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Radical–radical reactions of superoxide: a potential route to toxicity
Abstract
Superoxide reacts with many radicals, such as phenoxyl radicals, at near diffusion-controlled rates. These reactions are usually considered to be repair processes and have received little biological attention. However, addition of superoxide to give hydroperoxides and secondary oxidation products can also occur. The relative contributions of addition and repair vary depending on the properties of the phenol. With tyrosine, addition to give tyrosine hydroperoxide predominates, but in peptides the efficiency of hydroperoxide formation depends on the proximity of free amine groups. Radicals from other phenolic compounds, such as alpha-tocopherol and serotonin, also undergo addition reactions with superoxide. Physiologically, these reactions are likely to be more significant than dimerization when both radicals are generated together. They warrant attention as potential contributors to superoxide toxicity.
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“The hydroperoxide, due to the resonant forms of Tyr, can be formed in the ortho or para position with respect to the phenoxyl radical [138,139,140], Figure 51 and Figure 52.”
From Superoxide Anion Chemistry—Its Role at the Core of the Innate Immunity (2023) · cites this paper as [138]
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Regulation of the Redox Environment
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Metadata
- Authors
- Winterbourn, C. C., & Kettle, A. J.
- Corresponding author
- Winterbourn, Christine C.
- Venue
- Biochemical and Biophysical Research Communications
- Publisher
- Elsevier BV
- Published
- 2003-06
- Volume
- 305
- Issue
- 3
- Pages
- 729-736
- ISSN
- 0006-291X (ISSN-L)
- OpenAlex
- W1967305386
- Cited by
- 118
- References
- 76
- Citations by year
- 2026: 3 · 2025: 2 · 2024: 2 · 2023: 6 · 2022: 2 · 2021: 7 · 2020: 3 · 2019: 3 · 2018: 2 · 2017: 4 · 2016: 3 · 2015: 6 · 2014: 10 · 2013: 4 · 2012: 8
- FWCI
- 4.92
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Biochemical and Biophysical Research Communications (publishedVersion)
- PubMed (publishedVersion)
- Funders
- Health Research Council of New Zealand
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Free Radicals and Antioxidants
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Redox biology and oxidative stress
- Health Sciences › Medicine › Biochemistry (medical) › Antioxidant Activity and Oxidative Stress
- Keywords
- superoxide, phenoxyl radicals, radical-radical reactions, hydroperoxide formation, phenol oxidation, alpha-tocopherol, serotonin, radical dimerization, diffusion-controlled reaction
- MeSH terms
- Animals, Free Radicals, Indoles, Models, Chemical, Nitric Oxide, Peptides, Peroxides, Phenols, Proteins, Superoxides, Tyrosine, Vitamin E
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