Spongian diterpenoids inhibit androgen receptor activity

Molecular Cancer Therapeutics

Volumn 12, Issue 5, 2013, Pages 621-631

  Yang, Yu Chi ^a   Meimetis, Labros G ^b   Tien, Amy H ^a   Mawji, Nasrin R ^a   Carr, Gavin ^b   Wang, Jun ^a   Andersen, Raymond J ^b   Sadar, Marianne D ^a  

^a BRITISH COLUMBIA CANCER AGENCY   (Canada)

^b UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ANDROGEN RECEPTOR; ANTIANDROGEN; BICALUTAMIDE; DITERPENOID; FURANODITERPENOID SPONGIA 13 (16), 14 DIEN 19 OIC ACID; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; CELL PROLIFERATION; CELL STRAIN LNCAP; COMPETITIVE INHIBITION; CONTROLLED STUDY; DRUG SCREENING; HIGH THROUGHPUT SCREENING; HUMAN; HUMAN CELL; KIDNEY CELL; LIGAND BINDING; MALE; MOUSE; NONHUMAN; PRIORITY JOURNAL; PROSTATE CANCER; PROTEIN EXPRESSION; PROTEIN INTERACTION; SEMINAL VESICLE; STRUCTURE ACTIVITY RELATION; WILD TYPE;

ANDROGEN RECEPTOR ANTAGONISTS; ANDROGENS; ANIMALS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; DITERPENES; DOSE-RESPONSE RELATIONSHIP, DRUG; GENE EXPRESSION REGULATION, NEOPLASTIC; HUMANS; MALE; MICE; PROSTATIC NEOPLASMS; PROTEIN BINDING; PROTEIN INTERACTION DOMAINS AND MOTIFS; RECEPTORS, ANDROGEN; TRANSCRIPTION, GENETIC;

EID: 84877672537     PISSN: 15357163     EISSN: 15388514     Source Type: Journal    
DOI: 10.1158/1535-7163.MCT-12-0978     Document Type: Article

References (49)

1. Rogers CG, Khan MA, Craig-Miller M, Veltri RW, Partin AW. Natural history of disease progression in patients who fail to achieve an undetectable prostate-specific antigen level after undergoing radical prostatectomy. Cancer 2004;101:2549-56.
2. Attard G, Cooper CS, de Bono JS. Steroid hormone receptors in prostate cancer: a hard habit to break? Cancer Cell 2009;16: 458-62.
3. Heinlein CA, Chang C. Androgen receptor in prostate cancer. Endocr Rev 2004;25:276-308.
4. Zegarra-Moro OL, Schmidt LJ, Huang H, Tindall DJ. Disruption of androgen receptor function inhibits proliferation of androgen-refractory prostate cancer cells. Cancer Res 2002;62:1008-13.
5. Yuan X, Balk SP. Mechanisms mediating androgen receptor reactivation after castration. Urol Oncol 2009;27:36-41.
6. Wang Q, Li W, Zhang Y, Yuan X, Xu K, Yu J, et al. Androgen receptor regulates a distinct transcription program in androgen-independent prostate cancer. Cell 2009;138:245-56.
7. Visakorpi T, Hyytinen E, Koivisto P, Tanner M, Keinanen R, Palmberg C, et al. In vivo amplification of the androgen receptor gene and progression of human prostate cancer. Nat Genet 1995;9:401-6.
8. Koivisto P, Kononen J, Palmberg C, Tammela T, Hyytinen E, Isola J, et al. Androgen receptor gene amplification: a possible molecular mechanism for androgen deprivation therapy failure in prostate cancer. Cancer Res 1997;57:314-9.
9. Chen CD, Welsbie DS, Tran C, Baek SH, Chen R, Vessella R, et al. Molecular determinants of resistance to antiandrogen therapy. Nat Med 2004;10:33-9.
10. Zhao XY, Malloy PJ, Krishnan AV, Swami S, Navone NM, Peehl DM, et al. Glucocorticoids can promote androgen-independent growth of prostate cancer cells through a mutated androgen receptor. Nat Med 2000;6:703-6.
11. Hara T, Miyazaki J, Araki H, Yamaoka M, Kanzaki N, Kusaka M, et al. Novel mutations of androgen receptor: a possible mechanism of bicalutamide withdrawal syndrome. Cancer Res 2003;63:149-53.
12. Haile S, Sadar MD. Androgen receptor and its splice variants in prostate cancer. Cell Mol Life Sci 2011;68:3971-81.
13. Culig Z, Hobisch A, Cronauer MV, Radmayr C, Trapman J, Hittmair A, et al. Androgen receptor activation in prostatic tumor cell lines by insulin-like growth factor-I, keratinocyte growth factor, and epidermal growth factor. Cancer Res 1994;54:5474-8.
14. Nazareth LV, Weigel NL. Activation of the human androgen receptor through a protein kinase A signaling pathway. J Biol Chem 1996;271: 19900-7.
15. Sadar MD. Androgen-independent induction of prostate-specific antigen gene expression via cross-talk between the androgen receptor and protein kinase A signal transduction pathways. J Biol Chem 1999;274:7777-83.
16. Ueda T, Bruchovsky N, Sadar MD. Activation of the androgen receptor N-terminal domain by interleukin-6 via MAPK and STAT3 signal transduction pathways. J Biol Chem 2002;277:7076-85.
17. Blaszczyk N, Masri BA, Mawji NR, Ueda T, McAlinden G, Duncan CP, et al. Osteoblast-derived factors induce androgen-independent proliferation and expression of prostate-specific antigen in human prostate cancer cells. Clin Cancer Res 2004;10:1860-9.
18. Ngan ES, Hashimoto Y, Ma ZQ, Tsai MJ, Tsai SY. Overexpression of Cdc25B, an androgen receptor coactivator, in prostate cancer. Oncogene 2003;22:734-9.
19. Debes JD, Sebo TJ, Lohse CM, Murphy LM, Haugen DA, Tindall DJ. p300 in prostate cancer proliferation and progression. Cancer Res 2003;63:7638-40.
20. Comuzzi B, Nemes C, Schmidt S, Jasarevic Z, Lodde M, Pycha A, et al. The androgen receptor co-activator CBP is up-regulated following androgen withdrawal and is highly expressed in advanced prostate cancer. J Pathol 2004;204:159-66.
21. Agoulnik IU, Vaid A, Bingman WE III, Erdeme H, Frolov A, Smith CL, et al. Role of SRC-1 in the promotion of prostate cancer cell growth and tumor progression. Cancer Res 2005;65:7959-67.
22. Montgomery RB, Mostaghel EA, Vessella R, Hess DL, Kalhorn TF, Higano CS, et al. Maintenance of intratumoral androgens in metastatic prostate cancer: a mechanism for castration-resistant tumor growth. Cancer Res 2008;68:4447-54.
23. de Bono JS, Logothetis CJ, Molina A, Fizazi K, North S, Chu L, et al. Abiraterone and increased survival in metastatic prostate cancer. N Engl J Med 2011;364:1995-2005.
24. Scher HI, Fizazi K, Saad F, Taplin ME, Sternberg CN, Miller K, et al. Increased survival with enzalutamide in prostate cancer after chemotherapy. N Engl J Med 2012;367:1187-97.
25. Suzuki H, Okihara K, Miyake H, Fujisawa M, Miyoshi S, Matsumoto T, et al. Alternative nonsteroidal antiandrogen therapy for advanced prostate cancer that relapsed after initial maximum androgen blockade. J Urol 2008;180:921-7.
26. Kassouf W, Tanguay S, Aprikian AG. Nilutamide as second line hormone therapy for prostate cancer after androgen ablation fails. J Urol 2003;169:1742-4.
27. Hu R, Lu C, Mostaghel EA, Yegnasubramanian S, Gurel M, Tannahill C, et al. Distinct transcriptional programs mediated by the ligand-dependent full-length androgen receptor and its splice variants in castration-resistant prostate cancer. Cancer Res 2012; 72:3457-62
28. Andersen RJ, Mawji NR, Wang J, Wang G, Haile S, Myung JK, et al. Regression of castrate-recurrent prostate cancer by a small-molecule inhibitor of the amino-terminus domain of the androgen receptor. Cancer Cell 2010;17:535-46.
29. Romanuik TL, Ueda T, Le N, Haile S, Yong TM, Thomson T, et al. Novel biomarkers for prostate cancer including noncoding transcripts. Am J Pathol 2009;175:2264-76.
30. Romanuik TL, Wang G, Holt RA, Jones SJ, Marra MA, Sadar MD. Identification of novel androgen-responsive genes by sequencing of Long SAGE libraries. BMC Genomics 2009;10:476.
31. Wang G, Haile S, Comuzzi B, Tien AH, Wang J, Yong TM, et al. Osteoblast-derived factors induce an expression signature that identifies prostate cancer metastasis and hormonal progression. Cancer Res 2009;69:3433-42.
32. Kolvenbag GJ, Blackledge GR, Gotting-Smith K. Bicalutamide (Casodex) in the treatment of prostate cancer: history of clinical development. Prostate 1998;34:61-72.
33. Tran C, Ouk S, Clegg NJ, Chen Y, Watson PA, Arora V, et al. Development of a second-generation antiandrogen for treatment of advanced prostate cancer. Science 2009;324:787-90.
34. Veldscholte J, Ris-Stalpers C, Kuiper GG, Jenster G, Berrevoets C, Claassen E, et al. A mutation in the ligand binding domain of the androgen receptor of human LNCaP cells affects steroid binding characteristics and response to anti-androgens. Biochem Biophys Res Commun 1990;173:534-40.
35. Balk SP, Ko YJ, Bubley GJ. Biology of prostate-specific antigen. J Clin Oncol 2003;21:383-91.
36. Sun Z, Pan J, Balk SP. Androgen receptor-associated protein complex binds upstream of the androgen-responsive elements in the promoters of human prostate-specific antigen and kallikrein 2 genes. Nucleic Acids Res 1997;25:3318-25.
37. Magee JA, Chang LW, Stormo GD, Milbrandt J. Direct, androgen receptor-mediated regulation of the FKBP5 gene via a distal enhancer element. Endocrinology 2006;147:590-8.
38. Lin B, Ferguson C, White JT, Wang S, Vessella R, True LD, et al. Prostate-localized and androgen-regulated expression of the membrane-bound serine protease TMPRSS2. Cancer Res 1999;59: 4180-4.
39. Sun C, Shi Y, Xu LL, Nageswararao C, Davis LD, Segawa T, et al. Androgen receptor mutation (T877A) promotes prostate cancer cell growth and cell survival. Oncogene 2006;25:3905-13.
40. He B, Lee LW, Minges JT, Wilson EM. Dependence of selective gene activation on the androgen receptor NH2-and COOH-terminal interaction. J Biol Chem 2002;277:25631-9.
41. Masiello D, Cheng S, Bubley GJ, Lu ML, Balk SP. Bicalutamide functions as an androgen receptor antagonist by assembly of a transcriptionally inactive receptor. J Biol Chem 2002;277: 26321-6.
42. Poujol N, Wurtz JM, Tahiri B, Lumbroso S, Nicolas JC, Moras D, et al. Specific recognition of androgens by their nuclear receptor. A structure-function study. J Biol Chem 2000;275:24022-31.
43. Welsh M, Moffat L, Jack L, McNeilly A, Brownstein D, Saunders PT, et al. Deletion of androgen receptor in the smooth muscle of the seminal vesicles impairs secretory function and alters its responsiveness to exogenous testosterone and estradiol. Endocrinology 2010; 151:3374-85.
44. Yeh S, Tsai MY, Xu Q, Mu XM, Lardy H, Huang KE, et al. Generation and characterization of androgen receptor knockout (ARKO) mice: an in vivo model for the study of androgen functions in selective tissues. Proc Natl Acad Sci U S A 2002;99:13498-503.
45. Arno M, Betancur-Galvis L, Gonzalez MA, Sierra J, Zaragoza RJ. Synthesis and cytotoxic activity of novel C7-functionalized spongiane diterpenes. Bioorg Med Chem 2003;11:3171-7.
46. Betancur-Galvis L, Zuluaga C, Arno M, Gonzalez MA, Zaragoza RJ. Cytotoxic effect (on tumor cells) and in vitro antiviral activity against herpes simplex virus of synthetic spongiane diterpenes. J Nat Prod 2002;65:189-92.
47. Kemppainen JA, Langley E, Wong CI, Bobseine K, Kelce WR, Wilson EM. Distinguishing androgen receptor agonists and antagonists: distinct mechanisms of activation by medroxyprogesterone acetate and dihydrotestosterone. Mol Endocrinol 1999;13: 440-54.
48. Bramson HN, Hermann D, Batchelor KW, Lee FW, James MK, Frye SV. Unique preclinical characteristics of GG745, a potent dual inhibitor of 5AR. J Pharmacol Exp Ther 1997;282:1496-502.
49. Berrevoets CA, Veldscholte J, Mulder E. Effects of antiandrogens on transformation and transcription activation of wild-type and mutated (LNCaP) androgen receptors. J Steroid Biochem Mol Biol 1993;46: 731-6.