Characterization of Sulfur-centered Radical Intermediates Formed during the Oxidation of Thiols and Sulfite by Peroxynitrite
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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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Sulfur-containing compounds are usually good antioxidants able to accommodate unpaired electron(s), forming thiyl radicals (GS·) with rather high lifetime and therefore very mild damage to biological molecules.
“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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Rashdan, N. A., Shrestha, B., & Pattillo, C. B. (2020) · Redox Biology · doi:10.1016/j.redox.2020.101693 · Cited by 63 · see citing works
“Nucleophilic attack can also lead to the formation of thiyl radicals [51,52] which react with GSH and O2 to form P-SSG [53].”
BackgroundS-Glutathiolation in life and death decisions of the cell
Dalle‐Donne, I., Colombo, G., Gagliano, N., Colombo, R., Giustarini, D., Rossi, R., & Milzani, A. (2010) · Free Radical Research · doi:10.3109/10715762.2010.515217 · Cited by 59 · see citing works
“Therefore, P-SSG can arise from reactions between GSH and P-SNO (Figure 1, mechanism G) or from reactions between P-SH and S -nitrosothiols such as GSNO (Figure 1, mechanism H).”
BackgroundInfluentialHexavalent chromium causes the oxidation of thioredoxin in human bronchial epithelial cells
Myers, J. M., Antholine, W. E., & Myers, C. R. (2008) · Toxicology · doi:10.1016/j.tox.2008.01.017 · Cited by 58 · see citing works
“In the presence of 5% ethanol, a specific hydroxyl radical scavenger, the DEPMPO/•OH adduct signal decreased by 50% whereas that for DEPMPO/•SG decreased by 30% (not shown).”
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“In in vitro studies, it has been established that antioxidants such as glutathione, ascorbic acid, and alpha-tocopherol are scavengers of peroxynitrite and inhibitors of its oxidant capacity [17,18].”
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A comparison of the NADPH oxidase in human sperm and white blood cells
Armstrong, J. S., Bivalacqua, T. J., Chamulitrat, W., Sikka, S. C., & Hellstrom, W. J. G. (2002) · International Journal of Andrology · doi:10.1046/j.1365-2605.2002.00351.x · Cited by 56 · see citing works
The protective role of endogenous glutathione in carrageenan-induced pleurisy in the rat
Cuzzocrea, S., Costantino, G., Zingarelli, B., et al. (1999) · European Journal of Pharmacology · doi:10.1016/s0014-2999(99)00200-9 · Cited by 54 · see citing works
Protein thiyl radical reactions and product formation: a kinetic simulation
Nauser, T., Koppenol, W. H., & Schöneich, C. (2014) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2014.12.006 · Cited by 53 · see citing works
Li, R., Dong, H., Tian, R., et al. (2020) · Separation and Purification Technology · doi:10.1016/j.seppur.2020.117230 · Cited by 51 · see citing works
Skeletal muscles, heart, and lung are the main sources of oxygen radicals in old rats
Kozlov, A. V., Szalay, L., Umar, F., Kropik, K., Staniek, K., Niedermüller, H., Bahrami, S., & Nohl, H. (2004) · Biochimica et Biophysica Acta (BBA) - Molecular Basis of Disease · doi:10.1016/j.bbadis.2004.11.004 · Cited by 51 · see citing works
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“9 G obtained from the simulated spectrum are assigned to the DEPMPO/GS+ adduct [27].”
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Review Article: Oxidative Stress Versus Antioxidants
Al-Dalaen, S. (2014) · American Journal of Bioscience and Bioengineering · doi:10.11648/j.bio.20140205.11 · Cited by 50 · see citing works
“The antioxidant capacity of thiol compounds is attributed to the presence of sulfur atom, which can easily accommodate the loss of a single electron [124].”
Background
- 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
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Biophysics › 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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