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Volumn 34, Issue 8, 2006, Pages 1376-1385

Induction of CYP1A and CYP2-mediated arachidonic acid epoxygenation and suppression of 20-hydroxyeicosatetraenoic acid by imidazole derivatives including the aromatase Inhibitor vorozole

Author keywords

[No Author keywords available]

Indexed keywords

1 BENZYLIMIDAZOLE; 2,3,7,8 TETRACHLORODIBENZO PARA DIOXIN; 20 HYDROXYICOSATETRAENOIC ACID; ALBENDAZOLE; ANTHELMINTIC AGENT; ARACHIDONIC ACID; AROMATASE; AROMATASE INHIBITOR; CYTOCHROME P450 1A; CYTOCHROME P450 2A; ICOSATRIENOIC ACID; IMIDAZOLE DERIVATIVE; MEMBRANE LIPID; OMEPRAZOLE; PHENOBARBITAL; PROTON PUMP INHIBITOR; THROMBOXANE SYNTHASE INHIBITOR; TIABENDAZOLE; VOROZOLE;

EID: 33746049226     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.106.009498     Document Type: Article
Times cited : (26)

References (46)
  • 3
    • 0033993749 scopus 로고    scopus 로고
    • Cytochrome P450 and arachidonic acid bioactivation. Molecular and functional properties of the arachidonate monooxygenase
    • Capdevila JH, Falck JR, and Harris RC (2000) Cytochrome P450 and arachidonic acid bioactivation. Molecular and functional properties of the arachidonate monooxygenase. J Lipid Res 41:163-181.
    • (2000) J Lipid Res , vol.41 , pp. 163-181
    • Capdevila, J.H.1    Falck, J.R.2    Harris, R.C.3
  • 4
    • 0025311273 scopus 로고
    • Cytochrome P-450 enzyme-specific control of the regio- and enantiofacial selectivity of the microsomal arachidonic acid epoxygenase
    • Capdevila JH, Karara A, Waxman DJ, Martin MV, Falck JR, and Guenguerich FP (1990b) Cytochrome P-450 enzyme-specific control of the regio- and enantiofacial selectivity of the microsomal arachidonic acid epoxygenase. J Biol Chem 265:10865-10871.
    • (1990) J Biol Chem , vol.265 , pp. 10865-10871
    • Capdevila, J.H.1    Karara, A.2    Waxman, D.J.3    Martin, M.V.4    Falck, J.R.5    Guenguerich, F.P.6
  • 8
    • 0027940480 scopus 로고
    • Regio- And stereoselective epoxidation of arachidonic acid by human cytochromes P450 2C8 and 2C9
    • Daikh BE, Lasker JM, Raucy JL, and Koop DR (1994) Regio- and stereoselective epoxidation of arachidonic acid by human cytochromes P450 2C8 and 2C9. J Pharmacol Exp Ther 271:1427-1433.
    • (1994) J Pharmacol Exp Ther , vol.271 , pp. 1427-1433
    • Daikh, B.E.1    Lasker, J.M.2    Raucy, J.L.3    Koop, D.R.4
  • 10
    • 33746790148 scopus 로고    scopus 로고
    • Protective effects of epoxyeicosatrienoic acids (EETs) on human endothelial cells from the pulmonary and coronary vasculature
    • in press
    • Dhanasekaran A, Al-Saghir R, Lopez B, Zhu D, Gutterman DD, Jacobs ER, and Medhora MM (2006) Protective effects of epoxyeicosatrienoic acids (EETs) on human endothelial cells from the pulmonary and coronary vasculature. Am J Physiol, in press.
    • (2006) Am J Physiol
    • Dhanasekaran, A.1    Al-Saghir, R.2    Lopez, B.3    Zhu, D.4    Gutterman, D.D.5    Jacobs, E.R.6    Medhora, M.M.7
  • 11
    • 33144477599 scopus 로고    scopus 로고
    • Sunlight generates multiple tryptophan photoproducts eliciting high efficacy CYP1A induction in chick hepatocytes and in vivo
    • Diani-Moore S, Labitzke E, Brown R, Garvin A, Wong L, and Rifkind AB (2006) Sunlight generates multiple tryptophan photoproducts eliciting high efficacy CYP1A induction in chick hepatocytes and in vivo. Toxicol Sci 90:96-110.
    • (2006) Toxicol Sci , vol.90 , pp. 96-110
    • Diani-Moore, S.1    Labitzke, E.2    Brown, R.3    Garvin, A.4    Wong, L.5    Rifkind, A.B.6
  • 12
    • 0037478407 scopus 로고    scopus 로고
    • Human extrahepatic cytochromes P450: Function in xenobiotic metabolism and tissue-selective chemical toxicity in the respiratory and gastrointestinal tracts
    • Ding X and Kaminsky LS (2003) Human extrahepatic cytochromes P450: function in xenobiotic metabolism and tissue-selective chemical toxicity in the respiratory and gastrointestinal tracts. Annu Rev Pharmacol Toxicol 43:149-173.
    • (2003) Annu Rev Pharmacol Toxicol , vol.43 , pp. 149-173
    • Ding, X.1    Kaminsky, L.S.2
  • 14
    • 12644271134 scopus 로고    scopus 로고
    • Molecular cloning and expression of two novel avian cytochrome P450 1A enzymes induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin
    • Gilday D, Gannon M, Yutzey K, Bader D, and Rifkind AB (1996) Molecular cloning and expression of two novel avian cytochrome P450 1A enzymes induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin. J Biol Chem 271:33054-33059.
    • (1996) J Biol Chem , vol.271 , pp. 33054-33059
    • Gilday, D.1    Gannon, M.2    Yutzey, K.3    Bader, D.4    Rifkind, A.B.5
  • 15
    • 0031782776 scopus 로고    scopus 로고
    • Pre-clinical and clinical review of vorozole, a new third generation aromatase inhibitor
    • Goss PE (1998) Pre-clinical and clinical review of vorozole, a new third generation aromatase inhibitor. Breast Cancer Res Treat 49 (Suppl 1):S59-S65; discussion S73-S57.
    • (1998) Breast Cancer Res Treat , vol.49 , Issue.1 SUPPL.
    • Goss, P.E.1
  • 17
    • 0024558469 scopus 로고
    • Sequence of a chicken phenobarbital-inducible cytochrome P450 cDNA: Regulation of two P450 mRNAs transcribed from different genes
    • Hansen AJ, May BK, and Elferink LA (1989) Sequence of a chicken phenobarbital-inducible cytochrome P450 cDNA: regulation of two P450 mRNAs transcribed from different genes. DNA 8:179-191.
    • (1989) DNA , vol.8 , pp. 179-191
    • Hansen, A.J.1    May, B.K.2    Elferink, L.A.3
  • 18
    • 0027051590 scopus 로고
    • Immunochemical identity of the 2,3,7,8-tetrachlorodibenzo-p-dioxin- And beta-naphthoflavone-induced cytochrome P-450 arachidonic acid epoxygenases in chick embryo liver: Distinction from the omega-hydroxylase and the phenobarbital-induced epoxygenase
    • Kanetoshi A, Ward AM, May BK, and Rifkind AB (1992) Immunochemical identity of the 2,3,7,8-tetrachlorodibenzo-p-dioxin- and beta-naphthoflavone- induced cytochrome P-450 arachidonic acid epoxygenases in chick embryo liver: distinction from the omega-hydroxylase and the phenobarbital-induced epoxygenase. Mol Pharmacol 42:1020-1026.
    • (1992) Mol Pharmacol , vol.42 , pp. 1020-1026
    • Kanetoshi, A.1    Ward, A.M.2    May, B.K.3    Rifkind, A.B.4
  • 19
    • 0030588279 scopus 로고    scopus 로고
    • Differences in inducibility of CYP1A1-mRNA by benzimidazole compounds between human and mouse cells: Evidences of a human-specific signal transduction pathway for CYP1A1 induction
    • Kikuchi H, Kato H, Mizuno M, Hossain A, Ikawa S, Miyazaki J, and Watanabe M (1996) Differences in inducibility of CYP1A1-mRNA by benzimidazole compounds between human and mouse cells: evidences of a human-specific signal transduction pathway for CYP1A1 induction. Arch Biochem Biophys 334:235-240.
    • (1996) Arch Biochem Biophys , vol.334 , pp. 235-240
    • Kikuchi, H.1    Kato, H.2    Mizuno, M.3    Hossain, A.4    Ikawa, S.5    Miyazaki, J.6    Watanabe, M.7
  • 20
    • 13844309746 scopus 로고    scopus 로고
    • Regulation and inhibition of arachidonic acid omega-hydroxylases and 20-HETE formation
    • Kroetz DL and Xu F (2005) Regulation and inhibition of arachidonic acid omega-hydroxylases and 20-HETE formation. Annu Rev Pharmacol Toxicol 45:413-438.
    • (2005) Annu Rev Pharmacol Toxicol , vol.45 , pp. 413-438
    • Kroetz, D.L.1    Xu, F.2
  • 21
    • 0014949207 scopus 로고
    • Cleavage of structural proteins during the assembly of the head of bacteriophage T4
    • Laemmli UK (1970) Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature (Lond) 227:680-685.
    • (1970) Nature (Lond) , vol.227 , pp. 680-685
    • Laemmli, U.K.1
  • 22
    • 0028283819 scopus 로고
    • Epoxidation of arachidonic acid as an active-site probe of cytochrome P-450 2B isoforms
    • Laethem RM, Halpert JR, and Koop DR (1994) Epoxidation of arachidonic acid as an active-site probe of cytochrome P-450 2B isoforms. Biochim Biophys Acta 1206:42-48.
    • (1994) Biochim Biophys Acta , vol.1206 , pp. 42-48
    • Laethem, R.M.1    Halpert, J.R.2    Koop, D.R.3
  • 23
    • 0032210679 scopus 로고    scopus 로고
    • 2,3,7,8-Tetrachlorodibenzo-pdioxin induction of cytochrome P450-dependent arachidonic acid metabolism in mouse liver microsomes: Evidence for species-specific differences in responses
    • Lee CA, Lawrence BP, Kerkvliet NI, and Rifkind AB (1998) 2,3,7,8-Tetrachlorodibenzo-pdioxin induction of cytochrome P450-dependent arachidonic acid metabolism in mouse liver microsomes: evidence for species-specific differences in responses. Toxicol Appl Pharmacol 153:1-11.
    • (1998) Toxicol Appl Pharmacol , vol.153 , pp. 1-11
    • Lee, C.A.1    Lawrence, B.P.2    Kerkvliet, N.I.3    Rifkind, A.B.4
  • 26
    • 0030958555 scopus 로고    scopus 로고
    • Effects of pantoprazole on xenobiotic metabolizing enzymes in rat liver microsomes: A comparison with other proton pump inhibitors
    • Masubuchi N, Hakusui H, and Okazaki O (1997) Effects of pantoprazole on xenobiotic metabolizing enzymes in rat liver microsomes: a comparison with other proton pump inhibitors. Drug Metab Dispos 25:584-589.
    • (1997) Drug Metab Dispos , vol.25 , pp. 584-589
    • Masubuchi, N.1    Hakusui, H.2    Okazaki, O.3
  • 27
    • 0037387681 scopus 로고    scopus 로고
    • Cytochrome P450 2C9-derived epoxyeicosatrienoic acids induce angiogenesis via cross-talk with the epidermal growth factor receptor (EGFR)
    • Michaelis UR, Fisslthaler B, Medhora M, Harder D, Fleming I, and Busse R (2003) Cytochrome P450 2C9-derived epoxyeicosatrienoic acids induce angiogenesis via cross-talk with the epidermal growth factor receptor (EGFR). FASEB J 17:770-772.
    • (2003) FASEB J , vol.17 , pp. 770-772
    • Michaelis, U.R.1    Fisslthaler, B.2    Medhora, M.3    Harder, D.4    Fleming, I.5    Busse, R.6
  • 28
    • 0026672670 scopus 로고
    • Beta-naphthoflavone induction of a cytochrome P-450 arachidonic acid epoxygenase in chick embryo liver distinct from the aryl hydrocarbon hydroxylase and from phenobarbital-induced arachidonate epoxygenase
    • Nakai K, Ward AM, Gannon M, and Rifkind AB (1992) Beta-naphthoflavone induction of a cytochrome P-450 arachidonic acid epoxygenase in chick embryo liver distinct from the aryl hydrocarbon hydroxylase and from phenobarbital-induced arachidonate epoxygenase. J Biol Chem 267:19503-19512.
    • (1992) J Biol Chem , vol.267 , pp. 19503-19512
    • Nakai, K.1    Ward, A.M.2    Gannon, M.3    Rifkind, A.B.4
  • 29
    • 2642510760 scopus 로고    scopus 로고
    • Role of aryl hydrocarbon receptor-mediated induction of the CYP1 enzymes in environmental toxicity and cancer
    • Nebert DW, Dalton TP, Okey AB, and Gonzalez FJ (2004) Role of aryl hydrocarbon receptor-mediated induction of the CYP1 enzymes in environmental toxicity and cancer. J Biol Chem 279:23847-23850.
    • (2004) J Biol Chem , vol.279 , pp. 23847-23850
    • Nebert, D.W.1    Dalton, T.P.2    Okey, A.B.3    Gonzalez, F.J.4
  • 30
    • 0035337058 scopus 로고    scopus 로고
    • Determination of cytochrome P450 metabolites of arachidonic acid in coronary venous plasma during ischemia and reperfusion in dogs
    • Nithipatikom K, DiCamelli RF, Kohler S, Gumina RJ, Falck JR, Campbell WB, and Gross GJ (2001) Determination of cytochrome P450 metabolites of arachidonic acid in coronary venous plasma during ischemia and reperfusion in dogs. Anal Biochem 292:115-124.
    • (2001) Anal Biochem , vol.292 , pp. 115-124
    • Nithipatikom, K.1    DiCamelli, R.F.2    Kohler, S.3    Gumina, R.J.4    Falck, J.R.5    Campbell, W.B.6    Gross, G.J.7
  • 32
    • 33746829910 scopus 로고    scopus 로고
    • Epoxyeicosatrienoic acids (EETs) in cardioprotection: Ischemic versus reperfusion injury
    • in press
    • Nithipatikom K, Moore JM, Isbell MA, Falck JR, and Gross GJ (2006) Epoxyeicosatrienoic acids (EETs) in cardioprotection: Ischemic versus reperfusion injury. Am J Physiol, in press.
    • (2006) Am J Physiol
    • Nithipatikom, K.1    Moore, J.M.2    Isbell, M.A.3    Falck, J.R.4    Gross, G.J.5
  • 33
    • 50449100139 scopus 로고
    • The carbon monoxide-binding pigment of liver microsomes. II. Solubilization, purification, and properties
    • Omura T and Sato R (1964) The carbon monoxide-binding pigment of liver microsomes. II. Solubilization, purification, and properties. J Biol Chem 239:2379-2385.
    • (1964) J Biol Chem , vol.239 , pp. 2379-2385
    • Omura, T.1    Sato, R.2
  • 34
    • 0023951398 scopus 로고
    • N-benzylimidazole, a high magnitude inducer of rat hepatic cytochrome P-450 exhibiting both polycyclic aromatic hydrocarbon- And phenobarbital-type induction of phase I and phase II drug-metabolizing enzymes
    • Papac DI and Franklin MR (1988) N-benzylimidazole, a high magnitude inducer of rat hepatic cytochrome P-450 exhibiting both polycyclic aromatic hydrocarbon- and phenobarbital-type induction of phase I and phase II drug-metabolizing enzymes. Drug Metab Dispos 16:259-264.
    • (1988) Drug Metab Dispos , vol.16 , pp. 259-264
    • Papac, D.I.1    Franklin, M.R.2
  • 35
    • 22844446840 scopus 로고    scopus 로고
    • Characterization of 5,6- And 8,9-epoxyeicosatrienoic acids (5,6- and 8,9-EET) as potent in vivo angiogenic lipids
    • Pozzi A, Macias-Perez I, Abair T, Wei S, Su Y, Zent R, Falck JR, and Capdevila JH (2005) Characterization of 5,6- and 8,9-epoxyeicosatrienoic acids (5,6- and 8,9-EET) as potent in vivo angiogenic lipids. J Biol Chem 280:27138-27146.
    • (2005) J Biol Chem , vol.280 , pp. 27138-27146
    • Pozzi, A.1    Macias-Perez, I.2    Abair, T.3    Wei, S.4    Su, Y.5    Zent, R.6    Falck, J.R.7    Capdevila, J.H.8
  • 37
    • 0029950230 scopus 로고    scopus 로고
    • Structural requirements for the induction of cytochromes P450 by benzimidazole anthelmintic derivatives in cultured rabbit hepatocytes
    • Rey-Grobellet X, Ferre N, Eeckhoutte C, Larrieu G, Pineau T, and Galtier P (1996) Structural requirements for the induction of cytochromes P450 by benzimidazole anthelmintic derivatives in cultured rabbit hepatocytes. Biochem Biophys Res Commun 220:789-794.
    • (1996) Biochem Biophys Res Commun , vol.220 , pp. 789-794
    • Rey-Grobellet, X.1    Ferre, N.2    Eeckhoutte, C.3    Larrieu, G.4    Pineau, T.5    Galtier, P.6
  • 38
    • 0028071185 scopus 로고
    • Purification and biochemical characterization of two major cytochrome P-450 isoforms induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin in chick embryo liver
    • Rifkind AB, Kanetoshi A, Orlinick J, Capdevila JH, and Lee C (1994) Purification and biochemical characterization of two major cytochrome P-450 isoforms induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin in chick embryo liver. J Biol Chem 269:3387-3396.
    • (1994) J Biol Chem , vol.269 , pp. 3387-3396
    • Rifkind, A.B.1    Kanetoshi, A.2    Orlinick, J.3    Capdevila, J.H.4    Lee, C.5
  • 39
    • 0029039791 scopus 로고
    • Arachidonic acid metabolism by human cytochrome P450s 2C8, 2C9, 2E1, and 1A2: Regioselective oxygenation and evidence for a role for CYP2C enzymes in arachidonic acid epoxygenation in human liver microsomes
    • Rifkind AB, Lee C, Chang TK, and Waxman DJ (1995) Arachidonic acid metabolism by human cytochrome P450s 2C8, 2C9, 2E1, and 1A2: regioselective oxygenation and evidence for a role for CYP2C enzymes in arachidonic acid epoxygenation in human liver microsomes. Arch Biochem Biophys 320:380-389.
    • (1995) Arch Biochem Biophys , vol.320 , pp. 380-389
    • Rifkind, A.B.1    Lee, C.2    Chang, T.K.3    Waxman, D.J.4
  • 40
    • 0036080081 scopus 로고    scopus 로고
    • P-450 metabolites of arachidonic acid in the control of cardiovascular function
    • Roman RJ (2002) P-450 metabolites of arachidonic acid in the control of cardiovascular function. Physiol Rev 82:131-185.
    • (2002) Physiol Rev , vol.82 , pp. 131-185
    • Roman, R.J.1
  • 41
    • 4444236138 scopus 로고    scopus 로고
    • Enhanced postischemic functional recovery in CYP2J2 transgenic hearts involves mitochondrial ATP-sensitive K+ channels and p42/p44 MAPK pathway
    • Seubert J, Yang B, Bradbury JA, Graves J, Degraff LM, Gabel S, Gooch R, Foley J, Newman J, Mao L, et al. (2004) Enhanced postischemic functional recovery in CYP2J2 transgenic hearts involves mitochondrial ATP-sensitive K+ channels and p42/p44 MAPK pathway. Circ Res 95:506-514.
    • (2004) Circ Res , vol.95 , pp. 506-514
    • Seubert, J.1    Yang, B.2    Bradbury, J.A.3    Graves, J.4    Degraff, L.M.5    Gabel, S.6    Gooch, R.7    Foley, J.8    Newman, J.9    Mao, L.10
  • 42
    • 0023870683 scopus 로고
    • Inducing effect of albendazole on rat liver drug-metabolizing enzymes and metabolite pharmacokinetics
    • Souhaili-el Amri H, Fargetton X, Benoit E, Totis M, and Batt AM (1988) Inducing effect of albendazole on rat liver drug-metabolizing enzymes and metabolite pharmacokinetics. Toxicol Appl Pharmacol 92:141-149.
    • (1988) Toxicol Appl Pharmacol , vol.92 , pp. 141-149
    • Souhaili-el Amri, H.1    Fargetton, X.2    Benoit, E.3    Totis, M.4    Batt, A.M.5
  • 43
    • 29544438187 scopus 로고    scopus 로고
    • Aromatase inhibitors - A triumph of translational oncology
    • Swain SM (2005) Aromatase inhibitors - a triumph of translational oncology. N Engl J Med 353:2807-2809.
    • (2005) N Engl J Med , vol.353 , pp. 2807-2809
    • Swain, S.M.1
  • 44
    • 22944448688 scopus 로고    scopus 로고
    • Arachidonic acid epoxygenase metabolites stimulate endothelial cell growth and angiogenesis via mitogen-activated protein kinase and phosphatidylinositol 3-kinase/Akt signaling pathways
    • Wang Y, Wei X, Xiao X, Hui R, Card JW, Carey MA, Wang DW, and Zeldin DC (2005) Arachidonic acid epoxygenase metabolites stimulate endothelial cell growth and angiogenesis via mitogen-activated protein kinase and phosphatidylinositol 3-kinase/Akt signaling pathways. J Pharmacol Exp Ther 314:522-532.
    • (2005) J Pharmacol Exp Ther , vol.314 , pp. 522-532
    • Wang, Y.1    Wei, X.2    Xiao, X.3    Hui, R.4    Card, J.W.5    Carey, M.A.6    Wang, D.W.7    Zeldin, D.C.8


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