Cited by 176Redox biology and oxidative stressFree Radicals and AntioxidantsAntioxidant Activity and Oxidative Stress

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Activity of thiols as singlet molecular oxygen quenchers

Devasagayam, Thomas P.A., Sundquist, Alfred R., Di Mascio, Paolo, Kaiser, Stephan, Sies, Helmut·1991·Journal of Photochemistry and Photobiology B: Biology

DOI 10.1016/1011-1344(91)80008-6

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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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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)
DOI: 10.1016/1011-1344(91)80008-6
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
Licence: www.elsevier.com/tdm/userlicense/1.0/ (tdm)
www.elsevier.com/legal/tdmrep-license (tdm)
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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Activity of thiols as singlet molecular oxygen quenchers

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