Generation mechanism of radical species by tyrosine-tyrosinase reaction

Journal of Clinical Biochemistry and Nutrition

Volumn 47, Issue 2, 2010, Pages 162-166

  Tada, Mika ^a,b   Kohno, Masahiro ^a   Kasai, Shigenobu ^b   Niwano, Yoshimi ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b TOHOKU INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Radical species; Tyrosinase; Tyrosine

Indexed keywords

5,5 DIMETHYL 1 PYRROLINE 1 OXIDE; CATALASE; DEUTERIUM; FERROUS GLUCONATE; MONOPHENOL MONOOXYGENASE; SOLVENT; TYROSINE; WATER;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; ELECTRON SPIN RESONANCE; ELECTRON TRANSPORT; ENZYME MECHANISM; OXIDATIVE STRESS;

EID: 77956585169     PISSN: 09120009     EISSN: None     Source Type: Journal    
DOI: 10.3164/jcbn.10-48     Document Type: Article

References (28)

1. Brash, D.E., Ziegler, A., Jonason, A.S., Simon, J.A., Kunala, S., and Leffell, D.J.: Sunlight and sunburn in human skin cancer: p53, apoptosis, and tumor promotion. J. Investig. Dermatol. Symp. Proc., 1, 136-142, 1996.
2. Wikonkal, N.M. and Brash, D.E.: Ultraviolet radiation signature mutations in photocarcinogenseis. J. Investig. Dermatol. Symp. Proc., 4, 6-10, 1999.
3. Mckay, B.C., Stubbert, L.J., Fowler, C.C., Smith, J.M., Cardamore, R.A., and Spronck, J.C.: Regulation of ultraviolet light-induced gene expression by gene size. Proc. Natl. Acad. Sci. U.S.A., 101, 6582-6586, 2004.
4. Agar, N.S., Halliday, G.M., Barnetson, R.S., Ananthaswamy, H.N., Wheeler, M., and Jones, A.M.: The basal layer in human squamous tumors harbors more UVA than UVB fingerprint mutations: a role for UVA in human skin carcinogenesis. Proc. Natl. Acad. Sci. U.S.A., 101, 4954-4959, 2004.
5. Brenner, D.J., Doll, R., Goodhead, D.T., Hall, E.J., Land, C.E., Little, J.B., Lubin, J.H., Preston, D.L., Preston, R.J., Puskin, J.S., Ron, E., Sachs, R.K., Samet, J.M., Setlow, R.B., and Zaider, M.: Cancer risks attributable to low does of ionizing radiation: assessing what really know. Proc. Natl. Acad. Sci. U.S.A., 100, 13761-13766, 2003.
6. Setlow, R.B.: Spectral regions contributing to melanoma: a personal view. J. Investig. Dermatol. Symp. Proc., 4, 46-49, 1999.
7. Moan, J., Dahlback, A., and Setlow, R.B.: Epidemiological support for an hypothesis for melanoma induction indicating a role for UVA radiation. Photochem. Photobiol., 70, 243-247, 1999.
8. Hunt, G., Kyne, S., Ito, S., Wakamatsu, K., Todd, C., and Thody, A.: Eumelanin and pheomelanin contents of human epidermis and cultured melanocytes. Pigment Cell Res., 8, 202-208, 1995.
9. Vincensi, M.R., d'Ischia, M., Napolitano, A., Procaccini, E.M., Riccio, G., Monfrecola, G., Santoianni, P., and Prota, G.: Pheomelanin versus eumelanin as a chemical indicator of ultraviolet sensitivity in fair-skinned subjects at high risk for melanoma: a pilot study. Melanoma Res., 8, 53-58, 1998.
10. Kvam, E. and Dahle, J.: Pigmented melanocytes are protected against ultraviolet-A-induced membrane damage. J. Investig. Dermatol., 121, 564-569, 2003.
11. Yamazaki, F., Okamoto, H., Miyauchi-Hashimoto, H., Matsumura, Y., Itoh, T., Tanaka, K., Kunisada, T., and Horio, T.: XPA gene-deficient, SCF-transgenic mice with epidermal melanin are resistant to UV-induced carcinogenesis. J. Investig. Dermatol., 123, 220-228, 2004.
12. Wagner, J.K., Parra, E.J., Norton, H.L., Jovel, C., and Shriver, M.D.: Skin responses to ultraviolet radiation: effects of constitutive pigmentation, sex, and ancestry. Pigment Cell Res., 15, 385-390, 2002.
13. Ortonne, J.P.: Photoprotective properties of skin melanin. Br. J. Dermatol., 146, 7-10, 2002.
14. Yamaguchi, Y., Takahashi, K., Zmudzka, B.Z., Kornhauser, A., Miller, S.A., Tadokoro, T., Berens, W., Beer, J.Z., and Hearing, V.J.: Human skin responses to UV radiation: pigment in the upper epidermis protects against DNA damage in the lower epidermis and facilitates apoptosis. FASEB. J., 20, 1486-1488, 2006.
15. Tada, M., Kohno, M., and Niwano, Y.: Scavenging or quenching effect of melanin on superoxide anion and singlet oxygen. J. Clin. Biochem. Nutr., 46, 224-228, 2010.
16. Ito, S. and K. Wakamatsu, K.: Chemistry of mixed melanogenesis - pivotal roles of dopaquinone. Photochem. Photobiol., 84, 582-592, 2008.
17. Khazaeli, P., Goldoozian, R., and Sharififar, F.: An evaluation of extracts of five traditional medicinal plants from Iran on the inhibition of mushroom tyrosinase activity and scavenging of free radicals. Int. J. Cosmet. Sci., 31, 375-381, 2009.
18. Momtaz, S., Mapunya, B.M., Houghton, P.J., Edgerly, C., Hussein, A., Naidoo, S., and Lall, N.: Tyrosinase inhibition by extracts and constituents of Sideroxylon inerme L. stem bark, used in South Africa for skin lightening. J. Ethnopharmacol., 119, 507-512, 2008.
19. Ng, L.T., Ko, H.H., and Lu, T.M.: Potential antioxidants and tyrosinase inhibitors from synthetic polyphenolic deoxybenzoins. Bioorg. Med. Chem., 17, 4360-4366, 2009.
20. Nugroho, A., Choi, J.K., Park, J.H., Lee, K.T., Cha, B.C., and Park, H.J.: Two new flavonol glycosides from Lamium amplexicaule L. and their in vitro free radical scavenging and tyrosinase inhibitory activities. Planta. Med., 75, 364-366, 2009.
21. Wang, K.H., Lin, R.D., Hsu, F.L., Huang, Y.H., Chang, H.C., Huang, C.Y., and Lee, M.H.: Cosmetic applications of selected traditional Chinese herbal medicines. J. Ethnopharmacol., 106, 353-359, 2006.
22. Inoue, T., Shiota, Y., and Yoshizawa, K.: Quantum chemical approach to the mechanism for the biological conversion of tyrosine to dopaquinone. J. Am. Chem. Soc., 130, 16890-16897, 2008.
23. Chen, P. and Solomon, E.I.: O2 activation by binuclear Cu sites: noncoupled verus exchange coupled reaction mechanisms. Pros. Natl. Acad. Sci. U.S.A., 101, 13105-13110, 2004.
24. Solomon, E.I., Chen, P., Metz, M., Lee, S.K., and Palmer, A.E.: Oxygen binding, activation, and reduction to water by copper proteins. Angew. Chem. Int. Ed. Engl., 40, 4570-4590, 2001.
25. Usui, N. and Sinha, B.K.: Tyrosinase-induced free radical formation from VP-16,213: relationship to cytotoxicity. Free Radic. Res. Commun., 10, 287-293, 1990.
26. Tomita, Y., Hariu, A., Kato, C., and Seiji, M.: Radical production during tyrosinase reaction, dopa-melanin formation, and photoirradiation of dopa-melanin. J. Investig. Dermatol., 82, 573-576, 1984.
27. Buettner, G.R.: Spin trapping: ESR parameters of spin adducts. Free Radic. Biol. Med., 3, 259-303, 1987.
28. Zhu, Q., Lian, Y., Thyagarajan, S., Rokita, S.E., Karlin, K.D., and Blough, N.V.: Hydrogen peroxide and dioxygen activation by dinuclear copper complexes in aqueous solution: hydroxyl radical production initiated by internal electron transfer. J. Am. Chem. Soc., 130, 6304-6305, 2008.