Isomerization and Nitro-Oxidation of Arachidonic Acid by NO2

  • Michael Balazy
  • Jordi López-Fernández
Part of the Advances in Experimental Medicine and Biology book series (AEMB, volume 525)


Free radical-mediated oxidation of arachidonic acid leads to formation of iso-eicosanoids, such as isoprostaglandins, isolevuglandins, hydroperoxides, and other products that could function as markers and/or mediators of oxidative stress initiated by a hydroxyl radical. Much less has been known about modifications of arachidonic acid by reactive nitrogen radicals such as NO2, a major product of NO oxidation in vivo and a component of polluted air and smoke. We studied the reaction of NO2 with arachidonic acid to characterize lipid products and their biological activity and usefulness as markers of NO2 interaction with biological membranes.


Arachidonic Acid Guanylate Cyclase Reactive Nitrogen Species Nitrogen Dioxide Aqueous Model System 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    Jiang H, Kruger N, Lahiri DR, Wang D, Vatele JM, Balazy M. Nitrogen dioxide induces cis-trans isomerization of arachidonic acid within cellular phospholipids. Detection of trans-arachidonic acids in vivo. J Biol Chem 1999; 274:16235–41.PubMedCrossRefGoogle Scholar
  2. 2.
    Krishna UM, Reddy MM, Xia J, Falck JR, Balazy M. Stereospecific synthesis of trans-arachidonic acids. Bioorg Med Chem Lett 2001; 11:2415–18.PubMedCrossRefGoogle Scholar
  3. 3.
    Prütz WA, Monig H, Butler J, Land EJ. Reactions of nitrogen dioxide in aqueous model systems: oxidation of tyrosine units in peptides and proteins. Arch Biochem Biophys 1985; 243:125–34.PubMedCrossRefGoogle Scholar
  4. 4.
    Patel JM, Block ER. Nitrogen dioxide-induced changes in cell membrane fluidity and function. Am Rev Respir Dis 1986; 134:1196–202.PubMedGoogle Scholar
  5. 5.
    Balazy M. Trans-arachidonic acids: new mediators of inflammation. J Physiol Pharmacol 2000; 51:597–607.PubMedGoogle Scholar
  6. 6.
    Balazy M, Iesaki T, Park JL, Jiang H, Kaminski PM, Wolin MS. Vicinal nitrohydroxyeicosatrienoic acids: vasodilator lipids formed by reaction of nitrogen dioxide with arachidonic acid. J Pharmacol Exp Ther 2001; 299:611–19.PubMedGoogle Scholar
  7. 7.
    O’Donnell VB, Eiserich JP, Chumley PH, Jablonsky MJ, Krishna NR, Kirk M, Barnes S, Darley-Usmar VM, Freeman BA. Nitration of unsaturated fatty acids by nitric oxide-derived reactive nitrogen species peroxynitrite, nitrous acid, nitrogen dioxide, and nitronium ion. Chem Res Toxicol 1999; 12:83–92.PubMedCrossRefGoogle Scholar
  8. 8.
    Coles B, Bloodsworth A, Eiserich JP, Coffey MJ, McLoughlin RM, Giddings JC, Lewis MJ, Haslam RJ, Freeman BA, O’Donnell VB. Nitrolinoleate inhibits platelet activation by attenuating calcium mobilization and inducing phosphorylation of vasodilator-stimulated phosphoprotein through elevation of cAMP. J Biol Chem 2002; 277:5832–40.PubMedCrossRefGoogle Scholar
  9. 9.
    Lima ES, Di Mascio P, Rubbo H, Abdalla DS. Characterization of linoleic acid nitration in human blood plasma by mass spectrometry. Biochemistry 2002; 41:10717–22.PubMedCrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2003

Authors and Affiliations

  • Michael Balazy
    • 1
  • Jordi López-Fernández
  1. 1.Department of PharmacologyNew York Medical CollegeValhallaUSA

Personalised recommendations