| Name | microsomal epoxide hydrolase |
|---|---|
| Synonyms | EPHX; EPHX 1; EPHX1; EPHX1 protein; EPOX; Epoxide hydratase; Epoxide hydrolase; Epoxide hydrolase 1… |
| Name | 1-naphthol |
|---|---|
| CAS | 1-naphthalenol |
| PubMed | Abstract | RScore(About this table) | |
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| 2749733 | Wells PG, Wilson B, Lubek BM: In vivo murine studies on the biochemical mechanism of naphthalene cataractogenesis. Toxicol Appl Pharmacol. 1989 Jul;99(3):466-73. Naphthalene cataractogenicity was enhanced by pretreatment with the cytochrome P450 inducer phenobarbital and the GSH depletor diethyl (DEM) (p less than 0.05), and was unaffected by pretreatment with the prostaglandin synthetase inhibitors or or the epoxide hydrolase inhibitor trichloropropene oxide. NQ cataractogenicity was enhanced by pretreatment with DEM (p less than 0.05). 1-Naphthol (56 to 562 mg/kg ip) demonstrated a cataractogenic potency intermediary to that for naphthalene and NQ. |
1(0,0,0,1) | Details |
| 16906435 | Elovaara E, Mikkola J, Stockmann-Juvala H, Luukkanen L, Keski-Hynnila H, Kostiainen R, Pasanen M, Pelkonen O, Vainio H: Polycyclic aromatic hydrocarbon (PAH) metabolizing enzyme activities in human lung, and their inducibility by exposure to naphthalene, phenanthrene, pyrene, chrysene, and benzo (a) pyrene as shown in the rat lung and liver. Arch Toxicol. 2007 Mar;81(3):169-82. Epub 2006 Aug 12. Epoxide hydrolase activity was 1,000-fold higher than the pulmonary CYP1A1 activities. PAH treatment increased the CYP1A-catalyzed activity of pyrene 1-hydroxylation and 7-ethoxyresorufin O-deethylation in rat liver by up to 28- and 279-fold, and in rat lung by up to 22- and 51-fold, respectively. 1-Naphthol (hUGT1A6), 1-hydroxypyrene (hUGT1A6/1A9), and entacapone (hUGT1A9) are markers of PAH-glucuronidating human uridine diphosphate-glucuronosyltransferases (UGT). |
1(0,0,0,1) | Details |
| 12524029 | Sivapathasundaram S, Sauer MJ, Ioannides C: Xenobiotic conjugation systems in deer compared with cattle and rat. Comp Biochem Physiol C Toxicol Pharmacol. 2003 Jan;134(1):169-73. Hepatic microsomal epoxide hydrolase activity in cattle and deer, determined using benzo [a] pyrene 4,5-oxide as substrate, was nearly twice that of the rat. |
1(0,0,0,1) | Details |
| 3111481 | Grant MH, Burke MD, Hawksworth GM, Duthie SJ, Engeset J, Petrie JC: Human adult hepatocytes in primary monolayer culture. Biochem Pharmacol. 1987 Jul 15;36(14):2311-6. Epoxide hydrolase (EH) showed a large transient increase (2-5-fold) in enzyme activity 24 hr after culture, declining to fresh cell values by 48 hr. UDP-glucuronyltransferase (GT) activity towards phenolphthalein and 1-naphthol also increased (2-3-fold) during the 72 hr of culture, the greater and more rapid increase being observed with phenolphthalein glucuronidation. |
1(0,0,0,1) | Details |
| 2847753 | Grant MH, Duthie SJ, Gray AG, Burke MD: Mixed function oxidase and UDP-glucuronyltransferase activities in the human Hep G2 hepatoma cell line. Biochem Pharmacol. 1988 Nov 1;37(21):4111-6. In cultured human hepatoma cells phenolphthalein glucuronidation was increased 3-fold by 2 mM phenobarbitone (PB) in the culture medium but not by 25 microM benz (a) anthracene (BA), while 1-naphthol glucuronidation was not increased by either PB or BA. Control Hep G2 cells had similar conjugation and cytochrome reductase activities to freshly isolated human adult hepatocytes, but had lower O-dealkylation and elevated microsomal epoxide hydrolase activities. |
1(0,0,0,1) | Details |
| 1410423 | Ghersi-Egea JF, Leininger-Muller B, Minn A, Siest G: Drug metabolizing enzymes in the rat pituitary gland. . Prog Brain Res. 1992;91:373-8. Similarly, microsomal epoxide hydrolase, which inactivates reactive epoxides to trans diol molecules, and two conjugating enzymes, 1-naphthol UDP-glucuronosyltransferase and glutathione-S-transferase, display respectively 6, 4 and 7 times higher activities in the pituitary gland. 7-Benzoxyresorufin-O-dealkylase, 1-naphthol UDP-glucuronosyltransferase and membrane-bound epoxide hydrolase activities were significantly increased in the pituitary gland as an adaptive response to an in vivo treatment by an exogenous inducer, 3-methylcholanthrene. |
81(1,1,1,1) | Details |
| 8240407 | Tingle MD, Pirmohamed M, Templeton E, Wilson AS, Madden S, Kitteringham NR, Park BK: An investigation of the formation of cytotoxic, genotoxic, protein-reactive and stable metabolites from naphthalene by human liver microsomes. Biochem Pharmacol. 1993 Nov 2;46(9):1529-38. Trichloropropene oxide (TCPO; 30 microM), an epoxide hydrolase inhibitor, increased the human liver microsomal-dependent cytotoxicity (19.6 +/- 0.9% vs 28.7 +/- 1.0%; P = 0.02) and covalent binding to protein (1.4 +/- 0.3% vs 2.8 +/- 0.2%; P = 0.03) of naphthalene (100 microM), and reversed the 1,2-dihydrodiol to 1-naphthol ratio from 6.6 (without TCPO) to 2.6, 0.6 and 0.1 at TCPO concentrations of 30, 100 and 500 microM, respectively. |
62(0,2,2,2) | Details |
| 2885979 | Fournel S, Magdalou J, Pinon P, Siest G: Differential induction profile of drug-metabolizing enzymes after treatment with hypolipidaemic agents. Xenobiotica. 1987 Apr;17(4):445-57. It dramatically enhanced the epoxide hydrolase activity (7.6-fold), and increased (200%) the glucuronidation of planar group I substrates 4-methylumbelliferone, 1-naphthol). |
33(0,1,1,3) | Details |
| 3131610 | Ghersi-Egea JF, Minn A, Siest G: A new aspect of the protective functions of the blood-brain barrier: activities of four drug-metabolizing enzymes in isolated rat brain microvessels. Life Sci. 1988;42(24):2515-23. We measured the activities of some enzymes involved in the metabolism of lipophilic xenobiotics, i.e. cytochrome P-450-linked monooxygenases, epoxide hydrolase, NADPH:cytochrome P-450 reductase and 1-naphthol UDP-glucuronosyl transferase in isolated rat brain microvessels. |
31(0,1,1,1) | Details |
| 3240719 | Jagadeesan V, Oesch F: Effects of dietary zinc deficiency on the activity of enzymes associated with phase I and II of drug metabolism in Fischer-344 rats: activities of drug metabolising enzymes in zinc deficiency. Drug Nutr Interact. 1988;5(4):403-13. It was observed that the activities of microsomal epoxide hydrolase (with benz (a) pyrene 4-5 oxide as substrate), diphospho glucuronyl transferase (with 1-naphthol as substrate) and cytosolic glutathione-S-transferase (with chlorodinitrobenzene as substrate) were altered exclusively due to zinc deficiency. |
31(0,1,1,1) | Details |
| 8619256 | Slawson MH, Franklin MR, Moody DE: Correlations of the induction of microsomal epoxide hydrolase activity with phase II drug conjugating enzyme activities in rat liver. Toxicol Lett. 1996 Apr;85(1):29-34. Within the selective induction of phase II enzymes following treatment with dipyridyls or N-heterocyclic analogs of phenanthrene, strong correlations (r > or = 0.70) are observed between the increase of microsomal epoxide hydrolase (mEH) activity and UDP-glucuronosyltransferase (UGT) activities towards 1-naphthol and morphine. |
7(0,0,1,2) | Details |
| 7157840 | Pacifici GM, Davies DS, Whyte C, Boobis AR: Tissue differences in the ontogeny of inducibility of drug-metabolizing enzymes by 3-methylcholanthrene in the rabbit. Xenobiotica. 1982 Sep;12(9):591-8. The effects of treatment of rabbits of different ages with 3-methylcholanthrene on cytochrome P-450 content, and benzo [a] pyrene hydroxylase, epoxide hydrolase, S-epoxide transferase, 1-naphthol glucuronyl transferase and morphine glucuronyl transferase activities of liver, kidney and lung have been investigated. 2. |
7(0,0,1,2) | Details |
| 1358578 | Franklin MR, Moody DE: Concomitant induction of microsomal epoxide hydrolase and UDP-glucuronosyltransferase activities by dipyridine compounds. Drug Metab Dispos. 1992 Sep-Oct;20(5):726-9. |
5(0,0,0,5) | Details |
| 9134007 | Le HT, Franklin MR: Selective induction of phase II drug metabolizing enzyme activities by quinolines and isoquinolines. Chem Biol Interact. 1997 Mar 14;103(3):167-78. Elevations of UDP-glucuronosyltransferase activities towards 1-naphthol, and morphine elicited by quinoline (1.9- to 2.7-fold), were greater than those elicited by isoquinoline (1.4- to 1.8-fold). Microsomal epoxide hydrolase activity was increased only by quinoline (2.7-fold). |
4(0,0,0,4) | Details |
| 3130250 | Ghersi-Egea JF, Walther B, Perrin R, Minn A, Siest G: Inducibility of rat brain drug-metabolizing enzymes. Eur J Drug Metab Pharmacokinet. 1987 Oct-Dec;12(4):263-5. On the other hand, the microsomal 1-naphthol-UDP-glucuronosyl transferase and epoxide hydrolase seemed to be non-inducible by 3-methylcholanthrene or by phenobarbital. |
6(0,0,1,1) | Details |
| 2840913 | Magdalou J, Totis M, Boiteux-Antoine AF, Fournel-Gigleux S, Siest G, Schladt L, Oesch F: Effect of 1-benzylimidazole on cytochromes P-450 induction and on the activities of epoxide hydrolases and UDP-glucuronosyltransferases in rat liver. Biochem Pharmacol. 1988 Sep 1;37(17):3297-304. The activities towards 4-methylumbelliferone, 1-naphthol, morphine or a monoterpenoid nopol, supported by two different isozymes were significantly increased only with the highest dose; meanwhile glucuronidation was 2-fold enhanced, whatever the dose used. |
3(0,0,0,3) | Details |
| 1936901 | Roques M, Bagrel D, Magdalou J, Siest G: Expression of arylhydrocarbon hydroxylase, epoxide hydrolases, glutathione S-transferase and UDP-glucuronosyltransferases in H5-6 hepatoma cells. Gen Pharmacol. 1991;22(4):677-84. These cells also glucuronidated 1-naphthol efficiently (6 nmol/min per mg) and, at a lower extent, (12 pmol/min per mg). 5. |
3(0,0,0,3) | Details |
| 8498089 | Franklin MR, Slawson MH, Moody DE: Selective induction of rat liver phase II enzymes by N-heterocycle analogues of phenanthrene: a response exhibiting high correlation between UDP-glucuronosyltransferase and microsomal epoxide hydrolase activities. Xenobiotica. 1993 Mar;23(3):267-77. The detergent-activated UDP-glucuronosyltransferase activities towards morphine, and 1-naphthol were increased up to five-, three- and two-fold of control respectively. |
3(0,0,0,3) | Details |
| 4051475 | Sotnichenko AI, Serdiuk OA, Starovoitov ML, Parfenov EA, Sukhanov VA: [Chromatographic method of determining membrane epoxide hydrolase activity]. Antibiot Med Biotekhnol. 1985 Jul;30(7):535-8. The quantitative determination of 9,10-dioxy-9,10-dihydrophenanthrene was performed according to the method of the internal standard by HPLC in aqueous a cetonitrile on octylsilica gel with fluorescent detection. 1-Naphthol was used as the internal standard. |
2(0,0,0,2) | Details |
| 3341022 | Souhaili-el Amri H, Fargetton X, Benoit E, Totis M, Batt AM: Inducing effect of albendazole on rat liver drug-metabolizing enzymes and metabolite pharmacokinetics. Toxicol Appl Pharmacol. 1988 Jan;92(1):141-9. UDP-glucuronosyltransferase (GT) type 1 activities (1-naphthol, 7-hydroxycoumarin, and 4-methylumbelliferone) were significantly higher than in control microsomes (3- to 4-fold), while GT type 2 activities and -GT remained unchanged. Microsomal epoxide hydrolase (benzo [a] pyrene oxide) increased 2-fold. |
2(0,0,0,2) | Details |
| 4062276 | Sotnichenko AI, Serdiuk OA, Kilesso TIu, Sukhanov VA, Saprin AN: [Determination of the epoxide hydrolase activity in the peripheral blood lymphocytes of mammals]. Antibiot Med Biotekhnol. 1985 Aug;30(8):584-8. For elimination of the enzyme latency the lymphocytes were solubilized with lubrol PX, a nonionic detergent. 9,10--9,10-dihydrophenanthrene was estimated quantitatively by the method of the internal standard (1-naphthol) after reversed phase HPLC. |
2(0,0,0,2) | Details |
| 2113070 | Pham MA, Magdalou J, Siest G, Lenoir MC, Bernard BA, Jamoulle JC, Shroot B: Reconstituted epidermis: a novel model for the study of drug metabolism in human epidermis. J Invest Dermatol. 1990 Jun;94(6):749-52. The homogenate fraction contained membrane-bound mixed-function oxydases (cytochrome P-450 dependent) involved in the O-dealkylation of 7-ethoxy-, 7-pentoxy-, and 7-benzoxyresorufin, cytochrome c (P-450) reductase, 5 alpha-reductase, and UDP-glucuronosyltransferases, which conjugate 1-naphthol and Additionally, the activity of two distinct forms of epoxide hydrolases, which hydrate cis- and trans-stilbene oxides, could be measured. |
1(0,0,0,1) | Details |
| 2500129 | Pham MA, Magdalou J, Totis M, Fournel-Gigleux S, Siest G, Hammock BD: Characterization of distinct forms of cytochromes P-450, epoxide metabolizing enzymes and UDP-glucuronosyltransferases in rat skin. Biochem Pharmacol. 1989 Jul 1;38(13):2187-94. Glucuronidation of 1-naphthol, but not of could be followed in the microsomal fraction. The presence of several isoforms was revealed from their activities towards selected substrates and from their cross immunoreactivity using antibodies raised against purified hepatic or renal cytochromes P-450, epoxide hydrolase and UDP-glucuronosyltransferases. |
1(0,0,0,1) | Details |
| 3140501 | Pacifici GM, Franchi M, Bencini C, Repetti F, Di Lascio N, Muraro GB: Tissue distribution of drug-metabolizing enzymes in humans. Xenobiotica. 1988 Jul;18(7):849-56. The activities of the ethoxycoumarin O-deethylase (ECOD), epoxide hydrolase (EH), UDP-glucuronyl transferase (GT), glutathione S-transferase (GST), acetyl transferase (AT) and sulphotransferase (ST) were measured in 6 liver, 8 lung, 8 kidney, 8 intestinal mucosa and 22 urinary bladder mucosa specimens from human subjects. EH and GT were studied with styrene oxide and 1-naphthol, respectively, as substrates, GST, AT and ST were studied with benzo (a) pyrene-4,5-oxide, and 2-naphthol, respectively. 2. |
1(0,0,0,1) | Details |
| 3090569 | Pacifici GM, Giuliani L, Calcaprina R: Glucuronidation of 1-naphthol in nuclear and microsomal fractions of the human intestine. Pharmacology. 1986;33(2):103-9. The epoxide hydrolase activity towards styrene oxide was measured in the same subcellular fractions; it was undetectable in the nuclear fraction, whereas it was 0.46 +/- 0.04 nmol/mg/min (mean +/- SEM) in the microsomal fraction. |
1(0,0,0,1) | Details |
| 9176741 | Le HT, Lamb JG, Franklin MR: Drug metabolizing enzyme induction by benzoquinolines, acridine, and quinacrine; tricyclic aromatic molecules containing a single heterocyclic J Biochem Toxicol. 1996;11(6):297-303. A similar pattern but of lesser magnitude was seen with glutathione S-transferase activity. 3,4-Benzoquinoline was the only agent to significantly increase microsomal epoxide hydrolase activity (2,3-fold). Acridine treatment increased UDP-glucuronosyltransferase activity toward morphine (47%), 1-naphthol (28%), (19%), and (19%). |
1(0,0,0,1) | Details |
| 8442765 | Ghersi-Egea JF, Perrin R, Leininger-Muller B, Grassiot MC, Jeandel C, Floquet J, Cuny G, Siest G, Minn A: Subcellular localization of cytochrome P450, and activities of several enzymes responsible for drug metabolism in the human brain. Biochem Pharmacol. 1993 Feb 9;45(3):647-58. The other drug-metabolizing enzymes catalysing functionalization and conjugation reactions, presented the following characteristics in human brain: (i) a low activity of NADPH-cytochrome P450 reductase, which also catalyses the reduction of some xenobiotics; (ii) a high specific activity of the membrane-bound epoxide hydrolase; (iii) among the enzymes catalysing conjugation reactions, 1-naphthol-UDP-glucuronosyltransferase activity was barely or not detectable, whereas the mean glutathione-S-transferase activity was 15 times higher than the activity measured in rat brain. The presence of several drug-metabolizing enzyme activities in human brain microvessels, and particularly the high activity of epoxide hydrolase, suggests a participation of these enzymes in the metabolic blood-brain barrier. |
1(0,0,0,1) | Details |
| 3717918 | Sotnichenko AI, Serdiuk OA, Sukhanov VA, Saprin AN: [Determination of phenathrene-9,10-epoxidase in the liver microsomes of rats. Antibiot Med Biotekhnol. 1986 Mar;31(3):196-9. The rate of the substrate epoxidation is measured with the help of HPLC reverse phase in accordance with the method of the internal standard (1-naphthol) by 9,10-dihydroxy-9,10-dihydrophenanthrene, a product of the intermediate epoxide hydrolysis. For rapid quantitative conversion of the formed 9,10-epoxy-9,10-dihydrophenanthrene endogenic epoxide hydrolase is used after selective termination of the monoxygenase reaction. |
1(0,0,0,1) | Details |
| 3929791 | Andersson T, Pesonen M, Johansson C: Differential induction of cytochrome P-450-dependent monooxygenase, epoxide hydrolase, glutathione transferase and UDP glucuronosyl transferase activities in the liver of the rainbow trout by beta-naphthoflavone or Clophen A50. Biochem Pharmacol. 1985 Sep 15;34(18):3309-14. Glutathione transferase activity towards 1-chloro 2,4 dinitrobenzene and UDP glucuronosyltransferase activities towards 1-naphthol and were increased 1.4 to 3.0-fold by beta-naphthoflavone or Clophen A50. |
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