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Vol. 284, Issue 3, 966-973, March 1998
Department of Pharmacology (M-H.W., E.B-S., B.A.Z., X.N., M.L.S.),
New York Medical College, Valhalla, New York, and Departments of
Biochemistry and Pharmacology (J.R.F., N.B.), University of Texas
Southwestern Medical Center, Dallas, Texas
We characterized the inhibitory activity of several acetylenic and
olefinic compounds on cytochrome P450 (CYP)-derived arachidonic acid
-hydroxylation and epoxidation using rat renal cortical microsomes
and recombinant CYP proteins. Among the acetylenic compounds,
6-(2-propargyloxyphenyl)hexanoic acid (PPOH) and
N-methylsulfonyl-6-(2-propargyloxyphenyl)hexanamide were found to be
potent and selective inhibitors of microsomal epoxidation with
IC50 values of 9 and 13 µM, respectively. On the other
hand, 17-octadecynoic acid inhibited both -hydroxylation and
epoxidation of arachidonic acid with IC50 values of 7 and 5 µM, respectively. The olefinic compounds
N-methylsulfonyl-12,12-dibromododec-11-enamide (DDMS) and
12,12-dibromododec-11-enoic acid (DBDD) exhibited a high degree of
selectivity inhibiting microsomal -hydroxylation with an
IC50 value of 2 µM, whereas the IC50 values
for epoxidation were 60 and 51 µM for DDMS and DBDD, respectively.
Studies using recombinant rat CYP4A isoforms showed that PPOH caused a
concentration-dependent inhibition of -hydroxylation and
11,12-epoxidation by CYP4A3 or CYP4A2 but had no effect on
CYP4A1-catalyzed -hydroxylase activity. On the other hand, DDMS
inhibited both CYP4A1- and CYP4A3- or CYP4A2-catalyzed arachidonic acid
oxidations. Inhibition of microsomal activity by PPOH, but not DDMS,
was time- and NADPH-dependent, a result characteristic of a
mechanism-based irreversible inhibitor. These studies provide
information useful for evaluating the role of the CYP-derived
arachidonic acid metabolites in the regulation of renal function and
blood pressure.
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C. Sauvant, H. Holzinger, and M. Gekle Short-Term Regulation of Basolateral Organic Anion Uptake in Proximal Tubular OK cells: EGF Acts via MAPK, PLA2, and COX1 J. Am. Soc. Nephrol., August 1, 2002; 13(8): 1981 - 1991. [Abstract] [Full Text] [PDF]
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F. A. Sylvester, D. W. Stepp, J. C. Frisbee, and J. H. Lombard High-salt diet depresses acetylcholine reactivity proximal to NOS activation in cerebral arteries Am J Physiol Heart Circ Physiol, July 1, 2002; 283(1): H353 - H363. [Abstract] [Full Text] [PDF]
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 T. Horiuchi, H. H. Dietrich, K. Hongo, T. Goto, and R. G. Dacey Jr Role of Endothelial Nitric Oxide and Smooth Muscle Potassium Channels in Cerebral Arteriolar Dilation in Response to Acidosis Stroke, March 1, 2002; 33(3): 844 - 849. [Abstract] [Full Text] [PDF]
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 R. J. Roman P-450 Metabolites of Arachidonic Acid in the Control of Cardiovascular Function Physiol Rev, January 1, 2002; 82(1): 131 - 185. [Abstract] [Full Text] [PDF]
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F. Zhang, M.-H. Wang, U.M. Krishna, J. R. Falck, M. Laniado-Schwartzman, and A. Nasjletti Modulation by 20-HETE of Phenylephrine-Induced Mesenteric Artery Contraction in Spontaneously Hypertensive and Wistar-Kyoto Rats Hypertension, December 1, 2001; 38(6): 1311 - 1315. [Abstract] [Full Text] [PDF]
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E. T. Morgan, V. Ullrich, A. Daiber, P. Schmidt, N. Takaya, H. Shoun, J. C. McGiff, A. Oyekan, C. J. Hanke, W. B. Campbell, et al. Cytochromes P450 and Flavin Monooxygenases---Targets and Sources of Nitric Oxide Drug Metab. Dispos., November 1, 2001; 29(11): 1366 - 1376. [Abstract] [Full Text] [PDF]
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X. Zhao, E. W. Inscho, M. Bondlela, J. R. Falck, and J. D. Imig The CYP450 hydroxylase pathway contributes to P2X receptor-mediated afferent arteriolar vasoconstriction Am J Physiol Heart Circ Physiol, November 1, 2001; 281(5): H2089 - H2096. [Abstract] [Full Text] [PDF]
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I. Fleming Cytochrome P450 and Vascular Homeostasis Circ. Res., October 26, 2001; 89(9): 753 - 762. [Abstract] [Full Text] [PDF]
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 R.-M. Gu, Y. Wei, J. R. Falck, U. M. Krishna, and W.-H. Wang Effects of protein tyrosine kinase and protein tyrosine phosphatase on apical K+ channels in the TAL Am J Physiol Cell Physiol, October 1, 2001; 281(4): C1188 - C1195. [Abstract] [Full Text] [PDF]
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Y. Wu, A. Huang, D. Sun, J. R. Falck, A. Koller, and G. Kaley Gender-specific compensation for the lack of NO in the mediation of flow-induced arteriolar dilation Am J Physiol Heart Circ Physiol, June 1, 2001; 280(6): H2456 - H2461. [Abstract] [Full Text] [PDF]
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A. Huang, D. Sun, M. A. Carroll, H. Jiang, C. J. Smith, J. A. Connetta, J. R. Falck, E. G. Shesely, A. Koller, and G. Kaley EDHF mediates flow-induced dilation in skeletal muscle arterioles of female eNOS-KO mice Am J Physiol Heart Circ Physiol, June 1, 2001; 280(6): H2462 - H2469. [Abstract] [Full Text] [PDF]
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M. P. Kunert, R. J. Roman, M. Alonso-Galicia, J. R. Falck, and J. H. Lombard Cytochrome P-450 {omega}-hydroxylase: a potential O2 sensor in rat arterioles and skeletal muscle cells Am J Physiol Heart Circ Physiol, April 1, 2001; 280(4): H1840 - H1845. [Abstract] [Full Text] [PDF]
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J. C. Frisbee, R. J. Roman, U. M. Krishna, J. R. Falck, and J. H. Lombard 20-HETE modulates myogenic response of skeletal muscle resistance arteries from hypertensive Dahl-SS rats Am J Physiol Heart Circ Physiol, March 1, 2001; 280(3): H1066 - H1074. [Abstract] [Full Text] [PDF]
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S. I. Pomposiello, M. A. Carroll, J. R. Falck, and J. C. McGiff Epoxyeicosatrienoic Acid-Mediated Renal Vasodilation to Arachidonic Acid Is Enhanced in SHR Hypertension, March 1, 2001; 37(3): 887 - 893. [Abstract] [Full Text] [PDF]
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R. Gu, Y. Wei, H. Jiang, M. Balazy, and W. Wang Role of 20-HETE in mediating the effect of dietary K intake on the apical K channels in the mTAL Am J Physiol Renal Physiol, February 1, 2001; 280(2): F223 - F230. [Abstract] [Full Text] [PDF]
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H. C. Hercule and A. O. Oyekan Role of NO and cytochrome P-450-derived eicosanoids in ET-1-induced changes in intrarenal hemodynamics in rats Am J Physiol Regulatory Integrative Comp Physiol, December 1, 2000; 279(6): R2132 - R2141. [Abstract] [Full Text] [PDF]
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J. D. Imig Eicosanoid regulation of the renal vasculature Am J Physiol Renal Physiol, December 1, 2000; 279(6): F965 - F981. [Abstract] [Full Text] [PDF]
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D. Zhu, E. K. Birks, C. A. Dawson, M. Patel, J. R. Falck, K. Presberg, R. J. Roman, and E. R. Jacobs Hypoxic pulmonary vasoconstriction is modified by P-450 metabolites Am J Physiol Heart Circ Physiol, October 1, 2000; 279(4): H1526 - H1533. [Abstract] [Full Text] [PDF]
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A. Bhardwaj, F. J. Northington, J. R. Carhuapoma, J. R. Falck, D. R. Harder, R. J. Traystman, and R. C. Koehler P-450 epoxygenase and NO synthase inhibitors reduce cerebral blood flow response to N-methyl-D-aspartate Am J Physiol Heart Circ Physiol, October 1, 2000; 279(4): H1616 - H1624. [Abstract] [Full Text] [PDF]
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 M. A Carroll and J. C McGiff A new class of lipid mediators: cytochrome P450 arachidonate metabolites Thorax, October 1, 2000; 55(90002): 13S - 16. [Full Text]
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W. Kozak, M. J. Kluger, A. Kozak, M. Wachulec, and K. Dokladny Role of cytochrome P-450 in endogenous antipyresis Am J Physiol Regulatory Integrative Comp Physiol, August 1, 2000; 279(2): R455 - R460. [Abstract] [Full Text] [PDF]
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D. Gebremedhin, A. R. Lange, T. F. Lowry, M. R. Taheri, E. K. Birks, A. G. Hudetz, J. Narayanan, J. R. Falck, H. Okamoto, R. J. Roman, et al. Production of 20-HETE and Its Role in Autoregulation of Cerebral Blood Flow Circ. Res., July 7, 2000; 87(1): 60 - 65. [Abstract] [Full Text] [PDF]
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J. C. Frisbee, J. R. Falck, and J. H. Lombard Contribution of cytochrome P-450 omega -hydroxylase to altered arteriolar reactivity with high-salt diet and hypertension Am J Physiol Heart Circ Physiol, May 1, 2000; 278(5): H1517 - H1526. [Abstract] [Full Text] [PDF]
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J. M. Lasker, W. B. Chen, I. Wolf, B. P. Bloswick, P. D. Wilson, and P. K. Powell Formation of 20-Hydroxyeicosatetraenoic Acid, a Vasoactive and Natriuretic Eicosanoid, in Human Kidney. ROLE OF CYP4F2 AND CYP4A11 J. Biol. Chem., February 11, 2000; 275(6): 4118 - 4126. [Abstract] [Full Text] [PDF]
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D. Zhu, M. Bousamra II, D. C. Zeldin, J. R. Falck, M. Townsley, D. R. Harder, R. J. Roman, and E. R. Jacobs Epoxyeicosatrienoic acids constrict isolated pressurized rabbit pulmonary arteries Am J Physiol Lung Cell Mol Physiol, February 1, 2000; 278(2): L335 - L343. [Abstract] [Full Text] [PDF]
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J. D. Imig, B. T. Pham, E. A. LeBlanc, K. M. Reddy, J. R. Falck, and E. W. Inscho Cytochrome P450 and Cyclooxygenase Metabolites Contribute to the Endothelin-1 Afferent Arteriolar Vasoconstrictor and Calcium Responses Hypertension, January 1, 2000; 35(1): 307 - 312. [Abstract] [Full Text] [PDF]
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J. C. McGiff and J. Quilley 20-HETE and the kidney: resolution of old problems and new beginnings Am J Physiol Regulatory Integrative Comp Physiol, September 1, 1999; 277(3): R607 - R623. [Abstract] [Full Text] [PDF]
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X. Nguyen, M.-H. Wang, K. M. Reddy, J. R. Falck, and M. L. Schwartzman Kinetic profile of the rat CYP4A isoforms: arachidonic acid metabolism and isoform-specific inhibitors Am J Physiol Regulatory Integrative Comp Physiol, June 1, 1999; 276(6): R1691 - R1700. [Abstract] [Full Text] [PDF]
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A. O. Oyekan, K. McAward, J. Conetta, L. Rosenfeld, and J. C. McGiff Endothelin-1 and CYP450 arachidonate metabolites interact to promote tissue injury in DOCA-salt hypertension Am J Physiol Regulatory Integrative Comp Physiol, March 1, 1999; 276(3): R766 - R775. [Abstract] [Full Text] [PDF]
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B. A. Rzigalinski, K. A. Willoughby, S. W. Hoffman, J. R. Falck, and E. F. Ellis Calcium Influx Factor, Further Evidence It Is 5,6-Epoxyeicosatrienoic Acid J. Biol. Chem., January 1, 1999; 274(1): 175 - 182. [Abstract] [Full Text] [PDF]
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J. D. Imig, E. W. Inscho, P. C. Deichmann, K. M. Reddy, and J. R. Falck Afferent Arteriolar Vasodilation to the Sulfonimide Analog of 11,12-Epoxyeicosatrienoic Acid Involves Protein Kinase A Hypertension, January 1, 1999; 33(1): 408 - 413. [Abstract] [Full Text] [PDF]
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J. T. Weber, B. A. Rzigalinski, and E. F. Ellis Traumatic Injury of Cortical Neurons Causes Changes in Intracellular Calcium Stores and Capacitative Calcium Influx J. Biol. Chem., January 12, 2001; 276(3): 1800 - 1807. [Abstract] [Full Text] [PDF]
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B. A. Escalante, J. C. McGiff, and A. O. Oyekan Role of cytochrome P-450 arachidonate metabolites in endothelin signaling in rat proximal tubule Am J Physiol Renal Physiol, January 1, 2002; 282(1): F144 - F150. [Abstract] [Full Text] [PDF]
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