Cytostatic and antiestrogenic effects of 2-(indol-3-ylmethyl)-3,3'-diindolylmethane, a major in vivo product of dietary indole-3-carbinol

Biochemical Pharmacology

Volumn 58, Issue 5, 1999, Pages 825-834

  Chang, Yu Chen ^a   Riby, Jacques ^a   Chang, Grace H F ^a   Peng, Baocheng ^a   Firestone, Gary ^b   Bjeldanes, Leonard F ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

2 (indol 3 ylmethyl) 3; 3' diindolylmethane; Antiestrogenic; Breast tumor cells; Cytostatic; HPLC; Indole 3 carbinol

Indexed keywords

2 (INDOL 3 YLMETHYL) 3,3' DIINDOLYLMETHANE; 3 INDOLEMETHANOL; ANTIESTROGEN; AROMATIC HYDROCARBON RECEPTOR; ESTRADIOL; ESTROGEN; ESTROGEN RECEPTOR; ETHOXYRESORUFIN DEETHYLASE; MESSENGER RNA; OLIGOMER; TAMOXIFEN; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST TUMOR; CANCER CELL; CELL PROLIFERATION; CELL STRAIN MCF 7; CONTROLLED STUDY; DRUG RECEPTOR BINDING; FEMALE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; PRIORITY JOURNAL;

ANTICARCINOGENIC AGENTS; ANTINEOPLASTIC AGENTS; BINDING, COMPETITIVE; CELL DIVISION; DIET; ESTROGEN ANTAGONISTS; HUMANS; INDOLES; RECEPTORS, ARYL HYDROCARBON; RECEPTORS, ESTROGEN; SIGNAL TRANSDUCTION; TUMOR CELLS, CULTURED;

EID: 0032777422     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-2952(99)00165-3     Document Type: Article

References (24)

1. Wattenberg L.W., Loub W.D. Inhibition of polycyclic aromatic hydrocarbon-induced neoplasia by naturally occurring indoles. Cancer Res. 38:1978;1410-1415.
2. 1 carcinogenesis in rainbow trout by flavone and indole compounds. Carcinogenesis. 5:1984;615-619.
3. Tanaka T., Kojima T., Morishita Y., Mori H. Inhibitory effects of the natural products indole-3-carbinol and sinigrin during initiation and promotion phases of 4-nitroquinoline 1-oxide-induced rat tongue carcinogenesis. Jpn J Cancer Res. 83:1992;835-842.
4. Morse M.A., LaGreca S.D., Amin S.G., Chung F.L. Effects of indole-3-carbinol on lung tumorigenesis and DNA methylation induced by 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) and on the metabolism and disposition of NNK in A/J mice. Cancer Res. 50:1990;2613-2617.
5. 1 activation. Biochem Pharmacol. 39:1990;19-26.
6. Pence B., Buddingh H., Yang S. Multiple dietary factors in the enhancement of dimethylhydrazine carcinogenesis Main effect of indole-3-carbinol . J Natl Cancer Inst. 77:1986;269-276.
7. Bailey G.S., Hendricks J.D., Shelton K.W., Nixon J.E., Pawlowski N.E. Enhancement of carcinogenesis by the natural anticarcinogen indole-3-carbinol. J Natl Cancer Inst. 78:1987;931-936.
8. Kim D., Han B., Ahn B., Hasegawa R., Shirai T., Ito N., Tsuda H. Enhancement by indole-3-carbinol of liver and thyroid gland neoplastic development in a rat medium-term multiorgan carcinogenesis model. Carcinogenesis. 18:1997;377-381.
9. Schmidt J.V., Bradfield C.A. Ah receptor signaling pathways. Annu Rev Cell Dev Biol. 12:1996;55-89.
10. Grubbs C.J., Steele V.E., Casebolt T., Juliana M.M., Eto I., Whitaker L.M., Dragnev K.H., Kelloff G.J., Lubet R.L. Chemoprevention of chemically-induced mammary carcinogenesis by indole-3-carbinol. Anticancer Res. 15:1995;709-716.
11. Bradlow H.L., Michnovicz J.J., Telang N.T., Osborne M.P. Effects of dietary indole-3-carbinol on estradiol metabolism and spontaneous mammary tumors in mice. Carcinogenesis. 12:1991;1571-1574.
12. Kojima T., Tanaka T., Mori H. Chemoprevention of spontaneous endometrial cancer in female Donryu rats by dietary indole-3-carbinol. Cancer Res. 54:1994;1446-1449.
13. Grose K.R., Bjeldanes L.F. Oligomerization of indole-3-carbinol in aqueous acid. Chem Res Toxicol. 5:1992;188-193.
14. Stresser D.M., Williams D.E., Griffin D.A., Bailey G.S. Mechanisms of tumor modulation by indole-3-carbinol. Disposition and excretion in male Fischer 344 rats. Drug Metab Dispos. 23:1995;965-975.
15. Chen Y.-H., Riby J., Srivastava P., Bartholomew J., Denison M., Bjeldanes L. Regulation of CYP1A1 by indolo[3,2-b]carbazole in murine hepatoma cells. J Biol Chem. 270:1995;22548-22555.
16. Chen I., Safe S., Bjeldanes L. Indole-3-carbinol and diindolymethane as aryl hydrocarbon (Ah) receptor agonists and antagonists in T47D human breast cancer cells. Biochem Pharmacol. 51:1996;1069-1076.
17. Stresser D.M., Bjeldanes L.F., Bailey G.S., Williams D.E. The anticarcinogen 3,3′-diindolylmethane is an inhibitor of cytochrome P-450. J Biochem Toxicol. 10:1995;191-201.
18. Chen I., McDougal A., Wang F., Safe S. Aryl hydrocarbon receptor-mediated antiestrogenic and antitumorigenic activity of diindolylmethane. Carcinogenesis. 19:1998;1631-1639.
19. Santell R.C., Chang Y.C., Nair M.G., Helferich W.G. Dietary genistein exerts estrogenic effects upon the uterus, mammary gland and the hypothalamic/pituitary axis in rats. J Nutr. 127:1997;263-269.
20. Chang T.-C., Nardulli A.M., Lew D., Shapiro D.J. The role of estrogen response elements in expression of the Xenopus laevis vitellogenin B1 gene. Mol Endocrinol. 6:1992;346-354.
21. Seed B., Sheen J.Y. A simple phase-extraction assay for chloramphenicol acyltransferase activity. Gene. 67:1988;271-277.
22. Dohr O., Vogel D., Abel J. Different response of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD)-sensitive genes in human breast cancer MCF-7 and MDA-MB-231 cells. Arch Biochem Biophys. 321:1995;405-412.
23. Bjeldanes L., Kim J.Y., Grose K.R., Bartholomew J.C., Bradfield C.A. Aromatic hydrocarbon responsiveness-receptor agonists generated from indole-3-carbinol in vitro and in vivo Comparisons with TCDD . Proc Natl Acad Sci USA. 88:1991;9543-9547.
24. De Kruif C.A., Marsman J.W., Venekamp J.C., Falke H.E., Noordhoek J., Blaauboer B.J., Wortelboer H.M. Structure elucidation of acid reaction products of indole-3-carbinol Detection in vivo and enzyme induction in vitro . Chem Biol Interact. 80:1991;303-315.