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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Sphingosine-1-Phosphate Attenuates Lung Injury Induced by Intestinal Ischemia/Reperfusion in Mice: Role of Inducible Nitric-Oxide Synthase
Ding, R., Han, J., Tian, Y., Guo, R.-X., & Ma, X. (2011) · Inflammation · doi:10.1007/s10753-011-9301-0 · Cited by 29
“It has been suggested that the superoxide ions react with NO to produce peroxynitrite, which then causes accentuated lipid peroxidation, and proteic and DNA modifications resulting in cellular damages [42].”
Background
Protective effect of tryptophan against dextran sulfate sodium- induced experimental colitis
Shizuma, T., Mori, H., & Fukuyama, N. (2013) · The Turkish Journal of Gastroenterology · doi:10.4318/tjg.2013.0558 · Cited by 29
“Moreover, superoxide reacts rapidly to NO and induces the generation of peroxynitrite which is a strong cytotoxic, leading to severe tissue damage (8,9).”
Background
Simultaneous analysis and peroxynitrite-scavenging activity of galloylated flavonoid glycosides and ellagic acid in Euphorbia supina
Nugroho, A., Rhim, T.-J., Choi, M.-Y., Choi, J. S., Kim, Y., Kim, M., & Park, H.-J. (2013) · Archives of Pharmacal Research · doi:10.1007/s12272-013-0307-z · Cited by 29
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Kobayashi, S., Hamashima, S., Homma, T., Sato, M., Kusumi, R., Bannai, S., Fujii, J., & Sato, H. (2018) · Nitric Oxide · doi:10.1016/j.niox.2018.05.005 · Cited by 30
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“Both •OONO and O2NOO modify tyrosine in proteins to create nitrotyrosines, leaving a footprint detectable in vivo [38, 41, 42].”
Background
Effects of melatonin and caffeic acid phenethyl ester on testicular injury induced by myocardial ischemia/reperfusion in rats
Eşrefoğlu, M., Gül, M., Parlakpınar, H., & Acet, A. (2005) · Fundamental and Clinical Pharmacology · doi:10.1111/j.1472-8206.2005.00331.x · Cited by 29
Effects of acute hypobaric hypoxia on the nitric oxide system of the rat cerebral cortex: Protective role of nitric oxide inhibitors
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Cobalt and chromium ions induce nitration of proteins in human U937 macrophages in vitro
Petit, A., Mwale, F., Tkaczyk, C., Antoniou, J., Zukor, D. J., & Huk, O. L. (2006) · Journal of Biomedical Materials Research Part A · doi:10.1002/jbm.a.30884 · Cited by 29
Angiotensin II and oxidized LDL: an unholy alliance creating oxidative stress
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In vitro studies of interactions of NO· donor drugs with superoxide and hydroxyl radicals
Dalloz, F., Maupoil, V., Lecour, S., Briot, F., & Rochette, L. (1997) · Molecular and Cellular Biochemistry · doi:10.1023/a:1006821724773 · Cited by 29
“Under physiological conditions approximately 20% of the peroxynitrite anions are protonated [48, 49].”
Background
Effect of antioxidant treatments on nitrate tolerance development in normotensive and hypertensive rats
Cabassi, A., Bouchard, J., Dumont, É. C., Girouard, H., Jossec, M. L., Lamontagne, D., Besner, J., & de Champlain, J. (2000) · Journal of Hypertension · doi:10.1097/00004872-200018020-00009 · Cited by 29
Free Radical Mediated Oxidation of Proteins
Stadtman, E. R. (1998) · Springer eBooks · doi:10.1007/978-1-4757-2907-8_5 · Cited by 30
Fas receptor-deficient lpr mice are protected against acetaminophen hepatotoxicity due to higher glutathione synthesis and enhanced detoxification of oxidant stress
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“…in lpr mice correlates with decreased peroxynitrite formation One of the most powerful oxidants in vivo is peroxynitrite, which can be formed when superoxide generated from mitochondrial dysfunction reacts with nitric oxide produced in part by nitric oxide synthases (Pryor and Squadrito, 1995).”
Background
Amelioration of elastase‐induced lung emphysema and reversal of pulmonary hypertension by pharmacological iNOS inhibition in mice
Fysikopoulos, A., Seimetz, M., Hadžić, S., Knoepp, F., Wu, C., Malkmus, K., Wilhelm, J., Pichl, A., Bednorz, M., Roxlau, E. T., et al. (2020) · British Journal of Pharmacology · doi:10.1111/bph.15057 · Cited by 28
Gas‐phase peroxynitrite generation using dielectric barrier discharge at atmospheric pressure: A prospective sterilizer
Liu, K., Duan, Q., Zheng, Z., Zhou, R., Zhou, R., Tang, W., Cullen, P. J., & Ostrikov, K. (2021) · Plasma Processes and Polymers · doi:10.1002/ppap.202100016 · Cited by 28
Studies on peroxynitrite-modified H1 histone: Implications in systemic lupus erythematosus
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Direct contribution of inducible nitric oxide synthase expression to apoptosis induction in primary smooth chorion trophoblast cells of human fetal membrane tissues
Yuan, B., Ohyama, K., Takeichi, M., & Toyoda, H. (2008) · The International Journal of Biochemistry & Cell Biology · doi:10.1016/j.biocel.2008.09.031 · Cited by 28
“…Li et l., 2001; Kwak et al., 2006; Xu et al., 2006; Taylor et al., 2007) hat apoptosis induction was mediated through p38 MAPK activaion by NO itself or peroxynitrite (ONOO–), a potent oxidant which s formed by the interaction of NO with superoxide (Radi et al., 991; Pryor and Squadrito, 1995).”
Background
Phosphodiesterase inhibition induces retinal degeneration, oxidative stress and inflammation in cone-enriched cultures of porcine retina
de la Cámara, C. M.-F., Sequedo, M. D., Gómez‐Pinedo, U., Jaijo, T., Aller, E., García-Tárraga, P., García‐Verdugo, J. M., Millán, J. M., & Rodrigo, R. (2013) · Experimental Eye Research · doi:10.1016/j.exer.2013.03.015 · Cited by 28
Nitric Oxide Donors Stimulate Bile Flow and Glutathione Disulfide Excretion Independent of Guanosine 3′,5′–Cyclic Monophosphate in the Isolated Perfused Rat Liver
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“The radical peroxynitrite then significantly augments the lipid peroxidation together with the structural modifications in proteins and DNA, thus leading to the cellular damage [50,51].”
Background
The effect of reactive oxygen species on whole blood aggregation and the endothelial cell-platelet interaction in patients with coronary heart disease
Watt, J., Ewart, M., Greig, F. H., Oldroyd, K. G., Wadsworth, R. M., & Kennedy, S. (2012) · Thrombosis Research · doi:10.1016/j.thromres.2012.03.024 · Cited by 27
“Additionally, although resting platelets do not produce NO, this is formed following stimulation with platelet agonists [16] and can react with O2 to produce ONOO [17].”
Background
Mechanisms and Biological Consequences of Peroxynitrite-Dependent Protein Oxidation and Nitration
Trujillo, M., Álvarez, B., Souza, J. M., Romero, N., Castro, L., Thomson, L., & Radí, R. (2010) · Elsevier eBooks · doi:10.1016/b978-0-12-373866-0.00003-4 · Cited by 29
“8 (Goldstein and Czapski, 1995b; Kissner et al., 1997; Pryor and Squadrito, 1995), peroxynitrite predominates as the anion at physiological pH, and hence its diffusion through membranes is limited.”
BackgroundInfluential
Reactive Oxygen Species, Oxidative Stress and Plant Ion Channels
Demidchik, V. V. (2010) · Signaling and communication in plants · doi:10.1007/978-3-642-10494-7_11 · Cited by 30
The decomposition of peroxynitrite does not yield nitroxyl anion and singlet oxygen
Merényi, G., Lind, J., Czapski, G., & Goldstein, S. (2000) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.150238197 · Cited by 28
Biological Reactions of Peroxynitrite: Evidence for an Alternative Pathway of Salicylate Hydroxylation
Narayan, M., Berliner, L. J., Merola, A. J., Diaz, P. T., & Clanton, T. L. (1997) · Free Radical Research · doi:10.3109/10715769709097839 · Cited by 28
Effect of Methylguanidine in a Model of Septic Shock Induced by LPS
Marzocco, S., Paola, R. D., Ribecco, M. T. S., Sorrentino, R., Britti, D., Massimini, G., Pinto, A., Autore, G., & Cuzzocrea, S. (2004) · Free Radical Research · doi:10.1080/10715760410001725517 · Cited by 27
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“It is possible that by combining with superoxide anion, NO may act as a sink to reduce the contribution of IRI generated superoxide to excessive free radical chain reaction propagation [92, 93].”
Background
Melatonin reduces protein and lipid oxidative damage induced by homocysteine in rat brain homogenates
Ortega‐Gutiérrez, S., Fuentes‐Broto, L., García, J. J., López‐Vicente, M., Martínez‐Ballarín, E., Mena, F. J. M., Millán‐Plano, S., & Reiter, R. J. (2007) · Journal of Cellular Biochemistry · doi:10.1002/jcb.21327 · Cited by 27
Fe(III) mineral reduction followed by partial dissolution and reactive oxygen species generation during 2,4,6-trinitrotoluene transformation by the aerobic yeast Yarrowia lipolytica
Ziganshin, A. M., Ziganshina, E. E., Byrne, J. M., Gerlach, R., Struve, E., Biktagirov, T., Rodionov, A., & Kappler, A. A. (2015) · AMB Express · doi:10.1186/s13568-014-0094-z · Cited by 26
“Peroxynitrite is not stable under acidic conditions resulting in rearrangement to nitrate (Pryor and Squadrito 1995; Pfeiffer et al. 1997).”
Background
Studies on pig blood platelet responses to peroxynitrite action
Nowak, P. (2001) · Platelets · doi:10.1080/09537100120068161 · Cited by 27
“1 M NaOH ( « 302 nm = 1679 M –1 cm 1 ).(16) Some experiments were also performed with decomposed ONOO, which was prepared by allowing the ONOO to decompose at neutral pH in phosphate-buffered saline (60 min).”
Method
Ringer’s Ethyl Pyruvate Solution: A Novel Resuscitation Fluid for the Treatment of Hemorrhagic Shock and Sepsis
Fink, M. P. (2003) · The Journal of Trauma: Injury, Infection, and Critical Care · doi:10.1097/01.ta.0000064522.75563.00 · Cited by 27
Contribution of peroxynitrite to fatal cardiovascular depression induced by overproduction of nitric oxide in rostral ventrolateral medulla of the rat
Chan, S. H. H., Wang, L. L., Ou, C.-C., & Chan, J. Y. H. (2002) · Neuropharmacology · doi:10.1016/s0028-3908(02)00146-6 · Cited by 27
The expression of nNOS, iNOS and nitrotyrosine is increased in the rat cerebral cortex in experimental hepatic encephalopathy
Suárez, I., Bodega, G., Arilla, E., Felipo, V., & Fernández, B. (2006) · Neuropathology and Applied Neurobiology · doi:10.1111/j.1365-2990.2006.00768.x · Cited by 27
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Shustov, G. V., Spinney, R., & Rauk, A. (2000) · Journal of the American Chemical Society · doi:10.1021/ja993533k · Cited by 27
Inhibition of the yeast metal reductase heme protein fre1 by nitric oxide (NO): a model for inhibition of NADPH oxidase by NO
Shinyashiki, M., Pan, C. G., Lopez, B., & Fukuto, J. M. (2004) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2004.05.031 · Cited by 27

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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