Impact of genetic polymorphisms in CYP2C8 and rosiglitazone intake on the urinary excretion of dihydroxyeicosatrienoic acids

Pharmacogenomics

Volumn 9, Issue 3, 2008, Pages 277-288

  Kirchheiner, Julia ^a   Meineke, Ingolf ^b   Fuhr, Uwe ^c   Rodriguez Antona, Cristina ^d   Lebedeva, Elena ^a   Brockmöller, Jürgen ^b  

^a UNIVERSITY OF ULM   (Germany)

^b UNIVERSITY OF GÖTTINGEN   (Germany)

^c UNIVERSITY OF COLOGNE   (Germany)

^d Centro Nacional de Investigaciones Oncológicas   (Spain)

Author keywords

CYP2C8; Cytochrome P450; Eicosanoids; Epoxyeicosatetraenoic acid

Indexed keywords

14,15 EPOXY 5,8,11 ICOSATRIENOIC ACID; ADENINE; CARNOSIC ACID; CYTOCHROME P450 2C8; CYTOCHROME P450 2C9; CYTOCHROME P450 2J2; CYTOSINE; DIHYDROXYICOSATETRAENOIC ACID; DRUG METABOLIZING ENZYME; GUANINE; HEPOXILIN A; HYDROXYICOSATETRAENOIC ACID; ROSIGLITAZONE; 2,4 THIAZOLIDINEDIONE DERIVATIVE; ANTIDIABETIC AGENT; CYP2C8 PROTEIN, HUMAN; UNCLASSIFIED DRUG; UNSPECIFIC MONOOXYGENASE;

ALLELE; ARTICLE; CONTROLLED STUDY; DRUG CLEARANCE; DRUG EXCRETION; DRUG METABOLISM; ENZYME SUBSTRATE; FEMALE; GENETIC POLYMORPHISM; GENETIC VARIABILITY; GENOTYPE; HAPLOTYPE; HETEROZYGOSITY; HUMAN; HUMAN EXPERIMENT; MALE; MORNING DOSAGE; PHARMACOGENOMICS; TANDEM MASS SPECTROMETRY; URINALYSIS; GENETICS; HETEROZYGOTE DETECTION; POLYMERASE CHAIN REACTION; URINE;

ARYL HYDROCARBON HYDROXYLASES; FEMALE; GENOTYPE; HETEROZYGOTE DETECTION; HUMANS; HYDROXYEICOSATETRAENOIC ACIDS; HYPOGLYCEMIC AGENTS; MALE; POLYMERASE CHAIN REACTION; POLYMORPHISM, GENETIC; THIAZOLIDINEDIONES;

EID: 42449141140     PISSN: 14622416     EISSN: 17448042     Source Type: Journal    
DOI: 10.2217/14622416.9.3.277     Document Type: Article

References (44)

1. Spiecker M, Darius H, Hankeln T et al.: Risk of coronary artery disease associated with polymorphism of the cytochrome P450 epoxygenase CYP2J2.Circulation 110, 2132-2136 (2004).
2. Spiecker M, Liao J: Cytochrome P450 epoxygenase CYP2J2 and the risk of coronary artery disease. Trends Cardiovasc. Med. 16, 204-208 (2006).
3. Visser LE, van Schaik RH, Jan Danser AH et al.: The risk of myocardial infarction in patients with reduced activity of cytochrome P450 2C9. Pharmacogenet. Genomics 17, 473-479 (2007).
4. Yasar U, Bennet AM, Eliasson E et al.: Allellic variants of cytochromes P450 2C modify the risk for acute myocardial infarction. Pharmacogenetics 13, 715-720 (2003).
5. Liu PY, Li YH, Chao TH et al.: Synergistic effect of cytochrome P450 epoxygenase CYP2J2*7 polymorphism with smoking on the onset of premature myocardial infarction. Atherosclerosis 199-206 (2006).
6. Lee CR, North KE, Bray MS, Couper DJ, Heiss G, Zeldin DC: CYP2J2 and CYP2C8 polymorphisms and coronary heart disease risk: the Atherosclerosis Risk in Communities (ARIC) study. Pharmacogenet. Genomics 17, 349-358 (2007).
7. Fleming I, Busse R: Endothelium-derived epoxyeicosatrienoic acids and vascular function. Hypertension 47, 629-633 (2006).
8. Fissfthaler B, Popp R, Kiss L et al.: Cytochrome P450 2C is an EDHF synthase in coronary arteries. Nature 401, 493-497 (1999).
9. Fang X, Hu S, Xu B et al.: 14, 1 5-Dihydroxyeicosatrienoic acid activates peroxisome proliferator-activated receptor-α. Am. J. Physiol. Heart Circ. Physiol. 290, H55-H63 (2006).
10. Node K, Huo Y, Ruan X et al.: Anti-inflammatory properties of cytochrome P450 epoxygenase-derived eicosanoids. Science 285, 1276-1279 (1999).
11. Spiecker M, Liao JK: Vascular protective effects of cytochrome p450 epoxygenase-derived eicosanoicis. Arch Biochem. Biophys. 433, 413-420 (2005).
12. Yu Z, Huse LM, Adler P et al.: Increased CYP2J expression and epoxyeicosatrienoic acid formation in spontaneously hypertensive rat kidney. Mol. Pharmacol. 57, 1011-1020 (2000).
13. + currents in transgenic mice with cardiac-specific overexpression of CYP2J2. Mol. Pharmacol. 66, 1607-1616 (2004).
14. Dal D, Zeldin DC, Blaisdell, JA et al.: Polymorphisms in human CYT2C8 decrease metabolism of the anticancer drug paclitaxel and arachidonic acid. Pharmacogenetics 11, 597-607 (2001).
15. Barbosa-Sicard E, Markovic, M, Honeck H, Christ B, Muller DN, Schunck WH: Eicosapentaenoic acid metabolism by cytochrome P450 enzymes of the CYP2C subfamily. Biochem. Biophys. Res. Commun. 329, 1275-1281 (2005).
16. Lundblad MS, Stark K, Eliasson E, Olivv E, Rane A: Biosynthesis of epoxyeicosatrienoic acids varies between polymorphic CYP2C enzymes. Biochem. Biophys Res. Commun. 327, 1052-1057 (2005).
17. 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. Rev. 31, 205-234 (1999).
18. Zeldin DC: Epoxygenase pathways of arachidonic acid metabolism. J. Biol. Chem. 276, 36059-36062 (2001).
19. Kirchheiner J, Thomas S, Bauer S et al.: Pharmacokinetics and pharmacodynamics of rosiglitazone in relation to CYP2C8 genotype. Clin. Pharmacol. Ther. 80, 657-667 (2006).
20. Yamazaki H, Suzuki M, Tane K, Shimada N, Nakajima M, Yokoi T: In vitro inhibitory effects of troglitazone and its metabolites on drug oxidation activities of human cytochrome P450 enzymes: comparison with pioglitazone and rosiglitazone. Xenobiotica 30, 61-70 (2000).
21. Walsky RL, Gaman EA, Obach RS: Examination of 209 drugs for inhibition of cytochrome P450 2C8. J. Clin. Pharmacol. 45, 68-78 (2005).
22. Sahi J, Black CB, Hamilton GA et al.: Comparative effects of thiazolidinediones on in vitro P450 enzyme induction and inhibition. Drug Metab. Dispos. 31, 439-446 (2003).
23. Rodriguez-Antona C. Niemi M, Backman JT et al.: Characterization of novel CYP2C8 haplotypes and their contribution to paclitaxel and repaglinide metabolism. Pharmacogenomics J. (2007) (Epub ahead of print).
24. King LM, Ma J, Srettabunjong S et al.: Cloning of CYP2J2 gene and identification of functional polymorphisms. Mol. Pharmacol. 61, 840-852 (2002).
25. Kirchheiner J, Ufer M, Walter EC et al.: Effects of CYP2C9 polymorphisms on the pharmacokinetics of R- and S-phenprocoumon in healthy volunteers. Pharmacogeneties 14, 19-26 (2004).
26. Zelinski V, Borlak J: Identification and quantification of metabolites of arachidonic acid from cultures of endothelial cells by HPLC-MS2. Xenobiotica 35, 811-823 (2005).
27. Yu Z, Xu F, Huse LM et al.: Soluble epoxide hydrolase regulates hydrolysis of vasoactive epoxyeicosatrienoic acids. Circ. Res. 87, 992-998 (2000).
28. 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 Res. 43, 1563-1578 (2002).
29. Rifkind AB, Lee C, Chang TK, Waxman DJ: 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).
30. Niemi M, Backman JT, Kajosaari LI et al.: Polymorphic organic anion transporting polypeptide 1B1 is a major determinant of repaglinide pharmacokinetics. Clin. Pharmacol. Ther. 77, 468-478 (2005).
31. Niemi M, Leathart JB, Neuvonen M, Backman JT, Daly AK, Neuvonen PJ: Polymorphism in CYP2C8 is associated with reduced plasma concentrations of repaglinide. Clin. Pharmacol. Ther. 74, 380-387 (2003).
32. Hruska, MW, Cheong JA, Amico MD, Langgae TY, Frye RF: Effect of CYP2C8 genotype on rosiglitazone pharmacokinetics. Clin. Pharmacol. Ther. 77, P36 (2005).
33. Kirchheiner, J, Thomas S, Bauer S et al.: Pharmacokinetics and pharmacodynamics of rosiglitazone in relation to CYP2C8 genotype. Clin. Pharmacol. Ther. 80, 657-667 (2006).
34. Dai D, Zeldin DC, Blaisdell JA et al.: Polymorphisms in human CYP2C8 decrease metabolism of the anticancer drug paclitaxel and arachidonic acid. Pharmacogenetics 11, 597-607 (2001).
35. Lundblad MS, Stark K, Eliasson E, Oliw E, Rane A: Biosynthesis of epoxyeicosatrienoic acids varies between polymorphic CYP2C enzymes. Biochem. Biophys Res. Commun. 327, 1052-1057 (2005).
36. Saito Y, Katori N, Soyama A et al.: CYP2C8 haplotype structures and their influence on pharmacokinetics of paclitaxel in a Japanese population. Pharmacogenet. Genomics 17, 461-471 (2007).
37. Fleming I: DiscrEET regulators of homeostasis: epoxyeicosatrienoic acids, cytochrome P450 epoxygenases and vascular inflammation. Trends Pharmacol. Sci. 28, 448-452 (2007).
38. Przybyla-Zawislak BD, Srivastava PK, Vazquez-Matias J et al.: Polymorphisms in human soluble epoxide hydrolase. Mol. Pharmacol. 64, 482-490 (2003).
39. Lee CR, North KE, Bray MS et al.: Genetic variation in soluble epoxide hydrolase (EPHX2) and risk of coronary heart disease: The Atherosclerosis Risk in Communities (ARIC) study. Hum. Mol. Genet. 15, 1640-1649 (2006).
40. Fang X, Weintraub NL, McCaw RB et al.: Effect of soluble epoxide hydrolase inhibition on epoxyeicosatrienoic acid metabolism in human blood vessels. Am. J. Physiol. Heart Circ. Physiol. 287, H2412-H2420 (2004).
41. Widstrom RL, Norris AW, van der Veer J, Spector AA: Fatty acid-binding proteins inhibit hydration of epoxyeicosatrienoic acids by soluble epoxide hydrolase. Biochemistry 42, 11762-11767 (2003).
42. Catella F, Lawson JA, Fitzgerald DJ, FitzGerald GA: Endogenous biosynthesis of arachidonic acid epoxides in humans: increased formation in pregnancy-induced hypertension. Proc. Natl Acad. Sci. USA 87, 5893-5897 (1990).
43. Imig JD, Zhao X, Falck JR, Wei S, Capdevila JH: Enhanced renal microvascular reactivity to angiotensin II in hypertension is ameliorated by the sulfonimide analog of 11, 12-epoxyeicosatrienoic acid. J Hypertens. 19, 983-992 (2001).
44. Zhao X, Yamamoto T, Newman JW et al.: Soluble epoxide hydrolase inhibition protects the kidney from hypertension-induced damage. J. Am. Soc. Nephrol. 15, 1244-1253 (2004).