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Peroxynitrite

From Wikipedia, the free encyclopedia
Ion
Peroxynitrite
Chemical structure of the peroxynitrite anion
Names
IUPAC name
Oxido nitrite
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
674445
KEGG
UNII
  • InChI=1S/HNO3/c2-1-4-3/h3H/p-1
    Key: CMFNMSMUKZHDEY-UHFFFAOYSA-M
  • N(=O)O[O-]
Properties
NO3−
Molar mass62.005 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Reactions of peroxynitrite leading to either apoptotic or necrotic cell death

Peroxynitrite (sometimes calledperoxonitrite) is anion with the formula ONOO−. It is astructural isomer ofnitrate,NO−
3. Peroxynitrite is a potentreactive nitrogen species and is highlycytotoxic.[1]

Preparation

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Peroxynitrite can be prepared by the reaction ofsuperoxide withnitric oxide:[2][3][4]

NO + O−2 → NO(O2)−

It is prepared by the reaction ofhydrogen peroxide withnitrite:[5]

H2O2 +NO−
2 → ONOO− + H2O

Its presence is indicated by theabsorbance at 302 nm (pH 12,ε302 = 1670 M−1 cm−1).

Reactions

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Peroxynitrite is weakly basic with apKa of ~6.8.

It is reactive towardDNA andproteins.

ONOO− reactsnucleophilically withcarbon dioxide.[6]In vivo, the concentration of carbon dioxide is about 1 mM, and its reaction with ONOO− occurs quickly. Thus, under physiological conditions, the reaction of ONOO− with carbon dioxide to formnitrosoperoxycarbonate (ONOOCO−
2) is by far the predominant pathway for ONOO−.ONOOCO−
2 homolyzes to form carbonate radical and nitrogen dioxide, again as a pair ofcaged radicals. Approximately 66% of the time, these two radicals recombine to form carbon dioxide and nitrate. The other 33% of the time, these two radicals escape the solvent cage and become free radicals. It is these radicals (carbonate radical andnitrogen dioxide) that are believed to cause peroxynitrite-related cellular damage.

Peroxynitrous acid

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Main article:Peroxynitrous acid

Itsconjugate acidperoxynitrous acid is highly reactive, although peroxynitrite is stable in basic solutions.[7][8]

See also

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References

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  1. ^Szabó, Csaba; Ischiropoulos, Harry; Radi, Rafael (August 2007)."Peroxynitrite: biochemistry, pathophysiology and development of therapeutics".Nature Reviews Drug Discovery.6 (8):662–680.doi:10.1038/nrd2222.ISSN 1474-1784.
  2. ^Bohle, D. Scott; Sagan, Elisabeth S. (2004). "Main Group Compounds".Tetramethylammonium Salts of Superoxide and Peroxynitrite. Inorganic Syntheses. Vol. 34. p. 36.doi:10.1002/0471653683.ch1.ISBN 978-0-471-64750-8.
  3. ^Pacher, P; Beckman, J. S; Liaudet, L (2007)."Nitric oxide and peroxynitrite in health and disease".Physiological Reviews.87 (1):315–424.doi:10.1152/physrev.00029.2006.PMC 2248324.PMID 17237348.
  4. ^Szabó, C; Ischiropoulos, H; Radi, R (2007). "Peroxynitrite: Biochemistry, pathophysiology and development of therapeutics".Nature Reviews Drug Discovery.6 (8):662–80.doi:10.1038/nrd2222.PMID 17667957.
  5. ^Beckman, J. S; Koppenol, W. H (1996). "Nitric oxide, superoxide, and peroxynitrite: The good, the bad, and ugly".American Journal of Physiology. Cell Physiology.271 (5 Pt 1): C1424–37.doi:10.1152/ajpcell.1996.271.5.C1424.PMID 8944624.
  6. ^Denicola, Ana; Freeman, Bruce A.; Trujillo, Madia; Radi, Rafael (1996-09-01)."Peroxynitrite Reaction with Carbon Dioxide/Bicarbonate: Kinetics and Influence on Peroxynitrite-Mediated Oxidations".Archives of Biochemistry and Biophysics.333 (1):49–58.doi:10.1006/abbi.1996.0363.ISSN 0003-9861.
  7. ^Holleman, A. F.; Wiberg, E.Inorganic Chemistry Academic Press: San Diego, 2001.ISBN 0-12-352651-5.
  8. ^Koppenol, W. H (1998)."The chemistry of peroxynitrite, a biological toxin".Química Nova.21 (3):326–331.doi:10.1590/S0100-40421998000300014.
Nitrogen species
Hydrides
Organic
Oxides
Halides
Oxidation states
−3,−2,−1, 0,+1,+2,+3,+4,+5 (a stronglyacidic oxide)
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