Literature DB >> 23872352

Kinetic and mechanistic considerations to assess the biological fate of peroxynitrite.

Sebastián Carballal1, Silvina Bartesaghi, Rafael Radi.   

Abstract

BACKGROUND: Peroxynitrite, the product of the reaction between superoxide radicals and nitric oxide, is an elusive oxidant with a short half-life and a low steady-state concentration in biological systems; it promotes nitroxidative damage. SCOPE OF REVIEW: We will consider kinetic and mechanistic aspects that allow rationalizing the biological fate of peroxynitrite from data obtained by a combination of methods that include fast kinetic techniques, electron paramagnetic resonance and kinetic simulations. In addition, we provide a quantitative analysis of peroxynitrite production rates and conceivable steady-state levels in living systems. MAJOR
CONCLUSIONS: The preferential reactions of peroxynitrite in vivo include those with carbon dioxide, thiols and metalloproteins; its homolysis represents only <1% of its fate. To note, carbon dioxide accounts for a significant fraction of peroxynitrite consumption leading to the formation of strong one-electron oxidants, carbonate radicals and nitrogen dioxide. On the other hand, peroxynitrite is rapidly reduced by peroxiredoxins, which represent efficient thiol-based peroxynitrite detoxification systems. Glutathione, present at mM concentration in cells and frequently considered a direct scavenger of peroxynitrite, does not react sufficiently fast with it in vivo; glutathione mainly inhibits peroxynitrite-dependent processes by reactions with secondary radicals. The detection of protein 3-nitrotyrosine, a molecular footprint, can demonstrate peroxynitrite formation in vivo. Basal peroxynitrite formation rates in cells can be estimated in the order of 0.1 to 0.5μMs(-1) and its steady-state concentration at ~1nM. GENERAL SIGNIFICANCE: The analysis provides a handle to predict the preferential fate and steady-state levels of peroxynitrite in living systems. This is useful to understand pathophysiological aspects and pharmacological prospects connected to peroxynitrite. This article is part of a Special Issue entitled Current methods to study reactive oxygen species - pros and cons and biophysics of membrane proteins. Guest Editor: Christine Winterbourn.
© 2013.

Entities:  

Keywords:  2,2′-azinobis (3-ethylbenzthiazoline-6-sulfonic acid); 3-nitrotyrosine; 5,5-dimethyl-1-pyrroline-N-oxide; ABTS(2−); DMPO; DTPA; EPO; Free radical; GSH; MPO; NOS; NT; Nitric oxide; Nitrotyrosine; Oxidative stress; Peroxynitrite; Prx; SOD; Superoxide radical; diethylenetriaminepentaacetic acid; eosinophil peroxidase; glutathione; myeloperoxidase; nitric oxide synthase; peroxiredoxin; superoxide dismutase

Mesh:

Substances:

Year:  2013        PMID: 23872352      PMCID: PMC3858447          DOI: 10.1016/j.bbagen.2013.07.005

Source DB:  PubMed          Journal:  Biochim Biophys Acta        ISSN: 0006-3002


  151 in total

1.  Reactions of manganese porphyrins and manganese-superoxide dismutase with peroxynitrite.

Authors:  Gerardo Ferrer-Sueta; Celia Quijano; Beatriz Alvarez; Rafael Radi
Journal:  Methods Enzymol       Date:  2002       Impact factor: 1.600

2.  Oxidative and nitrosative stress in acute renal ischemia.

Authors:  E Noiri; A Nakao; K Uchida; H Tsukahara; M Ohno; T Fujita; S Brodsky; M S Goligorsky
Journal:  Am J Physiol Renal Physiol       Date:  2001-11

3.  Direct EPR detection of the carbonate radical anion produced from peroxynitrite and carbon dioxide.

Authors:  M G Bonini; R Radi; G Ferrer-Sueta; A M Ferreira; O Augusto
Journal:  J Biol Chem       Date:  1999-04-16       Impact factor: 5.157

4.  Diffusion of peroxynitrite in the presence of carbon dioxide.

Authors:  N Romero; A Denicola; J M Souza; R Radi
Journal:  Arch Biochem Biophys       Date:  1999-08-01       Impact factor: 4.013

5.  Uric acid oxidation by peroxynitrite: multiple reactions, free radical formation, and amplification of lipid oxidation.

Authors:  C X Santos; E I Anjos; O Augusto
Journal:  Arch Biochem Biophys       Date:  1999-12-15       Impact factor: 4.013

6.  Distance-dependent diffusion-controlled reaction of •NO and O2•- at chemical equilibrium with ONOO-.

Authors:  Horacio Botti; Matías N Möller; Daniel Steinmann; Thomas Nauser; Willem H Koppenol; Ana Denicola; Rafael Radi
Journal:  J Phys Chem B       Date:  2010-11-10       Impact factor: 2.991

7.  Kinetic analysis of intracellular concentrations of reactive nitrogen species.

Authors:  Chang Hoon Lim; Peter C Dedon; William M Deen
Journal:  Chem Res Toxicol       Date:  2008-11       Impact factor: 3.739

8.  The reaction of no with superoxide.

Authors:  R E Huie; S Padmaja
Journal:  Free Radic Res Commun       Date:  1993

9.  Multiple thioredoxin-mediated routes to detoxify hydroperoxides in Mycobacterium tuberculosis.

Authors:  Timo Jaeger; Heike Budde; Leopold Flohé; Ulrich Menge; Mahavir Singh; Madia Trujillo; Rafael Radi
Journal:  Arch Biochem Biophys       Date:  2004-03-01       Impact factor: 4.013

10.  Requirements for superoxide-dependent tyrosine hydroperoxide formation in peptides.

Authors:  Christine C Winterbourn; Helena N Parsons-Mair; Silvia Gebicki; Janusz M Gebicki; Michael J Davies
Journal:  Biochem J       Date:  2004-07-01       Impact factor: 3.857

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  39 in total

Review 1.  Tyrosine-Nitrated Proteins: Proteomic and Bioanalytical Aspects.

Authors:  Carlos Batthyány; Silvina Bartesaghi; Mauricio Mastrogiovanni; Analía Lima; Verónica Demicheli; Rafael Radi
Journal:  Antioxid Redox Signal       Date:  2016-07-22       Impact factor: 8.401

2.  Structural and molecular basis of the peroxynitrite-mediated nitration and inactivation of Trypanosoma cruzi iron-superoxide dismutases (Fe-SODs) A and B: disparate susceptibilities due to the repair of Tyr35 radical by Cys83 in Fe-SODB through intramolecular electron transfer.

Authors:  Alejandra Martinez; Gonzalo Peluffo; Ariel A Petruk; Martín Hugo; Dolores Piñeyro; Verónica Demicheli; Diego M Moreno; Analía Lima; Carlos Batthyány; Rosario Durán; Carlos Robello; Marcelo A Martí; Nicole Larrieux; Alejandro Buschiazzo; Madia Trujillo; Rafael Radi; Lucía Piacenza
Journal:  J Biol Chem       Date:  2014-03-10       Impact factor: 5.157

3.  Imaging Approaches to Assessments of Toxicological Oxidative Stress Using Genetically-encoded Fluorogenic Sensors.

Authors:  Elizabeth M Corteselli; James M Samet; Eugene A Gibbs-Flournoy
Journal:  J Vis Exp       Date:  2018-02-07       Impact factor: 1.355

4.  Kinetics of Nitrite Reduction and Peroxynitrite Formation by Ferrous Heme in Human Cystathionine β-Synthase.

Authors:  Sebastián Carballal; Ernesto Cuevasanta; Pramod K Yadav; Carmen Gherasim; David P Ballou; Beatriz Alvarez; Ruma Banerjee
Journal:  J Biol Chem       Date:  2016-02-11       Impact factor: 5.157

Review 5.  Peroxynitrite, a potent macrophage-derived oxidizing cytotoxin to combat invading pathogens.

Authors:  Carolina Prolo; María Noel Alvarez; Rafael Radi
Journal:  Biofactors       Date:  2013-11-26       Impact factor: 6.113

6.  A tandem activity-based sensing and labeling strategy enables imaging of transcellular hydrogen peroxide signaling.

Authors:  Hidefumi Iwashita; Erika Castillo; Marco S Messina; Raymond A Swanson; Christopher J Chang
Journal:  Proc Natl Acad Sci U S A       Date:  2021-03-02       Impact factor: 11.205

Review 7.  Redox Signaling by Reactive Electrophiles and Oxidants.

Authors:  Saba Parvez; Marcus J C Long; Jesse R Poganik; Yimon Aye
Journal:  Chem Rev       Date:  2018-08-27       Impact factor: 60.622

Review 8.  Live-cell imaging approaches for the investigation of xenobiotic-induced oxidant stress.

Authors:  Phillip A Wages; Wan-Yun Cheng; Eugene Gibbs-Flournoy; James M Samet
Journal:  Biochim Biophys Acta       Date:  2016-05-18

Review 9.  Leveraging oxidative stress questions in vivo: Implications and limitations.

Authors:  Gavin E Arteel
Journal:  Arch Biochem Biophys       Date:  2016-04-01       Impact factor: 4.013

10.  8-Aminoguanosine and 8-Aminoguanine Exert Diuretic, Natriuretic, Glucosuric, and Antihypertensive Activity.

Authors:  Edwin K Jackson; Delbert G Gillespie; Zaichuan Mi
Journal:  J Pharmacol Exp Ther       Date:  2016-09-27       Impact factor: 4.030

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