Induction of estradiol-2-hydroxylase and ethoxyresorufin-O-deethylase by 3-substituted indole compounds

European Journal of Pharmacology

Volumn 362, Issue 1, 1998, Pages 87-93

  Wong, Dobe C C ^a   Fong, Wing Ping ^a   Lee, Susanna S T ^a   Kong, Yun Cheung ^a   Cheng, Kin Fai ^b   Stone, Grant ^c  

^a CHINESE UNIVERSITY OF HONG KONG   (Hong Kong)

^b UNIVERSITY OF HONG KONG   (Hong Kong)

^c UNIVERSITY OF SYDNEY   (Australia)

Author keywords

Anti estrogenic activity; Aryl hydrocarbon receptor; Estradiol 2 hydroxylase; Ethoxyresorufin O deethylase; Yuehchukene

Indexed keywords

ANTIESTROGEN; AROMATIC HYDROCARBON RECEPTOR; CYTOCHROME P450; ESTRADIOL; ESTRADIOL 2 HYDROXYLASE; ETHOXYRESORUFIN DEETHYLASE; INDOLE DERIVATIVE; UNCLASSIFIED DRUG; YUEHCHUKENE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BREAST CANCER; CONTROLLED STUDY; DRUG MECHANISM; ENZYME ACTIVITY; FEMALE; LIVER; MOUSE; NONHUMAN; ORAL DRUG ADMINISTRATION; PRIORITY JOURNAL; SUBCUTANEOUS DRUG ADMINISTRATION;

ALKALOIDS; ANIMALS; CONTRACEPTIVES, POSTCOITAL; CYTOCHROME P-450 CYP1A1; CYTOCHROME P-450 ENZYME SYSTEM; ENZYME INDUCTION; ESTROGEN ANTAGONISTS; FEMALE; INDOLES; MICE; MICE, INBRED BALB C; RECEPTORS, ARYL HYDROCARBON; STEROID HYDROXYLASES;

EID: 0032437078     PISSN: 00142999     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0014-2999(98)00742-0     Document Type: Article

References (28)

1. Adlercreutz, H., Bannwart, C., Wahala, K., Makela, T., Brunow, G., Hase, T., Arosemena, P.J., Kellis, J.T. Jr., Vickery, L.E., 1993. Inhibition of human aromatase by mammalian lignans and isoflavonoid phytoestrogens. J. Steroid Biochem. Mol. Biol. 44, 147-153.
2. Aoyama, T., Korzekwa, K., Nagata, K., Gillette, J., Gelboin, H.V., Gonzalez, F.J., 1990. Estradiol metabolism by complementary deoxyribonucleic acid-expressed human cytochrome P450s. Endocrinology 126, 3101-3106.
3. Ball, S.E., Forrester, L.M., Wolf, C.R., Back, D.J., 1990. Differences in the cytochrome P-450 isoenzymes involved in the 2-hydroxylation of oestradiol and 17α-ethinyloestradiol. Biochem. J. 267, 221-226.
4. Bradford, M.M., 1976. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72, 248-255.
5. Bradlow, H.L., Sepkovic, D.W., Telang, N.T., Osborne, M.P., 1995. Indole-3-carbinol, a novel approach to breast cancer prevention. Ann. N.Y. Acad. Sci. 768, 180-200.
6. Bradlow, H.L., Telang, N.T., Sepkovic, D.W., Osborne, M.P., 1996. 2-Hydroxyestrone: the 'good' estrogen. J. Endocrinol. 150, S259-S265.
7. Cheng, K.F., Kong, Y.C., Chan, T.Y., 1985. Biomimetic synthesis of yuehchukene. J. Chem. Soc., Chem. Commun. 1, 48-49.
8. Davis, D.L., Axelrod, D., Osborne, M.P., Telang, N.T., 1997. Environment influence on breast cancer risk. Sci. Med. 4, 56-63.
9. Fernandez-Salguero, P., Pineau, T., Hilbert, D.M., McPhail, T., Lee, S.S.T., Kimura, S., Nebert, D.W., Rudikoff, S., Ward, J.M., Gonzalez, F.J., 1995. Immune system impairment and hepatic fibrosis in mice lacking the dioxin-binding Ah receptor. Science 268, 722-726.
10. Fishman, J., Bradlow, H.L., Schneider, J., Anderson, K.E., Kappas, A., 1980. Radiometrie analysis of biological oxidations in man: sex differences in estradiol metabolism. Proc. Natl. Acad. Sci. USA 77, 4957-4960.
11. Gradishar, W.J., Jordon, V.C., 1997. Clinical potential of new antiestrogens. J. Clin. Oncol. 15, 840-852.
12. Hayes, C.L., Spink, D.C., Spink, B.C., Cao, J.Q., Walker, N.J., Sutter, T.R., 1996. 17β-Estradiol hydroxylation catalyzed by human cytochrome P450 1B1. Proc. Natl. Acad. Sci. USA 93, 9776-9781.
13. Hong, W.K., Sporn, M.B., 1997. Recent advances in chemoprevention of cancer. Science 278, 1073-1077.
14. Howarth, N.M., Purohit, A., Reed, M.J., Potter, B.V.L., 1994. Estrone sulfamates: potent inhibitors of estrone sulfatase with therapeutic potential. J. Med. Chem. 37, 219-221.
15. Jellinck, P.H., Forkert, P.G., Riddick, D.S., Okey, A.B., Michnovicz, J.J., Bradlow, H.L., 1993. Ah receptor binding properties of indole carbinols and induction of hepatic estradiol hydroxylation. Biochem. Pharmacol. 45, 1129-1136.
16. Kerlan, V., Dreano, Y., Bercovici, J.P., Beaune, P.H., Floch, H.H., Berthou, F., 1992. Nature of cytochromes P450 involved in the 2-/4-hydroxylations of estradiol in human liver microsomes. Biochem. Pharmacol. 44, 1745-1756.
17. Lee, V., Cheung, M.K., Wong, W.T., Cheng, K.F., 1996. Studies on the acid-catalyzed dimerization of 2-prenylindoles. Tetrahedron 52, 9455-9468.
18. Leighton, J.K., Canning, S., Guthrie, H.D., Hammond, J.M., 1995. Expression of cytochrome P450 1A1, an estrogen hydroxylase, in ovarian granulosa cells is developmentally regulated. J. Steroid Biochem. Mol. Biol. 52, 351-356.
19. Liu, H., Wormke, M., Safe, S.H., Bjeldanes, L.F., 1994. Indolo[3,2-b] carbazole: a dietary-derived factor that exhibits both antiestrogenic and estrogenic activity. J. Natl. Cancer Inst. 86, 1758-1765.
20. Michnovicz, J.J., Bradlow, H.L., 1990. Induction of estradiol metabolism by dietary indole-3-carbinol in humans. J. Natl. Cancer Inst. 82, 947-949.
21. Ng, P.C., Ho, D.D., Ng, K.H., Kong, Y.C., Cheng, K.F., Stone, G., 1994. Mixed estrogenic and anti-estrogenic activities of yuehchukene-a bis-indole alkaloid. Eur. J. Pharmacol. 264, 1-12.
22. Osborne, C.K., Elledge, R.M., Fuqua, S.A.W., 1996. Estrogen receptors in breast cancer therapy. Sci. Med. 3, 32-41.
23. Penning, T.M., 1996. 17β-Hydroxysteroid dehydrogenase: inhibitors and inhibitor design. Endocr. Relat. Cancer 3, 41-56.
24. Pohl, R.J., Fouts, J., 1980. A rapid method for assaying the metabolism of 7-ethoxyresorufin by microsomal subcellular fractions. Anal. Biochem. 107, 150-155.
25. Riddick, D.S., Huang, Y., Harper, P.A., Okey, A.B., 1994. 2,3,7,9-Tetrachlorodibenzo-p-dioxin versus 3-methylcholanthrene: comparative studies of Ah receptor binding, transformation, and induction of CYP1A1. J. Biol. Chem. 269, 12118-12128.
26. Schneider, J., Huh, M.M., Bradlow, H.L., Fishman, J., 1984. Antiestrogen action of 2-hydroxyestrone on MCF-7 human breast cancer cells. J. Biol. Chem. 259, 4840-4845.
27. Telang, N.T., Suto, A., Wong, G.Y., Osborne, M.P., Bradlow, H.L., 1992. Induction by estrogen metabolite 16α-hydroxyestrone of genotoxic damage and aberrant proliferation in mouse mammary epithelial cells. J. Natl. Cancer Inst. 84, 634-638.
28. Tiwari, R.K., Guo, L., Bradlow, H.L., Telang, N.T., Osborne, M.P., 1994. Selective responsiveness of human breast cancer cells to indole-3-carbinol, a chemopreventive agent. J. Natl. Cancer Inst. 86, 126-131.