High-performance liquid chromatography estimation of cross-linking of dihydroxyindole moiety in eumelanin

Analytical Biochemistry

Volumn 434, Issue 2, 2013, Pages 221-225

  Ito, Shosuke ^a   Wakamatsu, Kazumasa ^a   Glass, Keely ^b   Simon, John D ^b,c  

^a FUJITA HEALTH UNIVERSITY   (Japan)

^b DUKE UNIVERSITY   (United States)

^c UNIVERSITY OF VIRGINIA   (United States)

Author keywords

Cross linking; Eumelanin; Fossil; HPLC; Pyrrole 2,3,4,5 tetracarboxylic acid; Pyrrole 2,3,5 tricarboxylic acid

Indexed keywords

AROMATIC COMPOUNDS; CARBOXYLATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OXIDATION; PEROXIDES;

EUMELANINS; FOSSIL; HPLC; HYDROGEN PEROXIDE OXIDATIONS; OXIDATION PRODUCTS; PYRROLE-2 ,3 ,5-TRICARBOXYLIC ACID; TRICARBOXYLIC ACIDS; ULTRAVIOLET DETECTION;

MELANIN;

5,6 DIHYDROXYINDOLE; 5,6 DIHYDROXYINDOLE 2 CARBOXYLIC ACID; DICARBOXYLIC ACID DERIVATIVE; EUMELANIN; HYDROGEN PEROXIDE; PYRROLE 2,3 DICARBOXYLIC ACID; PYRROLE 2,3,4 TRICARBOXYLIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CROSS LINKING; DECARBOXYLATION; FOSSIL; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OXIDATION; PRIORITY JOURNAL; ROOM TEMPERATURE; SYNTHESIS;

EID: 84872769231     PISSN: 00032697     EISSN: 10960309     Source Type: Journal    
DOI: 10.1016/j.ab.2012.12.005     Document Type: Article

References (26)

1. S. Ito, and K. Wakamatsu Chemistry of mixed melanogenesis: pivotal roles of dopaquinone Photochem. Photobiol. 84 2008 582 592
2. J.D. Simon, D. Peles, K. Wakamatsu, and S. Ito Current challenges in understanding melanogenesis: bridging chemistry, biological control, morphology, and function Pigm. Cell Melanoma Res. 22 2009 563 579
3. A. Palumbo, M. d'Ischia, M. Misuraca, L. De Martino, and G. Prota A new dopachrome rearranging enzyme from the ejected ink of the cuttlefish Sepia officinalis Biochem. J. 299 1994 839 844
4. S. Ito, and K. Fujita Microanalysis of eumelanin and pheomelanin in hair and melanomas by chemical degradation and liquid chromatography Anal. Biochem. 144 1985 527 536
5. A. Pezzella, M. d'Ischia, A. Napolitano, A. Palumbo, and G. Prota An integrated approach to the structure of Sepia melanin: evidence for a high proportion of degraded 5,6-dihydroxyindole-2-carboxylic acid units in the pigment backbone Tetrahedron 24 1997 8281 8286
6. S. Ito, Y. Nakanishi, R.K. Valenzuela, M.H. Brilliant, L. Kolbe, and 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 Pigm. Cell Melanoma Res. 24 2011 605 613
7. M. Piattelli, E. Fattorusso, S. Magno, and R.A. Nicolaus The structure of melanins and melanogenesis. II. Sepiomelanin and synthetic pigments Tetrahedron 18 1962 841 949
8. W.C. Ward, E.C. Lamb, D. Gooden, X. Chen, D.J. Burinsky, and J.D. Simon Quantification of naturally occurring pyrrole acids in melanosomes Photochem. Photobiol. 84 2008 700 705
9. K. Glass, S. Ito, P.R. Wilby, T. Sota, A. Nakamura, C.R. Bowers, J. Vinther, S. Dutta, R. Summons, D.E.G. Briggs, K. Wakamatsu, and J.D. Simon Direct chemical evidence for eumelanin pigment from the Jurassic period Proc. Natl. Acad. Sci. USA 109 2012 10213 10218
10. S. Ito, and K. Wakamatsu Chemical degradation of melanins: application to identification of dopamine-melanin Pigm. Cell Res. 11 1998 120 126
11. H. Ozeki, K. Wakamatsu, S. Ito, and I. Ishiguro Chemical characterization of eumelanins with special emphasis on 5,6-dihydroxyindole-2-carboxylic acid content and molecular size Anal. Biochem. 248 1997 149 157
12. S. Kamijo, C. Kanazawa, and Y. Yamamoto Copper- or phosphine-catalyzed reaction of alkynes with isocyanides: regioselective synthesis of substituted pyrroles controlled by the catalyst J. Am. Chem. Soc. 127 2005 9260 9266
13. C.R. Borgers, J.C. Roberts, D.G. Wilkins, and D.E. Rollins Relationship of melanin degradation products to actual melanin content: application to human hair Anal. Biochem. 290 2001 116 125
14. L. Panzella, P. Manini, G. Monfrecola, M. d'Ischia, and A. Napolitano An easy-to-run method for routine analysis of eumelanin and pheomelanin in pigmented tissues Pigm. Cell Res. 20 2007 128 133
15. K. Wakamatsu, Y. Nakanishi, N. Miyazaki, L. Kolbe, and S. Ito UVA-induced degradation of melanins: fission of indole moiety in eumelanin and conversion to benzothiazole moiety in pheomelanin Pigm. Cell Melanoma Res. 25 2012 434 445
16. K. Wakamatsu, K. Ohtara, and S. Ito Chemical analysis of late stages of pheomelanogenesis: conversion of dihydrobenzothiazine to a benzothiazole structure Pigm. Cell Melanoma Res. 22 2009 474 486
17. M. Randhawa, T. Huff, J.C. Valencia, Z. Younossi, V. Chandhoke, V.J. Hearing, and A. Baranova Evidence for ectopic synthesis of melanin in human adipose tissue FASEB J. 23 2009 835 843
18. E. Dadachova, R.A. Bryan, R.C. Howell, A.D. Schweitzer, P. Aisen, J.D. Nosanchuk, and A. Casadevall The radioprotective properties of fungal melanin are a function of its chemical composition, stable radical presence, and spatial arrangement Pigm. Cell Melanoma Res. 21 2008 192 199
19. S. Ito, and K. Wakamatsu Quantitative analysis of eumelanin and pheomelanin in humans, mice, and other animals: a comparative review Pigm. Cell Res. 16 2003 523 531
20. H. Okuda, K. Wakamatsu, S. Ito, and T. Sota Possible oxidative polymerization mechanism of 5,6-dihydroxyindole from ab initio calculations J. Phys. Chem. A 112 2008 11213 11222
21. A. Pezzella, L. Panzella, A. Natangelo, M. Arzillo, A. Napolitano, and M. d'Ischia 5,6-Dihydroxyindole tetramers with "anomalous" interunit bonding patterns by oxidative coupling of 5,5′,6,6′-tetrahydroxy-2, 7′-biindolyl: emerging complexities on the way toward an improved model of eumelanin buildup J. Org. Chem. 72 2007 9225 9230
22. G. Greco, K. Wakamatsu, L. Panzella, S. Ito, A. Napolitano, and M. d'Ischia Isomeric cysteinyldopas provide a (photo)degradative bulk component and a robust structural element in red human hair pheomelanin Pigm. Cell Melanoma Res. 22 2009 319 327
23. L. Zecca, R. Fariellob, P. Riedererc, D. Sulzerd, A. Gattia, and D. Tampellinia The absolute concentration of nigral neuromelanin, assayed by a new sensitive method, increases throughout the life and is dramatically decreased in Parkinson's disease FEBS Lett. 510 2002 216 220
24. O. Strauss The retinal pigment epithelium in visual function Physiol. Rev. 85 2005 845 881
25. H. Hayashi, M. Sone, P.A. Schachern, K. Wakamatsu, M.M. Paparella, and T. Nakashima Comparison of the quantity of cochlear melanin in young and old C57BL/6 mice Arch. Otolaryngol. Head Neck Surg. 133 2007 151 154
26. T. Sarna, J.M. Burke, W. Korytowski, M. Rozanowska, C.M.B. Shumatz, A. Zareba, and M. Zareba Loss of melanin from human RPE with aging: possible role of melanin photooxidation Exp. Eye Res. 76 2003 89 98