Cited by 801Redox biology and oxidative stressFree Radicals and AntioxidantsAntioxidant Activity and Oxidative Stress

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Reactivity of biologically important thiol compounds with superoxide and hydrogen peroxide

Winterbourn, Christine C., Metodiewa, Diana·1999·Free Radical Biology and Medicine

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Abstract

The reactivities of glutathione, cysteine, cysteamine, penicillamine, N-acetylcysteine, dithiothreitol and captopril with superoxide generated from xanthine oxidase and hypoxanthine, and with reagent hydrogen peroxide, have been investigated. Rates of thiol loss on adding hydrogen peroxide, and superoxide-dependent thiol loss and oxygen uptake were measured. The relative reactivities of the different thiols with both oxidants were inversely related to the pK of the thiol group, such that at pH 7.4, penicillamine was the most reactive. N-acetylcysteine weakly reactive and no reaction was seen with captopril. For hydrogen peroxide, the calculated rate constants for the reaction with the thiolate anion all fell within the range 18-26 M(-1) s(-1). With superoxide, our results are consistent with each thiol reacting via a short chain that consumes oxygen and regenerates superoxide. Only with some of the thiols, was the consumed oxygen recovered as hydrogen peroxide. Reported values for the rate constant for the reaction of thiols with superoxide vary over four orders of magnitude, with the highest being > 10(5) M(-1) s(-1). Due to the complexity of the chain reaction, no study so far has been able to obtain accurate values and we consider the best estimates to be in the 30 to 1000 M(-1) s(-1) range.

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Authors: Winterbourn, C. C., & Metodiewa, D.
Corresponding author: Winterbourn, Christine C.
ORCID: Winterbourn, Christine C.
Venue: Free Radical Biology and Medicine
Publisher: Elsevier BV
Published: 1999-08
Volume: 27
Issue: 3-4
Pages: 322-328
ISSN: 0891-5849 (ISSN-L)
DOI: 10.1016/s0891-5849(99)00051-9
OpenAlex: W2056840435
Cited by: 799
References: 43
Citations by year: 2026: 10 · 2025: 24 · 2024: 23 · 2023: 37 · 2022: 28 · 2021: 32 · 2020: 38 · 2019: 43 · 2018: 34 · 2017: 40 · 2016: 43 · 2015: 49 · 2014: 41 · 2013: 48 · 2012: 45
FWCI: 3.99
Type: journal article
Language: en
Open access: closed
Licence: www.elsevier.com/tdm/userlicense/1.0/ (tdm)
Locations: Free Radical Biology and Medicine (publishedVersion)
PubMed (publishedVersion)
Funders: Health Research Council of New Zealand
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: thiol oxidation, superoxide, hydrogen peroxide, glutathione, cysteine, cysteamine, D-penicillamine, N-acetylcysteine, dithiothreitol, captopril, xanthine oxidase, thiolate anion, thiol reactivity, thiol pKa, oxygen consumption, chain reaction, rate constants
MeSH terms: Acetylcysteine, Angiotensin-Converting Enzyme Inhibitors, Captopril, Cysteamine, Cysteine, Dithiothreitol, Glutathione, Hydrogen Peroxide, Oxygen Consumption, Penicillamine, Sulfhydryl Compounds, Superoxides, Xanthine Oxidase, Reactive Oxygen Species

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Reactivity of biologically important thiol compounds with superoxide and hydrogen peroxide

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