Cited by 1,511Nitric Oxide and Endothelin EffectsRedox biology and oxidative stressFree Radicals and Antioxidants

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The chemistry of peroxynitrite: a product from the reaction of nitric oxide with superoxide

Pryor, W. A., Squadrito, G. L.·1995·American Journal of Physiology-Lung Cellular and Molecular Physiology

DOI 10.1152/ajplung.1995.268.5.l699

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Abstract

Nitric oxide and superoxide, which are produced by several cell types, rapidly combine to form peroxynitrite. This reaction can result in nitric oxide scavenging, and thus mitigation of the biological effects of superoxide. Also, superoxide can trap and hence modulate the effects of nitric oxide; superoxide dismutase, by controlling superoxide levels, therefore can influence the reaction pathways open to nitric oxide. The production of peroxynitrite, however, causes its own sequelae of events: Although neither .NO nor superoxide is a strong oxidant, peroxynitrite is a potent and versatile oxidant that can attack a wide range of biological targets. The peroxynitrite anion is relatively stable, but its acid, peroxynitrous acid (HOONO), rearranges to form nitrate with a half-life of approximately 1 s at pH 7, 37 degrees C. HOONO exists as a Boltzmann distribution of rotamers; at 5-37 degrees C HOONO has an apparent acidity constant, pKa,app, of 6.8. Oxidation reactions of HOONO can involve two-electron processes (such as an SN2 displacement) or a one-electron transfer (ET) reaction in which the substrate is oxidized by one electron and peroxynitrite is reduced. These oxidation reactions could involve one of two mechanisms. The first mechanism is homolysis of HOONO to give HO. and .NO2, which initially are held together in a solvent cage. This caged pair of radicals (the "geminate" pair) can either diffuse apart, giving free radicals that can perform oxidations, or react together either to form nitrate or to reform HOONO (a process called cage return). A large amount of cage return can explain the small entropy of activation (Arrhenius A-factor) observed for the decomposition of HOONO. A cage mechanism also can explain the residual yield of nitrate that appears to be formed even in the presence of high concentrations of all of the scavengers studied to date, since scavengers capture only free HO. and .NO2 and not caged radicals. If the cage mechanism is correct, the rate of disappearance of peroxynitrite be slower in solvents of higher viscosity, and we do not find this to be the case. The second mechanism is that an activated isomer of peroxynitrous acid, HOONO*, can be formed in a steady state. The HOONO* mechanism can explain the inability of hydroxyl radical scavengers to completely block either nitrate formation or the oxidation of substrates such as methionine, since HOONO* would be less reactive, and therefore more selective, than the hydroxyl radical itself.(ABSTRACT TRUNCATED AT 400 WORDS)

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“Interestingly, in in vivo studies, the role of peroxynitrite has also been implicated in various experimental models of NO-mediated cellular injuries (17, 18).”
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Generation of peroxynitrite in localised, moderate temperature burns
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“Furthermore, an approximated amount of SOD was added in order to eliminate the excess O2 ·− produced in the system, which has a reaction rate constant of 2 × 10(9) L mol s with O2 ·− and will rapidly capture the excess O2 ·− [38].”
Background
Comparison of chicoric acid, and its metabolites caffeic acid and caftaric acid: In vitro protection of biological macromolecules and inflammatory responses in BV2 microglial cells
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“Thus, a bolus addition of micromolar ONOO is misleading because upon addition of a tiny volume of ONOO stock solution to a buffered protein solution at physiological pH, ONOO either reacts with protein target or isomerizes to form nitrate ion within seconds (Pryor and Squadrito, 1995; Radi, 1998; Radi et al., 1991)(Fi…”
Background
OLEIC ACID-INDUCED LUNG INJURY IN RATS AND EFFECTS OF CAFFEIC ACID PHENETHYL ESTER
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Human peripheral blood polymorphonuclear leukocytes at the ovulatory period are in an activated state
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“To estimate the amounts of NO, the total chemiluminescence values were subtracted the values in the presence of carboxy-PTIO (Wanikiat et al., 1997; Pryor and Squadrito, 1995).”
Method
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Hyperglycemia enhances the generation of ROS and RNS that impair antioxidant power and cause oxidative damage in human erythrocytes
Qasim, N., Arif, A., & Mahmood, R. (2022) · Biochemistry and Cell Biology · doi:10.1139/bcb-2022-0008 · Cited by 22
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Nitric Oxide and Peroxynitrite Affect Differently Acetylcholine Release, Choline Acetyltransferase Activity, Synthesis, and Compartmentation of Newly Formed Acetylcholine inTorpedo marmorataSynaptosomes
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(1→3)-β-d-Glucan reduces the damages caused by reactive oxygen species induced in human platelets by lipopolysaccharides
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ANTIOXIDANT-PROOXIDANT BALANCE IN THE INTESTINE: FOOD FOR THOUGHT 1. PROOXIDANTS
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Recombinant heat shock protein 27 (HSP27/HSPB1) protects against cadmium-induced oxidative stress and toxicity in human cervical cancer cells
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“PN is formed spontaneously from the following reaction: O2 − + NO ➔ ONOO− (Pryor and Squadrito 1995).”
BackgroundInfluential
Synthetic Fluorescent Probes for Imaging of Peroxynitrite and Hypochlorous Acid in Living Cells
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“1 3 peroxynitrite, have been described [35].”
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“ONOO is considered an endogenously formed cytotoxic factor derived from nitric oxide (N _ O) and superoxide anion ð _ O 2 Þ [17, 18].”
Background
Peroxynitrite does not impair pulmonary and systemic vascular responses
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“Superoxide anion quenches NO to give peroxynitrite (32) and thereby reduces NO availability.”
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Authors: Pryor, W. A., & Squadrito, G. L.
Affiliations: Louisiana State University (US)
Venue: American Journal of Physiology-Lung Cellular and Molecular Physiology
Publisher: American Physiological Society
Published: 1995-05-01
Volume: 268
Issue: 5
Pages: L699-L722
ISSN: 1040-0605 (ISSN-L)
1522-1504
DOI: 10.1152/ajplung.1995.268.5.l699
OpenAlex: W2209831038
Cited by: 1,511
References: 94
Citations by year: 2026: 11 · 2025: 13 · 2024: 19 · 2023: 21 · 2022: 21 · 2021: 19 · 2020: 24 · 2019: 28 · 2018: 29 · 2017: 30 · 2016: 30 · 2015: 35 · 2014: 42 · 2013: 55 · 2012: 47
FWCI: 52.08
Type: journal article
Language: en
Open access: closed
Locations: American Journal of Physiology-Lung Cellular and Molecular Physiology (publishedVersion)
PubMed (publishedVersion)
Topics: Health Sciences › Medicine › Physiology (medical) › Nitric Oxide and Endothelin Effects
Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Redox biology and oxidative stress
Physical Sciences › Chemistry › Organic Chemistry › Free Radicals and Antioxidants
Keywords: peroxynitrite, nitric oxide, superoxide, peroxynitrous acid, nitrate formation, superoxide dismutase, nitric oxide scavenging, single electron transfer, two-electron oxidation, peroxynitrite decomposition, hydroxyl radical scavengers, nitric oxide synthase, nitric oxide signaling
MeSH terms: Animals, Humans, Hydrogen-Ion Concentration, Hydroxylation, Methionine, Nitrates, Nitric Oxide, Nitroso Compounds, Oxidation-Reduction, Sulfhydryl Compounds, Superoxides, Viscosity

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The chemistry of peroxynitrite: a product from the reaction of nitric oxide with superoxide

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