Chemistry:Nitrotyrosine
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| IUPAC name
(2S)-2-Amino-3-(4-hydroxy-3-nitrophenyl)propanoic acid
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| Other names
3-Nitro-L-tyrosine; 3-Nitrotyrosine
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| 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). | |
 verify (what is   ?)
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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.[4][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]
Nitrotyrosine, as a marker of reactive oxygen species, has also been linked to degeneration of dopamine neurons.[15] Tyrosine is the precursor to dopamine, a neurotransmitter that's important for motivation, attention, learning, circadian rhythms, and other biological processes.
References
- ↑ "3-Nitro-L-tyrosine". https://www.sigmaaldrich.com/IN/en/product/sigma/n7389.
- ↑ "Biological Tyrosine Nitration: A Pathophysiological Function of Nitric Oxide and Reactive Oxygen Species". Archives of Biochemistry and Biophysics (Elsevier Science) 356 (1): 1–11. August 1998. doi:10.1006/abbi.1998.0755. PMID 9681984.
- ↑ "Nitrotyrosine and Chlorotyrosine: Clinical Significance and Biological Functions in the Vascular System". The Journal of Surgical Research (Elsevier; Association for Academic Surgery) 133 (2): 143–149. June 2006. doi:10.1016/j.jss.2005.10.008. PMID 16360172.
- ↑ 4.0 4.1 "Nitric Oxide and Peroxynitrite in Health and Disease". Physiological Reviews (American Physiological Society) 87 (1): 315–424. 1 January 2007. doi:10.1152/physrev.00029.2006. PMID 17237348.
- ↑ "Evidence for nitric oxide-mediated oxidative damage in chronic inflammation Nitrotyrosine in serum and synovial fluid from rheumatoid patients". FEBS Letters (Wiley Publishing) 350 (1): 9–12. 1994. doi:10.1016/0014-5793(94)00722-5. PMID 8062931.
- ↑ "Clinical evidence of peroxynitrite formation in chronic renal failure patients with septic shock". Free Radical Biology & Medicine (Elsevier Science) 22 (5): 771–774. 1997. doi:10.1016/S0891-5849(96)00401-7. PMID 9119244.
- ↑ "Nitrotyrosine in plasma of celiac disease patients as detected by a new sandwich ELISA". Free Radical Biology & Medicine 25 (8): 953–963. November 1998. doi:10.1016/s0891-5849(98)00184-1. PMID 9840741.
- ↑ "Evidence of oxidative stress in human corneal diseases". The Journal of Histochemistry and Cytochemistry 50 (3): 341–351. March 2002. doi:10.1177/002215540205000306. PMID 11850437.
- ↑ "Role of nitrosative stress and peroxynitrite in the pathogenesis of diabetic complications. Emerging new therapeutical strategies". Current Medicinal Chemistry 12 (3): 267–275. 2005. doi:10.2174/0929867053363207. PMID 15723618.
- ↑ "The antioxidant N-acetylcysteine prevents accelerated atherosclerosis in uremic apolipoprotein E knockout mice". Kidney International 67 (6): 2288–2294. June 2005. doi:10.1111/j.1523-1755.2005.00332.x. PMID 15882270.
- ↑ "Nitration of cardiac proteins is associated with abnormal cardiac chronotropic responses in rats with biliary cirrhosis". Hepatology 43 (4): 847–856. April 2006. doi:10.1002/hep.21115. PMID 16557556.
- ↑ "Beneficial effects of n-acetylcysteine on ischaemic brain injury". British Journal of Pharmacology 130 (6): 1219–1226. July 2000. doi:10.1038/sj.bjp.0703421. PMID 10903958.
- ↑ "Nitrotyrosine as a new marker for endogenous nitrosation and nitration of proteins". Food and Chemical Toxicology 28 (9): 647–652. September 1990. doi:10.1016/0278-6915(90)90173-k. PMID 2272563.
- ↑ "Nitration of endogenous para-hydroxyphenylacetic acid and the metabolism of nitrotyrosine". The Biochemical Journal 374 (Pt 2): 521–527. September 2003. doi:10.1042/bj20030670. PMID 12797864.
- ↑ "Nitrotyrosine as a marker for peroxynitrite-induced neurotoxicity: The beginning or the end of the end of dopamine neurons?". Journal of Neurochemistry 89 (3): 529–536. 2004. doi:10.1111/j.1471-4159.2004.02346.x. PMID 15086510.
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