Nitrotyrosine

Nitrotyrosine^[1]

Names
IUPAC name (2S)-2-Amino-3-(4-hydroxy-3-nitrophenyl)propanoic acid
Other names 3-Nitro-L-tyrosine; 3-Nitrotyrosine
Identifiers
CAS Number	621-44-3
ChEBI	CHEBI:44454
ChemSpider	58633
DrugBank	DB03867
Jmol interactive 3D	Image
PubChem	65124
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/s1 Key: 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/s1 Key: FBTSQILOGYXGMD-LURJTMIEBK
SMILES O=[N+]([O-])c1cc(ccc1O)C[C@@H](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 [77 °F], 100 kPa).
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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

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: 1–11.
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). "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; Takeyashi Y (1997). Free Radical Biol. Med 22. Missing or empty |title= (help)
7. Ter Steege JCA; Koster-Kamphuis I; Van Straaten E; Forget P; Buurman WA (1998). Free Radic Biol Med 25. Missing or empty |title= (help)
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. 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 (Baltimore, Md.) 43 (4): 847–56. doi:10.1002/hep.21115. PMID 16557556.
12. "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.
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 (1 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.