Nitrotyrosine

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Nitrotyrosine[1]
Nitrotyrosine.png
Names
IUPAC name
(2S)-2-Amino-3-(4-hydroxy-3-nitrophenyl)propanoic acid
Other names
3-Nitro-L-tyrosine; 3-Nitrotyrosine
Identifiers
621-44-3 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:44454 YesY
ChemSpider 58633 YesY
DrugBank DB03867 YesY
ECHA InfoCard 100.009.718
PubChem 65124
UNII 7COY1HA6HK N
Properties
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 otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
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][11] 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.[12]

Free nitrotyrosine undergoes metabolism to form 3-nitro-4-hydroxyphenylacetic acid (NHPA) which is excreted in the urine.[13][14]

References[edit]

  1. ^ 3-Nitro-L-tyrosine at Sigma-Aldrich
  2. ^ Ischiropoulos H (August 1998). "Biological tyrosine nitration: a pathophysiological function of nitric oxide and reactive oxygen species". Archives of Biochemistry and Biophysics. 356 (1): 1–11. doi:10.1006/abbi.1998.0755. PMID 9681984. 
  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". The Journal of Surgical Research. 133 (2): 143–9. doi:10.1016/j.jss.2005.10.008. PMID 16360172. 
  4. ^ Pacher P, Beckman JS, Liaudet L (January 2007). "Nitric oxide and peroxynitrite in health and disease". Physiological Reviews. 87 (1): 315–424. doi:10.1152/physrev.00029.2006. PMC 2248324Freely accessible. PMID 17237348. 
  5. ^ Kaur H; Halliwell B (1994). "Evidence for nitric oxide-mediated oxidative damage in chronic inflammation Nitrotyrosine in serum and synovial fluid from rheumatoid patients". FEBS Lett. 350: 9–12. doi:10.1016/0014-5793(94)00722-5. 
  6. ^ Fukuyama N, Takebayashi Y, Hida M, Ishida H, Ichimori K, Nakazawa H (1997). "Clinical evidence of peroxynitrite formation in chronic renal failure patients with septic shock". Free Radical Biology & Medicine. 22 (5): 771–4. doi:10.1016/S0891-5849(96)00401-7. PMID 9119244. 
  7. ^ ter Steege JC, Koster-Kamphuis L, van Straaten EA, Forget PP, Buurman WA (November 1998). "Nitrotyrosine in plasma of celiac disease patients as detected by a new sandwich ELISA". Free Radical Biology & Medicine. 25 (8): 953–63. PMID 9840741. 
  8. ^ Buddi R, Lin B, Atilano SR, Zorapapel NC, Kenney MC, Brown DJ (March 2002). "Evidence of oxidative stress in human corneal diseases". The Journal of Histochemistry and Cytochemistry. 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". Current Medicinal Chemistry. 12 (3): 267–75. doi:10.2174/0929867053363207. PMC 2225483Freely accessible. PMID 15723618. 
  10. ^ Ivanovski O, Szumilak D, Nguyen-Khoa T, Ruellan N, Phan O, Lacour B, Descamps-Latscha B, Drüeke TB, Massy ZA (June 2005). "The antioxidant N-acetylcysteine prevents accelerated atherosclerosis in uremic apolipoprotein E knockout mice". Kidney International. 67 (6): 2288–94. doi:10.1111/j.1523-1755.2005.00332.x. PMID 15882270. 
  11. ^ Mani AR, Ippolito S, Ollosson R, Moore KP (April 2006). "Nitration of cardiac proteins is associated with abnormal cardiac chronotropic responses in rats with biliary cirrhosis". Hepatology. 43 (4): 847–56. doi:10.1002/hep.21115. PMID 16557556. 
  12. ^ Cuzzocrea S, Mazzon E, Costantino G, Serraino I, Dugo L, Calabrò G, Cucinotta G, De Sarro A, Caputi AP (July 2000). "Beneficial effects of n-acetylcysteine on ischaemic brain injury". British Journal of Pharmacology. 130 (6): 1219–26. doi:10.1038/sj.bjp.0703421. PMC 1572181Freely accessible. PMID 10903958. 
  13. ^ Ohshima H, Friesen M, Brouet I, Bartsch H (September 1990). "Nitrotyrosine as a new marker for endogenous nitrosation and nitration of proteins". Food and Chemical Toxicology. 28 (9): 647–52. doi:10.1016/0278-6915(90)90173-k. PMID 2272563. 
  14. ^ Mani AR, Pannala AS, Orie NN, Ollosson R, Harry D, Rice-Evans CA, Moore KP (September 2003). "Nitration of endogenous para-hydroxyphenylacetic acid and the metabolism of nitrotyrosine". The Biochemical Journal. 374 (Pt 2): 521–7. doi:10.1042/bj20030670. PMID 12797864.