The expression and regulation of drug metabolism in human placenta

Advanced Drug Delivery Reviews

Volumn 38, Issue 1, 1999, Pages 81-97

  Pasanen, Markku ^a,b  

^a UNIVERSITY OF OULU   (Finland)

^b NATIONAL AGENCY FOR MEDICINES   (Finland)

Author keywords

Conjugation reactions; Cytochrome P450; Extrahepatic metabolism; Manooxygenases; Steroid metabolism

Indexed keywords

ANTIBODIES; AROMATIC COMPOUNDS; BIOCONVERSION; CATALYSIS; CATALYST ACTIVITY; CHOLESTEROL; DNA; ENZYMES; GENES; METABOLISM; OXIDATION; RNA;

ACETYL TRANSFERASE; AROMATASE; BENZOPYRENE; EPOXIDE HYDROLASE; GLUTATHIONE TRANSFERASE; XENOBIOTICS;

DRUG INTERACTIONS;

ACYLTRANSFERASE; AFLATOXIN B1; AMPHETAMINE; ARYLAMINE ACETYLTRANSFERASE; CARCINOGEN; CIMETIDINE; CODEINE; CYTOCHROME P450; CYTOCHROME P450 ISOENZYME; DEXTROMETHORPHAN; EPOXIDE HYDROLASE; ERYTHROMYCIN; GLUCOCORTICOID; GLUTATHIONE TRANSFERASE; GLYCOPROTEIN P; HEXOBARBITAL; ISONIAZID; NICOTINE; NITRIC OXIDE SYNTHASE; PEROXIDASE; PETHIDINE; PHENCYCLIDINE; PHENOBARBITAL; PHENYTOIN; POLYCYCLIC AROMATIC HYDROCARBON; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE (PHOSPHATE) DEHYDROGENASE (QUINONE); SULFOTRANSFERASE; THALIDOMIDE; UNINDEXED DRUG; WARFARIN;

CIGARETTE SMOKING; DRUG CONJUGATION; DRUG METABOLISM; ENZYME ACTIVATION; ENZYME LOCALIZATION; ENZYME REGULATION; HUMAN; NONHUMAN; PLACENTA; PRIORITY JOURNAL; PROTEIN EXPRESSION; REVERSE TRANSCRIPTION POLYMERASE CHAIN REACTION; REVIEW; XENOBIOTIC METABOLISM;

EID: 0032934670     PISSN: 0169409X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0169-409X(99)00008-3     Document Type: Article

References (138)

1. G.W. Mihaly, D.J. Morgan, Placental drug transfer: effects of gestational age and species, Pharmacol. Ther. 23 (1984) 253-266.
2. O. Pelkonen, Fetoplacental biochemistry - xenobiotic metabolism and pharmacokinetics, in: K. Hemminki, M. Sorsa, H. Vainlo (Eds.), Occupational Hazards and Reproduction, Hemisphere, Washington, 1985.
3. V. Kidakoy, T. Sokur, A. Volobuev, I. Tzibulskaya, V. Malisheva, B. Zikin, L. Ezova, L. Balyaeva, P. Bonartzev, N. Speranskaya, I. Tchesnokova, N. Matveeva, E. Kalizauk, L. Miturova, N. Orlova, Female reproductive function in areas affected by radiation after Chernobyl power station accident, Environ. Health Perspect. 101 (Suppl. 2) (1993) 117-123.
4. J. Hakkola, O. Pelkonen, M. Fasanen, H. Raunio, Xenobiotic-metabolizing cytochrome P450 enzymes in the human feto-placental unit: role in intrauterine toxicity, Crit. Rev. Toxicol. 28 (1998) 35-72.
5. R. Welch, Y. Harrison, A. Conney, P. Poppers, M. Fluster, Cigarette smoking: stimulatory effect on metabolism of benzo(a)pyrene by enzymes in human placenta, Science 160 (1968) 541-542.
6. K. Vähäkängas, N. Bjelogrlick, P. Sivonen, H. Raunio, N. Käkrki, O. Pelkonen, The formation of benzo(a)pyrene diolepoxide DNA-adducts in human tissues, in: I. Schuster (Ed.), Cytochrome P-450: Biochemistry and Biophysics, Taylor & Francis, London, 1989, pp. 775-778.
7. M.J. Namkung, M.R. Juchau, On the capacity of human placental enzymes to catalyze the formation of diols from benzo(a)pyrene, Toxicol. Appl. Pharmacol. 55 (1980) 253-259.
8. C. Hansen, I. Asmussen, H. Autrup, Detection of carcinogen-DNA adducts in human fetal tissues by the 32P-post-labeling procedure, Environ. Health Perspect. 99 (1993) 229-231.
9. M. Pasanen, O. Pelkonen, Xenobiotic and steroid-metabolizing monooxygenases catalyzed by cytochrome P450 and glutathione S-transferase conjugations in the human placenta and theft relationships to maternal cigarette smoking, Placenta 11 (1990) 75-85.
10. M. Pasanen, S. Stacey, A. Lykkesfeldt, P. Briand, K. Hines, H. Autxup, Induction of cytochrome P4501A1 gene expression in human breast tumor cell lines, Chem.-Biol. Interact. 66 (1988) 223-232.
11. M. Pasanen, K. Vähäkängas, L.A. Sotaniemi, O. Pelkonen, The effect of cigarette smoking on drug metabolism in the liver and placenta: the use of cotinine in verifying smoking status, Eur. J. Drug Metab. Pharmacokin. 13 (1) (1988) 41-45.
12. M. Pasanen, T. Taskinen, L.A. Sotaniemi, M. Kairaluoma, O. Pelkonen, Inhibitor panel studies of human hepatic and placental cytochrome P-450-associated monooxygenase activities, Pharmacol. Toxicol. 62 (1988) 311-317.
13. T.K. Wong, R.B. Everson, S.-T. Hsu, Potent induction of human placental monooxygenase activity by previous dietary exposure to polychlorinated biphenyls and theft thermal degradation products, Lancet 1 (1985) 721-724.
14. J. Hakkola, H. Raunio, R. Purkunen, O. Pelkonen, S. Saarlkoski, T. Cresteil, M. Pasanen, Detection of cytochrome P450 gene expression in human placenta at first trimester of pregnancy, Biochem. Pharmacol. 52 (1996) 379-383.
15. J. Hakkola, M. Pasanen, I. Hukkanen, O. Pelkonen, I. Mienpit, R.I. Edwards, A.R. Boobis, M. Raunio, Expression of xenobiotic-metabolizing cytochrome P450 forms in human full-term placenta, Biochem. Pharmacol. 51 (1996) 403-411.
16. M. Pasanen, R.-L. Helin-Martikainen, O. Pelkonen, P. Kirkinen, Intrahepatic cholestasis of pregnancy impairs the activities of human placental xenobiotic and steroid metabolizing enzymes in vitro, Placenta 18 (1997) 37-41.
17. F. Farm, T. Pohixuan, C. Omiecinski, Expression of cytochrome P450s and microsomal epoxide hydrolase in primary cultures of human umbilical vein endothelial cells, Toxicol. Appl. Pharmacol. 124 (1994) 1-9.
18. D.R. Nelson, T. Kamataki, D.J. Waxman, F.P. Guengerich, K. Feyereisen, F.J. Gonzalez, M.J. Coon, I.C. Gunsalus, O. Gotoli, K. Okuda, D.W. Nebert, The P450 superfamily update on new sequences, gene mapping, accession numbers, early trivial names of enzymes, and nomenclature, DNA Cell Biol. 12 (1) (1993) 1-51.
19. Q. Nelson, L. Koynians, T. Kamataki, I. Stegeman, K. Feyereisen, D. Waxman, M. Waterman, O. Gotob, M. Coon, R. Estabrook, I. Gunsalus, D. Nebert, P450 superfamily: update on new sequences, gene mapping, accession numbers and nomenclature, Pharmacogenetics 6 (1996) 1-42.
20. Nelson, O. (1998) Human P450s. Internet homepage, www.drnelson.utmem.edu.
21. M. Pasanen, O. Pelkonen, Human placental xenobiotic and steroid biotransformations catalyzed by cytochrome P450, epoxide hydrolase, and glutathione S transferase activities and their relationships to maternal cigarette smoking, Drug. Metab. Rev. 21 (3) (1990) 427-461.
22. M. Pasanen, O. Pelkonen, The expression and environmental regulation of P450 enzymes in human placenta, Crit. Rev. Toxicol. 24 (1994) 211-229.
23. M. Pasanen, T. Haaparanta, M. Sundin, P. Sivonen, K. Vähäkängas, H. Raunio, K. Hines, J.-A. Gustafason, O. Pelkonen, Immunochemical and molecular biochemical studies on human placental cigarette smoke-inducible cytochrome P-450-dependent monooxygenase activities, Toxicology 62 (1990) 175-187.
24. J. Hakkola, M. Pasanen, O. Pelkonen, J. Hukkanen, S. Evisalmi, S. Anttila, A. Kane, M. Mäntylä, K. Purkunen, S. Saarikoski, M. Tooming, K. Raunio, Expression of CYP1B1 in human adult and fetal tissues and differential inducibility of CYP1B1 and CYP1A1 by Ah-receptor ligands in human placenta and cultured cells, Carcinogenesis 18 (1997) 391-397.
25. O. Peikonen, K. Vähäkängas, N.T. Kärki, E.A. Sotaniemi, Genetic and environmental regulation of aryl hydrocarbon hydroxylase in man: studies with liver, lung, placenta and lymphocytes, Toxicol. Pathol. 12 (1984) 256-260.
26. A.C. Kaelin, A.J. Cummings, Differential inhibition of human placental in monooxygenase activity: Evidence for multiple forms of 7-ethoxycoumarin O-deethylase, Biochem. Pharmacol. 33 (1984) 505-508.
27. M.R. Juchau, Human placental hydroxylation of 3,4-benzo(a)pyrene during early gestation and at term, Toxicol. Appl. Pharmacol. 18 (1971) 665-675.
28. O. Pelkonen, P. Arvela, N.T. Kärki, 3,4-Benzpyrene and N-methylalanine metabolizing enzymes in the immature human foetus and placenta, Acta Pharmacol. Toxicol. 30 (1971) 385-395.
29. H.L. Gurtoo, C.I. Williams, K. Gottlieb, A.L. Mulhern, L. Cabalies, T.B. Vaught, A.J. Mauinelllo, Population distribution of placental benzo(a)pyrene metabolism in smokers, Int. J. Cancer 31 (1983) 29-37.
30. O. Pelkonen, P. Jouppila, N.T. Kärki, Effect of maternal cigarette smoking in 3,4-benzpyrene and N-methylaniline metabolism in human fetal liver and placenta, Toxicol. Appl. Pharmacol. 23 (1972) 399-407.
31. O. Pelkonen, P. Jouppila, N.T. Kärki, Attempts to induce drug metabolism in human fetal liver and placenta by the administration of phenobarbital to mothers, Arch. Inv. Pharmacodyn. Ther. 202 (1973) 288-297.
32. O. Pelkonen, M. Pasanen, H.B.G. Kuha, M. Kairaluoma, E.A. Sotaniemi, S.S. Park, F.R. Friedman, H.V. Gelboin, The effect of cigarette smoking on 7-ethoxyresorufin O-deethylase and other monooxygenase activities in human liver: analyses with monoclonal antibodies, Br. J. Clin. Pharmacol. 22 (1986) 125-134.
33. W.A. Boadi, I. Urbach, E.K. Barnea, J.M. Brandes, S. Yannai, Enzyme activities in the term human placenta: in vitro effect of cadmium, Pharmacol. Toxicol. 71 (1992) 209-212.
34. M.R. Juchau, P.K. Zachariah, Comparative studies on the oxidation and reduction of drug substrates in human versus rat hepatic microsomes, Biochem. Pharmacol. 24 (1975) 227-233.
35. O. Pelkonen, N.T. Kärki, P. Korhonen, M. Koivisto, K. Tuimala, A. Kauppila, Human placental aryl hydrocarbon hydroxylase: genetics and environmental influences, in: RW. Jones, P. Leber (Eds.), Polynuclear Aromatic Hydrocarbons, Ann Arbor Science Publishers Trio, Ann Arbor, 1979, pp. 765-777.
36. M. Pasanen, H. Raunio, O. Pelkonen, Freezing affects the activity and subcellular distribution profile of placental xenobiotic- and steroid-metabolizing enzymes, Placenta 6 (1985) 527-535.
37. M. Jacobson, W. Latin, P. Poppers, A.W. Wood, A.H. Conney, Comparison of the O-dealkylation of 7-ethoxycoumarin and the hydroxylation of benzo(a)pyrene in human placenta, Clin. Pharmacol. Ther. 16 (1974) 701-710.
38. A.C. Kaelin, A.J. Cummings, A survey of aryl hydrocarbon hydroxylase activity in human placental homogenates, Placenta 4 (1983) 471-478.
39. M. Pasanen, T. Taskinen, M. Iscan, E.A. Sotaniemi, M.A. Kairaluoma, O. Pelkonen, Inhibition of human hepatic and placental xenobiotic monooxygenases by imidazole antimycotics, Biochem. Pharmacol. 37 (20) (1988) 3861-3866.
40. T. Fujino, S.S. Park, D. West, H.V. Gelboin, Phenotyping of cytochromes P-450 in human tissues with monoclonal antibodies, Proc. Natl. Acad. Sci. USA 79 (1982) 3682-3686.
41. M. Pasanen, K. Stenbäck, S.S. Park, H.V. Gelboin, O. Pelkonen, Immunohistochemical detection of human placental cytochrome P-450-associated monooxygenase system induced by maternal cigarette smoking, Placenta 9 (1988) 267-275.
42. S. Shum, N.M. Jensen, D.W. Nebert, The murine Ah locus: in utero toxicity and teratogenesis associated with genetic difference in benzo(a)pyrene metabolism, Teratology 20 (1979) 365-376.
43. D.K. Manchester, S.K. Gordon, C.L. Golas, L.A. Roberts, A.B. Okey, Ah receptor in human placenta: Stabilization by molybdate and characterization of binding of 2,3,7,8-tetrachlorodibenzo-p-dioxin, 3-inethylcholanthrene, and benzo(a)pyrene, Cancer Res. 47 (1987) 4861-4868.
44. Q. Bui, J. Weisz, Identification of microsomal, organic hydroperoxide-dependent catechol estrogen formation: comparison with the NADPH-dependent mechanism, Pharmacology 36 (1988) 356-364.
45. K. Kozak, B. Abbot, O. Hankinson, ARNT-deficient mice and placental differentiation, Develop. Biol. 191 (1997) 297-305.
46. D. Sesardic, M. Pasanen, O. Pelkonen, A.K. Boobis, Differential expression and regulation of numbers of the cytochrome P4501A gene subfamily in human tissues, Carcinogenesis 11 (7) (1990) 1183-1188.
47. D.L. Berry, P.K. Zachariah, T.J. Slaga, M.R. Juchau, Analysis of the biotransformation of benzo(a)pyrene in human fetal and placental tissues with high-pressure liquid chromatography, Eur. J. Cancer 13 (1977) 667-675.
48. O. Pelkonen, M.-L. Moilanen, The specificity and multiplicity of human placental xenobiotic-metabolizing monooxygenase system studied by potential substrates, inhibitors and gel electrophoresis, Med. Biol. 57 (1979) 306-312.
49. M. Pasanen, O. Pelkonen, Inhibition of xenobiotic and steroid metabolism by aminoglutethimide in human placentas from smoking and non-smoking mothers, in: J. Rydström, J. Montelius, M. Bengtsson (Eds.), Extrahepatic Drug Metabolism and Chemical Carcinogenesis, Elsevier Science Publications, Amsterdam, 1983, pp. 217-218.
50. A.F. Rettie, L. Heimark, R.T. Mayer, M.D. Burke, W.F. Trager, M.R. Jucabu, Stereoselective and regioselective hydroxylation of warfarin and selective O-dealkylation of phenoxazone ethers in human placenta, Biochem. Biophys. Res. Commun. 126 (1985) 1013-1021.
51. N. Collazo, L. Sukatos, Metabolism of 4-(methylnitrosoamino)-1-(3-pyridyl)-1-butanone (NNK) in human placental microsomes, Biochem. Pharmacol. 50 (1995) 1933-1941.
52. H.A. Omar, R. Figueroa, R.A. Omar, M.S. Wolin, Properties of an endogenous arachidonic acid-elicited relaxing mechanism in human placental vessels, Am. J. Obstet. Gynecol. 167 (1992) 1064-1070.
53. W. Schaefer, K. Werner, H. Schweer, J. Schneider, E. Arbogast, H. Zahradnik, Cytochrome P450 metabolites of arachodonic acid in human placenta, Prostaglandins 54 (1997) 677-687.
54. L.A. Meigs, The constitutive 7-ethoxycoumarin O-deethylase activity of human placental microsomes: relationship to aromatase, Biochem. Biophys. Res. Commun. 134 (1987) 1012-1018.
55. Y. Osawa, T. Higashiyama, C. Yarborough, 1992. Diverse evictions of aromatase CYT P450: catecholestrogen synthesis, cocaine N-demethylation, and other selective drug metabolism. Abstracts of Papers at the 8th Int. Conf on Cytochrome P450, p. 251.
56. M. Sawada, K. Kitamura, T. Norose, M. Kitada, K. Itahasbi, T. Kamataki, Metabolic activation of aflatoxin B1 by human placental microsomes, J. Toxicol. Sci. 18 (1993) 129-132.
57. Y. Toma, T. Higashiyama, C. Yarborough, Y Osawa, Diverse functions of aromatase: O-deethylation of 7-ethoxycoumarin, Endocrinology 137 (1996) 3791-3796.
58. A. Traeger, H. Hoffman, H. Frankie, M. Guntner, Untersuchungen uber den einfluss von phenobarbital auf arzneitmittelabbauende enzyme in der mensoblichen plazenta, auf die feinstuktor der chorionzotten und den verlaufder serum bilirubinkonzentration neugandborener, Z. Geburtsh. Perinat. 176 (1972) 397-402.
59. MX. Juchau, A.E. Rettie, in: S. Fabrio, A.R. Scialli (Eds.), Drug and Chemical Action in Pregnancy: Pharmacologic and Toxicologic Principles, Dekker, New York, 1986.
60. S.M. Jones, A.R. Boobis, G.E. Moore, P.M. Stanier, Expression of CYP2EI during human fetal development: methylation of the CYP2E1 gene in human fetal and adult liver samples, Biochem. Pharmacol. 43 (1992) 1876-1879.
61. P. Pienimäki, E. Lampela, J. Hakkola, P. Arvela, H. Raunio, K. Vähäkangas, Pharmacokinetics of oxcabazepine and carbamazepine in human placenta, Epilepsia 38 (1997) 309-316.
62. B.J. Song, T. Matsmaga, J.P. Hardwick, S.S. Park, R.L. Veech, C.S. Yang, H.V. Gelboin, F.J. Gonzalez, Stabilization of cytochrome P450j messenger ribonucleic acid in the diabetic rat, Mol. Endocrinol. 1 (1987) 542-547.
63. B. Song L, R.L. Veech, P. Saenger, Cytochrome P450IIE1 is elevated in lymphocytes from poorly controlled insulin-dependent diabetics, J. Clin. Endocrinol. Metab. 71 (1990) 1036-1040.
64. P. Karl, B. Gordon, C. Lieber, S. Fisher, Acetaldehyde production and transfer in the perfused human placental cotyledon, Science 242 (1988) 273-275.
65. A. Rasheed, R. Hines, D. McCarver-May, Variation in induction of human placental CYP2E1: Possible role is susceptibility to fetal alcohol syndrome, Toxicol. Appl. Pharmacol. 144 (1997) 396-400.
66. D. Mcrobie, D. Glover, T. Tracy, Effects of gestational and overt diabetes on human placental cytochromes P450 and glutathione S-transferase, Drug Metab. Dispos. 26 (1998) 361-371.
67. D.W. Nebert, D.R. Nelson, M.R. Coon, R.W. Estabrook, K. Feyereisen, Y. Fujii-Kuriyama, F.J. Gonzalez, F.P. Guengerich, L.C. Gunsalus, E.F. Johnson, J.C. Loper, K. Sato, M.R. Waterman, D.J. Waxman, The P450 superfamily: Update on new sequences, gene mapping and recommended nomenclature, DNA Cell Biol. 10 (1991) 1-14.
68. F.J. Gonzalez, Human cytochromes P450: problems and prospects, Trends Pharmacol. Sci. 13 (1992) 346-352.
69. M. Murray, P450-enzymes-inhibition mechanisms, genetic regulation and effects of liver disease, Clin. Pharmacokin. 23 (1992) 132-146.
70. S.A. Wrighton, J.C. Stevens, The human hepatic cytochromes P450 involved in drug metabolism, Crit. Rev. Toxicol. 22 (1992) 1-22.
71. C.H.Y. Yun, T. Shimada, P.F. Guengerich, Roles of human liver cytochrome P4502C and 3A enzymes in the 3-hydroxylation of benzo(a)pyrene, Cancer Res. 52 (1992) 1868-1874.
72. L.M. Bornheim, M.A. Correia, Selective inactivation of mouse liver cytochrome P450IIIA by cannabidiol, Mol. Pharmacol. 38 (1990) 319-326.
73. M. Kitada, T. Kamatald, K. Itahashi, T. Rikihisa, Y. Kanakubo, Significance of cytochrome P-450 (P.450 HULa) of human fetal livers in the steroid and drug oxidation, Biochem. Pharmacol. 36 (1987) 453-456.
74. J. Mäenpää, O. Pelkonen, T. Cresteil, A. Rane, The role of cytochrome P450 3A (CYP3A) isoform(s) in oxidative metabolism of testosterone and benzphetaniine in human adult and fetal liver, J. Steroid Biochem. Mol. Biol. 44 (1993) 61-67.
75. J. Mäenpää, A. Rane, H. Raunio, P. Honkakoski, O. Pelkonen, Cytochrome P450 isoforms in human fetal tissues related to phenobarbital-inducible forms in the mouse, Biochem. Pharmacol. 45 (1993) 899-907.
76. J.D. Schuetz, S. Kauma, RS. Guzelian, Identification of the fetal liver cytochrome-CYP3A7 in human endometrium and placenta, J. Clin. Invest. 92 (1993) 1018-1024.
77. D.L. Simmons, C.B. Kasper, Quantitation of mRNAs specific for the mixed-function oxidase system in rat liver and extrahepatic tissues during development, Arch. Biochem. Biophys. 271 (1989) 10-20.
78. Y. Namakura, S.-I. Ikeda, T. Furukawa, T. Sumizawa, A. Tani, S.-I. Akiyama, Y. Nagata, Function of P-glycoprotein expressed in placenta and mole, Biochem. Biophys. Res. Commun. 235 (1997) 849-853.
79. M. Pasanen, O. Pelkonen, Purification and immunological characterization of human placental mitochondrial cytochrome P450, J. Steroid Biochem. 24 (3) (1986) 669-675.
80. B.C. Chung, K.J. Malteson, K. Voutilainen, T.K. Mohandas, W.I. Tiller, Human cholesterol side-chain cleavage enzyme, P450scc: cDNA cloning, assignment of the gene to chromosome 15 and the expression in the placenta, Proc. Natl. Acad. USA 83 (1986) 8963-8966.
81. E.A.J. Thompson, RK. Siiteri, Utilization of oxygen and reduced nicotinamide adenine dinucleotide phosphate by human placental microsomes during aromatization of androstenedione, J. Biol. Chem. 249 (1974) 5364-5372.
82. E.A.J. Thompson, P.K. Siiteri, The involvement of human placental microsomal cytochrome P-450 in aromatization, J. Biol. Chem. 249 (1974) 5373-5378.
83. J. Kitawaki, S. Inoue, T. Tamura, T. Yamamoto, T. Nogushi, Y. Osawa, H. Okada, Increasing aromatase cytochrome P-450 level in human placenta during pregnancy: studied by immunohistochemistry and enzyme-linked immunosorbent assay, Endocrinology 130 (1992) 2751-2757.
84. S. Nakajin, M. Shinoda, P.R. Hall, Purification to homogeneity of aromatase from human placenta, Biochem. Biophys. Res. Commun. 134 (1986) 701-710.
85. J.T. Kellis, L.E. Vickery, Purification and characterization of human placental aromatase cytochrome P-450, J. Biol. Chem. 262 (9) (1987) 4413-4420.
86. C.T. Evans, D.B. Ledesma, T.Z. Schulz, P.R. Simpson, C.R. Mendeison, Isolation and characterization of a complementary DNA specific for human aromatase system cytochrome P-450 mRNA, Proc. Natl. Acad. Sci. USA 83 (1986) 6389-6391.
87. E.K. Simpson, M.W. Kilgore, M.S. Mahendroo, G.D. Means, C.J. Corbin, C.R. Mendelson, Regulation of human aromatase cytochrome-P450 gene expression, J. Steroid. Biochem. Mol. Biol. 43 (1992) 923-930.
88. E. Simpson, M. Michael, V. Agarwal, M. Hinshelwood, S. Bulun, Y. Zhao, Expression of CYP19 (aromatase) gene: an usual case of alternative promotor usage, FASEB J. 11 (1997) 29-36.
89. F.J. Gonzalez, The molecular biology of cytochrome P450s, Pharmacol. Rev. 40 (1989) 243-288.
90. D.J. Waxman, D.P. Lapenson, T. Aoyama, H.V. Gelboin, F.J. Gonzalez, K. Korzekwa, Steroid hormone hydroxylase specificities of eleven cDNA-expressed human cytochrome P450s, Arch. Biochem. Biophys. 290 (1991) 160-166.
91. D. Roe, B. Little, R. Bawdon, L. Gilstrap, Metabolism of cocaine by human placentas: implications for fetal exposure, Am. J. Obstet. Gynaecol. 163 (1990) 715-718.
92. L.A. Sheean, Aromatization of androstenedione by microsomes from the human placenta after gestational alcohol consumption, Alcoholism Clin. Exp. Res. 7 (1983) 93-94.
93. E.T. Morgan, Suppression of constitutive cytochrome P-450 gene expression in livers of rats undergoing an acute phase response to endotoxin, Mol. Pharmacol. 36 (1989) 699-707.
94. K.W. Renton, L.C. Knickle, Regulation of hepatic cytochrome P-450 during infectious disease, Can. J. Physiol. Pharmacol. 68 (1990) 777-781.
95. K. Wright, E.T. Morgan, Regulation of cytochrome P450II2C12 expression by interleukin-1α, interleukin-6, and dexamehasone, Mol. Pharmacol. 39 (1991) 468-474.
96. J.Y.Y. Wong, E.J.D. Le, S.M. Moochhala, The effects of an interferon inducer, polyriboinosinic polyribocytidylic acid on cytochrome P-450 dependent hepatic progesterone metabolism, Life Sci. 53 (1993) 1893-1901.
97. S.I. Shedlofsky, R.C. Israel, C.J. McClain, D.B. Hill, R.A. Blouin, Endotoxin administration to humans inhibits hepatic cytochrome P450-mediated drug metabolism, J. Clin. Invest. 94 (1994) 2209-2214.
98. G.M. Kirby, P. Pelkonen, V. Vatanasapt, A.-M. Camus, C.P. Wild, M.A. Lang, Association of liver fluke (Opisthorchis viverrini) infestation with increased expression of cytochrome P450 and carcinogen metabolism in male hamster liver, Mol. Carcinog. 11 (1994) 81-89.
99. G.M. Kirby, I. Cheinin, R.V. Montesano, M.A. Lang, C.P. Wild, Induction of specific cytochrome P450s involved in aflatoxin B1 metabolism in hepatitis B virus transgenic mice, Mol. Carcinog. 11 (1994) 74-80.
100. P. Pellinen, F. Stenback, A. Kojo, P. Honkakoski, H. Gelboin, M. Pasanen, Regenerative changes in hepatic morphology and enhanced expression of CYP2B10 and CYP3A during daily administration of cocaine, Hepatology 23 (1996) 515-523.
101. S.D.Z. Avigdor, B. Barnea, Quinone reductase activity in the first trimester placenta: Effect of cigarette smoking and polycyclic aromatic hydrocarbons, Reprod. Toxicol. 6 (1992) 363-366.
102. A. Boden, P. Bush, M. Burke, D. Abramovich, P. Aggett, T. Mayhew, K. Page, Human placental cytochrome P450 and quinone reductase enzyme induction in relation to maternal smoking, Reprod. Fertil. Dev. 7 (1995) 1521-1524.
103. W. Boadi, J. Urbach, B. Barnea, J. Brandes, S. Yannai, In vitro effect of mercury on aryl hydrocarbon hydroxylase, quinone reductase, catecholamine-O-methyltransferase and glucose-6-phosphate dehydrogenase activities in term human placenta, Pharmacol. Toxicol. 68 (1991) 317-321.
104. K. Conrad, M. Vill, P. McGuire, W. Dail, A. Davis, Expression of nitric oxide synthase by syncytiotrophoblast in human placental villi, FASEB J. 7 (1993) 1269-1276.
105. F. Coceani, Control of the ductus arteropsis - A new function for cytochrome P450, endothelin and nitric oxide, Biochem. Pharmacol. 48 (1994) 1315-1318.
106. I. Buhimschi, C. Yallampalli, K. Chwalisz, K. Garfield, Pre-eclampsia-like conditions produced by nitric oxide inhibition: effects of L-arginine, D-arginine and steroid hormones, Human Reprod. 10 (1995) 2723-2730.
107. B. Mannervik, M. Widersten, Human glutathione S-transferases: classification, tissue distribution, structure and functional properties, in: G. Pacifici, G. Fracuhia (Eds.), Advances in Drug Metabolism in Man, Officer for Official Publications of the European Communities, Luxembourg, 1995, pp. 407-460, Chapter 12.
108. C. Guthenberg, B. Mannervik, (Glutathione S-transferase (transferase pii) from human placenta is identical or closely related to glutathione S-transferase (transferase pii) from erythrocytes, Biochem. Biophys. Acta 661 (1981) 255-260.
109. N. Nakasa, N. Mera, S. Ohmori, K.T.I. Itahashi, I. Ishii, K. Kitaada, Nucleotide sequence of pi class glutathione S-transferase in human fetal liver, Res. Commun. Mol. Pathol. Pharmacol. 97 (1997) 67-78.
110. D. Mcrobie, D. Glover, T. Tracy, Regiospecificity of placental metabolism by cytochromes P450 and glutathione S-transferase, Gynecol. Obstet. Invest. 42 (1996) 154-158.
111. A. Mitra, S. Govindwar, P. Josep, A. Kulkarni, Inhibition of human term placental and fetal liver glutathione S-tranferase by fatty acids and fatty acid esters, Toxicol. Lett. 60 (1992) 281-288.
112. C.D. Ilio, G. Polidoro, N. Arduini, A. Mucci, G. Federichi, Glutathione peroxidase, glutathione reductase, glutathione S-transferase, and g-glutamyltranspeptidase activities in the human early pregnancy placenta, Biochem. Med. 29 (1983) 143-148.
113. G.M. Pacffici, A. Kane, Glutabione S-tranferase in the human placenta at different stages of pregnancy, Drug Metab. Dispos. 9 (1981) 472-475.
114. G.M. Pacifici, A. Rane, Epoxide hydrolase in human placenta at different stages of pregnancy, Dev. Pharmacol. Ther. 6 (1983) 83-93.
115. M. Sanyal, Y-L. Li, W. Riggers, J. Satis, E. Barnea, Augmentation of polynuclear aromatic hydrocarbon metabolism of human placental tissues of first-trimester pregnancy by cigarette smoke exposure, Am. J. Obstet. Gynecol. 168 (1993) 1587-1587.
116. G. Ricci, G. Del Boccio, A. Permelli, M. Lo Beilo, K. Petrizelli, A. Caccuni, D. Barra, G. Federici, Redox forms of human placenta glutathione transferase, J. Biol. Chem. 266 (1991) 21409-21415.
117. T. Nishihara, H. Maeda, K. Okamoto, N.Y.M. Oshida, T. Tereda, Inactivation of human placental glutathione-S-transferase by SH/SS exchange reaction with biological disulfides, Biochem. Biophys. Res. Commun. 174 (1991) 580-585.
118. V. Daniel, Glutathione S-transferases: gene structure and regulation of expression, CRC Rev. Biochem. Mol. Biol. 28 (1993) 173-207.
119. T. Rushmore, C. Pickett, Glutathione S-transferase, structure, regulation, and therapeutic implications, J. Biol. Chem. 268 (1993) 11475-11478.
120. A. Cholon, A. Giaccia, A. Lewis, I. Hickson, J. Brown, What role do glutathione S-transferases play in the cellular response to ionising radiation, Int. J. Radiation Oncol. Biol. Phys. 22 (1992) 759-763.
121. M.Y. Obolenskaya, T.L. Tschaikovskaya, L.M. Lebedeva, L.L. Macewicz, O.M. Didenco, K. Decker, Glutathione status of placentae from differently polluted regions of Ukraine, Eur. J. Obstet. Gynecol. 71 (1997) 23-30.
122. S. Liu, S. Stoesz, C. Pickett, Identification of a novel human glutathione S-transferase using bioinformatics, Arch. Biochem. Biophys. 352 (1998) 306-313.
123. G. Pacifici, G. Fracchia, Advances in drug metabolism in man, in: Science, Research and Development, European Commission, Directorate General Xiii, Telecommunications, Information Market and Exploitation of Research, L-2920, European Commission, Luxembourg, 1995, p. 837.
124. K. Finnell, B. Buehler, B. Kerr, P. Ager, K. Levy, Clinical and experimental studies linking oxidative metabolism to phenytoin-linked teratogenesis, Neurology 4 (5) (1992) 25-31.
125. S. Kaneko, Antiepileptic drug therapy and reproductive consequences: Functional and morphological effect, Reprod. Toxicol. 5 (1991) 179-198.
126. G. Pacifici, C. De'Santi, Human sulphotransferase, classification and metabolic profile of the major isoforms, the point of view of the clinical pharmacologist, in: G. Pacifici, G. Fracchia (Eds.), Advances in Drug Metabolism in Man, Officer for Official Publications of the European Communities, Luxembourg, 1995, pp. 311-350, Chapter 10.
127. C. Omieciuski, L. Aicher, L. Swenson, Developmental expression of human microsomal epoxide hydrolase, J. Pharmacol. Exp. Ther. 269 (1994) 417-423.
128. F. Bernier, G. Leblanc, F. Labrie, V. Luu-The, Structure of human estrogen and aryl sulfotransferase gene. Two mRNA species issued from a single gene, J. Biol. Chem. 269 (1994) 28200-28205.
129. M. Capiello, L. Giuliani, A. Rane, G.M. Pacifici, Dopamine sulphotransibrase is better developed than p-nitrophenol suplhotransferase in human fetus, Dev. Pharmacol. Ther. 16 (1991) 83-88.
130. K. Vatsis, W. Weber, D. Bell, J.-M. Dupret, D. Price Evans, D. Grant, D. Hein, H. Lin, U. Meyer, M. Relling, E. Sim, T. Suzuki, Y. Yamazoe, Nomenclature for N-acetyltranferases., Pharmacogenetics 5 (1995) 1-17.
131. L. Derewlany, G. Koren, Biotransformation of carcinogenic arylamines and arylamides by human placenta, J. Lab. Clin. Med. 124 (1994) 134-141.
132. L. Derewlany, B. Knie, G. Koren, Arylamine N-acetyl-transferase activity of the human placenta, J. Pharmacol. Exp. Ther. 269 (1994) 756-760.
133. M. Pasanen, O. Pelkonen, Solubilization and partial purification of human placental cytochromes P-450, Biochem. Biophys. Res. Commun. 103 (4) (1981) 1310-1317.
134. 2-precipitated human placental microsomes, Life Sci. 13 (1973) 1221-1230.
135. P.K. Zachariah, M.R. Juchau, Interactions of steroids with human placental cytochrome P-450 in the presence of carbon monoxide, Life Sci. 16 (1975) 1689-1692.
136. Q.P. Lee, P.K. Zachariah, M.R. Juchau, Differential inhibition of androst-4-en-3,17-dione aromatization by carbon monoxide in the presence of estr-4-en-3,17-dione, Steroids 26 (1975) 571-578.
137. S.T. Chao, M.K. Juchan, Interactions of endogenous and exogenous estrogenic compounds with human placental microsomal cytochrome P-450 (P-4SOhpm), J. Steroid Biochem. 13 (1980) 127-133.
138. P. Bergheim, G.H. Rathgen, K.J. Netter, Interaction of drugs and steroids with human placental microsomes, Biochem. Pharmacol. 22 (1973) 1633-1645.