Zinc-induced structural effects enhance oxygen consumption and superoxide generation in synthetic pheomelanins on UVA/visible light irradiation

Photochemistry and Photobiology

Volumn 86, Issue 4, 2010, Pages 757-764

  Panzella, Lucia ^a   Szewczyk, Grzegorz ^b   D'Ischia, Marco ^a   Napolitano, Alessandra ^a   Sarna, Tadeusz ^b  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^b JAGIELLONIAN UNIVERSITY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

MELANIN; OXYGEN; PHEOMELANIN; SUPEROXIDE; ZINC;

CHEMICAL STRUCTURE; CHEMISTRY; CONFERENCE PAPER; ELECTRON SPIN RESONANCE; HUMAN; LIGHT; SYNTHESIS;

ELECTRON SPIN RESONANCE SPECTROSCOPY; HUMANS; LIGHT; MELANINS; MOLECULAR STRUCTURE; OXYGEN; SUPEROXIDES; ZINC;

EID: 77954421522     PISSN: 00318655     EISSN: 17511097     Source Type: Journal    
DOI: 10.1111/j.1751-1097.2010.00726.x     Document Type: Conference Paper

References (47)

1. Miyamura, Y., S. G. Coelho, R. Wolber, S. A. Miller, K. Wakamatsu, B. Z. Zmudzka, S. Ito, C. Smuda, T. Passeron, W. Choi, J. Batzer, Y. Yamaguchi, J. Z. Beer V. J. Hearing (2007) Regulation of human skin pigmentation and responses to ultraviolet radiation. Pigment Cell Res. 20, 2 13.
2. Wenczl, E., G. P. Van der Schans, L. Roza, R. M. Kolb, A. J. Timmerman, N. P. Smit, S. Pavel A. A. Schothorst (1998) (Pheo)melanin photosensitizes UVA-induced DNA damage in cultured human melanocytes. J. Invest. Dermatol. 11, 678 682.
3. Bliss, J. M., D. Ford, A. J. Swerdlow, B. K. Armstrong, M. Cristofolini, J. M. Elwood, A. Green, E. A. Holly, T. Mack, R. M. MacKie, A. Osterlind, S. D. Walter, J. Peto D. F. Easton (1995) Risk of cutaneous melanoma associated with pigmentation characteristics and freckling: Systematic overview of 10-case-control studies. Int. J. Cancer 62, 367 376.
4. Vincensi, M. R., M. d'Ischia, A. Napolitano, E. Procaccini, G. Riccio, G. Monfrecola, P. Santoianni G. Prota (1998) 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.
5. Gandini, S., F. Sera, M. S. Cattaruzza, P. Pasquini, R. Zanetti, C. Masini, P. Boyle C. F. Melchi (2005) Meta-analysis of risk factors for cutaneous melanoma: III. Family history, actinic damage and phenotypic factors. Eur. J. Cancer 41, 2040 2059.
6. Chedekel, M. R., S. K. Smith, P. W. Post, A. Pokora D. L. Vessell (1978) Photodestruction of pheomelanin: Role of oxygen. Proc. Natl Acad. Sci. USA 75, 5395 5399.
7. Ye, T. J. D. Simon (2002) Ultrafast spectroscopic study of pheomelanin: Implications on the mechanism of superoxide anion formation. J. Phys. Chem. B 106, 6133 6135.
8. Sarna, T., I. A. Menon R. C. Sealy (1984) Photoinduced oxygen consumption in melanin systems - II. Action spectra and quantum yields for pheomelanins. Photochem. Photobiol. 39, 805 809.
9. Ye, T., L. Hong, J. Garguilo, A. Pawlak, G. S. Edwards, R. J. Nemanich, T. Sarna J. D. Simon (2006) Photoionization thresholds of melanins obtained from free electron laser-photoelectron emission microscopy, femtosecond transient absorption spectroscopy and electron paramagnetic resonance measurements of oxygen photoconsumption. Photochem. Photobiol. 82, 733 737.
10. Ye, T., A. Pawlak, T. Sarna J. D. Simon (2008) Different molecular constituents in pheomelanin are responsible for emission, transient absorption and oxygen photoconsumption. Photochem. Photobiol. 84, 437 443.
11. Ye, T., L. E. Lamb, K. Wakamatsu, S. Ito J. D. Simon (2003) Ultrafast absorption and photothermal studies of decarboxytrichochrome C in solution. Photochem. Photobiol. Sci. 2, 821 823.
12. Simon, J. D., M. R. Goldsmith, L. Hong, V. R. Kempf, L. E. McGuckin, T. Ye G. Zuber (2006) Spectroscopy and photoreactivity of trichochromes: Molecular components of pheomelanins. Photochem. Photobiol. 82, 318 323.
13. Liu, Y., L. Hong, K. Wakamatsu, S. Ito, B. Adhyaru, C. Y. Cheng, C. R. Bowers J. D. Simon (2005) Comparison of structural and chemical properties of black and red human hair melanosomes. Photochem. Photobiol. 81, 135 144.
14. Napolitano, A., P. Di Donato G. Prota (2001) Zinc-catalyzed oxidation of 5-S-cysteinyldopa to 2,2′-bi(2H-1,4-benzothiazine): Tracking the biosynthetic pathway of trichochromes, the characteristic pigments of red hair. J. Org. Chem. 66, 6958 6966.
15. Napolitano, A., M. De Lucia, L. Panzella M. d'Ischia (2008) The "benzothiazine" chromophore of pheomelanins: A reassessment. Photochem. Photobiol. 84, 593 599.
16. Chioccara, F. E. Novellino (1986) A convenient one step synthesis of 5-cystein-S-yldopa using cerium ammonium nitrate. Synth. Commun. 16, 967 971.
17. Panzella, L., M. De Lucia, A. Napolitano M. d'Ischia (2007) The first expedient entry to the human melanogen 2-S-cysteinyldopa exploiting the anomalous regioselectivity of 3,4-dihydroxycinnamic acid-thiol conjugation. Tetrahedron Lett. 48, 7650 7652.
18. Greco, G., L. Panzella, A. Napolitano M. d'Ischia (2009) Biologically inspired one-pot access routes to 4-hydroxybenzothiazole amino acids, red hair-specific markers of UV susceptibility and skin cancer risk. Tetrahedron Lett. 50, 3095 3097.
19. Napolitano, A., M. R. Vincensi, P. Di Donato, G. Monfrecola G. Prota (2000) Microanalysis of melanins in mammalian hair by alkaline hydrogen peroxide degradation: Identification of a new structural marker of pheomelanins. J. Invest. Dermatol. 114, 1141 1147.
20. Ito, S. (1989) Optimization of conditions for preparing synthetic pheomelanin. Pigment Cell Res. 2, 53 56.
21. Liu, Y., L. Hong, V. R. Kempf, K. Wakamatsu, S. Ito J. D. Simon (2004) Ion-exchange and adsorption of Fe(III) by Sepia melanin. Pigment Cell Res. 17, 262 269.
22. Halpern, H. J., M. Peric, T. D. Nguyen, D. P. Spencer, B. A. Teicher, Y. J. Lin M. K. Bowman (1990) Selective isotopic labeling of a nitroxide spin label to enhance sensitivity for T2 oxymetry. J. Magn. Reson. 90, 40 51.
23. Sarna, T., A. Duleba, W. Korytowski A. Swartz (1980) Interaction of melanin with oxygen. Arch. Biochem. Biophys. 200, 140 148.
24. Rosen, G. M. E. Finkelstein (1985) Use of spin traps in biological systems. Adv. Free Radic. Biol. Med. 1, 345 375.
25. Panzella, L., P. Manini, G. Monfrecola, M. d'Ischia A. Napolitano (2007) An easy-to-run method for routine analysis of eumelanin and pheomelanin in pigmented tissues. Pigment Cell Res. 20, 128 133.
26. Napolitano, A., C. Costantini, O. Crescenzi G. Prota (1994) Characterisation of 1,4-benzothiazine intermediates in the oxidative conversion of 5-S-cysteinyldopa to pheomelanins. Tetrahedron Lett. 35, 6365 6368.
27. Napolitano, A., S. Memoli, O. Crescenzi G. Prota (1996) Oxidative polymerization of the pheomelanin precursor 5-hydroxy-1,4-benzothiazinylalanine: A new hint to the pigment structure. J. Org. Chem. 61, 598 604.
28. Buettner, G. R. (1987) Spin trapping: ESR parameters of spin adducts. Free Radic. Biol. Med. 3, 259 303.
29. Rózanowska, M., J. Jarvis-Evans, W. Korytowski, M. E. Boulton, J. M. Burke T. Sarna (1995) Blue light-induced reactivity of retinal age pigment. In vitro generation of oxygen-reactive species. J. Biol. Chem. 270, 18825 18830.
30. Li, A. S. W., K. B Cummings, H. P. Roethling, G. R. Buettner C. F. Chignell (1988) A spin trapping data base implemented on the IBM PC/AT. J. Magn. Reson. 79, 140 142.
31. Roberts, J. E., J. F. Wishart, L. Martinez C. F. Chignell (2000) Photochemical studies on xanthurenic acid. Photochem. Photobiol. 72, 467 471.
32. Li, A. S. C. F. Chignell (1991) The NoH value in EPR spin trapping: A new parameter for the identification of 5,5-dimethyl-1-pyrroline-N-oxide spin adducts. J. Biochem. Biophys. Methods 22, 83 87.
33. Ito, S. G. Prota (1977) A facile one-step synthesis of cysteinyldopas using mushroom tyrosinase. Experientia 33, 1118 1119.
34. Greco, G., K. Wakamatsu, L. Panzella, S. Ito, A. Napolitano M. d'Ischia (2009) Isomeric cysteinyldopas provide a (photo)degradable bulk component and a robust structural element in red human hair pheomelanin. Pigment Cell Melanoma Res. 22, 319 327.
35. Sealy, R. C., J. S. Hyde, C. C. Felix, I. A. Menon, G. Prota, H. M. Swartz, S. Persad H. F. Haberman (1982) Novel free radicals in synthetic and natural pheomelanins: Distinction between dopa melanins and cysteinyldopa melanins by ESR spectroscopy. Proc. Natl Acad. Sci. USA 79, 2885 2889.
36. Sealy, R. C., J. S. Hyde, C. C. Felix, I. A. Menon G. Prota (1982) Eumelanins and pheomelanins: Characterization by electron spin resonance spectroscopy. Science 217, 545 547.
37. Meredith, P. T. Sarna (2006) The physical and chemical properties of eumelanin. Pigment Cell Res. 19, 572 594.
38. Shima, T., T. Sarna, H. M. Swartz, A. Stroppolo, R. Gerbasi L. Zecca (1997) Binding of iron to neuromelanin of human substantia nigra and synthetic melanin: An EPR spectroscopy study. Free Radic. Biol. Med. 23, 110 119.
39. Pilas, B., T. Sarna, B. Kalyanaram H. M. Swartz (1988) The effect of melanin on iron associated decomposition of hydrogen peroxide. Free Radic. Biol. Med. 4, 285 293.
40. Hong, L. J. D. Simon (2006) Insight into the binding of divalent cations to Sepia eumelanin from IR absorption spectroscopy. Photochem. Photobiol. 82, 1265 1269.
41. Zecca, L., C. Bellei, P. Costi, A. Albertini, E. Monzani, L. Casella, M. Gallorini, L. Bergamaschi, A. Moscatelli, N. J. Turro, M. Eisner, P. R. Crippa, S. Ito, K. Wakamatsu, W. D. Bush, W. C. Ward, J. D. Simon F. A. Zucca (2008) New melanic pigments in the human brain that accumulate in aging and block environmental toxic metals. Proc. Natl Acad. Sci. USA 105, 17567 17572.
42. Sarna, T. (1992) Properties and function of the ocular melanin - A photobiophysical view. J. Photochem. Photobiol. B 12, 215 258.
43. Korytowski, W. T. Sarna (1990) Bleaching of melanin pigments. Role of copper ions and hydrogen peroxide in autooxidation and photooxidation of synthetic DOPA-melanin. J. Biol. Chem. 265, 12410 12416.
44. Tesema, Y. T., D. M. Pham K. J. Franz (2008) Counterions influence reactivity of metal ions with cysteinyldopa model compounds. Inorg. Chem. 47, 1087 1095.
45. Napolitano, A., S. Memoli, A. J. Nappi, M. d'Ischia G. Prota (1996) 5-S-Cysteinyldopa, a diffusible product of melanocyte activity, is an efficient inhibitor of hydroxylation/oxidation reactions induced by the Fenton system. Biochim. Biophys. Acta 1291, 75 82.
46. Di Donato, P., A. Napolitano G. Prota (2002) Metal ions as potential regulatory factors in the biosynthesis of red hair pigments: A new benzothiazole intermediate in the iron or copper assisted oxidation of 5-S-cysteinyldopa. Biochim. Biophys. Acta 1571, 157 166.
47. Palumbo, A., G. Nardi, M. d'Ischia, G. Misuraca G. Prota (1983) Nonenzymic oxidation of cysteinyldopa catalyzed by metallic ions. Gen. Pharmacol. 14, 253 257.