Chemical biology of peroxynitrite: Kinetics, diffusion, and radicals
Abstract
Peroxynitrite is formed by the very fast reaction of nitric oxide and superoxide radicals, a reaction that kinetically competes with other routes that chemically consume or physically sequester the reagents. It can behave either as an endogenous cytotoxin toward host tissues or a cytotoxic effector molecule against invading pathogens, depending on the cellular source and pathophysiological setting. Peroxynitrite is in itself very reactive against a few specific targets that range from efficient detoxification systems, such as peroxiredoxins, to reactions eventually leading to enhanced radical formation (e.g., nitrogen dioxide and carbonate radicals), such as the reaction with carbon dioxide. Thus, the chemical biology of peroxynitrite is dictated by the chemical kinetics of its formation and decay and by the diffusion across membranes of the species involved, including peroxynitrite itself. On the other hand, most durable traces of peroxynitrite passing (such as 3-nitrotyrosine) are derived from radicals formed from peroxynitrite by routes that represent extremely low-yield processes but that have potentially critical biological consequences. Here we have reviewed the chemical kinetics of peroxynitrite as a biochemical transient species in order to estimate its rates of formation and decay and then its steady-state concentration in different intra- or extracellular compartments, trying to provide a quantitative basis for its reactivity; additionally, we have considered diffusion across membranes to locate its possible effects. Finally, we have assessed the most successful attempts to intercept peroxynitrite by pharmacological intervention in their potential to increment the existing biological defenses that routinely deal with this cytotoxin.
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Peroxynitrite oxidative processes include direct oxidations and secondary reactions due to nitrogen dioxide, hydroxyl and carbonate radicals.
“These include direct oxidations and secondary reactions due to nitrogen dioxide, hydroxyl and carbonate radicals [120,121].”
From Superoxide Anion Chemistry—Its Role at the Core of the Innate Immunity (2023) · cites this paper as [121]
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Luminescent Chemodosimeters for Bioimaging
Yang, Y., Zhao, Q., Feng, W., & Li, F. (2012) · Chemical Reviews · doi:10.1021/cr2004103 · Cited by 2,236 · see citing works
Cysteine-Mediated Redox Signaling: Chemistry, Biology, and Tools for Discovery
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“Indeed, a fast reaction of ONOO− with CO2 leads to a transient adduct (ONOOCO−2 ) that then undergoes homolysis to carbonate radicals (CO•−3 ) and •NO2 in ∼35% yields (52).”
BackgroundInfluentialProtein oxidation and peroxidation
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Peroxynitrite, a Stealthy Biological Oxidant
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“Indeed, the formation of peroxynitrite occurswith a k1 of 10(10) M 1 s (1), 1 order of magnitude higher than that of enzymatic dismutation ( 1–2 10(9) M 1 s (1)) (2, 13).”
BackgroundInfluentialNox proteins in signal transduction
Brown, D. I., & Griendling, K. (2009) · Free Radical Biology & Medicine · doi:10.1016/j.freeradbiomed.2009.07.023 · Cited by 841 · see citing works
“Superoxide is also capable of reacting with nitric oxide (NO), forming highly reactive and potentially damaging peroxynitrite (OONO−) (rate constant = 4-16 × 109 M−1s−1) [60].”
The role of oxidative stress during inflammatory processes
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“A further oxidative modification of proteins is the addition of a carbonyl group such as ketone or aldehyde groups (carbonylation) to the side chain of amino acids, mainly proline, threonine, lysine, and arginine (DalleDonne et al., 2003).”
BackgroundBiochemistry of Peroxynitrite and Protein Tyrosine Nitration
Ferrer‐Sueta, G., Campolo, N., Trujillo, M., Bartesaghi, S., Carballal, S., Romero, N., Álvarez, B., & Radí, R. (2018) · Chemical Reviews · doi:10.1021/acs.chemrev.7b00568 · Cited by 645 · see citing works
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Basic Principles and Emerging Concepts in the Redox Control of Transcription Factors
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“Thereby, products derived from NO and oxygen with the potential of S-nitrosation, the reactive nitrogen species (RNS) (112), have to be considered as possible signaling molecules, the most likely candidates being the nitroxyl cation NO + and N2O3, whereas the nitroxyl HNO formed according to Eq.”
BackgroundInfluentialMitochondrial peroxiredoxin involvement in antioxidant defence and redox signalling
Cox, A. G., Winterbourn, C. C., & Hampton, M. B. (2009) · Biochemical Journal · doi:10.1042/bj20091541 · Cited by 530 · see citing works
Superoxide Dismutase Mimics: Chemistry, Pharmacology, and Therapeutic Potential
Batinic̈‐Haberle, I., Reboucas, J. S., & Spasojević, I. (2010) · Antioxidants and Redox Signaling · doi:10.1089/ars.2009.2876 · Cited by 531 · see citing works
“Historically, most early synthetic antioxidant compounds were originally developed as SOD mimics, especially because the role of ONOO and its decomposition products in biology were, at the time, neither accepted nor well defined (106).”
Neuroprotective Effect of Antioxidants in the Brain
Lee, K. H., Cha, M., & Lee, B. H. (2020) · International Journal of Molecular Sciences · doi:10.3390/ijms21197152 · Cited by 527 · see citing works
“The superoxide radical anion reacts with nitric oxide (NO) to form the per xynitrite anion (ONOO−) which mediates oxidative modification of protein residues via a interaction with NO.”
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Protein Tyrosine Nitration: Biochemical Mechanisms and Structural Basis of Functional Effects
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Fundamentals on the biochemistry of peroxynitrite and protein tyrosine nitration
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Redox Reactions and Microbial Killing in the Neutrophil Phagosome
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“Generation of NO by neutrophils opens up a rich panoply of chemistry that could be used to kill bacteria (58, 60).”
Niu, H., Liu, J., O’Connor, H. M., Gunnlaugsson, T., James, T. D., & Zhang, H. (2023) · Chemical Society Reviews · doi:10.1039/d1cs01097b · Cited by 454 · see citing works
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Molecular mechanisms underlying chemical liver injury
Gu, X., & Manautou, J. E. (2012) · Expert Reviews in Molecular Medicine · doi:10.1017/s1462399411002110 · Cited by 389 · see citing works
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Redox Signaling by Reactive Electrophiles and Oxidants
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Nitric oxide, antioxidants and prooxidants in plant defence responses
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“The A. thaliana peroxiredoxin IIE (PrxII E) and glutathione peroxidase 5 (Gpx5) of poplar both reduce ONOO− to NO−2 (Figure 3) (Sakamoto et al., 2003; Romero-Puertas et al., 2008; Ferrer-Sueta and Radi, 2009).”
BackgroundSuperoxide Anion Chemistry—Its Role at the Core of the Innate Immunity
Andrés, C. M. C., Pérez de la Lastra, J. M., Andrés Juan, C., Plou, F. J., & Pérez-Lebeña, E. (2023) · International Journal of Molecular Sciences · doi:10.3390/ijms24031841 · Cited by 342 · see citing works
Interplay between oxidant species and energy metabolism
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Connecting the Chemical and Biological Properties of Nitric Oxide
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Molecular Imaging of Peroxynitrite with HKGreen-4 in Live Cells and Tissues
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Reactive Oxygen Species in Chronic Obstructive Pulmonary Disease
Boukhenouna, S., Wilson, M. A., Bahmed, K., & Kośmider, B. (2018) · Oxidative Medicine and Cellular Longevity · doi:10.1155/2018/5730395 · Cited by 259 · see citing works
“Peroxynitrite is a RNS that is involved in many physiological and pathological processes [55, 56].”
BackgroundThe Roles of Neutrophil-Derived Myeloperoxidase (MPO) in Diseases: The New Progress
Lin, W. C., Chen, H., Chen, X., & Guo, C. (2024) · Antioxidants · doi:10.3390/antiox13010132 · Cited by 254 · see citing works
Redox Proteomics: Chemical Principles, Methodological Approaches and Biological/Biomedical Promises
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“These species, mainly represented by nitric oxide (NO) [41–44], superoxide anion radical (O2 ) [45], peroxynitrite anion (ONOO) [46, 47], hydroxyl (OH) [48], lipoperoxide (LOO) [14, 16], hydrogen peroxide (H2O2) [49, 50], and hypochlorous acid (HClO) [51], are highly reactive molecules generated during physiological c…”
BackgroundThe role of catalases in the prevention/promotion of oxidative stress
Gȩbicka, L., & Krych-Madej, J. (2019) · Journal of Inorganic Biochemistry · doi:10.1016/j.jinorgbio.2019.110699 · Cited by 237 · see citing works
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Determination of antiradical and antioxidant activity: basic principles and new insights.
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Selenium Doped Graphene Quantum Dots as an Ultrasensitive Redox Fluorescent Switch
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A Deep Insight into the Sialotranscriptome of the Gulf Coast Tick, Amblyomma maculatum
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“Enzymes dealing with oxidative detoxification are also abundant, some of which, such as selenoproteins, peroxidasins (haem-peroxidases) and superoxide dismutase may actually be secreted and antagonize inflammatory host responses containing superoxide, nitric oxide or peroxinitrite [52,53].”
BackgroundProtein Oxidative Modifications: Beneficial Roles in Disease and Health.
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Zielonka, J., Sikora, A., Joseph, J., & Kalyanaraman, B. (2010) · Journal of Biological Chemistry · doi:10.1074/jbc.m110.110080 · Cited by 223 · see citing works
Reactivity of hydrogen sulfide with peroxynitrite and other oxidants of biological interest
Carballal, S., Trujillo, M., Cuevasanta, E., Bartesaghi, S., Möller, M. N., Folkes, L. K., García-Bereguiain, M. Á., Gutiérrez‐Merino, C., Wardman, P., Denicola, A., et al. (2010) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2010.10.705 · Cited by 219 · see citing works
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Microsensor systems for cell metabolism – from 2D culture to organ-on-chip
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The superoxide radical switch in the biology of nitric oxide and peroxynitrite
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Principles in Redox Signaling: From Chemistry to Functional Significance
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“As previously reported, Prxs very efficiently catalyzes the reduction of peroxynitrous acid in a two-electron process, involving their active site thiolate and leadingtotheformationofnitriteandaproteinsulfenicacid(98, 99).”
Detection and quantification of nitric oxide–derived oxidants in biological systems
Möller, M. N., Ríos, N., Trujillo, M., Radí, R., Denicola, A., & Álvarez, B. (2019) · Journal of Biological Chemistry · doi:10.1074/jbc.rev119.006136 · Cited by 196 · see citing works
“Because of its short life in cells and tissues ( 1 ms) (7), peroxynitrite cannot be detected in biological samples through direct spectroscopic techniques.”
BackgroundInfluentialThe involvement of nitric oxide synthase neurons in enteric neuropathies
Rivera, L. R., Poole, D. P., Thacker, M., & Furness, J. B. (2011) · Neurogastroenterology & Motility · doi:10.1111/j.1365-2982.2011.01780.x · Cited by 184 · see citing works
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An insight into the sialome of blood-feeding Nematocera
Ribeiro, J. M. C., Mans, B. J., & Arcà, B. (2010) · Insect Biochemistry and Molecular Biology · doi:10.1016/j.ibmb.2010.08.002 · Cited by 178 · see citing works
“They may play a housekeeping function, or be related to detoxifying host peroxinitrites (Ferrer-Sueta and Radi, 2009; Trujillo et al., 2007).”
BackgroundAre free radicals involved in thiol-based redox signaling?
Winterbourn, C. C. (2014) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2014.08.017 · Cited by 178 · see citing works
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“Ebselen (Sies and Masumoto, 1997) and Mn-4-TMPyP 5 (Ferrer-Sueta and Radi, 2009) were used as controls since their second order rate constants with PN are well known (Fig.”
BackgroundMethodInfluentialActivity-based fluorescence probes for pathophysiological peroxynitrite fluxes
Mao, Z., Xiong, J., Wang, P., An, J., Zhang, F., Liu, Z., & Kim, J. S. (2021) · Coordination Chemistry Reviews · doi:10.1016/j.ccr.2021.214356 · Cited by 167 · see citing works
Genetically Encoded Fluorescent Probe for the Selective Detection of Peroxynitrite
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Redox Modulation of HMGB1-Related Signaling
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“These roles NO maintains by reacting with metal centers (9), by modulating thiol groups of proteins (forming S -nitrosothiols or/and disulfides) (25, 30), or/and by reacting with superoxide to form peroxynitrite (18, 68, 79).”
Kinetic and mechanistic considerations to assess the biological fate of peroxynitrite
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“Moreover, rate constants in the order of 106 – 107 M−1 s−1 have been reported for the reaction of peroxynitrite with very reactive thiols in proteins, such as those present in peroxiredoxins (Prx), which constitute an efficient key detoxification system of peroxynitrite [21,52,53,54]”
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Design and applications of fluorescent detectors for peroxynitrite
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Liposomal Antioxidants for Protection against Oxidant-Induced Damage
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“superoxide anion favors the production of a strong oxidant, the peroxynitrite anion, which may account for some of the deleterious effects associated with nitric oxide production [31].”
BackgroundThe Incomplete Glutathione Puzzle: Just Guessing at Numbers and Figures?
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“A basal steady-state concentration around 1 nM was also calculated for ONOO- (38, 81).”
BackgroundMethodInfluentialHKGreen-3: A Rhodol-Based Fluorescent Probe for Peroxynitrite
Tao, P., & Yang, D. (2010) · Organic Letters · doi:10.1021/ol102182j · Cited by 152 · see citing works
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“On the other hand, GSH (present at mM concentration in muscles) does not react sufficiently fast in vivo to directly scavenge ONOO•−; instead, glutathione may counteract ONOO•−-dependent processes via reactions with secondary radicals (Ferrer-Sueta & Radi, 2009).”
BackgroundCadet, J., Loft, S. H., Oliński, R., Evans, M. D., Białkowski, K., Wagner, J. R., Dedon, P. C., Möller, P., Greenberg, M. M., & Cooke, M. S. (2012) · Free Radical Research · doi:10.3109/10715762.2012.659248 · Cited by 143 · see citing works
“A likely mechanism of formation of 8-nitroguanine involves the concerted action of O2 and NO2 similar to the mechanism of formation of 3nitrotyrosine [53,57].”
One- and two-electron oxidation of thiols: mechanisms, kinetics and biological fates
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Free radical-mediated systemic immunity in plants
Wendehenne, D., Gao, Q.-M., Kachroo, A., & Kachroo, P. (2014) · Current Opinion in Plant Biology · doi:10.1016/j.pbi.2014.05.012 · Cited by 139 · see citing works
“In animals, ONOO is a powerful toxic reactive nitrogen species behaving as a cytotoxic effector molecule against invading pathogens and in various diseases such as chronic inflammation [38].”
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Blood as a reactive species generator and redox status regulator during exercise
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“Peroxynitrite can form several free radical species including OH, CO3 and NO2 radicals, depending on the pathophysiological microenvironment [9–11].”
A mitochondria-targetable fluorescent probe for peroxynitrite: fast response and high selectivity
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Reactive Oxygen Species: Physiological Roles in the Regulation of Vascular Cells
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Mitochondria‐Targeted Antioxidants: Future Perspectives in Kidney Ischemia Reperfusion Injury
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“About 35% of ONOOCO 2 − is decomposed to NO 2 ∙ and carbonate radical (CO 3 ) [14].”
BackgroundA boronate-based fluorescent probe for the selective detection of cellular peroxynitrite
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Peroxynitrite, a potent macrophage‐derived oxidizing cytotoxin to combat invading pathogens
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“Whenever •NO and superoxide meet each other, they react at diffusion-controlled rate (~1.0 × 1010 M−1s−1, (19)) forming peroxynitrite (ONOO-), a strong oxidant capable of causing oxidation and nitration of both proteins and lipids.”
BackgroundInfluentialThe H+-ATP synthase: A gate to ROS-mediated cell death or cell survival
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“tentially damaging peroxynitrite (OONO\) [58].”
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Optical/electrochemical methods for detecting mitochondrial energy metabolism
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The Diversity of Microbial Responses to Nitric Oxide and Agents of Nitrosative Stress
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“There are numerous excellent reviews on the chemistry, biology, and (patho)physiology of this reaction and ONOO (see, e.g., Pryor and Squadrito, 1995; Beckman and Koppenol, 1996; Ferrer-Sueta and Radi, 2009).”
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Oxidants and Antioxidants in the Redox Biochemistry of Human Red Blood Cells
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Batinic̈‐Haberle, I., Spasojević, I., Tse, H. M., Tovmasyan, A. G., Rajić, Z., Clair, D. K. S., Vujašković, Ž., Dewhirst, M. W., & Piganelli, J. D. (2010) · Amino Acids · doi:10.1007/s00726-010-0603-6 · Cited by 114 · see citing works
“The names of porphyrins are listed in the list of abbreviations 100 I. Batinic-Haberle et al. ability to dismute O 2 •-, making them the most potent synthetic scavengers of peroxynitrite also (Table 1) (Ferrer- Sueta et al. 2003; Ferrer-Sueta and Radi 2009).”
- Authors
- Ferrer-Sueta, G., & Radi, R.
- Affiliations
- Laboratorio de Físicoquímica Biológica, Facultad de Ciencias
- Departamento de Bioquímica
- Venue
- ACS Chemical Biology
- Publisher
- American Chemical Society (ACS)
- Published
- 2009-03-06
- Volume
- 4
- Issue
- 3
- Pages
- 161-177
- ISSN
- 1554-8929 (ISSN-L)
- 1554-8937
- OpenAlex
- W2078672958
- Cited by
- 776
- References
- 133
- Citations by year
- 2026: 29 · 2025: 33 · 2024: 41 · 2023: 45 · 2022: 62 · 2021: 56 · 2020: 39 · 2019: 41 · 2018: 52 · 2017: 48 · 2016: 41 · 2015: 38 · 2014: 39 · 2013: 51 · 2012: 50
- FWCI
- 4.11
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- ACS Chemical Biology (publishedVersion)
- PubMed (publishedVersion)
- Funders
- Howard Hughes Medical Institute
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Redox biology and oxidative stress
- Health Sciences › Medicine › Physiology › Nitric Oxide and Endothelin Effects
- Life Sciences › Immunology and Microbiology › Immunology › Neutrophil, Myeloperoxidase and Oxidative Mechanisms
- Keywords
- peroxynitrite, nitric oxide, superoxide, reaction kinetics, diffusion across membranes, peroxiredoxin, nitrotyrosine, nitroxyl, carbonate radical, nitrogen dioxide radical, radical formation, cytotoxicity, pharmacological interventions, reactive oxygen species
- MeSH terms
- Animals, Antioxidants, Carbon Dioxide, Diffusion, Hemeproteins, Humans, Kinetics, Nitric Oxide, Oxygen, Peroxidases, Superoxides, Nitric Oxide Synthase, Peroxynitrous Acid
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