Epoxide hydrolase - Polymorphism and role in toxicology

Toxicology Letters

Volumn 112-113, Issue , 2000, Pages 365-370

  Omiecinski, Curtis J ^a   Hassett, Christopher ^a   Hosagrahara, Vinayak ^a  

^a UNIVERSITY OF WASHINGTON   (United States)

Author keywords

Benzo(a) pyrene 4,5 oxide; Cis stilbene oxide; Epoxide hydrolase; Polymorphism baculovirus expression

Indexed keywords

EPOXIDE HYDROLASE; RECOMBINANT ENZYME; XENOBIOTIC AGENT;

AMINO ACID COMPOSITION; BACULOVIRUS; CONFERENCE PAPER; CONTROLLED STUDY; DRUG TRANSFORMATION; ENZYME ACTIVITY; ENZYME ANALYSIS; ENZYME KINETICS; ENZYME PURIFICATION; GENE EXPRESSION; GENETIC POLYMORPHISM; GENETIC VARIABILITY; GENOTYPE; HUMAN; HUMAN TISSUE; IN VITRO STUDY; LIVER METABOLISM; PHENOTYPE; PRIORITY JOURNAL;

CELLS, CULTURED; EPOXIDE HYDROLASES; HUMANS; MICROSOMES, LIVER; PHENOTYPE; POLYMORPHISM, GENETIC; SUBSTRATE SPECIFICITY; TOXICOLOGY; VARIATION (GENETICS);

UNIDENTIFIED BACULOVIRUS;

EID: 0034653356     PISSN: 03784274     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0378-4274(99)00235-0     Document Type: Conference Paper

References (35)

1. Adams J.D. Jr, Yagi H., Levin W., Jerina D.M. Stereo-selectivity and regio-selectivity in the metabolism of 7, 8-dihydrobenzo[a]pyrene by cytochrome P450, epoxide hydrolase and hepatic microsomes from 3-methylcholanthrene-treated rats. Chem. Biol. Interact. 95:1995;57-77.
2. Bauer E., Guo Z., Ueng Y.F., Bell L.C., Zeldin D., Guengerich F.P. Oxidation of benzo[a]pyrene by recombinant human cytochrome P450 enzymes. Chem. Res. Toxicol. 8:1995;136-142.
3. Beetham J.K., Tian T., Hammock B.D. cDNA cloning and expression of a soluble epoxide hydrolase from human liver. Arch. Biochem. Biophys. 305:1993;197-201.
4. Beetham J.K., Grant D., Arand M., Garbarino J., Kiyosue T., Pinot F., Oesch F., Belknap W.R., Shinozaki K., Hammock B.D. Gene evolution of epoxide hydrolases and recommended nomenclature. DNA Cell Biol. 14:1995;61-71.
5. Bjelogrlic N.M., Makinen M., Stenback F., Vahakangas K. Benzo[a]pyrene-7,8-diol-9,10-epoxide-DNA adducts and increased p53 protein in mouse skin. Carcinogenesis. 15:1994;771-774.
6. Fandrich F., Degiuli B., Vogel Bindel U., Arand M., Oesch F. Induction of rat liver microsomal epoxide hydrolase by its endogenous substrate 16α, 17α-epoxyestra-1,3,5-trien-3-ol. Xenobiotica. 25:1995;239-244.
7. Fu J.Y., Haeggstrom J., Collins P., Meijer J., Radmark O. Leukotriene A4 hydrolase: analysis of some human tissues by radioimmunoassay. Biochim. Biophys. Acta. 1006:1989;121-126.
8. Gaedigk A., Spielberg S.P., Grant D.M. Characterization of the microsomal epoxide hydrolase gene in patients with anticonvulsant adverse drug reactions. Pharmacogenetics. 4:1994;142-153.
9. Gasser R. The flavin-containing monooxygenase system. Exp. Toxicol. Pathol. 48:1996;467-470.
10. Guengerich F.P. Epoxide hydrolase: properties and metabolic roles. Rev. Biochem. Toxicol. 4:1982;5-30.
11. Haeggstrom J.Z., Wetterholm A., Medina J.F., Samuelsson B. Novel structural and functional properties of leukotriene A4 hydrolase. Implications for the development of enzyme inhibitors. Adv. Prostaglandin Thromboxane Leukot. Res. 22P3-12:1994;3-12.
12. Hassett C., Aicher L., Sidhu J.S., Omiecinski C.J. Human microsomal epoxide hydrolase: genetic polymorphism and functional expression in vitro of amino acid variants. Hum. Mol. Genet. 3:1994;421-428.
13. Hassett C., Robinson K.B., Beck N.B., Omiecinski C.J. The human microsomal epoxide hydrolase gene (EPHX1): complete nucleotide sequence and structural characterization. Genomics. 23:1994;433-442.
14. Hassett C., Lin J., Carty C.L., Laurenzana E.M., Omiecinski C.J. Human hepatic microsomal epoxide hydrolase: comparative analysis of polymorphic expression. Arch. Biochem. Biophys. 337:1997;275-283.
15. Hassett C., Laurenzana E.M., Sidhu J.S., Omiecinski C.J. Effects of chemical inducers on human microsomal epoxide hydrolase in primary hepatocyte cultures. Biochem. Pharmacol. 55:1998;1059-1069.
16. Lancaster J.M., Brownlee H.A., Bell D.A., Futreal P.A., Marks J.R., Berchuck A., Wiseman R.W., Taylor J.A. Microsomal epoxide hydrolase polymorphism as a risk factor for ovarian cancer. Mol. Carcinog. 17:1996;160-162.
17. Laurenzana E.M., Hassett C., Omiecinski C.J. Post-transcriptional regulation of human microsomal epoxide hydrolase. Pharmacogenetics. 8:1998;157-167.
18. McGlynn K.A., Rosvold E.A., Lustbader E.D., Hu Y., Clapper M.L., Zhou T., Wild C.P., Xia X.L., Baffoe Bonnie A., Ofori Adjei D. et al. Susceptibility to hepatocellular carcinoma is associated with genetic variation in the enzymatic detoxification of aflatoxin B1. Proc. Natl. Acad. Sci. USA. 92:1995;2384-2387.
19. Moody D.E., Hammock B.D. Purification of microsomal epoxide hydrolase from liver of rhesus monkey: partial separation of cis- and trans-stilbene oxide hydrolase. Arch. Biochem. Biophys. 258:1987;156-166.
20. Omiecinski C.J., Aicher L., Holubkov R., Checkoway H. Human peripheral lymphocytes as indicators of microsomal epoxide hydrolase activity in liver and lung. Pharmacogenetics. 3:1993;150-158.
21. Omiecinski C.J., Aicher L., Swenson L. Developmental expression of human microsomal epoxide hydrolase. J. Pharmacol. Exp. Ther. 269:1994;417-423.
22. Pace Asciak C.R., Lee W.S. Purification of hepoxilin epoxide hydrolase from rat liver. J. Biol. Chem. 264:1989;9310-9313.
23. Papadopoulos D., Seidegard J., Georgellis A., Rydstrom J. Subcellular distribution, catalytic properties and partial purification of epoxide hydrolase in the human adrenal gland. Chem. Biol. Interact. 55:1985;249-260.
24. Raaka S., Hassett C., Omiencinski C.J. Human microsomal epoxide hydrolase: 5′-flanking region genetic polymorphisms. Carcinogenesis. 19:1998;387-393.
25. Rappaport S.M., Yeowell-O'Connell K., Bodell W., Yager J.W., Symanski E. An investigation of multiple biomarkers among workers exposed to styrene and styrene-7,8-oxide. Cancer Res. 56:1996;5410-5416.
26. Sayer J.M., Yagi H., van Bladeren P.J., Levin W., Jerina D.M. Stereoselectivity of microsomal epoxide hydrolase toward diol epoxides and tetrahydroepoxides derived from benz[a]anthracene. J. Biol. Chem. 260:1985;1630-1640.
27. Seidegard J., DePierre J.W., Guenthner T.M., Oesch F. The effects of metyrapone, chalcone epoxide, benzil, clotrimazole and related compounds on the activity of microsomal epoxide hydrolase in situ, in purified form and in reconstituted systems towards different substrates. Eur. J. Biochem. 159:1986;415-423.
28. Sevanian A., McLeod L.L. Catalytic properties and inhibition of hepatic cholesterol-epoxide hydrolase. J. Biol. Chem. 261:1986;54-59.
29. Shou M., Gonzalez F.J., Gelboin H.V. Stereoselective epoxidation and hydration at the K-region of polycyclic aromatic hydrocarbons by cDNA-expressed cytochromes P450 1A1, 1A2, and epoxide hydrolase. Biochemistry. 35:1996;15807-15813.
30. Skoda R.C., Demierre A., McBride O.W., Gonzalez F.J., Meyer U.A. Human microsomal xenobiotic epoxide hydrolase. Complementary DNA sequence, complementary DNA-directed expression in COS-1 cells, and chromosomal localization. J. Biol. Chem. 263:1988;1549-1554.
31. Smith C.A., Harrison D.J. Association between polymorphism in gene for microsomal epoxide hydrolase and susceptibility to emphysema. Lancet. 350:1997;630-633.
32. Thakker D.R., Levin W., Yagi H., Yeh H.J., Ryan D.E., Thomas P.E., Conney A.H., Jerina D.M. Stereoselective metabolism of the (+)-(S,S)- and (-)-(R,R)- enantiomers of trans-3,4-dihydroxy-3,4-dihydrobenzo[c]-phenanthrene by rat and mouse liver microsomes and by a purified and reconstituted cytochrome P-450 system. J. Biol. Chem. 261:1986;5404-5413.
33. Wood A.W., Chang R.L., Levin W., Kumar S., Shirai N., Jerina D.M., Lehr R.E., Conney A.H. Bacterial and mammalian cell mutagenicity of four optically active bay-region 3,4-diol-1,2-epoxides and other derivatives of the nitrogen heterocycle dibenz[c,h]acridine. Cancer Res. 46:1986;2760-2766.
34. Zeldin D.C., Kobayashi J., Falck J.R., Winder B.S., Hammock B.D., Snapper J.R., Capdevila J.H. Regio- and enantiofacial selectivity of epoxyeicosatrienoic acid hydration by cytosolic epoxide hydrolase. J. Biol. Chem. 268:1993;6402-6407.
35. Zeldin D.C., Wei S., Falck J.R., Hammock B.D., Snapper J.R., Capdevila J.H. Metabolism of epoxyeicosatrienoic acids by cytosolic epoxide hydrolase: substrate structural determinants of asymmetric catalysis. Arch. Biochem. Biophys. 316:1995;443-451.