Multifunctional aspects of the action of indole-3-carbinol as an antitumor agent

Annals of the New York Academy of Sciences

Volumn 889, Issue , 1999, Pages 204-213

  Bradlow, H Leon ^a,b   Sepkovic, Daniel W ^a   Telang, Nitin T ^a   Osborne, Michael P ^a  

^a Strang Cancer Research Laboratory   (United States)

^b ROCKEFELLER UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

16ALPHA HYDROXYESTRONE; 2 HYDROXYESTRONE; 3 INDOLEMETHANOL; 4 HYDROXYESTRONE; ANTINEOPLASTIC AGENT; CARCINOGEN; CYCLIN D; CYTOCHROME P450 ISOENZYME; DRUG METABOLITE; ESTROGEN; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; BREAST CANCER; CANCER PREVENTION; CELL CYCLE; CONFERENCE PAPER; CONTROLLED STUDY; DRUG HYDROXYLATION; ESTROGEN METABOLISM; NONHUMAN;

ANIMALIA;

EID: 0033427186     PISSN: 00778923     EISSN: None     Source Type: Book Series    
DOI: 10.1111/j.1749-6632.1999.tb08736.x     Document Type: Conference Paper

References (55)

1. 1. Schneider, J., D. Kinne, A. Fracchia, V. Pierce, K.E. Anderson, H.L. Bradlow & J. Fishman. 1982. Abnormal oxidative metabolism of estradiol in women with breast cancer. Proc. Natl. Acad. Sci. USA 79(9): 3047-3051.
2. 2. Bradlow, H.L., R.J. Hershcopf, C.P. Martucci & J. Fishman. 1985. Estradiol 16α-hydroxylation in the mouse correlates with mammary tumor incidence and presence of murine mammary tumor virus: A possible model for the hormonal etiology of breast cancer in humans. Proc. Natl. Acad. Sci. USA 82: 6295-6299.
3. 3. Telang, N.T., R. Narayanen, H.L. Bradlow & M.P. Osborne. 1991. Coordinated expression of intermediate biomarkers for tumorigenic transformation in Ras-transfected mouse mammary epithelial cells. Breast Cancer Res. Treat. 18: 155-163.
4. 4. Telang, N.T., H.L. Bradlow, H. Kurihara & M.P. Osborne. 1989. In vitro biotransformation of estradiol by explant cultures of murine mammary tissues. Breast Cancer Res. Treat. 13: 173-181.
5. 5. Bradlow, H.L., D. Davis, D.W. Sepkovic, R. Tiwari & M.P. Osborne. 1998. Role of the estrogen receptor in the action of organochlorine pesticides on estrogen metabolism in human breast cancer cell lines. Sci. Total Environ. 202: 9-14.
6. 6. Telang, N.T., A. Suto, G.Y. Wong, M.P. Osborne & H.L. Bradlow. 1992. Estrogen metabolite 16α-hydroxyestrone induces genotoxic damage and aberrant cell proliferation in mouse mammary epithelial cells in culture. J. Natl. Cancer Inst. 84: 634-638.
7. 7. Liehr, J.G. & M.J. Ricci. 1996. 4-Hydroxylation of estrogens as marker of human mammary tumors. Proc. Natl. Acad. Sci. USA 93: 3294-3296.
8. 8. Dwivedy, I., P. Devanesan, P. Cremonesi, E. Rogan & E. Cavalierl. 1992. Synthesis and characterization of estrogen 2,3-and 3,4-quinones. Comparison of DNA adducts formed by the quinones versus horseradish peroxidase-activated catechol estrogens. Chem. Res. Toxicol. 5: 828-833.
9. 9. Suto, A., H.L. Bradlow, T. Kubota, M. Kitajima, G.Y. Wong, M.P. Osborne & N.T. Telang. 1993. Alteration in proliferative and endocrine responsiveness of human mammary carcinoma cells by prototypic tumor-suppressing agents. Steroids 58: 215-219.
10. 10. Osborne, M.P., R.A. Karmali, R.J. Hershcopf, H.L. Bradlow, I.A. Kourides, W.R. Williams, P.P. Rosen & J. Fishman. 1988. Omega-3 fatty acids: Modulation of estrogen metabolism and potential for breast cancer prevention. Cancer Invest. 8: 629-631.
11. 11. Kappas, A., K.E. Anderson, A.H. Conney, E.J. Pantuck, J. Fishman & H.L. Bradlow. 1983. Nutrition-endocrine interactions: Induction of reciprocal changes in the D4-5a-reduction of testosterone and the cytochrome P-450-dependent oxidation of estradiol by dietary macronutrienls in man. Proc. Natl. Acad. Sci. USA 80: 7646-7649.
12. 12. Anderson, K.E., A. Kappas, A.H. Conney, H.L. Bradlow & J. Fishman. 1984. The influence of dietary protein and carbohydrate on the principal oxidative biotransformations of estradiol in normal subjects. J. Clin. Endocrinol. Metab. 59: 103-107.
13. 13. Michnovicz, J.J., H. Naganuma, R.J. Hershcopf, H.L. Bradlow & J. Fishman. 1988. Increased urinary catechol estrogen excretion in female smokers. Steroids 52: 69-83.
14. 14. Gierthy, J.F., D.W. Lincoln II, S.J. Kampcik, H.W. Dickerman, H.L. Bradlow, T. Niwa & G.E. Swaneck. 1988. Induction of human breast cancer cells by 2,3,7,8-tetrachlorodibenzo-P-dioxin. Biochem. Biophys. Res. Commun. 157: 50-55.
15. 15. McDanell, R., A.E. McLean, A.B. Hanley, R.K. Heaney & G.R. Fenwick. 1987. Differential induction of mixed-function oxidase (MFO) activity in rat liver and intestine by diets containing processed cabbage: Correlation with cabbage levels of glucosinolates and glucosinolate hydrolysis products. Food Chem. Toxicol. 25: 363-368.
16. 16. Bradfield, C.A. & L.F. Bjeldanes. 1987. Structure-activity relationships of dietary indoles: A proposed mechanism of action as modifiers of xenobiotic metabolism. J. Toxicol. Environ. Health 21: 311-323.
17. 17. Bjeldanes, L.F., J.Y. Kim, K.R. Grose, J.C. Bartholomew & C.A. Bradfield. 1991. Aromatic hydrocarbon responsiveness-receptor agonists generated from indole-3-carbinol in vitro and in vivo: Comparisons with 2,3,7,8-tetrachlorodibenzo-p-dioxin. Proc. Natl. Acad. Sci. USA 88: 9543-9547.
18. 18. Jellinck, P.H., P.G. Forkert, D.S. Riddick, A.B. Okey, J.J. Michnovicz & H.L. Bradlow. 1993. Ah receptor binding properties of indole carbinols and induction of hepatic estradiol hydroxylation. Biochem. Pharmacol. 45: 1129-1136.
19. 19. Niwa, T., G. Swaneck & H.L. Bradlow. 1994. Alterations in estradiol metabolism in MCF-7 cells induced by treatment with indole-3-carbinol and related compounds. Steroids 59: 523-527.
20. 20. Tiwari, R.K., H.L. Bradlow, N.T. Telang & M.P. Osborne. 1994. Selective responses of human breast cancer cells to indole-3-carbinol, a chemopreventive agent. J. Natl. Cancer Inst. 86: 126-131.
21. 21. Cover, C.M., S.J. Hsieh, S.H. Trans, G. Hallden, G.S. Kim, L.F. Bjeldanes & G.L. Firestone. 1998. Indole-3-carbinol inhibits the expression of cyclin-dependent kinase-6 and induces a G1 cell cycle arrest of human breast cancer cells independent of estrogen receptor signalling. J. Biol. Chem. 273: 2828-2847.
22. 22. Telang, N.T., M. Katdare, H.L. Bradlow, M.P. Osborne & J. Fishman. 1997. Inhibition of proliferation and modulation of estradiol metabolism: Novel mechanisms for breast cancer prevention by the phytochemical indole-3-carbinol. Proc. Soc. Exp. Biol. Med. 216: 246-252.
23. 23. Yuan, F., D.Z. Chen, K. Liu, D.W. Sepkovic, H.L. Bradlow & K. Auborn. 1999. Anti-estrogenic activities of indole-3-carbinol in cervical cells: Implication for prevention of cervical cancer. Anticancer Res. 19 (3A): 1673-1680.
24. 24. Seeger, H., A.O. Mueck & T.H. Lippert. 1997. Effect of estradiol metabolites on the susceptibility of low density lipoprotein to oxidation. Life Sci. 61: 865-868.
25. 25. Seeger, H., A.O. Mueck & T.H. Lippert. 1998. The antiproliferative effect of 17β-estradiol metabolites on human cronary artery smooth muscle cells. Med. Sci. Res. 26: 481-482.
26. 26. Michnovicz, J.J. & H.L. Bradlow. 1990. Induction of estradiol metabolism by dietary indole-3-carbinol in humans. J. Natl. Cancer Inst. 50: 947-950.
27. 27. Bradlow, H.L., J.J. Michnovicz, G.Y.C. Wong, M.P. Halper, D. Miller & M.P. Osborne. 1994. Long term responses of women to indole-3-carbinol or a high fiber diet. Cancer Epidemiol. Biomarkers Prev. 3: 591-595.
28. 28. Wong, G.Y.C., H.L. Bradlow, D.W. Sepkovic, S. Mehl, J. Mailman & M.P. Osborne. 1998. A dose-ranging study of indole-3-carbinol for breast cancer prevention J. Cell Biol. 28: 111-116.
29. 29. Suto, A., H.L. Bradlow, T. Kubota, M. Kitajima, G.Y. Wong, M.P. Osborne & N.T. Telang. 1993. Alteration in proliferative and endocrine responsiveness of human mammary carcinoma cells by prototypic tumor-suppressing agents. Steroids 58: 215-219.
30. 30. Bradlow, H.L., R.J. Hershcopf, C.P. Martucci & J. Fishman. 1995. Estradiol 16α-hydroxylation in the mouse correlates with mammary tumor incidence and presence of murine mammary tumor virus: A possible model for the hormonal etiology of breast cancer in humans. Proc. Natl. Acad. Sci. USA 82: 6295-6299.
31. 31. Malloy, V.L., H.L. Bradlow & N. Orentreich. 1998. Interaction between a semi-synthetic diet and indole-3-carbinol on mammary tumor incidence in Balb-C3H mice. Anticancer Res. 17: 4333-4338.
32. 32. Grubbs, C.J., V.E. Steele, T. Casebolt, M.M. Juliana, I. Eto, L.M. Whitaker, K.H. Dragnev, G.J. Kelloff & R.L. Lubet. 1995. Chemoprevention of chemically-induced mammary carcinogenesis by indole-3-carbinol. Anticancer Res. 15: 709-716.
33. 33. Newfield, L., H.L. Bradlow, D.W. Sepkovic & K. Auborn. 1998. Estrogen metabolism and the malignant potential of human papillomavirus immortalized keratinocytes. Proc. Soc. Exp. Biol. Med. 217: 322-326.
34. 34. Newfield, L., A. Goldsmith, H.L. Bradlow & K. Auborn. 1993. Estrogen metabolism and human papillomavirus-induced tumors of the larynx: Chemoprophylaxis with indole-3-carbinol. Anticancer Res. 13: 337-342.
35. 35. Rosen, C.A., J.W. Thompson, G.E. Woodson, A.P. Hengesteg & H.L. Bradlow. 1998. Preliminary results of the use of indole-3-carbinol for recurrent respiratory apillomalosis. Otolaryngol. Head Neck Surg. 118: 810-815.
36. 36. Kojima, T., T. Tanaka & H. Mori. 1994. Chemprevention of spontaneous endometrial cancer in female Donryu rats by dietary indole-3-carbinol. Cancer Res. 54: 1446-1449.
37. 37. Stoner, G.D., G. Adam-Rodwell & M.A. Morse. 1993. Lung tumors in strain A mice: Application for studies in cancer chemprevention. J. Cell. Biochem. Suppl. 17F: 95-103.
38. 38. Chung, F-L., M.A. Morse, K.I. Eklind & Y. Xu. 1993. Inhibition of tobacco-specific nitrosamine-induced lung tumorigenesis by compounds derived from cruciferous vegetables and green tea. Ann. N.Y. Acad. Sci. 686: 186-202.
39. 39. Morse, M.A., S.D. LaGreca, S.C. Amin & F.L. Chung. 1990. 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: 2613-2617.
40. 40. El-Bayoumy, K., P. Upadhyaya, D.H. Desai, S. Amin, D. Hoffman & E.L. Wynder. 1996. Effects of 1,4-phenylenebis(methylene)selenocyanate, phenethyliso-thiocyanate, indole-3-carbinol, and D-limonene individually and in combination on the tumorigenicity of the tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in A/J mouse lung. Anticancer Res. 16: 2709-2712.
41. 41. Taioli, E., S. Garbers, H.L. Bradlow, S.G. Carmella, S. Akerbar & S.S. Hecht. 1997. Effects of indole-3-carbinol on the metabolism of 4-(methylnitroso-amino)-1-(3-pyridyl)-1-butanone (NNK) in smokers. Cancer Epidemiol. Biomarkers Prev. 6: 517-522.
42. 42. Tanaka, T., T. Kojima, Y. Morishita & H. Mori. 1992. 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: 835-842.
43. 43. Gamet-Payrastre, L., S. Lumeau, N. Gasc, G. Cassar, P. Rollin & J. Tuliez. 1998. Selective cytostatic and cytotoxic effects of glucosinolate hydrolysis products on human colon cancer cells in vitro. Anticancer Drugs 9: 141-148.
44. 44. Tanaka, T., Y. Mori, Y. Morishita, A. Hara, T. Ohno, T. Kojima & H. Mori. 1990. Inhibitory effect of sinigrin and indole-3-carbinol on diethylnitroamine-induced hepatocarcinogenesis in male ACI/N rats. Carcinogenesis 11: 1403-1406.
45. 45. Bailey, G.S., R.H. Dashwood, A.T. Fong, D.E. Williams, R.A. Scanlan & J.D. Hendricks. 1991. Modulation of mycotoxin and nitrosamine carcinogenesis by indole-3-carbinol: Quantitative analysis of inhibition versus promotion. In Relevance to Human Cancer of N-Nitroso Compounds. I.K. O'Neill, J. Chen & H. Bartsch, Eds.: 275-280. International Agency for Research on Cancer. Lyon.
46. 46. Bailey, G.S., J.D. Hendricks, D.W. Shelton, J.E. Nixon & N. Pawlowshi. 1987. Enhancement of carcinogenesis by the natural anti-carcinogen indole-3-carbinol. J. Natl. Cancer Inst. 78: 931-934.
47. 1 induced carcinogenesis by indole-3-carbinol in rat liver - Predicting the outcome using early biomarkers. Carcinogenesis. In press.
48. 48. Organesian, A., J.D. Hendricks & D.E. Williams. 1997. Long term dietary indole-3-carbinol inhibits diethylnitrosamine-initiated hepatocarcinogenesis in the infant mouse model. Cancer Lett. 118: 87-94.
49. 49. Kim, D.J., K.K. Lee, B.S. Han, B. Ahn, J.H. Bae & J.J. Jang. 1994. Biphasic modifying effect of indole-3-carbinol on diethylnitrosamine-induced preneoplastic glutathione S-transferase placental form-positive liver cell foci in sprague-Dawley rats. Jpn. J. Cancer Res. 86: 578-583.
50. 50. Williams, G.M., M.J. Iatropoulos, C.X. Wang, N. Ali, A. Rivenson, L.A. Peterson, C. Schulz & R. Gebhardt. 1996. Diethylnitrosamine exposure-responses for DNA damage, centrilobular cytotoxicity, cell proliferation and carcinogenesis in rat liver exhibit some non-linearities. Carcinogenesis 17: 2253-2258.
51. 51. Hudson, E.A., R.J.L. Munks, L. Hoowells, H.W.L. Ball, P. Pamar & M.M. Manson. 1998. Mechanism of action of indole-3-carbinol as a chemo-preventive agent. Abstr. 1965 AACR meeting.
52. 52. Baldwin, W.S. & G.A. LeBlanc. 1992. The anti-carcinogenic plant compound indole-3-carbinol differentially modulates P-450 mediated steroid hydroxylase activities in mice. Chem. Biol. Interact. 83: 155-169.
53. 53. Stresser, D.M., D.E. Williams & G.S. Bailey. 1991. Diindolylmethane (I33′), the linear dimer of indole-3-carbinol (I3C) is a potent inhibitor of P450 [A] in trout. Toxicologist 11: 1309.
54. 54. Wortelboer, H.M., C.A. de Kruif, A.A. van Iersel, H.E. Falke, J. Noordhoek & B.J. Blauboer. 1992. Acid reaction products of indole-3-carbinol and their effects on cytochrome P450 and phase II enzymes in rat and monkey hepatocytes. Biochem. Pharmacol. 43: 1439-444.
55. 55. Cover, C.M., S.J. Hsieh, E.J. Cram, C. Hong, J.E. Riby, L.F. Bjeldanes & G.L. Firestone. 1999. Indole-3-carbinol and tamoxifen cooperate to arrest the cell cycle of MCF-7 human breast cancer cells. Cancer Res. 59: 1244-1251.