Peroxynitrite reaction with carbon dioxide/bicarbonate. Kinetics and influence on peroxynitrite-mediated oxidations
Abstract
Peroxynitrite is a strong oxidant produced in vivo as the reaction product of superoxide anion and nitric oxide (k approximately 5 x 10(9) M-1 s-1) and can be formed and mediate reactions in the extracellular environment. It has recently been reported that peroxynitrite and carbon dioxide react in a second-order process (S. V. Lymar and K. Hurst (1995) J. Am. Chem. Soc. 117, 8867-8868). Since one of the most abundant constituents of the extracellular milieu is bicarbonate anion (25 mM in plasma) which is in equilibrium with carbon dioxide (1.3 mM in plasma) we have further studied the kinetics of the reaction between peroxynitrite and carbon dioxide/ bicarbonate and the effect of bicarbonate on different peroxynitrite-mediated oxidations. The apparent second-order rate constant for the reaction is (2.3 +/- 0.1) x 10(3) M-1 s-1 at 37 degrees C and pH 7.4 and a pH-independent second-order rate constant of (5.8 +/- 0.2) x 10(4) M-1 s-1 at 37 degrees C was obtained considering peroxynitrite anion and carbon dioxide as the reacting species. The enthalpy and entropy of activation are delta H* = +10.7 +/- 0.8 kcal mol-1 and delta S* = -6.5 +/- 0.5 cal mol-1 K-1, respectively. The presence of bicarbonate had variable influence on peroxynitrite-mediated oxidations. While bicarbonate significantly enhanced peroxynitrite-mediated nitration of aromatics, it partially inhibited the oxidation of thiols, dimethylsulfoxide, oxyhemoglobin, and cytochrome c+2 and totally inhibited the hydroxylation of benzoate. Spontaneous chemiluminescence studies suggest the formation of bicarbonate radicals during the interactions of peroxynitrite with carbon dioxide/ bicarbonate. Our results support that peroxynitrite anion rapidly reacts with carbon dioxide to yield an adduct (ONOOCO2-) which can participate in oxidation and nitration processes, thus redirecting the primary reactivity of peroxynitrite.
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Mechanisms giving rise to NO2 include exposure to NO2 gas, O2-derived inflammatory by-products ONOOH and nitrosoperoxocarbonate (ONOOCO2), and heme protein-catalyzed oxidation of NO2− to NO2.
“These include exposure to ⅐ NO 2 gas, the O 2 . -derived inflammatory by-products ONOOH and nitrosoperoxocarbonate (ONOOCO 2 ) (45), and heme protein-catalyzed oxidation of NO 2 Ϫ to ⅐ NO 2 (46).”
From Conjugated linoleic acid is a preferential substrate for fatty acid nitration (2012) · cites this paper as [45]
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Self-citation
- Authors
- Denicola, A., Freeman, B. A., Trujillo, M., & Radi, R.
- Affiliations
- Universidad de la República de Uruguay (UY)
- Venue
- Archives of Biochemistry and Biophysics
- Publisher
- Elsevier BV
- Published
- 1996-09
- Volume
- 333
- Issue
- 1
- Pages
- 49-58
- ISSN
- 0003-9861 (ISSN-L)
- OpenAlex
- W2058013605
- Cited by
- 593
- References
- 3
- Citations by year
- 2026: 7 · 2025: 8 · 2024: 12 · 2023: 10 · 2022: 15 · 2021: 9 · 2020: 11 · 2019: 14 · 2018: 9 · 2017: 15 · 2016: 10 · 2015: 19 · 2014: 17 · 2013: 23 · 2012: 19
- FWCI
- 22.92
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Archives of Biochemistry and Biophysics (publishedVersion)
- PubMed (publishedVersion)
- Funders
- National Institutes of Health (5p01hl048676-05)
- National Heart, Lung, and Blood Institute (P01 HL 48676, RDI HL 40458)
- Topics
- Health Sciences › Medicine › Physiology › 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, carbon dioxide, bicarbonate, reaction kinetics, thiol oxidation, cytochrome c oxidation, activation enthalpy and entropy, chemiluminescence
- MeSH terms
- Bicarbonates, Carbon Dioxide, Free Radicals, Kinetics, Luminescent Measurements, Nitrates, Oxidation-Reduction, Thermodynamics, In Vitro Techniques
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