Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/10/02 09:32:45」(JST)

wiki en

The structure of the peroxynitrite anion

Reactions of peroxynitrite leading to either apoptotic or necrotic cell death

Peroxynitrite (sometimes called peroxonitrite) is an anion with the formula ONOO⁻. It is an unstable structural isomer of nitrate, NO₃⁻. Although its conjugate acid is highly reactive, peroxynitrite is stable in basic solutions.^[1]^[2] It is prepared by the reaction of hydrogen peroxide with nitrite:

H₂O₂ + NO₂⁻ → ONOO⁻ + H₂O

Peroxynitrite is an oxidant and nitrating agent. Because of its oxidizing properties, peroxynitrite can damage a wide array of molecules in cells, including DNA and proteins. Formation of peroxynitrite in vivo has been ascribed to the reaction of the free radical superoxide with the free radical nitric oxide:^[3]^[4]

·O₂⁻ + ·NO → ONO₂⁻

The resultant pairing of these two free radicals results in peroxynitrite, a molecule that is itself not a free radical, but that is a powerful oxidant.

In the laboratory, a solution of peroxynitrite can be prepared by treating acidified hydrogen peroxide with a solution of sodium nitrite, followed by rapid addition of NaOH. Its concentration is indicated by the absorbance at 302 nm (pH 12, ε₃₀₂ = 1670 M⁻¹ cm⁻¹).^[5]

As a nucleophile

ONOO⁻ reacts nucleophilically with carbon dioxide. 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 form nitrosoperoxycarbonate (ONOOCO₂⁻) is by far the predominant pathway for ONOO⁻. ONOOCO₂⁻ homolyzes to form carbonate radical and nitrogen dioxide, again as a pair of caged 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 and nitrogen dioxide) that are believed to cause peroxynitrite-related cellular damage.

Peroxynitrous acid

References

^ Holleman, A. F.; Wiberg, E. "Inorganic Chemistry" Academic Press: San Diego, 2001. ISBN 0-12-352651-5.
^ W. H. Koppenol
^ Pacher, P.; Beckman, J. S.; Liaudet, L.; "Nitric Oxide and Peroxynitrite: in Health and disease" Physiological Reviews 2007, volume 87(1), page 315-424. doi:10.1152/physrev.00029.2006 PMID 17237348
^ Csaba Szabó, Harry Ischiropoulos and Rafael Radi; Peroxynitrite: biochemistry,pathophysiology and development of therapeutics Nature Reviews Drug Discovery; 6, 662-680 (August 2007)
^ Beckman, J. S.; Koppenol, W. H. "Nitric Oxide, Superoxide, and Peroxynitrite: the Good, the Bad, and Ugly" American Journal of Physiology- Cell Physiology 1996, volume 271, page C1424-C1437.

UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

1. 一酸化窒素と腎臓 nitric oxide and the kidney
2. 細菌性髄膜炎の病因および病態生理 pathogenesis and pathophysiology of bacterial meningitis
3. 心不全における酸化ストレスの役割 role of oxidative stress in heart failure
4. 冠動脈内皮細胞機能不全：基本概念 coronary artery endothelial dysfunction basic concepts
5. 虚血性脳卒中の病態生理 pathophysiology of ischemic stroke

English Journal

Peroxiredoxin distribution in the mouse brain with emphasis on neuronal populations affected in neurodegenerative disorders.

Goemaere J, Knoops B.SourceLaboratory of Cell Biology, Institut des Sciences de la Vie (ISV), Université catholique de Louvain, 1348 Louvain-la-Neuve, Belgium.
The Journal of comparative neurology.J Comp Neurol.2012 Feb 1;520(2):258-80. doi: 10.1002/cne.22689.
Redox changes are observed in neurodegenerative diseases, ranging from increased levels of reactive oxygen/nitrogen species and disturbance of antioxidant systems, to nitro-oxidative damage. By reducing hydrogen peroxide, peroxynitrite, and organic hydroperoxides, peroxiredoxins (Prdxs) represent a
PMID 21674491

Chemiluminometric evaluation of melatonin and selected melatonin precursors' interaction with reactive oxygen and nitrogen species.

Harasimowicz J, Marques KL, Silva AF, Costa RC, Prior JA, Rodrigues SS, Santos JL.SourceREQUIMTE, Department of Chemical Sciences, Porto University, 4099-030 Porto, Portugal.
Analytical biochemistry.Anal Biochem.2012 Jan 1;420(1):1-6. Epub 2011 Sep 16.
Melatonin is a hormone, a derivative of tryptophan, that possesses a potent scavenging capacity for the most reactive and dangerous free radicals, being an important protection against oxidative stress. In this work, an automated flow-based procedure for assessment of melatonin, tryptophan, and 5-hy
PMID 21964500

Japanese Journal

Anti-Oxidative, Anti-Tumor-Promoting, and Anti-Carcinogensis Activities of Nitroastaxanthin and Nitrolutein, the Reaction Products of Astaxanthin and Lutein with Peroxynitrite

Maoka Takashi,Tokuda Harukuni,Suzuki Nobutaka,Kato Hideaki,Etoh Hideo
Marine Drugs 10(6), 1391-1399, 2012-06-18
NAID 120004247731

AMPキナーゼと一酸化窒素(NO)ならびに活性窒素(ONOO[-])

細川雅也,藤田義人,稲垣暢也
内分泌・糖尿病・代謝内科 33(2), 133-138, 2011-08
NAID 40019010695

Related Pictures

★リンクテーブル★

リンク元	「ペルオキシ亜硝酸」「亜硝酸過酸化物」「パーオキシナイトライト」「ペルオキシナイトライト」「過酸化亜硝酸」