References
49
5. D. Kovacs, E. Flori, V. Maresca, M. Ottaviani, N. Aspite, M.L. Dell’Anna, L. Panzella, A.
Napolitano, M. Picardo, M. d’Ischia, The eumelanin intermediate 5,6-dihydroxyindole-2carboxylic acid is a messenger in the cross-talk among epidermal cells. J. Invest. Dermatol.
132, 1196–1205 (2012)
6. P. Muneta, Enzymatic blackening in potatoes influence of pH on dopachrome oxidation. Am.
Potato J. 54, 387–393 (1977)
7. S. Ito, N. Suzuki, S. Takebayashi, S. Commo, K. Wakamatsu, Neutral pH and copper ions
promote eumelanogenesis after the dopachrome stage. Pigment Cell Melanoma Res. 26, 817–
825 (2013)
8. H.S. Mason, The chemistry of melanin. III. mechanism of the oxidation of dihydroxyphenylalanine by tyrosinase. J. Biol. Chem. 172, 83–99 (1948)
9. K. Wakamatsu, S. Ito, Preparation of eumelanin-related metabolites 5,6-dihydroxyindole 5,6dihydroxyindole-2-carboxylic acid and their O-methyl derivatives. Anal. Biochem. 170, 335–
340 (1988)
10. A. Palumbo, M. d’Ischia, G. Misuraca, G. Prota, Effect of metal ions on the rearrangement of
dopachrome. Biochim. Biophys. Acta 925, 203–209 (1987)
11. A. Biesemeier, U. Schraermeyer, O. Eibl, Chemical composition of melanosomes lipofuscin
and melanolipofuscin granules of human RPE tissues. Exp. Eye Res. 93, 29–39 (2011)
12. Y. Liu, L. Hong, K. Wakamatsu, S. Ito, B. Adhyaru, C.Y. Cheng, C.R. Bowers, J.D. Simon,
Comparison of structural and chemical properties of black and red human hair melanosomes.
Photochem. Photobiol. 81, 135–144 (2005)
13. A. Palumbo, F. Solano, G. Misuraca, P. Aroca, J.C. García-Borrón, J.A. Lozano, G. Prota,
Comparative action of dopachrome tautomerase and metal ions on the rearrangement of
dopachrome. Biophys. Acta 1115, 1–5 (1991)
14. S. Commo, O. Gaillard, S. Thibaut, B.A. Bernard, Absence of TRP-2 in melanogenic
melanocytes of human hair. Pigment Cell Res. 17, 488–497 (2004)
15. S. Commo, K. Wakamatsu, I. Lozano, S. Panhard, G. Loussouarn, B.A. Bernard, S. Ito, Agedependent changes in eumelanin composition in hairs of various ethnic origins. Int. J. Cosmet.
Sci. 34, 102–107 (2012)
16. S. Ito, Y. Nakanishi, R.K. Valenzuela, M.H. Brilliant, L. Kolbe, K. Wakamatsu, Usefulness of
alkaline hydrogen peroxide oxidation to analyze eumelanin and pheomelanin in various tissue
samples: application to chemical analysis of human hair melanins. Pigment Cell Melanoma
Res. 24, 605–613 (2011)
17. F. Solano, C. Jiménez-Cervantes, J.H. Martínez-Liarte, J.C. García-Borrón, J.R. Jara, J.A.
Lozano, Molecular mechanism for catalysis by a new zinc-enzyme dopachrome tautomerase.
Biochem. J. 313, 447–453 (1996)
18. C.J. Vavricka, B.M. Christensen, J. Li, Melanization in living organisms: a perspective of
species evolution. Protein Cell 1, 830–841 (2010)
19. M. Sugumaran, H. Dali, V. Semensi, Formation of a stable quinone methide during tyrosinasecatalyzed oxidation of α-methyl dopa methyl ester and its implication in melanin biosynthesis.
Bioorg. Chem. 18, 144–153 (1990)
20. M. Sugumaran, V. Semensi, Quinone methide as a new intermediate in eumelanin biosynthesis.
J. Biol. Chem. 266, 6073–6078 (1991)
21. R. Kishida, Y. Ushijima, A.G. Saputro, H. Kasai, Effect of pH on elementary steps of
dopachrome conversion from first-principles calculation. Pigment Cell Melanoma Res. 27,
734–743 (2014)
22. R. Kishida, A.G. Saputro, H. Kasai, Mechanism of dopachrome tautomerization into 5,6dihydroxyindole-2-carboxylic acid catalyzed by Cu(II) based on quantum chemical calculations. Biochim. Biophys. Acta 2015, 281–286 (1850)
23. P. Hohenberg, W. Kohn, Inhomogeneous electron gas. Phys. Rev. 136, B864–B871 (1964)
24. W. Kohn, L.J. Sham, Self-consistent equations including exchange and correlation effects.
Phys. Rev. 140, A1133–A1138 (1965)
49
5. D. Kovacs, E. Flori, V. Maresca, M. Ottaviani, N. Aspite, M.L. Dell’Anna, L. Panzella, A.
Napolitano, M. Picardo, M. d’Ischia, The eumelanin intermediate 5,6-dihydroxyindole-2carboxylic acid is a messenger in the cross-talk among epidermal cells. J. Invest. Dermatol.
132, 1196–1205 (2012)
6. P. Muneta, Enzymatic blackening in potatoes influence of pH on dopachrome oxidation. Am.
Potato J. 54, 387–393 (1977)
7. S. Ito, N. Suzuki, S. Takebayashi, S. Commo, K. Wakamatsu, Neutral pH and copper ions
promote eumelanogenesis after the dopachrome stage. Pigment Cell Melanoma Res. 26, 817–
825 (2013)
8. H.S. Mason, The chemistry of melanin. III. mechanism of the oxidation of dihydroxyphenylalanine by tyrosinase. J. Biol. Chem. 172, 83–99 (1948)
9. K. Wakamatsu, S. Ito, Preparation of eumelanin-related metabolites 5,6-dihydroxyindole 5,6dihydroxyindole-2-carboxylic acid and their O-methyl derivatives. Anal. Biochem. 170, 335–
340 (1988)
10. A. Palumbo, M. d’Ischia, G. Misuraca, G. Prota, Effect of metal ions on the rearrangement of
dopachrome. Biochim. Biophys. Acta 925, 203–209 (1987)
11. A. Biesemeier, U. Schraermeyer, O. Eibl, Chemical composition of melanosomes lipofuscin
and melanolipofuscin granules of human RPE tissues. Exp. Eye Res. 93, 29–39 (2011)
12. Y. Liu, L. Hong, K. Wakamatsu, S. Ito, B. Adhyaru, C.Y. Cheng, C.R. Bowers, J.D. Simon,
Comparison of structural and chemical properties of black and red human hair melanosomes.
Photochem. Photobiol. 81, 135–144 (2005)
13. A. Palumbo, F. Solano, G. Misuraca, P. Aroca, J.C. García-Borrón, J.A. Lozano, G. Prota,
Comparative action of dopachrome tautomerase and metal ions on the rearrangement of
dopachrome. Biophys. Acta 1115, 1–5 (1991)
14. S. Commo, O. Gaillard, S. Thibaut, B.A. Bernard, Absence of TRP-2 in melanogenic
melanocytes of human hair. Pigment Cell Res. 17, 488–497 (2004)
15. S. Commo, K. Wakamatsu, I. Lozano, S. Panhard, G. Loussouarn, B.A. Bernard, S. Ito, Agedependent changes in eumelanin composition in hairs of various ethnic origins. Int. J. Cosmet.
Sci. 34, 102–107 (2012)
16. S. Ito, Y. Nakanishi, R.K. Valenzuela, M.H. Brilliant, L. Kolbe, K. Wakamatsu, Usefulness of
alkaline hydrogen peroxide oxidation to analyze eumelanin and pheomelanin in various tissue
samples: application to chemical analysis of human hair melanins. Pigment Cell Melanoma
Res. 24, 605–613 (2011)
17. F. Solano, C. Jiménez-Cervantes, J.H. Martínez-Liarte, J.C. García-Borrón, J.R. Jara, J.A.
Lozano, Molecular mechanism for catalysis by a new zinc-enzyme dopachrome tautomerase.
Biochem. J. 313, 447–453 (1996)
18. C.J. Vavricka, B.M. Christensen, J. Li, Melanization in living organisms: a perspective of
species evolution. Protein Cell 1, 830–841 (2010)
19. M. Sugumaran, H. Dali, V. Semensi, Formation of a stable quinone methide during tyrosinasecatalyzed oxidation of α-methyl dopa methyl ester and its implication in melanin biosynthesis.
Bioorg. Chem. 18, 144–153 (1990)
20. M. Sugumaran, V. Semensi, Quinone methide as a new intermediate in eumelanin biosynthesis.
J. Biol. Chem. 266, 6073–6078 (1991)
21. R. Kishida, Y. Ushijima, A.G. Saputro, H. Kasai, Effect of pH on elementary steps of
dopachrome conversion from first-principles calculation. Pigment Cell Melanoma Res. 27,
734–743 (2014)
22. R. Kishida, A.G. Saputro, H. Kasai, Mechanism of dopachrome tautomerization into 5,6dihydroxyindole-2-carboxylic acid catalyzed by Cu(II) based on quantum chemical calculations. Biochim. Biophys. Acta 2015, 281–286 (1850)
23. P. Hohenberg, W. Kohn, Inhomogeneous electron gas. Phys. Rev. 136, B864–B871 (1964)
24. W. Kohn, L.J. Sham, Self-consistent equations including exchange and correlation effects.
Phys. Rev. 140, A1133–A1138 (1965)