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Science 20 August 1999:
Vol. 285. no. 5431, pp. 1276 - 1279
DOI: 10.1126/science.285.5431.1276
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Reports

Anti-inflammatory Properties of Cytochrome P450 Epoxygenase-Derived Eicosanoids

Koichi Node, 1 Yuqing Huo, 2 Xiulu Ruan, 1 Baichun Yang, 3 Martin Spiecker, 1 Klaus Ley, 2 Darryl C. Zeldin, 3 James K. Liao 1*

The epoxyeicosatrienoic acids (EETs) are products of cytochrome P450 epoxygenases that have vasodilatory properties similar to that of endothelium-derived hyperpolarizing factor. The cytochrome P450 isoform CYP2J2 was cloned and identified as a potential source of EETs in human endothelial cells. Physiological concentrations of EETs or overexpression of CYP2J2 decreased cytokine-induced endothelial cell adhesion molecule expression, and EETs prevented leukocyte adhesion to the vascular wall by a mechanism involving inhibition of transcription factor NF-kappa B and Ikappa B kinase. The inhibitory effects of EETs were independent of their membrane-hyperpolarizing effects, suggesting that these molecules play an important nonvasodilatory role in vascular inflammation.

1 Vascular Medicine and Atherosclerosis Unit, Cardiovascular Division, Brigham and Women's Hospital and Harvard Medical School, 221 Longwood Avenue, LMRC-322, Boston, MA 02115, USA.
2 Department of Biomedical Engineering, University of Virginia Health Sciences Center, Charlottesville, VA 22908, USA.
3 Laboratory of Pulmonary Pathobiology, National Institute of Environmental Health Sciences, NIH, Research Triangle Park, NC 27709, USA.
*   To whom correspondence should be addressed. E-mail: jliao{at}rics.bwh.harvard.edu

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X. Fang, N. L. Weintraub, R. B. McCaw, S. Hu, S. D. Harmon, J. B. Rice, B. D. Hammock, and A. A. Spector (2004)
Am J Physiol Heart Circ Physiol 287, H2412-H2420
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Risk of Coronary Artery Disease Associated With Polymorphism of the Cytochrome P450 Epoxygenase CYP2J2.
M. Spiecker, H. Darius, T. Hankeln, M. Soufi, A. M. Sattler, J. R. Schaefer, K. Node, J. Borgel, A. Mugge, K. Lindpaintner, et al. (2004)
Circulation 110, 2132-2136
   Abstract »    Full Text »    PDF »
Molecular, Endocrine, and Genetic Mechanisms of Arterial Calcification.
T. M. Doherty, L. A. Fitzpatrick, D. Inoue, J.-H. Qiao, M. C. Fishbein, R. C. Detrano, P. K. Shah, and T. B. Rajavashisth (2004)
Endocr. Rev. 25, 629-672
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The mechanism of EDHF-mediated responses in subcutaneous small arteries from healthy pregnant women.
L. Luksha, H. Nisell, and K. Kublickiene (2004)
Am J Physiol Regulatory Integrative Comp Physiol 286, R1102-R1109
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Soluble Epoxide Hydrolase Inhibition Protects the Kidney from Hypertension-Induced Damage.
X. Zhao, T. Yamamoto, J. W. Newman, I.-H. Kim, T. Watanabe, B. D. Hammock, J. Stewart, J. S. Pollock, D. M. Pollock, and J. D. Imig (2004)
J. Am. Soc. Nephrol. 15, 1244-1253
   Abstract »    Full Text »    PDF »
Cloning, Expression, and Characterization of Three New Mouse Cytochrome P450 Enzymes and Partial Characterization of Their Fatty Acid Oxidation Activities.
H. Wang, Y. Zhao, J. A. Bradbury, J. P. Graves, J. Foley, J. A. Blaisdell, J. A. Goldstein, and D. C. Zeldin (2004)
Mol. Pharmacol. 65, 1148-1158
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Distribution of Soluble Epoxide Hydrolase and of Cytochrome P450 2C8, 2C9, and 2J2 in Human Tissues.
A. E. Enayetallah, R. A. French, M. S. Thibodeau, and D. F. Grant (2004)
J. Histochem. Cytochem. 52, 447-454
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CYP450 dietary inhibitors attenuate TNF-{alpha}-stimulated endothelial molecule expression and leukocyte adhesion.
M. Sasaki, J. W. Elrod, P. Jordan, M. Itoh, T. Joh, A. Minagar, and J. S. Alexander (2004)
Am J Physiol Cell Physiol 286, C931-C939
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Vascular localization of soluble epoxide hydrolase in the human kidney.
Z. Yu, B. B. Davis, C. Morisseau, B. D. Hammock, J. L. Olson, D. L. Kroetz, and R. H. Weiss (2004)
Am J Physiol Renal Physiol 286, F720-F726
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Membrane Potential-Dependent Inhibition of Platelet Adhesion to Endothelial Cells by Epoxyeicosatrienoic Acids.
F. Krotz, T. Riexinger, M. A. Buerkle, K. Nithipatikom, T. Gloe, H.-Y. Sohn, W. B. Campbell, and U. Pohl (2004)
Arterioscler. Thromb. Vasc. Biol. 24, 595-600
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ACE Inhibition and Bradykinin-Mediated Renal Vascular Responses: EDHF Involvement.
J. D. Imig (2004)
Hypertension 43, 533-535
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A Peroxisome Proliferator-Activated Receptor-{alpha} Activator Induces Renal CYP2C23 Activity and Protects from Angiotensin II-Induced Renal Injury.
D. N. Muller, J. Theuer, E. Shagdarsuren, E. Kaergel, H. Honeck, J.-K. Park, M. Markovic, E. Barbosa-Sicard, R. Dechend, M. Wellner, et al. (2004)
Am. J. Pathol. 164, 521-532
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Polymorphism of the Soluble Epoxide Hydrolase Is Associated With Coronary Artery Calcification in African-American Subjects: The Coronary Artery Risk Development In Young Adults (CARDIA) Study.
M. Fornage, E. Boerwinkle, P. A. Doris, D. Jacobs, K. Liu, and N. D. Wong (2004)
Circulation 109, 335-339
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Reduced Inflammation and Tissue Damage in Transgenic Rabbits Overexpressing 15-Lipoxygenase and Endogenous Anti-inflammatory Lipid Mediators.
C. N. Serhan, A. Jain, S. Marleau, C. Clish, A. Kantarci, B. Behbehani, S. P. Colgan, G. L. Stahl, A. Merched, N. A. Petasis, et al. (2003)
J. Immunol. 171, 6856-6865
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Involvement of CYP 2C9 in Mediating the Proinflammatory Effects of Linoleic Acid in Vascular Endothelial Cells.
S. Viswanathan, B. D. Hammock, J. W. Newman, P. Meerarani, M. Toborek, and B. Hennig (2003)
J. Am. Coll. Nutr. 22, 502-510
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Dyslipidemia, but Not Hyperglycemia, Induces Inflammatory Adhesion Molecules in Human Retinal Vascular Endothelial Cells.
W. Chen, D. B. Jump, M. B. Grant, W. J. Esselman, and J. V. Busik (2003)
Invest. Ophthalmol. Vis. Sci. 44, 5016-5022
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Up-Regulation of Endothelial Nitric-Oxide Synthase by Endothelium-Derived Hyperpolarizing Factor Involves Mitogen-Activated Protein Kinase and Protein Kinase C Signaling Pathways.
H. Wang, L. Lin, J. Jiang, Y. Wang, Z. Y. Lu, J. A. Bradbury, F. B. Lih, D. W. Wang, and D. C. Zeldin (2003)
J. Pharmacol. Exp. Ther. 307, 753-764
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Epoxyeicosatrienoic Acids Activate Transglutaminases in Situ and Induce Cornification of Epidermal Keratinocytes.
P. A. Ladd, L. Du, J. H. Capdevila, R. Mernaugh, and D. S. Keeney (2003)
J. Biol. Chem. 278, 35184-35192
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11,12-Epoxyeicosatrienoic Acid-induced Inhibition of FOXO Factors Promotes Endothelial Proliferation by Down-Regulating p27Kip1.
M. Potente, B. Fisslthaler, R. Busse, and I. Fleming (2003)
J. Biol. Chem. 278, 29619-29625
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Polymorphisms in Human Soluble Epoxide Hydrolase.
B. D. Przybyla-Zawislak, P. K. Srivastava, J. Vazquez-Matias, H. W. Mohrenweiser, J. E. Maxwell, B. D. Hammock, J. A. Bradbury, A. E. Enayetallah, D. C. Zeldin, and D. F. Grant (2003)
Mol. Pharmacol. 64, 482-490
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11,12-Epoxyeicosatrienoic Acid Attenuates Synthesis of Prostaglandin E2 in Rat Monocytes Stimulated with Lipopolysaccharide.
W. Kozak, D. M. Aronoff, O. Boutaud, and A. Kozak (2003)
Experimental Biology and Medicine 228, 786-794
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The soluble epoxide hydrolase encoded by EPXH2 is a bifunctional enzyme with novel lipid phosphate phosphatase activity.
J. W. Newman, C. Morisseau, T. R. Harris, and B. D. Hammock (2003)
PNAS 100, 1558-1563
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TNF-alpha -induced endothelial cell adhesion molecule expression is cytochrome P-450 monooxygenase dependent.
M. Sasaki, D. Ostanin, J. W. Elrod, T. Oshima, P. Jordan, M. Itoh, T. Joh, A. Minagar, and J. S. Alexander (2003)
Am J Physiol Cell Physiol 284, C422-C428
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Epoxygenase-driven angiogenesis in human lung microvascular endothelial cells.
M. Medhora, J. Daniels, K. Mundey, B. Fisslthaler, R. Busse, E. R. Jacobs, and D. R. Harder (2003)
Am J Physiol Heart Circ Physiol 284, H215-H224
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Human coronary endothelial cells convert 14,15-EET to a biologically active chain-shortened epoxide.
X. Fang, N. L. Weintraub, C. L. Oltman, L. L. Stoll, T. L. Kaduce, S. Harmon, K. C. Dellsperger, C. Morisseau, B. D. Hammock, and A. A. Spector (2002)
Am J Physiol Heart Circ Physiol 283, H2306-H2314
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