Nitrotyrosine

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Nitrotyrosine[1]
Nitrotyrosine.png
Identifiers
CAS number 621-44-3 YesY
PubChem 65124
ChemSpider 58633 YesY
DrugBank DB03867
ChEBI CHEBI:44454 YesY
Jmol-3D images Image 1
Properties
Molecular formula C9H10N2O5
Molar mass 226.19 g/mol
Appearance Yellow to green crystalline solid
Melting point 233 to 235 °C (451 to 455 °F; 506 to 508 K) (decomposes)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
Infobox references

Nitrotyrosine is a product of tyrosine nitration mediated by reactive nitrogen species such as peroxynitrite anion and nitrogen dioxide. Nitrotyrosine is identified as an indicator or marker of cell damage, inflammation as well as NO (nitric oxide) production. Nitrotyrosine is formed in the presence of the active metabolite NO. Generally in many disease states, oxidative stress increases the production of superoxide (O2) and NO forming peroxynitrite (ONOO) a destructive free radical oxidant [2] The production of ONOO is capable of oxidizing several lipoproteins and of nitrating tyrosine residues in many proteins. It is difficult to determine the production of ONOO so, usually nitrotyrosine in proteins are the detectable marker for indirectly detecting ONOO. It is detected in large number of pathological conditions[3][4] and is considered a marker of NO-dependent, reactive nitrogen species-induced nitrative stress. Nitrotyrosine is detected in biological fluids such as plasma, lung aspirants-BALF (Broncho alveolar lining fluid and urine. Increased level of nitrotyrosine is detected in rheumatoid arthritis [5] septic shock[6] and coeliac disease.[7] In all these studies nitrotyrosine was undetected in healthy subjects. Nitrotyrosine is also found in numerous other disease-affected tissues, such as the cornea in keratoconus.[8] Peroxynitrite and/or nitrative stress may participate in the pathogenesis of diabetes[9]

Research shows that nitrotyrosine levels can be reduced by N-acetyl cysteine,[10] which is a precursor to glutathione, one of the body's primary endogenous antioxidants. Nitrotyrosine levels have been linked to cerebral ischemia and edema, for which NAC has also been proven as a potential treatment.[11]

References[edit]

  1. ^ 3-Nitro-L-tyrosine at Sigma-Aldrich
  2. ^ Ischiropoulous H (1998) Biological tyrosine nitration: a pathophysiological function of nitric oxide and reactive oxygen species. Arch Biochem Biophys 356: pg1-11.
  3. ^ Mohiuddin I, Chai H, Lin PH, Lumsden AB, Yao Q, Chen C (June 2006). "Nitrotyrosine and chlorotyrosine: clinical significance and biological functions in the vascular system". J. Surg. Res. 133 (2): 143–9. doi:10.1016/j.jss.2005.10.008. PMID 16360172. 
  4. ^ Pacher P, Beckman JS, Liaudet L (2007). "Nitric oxide and peroxynitrite in health and disease.". Physiol Rev. 87 (1): 315–424. doi:10.1152/physrev.00029.2006. PMC 2248324. PMID 17237348. 
  5. ^ Kaur H; Halliwell B (1994). FEBS Lett 350. doi:10.1016/0014-5793(94)00722-5. 
  6. ^ Fukuyama N; Takeyashi Y (1997). Free Radical Biol. Med 22. 
  7. ^ Ter Steege JCA; Koster-Kamphuis I, Van Straaten E, Forget P, Buurman WA (1998). Free Radic Biol Med 25. 
  8. ^ Buddi R, Lin B, Atilano SR, Zorapapel NC, Kenney MC, Brown DJ (March 2002). "Evidence of oxidative stress in human corneal diseases". J. Histochem. Cytochem. 50 (3): 341–51. doi:10.1177/002215540205000306. PMID 11850437. 
  9. ^ Pacher P, Obrosova IG, Mabley JG, Szabó C (2005). "Role of nitrosative stress and peroxynitrite in the pathogenesis of diabetic complications. Emerging new therapeutical strategies". Curr. Med. Chem. 12 (3): 267–75. doi:10.2174/0929867053363207. PMC 2225483. PMID 15723618. 
  10. ^ "The antioxidant N-acetylcysteine prevents accelerated atherosclerosis in uremic apolipoprotein E knockout mice". Kidney Int. 67 (6): 2288–94. June 2005. doi:10.1111/j.1523-1755.2005.00332.x. PMID 15882270. 
  11. ^ "Beneficial effects of n-acetylcysteine on ischaemic brain injury". Br. J. Pharmacol. 130 (6): 1219–26. July 2000. doi:10.1038/sj.bjp.0703421. PMC 1572181. PMID 10903958.