Synthetic dimer of indole-3-carbinol: Second generation diet derived anti-cancer agent in hormone sensitive prostate cancer

Prostate

Volumn 66, Issue 5, 2006, Pages 453-462

  Garikapaty, Venkata P S ^a   Ashok, Badithe T ^a   Tadi, Kiranmayi ^a   Mittelman, Abraham ^a   Tiwari, Raj K ^a  

^a NEW YORK MEDICAL COLLEGE   (United States)

Author keywords

Akt; Androgen receptor; Cruciferous vegetables; Diindolylmethane; Prostate cancer

Indexed keywords

2,3 BIS(2 METHOXY 4 NITRO 5 SULFOPHENYL) 2H TETRAZOLIUM 5 CARBOXANILIDE; 3 INDOLEMETHANOL; ANDROGEN; ANDROGEN RECEPTOR; ANILIDE; ANTINEOPLASTIC AGENT; CYCLIN D1; CYCLIN DEPENDENT KINASE 4; CYTOPLASM PROTEIN; DIINDOYLMETHANE; DIMER; ISOTHIOCYANIC ACID DERIVATIVE; METRIBOLONE; PHOSPHATIDYLINOSITOL 3 KINASE; PHOSPHOPROTEIN; PROTEIN KINASE B; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; ARTICLE; BIOASSAY; CELL STRAIN LNCAP; CHEMOPROPHYLAXIS; CONTROLLED STUDY; CRUCIFEROUS VEGETABLE; DNA SYNTHESIS INHIBITION; DRUG EFFECT; DRUG MECHANISM; GROWTH INHIBITION; HORMONE SENSITIVE PROSTATE CANCER; HORMONE SENSITIVITY; HUMAN; HUMAN CELL; IC 50; PRIORITY JOURNAL; PROSTATE CANCER; PROTEIN CONTENT; VEGETABLE; WESTERN BLOTTING; XTT ASSAY;

ANDROGENS; ANTICARCINOGENIC AGENTS; CELL CYCLE; CELL DEATH; CELL DIVISION; CELL LINE, TUMOR; DIET; DIETARY SUPPLEMENTS; DIMERIZATION; DNA, NEOPLASM; HUMANS; INDOLES; MALE; PROSTATIC NEOPLASMS; RECEPTORS, ANDROGEN;

EID: 33645349584     PISSN: 02704137     EISSN: 10970045     Source Type: Journal    
DOI: 10.1002/pros.20350     Document Type: Article

References (51)

1. Landis SH, Murray T, Bolden S, Wingo PA. Cancer statistics, 1999. CA Cancer J Clin 1999;49:8-31.
2. David AK, Khwaja R, Hudes GR. Treatments for improving survival of patients with prostate cancer. Drugs Aging 2003;20:683-699.
3. Sakr WA. Prostatic intraepithelial neoplasia: A marker for high risk groups and a potential target for chemoprevention. Eur Urol 1999;35:474-478.
4. Bostwick DG, Neumann R, Qian J, Cheng L. Reversibility of prostatic intraepithelial neoplasia: Implications for chemoprevention. Eur Urol 1999;35:492-495.
5. Kelloff GJ, Lieberman R, Steele VE, Boone CW, Lubet RA, Kopelovitch L, Malone WA, Crowell JA, Sigman CC. Chemoprevention of prostate cancer: concepts and strategies. Eur Urol 1999;35:342-350.
6. Stoner GD, Morse MA, Kelloff GJ. Perspectives in cancer chemoprevention. Environ Health Perspect 1997;105(Suppl):945-954.
7. Cohen JH, Kristal AR, Stanford JL. Fruit and vegetable intakes and prostate cancer risk. J Natl Cancer Inst 2000;92:61-68.
8. Kolonel LN, Hankin JH, Whittemore AS, Wu AH, Gallagher RP, Wilkens LR, John EM, Howe GR, Dreon DM, West DW, Paffenbarger RS Jr. Vegetables, fruits, legumes and prostate cancer: A multiethnic case control study. Cancer Epidemiol Biomarkers Prev 2000;9:795-804.
9. Ashok BT, Chen Y, Liu X, Bradlow HL, Mittelman A, Tiwari RK. Abrogation of estrogen-mediated cellular and biochemical effects by indole-3-carbinol. Nutr Cancer 2001;41:180-187.
10. Ashok BT, Chen YG, Liu X, Garikapaty VP, Seplowitz R, Tschorn J, Roy K, Mittelman A, Tiwari RK. Multiple molecular targets of indole-3-carbinol, a chemopreventive anti-estrogen in breast cancer. Eur J Cancer Prev 2002;11(Suppl 2):S86-S93.
11. Zhang J, Hsu B A JC, Kinseth B A MA, Bjeldanes LF, Firestone GL. Indole-3-carbinol induces a G1 cell cycle arrest and inhibits prostate-specific antigen production in human LNCaP prostate carcinoma cells. Cancer 2003;98:2511-2520.
12. Tiwari RK, Guo L, Bradlow HL, Telang NT, Osborne MP. Selective responsiveness of human breast cancer cells to indole-3-carbinol, a chemopreventive agent. J Natl Cancer Inst 1994;86:126-131.
13. De Kruif CA, Marsman JW, Venekamp JC, Falke HE, Noordhoek J, Blaauboer BJ, Wortelboer HM. Structure elucidation of acid reaction products of indole-3-carbinol: Detection in vivo and enzyme induction in vitro. Chem Biol Interact 1991;80:303-315.
14. Riby JE, Feng C, Chang YC, Schaldach CM, Firestone GL, Bjeldanes LF. The major cyclic trimer product of indole-3-carbinol is a strong agonist of the estrogen receptor signaling pathway. Biochemistry 2000;39:910-918.
15. Riby JE, Chang GH, Firestone GL, Bjeldanes LF. Ligand-independent activation of estrogen receptor function by 3,3′-diindolylmethane in human breast cancer cells. Biochem Pharmacol 2000;60:167-177.
16. Xue L, Schaldach CM, Janosik T, Bergman J, Bjeldanes LF. Effects of analogs of indole-3-carbinol cyclic trimerization product in human breast cancer cells. Chem Biol Interact 2005;152:119-129.
17. Chang YC, Riby J, Chang GH, Peng BC, Firestone G, Bjeldanes LF. Cytostatic and antiestrogenic effects of 2-(indol-3-ylmethyl)-3,3′- diindolylmethane, a major in vivo product of dietary indole-3-carbinol. Biochem Pharmacol 1999;58:825-834.
18. Arneson DW, Hurwitz A, McMahon LM, Robaugh D. Presence of 3,3′-dindolylmethane in human plasma after oral administration of indole-3-carbinol. Proc Amer Assoc Cancer Res 1999;40:2833.
19. Vivanco I, Sawyers CL. The phosphatidylinositol 3-Kinase-AKT pathway in human cancer. Nature Rev 2002;2:489-501.
20. Cantley LC. The phosphoinositide 3-Kinase pathway. Science 2002;296:1655-1657.
21. Barnett SF, Bilodeau MT, Lindsley CW. The Akt/PKB family of protein kinases: A review of small molecule inhibitors and progress towards target validation. Curr Top Med Chem 2005;5:109-125.
22. Osaki M, Oshimura M, Ito H. PI3K-Akt pathway: Its functions and alterations in human cancer. Apoptosis 2004;9:667-676.
23. Garikapaty VPS, Ashok BT, Chen YG, Mittelman A, Iatropoulos M, Tiwari RK. Anticarcinogenic and antimetastatic proerties of indole-3-carbinol in prostate cancer. Oncology Rep 2004;13:89-93.
24. Ashok BT, Kim E, Mittelman A, Tiwari RK. Proteasome inhibitors differentially affect heat shock protein response in cancer cells. Int J Mol Med 2001;8:385-390.
25. Laemmli UL. Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 1970;227:680-685.
26. Chen Y, Ashok BT, Liu X, Garikapaty VPS, Mittelman A, Tiwari RK. Induction of gp96 by immune cytokines. Cell Stress Chaperones 2003;8:242-248.
27. Miyamoto H, Messing EM, Chang C. Androgen deprivation therapy for prostate cancer: Current status and future prospects. Prostate 2004;61:332-353.
28. Scher HI, Buchanan G, Gerald W, Butler LM, Tilley WD. Targeting the androgen receptor: Improving outcomes for castration-resistant prostate cancer. Endocr Relat Cancer 2004;11:459-476.
29. Bosland M. The role of steroid hormones in prostate carcinogenesis. J Natl Cancer Inst Monographs 2000;27:39-60.
30. DeMarzo AM, Nelson WG, Isaacs WB, Epstein JI. Pathological and molecular aspects of prostate cancer. The Lancet 2003;361:955-964.
31. Debes JD, Tindall DJ. The role of androgens and the androgen receptor in prostate cancer. Cancer Lett 2002;187:1-7.
32. Culig Z, Klocker H, Bartsch G, Hobisch A. Androgen receptors in prostate cancer. Endocr Relat Cancer 2002;9:155-170.
33. Jenster G. The role of the androgen receptor in the development and progression of prostate cancer. Semin Oncol 1999;26:407-421.
34. Brinkmann AO, Blok LJ, de Ruiter PE, Doesburg P, Steketee K, Berrevoets CA, Trapman J. Mechanisms of androgen receptor activation and function. J Steroid Biochem Mol Biol 1999;69:307-313.
35. Berrevoets CA, Doesburg P, Steketee K, Trapman J, Brinkmann AO. Functional interactions of the AF-2 activation domain core region of the human androgen receptor with the amino-terminal domain and with the transcriptional coactivator TIF2 (transcriptional intermediary factor2). Mol Endocrinol 1998;12:1172-1183.
36. Langley E, Kemppainen JA, Wilson EM. Intermolecular NH2-/carboxyl- terminal interactions in androgen receptor dimerization revealed by mutations that cause androgen insensitivity. J Biol Chem 1998;273:92-101.
37. Spencer TE, Jenster G, Burcin MM, Allis CD, Zhou J, Mizzen CA, McKenna NJ, Onate SA, Tsai SY, Tsai MJ, O'Malley BW. Steroid receptor coactivator-1 is a histone acetyltransferase. Nature 1997;389:194-198.
38. Kouzarides T. Histone acetylases and deacetylases in cell proliferation. Curr Opin Genet Dev 1999;9:40-48.
39. Vlietstra RJ, vanAlewijk DC, Hermans KG, et al. Frequent inactivation of PTEN in prostate cancer cell lines and xenografts. Cancer Res 1998;58:2720-2723.
40. Cantley LC, Neel BG. New insights into tumor suppression: PTEN suppresses tumor formation by restraining the phosphoinositide 3-kinase/AKT pathway. Proc Natl Acad Sci USA 1999;96:4240-4245.
41. Li J, Yen C, Liaw D, Podsypanina K, Bose S, Wang SI, Pue J, Miliaresis C, Rodgers L, McCombie R, Bigner SH, Giovanella BC, Ittmann M, Tycko B, Hibshoosh H, Wigler MH, Parsons R. PTEN, a putative protein tyrosine phosphatase gene mutated in human brain, breast, and prostate cancer. Science 1997;275:1943-1947.
42. Gioeli D, Ficarro SB, Kwiek JJ, Aaronson D, Hancock M, Catling AD, White FM, Christian RE, Settlage RE, Shabanowitz J, Hunt DF, Weber MJ. Androgen receptor phosphorylation. Regulation and identification of phosphorylation sites. J Biol Chem 2002;277:29304-29314.
43. Truica CI, Byers S, Gelmann EP. Beta-catenin affects androgen receptor transcriptional activity and ligand specificity. Cancer Res 2000;60:4709-4713.
44. Sharma M, William WW, Sun Z. Phosphatidylinositol 3-kinase/Akt stimulates androgen pathway through GSK3β inhibition and nuclear beta-catenin accumulation. J Biol Chem 2002;277:30935-30941.
45. Yang F, Li X, Sharma M, Sasaki CY, Longo DL, Lim B, Sun Z. Linking beta-catenin to androgen-signaling pathway. J Biol Chem 2002;277:11336-11344.
46. Le HT, Schaldach CM, Firestone GL, Bjeldanes LF. Plant derived 3,33′-diindolyl methane is a strong androgen antagonist in human prostate cancer cells. J Biol Chem 2004;278:21136-21145.
47. Chinni SR, Sarkar FH. Akt inactivation is a key event in indole-3-carbinol-induced apoptosis in PC-3 cells. Clin Cancer Res 2002;8:1228-1236.
48. Rahman KW, Sarkar FH. Inhibition of nuclear translocation of nuclear factor-{kappa}B contributes to 3,3′-diindolylmethane-induced apoptosis in breast cancer cells. Cancer Res 2005;65:364-371.
49. Chang X, Tou JC, Hong C, Kim HA, Riby JE, Firestone GL, Bjeldanes LF. 3,3′-Diindolylmethane inhibits angiogenesis and the growth of transplantable human breast carcinoma in athymic mice. Carcinogenesis 2005;26:771-778.
50. Chen DZ, Qi M, Auborn KJ, Carter TH. Indole-3-carbinol and Diindolylmethane induce apoptosis of human cervical cancer cells and in murine HPV16-transgenic preneoplastic cervical epithelium. J Nutr 2001;131:3294-3302.
51. Leong H, Firestone GL, Bjeldanes LF. Cytostatic effects of 3,3′-diindolylmethane in human endometrial cancer cells result from an estrogen receptor-mediated increase in transforming growth factor-expression. Carcinogenesis 2001;22:1809-1817.