Steroid Hormones and other Physiologic Regulators of Liver Cytochromes P450: Metabolic Reactions and Regulatory Pathways

Advances in Molecular and Cell Biology

Volumn 14, Issue C, 1996, Pages 341-374

  Waxman, David J ^a  

^a NONE

Author keywords

[No Author keywords available]

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EID: 33846664938     PISSN: 15692558     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S1569-2558(08)60349-5     Document Type: Article

References (180)

1. Andersson S., Davis D.L., Dahlback H., Jornvall H., and Russell D.W. Cloning, structure, and expression of the mitochondrial cytochrome P450 sterol 26-hydroxylase, a bile acid biosynthetic enzyme. J. Biol. Chem. 264 (1989) 8222-8229
2. Aoyama T., Korzekwa K., Nagata K., Adesnik M., Reiss A., Lapenson D.P., Gillette J., Gelboin H.V., Waxman D.J., and Gonzalez F.J. Sequence requirements for cytochrome P-450IIB1 catalytic activity. Alteration of the stereospecificity and regioselectivity of steroid hydroxylation by a simultaneous change of two hydrophobic amino acid residues to phenylalanine. J. Bio. Chem. 264 (1989) 21327-21333
3. Aoyama T., Korzekwa K., Nagata K., Gillette J., Gelboin H.V., and Gonzalez F.J. Estradiol metabolism by complementary deoxyribonucleic acid-expressed human cytochrome P450s. Endocrinology 126 (1990) 3101-3106
4. Argetsinger L.S., Campbell G.S., Yang X., Witthuhn B.A., Silvennoinen O., Ihie J.N., and Carter-Su C. Identification of JAK2 as a growth hormone receptor-associated tyrosine kinase. Cell 74 (1993) 237-244
5. Arlotto M.P., and Parkinson A. Identification of cytochrome P450a (P450IIA1) as the principal testosterone 7 alpha-hydroxylase in rat liver microsomes and its regulation by thyroid hormones. Arch. Biochem Biophys. 270 (1989) 458-471
6. Arnold A.P. Gonadal steroid induction of structural sex differences in the central nervous system. A. Rev. Neurosci. 7 (1984) 413-442
7. Ball S.E., Forrester L.M., Wolf C.R., and Back D.J. Differences in the cytochrome P-450 isoenzymes involved in the 2-hydroxylation of oestradiol and 17 alpha-ethinyloestradiol. Relative activities of rat and human liver enzymes. Biochem. J. 267 (1990) 221-226
8. Bandiera S., Ryan D.E., Levin W., and Thomas P.E. Age- and sex-related expression of cytochromes p450f and P450g in rat liver. Arch. Biochem. Biophys. 248 (1986) 658-676
9. Barnea E.R., MacLusky N.J., and Naftolin F. Catechol estrogens. Biochemical Actions of Hormones 11 (1984), Academic Press, Inc., New Haven, CT 267-307 11
10. Baxter R.C., and Zaltsman Z. Induction of hepatic receptors for growth hormone (GH) and prolactin by GH infusion is sex independent. Endocrinology 115 (1984) 2009-2014
11. Beck F., Plummer S., Senior P.V., Byrne S., Green S., and Brammar W.J. The ontogeny of peroxisome-proliferator-activated receptor gene expression in the mouse and rat. Proc. R. Soc. Lond. [Biol.] 247 (1992) 83-87
12. Bell D.R., and Elcombe C.R. Induction of acyl-CoA oxidase and cytochrome P450IVA1 RNA in rat primary hepatocyte culture by peroxisome proliferators. Biochem. J. 280 (1991) 249-253
13. Bick T., Youdim M.B.H., and Hochberg Z. Adaptation of liver membrane somatogenic and lactogenic growth hormone (GH) binding to the spontaneous pulsation of GH secretion in the male rat. Endocrinology 125 (1989) 1711-1717
14. Bick T., Youdim M.B.H., and Hochberg Z. The dynamics of somatogenic and lactogenic growth hormone binding: Internalization to Golgi fractions in the male rat. Endocrinology 125 (1989) 1718-1722
15. Bjorkhem I. Mechanism of bile acid biosynthesis in mammalian liver. In: Danielsson S.J. (Ed). Sterols and Bile Acids (1985), Elsevier, New York 231-278
16. Brueggemeier R.W. Kinetics of rat liver microsomal estrogen 2-hydroxylase. Evidence for sex differences at initial velocity conditions. J. Biol. Chem. 256 (1981) 10239-10242
17. Bucala R., Fishman J., and Cerami A. Formation of covalent adducts between Cortisol and 16alpha-hydroxyestrone and protein: Possible role in the pathogenesis of Cortisol toxicity and systemic lupus erythematosus. Proc. Natl. Acad. Sci. USA 79 (1982) 3320-3324
18. Bulger W.H., and Kupper D. Effect of xenobiotic estrogens and structurally related compounds on 2-hydroxylation of estradiol and on other monooxygenase activities in rat liver. Biochem. Pharmacol. 32 (1983) 1005-1010
19. Burbach K.M., Poland A., and Bradfield C.A. Cloning of the Ah-receptor cDNA reveals a distinctive ligand-activated transcription factor. Proc. Natl. Acad. Sci. USA 89 (1992) 8185-8189
20. Burger H.J., Schuetz J.D., Schuetz E.G., and Guzelian P.S. Paradoxical transcriptional activation of rat liver cytochrome P-450 3A1 by dexamethasone and the anti glucocorticoid pregnenolone 16 alpha-carbonitrile: Analysis by transient transfection into primary monolayer cultures of adult rat hepatocytes. Proc. Natl. Acad. Sci. USA 89 (1992) 2145-2149
21. Cheng K.C., and Schenkman J.B. Testosterone metabolism by cytochrome P-450 isozymes RLM3 and RLM5 and by microsomes. Metabolite identification. J. Biol. Chem. 258 (1983) 11738-11744
22. Colby H.D. Regulation of hepatic drug and steroid metabolism by androgens and estrogens. Adv. Sex Horm. Res. 4 (1980) 27-71
23. Conney A.H. Pharmacological implications of microsomal enzyme induction. Pharmacol. Rev. 19 (1967) 317-366
24. Conney A.H. Induction of microsomal enzymes by foreign chemicals & carcinogenesis by polycyclic aromatic hydrocarbons: G.H.A. Clowes memorial lecture. Cancer Res. 42 (1982) 4875-4917
25. Conway J.G., Cattley R.C., Popp J.A., and Butterworth B.E. Possible mechanisms in hepatocarcinogenesis by the peroxisome proliferator di(2-ethylhexyl) phthalate. Drug Metab. Rev. 21 (1989) 65-102
26. Conway J.G., Tomaszewski K.E., Olson M.J., Cattley R.C., Marsman D.S., and Popp J.A. Relationship of oxidative damage to the hepatocarcinogenicity of the peroxisome proliferators di(2-ethylhexyl)phthalate and Wy-14, 643. Carcinogenesis 10 (1989) 513-519
27. Cunningham B.C., Ultsch M., de Vos A.M., Mulkerrin M.G., Clauser K.R., and Wells J.A. Dimerization of the extracellular domain of the human growth hormone receptor by a single hormone molecule. Science 254 (1991) 821-825
28. Dannan G.A., Guengerich F.P., and Waxman D.J. Hormonal regulation of rat liver microsomal enzymes Role of gonadal steroids in programming, maintenance, and suppression of delta 4-steroid 5 alpha-reductase, flavin-containing monooxygenase, and sex-specific cytochromes P-450. J. Biol. Chem. 261 (1986) 10728-10735
29. Dannan G.A., Porubek D.J., Nelson S.D., Waxman D.J., and Guengerich F.P. 17 beta-estradiol 2- and 4-hydroxylation catalyzed by rat hepatic cytochrome P-450: Roles of individual forms, inductive effects, developmental patterns, and alterations by gonadectomy and hormone replacement. Endocrinology 118 (1986) 1952-1960
30. Denner L.A., Weigel N.L., Maxwell B.L., Schrader W.T., and O'Malley B.W. Regulation of progesterone receptor-mediated transcription by phosphorylation. Science 250 (1990) 1740-1743
31. Doglio A., Dani C., Grimaldi P., and Ailhaud G. Growth hormone stimulates c-fos gene expression by means of protein kinase C without increasing inositol lipid turnover. Proc. Natl. Acad. Sci. USA 86 (1989) 1148-1152
32. Dreyer C., Krey G., Keller H., Givel F., Helftenbein G., and Wahli W. Control of the peroxisomal beta-oxidation pathway by a novel family of nuclear hormone receptors. Cell 68 (1992) 879-887
33. Fahl W.E., Lalwani N.D., Watanabe T., Goel S.K., and Reddy J.K. DNA damage related to increased hydrogen peroxide generation by hypolipidemic drug-induced liver peroxisomes. Proc. Natl. Acad. Sci. USA 81 (1984) 7827-7830
34. Fisher D., Labbe G., Berson A., Tinel M., Loeper J., Larrey D., and Pessayre D. Inhibition of rat liver estrogen 2/4-hydroxylase activity by troleandomycin: Comparison with erythromycin and roxithromycin. J. Pharmacol. Exp. Ther. 254 (1990) 1120-1127
35. Fishman J. Aromatic hydroxylation of estrogens. Ann. Rev. Physiol. 45 (1983) 61-72
36. Fishman J., Bradlow H.L., Schneider J., Anderson K.E., and Kappas A. Radiometric analysis of biological oxidations in man: Sex differences in estradiol metabolism. Proc. Natl. Acad. Sci. USA 77 (1980) 4957-4960
37. Gebel T., Arand M., and Oesch F. Induction of the peroxisome proliferator activated receptor by fenofibrate in rat liver. FEBS Lett. 309 (1992) 37-40
38. Ged C., Rouillon J.M., Pichard L., Combalbert J., Bressot N., Bories P., Michel H., Beaune P., and Maurel P. The increase in urinary excretion of 6 beta-hydroxycortisol as a marker of human hepatic cytochrome P450IIIA induction. Br. J. Clin. Pharmacol. 28 (1989) 373-387
39. Gonzalez F.J., Crespi C.L., and Gelboin H.V. cDNA-expressed human cytochrome P450s: a new age of molecular toxicology and human risk assessment. Mutation Research 247 (1991) 113-127
40. Gonzalez F.J., Kimura S., Song B.J., Pastewka J., Gelboin H.V., and Hardwick J.P. Sequence of two related P-450 mRNAs transcriptionally increased during rat development. An R.dre.l sequence occupies the complete 3′ untranslated region of a liver mRNA. J. Biol. Chem. 261 (1986) 10667-10672
41. Gonzalez F.J., Song B.J., and Hardwick J.P. Pregnenolone 16 alpha-carbonitrile-inducible P450 gene family: Gene conversion and differential regulation. Mol. Cell Biol. 6 (1986) 2969-2976
42. Gordon G.B., Shantz L.M., and Talalay P. Modulation of growth, differentiation and carcinogenesis by dehydroepiandrosterone. Adv. Enz. Reg. 26 (1987) 355-382
43. Gottlicher M., Widmark E., Li Q., and Gustafsson J.A. Fatty acids activate a chimera of the clofibric acid-activated receptor and the glucocorticoid receptor. Proc. Natl. Acad. Sci. USA 89 (1992) 4653-4657
44. Graham M.J., Lucier G.W., Linko P., Maronpot R.R., and Goldstein J.A. Increases in cytochrome P-450 mediated 17 beta-estradiol 2-hydroxylase activity in rat liver microsomes after both acute administration and subchronic administration of 2, 3, 7, 8-tetrachlorodibenzo-p-dioxin in a two-stage hepatocarcinogenesis model. Carcinogenesis 9 (1988) 1935-1941
45. Green S. Receptor-mediated mechanisms of peroxisome proliferators. Biochem. Pharmacol. 43 (1992) 393-401
46. Guengerich F.P. Enzymology of rat liver cytochromes P450. In: Guengerich F.P. (Ed). Mammalian Cytochromes P450 (1987), CRC Press, Boca Raton, FL 1-54
47. Guengerich F.P., and Shimada T. Oxidation of toxic and carcinogenic chemicals by human cytochrome P-450 enzymes. Chem. Res. Toxicol. 4 (1991) 391-407
48. Gurland G., Ashcom G., Cochran B.H., and Schartz J. Rapid events in growth hormone action Induction of c-fos and c-jun transcription in 3T3-F442A preadipocytes. Endocrinology 127 (1990) 3187-3195
49. Gustafsson J.A., Mode A., Norstedt G., and Skett P. Sex steroid induced changes in hepatic enzymes. A Rev. Physiol. 45 (1983) 51-60
50. Guzelian P.S., Li D., Schuetz E.G., Thomas P., Levin W., Mode A., and Gustafsson J.A. Sex change in cytochrome P-450 phenotype by growth hormone treatment of adult rat hepatocytes maintained in a culture system on matrigel. Proc. Natl. Acad. Sci. USA 85 (1988) 9783-9787
51. Harada N., and Negishi M. Substrate specificities of cytochrome P-450, C-P-450(16)alpha and P-450(l5)alpha, and contribution to steroid hydroxylase activities in mouse liver microsomes. Biochem. Pharmacol. 37 (1988) 4778-4780
52. Hardwick J.P., Song B.J., Huberman E., and Gonzalez F.J. Isolation, complementary DNA sequence, and regulation of rat hepatic lauric acid omega-hydroxylase (cytochrome P450 LA omega): Identification of a new cytochrome P450 gene family. J. Biol. Chem. 262 (1987) 801-810
53. Hochberg Z., Bick T., and Harel Z. Alterations of human growth hormone binding by rat liver membranes during hypo- and hyperthyroidism. Endocrinology 126 (1990) 325-329
54. Huber W., Kraupp G.B., Esterbauer H., and Schulte H.R. Role of oxidative stress in age dependent hepatocarcinogenesis by the peroxisome proliferator nafenopin in the rat. Cancer Res. 51 (1991) 1789-1792
55. Hunt C.M., Watkins P.B., Saenger P., Stave G.M., Barlascini N., Watlington C.O., Wright J.J., and Guzelian P.S. Heterogeneity of CYP3A isoforms metabolizing erythromycin and Cortisol. Clin. Pharmacol. Ther. 51 (1992) 18-23
56. Inano H., Suzuki K., Wakabayashi K., and Tamaoki B.I. Biological activities of 7 alphahydroxylated C19-steroids and changes in rat testicular 7 alpha-hydroxylase activity with gonadal status. Endocrinology 92 (1973) 22-30
57. Issemann I., and Green S. Activation of a member of the steroid hormone receptor superfamily by peroxisome proliferators. Nature 347 (1990) 645-650
58. Janeczko R., Waxman D.J., Le B.G., Morville A., and Adesnik M. Hormonal regulation of levels of the messenger RNA encoding hepatic P450 2c (IIC11) a constitutive male-specific form of cytochrome P450. Mol. Endocrinol. 4 (1990) 295-303
59. Jansson J.O., Ekberg S., and Isaksson O. Sexual dimorphism in the control of growth hormone secretion. Endocrine Rev. 6 (1985) 128-150
60. Jellinck P.H., and Fishman J. Activation and irreversible binding of regiospecifically labeled catechol estrogen by rat liver microsomes: Evidence for differential cytochrome P-450 catalyzed oxidations. Biochemistry 27 (1988) 6111-6116
61. Johnson R.M., Napier M.A., Cronin M.J., and King K.L. Growth hormone stimulates the formation of sn-l, 2-diacylglycerol in rat hepatocytes. Endocrinology 127 (1990) 2099-2103
62. Kaikaus R.M., Chan W.K., Lysenko N., Ray R., Ortiz de Montellano P.R., and Bass N.M. Induction of peroxisomal fatty acid beta-oxidation and liver fatty acid binding protein by peroxisome proliferators: Mediation via the cytochrome P450IVA1 omega-hydroxylase pathway. J. Biol. Chem. 268 (1993) 9593-9603
63. Kato R. Sex-related differences in drug metabolism. Drug Metab. Rev. 3 (1974) 1-32
64. Kato R., Yamazoe Y., Shimada M., Murayama N., and Kamataki T. Effect of growth hormone and ectopic transplantation of pituitary gland on sex-specific forms of cytochrome P450 and testosterone and drug oxidations in rat liver. J Biochem. 100 (1986) 895-902
65. Keller H., Dreyer C., Medin J., Mahfoudi A., Ozato K., and Wahli W. Fatty acids and retinoids control lipid metabolism through activation of peroxisome proliferator-activated receptor-retinoid X receptor heterodimers. Proc. Natl. Acad. Sci. USA 90 (1993) 2160-2164
66. Kimura S., Hanioka N., Matsunaga E., and Gonzalez F.J. The rat clofibrate-inducible CYP4A gene subfamily I. Complete intron and exon sequence of the CYP4A1 and CYP4A2 genes, unique exon organization, and identification of a conserved 19-bp upstream element. DNA 8 (1989) 503-516
67. Kimura S., Hardwick J.P., Kozak C.A., and Gonzalez F.J. The rat clofibrate-inducible CYP4A subfamily II cDNA sequence of IVA3, mapping of the Cyp4a locus to mouse chromosome 4, and coordinate and tissue-specific regulation of the CYP4A genes. DNA 8 (1989) 517-525
68. Kliewer S.A., Umesono K., Noonan D.J., Heyman R.A., and Evans R.M. Convergence of 9-cis retinoic acid and peroxisome proliferator signalling pathways through heterodimer formation of their receptors. Nature 358 (1992) 771-774
69. Kronbach T., Larabee T.M., and Johnson E.F. Hybrid cytochromes P-450 identify a substrate binding domain in P-450IIC5 and P-450IIC4. Proc. Natl. Acad. Sci. USA 86 (1989) 8262-8265
70. Kupfer D., Miranda G.K., and Bulger W.H. A facile assay for 2-hydroxylation of estradiol by liver microsomes. Anal. Biochem. 116 (1981) 27-34
71. Lahita R.G., Bradlow H.L., Kunkel H.G., and Fishman J. Increased 16alpha-hydroxylation of estradiol in systemic lupus erythematosus. J Clin. Endocrinol. Metab. 53 (1981) 174-178
72. Lazarow P.B., and Fujiki Y. Biogenesis of peroxisomes. Ann. Rev. Cell Biol. 1 (1985) 489-530
73. Lee S.S., Pineau T., Drago J., Lee E.J., Owens J.W., Kroetz D.L., Fernandez-Salguero P.M., Westphal H., and Gonzalez F.J. Targeted disruption of the alpha isoform of the peroxisome proliferator-activated receptor gene in mice results in abolishment of the pleiotropic effects of peroxisome proliferators. Mol. Cell. Biol. 15 (1995) 3012-3022
74. Legraverend C., Mode A., Wells T., Robinson I., and Gustafsson J.A. Hepatic steroid hydroxylating enzymes are controlled by the sexually dimorphic pattern of growth hormone secretion in normal and dwarf rats. Faseb. J. 6 (1992) 711-718
75. Legraverend C., Mode A., Westin S., Strom A., Eguchi H., Zaphiropoulos P.G., and Gustafsson J.A. Transcriptional regulation of rat P-450 2C gene subfamily members by the sexually dimorphic pattern of growth hormone secretion. Mol. Endocrinol. 6 (1992) 259-266
76. Leo M.A., Iida S., and Lieber C.S. Retinoic acid metabolism by a system reconstituted with cytochrome P-450. Arch. Biochem. Biophys. 234 (1984) 305-312
77. Leung D.W., Spencer S.A., Cachianes G., Hammonds R.G., Collins C., Henzel W.J., Barnard R., Waters M.J., and Wood W.I. Growth hormone receptor and serum binding protein: Purification, cloning and expression. Nature 330 (1987) 537-543
78. Levin W., Thomas P.E., Ryan D.E., and Wood A.W. Isozyme specificity of testosterone 7 alpha-hydroxylation in rat hepatic microsomes: Is cytochrome P-450a the sole catalyst? Arch. Biochem. Biophys. 258 (1987) 630-635
79. Li J.J., and Li S.A. Estrogen carcinogenesis in Syrian hamster tissues: Role of metabolism. Fed. Proc. 46 (1987) 1858-1863
80. MacGeoch C., Morgan E.T., and Gustafsson J.A. Hypothalamo-pituitary regulation of cytochrome P450(15) beta apoprotein levels in rat liver. Endocrinology 117 (1985) 2085-2092
81. Malee M.P., and Mellon S.H. Zone-specific regulation of two messenger RNAs for P450c11 in the adrenals of pregnant and nonpregnant rats. Proc. Natl. Acad. Sci. USA 88 (1991) 4731-4735
82. Mathews L.S., Enberg B., and Norstedt G. Regulation of rat growth hormone receptor gene expression. J. Biol. Chem. 264 (1989) 9905-9910
83. McClellan G.P., Linko P., Yeowell H.N., and Goldstein J.A. Hormonal regulation of male-specific rat hepatic cytochrome P-450g (P-450IIC13) by androgens and the pituitary. J. Biol. Chem. 264 (1989) 18960-18965
84. McClellan G.P., Waxman D.J., Caveness M., and Goldstein J.A. Phenotypic differences in expression of cytochrome P-450g but not its mRNA in outbred male Sprague-Dawley rats. Arch. Biochem. Biophys. 253 (1987) 13-25
85. Michnovicz J.J., Hershcopf R.J., Naganuma H., Bradlow H.L., and Fishman J. Increased 2-hydroxylation of estradiol as a possible mechanism for the anti-estrogenic effect of cigarette smoking. New Eng. J. Med. 315 (1986) 1305-1309
86. Milton M.N., Elcombe C.R., and Gibson G.G. On the mechanism of induction of microsomal cytochrome P450IVA1 and peroxisome proliferation in rat liver by clofibrate. Biochem. Pharmacol. 40 (1990) 2727-2732
87. Mittler J.C. Studies on the kinetics of the interaction of 7 alpha-hydroxy-testosterone with the steroid 5 alpha-reductase. Steroids 45 (1985) 153-239
88. Mode A., Gustafsson J.A., Jansson J.O., Eden S., and Isaksson O. Association between plasma level of growth hormone and sex differentiation of hepatic steroid metabolism in the rat. Endocrinology 111 (1982) 1692-1697
89. Mode A., Wiersma-Larsson E., and Gustafsson J.A. Transcriptional and posttranscriptional regulation of sexually differentiated rat liver cytochrome P450 by growth hormone. Molec. Endocr. 3 (1989) 1142-1147
90. Morgan E.T., MacGeoch C., and Gustafsson J.A. Hormonal and developmental regulation of expression of the hepatic microsomal steroid 16alpha-hydroxylase cytochrome P-450 apoprotein in the rat. J. Biol. Chem. 260 (1985) 11895-11898
91. Morishima N., Yoshioka H., Higashi Y., Sogawa K., and Fujii-Kuriyama Y. Gene structure of cytochrome P450(M-1) specifically expressed in male rat liver. Biochemistry (1987) 26
92. Muerhoff A.S., Griffin K.J., and Johnson E.F. The peroxisome proliferator-activated receptor mediates the induction of CYP4A6, a cytochrome P450 fatty acid w-hydroxylase, by clofibric acid. J. Biol. Chem. 267 (1992) 19051-19053
93. Mukai K., Imai M., Shimada H., and Ishimura Y. Isolation and characterization of rat CYP11B genes involved in late steps of mineralo- and glucocorticoid syntheses. J. Biol. Chem. 268 (1993) 9130-9137
94. Negishi M., Iwasaki M., Juvonen R.O., and Aida K. Alteration of the substrate specificity of mouse 2A P450s by the identity of residue-209: Steroid-binding site and orientation. J. Steroid Biochem. Molec. Biol. 43 (1992) 1031-1036
95. Nelson D.R., Kamataki T., Waxman D.J., Guengerich F.P., Estabrook R.W., Feyereisen R., Gonzalez F.J., Coon M.J., Gunsalus I.C., Gotoh O., et al. The P450 superfamily: Update on new sequences, gene mapping, accession numbers, early trivial names of enzymes, and nomenclature. DNA Cell Biol. 12 (1993) 1-51
96. Noshiro M., and Negishi M. Pretranslational regulation of sex-dependent testosterone hydroxylases by growth hormone in mouse liver. J. Biol. Chem. 261 15 (1986) 923-927
97. Numazawa M., Satoh S., Ogura Y., and Nagaoka M. Determination of estradiol 2- and 16alpha-hydroxylase activities in rat liver microsomes using high-performance liquid chromatography. Anal. Biochem. 149 (1985) 409-414
98. Ogishima T., Shibata H., Shimada H., Mitani F., Suzuki H., Saruta T., and Ishimura Y. Aldosterone synthase cytochrome P450 expressed in the adrenals of patients with primary aldosteronism. J. Biol. Chem. 266 (1991) 10731-10734
99. Osumi T., Ishii N., Miyazawa S., and Hashimoto T. Isolation and structural characterization of the rat acyl-CoA oxidase gene. J. Biol. Chem. 262 (1987) 8138-8143
100. Osumi T., Wen J.K., and Hashimoto T. Two cis-acting regulatory sequences in the peroxisome proliferator-responsive enhancer region of rat acyl-CoA oxidase gene. Biochem. Biophys. Res. Commun. 175 (1991) 866-871
101. Peters J.M., Zhou Y.-C., Ram P.A., Lee S.S.T., Gonzalez F.J., and Waxman D.J. Peroxisome proliferator-activated receptor alpha mediates gene induction by dehydroepiandrosterone 3betasulfate. Molec. Pharm. (1996) (in press)
102. Prough R.A., Webb S.J., Wu H.Q., Lapenson D.P., and Waxman D.J. Induction of microsomal and peroxisomal enzymes by dehydroepiandrosterone and its reduced metabolite in rats. Cancer Res. 54 (1994) 2878-2886
103. Quail J.A., and Jellinck P.H. Modulation of catechol estrogen synthesis by rat liver microsomes: Effects of treatment with growth hormone or testosterone. Endocrinology 121 (1987) 987-992
104. Ram P.A., and Waxman D.J. Pretranslational control by thyroid hormone of rat liver steroid 5 alpha-reductase and comparison to the thyroid dependence of two growth hormone-regulated CYP2C mRNAs. J. Biol. Chem. 265 (1990) 19223-19229
105. Ram P.A., and Waxman D.J. Hepatic P450 expression in hypothyroid rats: Differential responsiveness of male-specific P450 forms 2a (IIIA2), 2c (IIC11), and RLM2 (IIA2) to thyroid hormone. Mol. Endocrinol. 5 (1991) 13-20
106. Ram P.A., and Waxman D.J. Thyroid hormone stimulation of NADPH P450 reductase expression in liver and extrahepatic tissues. Regulation by multiple mechanisms. J. Biol. Chem. 267 (1992) 3294-3301
107. Ram, P.A., & Waxman, D.J. 1993). Induction of cytochrome P450 4A (CYP) and acyl CoA oxidase mRNAs by dehydroepiandrosterone sulfate (DHEA-S) in primary rat hepatocyte culture. Endocrin. Soc. (Abstr.), in press.
108. Ram P.A., and Waxman D.J. Dehydroepiandrosterone 3 beta-sulphate is an endogenous activator of the peroxisome-proliferation pathway: induction of cytochrome P-450 4A and acyl-CoA oxidase mRNAs in primary rat hepatocyte culture and inhibitory effects of Ca(2+)-channel blockers. Biochem. J. 301 (1994) 753-758
109. Ram P.A., Park S.-H., Cho H.K., and Waxman D.J. Growth hormone activation of Stat 1, Stat 3, and Stat 5 in rat liver. Differential kinetics of hormone desensitization and growth hormone stimulation of both tyrosine phosphorylation and serine/threonine phosphorylation. J. Biol. Chem. 271 (1996) 5929-5940
110. Rao M.S., and Reddy J.K. Peroxisome proliferation and hepatocarcinogenesis. Carcinogenesis 8 (1987) 631-636
111. Reddy J.K., Goel S.K., Nemali M.R., Carrino J.J., Laffler T.G., Reddy M.K., Sperbeck S.J., Osumi T., Hashimoto T., Lalwani N.D., and Rao M.S. Transcriptional regulation of peroxisomal fatty acyl-CoA oxidase and enoyl-CoA hydratase/3-hydroxyacyl-CoA dehydrogenase in rat liver by peroxisome proliferators. Proc. Natl. Acad. Sci. USA 83 (1986) 1747-1751
112. Reddy J.K., and Rao M.S. Oxidative DNA damage caused by persistent peroxisome proliferation: Its role in hepatocarcinogenesis. Mutat. Res. 214 (1989) 63-68
113. Roupas P., and Herington A.C. Cellular mechanisms in the processing of growth hormone and its receptor. Molec. Cell. Endocr. 61 (1989) 1-12
114. Ryan D.E., and Levin W. Purification and characterization of hepatic microsomal cytochrome P-450. Pharmacol. Ther. 45 (1990) 153-239
115. Ryan D.E., Thomas P.E., Reik L.M., and Levin W. Purification, characterization and regulation of five rat hepatic microsomal cytochrome P450 isozymes. Xenobiotica 12 (1982) 727-744
116. Saenger P., Forster E., and Kream J. 6-Beta-hydroxycortisol: A noninvasive indicator of enzyme induction. J. Clin. Endocr. Metab. 52 (1981) 381-384
117. Samuels H.H., Forman B.M., Horowitz Z.D., and Ye Z.S. Regulation of gene expression by thyroid hormone. J. Clin. Invest. 81 (1988) 957-967
118. Sasamura H., Nagata K., Yamazoe Y., Shimada M., Saruta T., and Kato R. Effect of growth hormone on rat hepatic cytochrome P-450f rnRNA: a new mode of regulation. Mol. Cell Endocrinol. 68 (1990) 53-60
119. Schmidt A., Endo N., Rutledge S.J., Vogel R., Shinar D., and Rodan G.A. Identification of a new member of the steroid hormone receptor superfamily that is activated by a peroxisome proliferator and fatty acids. Mol. Endocrinol. 6 (1992) 1634-1641
120. Schneider J., Kinne D., Fracchia A., Pierce V., Anderson K.E., Bradlow H.L., and Fishman J. Abnormal oxidative metabolism of estradiol in women with breast cancer. Proc. Natl. Acad. Sci. USA 79 (1982) 3047-3051
121. Schuetz E.G., Wrighton S.A., Barwick J.L., and Guzelian P.S. Induction of cytochrome P450 by glucocorticoids in rat liver. I. Evidence that glucocorticoids and pregnenolone 16 alpha-carbonitrile regulate de novo synthesis of a common form of cytochrome P450 in cultures of adult rat hepatocytes and in the liver in vivo. J. Biol. Chem. 259 (1984) 1999-2006
122. Schwab G.E., and Johnson E.F. Variation in hepatic microsomal cytochrome P-450 1 concentration among untreated rabbits alters the efficiency of estradiol hydroxylation. Arch. Biochem. Biophys. 237 (1985) 17-26
123. Schwartz A.G., Whitcomb J.M., Nyce J.W., Lewbar M.L., and Pashko L.L. Dehydroepiandrosterone and structural analogs: A new class of cancer chemopreventive agents. Adv. Cancer Res. 51 (1988) 391-424
124. Shapiro B.H., MacLeod J.N., Pampori N.A., Morrissey J.J., Lapenson D.P., and Waxman D.J. Signaling elements in the ultradian rhythm of circulating growth hormone regulating expression of sex-dependent forms of hepatic cytochrome P450. Endocrinology 125 (1989) 2935-2944
125. Shapiro B.H., Pampori N.A., Lapenson D.P., and Waxman D.J. Growth hormone-dependent and -independent sexually dimorphic regulation of phenobarbital-induced hepatic cytochromes P450 2B1 and 2B2. Arch. Biochem. Biophys. 312 (1994) 234-239
126. Sharma R., Lake B.G., Foster J., and Gibson G.G. Microsomal cytochrome P452 induction and peroxisome proliferation by hypolipidaemic agents in rat liver. A mechanistic inter-relationship. Biochem. Pharmacol. 37 (1988) 1193-1201
127. Shaw G.C., and Fulco A.J. Barbiturate-mediated regulation of expression of the cytochrome P450BM-3 gene of Bacillus megaterium by Bm3R1 protein. J. Biol. Chem. 267 (1992) 5515-5526
128. Shaw G.C., and Fulco A.J. Inhibition by barbiturates of the binding of Bm3R1 repressor to its operator site on the barbiturate-inducible cytochrome P450BM-3 gene of Bacillus megaterium. J. Biol. Chem. 268 (1993) 2997-3004
129. Shaw P.M., Adesnik M., Weiss M.C., and Corcos L. The phenobarbital-induced transcriptional activation of cytochrome P450 genes is blocked by the glucocorticoid-progesterone antagonist RU486. Molec. Pharmacol. 44 (1993) 775-783
130. Sher T., Yi H.F., McBride O.W., and Gonzalez F.J. cDNA cloning, chromosomal mapping, and functional characterization of the human peroxisome proliferator activated receptor. Biochemistry 32 (1993) 5598-5604
131. Shimada M., Murayama N., Yamazoe Y., Kamataki T., and Kato R. Further studies on the persistence of neonatal androgen imprinting on sex-specific cytochrome P450, testosterone and drug oxidations. Jpn. J. Pharmacol. 45 (1987) 467-478
132. Silva C.M., Weber M.J., and Thorner M.O. Stimulation of tyrosine phosphorylation in human cells by activation of the growth hormone receptor. Endocrinology 132 (1993) 101-108
133. Skett P. Hormonal regulation and sex differences of xenobiotic metabolism. Prog. Drug Metab. 10 (1987) 85-139
134. Sonderfan A.J., Arlotto M.P., Dutton D.R., McMillen S.K., and Parkinson A. Regulation of testosterone hydroxylation by rat liver microsomal cytochrome P-450. Arch. Biochem. Biophys. 255 (1987) 27-41
135. Spink D.C., Eugster H.P., Lincoln II D.W., Schuetz J.D., Schuetz E.G., Johnson J.A., Kaminsky L.S., and Gierthy J.F. 17beta-estradiol hydroxylation catalyzed by human cytochrome P450 1A1: A comparison of the activities induced by 2, 3, 7, 8-tetrachlorodibenzo-p-dioxin in MCF-7 cells with those from heterologous expression of the cDNA. Arch. Biochem. Biophy. 293 (1992) 342-348
136. Squires E.J., and Negishi M. Reciprocal regulation of sex-dependent expression of testosterone 15 alpha-hydroxylase (P450(I5 alpha)) in liver and kidney of male mice by androgen Evidence for a single gene. J. Biol. Chem. 263 (1988) 4166-4171
137. Stefanini S., Ferrace M.G., and Argento M.P.C. Differentiation of liver peroxisomes in the foetal and newborn rat. Cytochemistry of catalase and D-aminoacid oxidase. J. Embryol. Exp. Morph. 88 (1985) 151-163
138. Subramanian A., Teixeira J.J.W., and Gil G. A STAT factor mediates the sexually dimorphic regulation of hepatic cytochrome P450 3A10/lithocholic acid 6beta-hydroxylase gene expression by growth hormone. Molec. Cell Biol. 15 (1995) 4672-4682
139. Sundseth S.S., Alberta J.A., and Waxman D.J. Sex-specific, growth hormone-regulated transcription of the cytochrome P450 2C11 and 2C12 genes. J. Biol. Chem. 267 (1992) 3907-3914
140. Sundseth S.S., and Waxman D.J. Sex-dependent expression and clofibrate inducibility of cytochrome P450 4A fatty acid omega-hydroxylases. Male specificity of liver and kidney CYP4A2 mRNA and tissue-specific regulation by growth hormone and testosterone. J. Biol. Chem. 267 (1992) 3915-3921
141. Swinney D.C., Ryan D.E., Thomas P.E., and Levin W. Regioselective progesterone hydroxylation catalyzed by eleven rat hepatic cytochrome P-450 isozymes. Biochemistry 26 (1987) 7073-7083
142. Theron C.N., Neethling A.C., and Taljard J.J.F. Ontogeny and sexual dimorphism of estradiol2-hydroxylase activity in rat liver microsomes. J. Steroid Biochem. 19 (1983) 1185-1190
143. Thummel K.E., Favreau L.V., Mole J.E., and Schenkman J.B. Further characterization of RLM2 and comparison with a related form of cytochrome P450, RLM2b. Archs. Biochem. Biophys. 266 (1988) 319-333
144. Tollet P., Enberg B., and Mode A. Growth hormone (GH) regulation of cytochrome P-450IIC12, insulin-like growth factor-I (IGF-I), and GH receptor messenger RNA expression in primary rat hepatocytes: A hormonal interplay with insulin, IGF-I, and thyroid hormone. Mol. Endocrinol 4 (1990) 1934-1942
145. Tollet P., Legraverend C., Gustafsson J.A., and Mode A. A role for protein kinases in the growth hormone regulation of cytochrome P4502C12 and insulin-like growth factor-I messenger RNA expression in primary adult rat hepatocytes. Mol. Endocrinol 5 (1991) 1351-1358
146. Tugwood J.D., Issemann I., Anderson R.G., Bundell K.R., McPheat W.L., and Green S. The mouse peroxisome proliferator activated receptor recognizes a response element in the 5′ flanking sequence of the rat acyl CoA oxidase gene. EMBO J. 11 (1992) 433-439
147. Wang X., Moller C., Norstedt G., and Carter-Su C. Growth hormone-promoted tyrosyl phosphorylation of a 121-kDa growth hormone receptor-associated protein. J. Biol. Chem. 268 (1993) 3573-3579
148. Watanabe K., Takanashi K., Imaoka S., Funae Y., Kawano S., lnoue K., Kamataki T., Takagi H., and Yoshizawa I. Comparison of cytochrome P-450 species which catalyze the hydroxylations of the aromatic ring of estradiol and estradiol 17-sulfate. J. Steroid Biochem. Mol. Biol. 38 (1991) 737-743
149. Waxman D., Ko A., and Walsh C. Regioselectivity and stereospecificity of androgen hydroxylations catalyzed by cytochrome P450 isozymes purified from phenobarbital-induced rat liver. J. Biol. Chem. 258 (1983) 11937-11947
150. Waxman D.J. Rat hepatic cytochrome P-450 isoenzyme 2c. Identification as a male-specific, developmentally induced steroid 16 alpha-hydroxylase and comparison to a female-specific cytochrome P450 isoenzyme. J. Biol. Chem. 259 (1984) 15481-15490
151. Waxman D.J. Interactions of hepatic cytochromes P-450 with steroid hormones. Regioselectivity and stereospecificity of steroid metabolism and hormonal regulation of rat P-450 enzyme expression. Biochem. Pharmacol. 37 (1988) 71-84
152. Waxman D.J. Rat hepatic P450IIA and P450IIC subfamily expression using catalytic, immunochemical, and molecular probes. Methods Enzymol. 206 (1991) 249-267
153. Waxman D.J. Regulation of liver-specific steroid metabolizing cytochromes P450: Cholesterol 7alpha-hydroxylase, bile acid 6beta-hydroxylase, and growth hormone-responsive steroid hormone hydroxylases. J. Ster. Biochem. Molec. Biol. 43 (1992) 1055-1072
154. Waxman, D.J. (1996). Role of metabolism in the activation of dehyroepiandrosterone as a peroxisome proliferator. J. Endocrinol, (in press).
155. Waxman D.J., Attisano C., Guengerich F.P., and Lapenson D.P. Human liver microsomal steroid metabolism: Identification of the major microsomal steroid hormone 6 beta-hydroxylase cytochrome P-450 enzyme. Arch. Biochem. Biophys. 263 (1988) 424-436
156. Waxman D.J., and Azaroff L. Phenobarbital induction of cytochrome P-450 gene expression. Biochem. J. 281 (1992) 577-592
157. Waxman D.J., Dannan G.A., and Guengerich F.P. Regulation of rat hepatic cytochrome P-450: Age-dependent expression, hormonal imprinting, and xenobiotic inducibility of sex-specific isoenzymes. Biochemistry 24 (1985) 4409-4417
158. Waxman D.J., Lapenson D.P., Nagata K., and Conlon H.D. Participation of two structurally related enzymes in rat hepatic microsomal androstenedione 7 alpha-hydroxylation. Biochem. J. 265 (1990) 187-194
159. Waxman D.J., Lapenson D.P., Aoyama T., Gelboin H.V., Gonzalez F.J., and Korzekwa K. Steroid hormone hydroxylase specificities of eleven cDNA-expressed human cytochrome P450s. Arch. Biochem. Biophys. 290 (1991) 160-166
160. Waxman D.J., LeBlanc G.A., Morrissey J.J., Staunton J., and Lapenson D.P. Adult malespecific and neonatally programmed rat hepatic P-450 forms RLM2 and 2a are not dependent on pulsatile plasma growth hormone for expression. J. Biol. Chem. 263 (1988) 11396-11406
161. Waxman D.J., Morrissey J.J., and LeBlanc G.A. Female-predominant rat hepatic P-450 forms j (IIE1) and 3 (IIA1) are under hormonal regulatory controls distinct from those of the sex-specific P-450 forms. Endocrinology 124 (1989) 2954-2966
162. Waxman D.J., Morrissey J.J., and LeBlanc G.A. Hypophysectomy differentially alters P-450 protein levels and enzyme activities in rat liver: Pituitary control of hepatic NADPH cytochrome P-450 reductase. Mol. Pharmacol. 35 (1989) 519-525
163. Waxman D.J., Pampori N.A., Ram P.A., Agrawal A.K., and Shapiro B.H. Interpulse interval in circulating growth hormone patterns regulates sexually dimorphic expression of hepatic cytochrome P450. Proc. Natl. Acad. Sci. USA 88 (1991) 6868-6872
164. Waxman D.J., Ram P.A., Notani G., LeBlanc G.A., Alberta J.A., Morrissey J.J., and Sundseth S.S. Pituitary regulation of the male-specific steroid 6 beta-hydroxylase P-450 2a (gene product IIIA2) in adult rat liver Suppressive influence of growth hormone and thyroxine acting at a pretranslational level. Mol. Endocrinol. 4 (1990) 447-454
165. Waxman D.J., Ram P.A., Pampori N.A., and Shapiro B.H. Growth hormone regulation of male-specific rat liver P450s 2A2 and 3A2: induction by intermittent growth hormone pulses in male but not female rats rendered growth hormone deficient by neonatal monosodium glutamate. Mol. Pharmacol. 48 (1995) 790-797
166. Waxman D.J., Ram P.A., Park S.H., and Choi H.K. Intermittent plasma growth hormone triggers tyrosine phosphorylation and nuclear translocation of a liver-expressed, Stat 5-related DNA binding protein Proposed role as an intracellular regulator of male-specific liver gene transcription. J. Biol. Chem. 270 (1995) 13262-13270
167. Westin S., Tollet P., Strom A., Mode A., and Gustafsson J.A. The role and mechanism of growth hormone in the regulation of sexually dimorphic P450 enzymes in rat liver. J. Steroid. Biochem. Molec. Biol. 43 (1992) 1045-1053
168. Wood A.W., Ryan D.E., Thomas P.E., and Levin W. Regio- and stereoselective metabolism of two C19 steroids by five highly purified and reconstituted rat hepatic cytochrome P-450 isozymes. J. Biol. Chem. 258 (1983) 8839-8847
169. Wright K., and Morgan E.T. Transcriptional and post-transcriptional suppression of P450IIC11 and P450IIC12 by inflammation. FEBS Lett. 271 (1990) 59-61
170. Wrighton S.A., Brian W.R., Sari M.A., Iwasaki M., Guengerich F.P., Raucy J.L., Molowa D.T., and Vandenbranden M. Studies on the expression and metabolic capabilities of human liver cytochrome P450IIIA5 (HLp3). Mol. Pharmacol. 38 (1990) 207-213
171. Wu H.Q., Masset B.J., Tweedie D.J., Milewich L., Frenkel R.A., Martin W.C., Estabrook R.W., and Prough R.A. Induction of microsomal NADPH-cytochrome P-450 reductase and cytochrome P-450IVA1 (P-450LA omega) by dehydroepiandrosterone in rats: A possible peroxisomal proliferator. Cancer Res. 49 (1989) 2337-2343
172. Yamada J., Sakuma M., Ikeda T., Fukuda K., and Suga T. Characteristics of dehydroepiandrosterone as a peroxisome proliferator. Biochim. Biophys. Acta. 1092 (1991) 233-243
173. Yamazoe Y., Ling X., Murayama N., Gong D., Nagata K., and Kato R. Modulation of hepatic level of microsomal testosterone 7 alpha-hydroxylase, P-450a (P450IIA), by thyroid hormone and growth hormone in rat liver. J. Biochem. (Tokyo) 108 (1990) 599-603
174. Yamazoe Y., Murayama N., Shimada M., Yamauchi K., Nagata K., Imaoka S., Funae Y., and Kato R. A sex-specific form of cytochrome P-450 catalyzing propoxycoumarin O-depropylation and its identity with testosterone 6 beta-hydroxylase in untreated rat livers: reconstitution of the activity with microsomal lipids. J. Biochem. (Tokyo) 104 (1988) 785-790
175. Yamazoe Y., Shimada M., Murayama N., and Kato R. Suppression of levels of phenobarbitalinducible rat liver cytochrome P-450 by pituitary hormone. J. Biol. Chem. 262 (1987) 7423-7428
176. Zaphiropoulos P.G., Mode A., Norstedt G., and Gustafsson J.A. Regulation of sexual differentiation in drug and steroid metabolism. Trends Pharmacol. Sci. 10 (1989) 149-153
177. Zaphiropoulos P.G., Strom A., Robertson J.A., and Gustafsson J.A. Structural and regulatory analysis of the male-specific rat liver cytochrome P-450 g: Repression by continuous growth hormone administration. Mol. Endocrinol. 4 (1990) 53-58
178. Zhang B., Marcus S.L., Sajjadi F.G., Alvares K., Reddy J.K., Subramani S., Rachubinski R.A., and Capone J.P. 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 (1992) 7541-7545
179. Zhao S., and Waxman D.J. Interaction of sex- and growth hormone (GH)-dependent liver nuclear factors with CYP2C12 promoter. FASEB J. 8 (1994) A1250
180. Zimniak P., and Waxman D.J. Liver cytochrome P450 metabolism of endogenous steroid hormones, bile acids, and fatty acids. In: Schenkman J.B., and Greim H. (Eds). Handbook of Experimental Pharmacology 105 (1993), Springer-Verlag, Berlin 123-144 105 Cytochrome P450