Thiol-induced hydroxyl radical formation and scavenger effect of thiocarbamides on hydroxyl radicals
Abstract
The effects of thiols and thiocarbamides on hydroxyl radical (.OH) formation by the hypoxanthine(HYP)-xanthine oxidase(XOD)-Fe3+ .EDTA system were investigated in the range of 0.5-5 mM by colorimetrically measuring salicylate hydroxylation. Thiocarbamides powerfully inhibited the hydroxylation while thiols showed a paradoxical effect, enhancing it at low concentrations, but inhibiting it at high ones. Thiols in the presence of Fe3+ .EDTA generated superoxide anions (O2-.) and .OH during the oxidation, but thiocarbamides did not. A study of the effect of ergothioneine, a thiocarbamide present in mammals, on the .OH spin adduct of 5,5-dimethyl-1-pyrroline-N-oxide(DMPO) by EPR spectrometry showed that it effectively decreased the .OH spin adduct without causing the appearance of other signals. Reaction mechanisms are proposed for the O2-. evolution and .OH formation by the thiols themselves in the presence of Fe3+ .EDTA and .OH with thiols and thiocarbamides.
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ERG can react with and detoxify, or prevent the formation of, hydroxyl radicals, singlet oxygen, ozone, superoxide, peroxide, hypochlorite and peroxynitrite.
“Although the literature is somewhat scattered and heterogeneous, it seems clear that as well as hydroxyl radicals(228–232), ERG can also react with and detoxify, or prevent the formation of, singlet oxygen(233–242), ozone(243), superoxide(231,241,244–246), peroxide(32,124,247,248), hypochlorite(32,232,249) and peroxynitrite(224,231,250,251).”
From The biology of ergothioneine, an antioxidant nutraceutical (2020) · cites this paper as [230]
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- Authors
- Motohashi, N., & Mori, I.
- Affiliations
- Kobe Women's University (JP)
- Venue
- Journal of Inorganic Biochemistry
- Publisher
- Elsevier BV
- Published
- 1986-03
- Volume
- 26
- Issue
- 3
- Pages
- 205-212
- ISSN
- 0162-0134 (ISSN-L)
- OpenAlex
- W2040455583
- Cited by
- 53
- References
- 15
- Citations by year
- 2026: 2 · 2025: 2 · 2024: 4 · 2023: 2 · 2022: 2 · 2021: 5 · 2020: 3 · 2019: 1 · 2018: 1 · 2017: 1 · 2014: 1 · 2012: 2
- FWCI
- 1.12
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of Inorganic Biochemistry (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Free Radicals and Antioxidants
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Redox biology and oxidative stress
- Health Sciences › Medicine › Biochemistry › Antioxidant Activity and Oxidative Stress
- Keywords
- hydroxyl radical generation, thiols, thiourea, ergothioneine, superoxide, xanthine oxidase, hypoxanthine, salicylate hydroxylation, free radical scavenging, DMPO spin adducts, electron spin resonance, reaction mechanism
- MeSH terms
- Chemistry, Physical, Colorimetry, Edetic Acid, Free Radicals, Hydroxylation, Oxidation-Reduction, Sulfhydryl Compounds, Superoxides, Thiocarbamates, Xanthine Oxidase, Chemical Phenomena
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