Comparison of structural and chemical properties of black and red human hair melanosomes

Photochemistry and Photobiology

Volumn 81, Issue 1, 2005, Pages 135-144

  Liu, Yan ^a   Hong, Lian ^a   Wakamatsu, Kazumasa ^b   Ito, Shosuke ^b   Adhyaru, Bhavin ^c   Cheng, Chi Yuan ^c   Bowers, Clifford R ^c   Simon, John D ^a  

^a DUKE UNIVERSITY   (United States)

^b FUJITA HEALTH UNIVERSITY   (Japan)

^c University of Florida ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINOHYDROXYPHENOLANALINE; 5,6 DIHYDROXYINDOLE; 5,6 DIHYDROXYINDOLE 2 CARBOXYLIC ACID; AMINO ACID; CARBOXYLIC ACID DERIVATIVE; COPPER; EUMELANIN; FERRIC ION; HEAVY METAL; INDOLE DERIVATIVE; KERATIN; MELANIN; PERMANGANATE POTASSIUM; PHEOMELANIN; PIGMENT; PYRROLE 2,3,5 TRICARBOXYLIC ACID; PYRROLE DERIVATIVE; TOLUENE; UNCLASSIFIED DRUG; ZINC;

ADULT; AMINO ACID ANALYSIS; ARTICLE; ATOMIC FORCE MICROSCOPY; CARBON NUCLEAR MAGNETIC RESONANCE; CELL SHAPE; CELL STRUCTURE; CEPHALOPOD; CHEMICAL ANALYSIS; CHEMICAL COMPOSITION; CONTROLLED STUDY; DEGRADATION; FEMALE; HAIR COLOR; HUMAN; HUMAN CELL; HUMAN TISSUE; HYDROLYSIS; INFRARED SPECTROSCOPY; MELANOSOME; SEPIA;

ADULT; AMINO ACIDS; FEMALE; HAIR; HAIR COLOR; HUMANS; MELANOSOMES; MICROSCOPY, ATOMIC FORCE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; SPECTROPHOTOMETRY, INFRARED;

EID: 14744281656     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1562/2004-08-03-RA-259.1     Document Type: Article

References (59)

1. Prota, G., M. D. Ischia and A. Napolitano (1998) The chemistry of melanins and related metabolites. In The Pigmentary System (Edited by R. E. Boissy, J. J. Nordlund, V. J. Hearing, R. A. King and J. P. Ortonne), pp. 307-332. Oxford Unviersity Press, New York.
2. Ito, S. (1998) Advances in chemical analysis of melanins. In The Pigmentary System (Edited by R. E. Boissy, J. J. Nordlund, V. J. Hearing, R. A. King and J. P. Ortonne), pp. 439-450. Oxford University Press, New York.
3. Piley, P. A. (1998) Mechanism of inhibition of melanin pigmentation. In The Pigmentary System (Edited by R. E. Boissy, J. J. Nordlund, V. J. Hearing, R. A. King and J. P. Ortonne), pp. 401-422. Oxford University Press, New York.
4. Wakamatsu, K. and S. Ito (2002) Advanced chemical methods in melanin determination. Pigm. Cell Res. 15, 174-183.
5. Ozeki, H., S. Ito and K. Wakamatsu (1996) Chemical characterization of melanins in sheep wool and human hair. Pigm. Cell Res. 9, 51-57.
6. Liu, Y., V. R. Kempf, J. B. Nofsinger, E. E. Weinert, M. Rudnicki, K. Wakamatsu, S. Ito and J. D. Simon (2003) Comparison of the structural and physical properties of human hair eumelanin following enzymatic or acid/base extraction. Pigm. Cell Res. 16, 355-365.
7. Ahene, A. B., S. Saxena and S. Nacht (1994) Photoprotection of solubilized and microdispersed melanin particles. J. Investig. Dermatol. 102, 268.
8. Zeise, L., M. R. Chedekel and T. B. Fitzpatrick (1995) Melanin: Its Role in Human Photoprotection. Valdenmar Publishing Company, Overland Park, KS.
9. Giacomoni, P. U. (1995) Open questions in photobiology. 3. Melanin and photoprotection. J. Photochem. Photobiol. B: Biol. 29, 87-89.
10. Kollias, N., R. M. Sayre, L. Zeise and M. R. Chedekel (1991) Photoprotection by melanin. J. Photochem. Photobiol. B: Biol. 9, 135-160.
11. Kobayashi, N., T. Muramatsu, Y. Yamashina, T. Shirai, T. Ohnishi and T. Mori (1993) Melanin reduces ultraviolet-induced DNA-damage formation and killing rate in cultured human-melanoma cells. J. Investig. Dermatol. 101, 685-689.
12. Riley, P. A. (1997) Melanin. Int. J. Biochem. Cell Biol. 29, 1235-1239.
13. Hill, H. Z. (1994) Is melanin photoprotective or is it photosensitizing. J. Investig. Dermatol. 102, 265.
14. Hill, H. Z., W. Li, P. Xin and D. L. Mitchell (1997) Melanin: a two edged sword? Pigm. Cell Res. 10, 158-161.
15. 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.
16. 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.
17. Wenczl, E., G. P. Van der Schans, L. Roza, R. M. Kolb, A. J. Timmerman, N. P. M. Smit, S. Pavel and A. A. Schothorst (1998) (Pheo)melanin photosensitizes UVA-induced DNA damage in cultured human melanocytes. J. Investig. Dermatol. 111, 678-682.
18. Rozanowska, M., T. Sarna, E. J. Land and T. G. Truscott (1999) Free radical scavenging properties of melanin interaction of eu- and pheomelanin models with reducing and oxidising radicals. Free Radic. Biol. Med. 26, 518-525.
19. Chedekel, M. R., P. P. Agin and R. M. Sayre (1980) Photochemistry of pheomelanin-action spectrum for superoxide production. Photochem. Photobiol. 31, 553-555.
20. Sarna, T. and R. C. Sealy (1984) Free-radicals from eumelanins-quantum yields and wavelength dependence. Arch. Biochem. Biophys. 232, 574-578.
21. Sarna, T., I. A. Menon and R. C. Sealy (1984) Photoinduced oxygen-consumption in melanin systems .2. Action spectra and quantum yields for pheomelanins. Photochem. Photobiol. 39, 805-809.
22. Sarna, T. and R. C. Sealy (1984) Photoinduced oxygen-consumption in melanin systems-action spectra and quantum yields for eumelanin and synthetic melanin. Photochem. Photobiol. 39, 69-74.
23. Sarna, T., I. A. Menon and R. C. Sealy (1985) Photosensitization of melanins-a comparative-study. Photochem. Photobiol. 42, 529-532.
24. Ezzahir, A. (1989) The influence of melanins on the photoperoxidation of lipids. J. Photochem. Photobiol. B: Biol. 3, 341-349.
25. Schmitz, S., P. D. Thomas, T. M. Allen, M. J. Poznansky and K. Jimbow (1995) Dual role of melanins and melanin precursors as photoprotective and phototoxic agents-inhibition of ultraviolet radiation-induced lipid-peroxidation. Photochem. Photobiol. 61, 650-655.
26. Krol, E. S. and D. C. Liebler (1998) Photoprotective actions of natural and synthetic melanins. Chem. Res. Toxicol. 11, 1434-1440.
27. Liu, Y. and J. D. Simon (2003) Isolation and biophysical studies of natural eumelanins: applications of imaging technologies and ultrafast spectroscopy. Pigm. Cell Res. 16, 606-618.
28. Sarna, T. (1992) Properties and function of the ocular melanin-a photobiophysical view. J. Photochem. Photobiol. B: Biol. 12, 215-258.
29. Bustamante, J., L. Bredeston, G. Malanga and J. Mordoh (1993) Role of melanin as a scavenger of active oxygen species. Pigm. Cell Res. 6, 348-353.
30. Liu, Y., L. Hong, V. R. Kempf, K. Wakamatsu, S. Ito and J. D. Simon (2004) Ion exchange and adsorption of Fe(III) by Sepia melanin. Pigm. Cell Res. 17, 262-269.
31. Palumbo, A., F. Solano, G. Misuraca, P. Aroca, J. C. G. Borron, J. A. Lozano and G. Prota (1991) Comparative action of dopachrome tautomerase and metal-ions on the rearrangement of dopachrome. Biochim. Biophys. Acta 1115, 1-5.
32. Pawelek, J. M. (1991) After dopachrome. Pigm. Cell Res. 4, 53-62.
33. Shibata, T., G. Prota and Y. Mishima (1993) Non-melanosomal regulatory factors in melanogenesis. J. Investig. Dermatol. 100, S274-S280.
34. Di Donato, P., A. Napolitano and 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-Gen. Subj. 1571, 157-166.
35. Ito, S. and K. Wakamatsu (1994) An improved modification of permanganate oxidation of eumelanin that gives a constant yield of pyrrole-2,3,5- tricarboxylic acid. Pigm. Cell Res. 7, 141-144.
36. Ito, S. and K. Fujita (1985) Microanalysis of eumelanin and pheomelanin in hair and melanomas by chemical degradation and liquid-chromatography. Anal. Biochem. 144, 527-536.
37. Ito, S. and K. Wakamatsu (1998) Chemical degradation of melanins: application to identification of dopamine-melanin. Pigm. Cell Res. 11, 120-126.
38. Ozeki, H., S. Ito, K. Wakamatsu and A. J. Thody (1996) Spectrophotometric characterization of eumelanin and pheomelanin in hair. Pigm. Cell Res. 9, 265-270.
39. Clancy, C. M. R. and J. D. Simon (2001) Ultrastructural organization of eumelanin from Sepia officinalis measured by atomic force microscopy. Biochemistry 40, 13353-13360.
40. Reinheimer, P., J. Hirschinger, P. Granger, P. Breton, A. Lagrange, P. Guard, M. A. Lefebvre and N. Goetz (1999) Cross-polarization/magic-angle- spinning nuclear magnetic resonance in selectively C-13-labeled synthetic eumelanins. Biochim. Biophys. Acta-Gen. Subj. 1472, 240-249.
41. Adhyaru, B. B., N. G. Akhmedov, A. R. Katritzky and C. R. Bowers (2003) Solid-state cross-polarization magic angle spinning C-13 and N-15 NMR characterization of Sepia melanin, Sepia melanin free acid and human hair melanin in comparison with several model compounds. Magn. Reson. Chem. 41, 466-474.
42. Birbeck, M. S. C. (1963) Electron microscopy of melanocytes: the fine structure of hair-bulb premelanosomes. Ann. N. Y. Acad. Sci. 100, 540-547.
43. Jimbow, K., O. Ishida, S. Ito, Y. Hori, C. J. Witkop and R. A. King (1983) Combined chemical and electron-microscopic studies of pheomelanosomes in human red hair. J. Investig. Dermatol. 81, 506-511.
44. Novellino, L., A. Napolitano and G. Prota (2000) Isolation and characterization of mammalian eumelanins from hair and irides. Biochim. Biophys. Acta-Gen. Subj. 1475, 295-306.
45. Basrur, V., F. Yang, T. Kushimoto, Y. Higashimoto, K. Yasumoto, J. Valencia, J. Muller, W. D. Vieira, H. Watabe, J. Shabanowitz, V. J. Hearing, D. F. Hunt and E. Appella (2003) Proteomic analysis of early melanosomes: identification of novel melanosomal proteins. J. Proteome Res. 2, 69-79.
46. McGraw, K. J. (2003) Melanins, metals, and mate quality. Oikos 102, 402-406.
47. Liu, Y. and J. D. Simon (2005) Metal ion interactions and the structural organization of Sepia eumelanin. Pigm. Cell Res. 18, 42-48.
48. Samokhvalov, A., Y. Liu and J. D. Simon (2004) Characterization of the iron-binding site in Sepia eumelanin by resonance raman spectroscopy. Photochem. Photobiol. 80, 84-88.
49. Aime, S., B. Bergamasco, M. Casu, G. Digilio, M. Fasano, S. Giraudo and L. Lopiano (2000) Isolation and C-13-NMR characterization of an insoluble proteinaceous fraction from substantia nigra of patients with Parkinson's disease. Mov. Disord. 15, 977-981.
50. Knicker, H., G. Almendros, F. J. Gonzalez Vila, H. D. Ludemann and F. Martin (1995) C-13 and N-15 NMR analysis of some fungal melanins in comparison with soil organic matter. Org. Geochem. 23, 1023-1028.
51. Kramer, K. J., T. L. Hopkins and J. Schaefer (1995) Applications of solids NMR to the analysis of insect sclerotized structures. Insect Biochem. Mol. Biol. 25, 1067-1080.
52. Bridelli, M. G., D. Tampellini and L. Zecca (1999) The structure of neuromelanin and its iron binding site studied by infrared spectroscopy. FEBS Lett. 457, 18-22.
53. Double, K. L., L. Zecca, P. Costi, M. Mauer, C. Griesinger, S. Ito, D. Ben-Shachar, G. Bringmann, R. G. Fariello, P. Riederer and M. Gerlach (2000) Structural characteristics of human substantia nigra neuromelanin and synthetic dopamine melanins. J. Neurochem. 75, 2583-2589.
54. 2+ ions. Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 57, 2525-2533.
55. Bridelli, M. G., R. Capelletti and P. R. Crippa (1980) Infrared spectroscopy of eye and synthetic melanins at various values of pH and hydration. Physiol. Chem. Phys. 12, 233-240.
56. Bilinska, B. (1996) Progress of infrared investigations of melanin structures. Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 52, 1157-1162.
57. Pierce, J. A. and D. M. Rast (1995) A comparison of native and synthetic mushroom melanins by fourier-transform infrared-spectroscopy. Phytochemistry 39, 49-55.
58. Palumbo, A. (2003) Melanogenesis in the ink gland of Sepia officinalis. Pigm. Cell Res. 16, 517-522.
59. Ozeki, H., K. Wakamatsu, S. Ito and I. Ishiguro (1997) Chemical characterization of eumelanins with special emphasis on 5,6-dihydroxyindole-2- carboxylic acid content and molecular size. Anal. Biochem. 248, 149-157.