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J. Biol. Chem., Vol. 269, Issue 6, 4317-4326, Feb, 1994
JD Morrow, TA Minton, CR Mukundan, MD Campbell, WE Zackert, VC Daniel, KF Badr, IA Blair and LJ Roberts 2nd
We recently reported the discovery that a series of novel prostaglandin
(PG)F2-like compounds (F2-isoprostanes) are produced in vivo independent of
the cyclooxygenase as products of free radical-catalyzed lipid
peroxidation. F2-isoprostanes are initially formed in situ from arachidonic
acid esterified to phospholipids and then released preformed. We have now
investigated whether PGD2/E2-like isoprostanes are also produced by
rearrangement of the PGG2-like intermediates involved in isoprostane
formation. Using a variety of approaches utilizing mass spectrometry,
compelling evidence was obtained for the presence of
D2/E2-isoprostane-containing phosphospholipids in the liver (85 +/- 33 ng/g
of liver) and free D2/E2-isoprostanes in the circulation (215 +/- 90 pg/ml)
of rats treated with CCl4 to induce lipid peroxidation. In untreated rats,
levels of D2/E2-isoprostanes esterified in liver phospholipids were much
lower (0.90 +/- 0.10 ng/g), and free compounds could not be detected in the
circulation (< 5 pg/ml). Interestingly, one of the E2-isoprostanes that
would be expected to be formed in abundance, 8-epi-PGE2, was found to be a
potent renal vasoconstrictor, and these effects could be abrogated by
SQ29548, a thromboxane receptor antagonist. Further understanding of the
biological consequences of the formation of these novel compounds and
factors that influence their formation may provide valuable insights into
the pathophysiology of oxidant injury.
Free radical-induced generation of isoprostanes in vivo. Evidence for the formation of D-ring and E-ring isoprostanes
Department of Pharmacology, Vanderbilt University School of Medicine, Nashville, Tennessee 37232-6602.
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J. D. Morrow, J. Scruggs, Y. Chen, W. E. Zackert, and L. J. R. II Evidence that the E2-isoprostane, 15-E2t-isoprostane (8-iso-prostaglandin E2) is formed in vivo J. Lipid Res., August 1, 1998; 39(8): 1589 - 1593. [Abstract] [Full Text]
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L. J. Roberts II, T. J. Montine, W. R. Markesbery, A. R. Tapper, P. Hardy, S. Chemtob, W. D. Dettbarn, and J. D. Morrow Formation of Isoprostane-like Compounds (Neuroprostanes) in Vivo from Docosahexaenoic Acid J. Biol. Chem., May 29, 1998; 273(22): 13605 - 13612. [Abstract] [Full Text] [PDF]
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 J. F. Reckelhoff, V. Kanji, L. C. Racusen, A. M. Schmidt, S. Du Yan, J. Morrow, L. J. Roberts II, and A. K. Salahudeen Vitamin E ameliorates enhanced renal lipid peroxidation and accumulation of F2-isoprostanes in aging kidneys Am J Physiol Regulatory Integrative Comp Physiol, March 1, 1998; 274(3): R767 - R774. [Abstract] [Full Text] [PDF]
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M. P. Reilly, N. Delanty, L. Roy, J. Rokach, P. O. Callaghan, P. Crean, J. A. Lawson, and G. A. FitzGerald Increased Formation of the Isoprostanes IPF2{alpha}-I and 8-Epi-Prostaglandin F2{alpha} in Acute Coronary Angioplasty : Evidence for Oxidant Stress During Coronary Reperfusion in Humans Circulation, November 18, 1997; 96(10): 3314 - 3320. [Abstract] [Full Text]
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 C. Patrono and G. A. FitzGerald Isoprostanes: Potential Markers of Oxidant Stress in Atherothrombotic Disease Arterioscler. Thromb. Vasc. Biol., November 1, 1997; 17(11): 2309 - 2315. [Abstract] [Full Text]
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P. Kunapuli, J. A. Lawson, J. Rokach, and G. A. FitzGerald Functional Characterization of the Ocular Prostaglandin F2alpha (PGF2alpha ) Receptor. ACTIVATION BY THE ISOPROSTANE, 12-iso-PGF2alpha J. Biol. Chem., October 24, 1997; 272(43): 27147 - 27154. [Abstract] [Full Text] [PDF]
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J. L. Elmhurst, P.-A. Betti, and P. K. Rangachari Intestinal Effects of Isoprostanes: Evidence for the Involvement of Prostanoid EP and TP Receptors J. Pharmacol. Exp. Ther., September 1, 1997; 282(3): 1198 - 1205. [Abstract] [Full Text]
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T. Klein, F. Reutter, H. Schweer, H. W. Seyberth, and R. M. Nüsing Generation of the Isoprostane 8-Epi-prostaglandin F2alpha In Vitro and In Vivo via the Cyclooxygenases J. Pharmacol. Exp. Ther., September 1, 1997; 282(3): 1658 - 1665. [Abstract] [Full Text]
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 F. van Kooten, G. Ciabattoni, C. Patrono, D. W. J. Dippel, and P. J. Koudstaal Platelet Activation and Lipid Peroxidation in Patients With Acute Ischemic Stroke Stroke, August 1, 1997; 28(8): 1557 - 1563. [Abstract] [Full Text]
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N. Delanty, M.P. Reilly, D. Pratico, J.A. Lawson, J.F. McCarthy, A.E. Wood, S.T. Ohnishi, D.J. Fitzgerald, and G.A. FitzGerald 8-Epi PGF2{alpha} Generation During Coronary Reperfusion: A Potential Quantitative Marker of Oxidant Stress In Vivo Circulation, June 3, 1997; 95(11): 2492 - 2499. [Abstract] [Full Text]
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B. T. Kinsella, D. J. O'Mahony, and G. A. Fitzgerald The Human Thromboxane A2 Receptor alpha Isoform (TPalpha ) Functionally Couples to the G Proteins Gq and G11 In Vivo and is Activated by the Isoprostane 8-epi Prostaglandin F2alpha J. Pharmacol. Exp. Ther., May 1, 1997; 281(2): 957 - 964. [Abstract] [Full Text]
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S. W. Hoffman, S. Moore, and E. F. Ellis Isoprostanes: Free Radical–Generated Prostaglandins With Constrictor Effects on Cerebral Arterioles Stroke, April 1, 1997; 28(4): 844 - 849. [Abstract] [Full Text]
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J. D. Morrow, J. A. Awad, A. Wu, W. E. Zackert, V. C. Daniel, and L. J. Roberts II Nonenzymatic Free Radical-catalyzed Generation of Thromboxane-like Compounds (Isothromboxanes) in Vivo J. Biol. Chem., September 20, 1996; 271(38): 23185 - 23190. [Abstract] [Full Text] [PDF]
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L. J. Roberts II, K. P. Moore, W. E. Zackert, J. A. Oates, and J. D. Morrow Identification of the Major Urinary Metabolite of the F2-isoprostane 8-Iso-prostaglandin F2alpha in Humans J. Biol. Chem., August 23, 1996; 271(34): 20617 - 20620. [Abstract] [Full Text] [PDF]
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M. Reilly, N. Delanty, J. A. Lawson, and G. A. FitzGerald Modulation of Oxidant Stress In Vivo in Chronic Cigarette Smokers Circulation, July 1, 1996; 94(1): 19 - 25. [Abstract] [Full Text]
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D. Pratico, E. M. Smyth, F. Violi, and G. A. FitzGerald Local Amplification of Platelet Function by 8-Epi Prostaglandin F2alpha Is Not Mediated by Thromboxane Receptor Isoforms J. Biol. Chem., June 21, 1996; 271(25): 14916 - 14924. [Abstract] [Full Text] [PDF]
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K. A. Harrison and R. C. Murphy Isoleukotrienes Are Biologically Active Free Radical Products of Lipid Peroxidation J. Biol. Chem., July 21, 1995; 270(29): 17273 - 17278. [Abstract] [Full Text] [PDF]
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D. Pratico, J. A. Lawson, and G. A. FitzGerald Cylooxygenase-dependent Formation of the Isoprostane, 8-Epi Prostaglandin F[IMAGE] J. Biol. Chem., April 28, 1995; 270(17): 9800 - 9808. [Abstract] [Full Text] [PDF]
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E. A. Weinstein, H. Li, J. A. Lawson, J. Rokach, G. A. FitzGerald, and P. H. Axelsen Prothrombinase Acceleration by Oxidatively Damaged Phospholipids J. Biol. Chem., July 21, 2000; 275(30): 22925 - 22930. [Abstract] [Full Text] [PDF]
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N. Bernoud-Hubac, S. S. Davies, O. Boutaud, T. J. Montine, and L. J. Roberts II Formation of Highly Reactive gamma -Ketoaldehydes (Neuroketals) as Products of the Neuroprostane Pathway J. Biol. Chem., August 10, 2001; 276(33): 30964 - 30970. [Abstract] [Full Text] [PDF]
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