ArticleAngewandte Chemie (International ed. in English)2021
Stability and Optical Absorption of a Comprehensive Virtual Library of Minimal Eumelanin Oligomer Models*.
Article in Angewandte Chemie (International ed. in English), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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10 citing papers in PubMed, 15 citations in OpenAlex.
- Bioreactor-based production of eumelanin nanoparticles by Streptomyces glaucescens NEAE-H: physicochemical characterization, anticancer and anti-inflammatory activities, and in silico analysis.Scientific reports · 2026Article
- Common Photoproperties of Eumelanin and Natural Organic Matter Emerge from Ensembles of Few-Layered Nanostructures.ACS central science · 2026Article
- From melanogenesis to melanin technologies.Communications chemistry · 2025Review
- Chemiexcitation in Ex Vivo Porcine Skin Model.Pigment cell & melanoma research · 2025Article
- Molecular engineering of melanin for enhanced biological γ-ray protection.Nature communications · 2025Article
- Insight into the Antioxidant Activity of 1,8-Dihydroxynaphthalene Allomelanin Nanoparticles.Antioxidants (Basel, Switzerland) · 2023Article
- Biomimetic pheomelanin to unravel the electronic, molecular and supramolecular structure of the natural product.Chemical science · 2023Article
- Fingerprint-based deep neural networks can model thermodynamic and optical properties of eumelanin DHI dimers.Chemical science · 2022Article
- Exciton interactions in helical crystals of a hydrogen-bonded eumelanin monomer.Chemical science · 2022Article
- Stability and Optical Absorption of a Comprehensive Virtual Library of Minimal Eumelanin Oligomer Models*.Angewandte Chemie (International ed. in English) · 2021Article
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Authors and funding
2 authors at 1 institution in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Eumelanin is responsible for photoprotection in living organisms. It is made of 5,6-dihydroxyindole (DHI) oligomers. However, lack of detailed structural knowledge limits understanding its function and exploiting its potential in material science. To uncover the relationship between structural stability and optical properties, we have studied a virtual library of 830 DHI dimers. We find a preference for oxidized, polycyclic structures which speaks in favor of graphite-like structures for the larger oligomers, and propose an electrocyclic formation mechanism. Besides widely considered quinone oxidation patterns, also structures with interfragment double bonds and zwitterionic resonance structures are stable. Future theoretical melanine models will have to cover this diversity, and we introduce a new representative set of 49 stable dimers. Some stable oxidized dimers have absorption energies as low as 1.3 eV. They may be present as substructures in the naturally found oligomers and contribute to the absorption spectrum of the biopolymer.
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