Urologic Oncology: Seminars and Original Investigations
Volume 26, Issue 4 , Pages 378-385 , July 2008

(Z)-1,1-Dichloro-2-(4-methoxyphenyl)-3-phenylcyclopropane induces concentration-dependent growth inhibition, apoptosis, and coordinates regulation of apoptotic genes in TRAMP cells

  • Catherine A. Thomas, Ph.D.

      Affiliations

    • Department of Environmental and Occupational Health, University of Pittsburgh, Pittsburgh, PA 15260, USA
  • ,
  • Stephen G. Grant, Ph.D.

      Affiliations

    • Department of Environmental and Occupational Health, University of Pittsburgh, Pittsburgh, PA 15260, USA
    • Department of Obstetrics, Gynecology, and Reproductive Sciences and the Magee-Womens Research Institute, University of Pittsburgh, Pittsburgh, PA 15260, USA
    • University of Pittsburgh Cancer Institute, Pittsburgh, PA 15260, USA
  • ,
  • Beth R. Pflug, Ph.D.

      Affiliations

    • Department of Urology, University of Pittsburgh, Pittsburgh, PA 15260, USA
  • ,
  • Robert H. Getzenberg, Ph.D.

      Affiliations

    • University of Pittsburgh Cancer Institute, Pittsburgh, PA 15260, USA
    • Department of Urology, University of Pittsburgh, Pittsburgh, PA 15260, USA
    • Department of Pathology, University of Pittsburgh, Pittsburgh, PA 15260, USA
    • Department of Pharmacology, University of Pittsburgh, Pittsburgh, PA 15260, USA
  • ,
  • Billy W. Day, Ph.D.

      Affiliations

    • Department of Environmental and Occupational Health, University of Pittsburgh, Pittsburgh, PA 15260, USA
    • University of Pittsburgh Cancer Institute, Pittsburgh, PA 15260, USA
    • Department of Pharmaceutical Sciences, University of Pittsburgh, Pittsburgh, PA 15260, USA
    • Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA
    • Corresponding Author InformationCorresponding author. Tel.: +1-412-648-9706, fax: +1-412-383-5298.

Received 16 February 2007 ,Accepted 21 February 2007.

References 

  1. American Cancer Society. Cancer Facts and Figures. 2004;Atlanta, GA, USA
  2. Parker SL, Tong T, Bolden S, et al. Cancer statistics. CA Cancer J Clin. 1997;47:5–27
  3. Gingrich JR, Greenberg NM. A transgenic mouse prostate cancer model. Toxicol Pathol. 1996;24:502–504
  4. Gingrich JR, Barrios RJ, Morton RA, et al. Metastatic prostate cancer in a transgenic mouse. Cancer Res. 1996;56:4096–4102
  5. SoRelle R. Mouse models prove to be real GEMs. 2003;From the Laboratories at Baylor College of Medicine, Houston, Texas
  6. Foster BA, Gingrich JR, Kwon ED, et al. Characterization of prostatic epithelial cell lines derived from transgenic adenocarcinoma of the mouse prostate (TRAMP) model. Cancer Res. 1997;57:3325–3330
  7. Gingrich JR, Barrios RJ, Foster BA, et al. Pathologic progression of autochthonous prostate cancer in the TRAMP model. Prostate Cancer Prostatic Dis. 1999;2:70–75
  8. Foster BA, Kaplan PJ, Greenberg NM. Characterization of the FGF axis and identification of a novel FGFR1iiic isoform during prostate cancer progression in the TRAMP model. Prostate Cancer Prostatic Dis. 1999;2:76–82
  9. Kaplan-Lefko PJ, Chen TM, Ittmann MM, et al. Pathobiology of autochthonous prostate cancer in a preclinical transgenic mouse model. Prostate. 2003;55:219–237
  10. Freeman KW, Gangula RD, Welm BE, et al. Conditional activation of fibroblast growth factor receptor (FGFR) 1, but not FGFR2, in prostate cancer cells leads to increased osteopontin induction, extracellular signal-regulated kinase activation, and in vivo proliferation. Cancer Res. 2003;63:6237–6243
  11. Ter Haar E, Hamel E, Balachandran R, et al. Cellular targets of the antibreast cancer agent Z-1,1-dichloro-2,3-diphenylcyclopropane: Type II estrogen binding sites and tubulin. Anticancer Res. 1997;17:1861–1870
  12. Magarian RA, Benjamin EJ. Synthesis of cyclopropyl analogs of stilbene and stilbenediol as possible antiestrogens. J Pharm Sci. 1975;64:1626–1632
  13. Pento JT, Magarian RA, Wright RJ, et al. Nonsteroidal estrogens and antiestrogens (Biological activity of cyclopropyl analogs of stilbene and stilbenediol). J Pharm Sci. 1981;70:339–343
  14. Pento JT, Magarian RA, King MM. A comparison of the efficacy for antitumor activity of the nonsteroidal antiestrogens Analog II and tamoxifen in DMBA-induced rat mammary tumors. Cancer Lett. 1982;15:261–269
  15. King MM, Magarian RA, Terao J, et al. Effects of nonsteroidal antiestrogens, Analog II, and tamoxifen on a metastatic transplantable rat mammary tumor. J Natl Cancer Inst. 1985;74:447–451
  16. Day BW, Magarian RA, Pento JT, et al. Synthesis and biological evaluation of 1,1-dichloro-2,2,3-triarylcyclopropanes as pure antiestrogens. J Med Chem. 1991;34:842–851
  17. Ter Haar E, Day BW. Cytostatic and cytotoxic action of Z-1,1-dichloro-2,3-diphenylcyclopropane in three human breast cancer cell lines. Anticancer Res. 1996;16:1107–1115
  18. Jonnalagadda SS, Ter Haar E, Hamel E, et al. Synthesis and biological evaluation of 1,1-dichloro-2,3-diarylcyclopropanes as antitubulin and antibreast cancer agents. Bioorg Med Chem. 1997;5:715–722
  19. Balachandran R, Ter Haar E, Welsh MJ, et al. Induction of human breast cancer cell apoptosis from G2/M preceded by stimulation into the cell cycle by Z-1,1-dichloro-2,3-diphenylcyclopropane. Biochem Pharmacol. 1997;57:97–110
  20. Balachandran R, Grant SG, Welsh MJ, et al. Z-1,1-dichloro-2,3-diphenylcyclopropanes block human prostate carcinoma cell proliferation, inhibit prostate-specific antigen expression, and initiate apoptosis. Prostate. 2000;45:277–288
  21. Griffin MT, Magarian RA, Jain P, et al. Synthesis, a biological evaluation of a series of gem-dichlorocyclopropanes as antitumor agents. Anticancer Drug Des. 1992;7:49–66
  22. Chomczynski P, Sacchi N. Single-step method of RNA isolation by acid guanidinium thiocyanate-phenol-chloroform extraction. Anal Biochem. 1987;162:156–159
  23. Chomczynski P. A reagent for the single-step simultaneous isolation of RNA, DNA, and proteins from cell and tissue samples. Biotechniques. 1993;15:532–537
  24. Ren B, Yu YP, Jing L, et al. Gene expression analysis of human soft tissue leiomyosarcomas. Hum Pathol. 2003;34:549–558
  25. Satoh MS, Lindahl T. Role of poly(ADP-ribose) formation in DNA repair. Nature. 1992;356:356–358
  26. Hsu SY, Hsueh AJ. Tissue-specific Bcl-2 protein partners in apoptosis: An ovarian paradigm. Physiol Rev. 2000;80:593–614
  27. Yakovlev AG, Di Giovanni S, Wang G, et al. BOK and NOXA are essential mediators of p53-dependent apoptosis. J Biol Chem. 2004;279:28367–28374
  28. Yoon Y, Ao Z, Cheng Y, et al. Murine Siva-1 and Siva-2, alternate splice forms of the mouse Siva gene, both bind to CD27 but differentially transduce apoptosis. Oncogene. 1999;18:7174–7179
  29. Xue L, Chu F, Cheng Y, et al. Siva-1 binds to and inhibits BCL-X(L)-mediated protection against UV radiation-induced apoptosis. Proc Natl Acad Sci USA. 2002;99:6925–6930
  30. Fortin A, MacLaurin JG, Arbour N, et al. The proapoptotic gene SIVA is a direct transcriptional target for the tumor suppressors p53 and E2F1. J Biol Chem. 2004;279:28706–28714
  31. Ayala GE, Dai H, Ittmann M, et al. Growth and survival mechanisms associated with perineural invasion in prostate cancer. Cancer Res. 2004;64:6082–6090
  32. Holcik M, Lefebvre CA, Hicks K, et al. Cloning and characterization of the rat homologues of the inhibitor of apoptosis protein 1, 2, and 3 genes. BMC Genomics. 2002;3:5
  33. Pati D, Meistrich ML, Plon SE. Cdc34 and Rad6B ubiquitin-conjugating enzymes target repressors of cyclic AMP-induced transcription for proteolysis. Mol Cell Biol. 1999;19:5001–5013
  34. Hansen MB, Mitchelmore C, Kjaerulff KM, et al. Mouse Atf5: Molecular cloning of two novel mRNAs, genomic organization, and odorant sensory neuron localization. Genomics. 2002;80:344–350
  35. Angelastro JM, Ignatova TN, Kukekov VG, et al. Regulated expression of ATF5 is required for the progression of neural progenitor cells to neurons. J Neurosci. 2003;23:4590–4600
  36. Morris JA, Kandpal G, Ma L, et al. DISC1 (disrupted-in-schizophrenia 1) is a centrosome-associated protein that interacts with MAP1A, MIPT3, ATF4/5, and NUDEL: Regulation and loss of interaction with mutation. Hum Mol Genet. 2003;12:1591–1608
  37. Fernandez P, Carretero J, Medina PP, et al. Distinctive gene expression of human lung adenocarcinomas carrying LKB1 mutations. Oncogene. 2004;23:5084–5091
  38. Rumohr JA, Chang WW. Current chemotherapeutic approaches for androgen-independent prostate cancer. Curr Opin Investig Drugs. 2006;7:529–533

PII: S1078-1439(07)00068-3

doi: 10.1016/j.urolonc.2007.02.013

Urologic Oncology: Seminars and Original Investigations
Volume 26, Issue 4 , Pages 378-385 , July 2008