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Nitrotyrosine

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Nitrotyrosine
Names
IUPAC name (2S)-2-Amino-3-(4-hydroxy-3-nitrophenyl)propanoic acid
Other names 3-Nitro-L-tyrosine; 3-Nitrotyrosine
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.009.718 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C9H10N2O5/c10-6(9(13)14)3-5-1-2-8(12)7(4-5)11(15)16/h1-2,4,6,12H,3,10H2,(H,13,14)/t6-/m0/s1Key: FBTSQILOGYXGMD-LURJTMIESA-N
  • InChI=1/C9H10N2O5/c10-6(9(13)14)3-5-1-2-8(12)7(4-5)11(15)16/h1-2,4,6,12H,3,10H2,(H,13,14)/t6-/m0/s1Key: FBTSQILOGYXGMD-LURJTMIEBK
SMILES
  • O=()c1cc(ccc1O)C(C(=O)O)N
Properties
Chemical 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 otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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. 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 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, septic shock and coeliac disease. 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. Peroxynitrite and/or nitrative stress may participate in the pathogenesis of diabetes.

Research shows that nitrotyrosine levels can be reduced by N-acetyl cysteine, 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.

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

Nitrotyrosine, as a marker of reactive oxygen species, has also been linked to degeneration of dopamine neurons. Tyrosine is the precursor to dopamine, a neurotransmitter that's important for motivation, attention, learning, circadian rhythms, and other biological processes.

References

  1. "3-Nitro-L-tyrosine". 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). Elsevier Science: 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). Elsevier; Association for Academic Surgery: 143–149. doi:10.1016/j.jss.2005.10.008. PMID 16360172.
  4. ^ Pacher P, Beckman JS, Liaudet L (1 January 2007). "Nitric Oxide and Peroxynitrite in Health and Disease". Physiological Reviews. 87 (1). American Physiological Society: 315–424. doi:10.1152/physrev.00029.2006. PMC 2248324. 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 Letters. 350 (1). Wiley Publishing: 9–12. doi:10.1016/0014-5793(94)00722-5. PMID 8062931.
  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). Elsevier Science: 771–774. 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): 953–963. doi:10.1016/s0891-5849(98)00184-1. 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): 341–351. 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): 267–275. doi:10.2174/0929867053363207. PMC 2225483. PMID 15723618.
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  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): 847–856. doi:10.1002/hep.21115. PMID 16557556. S2CID 24189201.
  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): 1219–1226. doi:10.1038/sj.bjp.0703421. PMC 1572181. 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): 647–652. 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): 521–527. doi:10.1042/bj20030670. PMC 1223612. PMID 12797864.
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