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Linoleic acid hydroperoxide reacts with hypochlorous acid, generating peroxyl radical intermediates and singlet molecular oxygen
Open accessAbstract
The reaction of hypochlorous acid (HOCl) with hydrogen peroxide is known to generate stoichiometric amounts of singlet molecular oxygen [O2 (1Deltag)]. This study shows that HOCl can also react with linoleic acid hydroperoxide (LAOOH), generating O2 (1Deltag) with a yield of 13 +/- 2% at physiological pH. Characteristic light emission at 1,270 nm, corresponding to O2 (1Deltag) monomolecular decay, was observed when HOCl was reacted with LAOOH or with liposomes containing phosphatidylcholine hydroperoxides, but not with cumene hydroperoxide or tert-butyl hydroperoxide. The generation of O2 (1Deltag) was confirmed by the acquisition of the spectrum of the light emitted in the near-infrared region showing a band with maximum intensity at 1,270 nm and by the observation of the enhancing effect of deuterium oxide and the quenching effect of sodium azide. Mechanistic studies using 18O-labeled linoleic acid hydroperoxide (LA18O18OH) showed that its reaction with HOCl yields 18O-labeled O2 (1Deltag) [18O2 (1Deltag)], demonstrating that the oxygen atoms in O2 (1Deltag) are derived from the hydroperoxide group. Direct analysis of radical intermediates in the reaction of LAOOH with HOCl by continuous-flow electron paramagnetic resonance spectroscopy showed a doublet signal with a g-value of 2.014 and a hyperfine coupling constant from the alpha-hydrogen of a(H) = 4.3 G, indicating the formation of peroxyl radicals. Taken together, our results clearly demonstrate that HOCl reacts with biologically relevant lipid hydroperoxides, generating O2 (1Deltag). In addition, the detection of 18O2 (1Deltag) and peroxyl radicals strongly supports the involvement of a Russell mechanism in the generation of O2 (1Deltag).
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“HOCl-dependent formation of highly reactive photoexcited molecular oxygen [1O2 (singlet oxygen)] has been documented without mechanistic involvement of photons downstream of peroxide (including linoleic acid hydroperoxide), superoxide, or chloramine chemistry involving the chemical formation of photo-excited states (commonly referred to as ‘chemiexcitation’) (69–71).”
From Hypochlorous Acid: From Innate Immune Factor and Environmental Toxicant to Chemopreventive Agent Targeting Solar UV-Induced Skin Cancer (2022) · cites this paper as [69]
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Metadata
- Authors
- Miyamoto, S., Martinez, G. R., Rettori, D., Augusto, O., Medeiros, M. H. G., & Di Mascio, P.
- Affiliations
- Universidade de São Paulo (BR)
- Departamento de Bioquímica, Instituto de Química, Universidade de São Paulo, CP26077, CEP 05513-970, São Paulo, Brazil
- National Institutes of Health (US)
- Venue
- Proceedings of the National Academy of Sciences
- Publisher
- National Academy of Sciences
- Published
- 2005-12-30
- Volume
- 103
- Issue
- 2
- Pages
- 293-298
- ISSN
- 0027-8424 (ISSN-L)
- 1091-6490
- PMC
- PMC1326168
- OpenAlex
- W2011222045
- Cited by
- 137
- References
- 69
- Citations by year
- 2026: 1 · 2025: 2 · 2024: 7 · 2023: 9 · 2022: 2 · 2021: 7 · 2020: 9 · 2019: 13 · 2018: 3 · 2017: 12 · 2016: 8 · 2015: 8 · 2014: 10 · 2013: 8 · 2012: 7
- FWCI
- 2.55
- Type
- journal article
- Language
- en
- Open access
- green
- www.ncbi.nlm.nih.gov
- Locations
- Proceedings of the National Academy of Sciences (publishedVersion)
- Europe PMC (PubMed Central) (publishedVersion)
- PubMed Central (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Health Sciences › Medicine › Biochemistry (medical) › Antioxidant Activity and Oxidative Stress
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Redox biology and oxidative stress
- Physical Sciences › Chemistry › Organic Chemistry › Free Radicals and Antioxidants
- Keywords
- singlet oxygen, hypochlorous acid, linoleic acid hydroperoxide, lipid hydroperoxides, peroxy radicals, phosphatidylcholine hydroperoxide, liposomes, electron spin resonance
- MeSH terms
- Hydrogen Peroxide, Hydrogen-Ion Concentration, Hypochlorous Acid, Linoleic Acids, Lipid Peroxides, Liposomes, Peroxides, Phospholipids, Spectrum Analysis, Molecular Structure, Singlet Oxygen
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