Assessment of cytochrome P450 fluorometric substrates with rainbow trout and killifish exposed to dexamethasone, pregnenolone-16α-carbonitrile, rifampicin, and β-naphthoflavone

Aquatic Toxicology

Volumn 97, Issue 4, 2010, Pages 324-333

  Smith, Emily M ^a   Wilson, Joanna Y ^a  

^a MCMASTER UNIVERSITY   (Canada)

Author keywords

naphthoflavone; Cytochrome P450; Fish; Induction; Metabolism; Pharmaceuticals

Indexed keywords

16ALPHA CYANOPREGNENOLONE; 3 CYANO 7 ETHOXYCOUMARIN; 7 BENZYLOXY 4 TRIFLUOROMETHYLCOUMARIN; 7 BENZYLOXYQUINOLINE; 7 METHOXY 4(AMINOMETHYL)COUMARIN; BETA NAPHTHOFLAVONE; COUMARIN DERIVATIVE; CYTOCHROME; CYTOCHROME P450; CYTOCHROME P450 3A; DEXAMETHASONE; DIBENZYLFLUORESCEIN; ISOPROTEIN; METHOXYRESORUFIN; PENTOXYRESORUFIN; QUINOLINE DERIVATIVE; RIFAMPICIN; UNCLASSIFIED DRUG;

CYTOCHROME; DRUG; FISH; FLUOROMETRY; METABOLISM; ORGANIC COMPOUND; POLLUTION EXPOSURE; SUBSTRATE;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; ASSAY; CATALYSIS; CONTROLLED STUDY; CYPRINODONTIFORMES; DRUG EXPOSURE; ENZYME SUBSTRATE; FEMALE; FLUOROMETRY; IN VITRO STUDY; LIVER MICROSOME; MALE; NONHUMAN; PRIORITY JOURNAL; PROTEIN FAMILY; PROTEIN INDUCTION; PROTEIN METABOLISM; RAINBOW TROUT; SPECIES DIFFERENCE;

ANIMALS; BETA-NAPHTHOFLAVONE; CYTOCHROME P-450 ENZYME SYSTEM; DEXAMETHASONE; ENZYME INDUCTION; FEMALE; FUNDULIDAE; LIVER; MALE; MICROSOMES, LIVER; ONCORHYNCHUS MYKISS; PREGNENOLONE CARBONITRILE; RIFAMPIN; STATISTICS, NONPARAMETRIC;

CYPRINODONTOIDEI; FUNDULUS HETEROCLITUS; MAMMALIA; ONCORHYNCHUS MYKISS; SALMONIDAE; VERTEBRATA;

EID: 77950859276     PISSN: 0166445X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.aquatox.2010.01.005     Document Type: Article

References (86)

1. Addison R.F., Sadler M.C., and Lubet R.A. Absence of hepatic microsomal pentyl- or benzyl-resorufin O-dealkylase induction in rainbow trout (Salmo gairdneri) treated with phenobarbitone. Biochem. Pharmacol. 36 (1987) 1183-1184
2. Andersson T., and Forlin L. Regulation of the cytochrome-P450 enzyme-system in fish. Aquat. Toxicol. 24 (1992) 1-19
3. Ankley G.T., Reinert R.E., Mayer R.T., Burke M.D., and Agosin M. Metabolism of alkoxyphenoxazones by channel catfish liver microsomes: effects of phenobarbital, Aroclor 1254 and 3-methylcholanthrene. Biochem. Pharmacol. 36 (1987) 1379-1381
4. Baririan N., Desager J.P., Petit M., and Horsmans Y. CYP3A4 activity in four different animal species liver microsomes using 7-benzyloxyquinoline and HPLC/spectrofluorometric determination. J. Pharm. Biomed. 40 (2006) 211-214
5. Berndtson A.K., and Chen T.T. Two unique CYP1 genes are expressed in response to 3-methylcholanthrene treatment in rainbow trout. Arch. Biochem. Biophys. 310 (1994) 187-195
6. Bolwell G.P., Bozak K., and Zimmerlin A. Plant cytochrome P450. Phytochemistry 37 (1994) 1491-1506
7. Burke M.D., Brown D., Mayer R.T., and Houlihan D.F.J. Alkoxyquinoline O-dealkylation-a new fluorometric assay for hydrocarbon-induced cytochrome-P450 in fish. Mar. Environ. Res. 39 (1995) 57-60
8. Burke M.D., Thompson S., Elcombe C.R., Halpert J., Haaparanta T., and Mayer R.T. Ethoxy-, pentoxy- and benzyloxyphenoxazones and homologues: a series of substrates to distinguish between different induced cytochromes P-450. Biochem. Pharmacol. 34 (1985) 3337-3345
9. Celander M., Forlin L., and Andersson T. Cytochrome-P-450 Mediated O-Dealkylation of 7-alkoxycoumarins in liver-microsomes from rainbow trout (Salmo Gairdneri). Fish Physiol. Biochem. 6 (1989) 199-205
10. Celander M., Weisbrod R., and Stegeman J.J. Glucocorticoid potentiation of cytochrome P4501A1 induction by 2,3,7,8-tetrachlorodibenzo-p-dioxin in porcine and human endothelial cells in culture. Biochem. Biophys. Res. Commun. 232 (1997) 749-753
11. Crespi C.L., Miller V.P., and Penman B.W. Microtiter plate assays for inhibition of human, drug-metabolizing cytochromes P450. Anal. Biochem. 248 (1997) 188-190
12. Da Silva M.E., Silva J.A., Marangoni S., Novello J.C., and Meirelles N.C. A new method to purify hepatic CYP1A of Prochilodus scrofa, a Brazilian freshwater fish. Comp. Biochem. Physiol. C: Toxicol. Pharmacol. 138 (2004) 67-74
13. Debri K., Boobis A.R., Davies D.S., and Edwards R.J. Distribution and induction of CYP3A1 and CYP3A2 in rat liver and extrahepatic tissues. Biochem. Pharmacol. 50 (1995) 2047-2056
14. Devaux A., Flammarion P., Bernardon V., Garric J., and Monod G. Monitoring of the chemical pollution of the river Rhone through measurement of DNA damage and cytochrome P4501A induction in chub (Leuciscus cephalus). Mar. Environ. Res. 46 (1998) 257-262
15. Foster E.P., Vrolijk N.H., Chen T.T., and Curtis L.R. Interaction of 2,2′,4,4′,5,5′-hexachlorobiphenyl with hepatic cytochrome P-4501A in rainbow trout (Oncorhynchus mykiss). J. Toxicol. Environ. Health 53 (1998) 313-325
16. Ghosal A., Hapangama N., Yuan Y., Lu X., Horne D., Patrick J.E., and Zbaida S. Rapid determination of enzyme activities of recombinant human cytochromes P450, human liver microsomes and hepatocytes. Biopharm. Drug Dispos. 24 (2003) 375-384
17. Gooneratne R., Miranda C.L., Henderson M.C., and Buhler D.R. Beta-naphthoflavone induced CYP1A1 and 1A3 proteins in the liver of rainbow trout (Oncorhynchus mykiss). Xenobiotica 27 (1997) 175-187
18. Graham R.A., Downey A., Mudra D., Krueger L., Carroll K., Chengelis C., Madan A., and Parkinson A. In vivo and in vitro induction of cytochrome P450 enzymes in beagle dogs. Drug Metab. Dispos. 30 (2002) 1206-1213
19. Gray E.S., Woodin B.R., and Stegeman J.J. Sex-differences in hepatic monooxygenases in winter flounder (Pseudopleuronectes americanus) and scup (Stenotomus chrysops) and regulation of P450 forms by estradiol. J. Exp. Zool. 259 (1991) 330-342
20. Haasch M.L., Graf W.K., Quardokus E.M., Mayer R.T., and Lech J.J. Use of 7-alkoxyphenoxazones, 7-alkoxycoumarins and 7-alkoxyquinolines as fluorescent substrates for rainbow trout hepatic microsomes after treatment with various inducers. Biochem. Pharmacol. 47 (1994) 893-903
21. Hahn M.E., Lamb T.M., Schultz M.E., Smolowitz R.M., and Stegeman J.J. Cytochrome-P4501A induction and inhibition by 3,3′,4,4′-tetrachlorobiphenyl in an Ah receptor-containing fish hepatoma-cell line (PLHC-1). Aquat. Toxicol. 26 (1993) 185-208
22. Hahn M.E., Woodin B.R., Stegeman J.J., and Tillitt D.E. Aryl hydrocarbon receptor function in early vertebrates: inducibility of cytochrome P450 1A in agnathan and elasmobranch fish. Comp. Biochem. Physiol. 120 (1998) 67-75
23. Handschin C., and Meyer U.A. Induction of drug metabolism: the role of nuclear receptors. Pharmacol. Rev. 55 (2003) 649-673
24. Hartl M.G., Kilemade M., Sheehan D., Mothersill C., O'Halloran J., O'Brien N.M., and van Pelt F.N. Hepatic biomarkers of sediment-associated pollution in juvenile turbot, Scophthalmus maximus L. Mar. Environ. Res. 64 (2007) 191-208
25. Hegelund T., and Celander M.C. Hepatic versus extrahepatic expression of CYP3A30 and CYP3A56 in adult killifish (Fundulus heteroclitus). Aquat. Toxicol. 64 (2003) 277-291
26. Hegelund T., Ottosson K., Radinger M., Tomberg P., and Celander M.C. Effects of the antifungal imidazole ketoconazole on CYP1A and CYP3A in rainbow trout and killifish. Environ. Toxicol. Chem. 23 (2004) 1326-1334
27. Hemeryck A., and Belpaire F.M. Selective serotonin reuptake inhibitors and cytochrome P-450 mediated drug-drug interactions: an update. Curr. Drug Metab. 3 (2002) 13-37
28. Honkakoski P., and Negishi M. Regulation of cytochrome P450 (CYP) genes by nuclear receptors. Biochem. J. 347 (2000) 321-337
29. Iwata H., Yoshinari K., Negishi M., and Stegeman J.J. Species-specific responses of constitutively active receptor (CAR)-CYP2B coupling: lack of CYP2B inducer-responsive nuclear translocation of CAR in marine teleost, scup (Stenotomus chrysops). Comp. Biochem. Phys. C 131 (2002) 501-510
30. James M.O., and Boyle S.M. Cytochromes P450 in crustacea. Comp. Biochem. Phys. 121 (1998) 157-172
31. Jenner A.M., and Timbrell J.A. Influence of inducers and inhibitors of cytochrome P450 on the hepatotoxicity of hydrazine in vivo. Arch. Toxicol. 68 (1994) 349-357
32. Kashiwada S., Hinton D.E., and Kullman S.W. Functional characterization of medaka CYP3A38 and CYP3A40: kinetics and catalysis by expression in a recombinant baculovirus system. Comp. Biochem. Physiol. C: Toxicol. Pharmacol. 141 (2005) 338-348
33. Khetani S.R., and Bhatia S.N. Microscale culture of human liver cells for drug development. Nat. Biotechnol. 26 (2008) 120-126
34. Kleinow K.M., Haasch M.L., Williams D.E., and Lech J.J. A comparison of hepatic P450 induction in rat and trout (Oncorhynchus mykiss): delineation of the site of resistance of fish to phenobarbital-type inducers. Comp. Biochem. Phys. 96 (1990) 259-270
35. Kloepper-Sams P.J., and Stegeman J.J. The temporal relationships between P450E protein content, catalytic activity, and mRNA levels in the teleost Fundulus heteroclitus following treatment with beta-naphthoflavone. Arch. Biochem. Biophys. 268 (1989) 525-535
36. Kullman S.W., Kashiwada S., and Hinton D.E. Analysis of medaka cytochrome P450 3A homotropic and heterotropic cooperativity. Mar. Environ. Res. 58 (2004) 469-473
37. Lee M.D., Ayanoglu E., and Gong L. Drug-induced changes in P450 enzyme expression at the gene expression level: a new dimension to the analysis of drug-drug interactions. Xenobiotica 36 (2006) 1013-1080
38. Lee P.C., Yoon H.I., Haasch M.L., and Lech J.J. Negative control of cytochrome P450 1A1 (CYP1A1) by glucocorticoids in rainbow trout liver. Comp. Biochem. Phys. 104 (1993) 457-461
39. Lemaire R.F., Forlin L., and DLivingstone D.R. Responses of hepatic biotransformation and antioxidant enzymes to CYP1A inducers (3-methylcholanthrenem, β-naphthoflavone) in sea bass (Dicentrarchus labrax), dab (Limanda limanda) and rainbow trout (Oncorhynchus mykiss). Aquat. Toxicol. 36 (1996) 141-160
40. Lewis D.F., Jacobs M.N., Dickins M., and Lake B.G. Quantitative structure--activity relationships for inducers of cytochromes P450 and nuclear receptor ligands involved in P450 regulation within the CYP1, CYP2, CYP3 and CYP4 families. Toxicology 176 (2002) 51-57
41. Lewis D.F.V., and Wiseman A. A selective review of bacterial forms of cytochrome P450 enzymes-review. Enzyme Microb. Technol. 36 (2005) 377-384
42. Li D., Yang X.L., Zhang S.J., Lin M., Yu W.J., and Hu K. Effects of mammalian CYP3A inducers on CYP3A-related enzyme activities in grass carp (Ctenopharyngodon idellus): possible implications for the establishment of a fish CYP3A induction model. Comp. Biochem. Physiol. C: Toxicol. Pharmacol. 147 (2008) 17-29
43. Lu C., and Li A.P. Species comparison in P450 induction: effects of dexamethasone, omeprazole, and rifampin on P450 isoforms 1A and 3A in primary cultured hepatocytes from man, Sprague-Dawley rat, minipig, and beagle dog. Chem. Biol. Interact. 134 (2001) 271-281
44. Luo G., Cunningham M., Kim S., Burn T., Lin J., Sinz M., Hamilton G., Rizzo C., Jolley S., Gilbert D., Downey A., Mudra D., Graham R., Carroll K., Xie J., Madan A., Parkinson A., Christ D., Selling B., LeCluyse E., and Gan L.S. CYP3A4 induction by drugs: correlation between a pregnane X receptor reporter gene assay and CYP3A4 expression in human hepatocytes. Drug Metab. Dispos. 30 (2002) 795-804
45. Lupp A., Glockner R., Etzrodt J., and Muller D. Precision-cut slices from basal cytochrome P450-dependent activities and inducibility. Anal. Bioanal. Chem. 392 (2008) 1173-1184
46. Maglich J.M., Caravella J.A., Lambert M.H., Willson T.M., Moore J.T., and Ramamurthy L. The first completed genome sequence from a teleost fish (Fugu rubripes) adds significant diversity to the nuclear receptor superfamily. Nucleic Acids Res. 31 (2003) 4051-4058
47. Miller K.A., Addison R.F., and Bandiera S.M. Hepatic CYP1A levels and EROD activity in English sole: biomonitoring of marine contaminants in Vancouver Harbour. Mar. Environ. Res. 57 (2004) 37-54
48. Miller V.P., Stresser D.M., Blanchard A.P., Turner S., and Crespi C.L. Fluorometric high-throughput screening for inhibitors of cytochrome P450. Ann. N. Y. Acad. Sci. 919 (2000) 26-32
49. Mingoia R.T., Nabb D.L., Yang C.H., and Han X. Primary culture of rat hepatocytes in 96-well plates: effects of extracellular matrix configuration on cytochrome P450 enzyme activity and inducibility, and its application in in vitro cytotoxicity screening. Toxicol. In Vitro 21 (2007) 165-173
50. Miranda C.L., Wang J.L., Henderson M.C., Zhao X., Guengerich F.P., and Buhler D.R. Comparison of rainbow trout and mammalian cytochrome P450 enzymes: evidence for structural similarity between trout P450 LMC5 and human P450IIIA4. Biochem. Biophys. Res. Commun. 176 (1991) 558-563
51. Monshouwer M., van't Klooster G.A.E., Nijmeijer S.M., Witkamp R.F., and van Miert A.S.J.P.A.M. Characterization of cytochrome P450 isoenzymes in primary cultures of pig hepatocytes. Toxicol. In Vitro 12 (1998) 715-723
52. Moore J.T., Moore L.B., Maglich J.M., and Kliewer S.A. Functional and structural comparison of PXR and CAR. Biochim. Biophys. Acta, Gen. Subj. 1619 (2003) 235-238
53. Moore L.B., Maglich J.M., McKee D.D., Wisely B., Willson T.M., Kliewer S.A., Lambert M.H., and Moore J.T. Pregnane X receptor (PXR), constitutive androstane receptor (CAR), and benzoate X receptor (BXR) define three pharmacologically distinct classes of nuclear receptors. Mol. Endocrinol. 16 (2002) 977-986
54. Morrison H.G., Weil E.J., Karchner S.I., Sogin M.L., and Stegeman J.J. Molecular cloning of CYP1A from the estuarine fish Fundulus heteroclitus and phylogenetic analysis of CYP1 genes: update with new sequences. Comp. Biochem. Phys. 121 (1998) 231-240
55. Nelson D.R. Comparison of P450s from human and fugu: 420 million years of vertebrate P450 evolution. Arch. Biochem. Biophys. 409 (2003) 18-24
56. Novi S., Pretti C., Cognetti A.M., Longo V., Marchetti S., and Gervasi P.G. Biotransformation enzymes and their induction by beta-naphthoflavone in adult sea bass (Dicentrarchus labrax). Aquat. Toxicol. 41 (1998) 63-81
57. Onderwater R.C., Venhorst J., Commandeur J.N., and Vermeulen N.P. Design, synthesis, and characterization of 7-methoxy-4-(aminomethyl)coumarin as a novel and selective cytochrome P450 2D6 substrate suitable for high-throughput screening. Chem. Res. Toxicol. 12 (1999) 555-559
58. Otyepka M., Skopalik J., Anzenbacherova E., and Anzenbacher P. What common structural features and variations of mammalian P450s are known to date?. Biochim. Biophys. Acta 1770 (2007) 376-389
59. Padros J., Pelletier E., Reader S., and Denizeau F. Mutual in vivo interactions between benzo[a]pyrene and tributyltin in brook trout (Salvelinus fontinalis). Environ. Toxicol. Chem. 19 (2000) 1019-1027
60. Parente T.E., De-Oliveira A.C., Beghini D.G., Chapeaurouge D.A., Perales J., and Paumgartten F.J. Lack of constitutive and inducible ethoxyresorufin-O-deethylase activity in the liver of suckermouth armored catfish (Hypostomus affinis and Hypostomus auroguttatus, Loricariidae). Comp. Biochem. Physiol. C: Toxicol. Pharmacol. 150 (2009) 252-260
61. Parente T.E., De-Oliveira A.C., Silva I.B., Araujo F.G., and Paumgartten F.J. Induced alkoxyresorufin-O-dealkylases in tilapias (Oreochromis niloticus) from Guandu river, Rio de Janeiro, Brazil. Chemosphere 54 (2004) 1613-1618
62. Pathiratne A., and George S. Comparison of xenobiotic metabolizing enzymes of tilapia with those of other fish species and interspecies relationships between gene families. Mar. Environ. Res. 42 (1996) 293-296
63. Perkins E.J., and Schlenk D. Immunochemical characterization of hepatic cytochrome P450 isozymes in the channel catfish: assessment of sexual, developmental and treatment-related effects. Comp. Biochem. Phys. 121 (1998) 305-310
64. Price R.J., Surry D., Renwick A.B., Meneses-Lorente G., Lake B.G., and Evans D.C. CYP isoform induction screening in 96-well plates: use of 7-benzyloxy-4-trifluoromethylcoumarin as a substrate for studies with rat hepatocytes. Xenobiotica 30 (2000) 781-795
65. Renwick A.B., Lavignette G., Worboys P.D., Williams B., Surry D., Lewis D.F.V., Price R.J., Lake B.G., and Evans D.C. Evaluation of 7-benzyloxy-4-trifluoromethylcoumarin, some other 7-hydroxy-4-trifluorometnylcoumarin derivatives and 7-benzyloxyquinoline as fluorescent substrates for rat hepatic cytochrome P450 enzymes. Xenobiotica 31 (2001) 861-878
66. Renwick A.B., Lewis D.F.V., Fulford S., Surry D., Williams B., Worboys P.D., Cai X., Wang R.W., Price R.J., Lake B.G., and Evans D.C. Metabolism of 2,5-bis(trifluoromethyl)-7-benzyloxy-4-trifluoromethylcoumarin by human hepatic CYP isoforms: evidence for selectivity towards CYP3A4. Xenobiotica 31 (2001) 187-204
67. Sadar M.D., Ash R., Sundqvist J., Olsson P.E., and Andersson T.B. Phenobarbital induction of CYP1A1 gene expression in a primary culture of rainbow trout hepatocytes. J. Biol. Chem. 271 (1996) 17635-17643
68. Scornaienchi, M.L., 2009. Functional characterization of zebrafish cytochrome P450 1 and 3A genes using heterologously expressed proteins. MSc Thesis. Dept of Biology. McMaster University.
69. Seliskar M., and Rozman D. Mammalian cytochromes P450--importance of tissue specificity. Biochim. Biophys. Acta 1770 (2007) 458-466
70. Smeets J.M., Wamsteker J., Roth B., Everaarts J., and van den Berg M. Cytochrome P4501A induction and testosterone hydroxylation in cultured hepatocytes of four fish species. Chemosphere 46 (2002) 163-172
71. Snyder M.J. Cytochrome P450 enzymes in aquatic invertebrates: recent advances and future directions. Aquat. Toxicol. 48 (2000) 529-547
72. Stagg R.M., Mcintosh A., and Mackie P. Elevation of hepatic monooxygenase activity in the dab (Limanda-Limanda L) in relation to environmental contamination with petroleum-hydrocarbons in the northern North-Sea. Aquat. Toxicol. 33 (1995) 245-264
73. Stegeman J.J., Hahn M.E., Weisbrod R., Woodin B.R., Joy J.S., Najibi S., and Cohen R.A. Induction of cytochrome P4501A1 by aryl hydrocarbon receptor agonists in porcine aorta endothelial cells in culture and cytochrome P4501A1 activity in intact cells. Mol. Pharmacol. 47 (1995) 296-306
74. Stegeman J.J., Woodin B.R., Singh H., Oleksiak M.F., and Celander M. Cytochromes P450 (CYP) in tropical fishes: catalytic activities, expression of multiple CYP proteins and high levels of microsomal P450 in liver of fishes from Bermuda. Comp. Biochem. Physiol. 116 (1997) 61-75
75. Stresser D.M., Blanchard A.P., Turner S.D., Erve J.C., Dandeneau A.A., Miller V.P., and Crespi C.L. Substrate-dependent modulation of CYP3A4 catalytic activity: analysis of 27 test compounds with four fluorometric substrates. Drug Metab. Dispos. 28 (2000) 1440-1448
76. Stresser D.M., Turner S.D., Blanchard A.P., Miller V.P., and Crespi C.L. Cytochrome P450 fluorometric substrates: identification of isoform-selective probes for rat CYP2D2 and human CYP3A4. Drug Metab. Dispos. 30 (2002) 845-852
77. Thibaut R., Schnell S., and Porte C. The interference of pharmaceuticals with endogenous and xenobiotic metabolizing enzymes in carp liver: an in vitro study. Environ. Sci. Technol. 40 (2006) 5154-5160
78. Thomas J.H. Rapid birth-death evolution specific to xenobiotic cytochrome P450 genes in vertebrates. PLoS Genet. 3 (2007) e67
79. Tseng H.P., Hseu T.H., Buhler D.R., Wang W.D., and Hu C.H. Constitutive and xenobiotics-induced expression of a novel CYP3A gene from zebrafish larva. Toxicol. Appl. Pharmacol. 205 (2005) 247-258
80. Urlacher V., and Schmid R.D. Biotransformations using prokaryotic P450 monooxygenases. Curr. Opin. Biotechnol. 13 (2002) 557-564
81. Vaccaro E., Salvetti A., Carratore R.D., Nencioni S., Longo V., and Gervasi P.G. Cloning, tissue expression, and inducibility of CYP 3A79 from sea bass (Dicentrarchus labrax). J. Biochem. Mol. Toxicol. 21 (2007) 32-40
82. Walker C.H. Avian forms of cytochrome P450. Comp. Biochem. Physiol. 121 (1998) 65-72
83. Waxman D.J., and Azaroff L. Phenobarbital induction of cytochrome P-450 gene expression. Biochem. J. 281 (1992) 577-592
84. Weaver R.J., Thompson S., Smith G., Dickins M., Elcombe C.R., Mayer R.T., and Burke M.D. A comparative study of constitutie and induced alkoxyresorufin o-dealkylation and individual cytochrome P450 forms in Cynomolgus monkey (Macaca fascicularis), human, mouse, rat and hapster liver microsomes. Biochem. Pharmacol. 47 (1994) 763-773
85. Westerink W.M.A., Stevenson J.C.R., and Schoonen W.G.E.J. Pharmacologic profiling of human and rat cytochrome P450 1A1 and 1A2 induction and competition. Arch. Toxicol. 82 (2008) 909-921
86. White R.D., Shea D., Solow A.R., and Stegeman J.J. Induction and post-transcriptional suppression of hepatic cytochrome P450 1A1 by 3,3′,4,4′-tetrachlorobiphenyl. Biochem. Pharmacol. 53 (1997) 1029-1040