Nitration tyrosine

Van Zyl JM, BJ van der Walt (1994) Apparent hydroxyl radical generation without transition metal catalysts and tyrosine nitration during oxidation of the anti-tubercular drug, isonicotinic acid hydrazide. Biochem Pharmacol 48 2033-2042. 

Greenacre, S.A., and Ischiropoulos, H. (2001) Tyrosine nitration Localisation, quantification, consequences for protein function and signal transduction. Free Radic. Res. 34, 541-581. 

Peroxynitrite (ONOO-) is a cytotoxic reactive species that is formed by the reaction of nitric oxide and superoxide. Methods for measuring the scavenging capacity of peroxynitrite usually depend on either the inhibition of tyrosine nitration or the inhibition of dihydrorhodamine 123 (DHR) oxidation to rhodamine 123 (MacDonalds-Wicks and... 

Pannala A, Razaq R, Halliwell B, Singh S and Rice-Evans CA. 1998. Inhibition of peroxynitrite dependent tyrosine nitration by hydroxycinnamates nitration or electron donation Free Radic Biol Med 24(4) 594-606. 

It has been proposed [91] that nitric dioxide radical formation during the oxidation of nitrite by HRP or lactoperoxidase (LPO) can contribute to tyrosine nitration and be involved in cell and tissue injuries. This proposal was supported in the later work [92] where it has been shown that N02 formed in peroxide-catalyzed reactions is able to enter cells and induce tyrosyl nitration. Reszka et al. [93] demonstrated that N02 mediated the oxidation of biological electron donors and antioxidants (NADH, NADPH, cysteine, glutathione, ascorbate, and Trolox C) catalyzed by lactoperoxidase in the presence of nitrite. 

Similar to peroxynitrite, ONOOCOO- reacts with many biomolecules such as uric acid [110], oxyhemoglobin [133], melatonin [135], NADH, ubiquinol Q0, and glutathione [141], Reactions of ONOOCOO with substrates in mitochondrial matrix is accompanied by protein nitration [141]. The reaction of ONOOCOO- with GSH was so rapid that glutathione inhibited tyrosine nitration by peroxynitrite in the presence of C02 [142], The formation of ONOOCOO- increased the formation of 3-nitrotyrosine and decreased the formation of 3-hydroxytyrosine probably due to the enhanced selectivity of C03 - compared to hydroxyl radicals [143],... 

The formation of peroxynitrite in cells and tissue is frequently characterized by the formation of nitrotyrosine. The formation of nitrotyrosine is not a very specific assay of peroxynitrite detection because the other nitrogen oxide may also take part in this process, but peroxynitrite is undoubtedly the most efficient nitrating agent. (Mechanism of tyrosine nitration by peroxynitrite and other reactive nitrogen compounds has been considered in Chapters 21 and 22.)... 

Bruijn, L. I., Beal, M. F., Becher, M. W. et al. Elevated free nitrotyrosine levels, but not protein-bound nitrotyrosine or hydroxyl radicals, throughout amyotrophic lateral sclerosis (ALS)-like disease implicate tyrosine nitration as an aberrant in vivo property of one familial ALS-linked superoxide dismutase 1 mutant. Proc. Natl Acad. Sci. U.S.A. 94 7606-7611,1997. 

Ischiropoulos, H., Zhu, L., and Beckman, J. S. (1992a). Peroxynitrite formation from activated rat alveolar macrophages. Arch. Biochem. Biophys. 298, 446-451. Ischiropoulos, H., Zhu, L., Chen, J., Tsai, H. M., Martin, J. C., Smith, C. D., and Beckman, J. S. (1992b). Peroxynitrite-mediated tyrosine nitration catalyzed by superoxide dismutase. Arch. Biochem. Biophys. 298, 431-437. 

Sadeghipour M, Terreux R, Phipps J. 2005. Flavonoids and tyrosine nitration Structure-activity relationship correlation with enthalpy of formation. Toxicol in Vitro 19 155-165. 

In vivo, peroxynitrite may be intercepted by various cellular agents which will keep its steady-state low (Table 2.4). Not all these interceptors, however, react with peroxynitrite to non-reactive products. For example, carbon dioxide enhances tyrosine nitration and thiyl radical formation. Myeloperoxidase also enhances tyrosine nitration, and in the reactions with GSH and albumin thiyl radicals are formed (for details see Arteel et al. 1999). 

Mattson, M. P., Goodman, Y., Luo, H., Fu, W., and Furukawa, K. (1997). Activation of NF-kappaB protects hippocampal neurons against oxidative stress-induced apoptosis Evidence for induction of manganese superoxide dismutase and suppression of peroxynitrite production and protein tyrosine nitration.. Neurosci. Res. 49, 681-697. 

M. Whiteman et al., Lack of tyrosine nitration by hypochlorous acid in the presence of physiological concentration of nitrite. J. Biol. Chem. 278, 8380-8384 (2003)... 

H. Ischiropoulos, Biological tyrosine nitration A pathophysiological function of nitric oxide and reactive oxygen species. Arch. Biochem. Biophys. 356, 1-11 (1998)... 

Because of the instability of peroxynitrite under physiological conditions, the detection of 3-nitrotyrosine (NC>2-Tyr) has become a biochemical marker for the presence of peroxynitrite in pathophysiological processes. The biological significance of tyrosine nitration is a subject of great interest, because extensive evidence supports the formation of nitrotyrosine in vivo in diverse pathological conditions such as heart diseases, chronic inflammation and autoimmune diseases, cancer, Parkinson s disease, Alzheimer s disease, multiple sclerosis, amyotrophic lateral sclerosis, and ischemia-reperfusion injury [11]. 

Radi, R. Nitric oxide, oxidants, and protein tyrosine nitration. Proc. Natl. Acad. 

The 250-320 nm spectrum shows an important change around 280 nm for nitrated CGTase in comparison with that of native enzyme. This is in part due to tyrosine nitration. In particular, the dichroism observed around 300 nm in the differential spectrum (results... 

---