Spectroscopy and photoreactivity of trichochromes: Molecular components of pheomelanins

Photochemistry and Photobiology

Volumn 82, Issue 1, 2006, Pages 318-323

  Simon, John D ^a   Goldsmith, Michael R ^a   Hong, Lian ^a   Kempf, Valerie R ^a   McGuckin, Laura E L ^a   Ye, Tong ^a   Zuber, Gerard ^a  

^a DUKE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COLORING AGENT; DNA; MELANIN; PHEOMELANIN; SUPEROXIDE;

CHEMICAL STRUCTURE; CHEMISTRY; CONFERENCE PAPER; ISOMERISM; SOLUTION AND SOLUBILITY; SPECTROPHOTOMETRY;

COLORING AGENTS; DNA; ISOMERISM; MELANINS; MODELS, MOLECULAR; SOLUTIONS; SPECTROPHOTOMETRY; SUPEROXIDES;

EID: 33644779029     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1562/2005-06-17-RA-578     Document Type: Conference Paper

References (19)

1. Chedekel, M. R., S. K. Smith, P. W. Post, A. Pokora and D. L. Vessell (1978) Photodestruction of pheomelanin - role of oxygen. Proc. Natl. Acad. Sci. USA 75, 5395-5399.
2. Vincensi, M. R., M. d'Ischia, A. Napolitano, E. M. Procaccini, G. Riccio, G. Monfrecola, P. Santoianni and G. Prota (1998) Phaeomelanin 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.
3. Prota, G., M. D. Ischia and A. Napolitano (1998) The chemistry of melanins and related metabolites. In The Pigmentary System (Edited by B. R. E. Nordlund, V. J. Hearing, R. A. King and J. P. Ortonne), pp. 307-332. Oxford University Press, New York.
4. Ito, S. (1998) Advances in chemical analysis of melanins. In The Pigmentary System. (Edited by B. R. E. Nordlund, V. J. Hearing, R. A. King and J. P. Ortonne), pp. 439-450. Oxford University Press, New York.
5. Prota, G. (1992) Melanins and Melanogenesis, pp. 134-152. Academic Press, San Diego.
6. Di Donato, P., A. Napolitano and G. Prota (2002) Metal ions as potential regulatory factors in the biosynthesis of red hair pigments: a new benzothazole intermediate in the iron or copper assisted oxidation of 5-S-cysteinyldopa. Biochem. Biophys. Acta 1571, 157-166.
7. Napolitano, A., P. Di Donata and 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 pigment of red hair. J. Org. Chem. 66, 6958-6966.
8. Ahlrichs, R., M. Bär, H.-P. Baron, R. Bauernschmitt, S. Böcker, M. Ehrig, K. Eichkorn, S. Elliott, F. Furche, F. Haase, M. Häser, H. Horn, C. Huber, U. Huniar, M. Kattannek, C. Kolmel, M. Kollwitz, K. May, C. Ochsenfeld, H. Öhm, A. Schäfer, U. Schneider, O. Treutler, M. von Arnim, F. Weigend, P. Weis and H. Weiss (2002) Turbomole (version 5.6). Universität Karlsruhe: Karlsruhe, Germany.
9. Becke, A. D. (1988) Density-functional exchange-energy approximation with correct asymptotic behavior. Phys. Rev. A 38, 3098-3100.
10. Perdew, J. P. (1986) Density-functional approximation for the correlation energy of the inhomogeneous electron gas. Phys. Rev. B 33, 8822-8824.
11. Schaefer, A., H. Horn and R. Ahlrichs (1992) Fully optimized contracted Gaussian basis sets for atoms lithium to krypton. J. Chem. Phys. 97, 2571.
12. Tong, Y., L. E. Lamb, K. Wakamatsu, S. Ito and J. D. Simon (2003) Ultrafast absorption and photothermal studies of decarboxy-trichochrome C in solution, invited paper for Symposium in-Print in Honor of Silvia E. Braslavsky: photothermal methods applied to photochemistry and photobiology. Photochem. Photobiol. Sci. 2, 821-823.
13. Tong, Y. and J. D. Simon (2003) The action spectrum for generation of the primary intermediate revealed by ultrafast absorption spectroscopy studies of pheomelanin. Photochem. Photobiol. 77, 72-76.
14. Roberts, J., B. Kukielczak, D. Hu, D. Miller. P. Bilski, R. Sik, A. Motten and C. Chignell (2002) The role of A2E in prevention or enhancement of light damage in human retinal pigment epithelial cells. Photochem. Photobiol. 75, 184-190.
15. Reszka, K., G. E. Eldred, R. H. Wang, C. Chignell and J. Dillon (1995) The photochemistry of human retinal lipofuscin as studied by EPR. Photochem. Photobiol. 62, 1005-1008.
16. Hermes-Lima, M., E. Nagy, P. Ponka and H. M. Schulman (1998) The Fe chelator pyridoxal isonicotinoyl hydrazone (PIH) protects plasmid pUC-18 DNA against OH-mediated strand breaks. Free Radic. Bio. Med. 25, 875-880.
17. 2,2-bi(2H-1,4-benzothiazine). Tetrahedron 30, 2781-2784.
18. 2,2-bi-(3-p-bromophenyl-2H-1,4-benzothiazine) . J. Chem. Soc. (C) 2610-2616.
19. Hong, L., Y. Liu and J. D. Simon (2004) Binding of metal ions to melanin and its effects on aerobic reactivity. Photochem. Photobiol. 80, 477-481.