Involvement of CYP 2C9 in Mediating the Proinflammatory Effects of Linoleic Acid in Vascular Endothelial Cells

REFERENCES

• Behrendt D, Ganz P: Endothelial function. From vascular biology to clinical applications. Am J Cardiol90 :40L– 48L,2002 .
   PubMed Web of Science ®Google Scholar
• Sydow K, Schwedhelm E, Arakawa N, Bode-Boger SM, Tsikas D, Hornig B, Frolich JC, Boger RH: ADMA and oxidative stress are responsible for endothelial dysfunction in hyperhomocyst(e)inemia: effects of L-arginine and B vitamins. Cardiovasc Res57 :244– 252,2003 .
   PubMed Web of Science ®Google Scholar
• Landmesser U, Spiekermann S, Dikalov S, Tatge H, Wilke R, Kohler C, Harrison DG, Hornig B, Drexler H: Vascular oxidative stress and endothelial dysfunction in patients with chronic heart failure: role of xanthine-oxidase and extracellular superoxide dismutase. Circulation106 :3073– 3078,2002 .
   PubMed Web of Science ®Google Scholar
• Hennig B, Toborek M: Nutrition and endothelial cell function: Implications in Atherosclerosis. Nutr Res21 :279– 293,2001 .
   Web of Science ®Google Scholar
• Toborek M, Lee YW, Garrido R, Kaiser S, Hennig B: Unsaturated fatty acids selectively induce an inflammatory environment in human endothelial cells. Am J Clin Nutr75 :119– 125,2002 .
   PubMed Web of Science ®Google Scholar
• Hoebel BG, Steyrer E, Graier WF: Origin and function of epoxyeicosatrienoic acids in vascular endothelial cells: more than just endothelium-derived hyperpolarizing factor? Clin Exp Pharmacol Physiol25 :826– 830,1998 .
   PubMed Web of Science ®Google Scholar
• Roman RJ: P-450 metabolites of arachidonic acid in the control of cardiovascular function. Physiol Rev82 :131– 185,2002 .
   PubMed Web of Science ®Google Scholar
• Fleming I: Cytochrome p450 and vascular homeostasis. Circ Res89 :753– 762,2001 .
   PubMed Web of Science ®Google Scholar
• Fleming I, Michaelis UR, Bredenkotter D, Fisslthaler B, Dehghani F, Brandes RP, Busse R: Endothelium-derived hyperpolarizing factor synthase (Cytochrome P450 2C9) is a functionally significant source of reactive oxygen species in coronary arteries. Circ Res88 :44– 51,2001 .
   PubMed Web of Science ®Google Scholar
• Popp R, Fleming I, Busse R: Pulsatile stretch in coronary arteries elicits release of endothelium-derived hyperpolarizing factor: a modulator of arterial compliance. Circ Res82 :696– 703,1998 .
   PubMed Web of Science ®Google Scholar
• Draper AJ, Hammock BD: Identification of CYP2C9 as a human liver microsomal linoleic acid epoxygenase. Arch Biochem Biophys376 :199– 205,2000 .
   PubMed Web of Science ®Google Scholar
• Ishizaki T, Takahashi H, Ozawa T, Chang SW, Voelkel NF: Leukotoxin, 9,10-epoxy-12-octadecenoate causes pulmonary vasodilation in rats. Am J Physiol268 :L123– 128,1995 .
   PubMed Web of Science ®Google Scholar
• Reddy PS, Kumar TC, Reddy MN, Sarada C, Reddanna P: Differential formation of octadecadienoic acid and octadecatrienoic acid products in control and injured/infected potato tubers. Biochim Biophys Acta1483 :294– 300,2000 .
   PubMed Web of Science ®Google Scholar
• Fukushima A, Hayakawa M, Sugiyama S, Ajioka M, Ito T, Satake T, Ozawa T: Cardiovascular effects of leukotoxin (9, 10-epoxy-12-octadecenoate) and free fatty acids in dogs. Cardiovasc Res22 :213– 218,1988 .
   PubMed Web of Science ®Google Scholar
• Kosaka K, Suzuki K, Hayakawa M, Sugiyama S, Ozawa T: Leukotoxin, a linoleate epoxide: its implication in the late death of patients with extensive burns. Mol Cell Biochem139 :141– 148,1994 .
   PubMed Web of Science ®Google Scholar
• Ozawa T, Hayakawa M, Kosaka K, Sugiyama S, Ogawa T, Yokoo K, Aoyama H, Izawa Y: Leukotoxin, 9,10-epoxy-12-octadecenoate, as a burn toxin causing adult respiratory distress syndrome. Adv Prostaglandin Thromboxane Leukot Res21B :569– 572,1991 .
   PubMedGoogle Scholar
• Hennig B, Shasby DM, Fulton AB, Spector AA: Exposure to free fatty acid increases the transfer of albumin across cultured endothelial monolayers. Arteriosclerosis4 :489– 497,1984 .
   PubMedGoogle Scholar
• Toborek M, Lee YW, Kaiser S, Hennig B: Measurement of inflammatory properties of fatty acids in human endothelial cells. Methods Enzymol352 :198– 219,2002 .
   PubMed Web of Science ®Google Scholar
• Yang HW, Hwang KJ, Kwon HC, Kim HS, Choi KW, Oh KS: Detection of reactive oxygen species (ROS) and apoptosis in human fragmented embryos. Hum Reprod13 :998– 1002,1998 .
   PubMed Web of Science ®Google Scholar
• Baker MA, Cerniglia GJ, Zaman A: Microtiter plate assay for the measurement of glutathione and glutathione disulfide in large numbers of biological samples. Anal Biochem190 :360– 365,1990 .
   PubMed Web of Science ®Google Scholar
• Dignam JD, Lebovitz RM, Roeder RG: Accurate transcription initiation by RNA polymerase II in a soluble extract from isolated mammalian nuclei. Nucleic Acids Res11 :1475– 1489,1983 .
   PubMed Web of Science ®Google Scholar
• Newman JW, Watanabe T, Hammock BD: The simultaneous quantification of cytochrome P450 dependent linoleate and arachidonate metabolites in urine by HPLC-MS/MS. J Lipid Res43 :1563– 1578,2002 .
   PubMed Web of Science ®Google Scholar
• Munzel T, Afanas’ev IB, Kleschyov AL, Harrison DG: Detection of superoxide in vascular tissue. Arterioscler Thromb Vasc Biol22 :1761– 1768,2002 .
   PubMed Web of Science ®Google Scholar
• Benov L, Sztejnberg L, Fridovich I: Critical evaluation of the use of hydroethidine as a measure of superoxide anion radical. Free Radic Biol Med25 :826– 831,1998 .
   PubMed Web of Science ®Google Scholar
• Oyekan AO, McAward K, Conetta J, Rosenfeld L, McGiff JC: Endothelin-1 and CYP450 arachidonate metabolites interact to promote tissue injury in DOCA-salt hypertension. Am J Physiol276 :R766– 775,1999 .
   PubMed Web of Science ®Google Scholar
• Scarborough PE, Ma J, Qu W, Zeldin DC: P450 subfamily CYP2J and their role in the bioactivation of arachidonic acid in extrahepatic tissues. Drug Metab Rev31 :205– 234,1999 .
   PubMed Web of Science ®Google Scholar
• Wu S, Moomaw CR, Tomer KB, Falck JR, Zeldin DC: Molecular cloning and expression of CYP2J2, a human cytochrome P450 arachidonic acid epoxygenase highly expressed in heart. J Biol Chem271 :3460– 3468,1996 .
   PubMed Web of Science ®Google Scholar
• Bauersachs J, Christ M, Ertl G, Michaelis UR, Fisslthaler B, Busse R, Fleming I: Cytochrome P450 2C expression and EDHF-mediated relaxation in porcine coronary arteries is increased by cortisol. Cardiovasc Res54 :669– 675,2002 .
   PubMed Web of Science ®Google Scholar
• Bylund J, Ericsson J, Oliw EH: Analysis of cytochrome P450 metabolites of arachidonic and linoleic acids by liquid chromatography-mass spectrometry with ion trap MS. Anal Biochem265 :55– 68,1998 .
   PubMed Web of Science ®Google Scholar
• Bylund J, Kunz T, Valmsen K, Oliw EH: Cytochromes P450 with bisallylic hydroxylation activity on arachidonic and linoleic acids studied with human recombinant enzymes and with human and rat liver microsomes. J Pharmacol Exp Ther284 :51– 60,1998 .
   PubMed Web of Science ®Google Scholar
• Capdevila JH, Dishman E, Karara A, Falck JR: Cytochrome P450 arachidonic acid epoxygenase: stereochemical characterization of epoxyeicosatrienoic acids. Methods Enzymol206 :441– 453,1991 .
   PubMed Web of Science ®Google Scholar
• Oliw EH, Bylund J, Herman C: Bisallylic hydroxylation and epoxidation of polyunsaturated fatty acids by cytochrome P450. Lipids31 :1003– 1021,1996 .
   PubMed Web of Science ®Google Scholar
• Zeldin DC, DuBois RN, Falck JR, Capdevila JH: Molecular cloning, expression and characterization of an endogenous human cytochrome P450 arachidonic acid epoxygenase isoform. Arch Biochem Biophys322 :76– 86,1995 .
   PubMed Web of Science ®Google Scholar
• Puntarulo S, Cederbaum AI: Production of reactive oxygen species by microsomes enriched in specific human cytochrome P450 enzymes. Free Radic Biol Med24 :1324– 1330,1998 .
   PubMed Web of Science ®Google Scholar
• Dai Y, Rashba-Step J, Cederbaum AI: Stable expression of human cytochrome P4502E1 in HepG2 cells: characterization of catalytic activities and production of reactive oxygen intermediates. Biochemistry32 :6928– 6937,1993 .
   PubMed Web of Science ®Google Scholar
• Park JY, Shigenaga MK, Ames BN: Induction of cytochrome P4501A1 by 2,3,7,8-tetrachlorodibenzo-p-dioxin or indolo(3,2-b)carbazole is associated with oxidative DNA damage. Proc Natl Acad Sci U S A93 :2322– 2327,1996 .
   PubMed Web of Science ®Google Scholar
• White RE, Coon MJ: Oxygen activation by cytochrome P-450. Annu Rev Biochem49 :315– 356,1980 .
   PubMed Web of Science ®Google Scholar
• Porter TD, Coon MJ. Cytochrome P-450: Multiplicity of isoforms, substrates, and catalytic and regulatory mechanisms. J Biol Chem266 :13469– 13472,1991 .
   PubMed Web of Science ®Google Scholar
• Davydov DR: Microsomal monooxygenase in apoptosis: another target for cytochrome c signaling? Trends Biochem Sci26 :155– 160,2001 .
   PubMed Web of Science ®Google Scholar
• Sun Y, Zhang J, Lu L, Chen SS, Quinn MT, Weber KT: Aldosterone-induced inflammation in the rat heart : role of oxidative stress. Am J Pathol161 :1773– 1781,2002 .
   PubMed Web of Science ®Google Scholar
• Altavilla D, Deodato B, Campo GM, Arlotta M, Miano M, Squadrito G, Saitta A, Cucinotta D, Ceccarelli S, Ferlito M, Tringali M, Minutoli L, Caputi AP, Squadrito F: IRFI 042, a novel dual vitamin E-like antioxidant, inhibits activation of nuclear factor-kappaB and reduces the inflammatory response in myocardial ischemia-reperfusion injury. Cardiovasc Res47 :515– 528,2000 .
   PubMed Web of Science ®Google Scholar
• Woo Lee Y, Joo PH, Hennig B, Toborek M: Linoleic acid induces MCP-1 gene expression in human microvascular endothelial cells through an oxidative mechanism. J Nutr Biochem12 :648– 654,2001 .
   PubMed Web of Science ®Google Scholar
• Herbst U, Toborek M, Kaiser S, Mattson MP, Hennig B: 4-Hydroxynonenal induces dysfunction and apoptosis of cultured endothelial cells. J Cell Physiol181 :295– 303,1999 .
   PubMed Web of Science ®Google Scholar
• Hennig B, Toborek M, Joshi-Barve S, Barger SW, Barve S, Mattson MP, McClain CJ: Linoleic acid activates nuclear transcription factor-kappa B (NF-kappa B) and induces NF-kappa B-dependent transcription in cultured endothelial cells. Am J Clin Nutr63 :322– 328,1996 .
   PubMed Web of Science ®Google Scholar
• Park SH, Park JH, Kang JS, Kang YH: Involvement of transcription factors in plasma HDL protection against TNF-alpha-induced vascular cell adhesion molecule-1 expression. Int J Biochem Cell Biol35 :168– 182,2003 .
   PubMed Web of Science ®Google Scholar
• Eyries M, Agrapart M, Alonso A, Soubrier F: Phorbol ester induction of angiotensin-converting enzyme transcription is mediated by Egr-1 and AP-1 in human endothelial cells via ERK1/2 pathway. Circ Res91 :899– 906,2002 .
   PubMed Web of Science ®Google Scholar
• Akai M, Ishizaki T, Matsukawa S, Shigemori K, Miyamori I: Leukotoxin (9, 10-epoxy-12-octadecenoate) impairs energy and redox state of isolated perfused rat lung. Free Radic Biol Med25 :596– 604,1998 .
   PubMed Web of Science ®Google Scholar
• Ozawa T, Sugiyama S, Hayakawa M, Satake T, Taki F, Iwata M, Taki K: Existence of leukotoxin 9,10-epoxy-12-octadecenoate in lung lavages from rats breathing pure oxygen and from patients with the adult respiratory distress syndrome. Am Rev Respir Dis137 :535– 540,1988 .
   PubMed Web of Science ®Google Scholar
• Moran JH, Mitchell LA, Bradbury JA, Qu W, Zeldin DC, Schnellmann RG, Grant DF: Analysis of the cytotoxic properties of linoleic acid metabolites produced by renal and hepatic P450s. Toxicol Appl Pharmacol168 :268– 279,2000 .
   PubMed Web of Science ®Google Scholar
• Haastrup A, Gadegbeku CA, Zhang D, Mukhin YV, Greene EL, Jaffa AA, Egan BM: Lipids stimulate the production of 6-keto-prostaglandin f(1alpha) in human dorsal hand veins. Hypertension38 :858– 863,2001 .
   PubMed Web of Science ®Google Scholar
• Nakanishi M, Ishizaki T, Demura Y, Okamura S, Ameshima S, Sasaki F, Matsukawa S, Miyamori I: Leukotoxin, 9,10-epoxy-12-octadecenoate, causes pulmonary vasodilation by stimulation of vascular eNOS and iNOS. Lung178 :137– 148,2000 .
   PubMed Web of Science ®Google Scholar
• Node K, Huo Y, Ruan X, Yang B, Spiecker M, Ley K, Zeldin DC, Liao JK: Anti-inflammatory properties of cytochrome P450 epoxygenase-derived eicosanoids. Science285 :1276– 1279,1999 .
   PubMed Web of Science ®Google Scholar