Epoxide hydrolases: biochemistry and molecular biology
Tóm tắt
Từ khóa
Tài liệu tham khảo
Nashed, 1985, Properties of liver microsomal cholesterol 5,6-oxide hydrolase, Arch. Biochem. Biophys., 241, 149, 10.1016/0003-9861(85)90371-6
Astrom, 1986, Subcellular and organ distribution of cholesterol epoxide hydrolase in the rat, Biochim. Biophys. Acta, 882, 359, 10.1016/0304-4165(86)90259-X
Finley, 1988, Increased cholesterol epoxide hydrolase activity in clofibrate-fed animals, Biochem. Pharmacol., 37, 3169, 10.1016/0006-2952(88)90316-4
Levin, 1983, Distinct rat hepatic microsomal epoxide hydrolases catalyze the hydration of cholesterol 5,6 α-oxide and certain xenobiotic alkene and arene oxides, Arch. Biochem. Biophys., 220, 485, 10.1016/0003-9861(83)90439-3
Muller, 1997, Visualization of a covalent intermediate between microsomal epoxide hydrolase, but not cholesterol epoxide hydrolase, and their substrates, Eur. J. Biochem., 245, 490, 10.1111/j.1432-1033.1997.00490.x
Sevanian, 1986, Catalytic properties and inhibition of hepatic cholesterol-epoxide hydrolase, J. Biol. Chem., 261, 54, 10.1016/S0021-9258(17)42429-X
Sevanian, 1984, Cholesterol epoxide is a direct-acting mutagen, Proc. Natl. Acad. Sci. USA, 81, 4198, 10.1073/pnas.81.13.4198
Sevanian, 1986, The cytotoxic and mutagenic properties of cholesterol oxidation products, Food Chem. Toxicol., 24, 1103, 10.1016/0278-6915(86)90295-4
Nashed, 1986, 7-Dehydrocholesterol 5,6 α-oxide as a mechanism-based inhibitor of microsomal cholesterol oxide hydrolase, J. Biol. Chem., 261, 2510, 10.1016/S0021-9258(17)35815-5
Watabe, 1983, Mouse liver microsomal cholesterol epoxide hydrolase: a specific inhibition of its activity by 5,6 α-imino-5 α-cholestan-3 α-OL, Chem. Biol. Interact., 44, 143, 10.1016/0009-2797(83)90136-9
Pace-Asciak, 1989, Purification of hepoxilin epoxide hydrolase from rat liver, J. Biol. Chem., 264, 9310, 10.1016/S0021-9258(18)60532-0
Pace-Asciak, 1994, Hepoxilins: a review on their cellular actions, Biochim. Biophys. Acta, 1215, 1, 10.1016/0005-2760(94)90087-6
Reynaud, 1994, Hepoxilin A3 formation in the rat pineal gland selectively utilizes (12S)-hydroperoxyeicosatetraenoic acid (HPETE), but not (12R)-HPETE, J. Biol. Chem., 269, 23976, 10.1016/S0021-9258(19)51034-1
Laneuville, 1991, Hepoxilin A3 (HxA3) is formed by the rat aorta and is metabolized into HxA3-C, a glutathione conjugate, Biochim. Biophys. Acta, 1084, 60, 10.1016/0005-2760(91)90056-N
Reynaud, 1999, Hepoxilin signaling in intact human neutrophils: biphasic elevation of intracellular calcium by unesterified hepoxilin A3, FEBS Lett., 446, 236, 10.1016/S0014-5793(99)00225-2
Margalit, 1993, Hepoxilin A3 is the endogenous lipid mediator opposing hypotonic swelling of intact human platelets, Proc. Natl. Acad. Sci. USA, 90, 2589, 10.1073/pnas.90.7.2589
Haeggstrom, 1994, Novel structural and functional properties of leukotriene A4 hydrolase. Implications for the development of enzyme inhibitors, Adv. Prostaglandin Thromb. Leukot. Res., 22, 3
Mancini, 1995, Cloning and characterization of the human leukotriene A4 hydrolase gene, Eur. J. Biochem., 231, 65, 10.1111/j.1432-1033.1995.tb20671.x
Jendraschak, 1996, The human leukotriene A4 hydrolase gene is expressed in two alternatively spliced mRNA forms, Biochem. J., 314, 733, 10.1042/bj3140733
E. Jendraschak, W.E. Kaminski, Isolation of human promoter regions by Alu repeat consensus-based polymerase chain reaction, Genomics 50 (1998) 53–60.
Fu, 1989, Leukotriene A4 hydrolase: analysis of some human tissues by radioimmunoassay, Biochim. Biophys. Acta, 1006, 121, 10.1016/0005-2760(89)90332-9
McGee, 1985, Enzymatic hydration of leukotriene A4. Purification and characterization of a novel epoxide hydrolase from human erythrocytes, J. Biol. Chem., 260, 12832, 10.1016/S0021-9258(17)38953-6
Rybina, 1997, Regulation of leukotriene A4 hydrolase activity in endothelial cells by phosphorylation, J. Biol. Chem., 272, 31865, 10.1074/jbc.272.50.31865
Haeggstrom, 2000, Structure, function, and regulation of leukotriene A4 hydrolase, Am. J. Respir. Crit. Care Med., 161, S25, 10.1164/ajrccm.161.supplement_1.ltta-6
Wetterholm, 1994, Zinc and other divalent cations inhibit purified leukotriene A4 hydrolase and leukotriene B4 biosynthesis in human polymorphonuclear leukocytes, Arch. Biochem. Biophys., 311, 263, 10.1006/abbi.1994.1236
Yuan, 1993, Development of selective tight-binding inhibitors of leukotriene A4 hydrolase, J. Med. Chem., 36, 211, 10.1021/jm00054a004
Andberg, 2000, Leukotriene A4 hydrolase: a critical role of glutamic acid-296 for the binding of bestatin, Biochem. J., 345, 621, 10.1042/bj3450621
G.M. Habib, A.A. Cuevas, R. Barrios, M.W. Lieberman, Mouse leukotriene A4 hydrolase is expressed at high levels in intestinal crypt cells and splenic lymphocytes, Gene 234 (1999) 249–255.
Blomster, 1995, Evidence for a catalytic role of tyrosine 383 in the peptidase reaction of leukotriene A4 hydrolase, Eur. J. Biochem., 231, 528, 10.1111/j.1432-1033.1995.0528d.x
Haeggstrom, 1993, Leukotriene A4 hydrolase: structural and functional properties of the active center, J. Lipid Mediat., 6, 1
Andberg, 1999, Evidence for a carbocation intermediate in the enzymatic transformation of leukotriene A4 into leukotriene B4, Adv. Exp. Med. Biol., 469, 319, 10.1007/978-1-4615-4793-8_47
Beetham, 1995, Gene evolution of epoxide hydrolases and recommended nomenclature, DNA Cell Biol., 14, 61, 10.1089/dna.1995.14.61
Meijer, 1988, Cytosolic epoxide hydrolase, Chem. Biol. Interact., 64, 207, 10.1016/0009-2797(88)90100-7
Schladt, 1988, Purification and characterization of rat-liver cytosolic epoxide hydrolase, Eur. J. Biochem., 176, 31, 10.1111/j.1432-1033.1988.tb14247.x
Schladt, 1988, Human liver cytosolic epoxide hydrolases, Eur. J. Biochem., 176, 715, 10.1111/j.1432-1033.1988.tb14335.x
Beetham, 1993, cDNA cloning and expression of a soluble epoxide hydrolase from human liver, Arch. Biochem. Biophys., 305, 197, 10.1006/abbi.1993.1411
Thomas, 1990, Rat and human liver cytosolic epoxide hydrolases: evidence for multiple forms at level of protein and mRNA, Environ. Health Perspect., 88, 49
Schladt, 1986, Distribution and inducibility of cytosolic epoxide hydrolase in male Sprague–Dawley rats, Biochem. Pharmacol., 35, 3309, 10.1016/0006-2952(86)90428-4
Arand, 1991, An impaired peroxisomal targeting sequence leading to an unusual bicompartmental distribution of cytosolic epoxide hydrolase, FEBS Lett., 294, 19, 10.1016/0014-5793(91)81333-4
Eriksson, 1991, Studies on the intracellular distributions of soluble epoxide hydrolase and of catalase by digitonin-permeabilization of hepatocytes isolated from control and clofibrate-treated mice, Eur. J. Biochem., 198, 471, 10.1111/j.1432-1033.1991.tb16037.x
Grant, 1993, Molecular cloning and expression of murine liver soluble epoxide hydrolase, J. Biol. Chem., 268, 17628, 10.1016/S0021-9258(19)85378-4
Knehr, 1993, Isolation and characterization of a cDNA encoding rat liver cytosolic epoxide hydrolase and its functional expression in Escherichia coli, J. Biol. Chem., 268, 17623, 10.1016/S0021-9258(19)85377-2
Sandberg, 1996, Structural characterization of the human soluble epoxide hydrolase gene (EPHX2), Biochem. Biophys. Res. Commun., 221, 333, 10.1006/bbrc.1996.0596
Stapleton, 1994, Cloning and expression of soluble epoxide hydrolase from potato, Plant J., 6, 251, 10.1046/j.1365-313X.1994.6020251.x
Vesell, 1991, Genetic factors that regulate cytosolic epoxide hydrolase activity in normal human lymphocytes, Ann. Genet., 34, 167
M. Sandberg, C. Hassett, J. Meijer, E.T. Adman, C.J. Omiecinski, Identification and functional characterization of human soluble epoxide hydrolase genetic polymorphisms, J. Biol. Chem. 275 (2000) 28873–28881.
Johansson, 1995, Tissue specific basal expression of soluble murine epoxide hydrolase and effects of clofibrate on the mRNA levels in extrahepatic tissues and liver, Arch. Toxicol., 70, 61, 10.1007/s002040050250
Lundgren, 1987, Induction of cytosolic and microsomal epoxide hydrolases and proliferation of peroxisomes 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, 10.1016/0006-2952(87)90169-9
Lundgren, 1988, Induction of cytosolic and microsomal epoxide hydrolases in mouse liver by peroxisome proliferators, with special emphasis on structural analogues of 2-ethylhexanoic acid, Chem. Biol. Interact., 68, 219, 10.1016/0009-2797(88)90018-X
B. Lundgren, J.W. DePierre, 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 (1989) 867–881.
Oesch, 1986, Rat cytosolic epoxide hydrolase, Adv. Exp. Med. Biol., 197, 195, 10.1007/978-1-4684-5134-4_16
Zeldin, 1995, Metabolism of epoxyeicosatrienoic acids by cytosolic epoxide hydrolase: substrate structural determinants of asymmetric catalysis, Arch. Biochem. Biophys., 316, 443, 10.1006/abbi.1995.1059
Borhan, 1995, Improved radiolabeled substrates for soluble epoxide hydrolase, Anal. Biochem., 231, 188, 10.1006/abio.1995.1520
Dietze, 1994, Spectrophotometric substrates for cytosolic epoxide hydrolase, Anal. Biochem., 216, 176, 10.1006/abio.1994.1023
Nourooz Zadeh, 1992, Characterization of the cytosolic epoxide hydrolase-catalyzed hydration products from 9,10:12,13-diepoxy stearic esters, Arch. Biochem. Biophys., 294, 675, 10.1016/0003-9861(92)90741-E
Zeldin, 1993, Regio- and enantiofacial selectivity of epoxyeicosatrienoic acid hydration by cytosolic epoxide hydrolase, J. Biol. Chem., 268, 6402, 10.1016/S0021-9258(18)53266-X
Moghaddam, 1997, Bioactivation of leukotoxins to their toxic diols by epoxide hydrolase, Nat. Med., 3, 562, 10.1038/nm0597-562
Miyamoto, 1987, Inhibition of epoxide hydrolases and glutathione S-transferases by 2-, 3-, and 4-substituted derivatives of 4′-phenylchalcone and its oxide, Arch. Biochem. Biophys., 254, 203, 10.1016/0003-9861(87)90096-8
Dietze, 1991, Inhibition of cytosolic epoxide hydrolase by trans-3-phenylglycidols, Biochem. Pharmacol., 42, 1163, 10.1016/0006-2952(91)90250-9
Dietze, 1993, Inhibition of epoxide hydrolase from human, monkey, bovine, rabbit and murine liver by trans-3-phenylglycidols, Comp. Biochem. Physiol. B, 104, 309, 10.1016/0305-0491(93)90373-D
Morisseau, 1999, Potent urea and carbamate inhibitors of soluble epoxide hydrolases, Proc. Natl. Acad. Sci. USA, 96, 8849, 10.1073/pnas.96.16.8849
Draper, 1999, Inhibition of soluble and microsomal epoxide hydrolase by zinc and other metals, Toxicol. Sci., 52, 26, 10.1093/toxsci/52.1.26
Fisslthaler, 1999, Cytochrome P450 2C is an EDHF synthase in coronary arteries, Nature, 401, 493, 10.1038/46816
Fisslthaler, 2000, EDHF: a cytochrome P450 metabolite in coronary arteries, Semin. Perinatol., 24, 15, 10.1016/S0146-0005(00)80048-8
Weintraub, 1999, Epoxide hydrolases regulate epoxyeicosatrienoic acid incorporation into coronary endothelial phospholipids, Am. J. Physiol., 277, H2098
Arand, 1994, Sequence similarity of mammalian epoxide hydrolases to the bacterial haloalkane dehalogenase and other related proteins. Implication for the potential catalytic mechanism of enzymatic epoxide hydrolysis, FEBS Lett., 338, 251, 10.1016/0014-5793(94)80278-5
Pinot, 1995, Molecular and biochemical evidence for the involvement of the Asp-333-His-523 pair in the catalytic mechanism of soluble epoxide hydrolase, J. Biol. Chem., 270, 7968, 10.1074/jbc.270.14.7968
Borhan, 1995, Mechanism of soluble epoxide hydrolase. Formation of an alpha-hydroxy ester-enzyme intermediate through Asp-333, J. Biol. Chem., 270, 26923, 10.1074/jbc.270.45.26923
Arand, 1996, Asp333, Asp495, and His523 form the catalytic triad of rat soluble epoxide hydrolase, J. Biol. Chem., 271, 4223, 10.1074/jbc.271.8.4223
Argiriadi, 1999, Detoxification of environmental mutagens and carcinogens: structure, mechanism and evolution of liver epoxide hydrolase, Proc. Natl. Acad. Sci. USA, 96, 10637, 10.1073/pnas.96.19.10637
M. Shou, F.J. Gonzalez, H.V. Gelboin, 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.
F.P. Guengerich, Epoxide hydrolase: properties and metabolic roles, Rev. Biochem. Toxicol. 4 (1982) 5–30.
Armstrong, 1987, Enzyme-catalyzed detoxication reactions: mechanisms and stereochemistry, CRC Crit. Rev. Biochem., 22, 39, 10.3109/10409238709082547
Omiecinski, 1993, Human peripheral lymphocytes as indicators of microsomal epoxide hydrolase activity in liver and lung, Pharmacogenetics, 3, 150, 10.1097/00008571-199306000-00005
Papadopoulos, 1994, Purification and initial characterization of microsomal epoxide hydrolase from the human adrenal gland, Biochim. Biophys. Acta, 1206, 253, 10.1016/0167-4838(94)90216-X
Hassett, 1989, Rabbit microsomal epoxide hydrolase: isolation and characterization of the xenobiotic metabolizing enzyme cDNA, Arch. Biochem. Biophys., 271, 380, 10.1016/0003-9861(89)90287-7
Skoda, 1988, Human microsomal xenobiotic epoxide hydrolase. Complementary DNA sequence, complementary DNA-directed expression in COS-1 cells, and chromosomal localization, J. Biol. Chem., 263, 1549, 10.1016/S0021-9258(19)57339-2
Bulleid, 1986, Microsomal epoxide hydrolase of rat liver. Purification and characterization of enzyme fractions with different chromatographic characteristics, Biochem. J., 233, 607, 10.1042/bj2330607
C. Hassett, K.B. Robinson, N.B. Beck, C.J. Omiecinski, The human microsomal epoxide hydrolase gene (EPHX1): complete nucleotide sequence and structural characterization, Genomics 23 (1994) 433–442.
Wilson, 1989, Xenobiotic microsomal epoxide hydrolase: 5′ sequence of the human gene, Biochim. Biophys. Acta, 1008, 357, 10.1016/0167-4781(89)90029-8
Hassett, 1998, Effects of chemical inducers on human microsomal epoxide hydrolase in primary hepatocyte cultures, Biochem. Pharmacol., 55, 1059, 10.1016/S0006-2952(97)00679-5
A. Astrom, S. Man'er, J.W. DePierre, Induction of liver microsomal epoxide hydrolase, UDP-glucuronyl transferase and cytosolic glutathione transferase in different rodent species by 2-acetylaminofluorene or 3-methylcholanthrene, Xenobiotica 17 (1987) 155–163.
Cho, 1998, Differential induction of rat hepatic microsomal epoxide hydrolase and rGSTA2 by diazines: the role of cytochrome P450 2E1-mediated metabolic activation, Chem. Biol. Interact., 116, 229, 10.1016/S0009-2797(98)00093-3
Craft, 1988, Induction of microsomal epoxide hydrolase by nitrosamines in rat liver. Effect on messenger ribonucleic acids, Biochem. Pharmacol., 37, 297, 10.1016/0006-2952(88)90732-0
A. Parkinson, P.E. Thomas, D.E. Ryan, W. Levin, T. Fujita, S. Safe, Induction of rat liver microsomal cytochrome P-450 isozymes and epoxide hydrolase by a series of 4′-substituted-2,3,4,5-tetrachlorobiphenyls, Toxicology 53 (1988) 289–300.
Bell, 1990, Glucocorticoid repression and basal regulation of the epoxide hydrolase promoter, Arch. Biochem. Biophys., 279, 363, 10.1016/0003-9861(90)90503-Q
Gaedigk, 1994, Characterization of the microsomal epoxide hydrolase gene in patients with anticonvulsant adverse drug reactions, Pharmacogenetics, 4, 142, 10.1097/00008571-199406000-00005
Hassett, 1994, Human microsomal epoxide hydrolase: genetic polymorphism and functional expression in vitro of amino acid variants, Hum. Mol. Genet., 3, 421, 10.1093/hmg/3.3.421
Laurenzana, 1998, Post-transcriptional regulation of human microsomal epoxide hydrolase, Pharmacogenetics, 8, 157, 10.1097/00008571-199804000-00008
Hassett, 1997, Human hepatic microsomal epoxide hydrolase: comparative analysis of polymorphic expression, Arch. Biochem. Biophys., 337, 275, 10.1006/abbi.1996.9794
S. Raaka, C. Hassett, C.J. Omiencinski, Human microsomal epoxide hydrolase: 5′-flanking region genetic polymorphisms, Carcinogenesis 19 (1998) 387–393.
M.W. Himmelstein, M.J. Turner, B. Asgharian, J.A. Bond, Comparison of blood concentrations of 1,3-butadiene and butadiene epoxides in mice and rats exposed to 1,3-butadiene by inhalation, Carcinogenesis 15 (1994) 1479–1486.
Krause, 1997, Oxidation of butadiene monoxide to meso- and (+/−)-diepoxybutane by cDNA-expressed human cytochrome P450s and by mouse, rat, and human liver microsomes: evidence for preferential hydration of meso-diepoxybutane in rat and human liver microsomes, Arch. Biochem. Biophys., 337, 176, 10.1006/abbi.1996.9781
Krause, 1997, Epoxide hydrolase-dependent metabolism of butadiene monoxide to 3-butene-1,2-diol in mouse, rat, and human liver, Drug Metab. Dispos., 25, 1013
A.B. Lindstrom, K. Yeowell-O'Connell, S. Waidyanatha, B.T. Golding, V.R. Tornero, S.M. Rappaport, Measurement of benzene oxide in the blood of rats following administration of benzene, Carcinogenesis 18 (1997) 1637–1641.
Guengerich, 1998, Activation and detoxication of aflatoxin B1, Mutat. Res., 402, 121, 10.1016/S0027-5107(97)00289-3
Guengerich, 1999, Kinetics of hydrolysis and reaction of aflatoxin B1 exo-8,9-epoxide and relevance to toxicity and detoxication, Drug Metab. Rev., 31, 141, 10.1081/DMR-100101911
J.M. Walters, R.D. Combes, Activation of benzo[a]pyrene and aflatoxin B1 to mutagenic chemical species by microsomal preparations from rat liver and small intestine in relation to microsomal epoxide hydrolase, Mutagenesis 1 (1986) 45–48.
H. Glatt, C. Wameling, S. Elsberg, H. Thomas, H. Marquardt, A. Hewer, D.H. Phillips, F. Oesch, A. Seidel, Genotoxicity characteristics of reverse diol-epoxides of chrysene, Carcinogenesis 14 (1993) 11–19.
Yang, 1987, Stereoselective formations of K-region and non-K-region epoxides in the metabolism of chrysene by rat liver microsomal cytochrome P-450 isozymes, Mol. Pharmacol., 32, 73
R.H. Heflich, J.R. Thornton Manning, T. Kinouchi, F.A. Beland, Mutagenicity of oxidized microsomal metabolites of 1-nitropyrene in Chinese hamster ovary cells, Multagenesis 5 (1990) 151–157.
van Bladeren, 1985, Differential stereoselectivity of cytochromes P-450b and P-450c in the formation of naphthalene and anthracene 1,2-oxides. The role of epoxide hydrolase in determining the enantiomer composition of the 1,2-dihydrodiols formed, J. Biol. Chem., 260, 10226, 10.1016/S0021-9258(17)39235-9
M. Hall, D.K. Parker, A.J. Hewer, D.H. Phillips, P.L. Grover, Further metabolism of diol-epoxides of chrysene and dibenz[a,c]anthracene to DNA binding species as evidenced by 32P-postlabelling analysis, Carcinogenesis 9 (1988) 865–868.
Miyata, 1999, Targeted disruption of the microsomal epoxide hydrolase gene. Microsomal epoxide hydrolase is required for the carcinogenic activity of 7,12-dimethylbenz[a]anthracene, J. Biol. Chem., 274, 23963, 10.1074/jbc.274.34.23963
Bellucci, 1994, Kinetics and stereochemistry of the microsomal epoxide hydrolase-catalyzed hydrolysis of cis-stilbene oxides, Chirality, 6, 577, 10.1002/chir.530060711
Kitteringham, 1996, Interindividual and interspecies variation in hepatic microsomal epoxide hydrolase activity: studies with cis-stilbene oxide, carbamazepine 10, 11-epoxide and naphthalene, J. Pharmacol. Exp. Ther., 278, 1018
Moody, 1987, Purification of microsomal epoxide hydrolase from liver of rhesus monkey: partial separation of cis- and trans-stilbene oxide hydrolase, Arch. Biochem. Biophys., 258, 156, 10.1016/0003-9861(87)90332-8
Carlson, 1998, Metabolism of styrene oxide to styrene glycol by mouse liver and lung, J. Toxicol. Environ. Health, 53, 19, 10.1080/009841098159448
Gadberry, 1996, Pneumotoxicity and hepatotoxicity of styrene and styrene oxide, J. Toxicol. Environ. Health, 48, 273, 10.1080/009841096161339
Herrero, 1997, Recombinant expression of human microsomal epoxide hydrolase protects V79 Chinese hamster cells from styrene oxide- but not from ethylene oxide-induced DNA strand breaks, Environ. Mol. Mutagen., 30, 429, 10.1002/(SICI)1098-2280(1997)30:4<429::AID-EM8>3.0.CO;2-D
Hartsfield, 1995, Phenytoin embryopathy: effect of epoxide hydrolase inhibitor on phenytoin exposure in utero in C57BL/6J mice, Biochem. Mol. Med., 56, 131, 10.1006/bmme.1995.1068
Riley, 1988, An in vitro study of the microsomal metabolism and cellular toxicity of phenytoin, sorbinil and mianserin, Br. J. Clin. Pharmacol., 26, 577, 10.1111/j.1365-2125.1988.tb05298.x
Van Dyke, 1991, Differences in phenytoin biotransformation and susceptibility to congenital malformations: a review, DICP, 25, 987, 10.1177/106002809102500914
Bellucci, 1987, The metabolism of carbamazepine in humans: steric course of the enzymatic hydrolysis of the 10,11-epoxide, J. Med. Chem., 30, 768, 10.1021/jm00388a004
Eugster, 1991, Heterologous expression of human microsomal epoxide hydrolase in Saccharomyces cerevisiae. Study of the valpromide–carbamazepine epoxide interaction, Biochem. Pharmacol., 42, 1367, 10.1016/0006-2952(91)90447-D
Vogel, 1982, Endogenous role of microsomal epoxide hydrolase. Ontogenesis, induction inhibition, tissue distribution, immunological behaviour and purification of microsomal epoxide hydrolase with 16α, 17α-epoxyandrostene-3-one as substrate, Eur. J. Biochem., 126, 425, 10.1111/j.1432-1033.1982.tb06797.x
Papadopoulos, 1985, Subcellular distribution, catalytic properties and partial purification of epoxide hydrolase in the human adrenal gland, Chem. Biol. Interact., 55, 249, 10.1016/S0009-2797(85)80133-2
Prestwich, 1985, Cyclopropyl oxiranes: reversible inhibitors of cytosolic and microsomal epoxide hydrolases, Arch. Biochem. Biophys., 237, 361, 10.1016/0003-9861(85)90288-7
Leeder, 1992, Human anti-cytochrome P450 antibodies in aromatic anticonvulsant-induced hypersensitivity reactions, J. Pharmacol. Exp. Ther., 263, 360
Shear, 1988, Anticonvulsant hypersensitivity syndrome. In vitro assessment of risk, J. Clin. Invest., 82, 1826, 10.1172/JCI113798
Green, 1995, Genetic analysis of microsomal epoxide hydrolase in patients with carbamazepine hypersensitivity, Biochem. Pharmacol., 50, 1353, 10.1016/0006-2952(95)02009-8
Leeder, 1996, Epitope mapping studies with human anti-cytochrome P450 3A antibodies, Mol. Pharmacol., 49, 234
Benhamou, 1998, Association between lung cancer and microsomal epoxide hydrolase genotypes, Cancer Res., 58, 5291
Hulla, 1999, Symposium overview: the role of genetic polymorphism and repair deficiencies in environmental disease, Toxicol. Sci., 47, 135, 10.1093/toxsci/47.2.135
Lin, 2000, Association of CYP1A1 and microsomal epoxide hydrolase polymorphisms with lung squamous cell carcinoma, Br. J. Cancer, 82, 852, 10.1054/bjoc.1999.1011
Harrison, 1999, Microsomal epoxide hydrolase gene polymorphism and susceptibility to colon cancer, Br. J. Cancer, 79, 168, 10.1038/sj.bjc.6690028
Hengstler, 1998, Polymorphisms of N-acetyltransferases, glutathione S-transferases, microsomal epoxide hydrolase and sulfotransferases: influence on cancer susceptibility, Recent Results Cancer Res., 154, 47, 10.1007/978-3-642-46870-4_4
L.T. Laughlin, H.F. Tzeng, S. Lin, R.N. Armstrong, Mechanism of microsomal epoxide hydrolase, semifunctional site-specific mutants affecting the alkylation half-reaction, Biochemistry 37 (1998) 2897–2904.
Arand, 1999, Catalytic triad of microsomal epoxide hydrolase: replacement of Glu404 with Asp leads to a strongly increased turnover rate, Biochem. J., 337, 37, 10.1042/bj3370037
Bell, 1993, Expression of rat microsomal epoxide hydrolase in Escherichia coli. Identification of a histidyl residue essential for catalysis, J. Biol. Chem., 268, 14011, 10.1016/S0021-9258(19)85202-X
Lacourciere, 1994, Microsomal and soluble epoxide hydrolases are members of the same family of CX bond hydrolase enzymes, Chem. Res. Toxicol., 7, 121, 10.1021/tx00038a001
Arand, 1999, Cloning and molecular characterization of a soluble epoxide hydrolase from Aspergillus niger that is related to mammalian microsomal epoxide hydrolase, Biochem. J., 344, 273, 10.1042/bj3440273