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Activity of thiols as singlet molecular oxygen quenchers
Abstract
Singlet molecular oxygen O2(1 delta g) arising from the thermodissociation of the endoperoxide of 3,3'-(1,4-naphthylidene) dipropionate (NDPO2) was used to assess the quenching ability of various thiols and related compounds in sodium phosphate buffer in D2O at 37 degrees C. The overall quenching ability decreases in the sequence ergothioneine, methionine, cysteine, beta,beta-dimethyl cysteine (penicillamine), mercaptopropionylglycine, mesna, glutathione (GSH), dithiothreitol, N-acetyl cysteine and captopril. Cystine, glutathione disulphide, dimesna, methionine sulphone and methionine sulphoxide have no quenching effect. Comparison of the rate constants for physical (kq) with chemical (kr) quenching by thiols indicates that chemical reactivity accounts fully for their ability to quench O2(1 delta g), and pD dependence indicates that the thiolate anion reacts with O2(1 delta g). Loss of thiol groups, as exemplified by GSH, is not affected by the free radical scavengers superoxide dismutase and mannitol. However, sodium azide, a scavenger of O2(1 delta g), completely prevents NDPO2-induced thiol depletion. Depletion of GSH by NDPO2 is accompanied by the formation of its disulphide, sulphinate, sulphonate, sulphoxide and other products.
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“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 [234]
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Pecci, L., Costa, M., Montefoschi, G., Antonucci, A. M., & Cavallini, D. (1999) · Biochemical and Biophysical Research Communications · doi:10.1006/bbrc.1998.9886 · Cited by 28
[58] Antioxidant action of stobadine
Horáková, Ľ., Sies, H., & Steenken, S. (1994) · Methods in enzymology on CD-ROM/Methods in enzymology · doi:10.1016/0076-6879(94)34129-x · Cited by 28
Self-citationGirard, P.-M., Graindorge, D., Smirnova, V., Rigolet, P., Francesconi, S., Scanlon, S. E., & Sage, É. (2013) · PLoS ONE · doi:10.1371/journal.pone.0075751 · Cited by 29
van den Broeke, L. T., & van Henegouwen, G. M. J. B. (1995) · International Journal of Radiation Biology · doi:10.1080/09553009514550471 · Cited by 27
Mascio, P. D., Kaiser, S., Devasagayam, T. P. A., & Sies, H. (1991) · Advances in experimental medicine and biology · doi:10.1007/978-1-4684-5877-0_7 · Cited by 25
Self-citationSantos, F. D. S., da Silveira, C. H., Nunes, F. S., Ferreira, D. C., Victória, H. F. V., Krambrock, K., Chaves, O. A., Rodembusch, F. S., & Iglesias, B. A. (2020) · Dalton Transactions · doi:10.1039/d0dt01063d · Cited by 25
Metadata
- Authors
- Devasagayam, T. P. A., Sundquist, A. R., Di Mascio, P., Kaiser, S., & Sies, H.
- Affiliations
- Heinrich Heine University Düsseldorf (DE)
- Corresponding author
- Sies, Helmut
- ORCID
- Sies, Helmut
- Venue
- Journal of Photochemistry and Photobiology B: Biology
- Publisher
- Elsevier BV
- Published
- 1991-04
- Volume
- 9
- Issue
- 1
- Pages
- 105-116
- ISSN
- 1011-1344 (ISSN-L)
- OpenAlex
- W1997822338
- Cited by
- 175
- References
- 34
- Citations by year
- 2026: 4 · 2025: 6 · 2024: 5 · 2023: 4 · 2022: 3 · 2021: 8 · 2020: 9 · 2019: 6 · 2018: 7 · 2017: 3 · 2016: 7 · 2015: 7 · 2014: 10 · 2013: 6 · 2012: 6
- FWCI
- 2.03
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of Photochemistry and Photobiology B Biology (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Redox biology and oxidative stress
- Physical Sciences › Chemistry › Organic Chemistry › Free Radicals and Antioxidants
- Health Sciences › Medicine › Biochemistry (medical) › Antioxidant Activity and Oxidative Stress
- Keywords
- singlet oxygen, glutathione depletion, glutathione disulfide, chemical quenching, physical quenching, thiolate anion, sodium azide, superoxide dismutase, mannitol, mesna, N-acetylcysteine, cysteine, methionine, ergothioneine, D-penicillamine, dithiothreitol, captopril
- MeSH terms
- Glutathione, Oxidation-Reduction, Oxygen, Photochemistry, Sulfhydryl Compounds, Singlet Oxygen
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