ReviewInternational journal of molecular sciences2016
"Fifty Shades" of Black and Red or How Carboxyl Groups Fine Tune Eumelanin and Pheomelanin Properties.
Review in International journal of molecular sciences, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 48 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
48 citing papers in PubMed.
- From Monomers to Aggregates: The Influence of Redox State and Structure on the First Excited States of Eumelanin and Pheomelanin.International journal of molecular sciences · 2026Article
- From melanogenesis to melanin technologies.Communications chemistry · 2025Review
- Effect of Tigecycline on the Homeostasis of Human Epidermal Melanocytes and Fibroblasts.International journal of molecular sciences · 2025Article
- Inhibitory Effect of 505 nm Green Light Emitting Diode on Melanin Synthesis in Cellular Experiments and a Human Intervention Study.Acta dermato-venereologica · 2025Article
- Melanin in fungi: advances in structure, biosynthesis, regulation, and metabolic engineering.Microbial cell factories · 2024Review
- Melanin in the Retinal Epithelium and Magnetic Sensing: A Review of Current Studies.Biophysica · 2024Article
- A review of therapies for hyperpigmentation modulating the synthesis of eumelanin to pheomelanin.Archives of dermatological research · 2024Review
- The "Unconventional" Effect of Cysteine on theACS omega · 2024Article
- Photodynamic Therapy in Pigmented Basal Cell Carcinoma-A Review.Biomedicines · 2023Review
- Catecholamine Derivatives as Novel Crosslinkers for the Synthesis of Versatile Biopolymers.Journal of functional biomaterials · 2023Review
- The Multifaceted Opportunities Provided by the Pheomelanin-Inspired 1,4-Benzothiazine Chromophore: A Still-Undervalued Issue.Molecules (Basel, Switzerland) · 2023Review
- Article
- Human Skin Pigmentation: From a Biological Feature to a Social Determinant.Healthcare (Basel, Switzerland) · 2023Review
- Evaluation of phytochemicals of Poria cocos against tyrosinase protein: a virtual screening, pharmacoinformatics and molecular dynamics study.3 Biotech · 2023Article
- Chemiexcitation: Mammalian Photochemistry in the DarkPhotochemistry and photobiology · 2023Review
- Multiphoton FLIM Analyses of Native and UVA-Modified Synthetic Melanins.International journal of molecular sciences · 2023Article
- Recent Advances and Progress on Melanin: From Source to Application.International journal of molecular sciences · 2023Review
- A Model Eumelanin from 5,6-Dihydroxyindole-2-Carboxybutanamide Combining Remarkable Antioxidant and Photoprotective Properties with a Favourable Solubility Profile for Dermo-Cosmetic Applications.International journal of molecular sciences · 2023Article
- Structural Investigation of DHICA Eumelanin Using Density Functional Theory and Classical Molecular Dynamics Simulations.Molecules (Basel, Switzerland) · 2022Article
- 5,6-Dihydroxyindole eumelanin content in human skin with varying degrees of constitutive pigmentation.Pigment cell & melanoma research · 2022Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
6 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Recent advances in the chemistry of melanins have begun to disclose a number of important structure-property-function relationships of crucial relevance to the biological role of human pigments, including skin (photo) protection and UV-susceptibility. Even slight variations in the monomer composition of black eumelanins and red pheomelanins have been shown to determine significant differences in light absorption, antioxidant, paramagnetic and redox behavior, particle morphology, surface properties, metal chelation and resistance to photo-oxidative wear-and-tear. These variations are primarily governed by the extent of decarboxylation at critical branching points of the eumelanin and pheomelanin pathways, namely the rearrangement of dopachrome to 5,6-dihydroxyindole (DHI) and 5,6-dihydroxyindole-2-carboxylic acid (DHICA), and the rearrangement of 5-S-cysteinyldopa o-quinoneimine to 1,4-benzothiazine (BTZ) and its 3-carboxylic acid (BTZCA). In eumelanins, the DHICA-to-DHI ratio markedly affects the overall antioxidant and paramagnetic properties of the resulting pigments. In particular, a higher content in DHICA decreases visible light absorption and paramagnetic response relative to DHI-based melanins, but markedly enhances antioxidant properties. In pheomelanins, likewise, BTZCA-related units, prevalently formed in the presence of zinc ions, appear to confer pronounced visible and ultraviolet A (UVA) absorption features, accounting for light-dependent reactive oxygen species (ROS) production, whereas non-carboxylated benzothiazine intermediates seem to be more effective in inducing ROS production by redox cycling mechanisms in the dark. The possible biological and functional significance of carboxyl retention in the eumelanin and pheomelanin pathways is discussed.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.