QW-1624F2-2, a synthetic analogue of 1,25-dihydroxyvitamin D3, enhances the response to other deltanoids and suppresses the invasiveness of human metastatic breast tumor cells

Molecular Cancer Therapeutics

Volumn 5, Issue 11, 2006, Pages 2806-2814

  Sundaram, Sujatha ^a   Beckman, Matthew J ^c   Bajwa, Amandeep ^c   Wei, Jeffrey ^a   Smith, Kathleen M ^a   Posner, Gary H ^b   Gewirtz, David A ^d  

^a DARTMOUTH MEDICAL SCHOOL   (United States)

^b JOHNS HOPKINS UNIVERSITY   (United States)

^c VIRGINIA COMMONWEALTH UNIVERSITY   (United States)

^d VIRGINIA COMMONWEALTH UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

20 EPICALCITRIOL; CALCIUM; OXYGENASE; QW 1624F2 2; SEOCALCITOL; STEROID 24 HYDROXYLASE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST TUMOR; CALCIUM BLOOD LEVEL; CANCER INHIBITION; CANCER INVASION; CONTROLLED STUDY; DRUG POTENCY; ENZYME ACTIVATION; ENZYME INDUCTION; GENETIC TRANSCRIPTION; HUMAN; MOLECULAR STABILITY; PRIORITY JOURNAL; PROTEIN EXPRESSION; TUMOR CELL;

ANTINEOPLASTIC AGENTS; BREAST NEOPLASMS; CALCITRIOL; CELL LINE, TUMOR; CELL PROLIFERATION; DOSE-RESPONSE RELATIONSHIP, DRUG; FEMALE; HUMANS; NEOPLASM INVASIVENESS; NEOPLASM METASTASIS; PROMOTER REGIONS (GENETICS); RECEPTORS, CALCITRIOL; STEROID HYDROXYLASES;

EID: 33845204230     PISSN: 15357163     EISSN: None     Source Type: Journal    
DOI: 10.1158/1535-7163.MCT-06-0092     Document Type: Article

References (63)

1. Krishnan AV, Peehl DM, Feldman D. The role of vitamin D in prostate cancer. Recent Results Cancer Res 2003; 164:205-21.
2. Krishnan AV, Peehl DM, Feldman D. Inhibition of prostate cancer growth by vitamin D: Regulation of target gene expression. J Cell Biochem 2003;88:363-71.
3. Lin R, Nagai Y, Sladek R, et al. Expression profiling in squamous carcinoma cells reveals pleiotropic effects of vitamin D3 analog EB1089 signaling on cell proliferation, differentiation, and immune system regulation. Mol Endocrinol 2002;16:1243-56.
4. Bortman P, Folgueira MA, Katayama ML, Snitcovsky IM, Brentani MM. Antiproliferative effects of 1,25-dihydroxyvitamin D3 on breast cells: a mini review. Braz J Mad Biol Res 2002;35:1-9.
5. Hedlund TE, Moffatt KA, Miller GJ. Stable expression of the nuclear vitamin D receptor in the human prostatic carcinoma cell line JCA-1: evidence that the antiproliferative effects of 1α,25-dihydroxyvitamin D3 are mediated exclusively through the genomic signaling pathway. Endocrinology 1996;137:1554-61.
6. Kane KF, Langman MJ, Williams GR. Antiproliferative responses to two human colon cancer cell lines to vitamin D3 are differently modified by 9-cis-retinoic acid. Cancer Res 1996;56:623-32.
7. Zhao X, Feldman D. Regulation of vitamin D receptor abundance and responsiveness during differentiation of HT-29 human colon cancer cells. Endocrinology 1993;132:1808-14.
8. Kaewsakhorn T, Kisseberth WC, Capen CC, et al. Effects of calcitriol, seocalcitol, and medium-chain triglyceride on a canine transitional cell carcinoma cell line. Anticancer Res 2005;25:2689-96.
9. Sahin MO, Canda AE, Yorukoglu K, et al. 1,25 Dihydroxyvitamin D(3) receptor expression in superficial transitional cell carcinoma of the bladder: a possible prognostic factor? Eur Urol 2005;47:52-7.
10. Ohyama Y, Yamasaki T. Eight cytochrome P450s catalyze vitamin D metabolism. Front Biosci 2004;9:3007-18.
11. Avila E, Diaz L, Halhali A, Larrea F. Regulation of 25-hydroxyvitamin D3 1α-hydroxylase, 1,25-dihydroxyvitamin D3 24-hydroxylase and vitamin D receptor gene expression by 8-bromo cyclic AMP in cultured human syncytiotrophoblast cells. J Steroid Biochem Mol Biol 2004; 89-90:115-9.
12. Omdahl JL, Bobrovnikova EV, Annalora A, Chen P, Serda R. Expression, structure-function, and molecular modeling of vitamin D P450s. J Cell Biochem 2003;88:356-62.
13. Jones G, Strugnell SA, Deluca HF. Current understanding of the molecular actions of vitamin D, Physiol Rev 1998;78:1193-231.
14. Albertson DG, Ylstra B, Segraves R, et al. Quantitative mapping of amplicon structure by array CGH identifies CYP24 as a candidate oncogene. Nat Genet 2000;25:144-6.
15. Townsend K, Banwell CM, Guy M, et al. Autocrine metabolism of vitamin D in normal and malignant breast tissue. Clin Cancer Res 2005;11: 3579-86.
16. Khanim FL, Gornmersall LM, Wood VH, et al. Altered SMRT levels disrupt vitamin D3 receptor signalling in prostate cancer cells. Oncogene 2004;23:6712-25.
17. Mitschele T, Diesel B, Friedrich M, et al. Analysis of the vitamin D system in basal cell carcinomas (BCCs). Lab Invest 2004;84:693-702.
18. Mimori K, Tanaka Y, Yoshinaga K, et al. Clinical significance of the overexpression of the candidate oncogene CYP24 in esophageal cancer. Ann Oncol 2004;15:236-41.
19. Bareis P, Bises G, Bischof MG, Cross HS, Peterlik M. 25-Hydroxy-vitamin D metabolism in human colon cancer cells during tumor progression. Biochem Biophys Res Commun 2001;285:1012-7.
20. Cross HS, Kallay E, Farhan H, Weiland T, Manhardt T. Regulation of extrarenal vitamin D metabolism as a too[ for colon and prostate cancer prevention. Recent Results Cancer Res 2003;164:413-25.
21. Weiss MM, Snijders AM, Kuipers EJ, et al. Determination of amplicon boundaries at 20q13.2 in tissue samples of human gastric adenocarcinomas by high-resolution microarray comparative genomic hybridization. J Pathol 2003; 200:320-6.
22. Jones G, Ramshaw H, Zhang A, et al. Expression and activity of vitamin D-metabolizing cytochrome P450s (CYP1α and CYP24) in human nonsmall cell lung carcinomas. Endocrinology 1999;140:3303-10.
23. Hansen CM, Binderup L, Hamberg KJ, Carlberg C. Vitamin D and cancer: effects of 1,25(OH)2D3 and its analogues on growth control and tumorigenesis. Front Biosci 2001;6:D820-48.
24. Hansen CM, Hamberg KJ, Binderup E, Binderup L. Seocalcitol (EB 1089): a vitamin D analogue of anti-cancer potential. Background, design, synthesis, pre-clinical and clinical evaluation. Curr Pharm Des 2000;6: 803-28.
25. Peleg S, Posner GH. Vitamin D analogues as modulators of vitamin D receptor action. Curr Top Med Chem 2003;3:1555-72.
26. Posner GH, Lee JK, Wang Q, et al. Noncalcemic, antiproliferative, transcriptionally active, 24-fluorinated hybrid analogues of the hormone 1α,25-dihydroxyvitamin D3. Synthesis and preliminary biological evaluation. J Med Chem 1998;41:3008-14.
27. Dixon KM, Deo SS, Wong G, et al. Skin cancer prevention: a possible role of 1,25dihydroxyvitamin D3 and its analogs. J Steroid Biochem Mol Biol 2005;97:137-43.
28. Kensler TW, Dolan PM, Gange SJ, et al. Conceptually new deltanods (vitamin D analogs) inhibit multistage skin tumorigenesis. Carcinogenesis 2000;21:1341-5.
29. Posner GH, Wang Q, Han G, et al. Conceptually new sulfone analogues of the hormone 1α,25-dihydroxyvitamin D(3): synthesis and preliminary biological evaluation. J Mad Chem 1999;42:3425-35.
30. Zou A, Elgort MG, Allegretto EA. Retinoid X receptor (RXR) ligands activate the human 25-hydroxyvitamin D3-24-hydroxylase promoter via RXR heterodimer binding to two vitamin D-responsive elements and elicit additive effects with 1,25-dihydroxyvitamin D3. J Biol Chem 1997;272: 19027-34.
31. Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 1983;65:55-63.
32. McLeskey SW, Zhang L, Kharbanda S, et al. Fibroblast growth factor overexpressing breast carcinoma cells as models of angiogenesis and metastasis. Breast Cancer Res Treat 1996;39:103-17.
33. Zierold C, Reinholz GG, Mings JA, Prahl JIM, DeLuca HF. Regulation of the procine 1,25-dihydroxyvitamin D3-24-hydroxylase (CYP24) by 1,25-dihydroxyvitamin D3 and parathyroid hormone in AOK-B50 cells. Arch Biochem Biophys 2000;381:323-7.
34. Armbrecht HJ, Hodam TL, Boltz MA, et al. Induction of the vitamin D 24-hydroxylase (CYP24) by 1,25-dihydroxyvitamin D3 is regulated by parathyroid hormone in UMR106 osteoblastic cells. Endocrinology 1998; 139:3375-81.
35. Posner GH, Halford BA, Peleg S, Dolan P, Kensler TW. Conceptually new low-calcemic oxime analogues of the hormone 1α,25-dihydroxyvitamin D(3): synthesis and biological testing. J Med Chem 2002;45: 1723-30.
36. Chaudhry M, Sundaram S, Gennings C, Carter H, Gewirtz DA. The vitamin D3 analog, ILX-23-7553, enhances the response to Adriamycin and irradiation in MCF-7 breast tumor cells. Cancer Chemother Pharmacol 2001;47:429-36.
37. Sundaram S, Chaudhry M, Reardon D, Gupta M, Gewirtz DA. The vitamin D3 analog EB 1089 enhances the antiproliferative and apoptotic effects of Adriamycin in MCF-7 breast tumor cells. Breast Cancer Res Treat 2000;63:1-10.
38. Sundaram S, Gewirtz DA. The vitamin D3 analog EB 1089 enhances the response of human breast tumor cells to radiation. Radiat Res 1999; 152:479-86.
39. Amir H, Karas M, Giat J, et al. Lycopene and 1,25-dihydroxyvitamin D3 cooperate in the inhibition of cell cycle progression and induction of differentiation in HL-60 leukemic cells. Nutr Cancer 1999;33:105-12.
40. Banwell CM, Singh R, Stewart PM, Uskokovic MR, Campbell MJ. Antiproliferative signalling by 1,25(OH)2D3 in prostate and breast cancer is suppressed by a mechanism involving histone deacetylation. Recent Results Cancer Res 2003;164:83-98.
41. Hisatake J, O'Kelly J, Uskokovic MR, Tomoyasu S, Koeffler HP. Novel vitamin D(3) analog, 21-(3-methyl-3-hydroxy-butyl)-19-nor D(3), that modulates cell growth, differentiation, apoptosis, cell cycle, and induction of PTEN in leukemic cells. Blood 2001;97:2427-33.
42. Tanaka Y, Wu AY, Ikekawa N, et al. Inhibition of HT-29 human colon cancer growth under the renal capsule of severe combined immunodeficient mice by an analogue of 1,25-dihydroxyvitamin D3, DD-003. Cancer Res 1994;54:5148-53.
43. Smith LM, Wise SC, Hendricks DT, et al. cJun overexpression in MCF-7 breast cancer cells produces a tumorigenic, invasive and hormone resistant phenotype. Oncogene 1999; 18:6063-70.
44. Brown AJ. Therapeutic uses of vitamin D analogues. Am J Kidney Dis 2001;38:S3-19.
45. Ly LH, Zhao XY, Holloway L, Feldman D. Liarozoie acts synergistically with 1α,25-dihydroxyvitamin D3 to inhibit growth of DU 145 human prostate cancer cells by blocking 24-hydroxylase activity. Endocrinology 1999;140:2071-6.
46. Rashid SF, Moore JS, Walker E, et al. Synergistic growth inhibition of prostate cancer cells by 1α,25 dihydroxyvitamin D(3) and its 19-norhexafluoricle analogues in combination with either sodium butyrate or trichostatin A. Oncogene 2001;20:1860-72.
47. Skowronski RJ, Peehl DM, Feldman D. Vitamin D and prostate cancer: 1,25 dihydroxyvitamin D3 receptors and actions in human prostate cancer cell lines. Endocrinology 1993;132:1952-60.
48. DeLuca HF. Overview of general physiologic features and functions of vitamin D. Am J Clin Nutr 2004;80:1689-96S.
49. Zierold C, Darwish HM, DeLuca HF. Two vitamin D response elements function in the rat 1,25-dihydroxyvitamin D 24-hydroxylase promoter. J Biol Chem 1995;270:1675-8.
50. Chen KS, DeLuca HF. Cloning of the human 1α,25-dihydroxyvitamin D-3 24-hydroxylase gene promoter and identification of two vitamin D-responsive elements. Biochim Biophys Acta 1995;1263:1-9.
51. Kerry DM, Dwivedi PP, Hahn CN, et al. Transcriptional synergism between vitamin D-responsive elements in the rat 25-hydroxyvitamin D3 24-hydroxylase (CYP24) promoter. J Biol Chem 1996;271: 29715-21.
52. Yang W, Friedman PA, Kumar R, et al. Expression of 25(OH)D3 24-hydroxylase in distal nephron: coordinate regulation by 1,25(OH)2D3 and cAMP or PTH. Am J Physiol 1999;276:E793-805.
53. Zierold C, Mings JA, DeLuca HF. Regulation of 25-hydroxyvitamin D3-24-hydroxylase mRNA by 1,25-dihydroxyvitamin D3 and parathyroid hormone. J Cell Biochem 2003;88:234-7.
54. Gao XH, Dwivedi PP, Omdahl JL, Morris HA, May BK. Calcitonin stimulates expression of the rat 25-hydroxyvitamin D3-24-hydroxylase (CYP24) promoter in HEK-293 cells expressing calcitonin receptor: identification of signaling pathways. J Mol Endocrinol 2004;32:87-98.
55. Beckman MJ, DeLuca HF. Regulation of renal vitamin D receptor is an important determinant of 1α,25-dihydroxyvitamin D(3) levels in vivo. Arch Biochem Biophys 2002;401:44-52.
56. Posner GH, Jeon HB, Sarjeant A, et al. Low-calcemic, efficacious, 1α,25-dihydroxyvitamin D3 analog QW-1624F2-2: calcemic dose-response determination, preclinical genotoxicity testing, and revision of A-ring stereochemistry. Steroids 2004;69:757-62.
57. Akeno N, Saikatsu S, Kawane T, Horiuchi N. Mouse vitamin D-24-hydroxylase: molecular cloning, tissue distribution, and transcriptional regulation by 1α,25-dihydroxyvitamin D3. Endocrinology 1997;138: 2233-40.
58. Armbrecht HJ, Chen ML, Hodam TL, Boltz MA. Induction of 24-hydroxylase cytochrome P450 mRNA by 1,25-dihydroxyvitamin D and phorbol esters in normal rat kidney (NRK-52E) cells. J Endocrinol 1997; 153:199-205.
59. Armbrecht HJ, Hodam TL. Parathyroid hormone and 1,25-dihydroxyvitamin D synergistically induce the 1,25-dihydroxyvitamin D-24-hydroxylase in rat UMR-106 osteoblast-like cells. Biochem Biophys Res Commun 1994;205:674-9.
60. Armbrecht HJ, Hodam TL, Boltz MA. Hormonal regulation of 25-hydroxyvitamin D3-1α-hydroxylase and 24-hydroxylase gene transcription in opossum kidney cells. Arch Biochem Biophys 2003;409: 298-304.
61. Armbrecht HJ, Wongsurawat N, Zenser TV, Davis BB. Differential effects of parathyroid hormone on the renal 1,25-dihydroxyvitamin D3 and 24,25-dihydroxyvitamin D3 production of young and adult rats. Endocrinology 1982;111:1339-44.
62. Miettinen S, Ahonen MH, Lou YR, et al. Role of 24-hydroxylase in vitamin D3 growth response of OVCAR-3 ovarian cancer cells. Int J Cancer 2004;108:367-73.
63. Christensen GL, Jepsen JS, Fog CK, Christensen IJ, Lykkesfeldt AE. Sequential versus combined treatment of human breast cancer cells with antiestrogens and the vitamin D analogue EB1089 and evaluation of predictive markers for vitamin D treatment. Breast Cancer Res Treat 2004; 85:53-63.