomycin on ammonia and urea metabolism in rats Res. Commun. Chem. Pathol. Pharmacol. 1985, 49, 309-312
30. Hirayama, C.; Ichida, F.; Takahashi, Y.; Koizumi, T.; Sato, S.; Kosaka, Y.; Wakui, K.; Shimada, Y.; Yoshiba, A.; Hattori, N. A controlled clinical trial of nicotinohydroxamic acid and neomycin in advanced chronic liver disease Digestion 1982, 25, 115-123