Co-purification of microsomal epoxide hydrolase with the warfarin-sensitive vitamin K1 oxide reductase of the vitamin K cycle

Biochemical Pharmacology

Volumn 55, Issue 2, 1998, Pages 169-175

  Guenthner, Thomas M ^a   Cai, Danlin ^a   Wallin, Reidar ^b  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^b WAKE FOREST SCHOOL OF MEDICINE   (United States)

Author keywords

Epoxide hydrolase; Microsomes; Vitamin K cycle; Vitamin K1 oxide; Vitamin K1 oxide reductase

Indexed keywords

EPOXIDE HYDROLASE; PHYTOMENADIONE OXIDE;

ANIMAL TISSUE; ANTIBODY BLOOD LEVEL; ARTICLE; CONTROLLED STUDY; ENZYME ACTIVITY; ENZYME PURIFICATION; HYDROLYSIS; LIVER MICROSOME; NONHUMAN; PRIORITY JOURNAL; RAT;

ANIMALS; CHROMATOGRAPHY; CHROMATOGRAPHY, GEL; CROSS REACTIONS; DURAPATITE; ELECTROPHORESIS, POLYACRYLAMIDE GEL; EPOXIDE HYDROLASES; IMMUNE SERA; KINETICS; MICROSOMES, LIVER; MIXED FUNCTION OXYGENASES; MOLECULAR WEIGHT; RATS; WARFARIN;

EID: 0031963266     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-2952(97)00431-0     Document Type: Article

References (35)

1. Beetham J, Grant D, Arand M, Garbarino J, Kiyosue T, Pinot F, Oesch F, Belknap W, Shinozaki K, Hammock B. Gene evolution of epoxide hydrolases and recommended nomenclature. DNA Cell Biol. 14:1995;61-71.
2. Guenthner T. Epoxide hydrolases. Mulder GJ. Conjugation Reactions in Drug Metabolism An Integrated Approach . 1990;365-404 Taylor & Francis, New York.
3. El-Tantawy M, Hammock B. The effect of hepatic microsomal and cytosolic subcellular fractions on the mutagenic activity of epoxide-containing compounds in the salmonella assay. Mutat Res. 79:1980;59-71.
4. Oesch F. Mammalian epoxide hydrolases Inducible enzymes catalyzing the inactivation of carcinogenic and cytotoxic metabolites derived from aromatic and olefinic compounds . Xenobiotica. 3:1973;305-340.
5. Luo G, Qato M, Guenthner T. Hydrolysis of the 2′,3′-allylic epoxides of allylbenzene, estragole, eugenol, and safrole by both microsomal and cytosolic epoxide hydrolases. Drug Metab Dispos. 20:1992;440-445.
6. Bindel U, Sparrow A, Schmassmann H, Golan M, Bentley P, Oesch F. Endogenous role of epoxide-hydratase. Development of a steroid epoxide-hydratase assay and properties of the enzyme. Eur J Biochem. 97:1979;275-281.
7. (+)-dependent bile acid transport by hepatocytes is mediated by a protein similar to microsomal epoxide hydrolase. Am J Physiol. 264:1993;G528-G534.
8. Honscha W, Platte H, Oesch F, Friedberg T. Relationship between the microsomal epoxide hydrolase and the hepatocellular transport of bile acids and xenobiotics. Biochem J. 311:1995;975-979.
9. von Dippe P, Amoui M, Stellwagen RH, Levy D. The functional expression of sodium-dependent bile acid transport in Madin-Darby canine kidney cells transfected with the cDNA for microsomal epoxide hydrolase. J Biol Chem. 271:1996;18176-18180.
10. Proctor K, Falck J, Capdevila J. Intestinal vasodilation by epoxyeicosatrienoic acids Arachidonic acid metabolites produced by a cytochrome P450 monooxygenase . Circ Res. 60:1987;50-59.
11. Cashman J, Hanks D, Weiner R. Epoxy derivatives of arachidonic acid are potent stimulators of prolactin secretion. Neuroendocrinology. 46:1987;246-251.
12. Chacos N, Capdevila J, Falck J, Manna S, Martin-Wixtrom C, Gill S, Hammock B. The reaction of arachidonic acid epoxides (epoxyeicosatrienoic acids) with a cytosolic epoxide hydrolase. Arch Biochem Biophys. 223:1983;639-648.
13. Haeggström J, Meijer J, Rådmark O. Leukotriene A4. Enzymatic conversion into 5,6-dihydroxy-7,9,11,14-eicosatetraenoic acid by mouse liver cytosolic epoxide hydrolase. J Biol Chem. 261:1986;6332-6337.
14. Levin W, Michaud DP, Thomas PE, Jerina DM. Distinct rat hepatic microsomal epoxide hydrolases catalyze the hydration of cholesterol 5,6α-oxide and certain xenobiotic alkene and arene oxides. Arch Biochem Biophys. 220:1983;485-494.
15. Watabe T, Osawa N, Ishii H, Chiba K, Hiratsuka A. Hepatic microsomal cholesterol epoxide hydrolase selective inhibition by detergents and separation from xenobiotic epoxide hydrolase . Biochem Biophys Res Commun. 140:1986;632-637.
16. Suttie J. Recent advances in hepatic vitamin K metabolism and function. Hepatology. 7:1987;367-376.
17. Furie B, Furie BC. The molecular basis of blood coagulation. Cell. 53:1988;505-518.
18. Wallin R, Martin L. Early processing of prothrombin and factor X by the vitamin K-dependent carboxylase. J Biol Chem. 263:1988;9994-10001.
19. 3H cleavage. J Biol Chem. 263:1988;3234-3239.
20. Wallin R, Martin F. Vitamin K-dependent carboxylation and vitamin K metabolism in liver Effects of warfarin . J Clin Invest. 76:1985;1879-1884.
21. Silverman R, Nandi D. Reduced thioredoxin A possible physiological cofactor for vitamin K epoxide reductase. Further support for an active site disulfide . Biochem Biophys Res Commun. 155:1988;1248-1254.
22. Hirsh J. Oral anticoagulant drugs. New Engl J Med. 324:1991;1865-1875.
23. Fasco M, Principe L. R- and S-Warfarin inhibition of vitamin K and vitamin K, 2,3-epoxide reductase activities in the rat. J Biol Chem. 257:1982;4894-4901.
24. Liptay-Reuter I, Dose K, Guenthner T, Wörner W, Oesch F. Vitamin K epoxide reductase activity in the metabolism of epoxides. Biochem Pharmacol. 34:1985;2617-2620.
25. Guenthner T, Hammock B, Vogel U, Oesch F. Cytosolic and microsomal epoxide hydrolases are immunologically distinguishable from each other in the rat and mouse. J Biol Chem. 256:1981;3163-3166.
26. 1 and related compounds. J Am Chem Soc. 62:1940;2866-2871.
27. Tallarida R and Murray R, Manual of Pharmacologic Calculations with Computer Programs. Springer, New York, 1981.
28. Lu A, Ryan D, Jerina D, Daly J, Levin W. Liver microsomal epoxide hydrase Solubilization, purification, and characterization . J Biol Chem. 250:1975;8283-8288.
29. Bell P, Kasper C. Expression of rat microsomal epoxide hydrolase in Escherichia coli. Identification of a histidyl residue essential for catalysis. J Biol Chem. 268:1993;14011-14017.
30. Levin W, Thomas P, Korzeniowski D, Seifried H, Jerina D, Lu A. Liver microsomal epoxide hydrolase Activation, inhibition, and immunological properties of the purified enzyme . Mol Pharmacol. 14:1978;1107-1120.
31. Wolf C, Oesch F, Timms C, Guenthner T, Hartmann R, Maruhn M, Burger R. Use of monoclonal and polyclonal antibodies as structural and topographical probes for hepatic epoxide hydrolase. FEBS Lett. 157:1983;271-276.
32. Falany C, McQuiddy P, Kasper C. Structure and organization of the microsomal xenobiotic epoxide hydrolase gene. J Biol Chem. 262:1987;5924-5930.
33. Skoda R, Demierre A, McBride O, Gonzalez F, Meyer U. 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.
34. Bulleid N, Graham A, Craft J. Microsomal epoxide hydrolase of rat liver. Purification and characterization of enzyme fractions with different chromatographic characteristics. Biochem J. 233:1986;607-611.
35. Honscha W, Oesch F, Friedberg T. Tissue-specific expression and differential inducibility of several microsomal epoxide hydrolase mRNAs which are formed by alternative splicing. Arch Biochem Biophys. 287:1991;380-385.