Characterization and cDNa cloning of a clofibrate-inducible microsomal epoxide hydrolase in Drosophila melanogaster

European Journal of Biochemistry

Volumn 270, Issue 23, 2003, Pages 4696-4705

  Taniai, Kiyoko ^a   Inceoglu, Ahmet B ^b   Yukuhiro, Kenji ^a   Hammock, Bruce D ^b  

^a NATIONAL INSTITUTE OF AGROBIOLOGICAL SCIENCES   (Japan)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Detoxification; Drosophila melanogaster; Epoxide hydrolase; Induction; Insect

Indexed keywords

AMINO ACID; CLOFIBRATE; COMPLEMENTARY DNA; EPOXIDE HYDROLASE; GLUTATHIONE TRANSFERASE; JUVENILE HORMONE; MICROSOME ENZYME; PHENOXYACETIC ACID DERIVATIVE; PROPYLENE OXIDE; STILBENE OXIDE;

ARTICLE; ASSAY; BACULOVIRUS; BIOTRANSFORMATION; CONTROLLED STUDY; DNA LIBRARY; DOSE RESPONSE; DROSOPHILA MELANOGASTER; GENE EXPRESSION; GENE ISOLATION; GENETIC TRANSCRIPTION; HOMOGENATE; HYDROLYSIS; INSECT CELL; LARVA; MAMMAL; MICROSOME; MOLECULAR CLONING; NONHUMAN; NORTHERN BLOTTING; NUCLEOTIDE SEQUENCE; OPEN READING FRAME; PRIORITY JOURNAL; VIRUS INFECTION; XENOBIOTIC METABOLISM;

AMINO ACID SEQUENCE; ANIMALS; BACULOVIRIDAE; BASE SEQUENCE; CHROMOSOME MAPPING; CLOFIBRATE; CLONING, MOLECULAR; DNA, COMPLEMENTARY; DROSOPHILA MELANOGASTER; ENZYME INDUCTION; EPOXIDE HYDROLASES; EVOLUTION, MOLECULAR; LARVA; MOLECULAR SEQUENCE DATA; RNA, MESSENGER; SEQUENCE ALIGNMENT; SEQUENCE HOMOLOGY, AMINO ACID; SUBSTRATE SPECIFICITY;

ARACHNIDA; DROSOPHILA MELANOGASTER; HEXAPODA; INSECTA; MAMMALIA; MELANOGASTER; UNIDENTIFIED BACULOVIRUS;

EID: 0345688025     PISSN: 00142956     EISSN: None     Source Type: Journal    
DOI: 10.1046/j.1432-1033.2003.03868.x     Document Type: Article

References (40)

1. Oesch, F. (1973) Mammalian epoxide hydrases: inducible enzymes catalysing the inactivation of carcinogenic and cytotoxic metabolites derived from aromatic and olefinic compounds. Xenobiotica 3, 305-340.
2. Oesch, F., Herrero, M.E., Hengstler, J.G., Lohmann, M. & Arand, M. (2000) Metabolic detoxification: implications for thresholds. Toxicol. Pathol. 28, 382-387.
3. Fretland, A.J. & Omiecinski, C.J. (2000) Epoxide hydrolases: biochemistry and molecular biology. Chemico-Biol. Interac. 129, 41-59.
4. Thabrew, M.I. & Emerole, G.O. (1983) Variations in induction of drug-metabolizing enzymes by trans-stilbene oxide in rodent species. Biochim. Biophys. Acta 756, 242-246.
5. Cha, Y.N., Heine, H.S. & Ansher, S. (1983) Compara live effects of dietary administration of antioxidants and inducers on the activities of several hepatic enzymes in mice. Drug Nutr. Interact. 2, 35-45.
6. Kawabata, T.T., Guengerich, F.P. & Baron, J. (1983) Effects of phenobarbital, trans-stilbene oxide, and 3-methylcholanthrene on epoxide hydrolase within centrilobular, midzonal, and periportal regions of rat liver. J. Biol. Chem. 258, 7767-7773.
7. Finley, B.L. & Hammock, B.D. (1988) Increased cholesterol epoxide hydrolase activity in clofibrate-fed animals. Biochem. Pharmacol. 37, 3169-3175.
8. Meijer, J. & DePierre, J.W. (1987) Hepatic levels of cytosolic, microsomal and mitochondrial epoxide hydrolases and other drug-metabolizing enzymes after treatment of mice with various xenobiotics and endogenous compounds. Chem. Biol. Interact. 62, 249-269.
9. Lundgren, B. & DePierre, J.W. (1989) Proliferation of peroxisomes and induction of cytosolic and microsomal epoxide hydrolases in different strains of mice and rats after dietary treatment with clofibrate. Xenobiotica 19, 867-881.
10. Slawson, M.H., Franklin, M.R. & Moody, D.E. (1996) Correlations of the induction of microsomal epoxide hydrolase activity with phase II drug conjugating enzyme activities in rat liver. Toxicol. Lett. 85, 29-34.
11. Nuwaysir, E.F., Dragan, Y.P., Jefcoate, C.R., Jordan, V.C. & Pitot, H.C. (1995) Effects of tamoxifen administration on the expression of xenobiotic metabolizing enzymes in rat liver. Cancer Res. 55, 1780-1786.
12. Craft, J.A., Bulleid, N.J., Jackson, M.R. & Burchell, B. (1988) Induction of microsomal epoxide hydrolase by nitrosamines in rat liver. Effect on messenger ribonucleic acids. Biochem. Pharmacol. 37, 297-302.
13. Seidegard, J. & DePierre, J.W. (1980) Benzil, a potent activator of microsomal epoxide hydrolase in vitro. Eur. J. Biochem. 112, 643-648.
14. Hammock, B.D. & Ota, K. (1983) Differential induction of cytosolic epoxide hydrolase, microsomal epoxide hydrolase, and glutathione S-transferase activities. Toxicol. Appl. Pharmacol. 71, 254-265.
15. Lundgren, B., Meijer, J. & Depierre, J.W. (1987) Induction of cytosolic and microsomal epoxide hydrolases and mitochondria in mouse liver after dietary exposure to p-chlorophenoxyacetic acid, 2,4-dichlorophenoxyacetic acid and 2,4,5-trichlorophenoxyacetic acid. Biochem. Pharmacol. 36, 815-821.
16. Jansen, M., Baars, A.J. & Breimer, D.D. (1986) Microsomal and cytosolic epoxide hydrolase in Drosophila melanogaster. Biochem. Pharmacol. 35, 2229-2232.
17. Ottea, J.A., Harshman, L.O. & Hammock, B. (1987) Pattern of epoxide metabolism by epoxide hydrolase and glutathione S-transeferase associated with age and genotype in Drosophila melanogaster. Mutat. Res. 177, 247-254.
18. Brooks, G.T., Harrison, A. & Lewis, S.E. (1970) Cyclodiene epoxide ring hydration by microsomes from mammalian liver and houseflies. Biochem. Pharmacol. 19, 255-273.
19. Dauterman, W.C. (1982) The role of hydrolases in insecticide metabolism and the toxicological significance of the metabolites. J. Toxicol. Clin. Toxicol. 19, 623-635.
20. Baars, A.J., Jansen, M. & Breimer, D.D. (1979) Xenobiotica- metabolizing enzymes in Drosophila melanogaster: activities of epoxide hydratase and glutathione S-transferase compared with similar activities in rat liver. Mutat. Res. 62, 279-291.
21. Ottea, J.A., Plapp, F.W. Jr & Hammock, B.D. (1987) Biochemical and genetic analysis of epoxide-metabolizing enzymes in susceptible and resistant house flies, Musca domestica L. Pesticide Biochem. Physiol. 29, 138-145.
22. Altaratz, M., Applebaum, S.W., Richard, D.S., Gilbert, L.J. & Segal, D. (1991) Regulation of juvenile hormone synthesis in wild-type and apterous mutant Drosophila. Mol. Cell. Endocrinol. 81, 205-216.
23. Gilbert, L.J., Rybczynski, R. & Tobe, S.S. (1996) Endcrine cascade in insect metamorphosis. In Metamorphosis (Girbert, L.I., Tata, J.R. & Atkinson, B.G., eds). Academic Press. Inc., San Diego.
24. Tohara, K. & Prestwich, G.D. (1993) Juvenile hormone epoxide hydrolase. J. Biol. Chem. 268, 19604-19609.
25. Wojtasek, H. & Prestwich, G.D. (1996) An insect juvenile hormone-specific epoxide hydroase is related to vertebrate microsomal epoxide hydrolases. Biochem. Biophys. Res. Commun. 220, 323-329.
26. Harris, S.V., Thompson, D.M., Linderman, R.J., Tomalski, M.D. & Roe, R.M. (1999) Cloning and expression of a novel juvenile hormone-metabolizing epoxide hydrolase during larval-pupal metamorphosis of the cabbage looper, Tricoplusia ni. Insect Mol. Biol. 8, 85-96.
27. Keiser, K.C., Brandt, K.S., Silver, G.M. & Wisnewski, N. (2002) Cloning, partial purification and in vivo developmental profile of expression of the juvenile hormone epoxide hydrolase of Ctenocephalides felis. Arch. Insect Biochem. Physiol. 50, 191-206.
28. Gill, S.S., Ota, K. & Hammock, B.D. (1983) Radiometric assays for mammalian epoxide hydrolases and glutathione S-transferase. Anal. Biochem. 131, 273-282.
29. Borhan, B., Mebrahtu, T., Nazarian, S., Kurth, M.J. & Hammock, B.D. (1995) Improved radiolabeled substrates for soluble epoxide hydrolase. Anal. Biochem. 231, 188-200.
30. Abdel-Aal, Y.A. & Hammock, B.D. (1986) Transition state analogs as ligands for affinity purification of juvenile hormone esterase. Science 233, 1073-1076.
31. Grant, D.F., Bender, D.M. & Hammock, B.D. (1989) Quantitative kinetic assays for glutathione S-transferase and general esterase in individual mosquitoes using an EIA reader. Insect. Biochem. 19, 741-751.
32. Zhu, Q., von Dippe, P., Xing, W. & Levy, D. (1999) Membrane topology and cell surface targeting of microsomal epoxide hydrolase. Evidence for multiple topological orientations. J. Biol. Chem. 274, 27898-27904.
33. Casas, J., Harshman, L.G., Messeguer, A., Kuwano, E. & Hammock, B.D. (1991) In vitro metabolism of juvenile hormone III and juvenile hormone III bisepoxide by Drosophila melanogaster and mammalian cytosolic epoxide hydrolase. Arch. Biochem. Biophys. 286, 153-158.
34. Khlebodarova, T.M., Gruntenko, N.E., Grenback, L.G., Sukhanova, M.Z., Mazurov, M.M., Rauschenbach, I.Y., Tomas, B.A. & Hammock, B.D. (1996) A comparative analysis of juvenile hormone metabolizing enzymes in two species of Drosophila during development. Insect Biochem. Mol. Biol. 26, 829-835.
35. Engström, Y. (1999) Induction and regulation of antimicrobial peptides in Drosophila. Dev. Comp. Immun. 23, 345-358.
36. Wasserman, W.W. & Fahl, W.E. (1997) Functional antioxidant responsive elements. Proc. Natl Acad. Sci. USA 94, 5361-5366.
37. Zhang, B., Marcus, S.L., Sajjadi, F.G., Alvares, K., Reddy, J.K., Subramani, S., Rachubinski, R.A. & Capone, J.P. (1992) Identification of a peroxisome proliferator-responsive element upstream of the gene encoding rat peroxisomal enoyl-coa hydratase/3-hydroxyacyl-coa dehydrogenase. Proc. Natl Acad. Sci. USA 89, 7541-7545.
38. He, J.-S. & Fulco, A.J. (1991) A barbiturate-regulated protein binding to a common sequence in the cytochrome p450 gene of rodents and bacteria. J. Biol. Chem. 266, 7864-7869.
39. Thompson, J.D., Gibson, T.J., Plewniak, F., Jeanmougin, F. & Higgins, D.G. (1997) The ClustalX windows interface: flexible strategies for multiple sequence alignment aided by quality analysis tools. Nucl. Acids Res. 24, 4876-4882.
40. Saitou, N. & Nei, M. (1987) The neighbor-joining method: a new method for reconstructing phylogenetic trees. Mol. Biol. Evol. 4, 406-425.