ArticleInternational journal of molecular sciences2020
Nonenzymatic Spontaneous Oxidative Transformation of 5,6-Dihydroxyindole.
Article in International journal of molecular sciences, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed, 30 citations in OpenAlex.
- Melanin-Driven Delayed CPD Formation Is Independent of Melanin Biosynthesis Pathway.The Journal of investigative dermatology · 2026Article
- From melanogenesis to melanin technologies.Communications chemistry · 2025Review
- Stimulation of Skin Pigmentation with UVR Is a Risk Factor for Cholelithiasis.JID innovations : skin science from molecules to population health · 2025Review
- Visceral Peritoneum Hyperpigmentation in Chickens Is Associated withAnimals : an open access journal from MDPI · 2025Article
- The Pomegranate Flower Water Extract Negatively Regulates Melanogenesis by Suppressing MITF Expression and Its Target Enzymes.Journal of cosmetic dermatology · 2025Article
- Catecholamines Differ in Their Capacity to Form Melanin.microPublication biology · 2025Article
- Discovery of Indole-Thiourea Derivatives as Tyrosinase Inhibitors: Synthesis, Biological Evaluation, Kinetic Studies, and In Silico Analysis.International journal of molecular sciences · 2024Article
- Skin proteomic screening and functional analysis of differential proteins associated with coat color in sheep (Ovis aries).Animal bioscience · 2024Article
- Recent Advances in Characterization of Melanin Pigments in Biological Samples.International journal of molecular sciences · 2023Review
- Zebrafish in dermatology: a comprehensive review of their role in investigating abnormal skin pigmentation mechanisms.Frontiers in physiology · 2023Review
- Advances in Biomedical Functions of Natural Whitening Substances in the Treatment of Skin Pigmentation Diseases.Pharmaceutics · 2022Review
- Exciton interactions in helical crystals of a hydrogen-bonded eumelanin monomer.Chemical science · 2022Article
- Oxidative Transformations of 3,4-Dihydroxyphenylacetaldehyde Generate Potential Reactive Intermediates as Causative Agents for Its Neurotoxicity.International journal of molecular sciences · 2021Article
- Melanin, the What, the Why and the How: An Introductory Review for Materials Scientists Interested in Flexible and Versatile Polymers.Polymers · 2021Review
Corrections and comments
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Authors and funding
4 authors at 2 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Melanin is an important phenolic skin pigment found throughout the animal kingdom. Tyrosine and its hydroxylated product dopa provide the starting material for melanin biosynthesis in all animals. Through a set of well-established reactions, they are converted to 5,6-dihydroxyindole (DHI) and DHI-2-carboxylic acid (DHICA). Oxidative polymerization of these two indoles produces the brown to black eumelanin pigment. The steps associated with these transformations are complicated by the extreme instability of the starting materials and the transient and highly reactive nature of the intermediates. We have used mass spectral studies to explore the nonenzymatic mechanism of oxidative transformation of DHI in water. Our results indicate the facile production of not only dimeric and trimeric products but also higher oligomeric forms of DHI upon exposure to air in solution, even under nonenzymatic conditions. Such instantaneous polymerization of DHI avoids toxicity to self-matter and ensures the much-needed deposition of melanin at (a) the wound site and (b) the infection site in arthropods. The rapid deposition of DHI melanin is advantageous for arthropods given their open circulatory system; the process limits blood loss during wounding and prevents the spread of parasites by encapsulating them in melanin, limiting the damage.
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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.