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Cited by 1,338

The DOI matches its Crossref record; 2 of the 2 references it cites were found in a registry or an index.

Peroxynitrite, a cloaked oxidant formed by nitric oxide and superoxide

Koppenol, W. H., Moreno, J. J., Pryor, William A., Ischiropoulos, H., Beckman, J. S.·1992·Chemical Research in Toxicology
DOI 10.1021/tx00030a017
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Abstract

Peroxynitrite [oxoperoxonitrate(1-), ONOO-] may be formed in vivo from superoxide and nitric oxide. The anion is stable, but the acid (pKa = 6.8) decays to nitrate with a rate of 1.3 s-1 at 25 degrees C. The experimental activation parameters of this process are delta H++ = +18 +/- 1 kcal/mol, delta S++ = +3 +/- 2 cal/(mol.K), and delta G++ = +17 +/- 1 kcal/mol. Peroxynitrite (or its protonated form) oxidizes some compounds such as thiols and thioethers in a biomolecular reaction. The reactions with glutathione and cysteine have activation enthalpies of 10.9 and 9.7 kcal/mol, respectively, which are lower than that of the isomerization reaction. Peroxynitrite reacts with other compounds such as dimethyl sulfoxide and deoxyribose in a unimolecular reaction for which the activation of peroxynitrite is rate-limiting. In theory, activation could involve (1) heterolysis to OH- and NO2+ (delta rxn Gzero' = 13 kcal/mol at pH 7) or (2) homolysis to .OH and .NO2 (delta rxn Gzero = 21 kcal/mol), and these processes also could be involved in the isomerization to nitrate. However, thermodynamic and kinetic considerations indicate that neither process is feasible, although binding to metal ions may reduce the large activation energy associated with heterolysis. An intermediate closely related to the transition state for isomerization of ONOOH to HONO2 may be the strongly oxidizing intermediate responsible for hydroxyl radical-like oxidations mediated by ONOOH. Thus, peroxynitrite reacts with different compounds by at least two distinct mechanisms, and the hydroxyl radical is not involved in either.

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Metadata

Authors
Koppenol, W. H., Moreno, J. J., Pryor, W. A., Ischiropoulos, H., & Beckman, J. S.
Venue
Chemical Research in Toxicology
Publisher
American Chemical Society (ACS)
Published
1992-11
Volume
5
Issue
6
Pages
834-842
ISSN
  • 0893-228X (ISSN-L)
  • 1520-5010
DOI
10.1021/tx00030a017
OpenAlex
W2022377100
Cited by
1,338
References
2
FWCI
15.40
Type
journal article
Language
en
Open access
closed

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