関: 3-nitro-L-tyrosine

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/12/12 09:41:40」(JST)

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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^[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

^ 3-Nitro-L-tyrosine at Sigma-Aldrich
^ Ischiropoulous H (1998) Biological tyrosine nitration: a pathophysiological function of nitric oxide and reactive oxygen species. Arch Biochem Biophys 356: pg1-11.
^ 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.
^ 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.
^ Kaur H; Halliwell B (1994). FEBS Lett 350. doi:10.1016/0014-5793(94)00722-5.
^ Fukuyama N; Takeyashi Y (1997). Free Radical Biol. Med 22.
^ Ter Steege JCA; Koster-Kamphuis I, Van Straaten E, Forget P, Buurman WA (1998). Free Radic Biol Med 25. Cite uses deprecated parameters (help)
^ 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.
^ 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.
^ "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.
^ "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.

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English Journal

Role of Toll like receptor 4 signaling pathway in the secondary damage induced by experimental spinal cord injury.

Impellizzeri D1, Ahmad A1, Di Paola R1, Campolo M1, Navarra M2, Esposito E1, Cuzzocrea S3.
Immunobiology.Immunobiology.2015 Sep;220(9):1039-49. doi: 10.1016/j.imbio.2015.05.013. Epub 2015 May 11.
Toll-like receptors (TLRs) are signaling receptors in the innate immune system that is specific immunologic response to systemic bacterial infection and injury. TLRs contribute to the initial induction of neuroinflammation in the CNS. In spinal cord injury (SCI) intricate immune cell interactions ar
PMID 25990044

The role of oxidative stress in corneal diseases and injuries.

Čejková J1, Čejka Č2.
Histology and histopathology.Histol Histopathol.2015 Aug;30(8):893-900. doi: 10.14670/HH-11-611. Epub 2015 Mar 24.
In various corneal injuries (such as chemical burns or irradiation of corneas with UVB radiation) and ocular diseases (e.g. dry eye disease, keratokonus, bullous keratopathy, Fuchs' endothelial dystrophy), the expressions of malondialdehyde (a marker of lipid peroxidation) and nitrotyrosine (a marke
PMID 25803192

Vitamin D3 pretreatment alleviates renal oxidative stress in lipopolysaccharide-induced acute kidney injury.

Xu S1, Chen YH2, Tan ZX1, Xie DD1, Zhang C3, Xia MZ4, Wang H3, Zhao H1, Xu DX5, Yu DX6.
The Journal of steroid biochemistry and molecular biology.J Steroid Biochem Mol Biol.2015 Aug;152:133-41. doi: 10.1016/j.jsbmb.2015.05.009. Epub 2015 May 23.
Increasing evidence demonstrates that reactive oxygen species plays important roles in sepsis-induced acute kidney injury. This study investigated the effects of VitD3 pretreatment on renal oxidative stress in sepsis-induced acute kidney injury. Mice were intraperitoneally injected with lipopolysacc
PMID 26013770

Japanese Journal

大気汚染物質によるスギ花粉アレルゲンCry j 1の化学的修飾と3-ニトロチロシンのHeLa細胞に対するアポトーシス誘導能に関する基礎研究 (特集次世代のエアロゾル科学・技術を拓く)

森田淳,王青躍,秀民 [他]
エアロゾル研究 27(1), 71-77, 2012
NAID 40019240798

5/6腎摘腎不全モデルにおける生薬オウギ(黄蓍)の腎一酸化窒素合成酵素(NOS)発現抑制効果

豊田一恵,谷本光生,松本昌和 [他]
順天堂医学 57(4), 387-394, 2011
NAID 40018975703

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リンク元	「ニトロチロシン」「3-nitro-L-tyrosine」

「ニトロチロシン」

Nitrotyrosine
	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
PubChem	65124
ChemSpider	58633
DrugBank	DB03867
ChEBI	CHEBI:44454
Jmol-3D images	Image 1
	SMILES O=[N+]([O-])c1cc(ccc1O)C[C@@H](C(=O)O)N ;
	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 ;
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)
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	Infobox references