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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“…et al., 2001) and it has been recently suggested that some of the cytotoxic effects of NO are tightly related to the production of peroxynitrite, an high-energy oxidant deriving by the rapid reaction of NO with superoxide (Beckman et al., 1990; Crow & Beckman, 1995; Pryor & Squadrito, 1995).”
Background
Vascular Peroxynitrite Formation during Organic Nitrate Tolerance
Mihm, M., Coyle, C. M., Jing, L., & Bauer, J. A. (1999) · Journal of Pharmacology and Experimental Therapeutics · doi:10.1016/s0022-3565(24)35088-8 · Cited by 47
“O2 . interacts with NO in a diffusion rate-limited reaction to form peroxynitrite (ONOO2), a potent cellular toxicant (Pryor and Squadrito, 1995; Beckman and Koppenol, 1996).”
Peroxynitrite-mediated modification of fibrinogen affects platelet aggregation and adhesion
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“Peroxynitrite was synthesized according to the method of Pryor and Squadrito.(27) Freeze fractionation (–70°C) of the peroxynitrite solution formed a yellow top layer, which was retained for further studies.”
Method
N-Acetylcysteine Amide Protects Renal Proximal Tubular Epithelial Cells against Iohexol-Induced Apoptosis by Blocking p38 MAPK and iNOS Signaling
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Delivery of Antioxidant and Anti-inflammatory Agents for Tissue Engineered Vascular Grafts
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“For example, high concentrations of the reaction product peroxynitrite can result in cytotoxic peroxynitrous acid (Pryor and Squadrito, 1995), hydroxyl radical toxicity (Beckman et al.”
Background
Pro-oxidative activity of nitroxides in their reactions with glutathione
Głębska, J., Skolimowski, J. J., Kudzin, Z. H., Gwoździński, K., Grzelak, A., & Bartosz, G. (2003) · Free Radical Biology and Medicine · doi:10.1016/s0891-5849(03)00306-x · Cited by 46
Residual Oil Fly Ash Increases the Susceptibility to Infection and Severely Damages the Lungs after Pulmonary Challenge with a Bacterial Pathogen
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“NO combines with the reactive oxygen intermediate, superoxide anion, to form the highly reactive substance, peroxynitrite (Pryor and Squadrito, 1995).”
Background
The selective inhibition of inducible nitric oxide synthase prevents intestinal ischemia–reperfusion injury in mice
Barocelli, E., Ballabeni, V., Ghizzardi, P., Cattaruzza, F., Bertoni, S., Lagrasta, C. A. M., & Impicciatore, M. (2006) · Nitric Oxide · doi:10.1016/j.niox.2005.11.006 · Cited by 46
The decomposition of peroxynitrite to nitroxyl anion (NO-) and singlet oxygen in aqueous solution
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Chemical Modification of Proteins by Reactive Oxygen Species
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“, 1992; Ischiropoulos and AlMedi, 1995) and to oxidize methionine residues (Pryor et al., 1994; Pryor and Squadrito, 1995; Berlett et al., 1998) and cysteine residues (Gatti et al.”
Background
Just say NO to inhaled nitric oxide for the acute respiratory distress syndrome
Matthay, M. A., Pittet, J., & Jayr, C. (1998) · Critical Care Medicine · doi:10.1097/00003246-199801000-00001 · Cited by 46
Melatonin improves mitochondrial respiratory chain activity and liver morphology in ob/ob mice
Solís‐Muñoz, P., Solis-Herruzo, J. A., Fernández-Moreira, D., Gómez-Izquierdo, É., García‐Consuegra, I., Muñoz‐Yagüe, T., & García‐Ruíz, I. (2011) · Journal of Pineal Research · doi:10.1111/j.1600-079x.2011.00868.x · Cited by 45
“The combination of both, superoxide and nitric oxide, leads to the formation of peroxynitrite [8], which can nitrate tyrosine residues within mitochondrial proteins and cause degradation of mitochondrial complexes and the loss of MRC activity [9, 10].”
Background
Thiol redox biochemistry: insights from computer simulations
Zeida, A., Guardia, C. M. A., Lichtig, P., Perissinotti, L. L., Defelipe, L. A., Turjanski, A. G., Radí, R., Trujillo, M., & Estrin, D. A. (2014) · Biophysical Reviews · doi:10.1007/s12551-013-0127-x · Cited by 45
Superoxide dismutase expression and H2O2 production by hemocytes of the trematode intermediate host Lymnaea stagnalis (Gastropoda)
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Peroxynitrite: a potent oxidizing and nitrating agent.
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Thiols and disulphides can aggravate peroxynitrite‐dependent inactivation of α1‐antiproteinase
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Increased nitric oxide formation in recurrent thrombotic microangiopathies: A possible mediator of microvascular injury
Noris, M., Ruggenenti, P. L., Todeschini, M., Figliuzzi, M., Macconi, D., Zoja, C., Paris, S., Gaspari, F., & Remuzzi, G. (1996) · American Journal of Kidney Diseases · doi:10.1016/s0272-6386(96)90515-6 · Cited by 45
Biological Effects of Electrical Discharge Plasma in Water and in Gas–Liquid Environments
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Nitration of tyrosines 46 and 48 induces the specific degradation of cytochrome c upon change of the heme iron state to high-spin
Díaz‐Moreno, I., García-Heredia, J. M., Díaz-Quintana, A., Teixeira, M. S., & la Rosa, M. Á. D. (2011) · Biochimica et Biophysica Acta (BBA) - Bioenergetics · doi:10.1016/j.bbabio.2011.09.012 · Cited by 46
“Actually, the enhanced nitric oxide synthesis is related to nitrotyrosine formation [7–10], which has been detected in disease-affected tissues [11–16] under nitro-oxidative stress.”
Background
Specific nitration of tyrosines 46 and 48 makes cytochrome c assemble a non‐functional apoptosome
García-Heredia, J. M., Díaz‐Moreno, I., Díaz-Quintana, A., Orzáez, M., Navarro, J. A., Hervás, M., & la Rosa, M. Á. D. (2011) · FEBS Letters · doi:10.1016/j.febslet.2011.12.007 · Cited by 45
“proteins [5–8], but its lifetime is long enough to cross the membrane and react with biomolecules in other compartments [5,6].”
Background
The neuronal toxicity of sulfite plus peroxynitrite is enhancede by glutathione depletion: implications for Parkinson’s disease
Marshall, K., Reist, M., Jenner, P. G., & Halliwell, B. B. (1999) · Free Radical Biology and Medicine · doi:10.1016/s0891-5849(99)00094-5 · Cited by 44
The neuronal nitric oxide synthase inhibitor NANT blocks acetaminophen toxicity and protein nitration in freshly isolated hepatocytes
Banerjee, S., Melnyk, S. B., Krager, K. J., Aykin‐Burns, N., Letzig, L. G., James, L. P., & Hinson, J. (2015) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2015.09.022 · Cited by 44
Cytoprotective mechanism of baicalin against endothelial cell damage by peroxynitrite
Kim, D. H., Chung, H. Y., Cho, K. H., Moon, S.-K., Kim, Y. S., Kim, D. H., & Choi, J. S. (2005) · Journal of Pharmacy and Pharmacology · doi:10.1211/jpp.57.12.0008 · Cited by 44
DNA damage of tumor-associated lymphocytes and total antioxidant capacity in cancerous patients
Liu, X., Zhao, J., & Zheng, R. (2003) · Mutation Research/Genetic Toxicology and Environmental Mutagenesis · doi:10.1016/s1383-5718(03)00112-8 · Cited by 43
Resveratrol protects against peroxynitrite-induced thiol oxidation in blood platelets.
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Direct measurement of nitric oxide release in gastric mucosa during ischemia-reperfusion in rats
Wada, K., Kamisaki, Y., Ohkura, T., Kanda, G., Nakamoto, K., Kishimoto, Y., Ashida, K., & Itoh, T. (1998) · American Journal of Physiology-Gastrointestinal and Liver Physiology · doi:10.1152/ajpgi.1998.274.3.g465 · Cited by 44
“The reaction of NO with superoxide radical to form the well-known oxidant peroxynitrite has been widely reported (2, 22, 23).”
Background
Stress Responses, Adaptation, and Virulence of Bacterial Pathogens During Host Gastrointestinal Colonization
Flint, A., Butcher, J., & Stintzi, A. (2016) · Microbiology Spectrum · doi:10.1128/microbiolspec.vmbf-0007-2015 · Cited by 44
“NO also reacts with superoxide anions to form peroxynitrate (ONOO − ) (equation 12), which rapidly oxidizes a variety of biologically relevant substrates or eventually decomposes to nitrate and carbonic acid (equation 13) (103, 107 – 109).”
Background
Role of ethanolic extract of Bacopa monnieri against 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) induced mice model via inhibition of apoptotic pathways of dopaminergic neurons
Singh, B., Pandey, S., Yadav, S. K., Verma, R., Singh, S. P., & Mahdi, A. A. (2017) · Brain Research Bulletin · doi:10.1016/j.brainresbull.2017.10.007 · Cited by 43
“Moreover, NO, an important secondary mediator of several biological functions significantly increases in MPTP exposed mice, causing formation of peroxynitrite, a potent oxidant, which attacks a wide range of biological targets (Beckman, 1996; Pryor and Squadrito, 1995).”
Nitrosylated Bovine Serum Albumin Derivatives as Pharmacologically Active Nitric Oxide Congeners
Ewing, J. F., Young, D. V., Janero, D. R., Garvey, D. S., & Grinnell, T. A. (1997) · Journal of Pharmacology and Experimental Therapeutics · doi:10.1016/s0022-3565(24)37070-3 · Cited by 43
Hypobaric hypoxia modifies constitutive nitric oxide synthase activity and protein nitration in the rat cerebellum
Serrano, J., Encinas, J. M., Salas, E., Fernández, A. P., Castro‐Blanco, S., Fernández‐Vizarra, P., Bentura, M. L., & Rodrigo, J. (2003) · Brain Research · doi:10.1016/s0006-8993(03)02691-x · Cited by 43
OXYGEN RADICALS AND NITRIC OXIDE IN RAT MESENTERIC ISCHAEMIA‐REPERFUSION: MODULATION BY L‐ARGININE AND NG‐NITRO‐L‐ARGININE METHYL ESTER
Haklar, G., Ulukaya‐Durakbaś, Ç., Yüksel, M., Dagh, T., & Yalçin, A. S. (1998) · Clinical and Experimental Pharmacology and Physiology · doi:10.1111/j.1440-1681.1998.tb02342.x · Cited by 43
Protective Role of Extracellular Superoxide Dismutase in Hemodialysis Patients
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Chapter 10 Improving the survival of grafted embryonic dopamine neurons in rodent models of Parkinson's disease
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Inhibition of Calpain Is a Component of Nitric Oxide-Induced Down-Regulation of Human Mast Cell Adhesion
Forsythe, P., & Befus, A. D. (2003) · The Journal of Immunology · doi:10.4049/jimmunol.170.1.287 · Cited by 43
“Peroxynitrite is thought to mediate many of the cytotoxic effects of NO (22, 23).”
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Microperoxidase 8 catalyzed nitration of phenol by nitrogen dioxide radicals
Ricoux, R., Boucher, J., Mansuy, D., & Mahy, J. (2001) · European Journal of Biochemistry · doi:10.1046/j.1432-1327.2001.02288.x · Cited by 43
“The reaction of ONOO (or ONOOH) with a variety of biomolecules also results in the production of NO2 2 [13].”
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Role of nitric oxide in intestinal ischaemia-reperfusion injury studied using electron paramagnetic resonance
Chan, K. K. L., Zhang, X. H., Fung, P. C. W., Guo, W., & Tam, P. K. H. (1999) · British journal of surgery · doi:10.1046/j.1365-2168.1999.01241.x · Cited by 43
Protective Effect of FK409, a Spontaneous Nitric Oxide Releaser, on Ischemic Acute Renal Failure in Rats
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“On the other hand, NO may be deleterious because of its reactivity with oxygen free radicals produced during reperfusion of the ischemic kidney to yield toxic products such as peroxynitrates (Pryor and Squadrito, 1995).”
Aerosolized manganese SOD decreases hyperoxic pulmonary injury in primates. I. Physiology and biochemistry
Simonson, S. G., Welty‐Wolf, K. E., Huang, Y.-C. T., Taylor, D. E., Kantrow, S. P., Carraway, M. S., Crapo, J. D., & Piantadosi, C. A. (1997) · Journal of Applied Physiology · doi:10.1152/jappl.1997.83.2.550 · Cited by 43
“conditions, O2 (2)z in the presence of H2O2 or NO z causes zOH and ONOO2 formation, both of which are strong oxidants and may damage lipids, proteins, or nucleic acids during hyperoxia (18).”
Background
Nitric Oxide: Chemistry, Biosynthesis, and Physiological Role
Hayat, S., Hasan, S. A., Mori, M., Fariduddin, Q., & Ahmad, A. (2009) · Wiley eBooks · doi:10.1002/9783527629138.ch1 · Cited by 43
Novel aminobenzyl-acetamidine derivative modulate the differential regulation of NOSs in LPS induced inflammatory response: Role of PI3K/Akt pathway
Patruno, A., Franceschelli, S., Pesce, M., Maccallini, C., Fantacuzzi, M., Speranza, L., Ferrone, A., Lutiis, M. A. D., Ricciotti, E., Amoroso, R., et al. (2012) · Biochimica et Biophysica Acta (BBA) - General Subjects · doi:10.1016/j.bbagen.2012.08.014 · Cited by 42

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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