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Characterization of Sulfur-centered Radical Intermediates Formed during the Oxidation of Thiols and Sulfite by Peroxynitrite
Open accessAbstract
Using a novel phosphorylated spin trap, 5-diethoxy-phosphoryl-5-methyl-1-pyrroline N-oxide (DEPMPO), an analog of the commonly used trap 5,5'-dimethyl-1-pyrroline N-oxide (DMPO), we have investigated the reactions of sulfur-centered radicals produced from the oxidation of thiols and sulfite by peroxynitrite. The predominant species trapped in all cases are the corresponding sulfur-centered radicals, i.e. glutathionyl radical (GS) from glutathione (GSH), N-acetyl-DL-penicillamine thiyl radical (S-NAP) from N-acetyl-DL-penicillamine (NAP) and sulfate anion radical (SO3-) from sulfite. These radicals consume molecular oxygen forming either peroxyl or superoxide anion radicals. GS, S-NAP, and (SO3-)-derived radicals react with ammonium formate to form the carbon dioxide anion radical (CO2-). Further support of spin adduct assignments and radical reactions are obtained from photolysis of S-nitrosoglutathione and S-nitroso-N-acetyl-DL-penicillamine. We conclude that the direct reaction of peroxynitrite with thiols and sulfate forms thiyl and sulfate anion radicals, respectively, by a hydroxyl radical-independent mechanism. Pathological implications of thiyl radical formation and subsequent oxyradical-mediated chain reactions are discussed. Oxygen activation by thiyl radicals formed during peroxynitrite-mediated oxidation of glutathione may limit the effectiveness of GSH against peroxynitrite-mediated toxicity in cellular systems.
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“Compounds containing sulfur are usually good antioxidants able to accommodate unpaired electron(s), which in turn result in the formation of thiyl radicals (GS·), whose lifetime is rather high and therefore damage to biological molecules is very mild (Karoui et al. 1996)22”
From Reactive Oxygen Species, Toxicity, Oxidative Stress, and Antioxidants: Chronic Diseases and Aging (2023) · cites this paper as Karoui et al. 1996
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Metadata
- Authors
- Karoui, H., Hogg, N., Fréjaville, C., Tordo, P., & Kalyanaraman, B.
- Affiliations
- Medical College of Wisconsin (US)
- Centre National de la Recherche Scientifique (FR)
- Venue
- Journal of Biological Chemistry
- Publisher
- Elsevier BV
- Published
- 1996-03
- Volume
- 271
- Issue
- 11
- Pages
- 6000-6009
- ISSN
- 0021-9258 (ISSN-L)
- OpenAlex
- W1602425415
- Cited by
- 231
- References
- 2
- Citations by year
- 2026: 5 · 2025: 2 · 2024: 4 · 2023: 4 · 2022: 3 · 2021: 6 · 2020: 5 · 2019: 3 · 2018: 3 · 2017: 3 · 2016: 10 · 2015: 4 · 2014: 5 · 2013: 6 · 2012: 8
- FWCI
- 5.41
- Type
- journal article
- Language
- en
- Open access
- hybrid
- doi.org
- Licence
- Locations
- Journal of Biological Chemistry (publishedVersion, cc-by)
- PubMed (publishedVersion)
- Funders
- National Institutes of Health (5r29hl045058-03, 5r01hl047250-09)
- National Heart, Lung, and Blood Institute (HL 47250, HL45058)
- National Center for Research Resources (P41RR001008, RR 01008)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Redox biology and oxidative stress
- Physical Sciences › Chemistry › Spectroscopy › Electron Spin Resonance Studies
- Physical Sciences › Chemistry › Organic Chemistry › Free Radicals and Antioxidants
- Keywords
- peroxynitrite, thiyl radicals, sulfur radicals, glutathione oxidation, sulfite oxidation, DEPMPO, spin trapping, superoxide, peroxy radicals, S-nitrosoglutathione, S-nitroso-N-acetylpenicillamine, oxygen activation
- MeSH terms
- Cyclic N-Oxides, Electron Spin Resonance Spectroscopy, Formates, Free Radicals, Glutathione, Nitrates, Oxidation-Reduction, Penicillamine, Spin Labels, Sulfhydryl Compounds, Sulfites, Molecular Structure, Hydroxyl Radical, In Vitro Techniques
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