Cited by 137Antioxidant Activity and Oxidative StressRedox biology and oxidative stressFree Radicals and Antioxidants

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Linoleic acid hydroperoxide reacts with hypochlorous acid, generating peroxyl radical intermediates and singlet molecular oxygen

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Miyamoto, Sayuri, Martinez, Glaucia R., Rettori, Daniel, Augusto, Ohara, Medeiros, Marisa H. G., Di Mascio, Paolo·2006·Proceedings of the National Academy of Sciences

DOI 10.1073/pnas.0508170103PMC PMC1326168

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Abstract

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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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)
ORCID: Miyamoto, Sayuri
Medeiros, Marisa H. G.
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
DOI: 10.1073/pnas.0508170103
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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Linoleic acid hydroperoxide reacts with hypochlorous acid, generating peroxyl radical intermediates and singlet molecular oxygen

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