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The fundamental building blocks of red human hair pheomelanin are isoquinoline-containing dimers
Open accessAbstract
A TPCA-based, three-marker analysis has been used to demonstrate that the dimeric benzothiazolylthiazinoisoquinoline units recently identified in natural and synthetic pheomelanins are dominant structural building blocks of red human hair pheomelanin. This finding would prompt a revisit of pheomelanin build-up in terms of coupling of carboxylated benzothiazine intermediates into a specific BT-TIQ-related dimeric building block preceding further polymerization. Thus, BT-TIQ would reproduce all of the main chemical properties and spectral features of human pheomelanin. In this sense, BTTIQ compares to none of the low molecular weight intermediates so far isolated, including the trichochromes, and should, therefore, be duly considered in future models of pheomelanin structure.
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A main dimeric product of BTZCA, featuring isoquinoline and benzothiazole moieties (BT-TIQ), has been characterized as the most important building block of natural pigments from red hair and chicken feathers.
“A main dimeric product of BTZCA, featuring isoquinoline and benzothiazole moieties (BT-TIQ), has been characterized as the most important building block of natural pigments from red hair and chicken feathers (Figure 7) [47,48,49].”
From “Fifty Shades” of Black and Red or How Carboxyl Groups Fine Tune Eumelanin and Pheomelanin Properties (2016) · cites this paper as [48]
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Chemistry of Mixed Melanogenesis—Pivotal Roles of Dopaquinone†
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Self-citationThe “Benzothiazine” Chromophore of Pheomelanins: A Reassessment†
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Metadata
- Authors
- Greco, G., Panzella, L., Napolitano, A., & d’Ischia, M.
- Affiliations
- University of Naples Federico II (IT)
- Corresponding author
- Napolitano, Alessandra
- Venue
- Pigment Cell & Melanoma Research
- Publisher
- Wiley
- Published
- 2011-08-29
- Volume
- 25
- Issue
- 1
- Pages
- 110-112
- ISSN
- 1755-1471 (ISSN-L)
- 1755-148X
- OpenAlex
- W1575464816
- Cited by
- 15
- References
- 12
- Citations by year
- 2026: 1 · 2025: 1 · 2024: 1 · 2023: 2 · 2022: 1 · 2020: 1 · 2018: 1 · 2016: 1 · 2014: 2 · 2013: 2 · 2012: 2
- FWCI
- 0.92
- Type
- journal article
- Language
- en
- Open access
- bronze
- doi.org
- Locations
- Pigment Cell & Melanoma Research (publishedVersion)
- PubMed (publishedVersion)
- Scuola Normale Superiore di Pisa (submittedVersion)
- Funders
- Ministero dell’Istruzione, dell’Università e della Ricerca (PRIN 2008)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Cell Biology › melanin and skin pigmentation
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Biotechnology › Microbial Metabolism and Applications
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Melanoma and MAPK Pathways
- Keywords
- pheomelanin
- MeSH terms
- Chemical Fractionation, Hair, Humans, Melanins, Niacin, Tyrosine, Molecular Structure, Dimerization, Benzothiazoles
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