Reactions of peroxynitrite leading to either apoptotic or necrotic cell death

Peroxynitrite (sometimes called peroxonitrite) is an

ion An ion () is an atom or molecule with a net electrical charge. The charge of an electron is considered to be negative by convention and this charge is equal and opposite to the charge of a proton, which is considered to be positive by conv ...

with the formula ONOO⁻. It is a

structural isomer In chemistry, a structural isomer (or constitutional isomer in the IUPAC nomenclature) of a compound is another compound whose molecule has the same number of atoms of each element, but with logically distinct bonds between them. The term metam ...

nitrate Nitrate is a polyatomic ion with the chemical formula . Salts containing this ion are called nitrates. Nitrates are common components of fertilizers and explosives. Almost all inorganic nitrates are soluble in water. An example of an insolubl ...

Preparation

Peroxynitrite can be prepared by the reaction of

superoxide In chemistry, a superoxide is a compound that contains the superoxide ion, which has the chemical formula . The systematic name of the anion is dioxide(1−). The reactive oxygen ion superoxide is particularly important as the product of th ...

with

nitric oxide Nitric oxide (nitrogen oxide or nitrogen monoxide) is a colorless gas with the formula . It is one of the principal oxides of nitrogen. Nitric oxide is a free radical: it has an unpaired electron, which is sometimes denoted by a dot in its ch ...

: : It is prepared by the reaction of

hydrogen peroxide Hydrogen peroxide is a chemical compound with the formula . In its pure form, it is a very pale blue liquid that is slightly more viscous than water. It is used as an oxidizer, bleaching agent, and antiseptic, usually as a dilute solution (3 ...

with

nitrite The nitrite ion has the chemical formula . Nitrite (mostly sodium nitrite) is widely used throughout chemical and pharmaceutical industries. The nitrite anion is a pervasive intermediate in the nitrogen cycle in nature. The name nitrite also re ...

: : H₂O₂ + → ONOO⁻ + H₂O Its presence is indicated by the

absorbance Absorbance is defined as "the logarithm of the ratio of incident to transmitted radiant power through a sample (excluding the effects on cell walls)". Alternatively, for samples which scatter light, absorbance may be defined as "the negative lo ...

at 302 nm (pH 12, ''ε''₃₀₂ = 1670 M⁻¹ cm⁻¹).

Reactions

Peroxynitrite is weakly basic with a p''K''_a of ~6.8. It is reactive toward DNA and proteins. ONOO⁻ reacts nucleophilically with

carbon dioxide Carbon dioxide ( chemical formula ) is a chemical compound made up of molecules that each have one carbon atom covalently double bonded to two oxygen atoms. It is found in the gas state at room temperature. In the air, carbon dioxide is tr ...

. ''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 () is by far the predominant pathway for ONOO⁻. homolyzes to form carbonate radical and nitrogen dioxide, again as a pair of

caged In music, a barre chord (also spelled bar chord) is a type of chord on a guitar or other stringed instrument played by using one finger to press down multiple strings across a single fret of the fingerboard (like a bar pressing down the st ...

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 Nitrogen dioxide is a chemical compound with the formula . It is one of several nitrogen oxides. is an intermediate in the industrial synthesis of nitric acid, millions of tons of which are produced each year for use primarily in the producti ...

) that are believed to cause peroxynitrite-related cellular damage.

Peroxynitrous acid

Its

conjugate acid A conjugate acid, within the Brønsted–Lowry acid–base theory, is a chemical compound formed when an acid donates a proton () to a base—in other words, it is a base with a hydrogen ion added to it, as in the reverse reaction it loses a ...

peroxynitrous acid is highly reactive, although peroxynitrite is stable in basic solutions.

References

{{Nitrogen compounds Oxyanions Atmospheric chemistry Toxins

Preparation

Reactions

Peroxynitrous acid

See also

References