ArticleInternational journal of molecular sciences2018
The Pro-Oxidant Activity of Pheomelanin is Significantly Enhanced by UVA Irradiation: Benzothiazole Moieties Are More Reactive than Benzothiazine Moieties.
Article in International journal of molecular sciences, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 36 papers.
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Who cites it
36 citing papers in PubMed, 44 citations in OpenAlex.
- Unique Features of Melanoma Risk and Diagnosis in Red-Haired Populations.International journal of molecular sciences · 2026Review
- Cutaneous Aging in Skin of Color: A Narrative Review.American journal of clinical dermatology · 2026Review
- 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
- Characterizing excited triplet states of synthetic eumelanin and pheomelanin by the application of selected diene probes.Scientific reports · 2026Article
- Dismantling darkness: interdisciplinary perspectives on melanin degradation.World journal of microbiology & biotechnology · 2026Review
- Unraveling UVA1-Induced Photomodifications of Eumelanin and Pheomelanin in Human Skin: Insights into Pigment Darkening.International journal of molecular sciences · 2026Article
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- Mechanistic Insights into Tyrosinase-Catalyzed Metabolism of Hydroquinone: Implications for the Etiology of Exogenous Ochronosis and Cytotoxicity to Melanocytes.International journal of molecular sciences · 2025Article
- Effect of Tigecycline on the Homeostasis of Human Epidermal Melanocytes and Fibroblasts.International journal of molecular sciences · 2025Article
- Screening and novel diagnostic technologies for melanoma: an update.Melanoma management · 2025Review
- Pharmacological effect and possible mechanism of Mudan Huaban recipe on melasma in mice induced by ultraviolet B and progesterone.Journal of traditional Chinese medicine = Chung i tsa chih ying wen pan · 2025Article
- Integrative analysis of DNA methylation and gene expression in skin cutaneous melanoma by bioinformatic approaches.Archives of dermatological research · 2025Article
- The metabolism of melanin synthesis-From melanocytes to melanoma.Pigment cell & melanoma research · 2024Review
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- MC1R and age heteroclassification of face phenotypes in the Rio Grande do Sul population.International journal of legal medicine · 2024Article
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- Photodynamic Therapy in Pigmented Basal Cell Carcinoma-A Review.Biomedicines · 2023Review
- Recent Advances in Characterization of Melanin Pigments in Biological Samples.International journal of molecular sciences · 2023Review
- A frame-shift mutation in COMTD1 is associated with impaired pheomelanin pigmentation in chicken.PLoS genetics · 2023Article
Corrections and comments
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Authors and funding
6 authors at 1 institution in 1 country.
Funding
Abstract
It is generally considered that eumelanin (EM) is photoprotective while pheomelanin (PM) is phototoxic. A recent study using a mouse model demonstrated that PM produces reactive oxygen species (ROS) that cause DNA damage and eventually lead to melanomagenesis. A biochemical study showed that PM possesses a pro-oxidant activity. PM consists of benzothiazine (BT) and benzothiazole (BZ) moieties, BT moieties being transformed to BZ moieties by heat or light. In this study, we compared the effects of ultraviolet A (UVA) irradiation using synthetic PMs with different BT to BZ ratios and using various coat color mouse hairs. We found that UVA irradiation of BZ-PM increased glutathione (GSH) depletion and generated more H₂O₂ than UVA irradiation of BT-PM. Non-irradiated controls did not exhibit strong pro-oxidant activities. Upon UVA irradiation, yellow mouse hairs oxidized GSH and produced H₂O₂ faster than black or albino mouse hairs. Next, to examine the mechanism of the pro-oxidant activity of BT-PM and BZ-PM, we examined the pro-oxidant activities of 7-(2-amino-2-carboxyethyl)-dihydro-1,4-benzothiazine-3-carboxylic acid (DHBTCA) and 6-(2-amino-2-carboxyethyl)-4-hydroxybenzothiazole (BZ-AA) as BT and BZ monomers, respectively. Their pro-oxidant activities were similar, but a large difference was seen in the effects of ROS scavengers, which suggests that the redox reactions may proceed via singlet oxygen in BZ-AA and via superoxide anions in DHBTCA. These results show that UVA enhances the pro-oxidant activity of PM, in particular BZ-PM.
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