Relationship of melanin degradation products to actual melanin content: Application to human hair

Chad Borges, Jeanette C. Roberts, Diana G. Wilkins, Douglas E. Rollins

Research output: Contribution to journalArticle

58 Citations (Scopus)

Abstract

Methods not only for characterizing but also for quantitating melanin subtypes from the two types of melanin found in hair - eumelanin and pheomelanin - have been established. In relation to testing for drugs of abuse in hair, these methods will allow for correction of drug binding to specific melanin sub-types and will serve to improve drug measurement in hair. 5,6-Dihydroxyindole (DHI) and 5,6-dihydroxyindole-2-carboxylic acid (DHICA) make up the majority of the eumelanin polymer while benzothiazene units derived from 2-cysteinyl-S-Dopa (2-Cys-Dopa) and 5-cysteinyl-S-Dopa (5-CysDopa) compose the majority of the pheomelanin polymer. Our results show that: (1) pyrrole-2,3-dicarboxylic acid (PDCA) and pyrrole-2,3,5-tricarboxylic acid (PTCA), markers for DHI and DHICA units, respectively, are produced in 0.37 and 4.8% yields, respectively, when melanins are subjected to alkaline hydrogen peroxide degradation, (2) 3-aminotyrosine (3AT) and 4-amino-3-hydroxyphenylalanine (AHP), markers for 2-CysDopa and 5-CysDopa, respectively, are produced in 16 and 23% yield, respectively, when subjected to hydriodic acid hydrolysis, and (3) that black human hair contains approximately 99% eumelanin and 1% pheomelanin, brown and blond hair contain 95% eumelanin and 5% pheomelanin; and red hair contains 67% eumelanin and 33% pheomelanin. These data will allow deeper investigation into the relationship between melanin composition and drug incorporation into hair.

Original languageEnglish (US)
Pages (from-to)116-125
Number of pages10
JournalAnalytical Biochemistry
Volume290
Issue number1
DOIs
StatePublished - Mar 1 2001
Externally publishedYes

Fingerprint

Melanins
Hair
Dihydroxyphenylalanine
Degradation
Polymers
Pharmaceutical Preparations
Street Drugs
Carboxylic Acids
Hydrogen Peroxide
Hydrolysis
pheomelanin
eumelanin
Testing
Chemical analysis

ASJC Scopus subject areas

  • Biochemistry
  • Biophysics
  • Molecular Biology

Cite this

Relationship of melanin degradation products to actual melanin content : Application to human hair. / Borges, Chad; Roberts, Jeanette C.; Wilkins, Diana G.; Rollins, Douglas E.

In: Analytical Biochemistry, Vol. 290, No. 1, 01.03.2001, p. 116-125.

Research output: Contribution to journalArticle

Borges, Chad ; Roberts, Jeanette C. ; Wilkins, Diana G. ; Rollins, Douglas E. / Relationship of melanin degradation products to actual melanin content : Application to human hair. In: Analytical Biochemistry. 2001 ; Vol. 290, No. 1. pp. 116-125.
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abstract = "Methods not only for characterizing but also for quantitating melanin subtypes from the two types of melanin found in hair - eumelanin and pheomelanin - have been established. In relation to testing for drugs of abuse in hair, these methods will allow for correction of drug binding to specific melanin sub-types and will serve to improve drug measurement in hair. 5,6-Dihydroxyindole (DHI) and 5,6-dihydroxyindole-2-carboxylic acid (DHICA) make up the majority of the eumelanin polymer while benzothiazene units derived from 2-cysteinyl-S-Dopa (2-Cys-Dopa) and 5-cysteinyl-S-Dopa (5-CysDopa) compose the majority of the pheomelanin polymer. Our results show that: (1) pyrrole-2,3-dicarboxylic acid (PDCA) and pyrrole-2,3,5-tricarboxylic acid (PTCA), markers for DHI and DHICA units, respectively, are produced in 0.37 and 4.8{\%} yields, respectively, when melanins are subjected to alkaline hydrogen peroxide degradation, (2) 3-aminotyrosine (3AT) and 4-amino-3-hydroxyphenylalanine (AHP), markers for 2-CysDopa and 5-CysDopa, respectively, are produced in 16 and 23{\%} yield, respectively, when subjected to hydriodic acid hydrolysis, and (3) that black human hair contains approximately 99{\%} eumelanin and 1{\%} pheomelanin, brown and blond hair contain 95{\%} eumelanin and 5{\%} pheomelanin; and red hair contains 67{\%} eumelanin and 33{\%} pheomelanin. These data will allow deeper investigation into the relationship between melanin composition and drug incorporation into hair.",
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