Table of Contents
ISRN Urology
Volume 2011 (2011), Article ID 301490, 9 pages
http://dx.doi.org/10.5402/2011/301490
Review Article

Novel Vitamin D Analogs for Prostate Cancer Therapy

1Boston University School of Medicine, Room M-1022, 715 Albany Street, Boston, MA 02118, USA
2Faculty of Pharmaceutical Sciences, Teikyo University, Midori-ku, Sagamihara, Kanagawa 252-5195, Japan

Received 15 May 2011; Accepted 3 June 2011

Academic Editors: A. M. El-Assmy, T. Nelius, K. Pummer, and F. Staerman

Copyright © 2011 Tai C. Chen and Atsushi Kittaka. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. A. Jemal, R. Siegel, E. Ward, Y. Hao, J. Xu, and M. J. Thun, “Cancer statistics, 2009,” CA Cancer Journal for Clinicians, vol. 59, no. 4, pp. 225–249, 2009. View at Publisher · View at Google Scholar · View at PubMed
  2. R. S. Kirby, “Recent advances in the medical management of prostate cancer,” British Journal of Clinical Practice, vol. 50, no. 2, pp. 88–93, 1996. View at Google Scholar
  3. H. Beltran, T. M. Beer, M. A. Carducci et al., “New therapies for castration-resistant prostate cancer: efficacy and safety,” European Urology, vol. 60, no. 2, pp. 279–290, 2011. View at Publisher · View at Google Scholar · View at PubMed
  4. G. J. Miller, “Vitamin D and prostate cancer: biologic interactions and clinical potentials,” Cancer and Metastasis Reviews, vol. 17, no. 4, pp. 353–360, 1999. View at Publisher · View at Google Scholar
  5. J. L. Osborn, G. G. Schwartz, D. C. Smith, R. Bahnson, R. Day, and D. L. Trump, “Phase II trial of oral 1,25-dihydroxyvitamin D (calcitriol) in hormone refractory prostate cancer,” Urologic Oncology, vol. 1, no. 5, pp. 195–198, 1995. View at Google Scholar
  6. C. Gross, T. Stamey, S. Hancock, and D. Feldman, “Treatment of early recurrent prostate cancer with 1,25-dihydroxyvitamin D3 (calcitriol),” Journal of Urology, vol. 159, no. 6, pp. 2035–2040, 1998. View at Google Scholar
  7. E. V. McCollum, N. Simmonds, J. E. Becker, P. G. Shipley, and R. W. Bunting, “Studies on experimental rickets. XXI. An experimental demonstration of the existence of a vitamin which promotes calcium deposition,” Journal of Biological Chemistry, vol. 53, pp. 293–312, 1922. View at Google Scholar
  8. H. F. DeLuca and H. K. Schnoes, “Metabolism and mechanism of action of vitamin D,” Annual Review of Biochemistry, vol. 45, pp. 631–666, 1976. View at Google Scholar
  9. FS Airey, “Vitamin D as a remedy for lupus vulgaris,” Medical World, vol. 64, pp. 807–810, 1946. View at Google Scholar
  10. J. Charpy, G. B. Dowling et al., “Vitamin D in cutaneous tuberculosis,” Lancet, vol. 2, no. 6472, p. 398, 1947. View at Google Scholar
  11. L. J. Holcik, “Treatment of psoriasis with large doses of vitamin D2,” Ceskoslovenska Dermatologie, vol. 24, no. 4, pp. 145–149, 1949. View at Google Scholar
  12. W. E. Stumpf, M. Sar, F. A. Reid et al., “Target cells for 1,25-dihydroxyvitamin D3 in intestinal tract, stomach, kidney, skin, pituitary, and parathyroid,” Science, vol. 206, no. 4423, pp. 1188–1190, 1979. View at Google Scholar
  13. K. Colston, M. Hirst, and D. Feldman, “Organ distribution of the cytoplasmic 1,25-dihydroxycholecalciferol receptor in various mouse tissues,” Endocrinology, vol. 107, no. 6, pp. 1916–1922, 1980. View at Google Scholar
  14. E. Abe, C. Miyaura, and H. Sakagami, “Differentiation of mouse myeloid leukemia cells induced by 1α,25-dihydroxyvitamin D3,” Proceedings of the National Academy of Sciences of the United States of America, vol. 78, no. 8, pp. 4990–4994, 1981. View at Google Scholar
  15. T. C. Chen and M. F. Holick, “Vitamin D and prostate cancer prevention and treatment,” Trends in Endocrinology and Metabolism, vol. 14, no. 9, pp. 423–430, 2003. View at Publisher · View at Google Scholar
  16. A. J. Brown and E. Slatopolsky, “Vitamin D analogs: therapeutic applications and mechanisms for selectivity,” Molecular Aspects of Medicine, vol. 29, no. 6, pp. 433–452, 2008. View at Publisher · View at Google Scholar · View at PubMed
  17. K. W. Colston, A. G. Mackay, S. Y. James, L. Binderup, S. Chander, and R. C. Coombes, “EB1089: a new vitamin D analogue that inhibits the growth of breast cancer cells in vivo and in vitro,” Biochemical Pharmacology, vol. 44, no. 12, pp. 2273–2280, 1992. View at Publisher · View at Google Scholar
  18. M. E. Valrance, A. H. Brunet, and J. Welsh, “Vitamin D receptor-dependent inhibition of mammary tumor growth by EB1089 and ultraviolet radiation in vivo,” Endocrinology, vol. 148, no. 10, pp. 4887–4894, 2007. View at Publisher · View at Google Scholar · View at PubMed
  19. V. Bhatia, M. K. Saini, X. Shen et al., “EB1089 inhibits the parathyroid hormone-related protein-enhanced bone metastasis and xenograft growth of human prostate cancer cells,” Molecular Cancer Therapeutics, vol. 8, no. 7, pp. 1787–1798, 2009. View at Publisher · View at Google Scholar · View at PubMed
  20. G. Liu, K. Oettel, G. Ripple et al., “Phase I trial of 1α-hydroxyvitamin D2 in patients with hormone refractory prostate cancer,” Clinical Cancer Research, vol. 8, no. 9, pp. 2820–2827, 2002. View at Google Scholar
  21. G. Liu, G. Wilding, M. J. Staab et al., “Phase II study of 1α-hydroxyvitamin D2 in the treatment of advanced androgen-independent prostate cancer,” Clinical Cancer Research, vol. 9, no. 11, pp. 4077–4083, 2003. View at Google Scholar
  22. J. Abe, M. Morikawa, K. Miyamoto et al., “Synthetic analogues of vitamin D3 with an oxygen atom in the side chain skeleton. A trial of the development of vitamin D compounds which exhibit potent differentiation-inducing activity without inducing hypercalcemia,” FEBS Letters, vol. 226, no. 1, pp. 58–62, 1987. View at Publisher · View at Google Scholar
  23. J. Y. Zhou, A. W. Norman, M. Lübbert, E. D. Collins, M. R. Uskokovic, and H. P. Koeffler, “Novel vitamin D analogs that modulate leukemic cell growth and differentiation with little effect on either intestinal calcium absorption or bone calcium mobilization,” Blood, vol. 74, no. 1, pp. 82–93, 1989. View at Google Scholar
  24. H. Asou, M. Koike, E. Elstner et al., “19-nor vitamin-D analogs: a new class of potent inhibitors of proliferation and inducers of differentiation of human myeloid leukemia cell lines,” Blood, vol. 92, no. 7, pp. 2441–2449, 1998. View at Google Scholar
  25. R. G. Mehta, R. M. Moriarty, R. R. Mehta, R. Penmasta, G. Lazzaro, and A. Constantinou, “Prevention of preneoplastic mammary lesion development by a novel vitamin D analogue, 1α-hydroxyvitamin D5,” Journal of the National Cancer Institute, vol. 89, no. 3, pp. 212–218, 1997. View at Google Scholar
  26. M. F. Boehm, P. Fitzgerald, A. Zou et al., “Novel nonsecosteroidal vitamin D mimics exert VDR-modulating activities with less calcium mobilization than 1,25-dihydroxyvitamin D3,” Chemistry and Biology, vol. 6, no. 5, pp. 265–275, 1999. View at Publisher · View at Google Scholar
  27. M. R. Uskokovic, P. Manchand, S. Marczak et al., “C-20 cyclopropyl vitamin D3 analogs,” Current Topics in Medicinal Chemistry, vol. 6, no. 12, pp. 1289–1296, 2006. View at Publisher · View at Google Scholar
  28. L. Adorini, G. Penna, S. Amuchastegui et al., “Inhibition of prostate growth and inflammation by the vitamin D3 receptor agonist BXL-628 (elocalcitol),” Journal of Steroid Biochemistry and Molecular Biology, vol. 103, no. 3-5, pp. 689–693, 2007. View at Publisher · View at Google Scholar · View at PubMed
  29. T. Saito, R. Okamoto, T. Haritunians et al., “Novel Gemini vitamin D3 analogs have potent antitumor activity,” Journal of Steroid Biochemistry and Molecular Biology, vol. 112, no. 1–3, pp. 151–156, 2008. View at Publisher · View at Google Scholar · View at PubMed
  30. J. L. Napoli, J. L. Sommerfeld, B. C. Pramanik et al., “19-Nor-10-ketovitamin D derivatives: unique metabolites of vitamin D3, vitamin D2, and 25-hydroxyvitamin D3,” Biochemistry, vol. 22, no. 15, pp. 3636–3640, 1983. View at Google Scholar
  31. K. L. Perlman, R. R. Sicinski, H. K. Schnoes, and H. F. DeLuca, “1α,25-Dihydroxy-19-nor-vitamin D3, a novel vitamin D-related compound with potential therapeutic activity,” Tetrahedron Letters, vol. 31, no. 13, pp. 1823–1824, 1990. View at Publisher · View at Google Scholar
  32. E. Slatopolsky, J. Finch, C. Ritter et al., “A new analog of calcitriol, 19-Nor-1,25-(OH)2D2, suppresses parathyroid hormone secretion in uremic rats in the absence of hypercalcemia,” American Journal of Kidney Diseases, vol. 26, no. 5, pp. 852–860, 1995. View at Google Scholar
  33. F. Llach, G. Keshav, M. V. Goldblat et al., “Suppression of parathyroid hormone secretion in hemodialysis patients by a novel vitamin D analogue: 19-nor-1,25-dihydroxyvitamin D2,” American Journal of Kidney Diseases, vol. 32, no. 2, supplement 2, pp. S48–S54, 1998. View at Google Scholar
  34. R. R. Sicinski, P. Rotkiewicz, A. Kolinski et al., “2-Ethyl and 2-ethylidene analogues of 1α,25-dihydroxy-19-norvitamin D3: synthesis, conformational analysis, biological activities, and docking to the modeled rVDR ligand binding domain,” Journal of Medicinal Chemistry, vol. 45, no. 16, pp. 3366–3380, 2002. View at Publisher · View at Google Scholar
  35. K. Ono, A. Yoshida, N. Saito et al., “Efficient synthesis of 2-modified 1α,25-dihydroxy-19-norvitamin D3 with Julia olefination: high potency in induction of differentiation on HL-60 cells,” Journal of Organic Chemistry, vol. 68, no. 19, pp. 7407–7415, 2003. View at Google Scholar
  36. A. Kittaka, N. Saito, S. Honzawa et al., “Creative synthesis of novel vitamin D analogs for health and disease,” Journal of Steroid Biochemistry and Molecular Biology, vol. 103, no. 3-5, pp. 269–276, 2007. View at Publisher · View at Google Scholar · View at PubMed
  37. A. Toyoda, H. Nagai, T. Yamada et al., “Novel synthesis of 1α,25-dihydroxy-19-norvitamin D from 25-hydroxyvitamin D,” Tetrahedron, vol. 65, no. 48, pp. 10002–10008, 2009. View at Publisher · View at Google Scholar
  38. T. Hanazawa, T. Wada, T. Masuda, S. Okamoto, and F. Sato, “Novel synthetic approach to 19-nor-1α,25-dihydroxyvitamin D3 and its derivatives by Suzuki-Miyaura coupling in solution and on solid support,” Organic Letters, vol. 3, no. 24, pp. 3975–3977, 2001. View at Publisher · View at Google Scholar
  39. P. Huang, K. Sabbe, M. Pottie, and M. Vandewalle, “A novel synthesis of 19-nor 1α,25-dihydroxyvitamin D3 and related analogues,” Tetrahedron Letters, vol. 36, no. 45, pp. 8299–8302, 1995. View at Publisher · View at Google Scholar
  40. M. Shimizu, Y. Miyamoto, H. Takaku et al., “2-Substituted-16-ene-22-thia-1α,25-dihydroxy-26,27-dimethyl-19-norvitamin D3 analogs: synthesis, biological evaluation, and crystal structure,” Bioorganic and Medicinal Chemistry, vol. 16, no. 14, pp. 6949–6964, 2008. View at Publisher · View at Google Scholar · View at PubMed
  41. A. Glebocka, R. R. Sicinski, L. A. Plum, M. Clagett-Dame, and H. F. DeLuca, “New 2-alkylidene 1α,25-dihydroxy-19-norvitamin D3 analogues of high intestinal activity: synthesis and biological evaluation of 2-(3-alkoxypropylidene) and 2-(3-hydroxypropylidene) derivatives,” Journal of Medicinal Chemistry, vol. 49, no. 10, pp. 2909–2920, 2006. View at Publisher · View at Google Scholar · View at PubMed
  42. K. L. Perlman, R. E. Swenson, H. E. Paaren, H. K. Schnoes, and H. F. DeLuca, “Novel synthesis of 19-nor-vitamin D compounds,” Tetrahedron Letters, vol. 32, no. 52, pp. 7663–7666, 1991. View at Publisher · View at Google Scholar
  43. N. Saito, S. Honzawa, and A. Kittaka, “Recent results on A-ring modification of 1α,25-dihydroxyvitamin D3: design and synthesis of VDR-agonists and antagonists with high biological activity,” Current Topics in Medicinal Chemistry, vol. 6, no. 12, pp. 1273–1288, 2006. View at Publisher · View at Google Scholar
  44. N. Saito, Y. Suhara, M. Kurihara et al., “Design and efficient synthesis of 2α-(ω-hydroxyalkoxy)- 1α,25-dihydroxyvitamin D3 analogues, including 2-epi-ED-71 and their 20-epimers with HL-60 cell differentiation activity,” Journal of Organic Chemistry, vol. 69, no. 22, pp. 7463–7471, 2004. View at Publisher · View at Google Scholar · View at PubMed
  45. E. Takahashi, K. Nakagawa, Y. Suhara et al., “Biological activities of 2α-substituted analogues of 1α,25-dihydroxyvitamin D3 in transcriptional regulation and human promyelocytic leukemia (HL-60) cell proliferation and differentiation,” Biological and Pharmaceutical Bulletin, vol. 29, no. 11, pp. 2246–2250, 2006. View at Publisher · View at Google Scholar
  46. N. Saito, T. Matsunaga, H. Saito et al., “Further synthetic and biological studies on vitamin D hormone antagonists based on C24-alkylation and C2α-functionalization of 25-dehydro-1α- hydroxyvitamin D3-26,23-lactones,” Journal of Medicinal Chemistry, vol. 49, no. 24, pp. 7063–7075, 2006. View at Publisher · View at Google Scholar · View at PubMed
  47. S. Hourai, T. Fujishima, A. Kittaka et al., “Probing a water channel near the A-ring of receptor-bound 1α,25-dihydroxyvitamin D3 with selected 2α-substituted analogues,” Journal of Medicinal Chemistry, vol. 49, no. 17, pp. 5199–5205, 2006. View at Publisher · View at Google Scholar · View at PubMed
  48. A. Yoshida, K. Ono, Y. Suhara, N. Saito, H. Takayama, and A. Kittaka, “Efficient and convergent coupling route for the short-step synthesis of enantiopure 2α- and 2β-alkylated 1α,25-dihydroxy-19-norvitamin D3 analogues,” Synlett, no. 8, pp. 1175–1179, 2003. View at Google Scholar
  49. M. A. Arai and A. Kittaka, “Novel 2-alkyl-1α,25-dihydroxy-19-norvitamin D3: efficient synthesis with Julia olefination, evaluation of biological activity and development of new analyzing system for co-activator recruitment,” Anticancer Research, vol. 26, no. 4, pp. 2621–2631, 2006. View at Google Scholar
  50. M. A. Arai, K. I. Takeyama, S. Ito, S. Kato, T. C. Chen, and A. Kittaka, “High-throughput system for analyzing ligand-induced cofactor recruitment by vitamin D receptor,” Bioconjugate Chemistry, vol. 18, no. 3, pp. 614–620, 2007. View at Publisher · View at Google Scholar · View at PubMed
  51. T. C. Chen, G. G. Schwartz, K. L. Burnstein, B. L. Lokeshwar, and M. F. Holick, “The in vitro evaluation of 25-hydroxyvitamin D3 and 19-nor-1α,25- dihydroxyvitamin D2 as therapeutic agents for prostate cancer,” Clinical Cancer Research, vol. 6, no. 3, pp. 901–908, 2000. View at Google Scholar
  52. T. C. Chen, M. F. Holick, B. L. Lokeshwar, K. L. Burnstein, and G. G. Schwartz, “Evaluation of vitamin D analogs as therapeutic agents for prostate cancer. Recent results in cancer research,” in Vitamin D Analogs in Cancer Prevention and Therapy, J. Reichrath, M. Friedrich, and W. Tilgen, Eds., vol. 164, pp. 273–288, Springer, Berlin, Germany, 2003. View at Google Scholar
  53. T. C. Chen, K. S. Persons, S. Zheng et al., “Evaluation of C-2-substituted 19-nor-1α,25-dihydroxyvitamin D3 analogs as therapeutic agents for prostate cancer,” Journal of Steroid Biochemistry and Molecular Biology, vol. 103, no. 3-5, pp. 717–720, 2007. View at Publisher · View at Google Scholar · View at PubMed
  54. J. N. Flanagan, S. Zheng, K. C. Chiang et al., “Evaluation of 19-nor-2α(3-hydroxypropyl)-1α,25-dihydroxyvitamin D3 as a therapeutic agent for androgen-dependent prostate cancer,” Anticancer Research, vol. 29, no. 9, pp. 3547–3553, 2009. View at Google Scholar
  55. Y. Ohyama, K. Ozono, M. Uchida et al., “Identification of a vitamin D-responsive element in the 5-flanking region of the rat 25-hydroxyvitamin D3 24-hydroxylase gene,” Journal of Biological Chemistry, vol. 269, no. 14, pp. 10545–10550, 1994. View at Google Scholar
  56. J. N. Flanagan, M. V. Young, K. S. Persons et al., “Vitamin D metabolism in human prostate cells: implications for prostate cancer chemoprevention by vitamin D,” Anticancer Research, vol. 26, no. 4, pp. 2567–2572, 2006. View at Google Scholar
  57. I. Schuster, “Cytochromes P450 are essential players in the vitamin D signaling system,” Biochimica et Biophysica Acta, vol. 1814, no. 1, pp. 186–199, 2011. View at Publisher · View at Google Scholar · View at PubMed
  58. D. Abe, T. Sakaki, T. Kusudo et al., “Metabolism of 2α-propoxy-1α,25-dihydroxyvitamin D3 and 2α-(3-hydroxypropoxy)-1α,25-dihydroxyvitamin D3 by human CYP27A1 and CYP24A1,” Drug Metabolism and Disposition, vol. 33, no. 6, pp. 778–784, 2005. View at Publisher · View at Google Scholar · View at PubMed
  59. E. J. Bernhard, S. B. Gruber, and R. J. Muschel, “Direct evidence linking expression of matrix metalloproteinase 9 (92-kDa gelatinase/collagenase) to the metastatic phenotype in transformed rat embryo cells,” Proceedings of the National Academy of Sciences of the United States of America, vol. 91, no. 10, pp. 4293–4297, 1994. View at Google Scholar
  60. B. Y. Bao, S. D. Yeh, and Y. F. Lee, “1α,25-dihydroxyvitamin D3 inhibits prostate cancer cell invasion via modulation of selective proteases,” Carcinogenesis, vol. 27, no. 1, pp. 32–42, 2006. View at Publisher · View at Google Scholar · View at PubMed
  61. P. Polly, M. Herdick, U. Moehren, A. Baniahmad, T. Heinzel, and C. Carlberg, “VDR-Alien: a novel, DNA-selective vitamin D3 receptorcorepressor partnership,” FASEB Journal, vol. 14, no. 10, pp. 1455–1463, 2000. View at Google Scholar