N-Alkoxy derivatization of indole-3-carbinol increases the efficacy of the G1 cell cycle arrest and of I3C-specific regulation of cell cycle gene transcription and activity in human breast cancer cells

Biochemical Pharmacology

Volumn 75, Issue 3, 2008, Pages 713-724

  Jump, Sarah M ^a   Kung, Jenny ^a   Staub, Richard ^a   Kinseth, Matthew A ^a   Cram, Erin J ^a   Yudina, Larisa N ^b   Preobrazhenskaya, Maria N ^b   Bjeldanes, Leonard F ^a   Firestone, Gary L ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b GAUSE INSTITUTE OF NEW ANTIBIOTICS   (Russian Federation)

Author keywords

Breast cancer cells; Cell cycle arrest; I3C; N Alkoxy constituents; Synthetic derivatives

Indexed keywords

3 ETHOXYMETHYLINDOLE; 3 INDOLEMETHANOL; 3 METHOXYMETHYLINDOLE; CYCLIN DEPENDENT KINASE 6; INDOLE DERIVATIVE; MELATONIN; N BUTOXY INDOLE 3 CARBINOL; N ETHOXY INDOLE 3 CARBINOL; N METHOXY INDOLE 3 CARBINOL; N PROPOXY INDOLE 3 CARBINOL; NITROGEN; TRYPTOPHOL; UNCLASSIFIED DRUG;

ARTICLE; BREAST CANCER; CANCER CELL; CELL CYCLE G1 PHASE; CELL GROWTH; CONTROLLED STUDY; DEHYDRATION; DRUG ACTIVITY; DRUG EFFICACY; DRUG POTENCY; ENZYME ACTIVITY; GENE EXPRESSION; GENETIC TRANSCRIPTION; HUMAN; HUMAN CELL; PRIORITY JOURNAL; RETINOBLASTOMA; STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS; BREAST NEOPLASMS; CELL LINE, TUMOR; CYCLIN-DEPENDENT KINASE 2; CYCLIN-DEPENDENT KINASE 6; FEMALE; G1 PHASE; GENE EXPRESSION REGULATION, NEOPLASTIC; HUMANS; INDOLES; PROMOTER REGIONS (GENETICS); STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 37849045485     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bcp.2007.09.024     Document Type: Article

References (41)

1. Muss H.B. Endocrine therapy for advanced breast cancer: a review. Breast Cancer Res Treat 21 (1992) 15-26
2. Pennisi E. Drug's link to genes reveals estrogen's many sides. Science 273 (1996) 1171
3. Forbes J.F. The control of breast cancer: the role of tamoxifen. Semin Oncol 24 Suppl 1 (1997) S1-5-S1-19
4. Jordan V.C. SERMs: meeting the promise of multifunctional medicines. J Natl Cancer Inst 99 (2007) 350-356
5. Birt D.F., Pelling J.C., Nair S., and Lepley D. Diet intervention for modifying cancer risk. Prog Clin Biol Res 395 (1996) 223-234
6. Lopez-Otin C., and Diamandis E.P. Breast and prostate cancer: an analysis of common epidemiological, genetic, and biochemical features. Endocr Rev 19 (1998) 365-396
7. Freudenheim J.L., Marshall J.R., Vena J.E., Laughlin R., Brasure J.R., Swanson M.K., et al. Premenopausal breast cancer risk and intake of vegetables, fruits, and related nutrients. J Natl Cancer Inst 88 (1996) 340-348
8. Wattenberg L.W., and Loub W.D. Inhibition of polycyclic aromatic hydrocarbon-induced neoplasia by naturally occurring indoles. Cancer Res 38 (1978) 1410-1413
9. Bradfield C.A., and Bjeldanes L.F. Effect of dietary indole-3-carbinol on intestinal and hepatic monooxygenase, glutathione S-transferase and epoxide hydrolase activities in the rat. Food Chem Toxicol 22 (1984) 977-982
10. Firestone G.L., and Bjeldanes L.F. Indole-3-carbinol (I3C) and 3-3′diindolylmethane (DIM) anti-proliferative signaling pathways control cell cycle gene transcription in human breast cancer cells by regulating promoter-Sp1 transcription factor interactions. J Nutr 133 (2003) 2448S-2455S
11. Aggarwal B.B., and Ichikawa H. Molecular targets and anti-cancer potential of indole-3-carbinol and its derivatives. Cell Cycle 4 (2005) 1201-1215
12. Kim Y.S., and Milner J.A. Targets for indole-3-carbinol in cancer prevention. J Nutr Biochem 16 (2005) 65-73
13. Morse M.A., LaGreca S.D., Amin S.G., and 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
14. Bradlow H.L., Sepkovic D.W., Telang N.T., and Osborne M.P. Indole-3-carbinol. A novel approach to breast cancer prevention. Ann NY Acad Sci 768 (1995) 180-200
15. Grubbs C.J., Steele V.E., Casebolt T., Juliana M.M., Eto I., Whitaker L.M., et al. Chemoprevention of chemically induced mammary carcinogenesis by indole-3-carbinol. Anticancer Res 15 (1995) 709-716
16. Bradlow H.L., Michnovicz J., Telang N.T., and Osborne M.P. Effects of dietary indole-3-carbinol on estradiol metabolism and spontaneous mammary tumors in mice. Carcinogenesis 12 (1991) 1571-1574
17. Sharma S., Stutzman J.D., Kelloff G.J., and Steele V.E. Screening of potential chemopreventive agents using biochemical markers of carcinogenesis. Cancer Res 54 (1994) 5848-5855
18. Bradfield C.A., and Bjeldanes L.F. Structure-activity relationships of dietary indoles: a proposed mechanism of action as modifiers of xenobiotic metabolism. J Toxicol Environ Health 21 (1987) 311-323
19. De Kruif C.A., Marsman J.W., Venekamp J.C., Falke H.E., Noordhoek J., Blaauboer B.J., et al. 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
20. Grose K.R., and Bjeldanes L.F. Oligomerization of indole-3-carbinol in aqueous acid. Chem Res Toxicol 5 (1992) 188-193
21. Chang Y.C., Riby J., Chang G.H., Peng B.C., Firestone G., and Bjeldanes L.F. Cytostatic and antiestrogenic effects of 2-(indol-3-ylmethyl)-3,3′-diindolylmethane, a major in vivo product of dietary indole-3-carbinol. Biochem Pharmacol 58 (1999) 825-834
22. Riby J.E., Feng C., Chang Y.C., Schaldach C.M., Firestone G.L., and Bjeldanes L.F. The major cyclic trimeric product of indole-3-carbinol is a strong agonist of the estrogen receptor-signaling pathway. Biochemistry 39 (2000) 910-918
23. Hong C., Firestone G.L., and Bjeldanes L.F. Bcl-2 family-mediated apoptotic effects of 3,3′-diindolylmethane (DIM) in human breast cancer cells. Biochem Pharmacol 63 (2002) 1085-1097
24. Chen Y.H., Riby J., Srivastava P., Bartholomew J., Denison M., and Bjeldanes L. Regulation of CYP1A1 by indolo[3,2-b]carbazole in murine hepatoma cells. J Biol Chem 270 (1995) 22548-22555
25. Bjeldanes L.F., Kim J.Y., Grose K.R., Bartholomew J.C., and Bradfield C.A. 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 (1991) 9543-9547
26. Liu H., Wormke M., Safe S.H., and Bjeldanes L.F. Indolo[3,2-b]carbazole: a dietary-derived factor that exhibits both antiestrogenic and estrogenic activity. J Natl Cancer Inst 86 (1994) 1758-1765
27. Cover C.M., Hsieh S.J., Tran S.H., Hallden G., Kim G.S., Bjeldanes L.F., et al. 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 signaling. J Biol Chem 273 (1998) 3838-3847
28. Staub R.E., Feng C., Onisko B., Bailey G.S., Firestone G.L., and Bjeldanes L.F. Fate of indole-3-carbinol in cultured human breast tumor cells. Chem Res Toxicol 15 (2002) 101-109
29. Cram E.J., Liu B.D., Bjeldanes L.F., and Firestone G.L. Indole-3-carbinol inhibits CDK6 expression in human MCF-7 breast cancer cells by disrupting Sp1 transcription factor interactions with a composite element in the CDK6 gene promoter. J Biol Chem 276 (2001) 22332-22340
30. Garcia H.H., Brar G.A., Nguyen D.H., Bjeldanes L.F., and Firestone G.L. Indole-3-carbinol (I3C) inhibits cyclin-dependent kinase-2 function in human breast cancer cells by regulating the size distribution, associated cyclin E forms, and subcellular localization of the CDK2 protein complex. J Biol Chem 280 (2005) 8756-8764
31. Gong Y., Sohn H., Xue L., Firestone G.L., and Bjeldanes L.F. 3,3′-Diindolylmethane is a novel mitochondrial H(+)-ATP synthase inhibitor that can induce p21(Cip1/Waf1) expression by induction of oxidative stress in human breast cancer cells. Cancer Res 66 (2006) 4880-4887
32. Sundar S.N., Kerekatte V., Equinozio C.N., Doan V.B., Bjeldanes L.F., and Firestone G.L. Indole-3-carbinol selectively uncouples expression and activity of estrogen receptor subtypes in human breast cancer cells. Mol Endocrinol 20 (2006) 3070-3082
33. Hong C., Kim H.A., Firestone G.L., and Bjeldanes L.F. 3,3′-Diindolylmethane (DIM) induces a G1 cell cycle arrest in human breast cancer cells that is accompanied by Sp1-mediated activation of p21(WAF1/CIP1) expression. Carcinogenesis 23 (2002) 1297-1305
34. Cover C.M., Hsieh S.J., Cram E.J., Hong C., Riby J.E., Bjeldanes L.F., et al. Indole-3-carbinol and tamoxifen cooperate to arrest the cell cycle of MCF-7 human breast cancer cells. Cancer Res 59 (1999) 1244-1251
35. Stephensen P.U., Bonnesen C., Schaldach C., Andersen O., Bjeldanes L.F., and Vang O. N-Methoxyindole-3-carbinol is a more efficient inducer of cytochrome P-450 1A1 in cultured cells than indol-3-carbinol. Nutr Cancer 36 (2000) 112-121
36. Yudina L.N., Korolev A.M., Reznikova M.I., and Preobrazhenskaya M.N. Study of neoascorbigen. Chem Heterocycl Compd (Russ) 2 (2000) 178-186
37. Korolev A.M., Yudina L.N., Rozhkov I.I., Lysenkova L.N., Lazhko E.I., Luzikov Y.N., et al. The formation of 2-hydroxy-4-hydroxymethyl-3-(indol-3-yl)-cyclopent-2-enone derivatives from ascorbigens. Carbohydr Res 330 (2001) 469-477
38. Somei M., and Kawasaki S. A new and simple synthesis of N-hydroxyindole derivatives. Heterocycles 29 (1989) 1251-1254
39. Brandi G., Paiardini M., Cervasi B., Fiorucci C., Filippone P., De Marco C., et al. A new indole-3-carbinol tetrameric derivative inhibits cyclin-dependent kinase 6 expression, and induces G1 cell cycle arrest in both estrogen-dependent and estrogen-independent breast cancer cell lines. Cancer Res 63 (2003) 4028-4036
40. Chao W.R., Yean D., Amin K., Green C., and Jong L. Computer-aided rational drug design: a novel agent (SR13668) designed to mimic the unique anticancer mechanisms of dietary indole-3-carbinol to block Akt signaling. J Med Chem 50 (2007) 3412-3415
41. Garikapaty V.P., Ashok B.T., Tadi K., Mittelman A., and Tiwari R.K. 3,3′-Diindolylmethane downregulates pro-survival pathway in hormone independent prostate cancer. Biochem Biophys Res Commun 340 (2006) 718-725