Direct Observation of Intermediates in the Reaction of Peroxynitrite with Carbon Dioxide

Meli, Roger; Nauser, Thomas; Koppenol, Willem H.

doi:10.1002/(sici)1522-2675(19990505)82:5<722::aid-hlca722>3.0.co;2-#

Cited by 70 publications

(62 citation statements)

References 16 publications

(23 reference statements)

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“…The reaction of ONOO − with CO 2 yields the ONOOCO 2 adduct 21,22. It has been proposed that this adduct undergoes either a heterolytic or homolytic cleavage at the weak peroxo O‐O bond to give the strong oxidizing and nitrating species •NO 2 and CO 3 −• radicals, or to give CO 3 2− and NO 2 − ions 65,66. CO 3 −• is a strong one‐electron oxidant that may, itself, inactivate α 1 ‐AP, since it is known to inactivate enzymes, oxidize amino acids, and proteins 67.…”

Section: Discussionmentioning

confidence: 99%

A Reassessment of the Peroxynitrite Scavenging Activity of Uric Acid

Whiteman

Ketsawatsakul

Halliwell

2002

Annals of the New York Academy of Sciences

168

109

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Peroxynitrite is implicated in numerous human diseases. Hence, there is considerable interest in potential therapeutic peroxynitrite scavengers. It has been claimed that uric acid is a powerful peroxynitrite scavenger. We previously observed that uric acid is a powerful inhibitor of tyrosine nitration induced by peroxynitrite, but fails to prevent alpha(1)-antiproteinase (alpha(1)-AP) inactivation induced by peroxynitrite. However, the reactivity of peroxynitrite is significantly modified by bicarbonate and this has not been considered in evaluating the scavenging activity of uric acid and other endogenous antioxidant compounds. In the presence of bicarbonate (25 mM), the ability of uric acid, ascorbate, Trolox, and GSH to inhibit peroxynitrite-mediated tyrosine and guanine nitration is decreased. Protection against peroxynitrite-mediated alpha(1)-AP inactivation is also decreased by ascorbate, Trolox, and GSH, but it is enhanced by uric acid. Bicarbonate also inhibits the ability of these compounds to prevent peroxynitrite-mediated ABTS radical cation formation. However, the abilities of these antioxidants to prevent peroxynitrite-mediated bleaching of pyrogallol red are enhanced by bicarbonate. These results show that physiologic concentrations of bicarbonate substantially modify the ability of uric acid to prevent peroxynitrite-mediated reactions. This study highlights the need to use several different assays in the presence of physiologically relevant concentrations of bicarbonate when assessing compounds for peroxynitrite scavenging, in order to avoid misleading results.

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Section: Discussionmentioning

confidence: 99%

A Reassessment of the Peroxynitrite Scavenging Activity of Uric Acid

Whiteman

Ketsawatsakul

Halliwell

2002

Annals of the New York Academy of Sciences

168

109

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“…Superoxide and NO in a diffusion-controlled reaction yield peroxynitrite which, in biological systems, promptly reacts with carbon dioxide, leading to the formation of carbonate (CO 3 •- ) and nitrogen dioxide (NO 2 •- ) radicals (16, 20, 21, 22). Although there are no direct methods to detect peroxynitrite in vivo , there are reports of certain classes of iron porphyrins which act as peroxynitrite decomposition catalysts (23).…”

Section: Resultsmentioning

confidence: 99%

Site-Specific Carboxypeptidase B1 Tyrosine Nitration and Pathophysiological Implications following Its Physical Association with Nitric Oxide Synthase-3 in Experimental Sepsis

Chatterjee¹,

Lardinois²,

Bhattacharjee³

et al. 2009

The Journal of Immunology

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LPS-induced sepsis results in oxidative modification and inactivation of carboxypeptidase B1 (CPB1). In this study, immunoprecipitated CPB1 was probed for tyrosine nitration using monoclonal nitrotyrosine-specific Abs in a murine model of LPS-induced sepsis. Tyrosine nitration of CPB1 was significantly reduced in the presence of NO synthase (NOS) inhibitors and the xanthine oxidase (XO) inhibitor allopurinol and in NOS-3 knockout (KO) mice. CPB1 tyrosine nitration and loss of activity by the concerted action of NOS-3 and XO were also confirmed in vitro using both the NO donor 3-morpholinosydnonimine and peroxynitrite. Liquid chromatography/tandem mass spectrometry data indicated five sites of tyrosine nitration in vitro including Tyr248, the tyrosine at the catalytic site. The site- and protein-specific nitration of CPB1 and the possible high nitration yield to inactivate it were elucidated by confocal microscopy. The studies indicated that CPB1 colocalized with NOS-3 in the cytosol of sinus-lining cells in the red pulp of the spleen. Further analysis of CPB1-immunoprecipitated samples indicated immunoreactivity to a monoclonal NOS-3 Ab, suggesting protein complex formation with CPB1. XO and NOS inhibitors and NOS-3 KO mice injected with LPS had decreased levels of C5a in spleens of septic mice, indicating peroxynitrite as a possible cause for CPB1 functional alteration. Thus, CPB1 colocalization, coupling, and proximity to NOS-3 in the sinus-lining cells of spleen red pulp could explain the site-specific tyrosine nitration and inactivation of CPB1. These results open up new avenues for the investigation of several enzymes involved in inflammation and their site-specific oxidative modifications by protein-protein interactions as well as their role in sepsis.

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“…2 . In later years, studies were conducted for the reaction between ONOO − and CO 2 , and the reaction mechanism can be presented by Equations (5.39) The formation of the carbonate radical was directly detected using EPR [37,188]. Now decades later, this reaction was recognized that the bicarbonate buffer inhibits Escherichia coli killing by peroxynitrite [183,184].…”

Section: Decomposition In Aqueous Solutionmentioning

confidence: 99%

“…The reaction between peroxynitrite and CO 2 was observed almost four decades ago when peroxynitrite was determined to be unstable in carbonate buffered solution [182]. Both mixtures of peroxynitrite and bicarbonate at pH 6-9 and peroxynitrite and CO 2 -saturated solution in alkaline media yielded carbonated radicals ranging from a few percent [188] to 35% [37]. In later years, studies were conducted for the reaction between ONOO − and CO 2 , and the reaction mechanism can be presented by Equations (5.39) The formation of the carbonate radical was directly detected using EPR [37,188].…”

Section: Decomposition In Aqueous Solutionmentioning

confidence: 99%

Reactive Inorganic Oxy‐Species of C, N, S, and P

Sharma¹

2012

Oxidation of Amino Acids, Peptides, and Proteins

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Direct Observation of Intermediates in the Reaction of Peroxynitrite with Carbon Dioxide

Cited by 70 publications

References 16 publications

A Reassessment of the Peroxynitrite Scavenging Activity of Uric Acid

A Reassessment of the Peroxynitrite Scavenging Activity of Uric Acid

Site-Specific Carboxypeptidase B1 Tyrosine Nitration and Pathophysiological Implications following Its Physical Association with Nitric Oxide Synthase-3 in Experimental Sepsis

Reactive Inorganic Oxy‐Species of C, N, S, and P

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