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Volumn 5, Issue 4, 2013, Pages 1355-1378

Synthesis and Biological Activity of Diastereomeric and Geometric Analogs of Calcipotriol, PRI-2202 and PRI-2205, Against Human HL-60 Leukemia and MCF-7 Breast Cancer Cells

Author keywords

Antiproliferative activity; Calcipotriol; Cancer; Combined treatment; Convergent synthesis; VDR; Vitamin D analogs

Indexed keywords


EID: 84906088077     PISSN: None     EISSN: 20726694     Source Type: Journal    
DOI: 10.3390/cancers5041355     Document Type: Article
Times cited : (24)

References (45)
  • 2
    • 79960653201 scopus 로고    scopus 로고
    • Vitamin D and cancer: Deciphering the truth
    • Mocellin, S. Vitamin D and cancer: Deciphering the truth. Biochim. Biophys. Acta 2011, 1816, 172–178.
    • (2011) Biochim. Biophys. Acta , vol.1816 , pp. 172-178
    • Mocellin, S.1
  • 3
    • 84861982740 scopus 로고    scopus 로고
    • Vitamin D and the mammary gland: A REVIEW on its role in normal development and breast cancer
    • Lopes, N.; Paredes, J.; Costa, J.L.; Ylstra, B.; Schmitt, F. Vitamin D and the mammary gland: A REVIEW on its role in normal development and breast cancer. Breast Cancer Res. 2012, 14, doi:10.1186/bcr3178.
    • (2012) Breast Cancer Res , vol.14
    • Lopes, N.1    Paredes, J.2    Costa, J.L.3    Ylstra, B.4    Schmitt, F.5
  • 6
    • 0027449050 scopus 로고
    • Vitamin D-influenced gene expression via a ligand-independent, receptor-DNA complex intermediate
    • Ross, T.K.; Darwish, H.M.; Moss, V.E.; DeLuca, H.F. Vitamin D-influenced gene expression via a ligand-independent, receptor-DNA complex intermediate. Proc. Natl. Acad. Sci. USA 1993, 15, 9257–9260.
    • (1993) Proc. Natl. Acad. Sci. USA , vol.15 , pp. 9257-9260
    • Ross, T.K.1    Darwish, H.M.2    Moss, V.E.3    DeLuca, H.F.4
  • 7
    • 44349182071 scopus 로고    scopus 로고
    • Vitamin D-dependent recruitment of corepressors to vitamin D/retinoid X receptor heterodimers
    • Sánchez-Martínez, R.; Zambrano, A.; Castillo, A.I.; Aranda, A. Vitamin D-dependent recruitment of corepressors to vitamin D/retinoid X receptor heterodimers. Mol. Cell Biol. 2008, 28, 3817–329.
    • (2008) Mol. Cell Biol , vol.28 , pp. 3817-329
    • Sánchez-Martínez, R.1    Zambrano, A.2    Castillo, A.I.3    Aranda, A.4
  • 9
    • 0033935565 scopus 로고    scopus 로고
    • Immunochemical studies on the putative plasmalemmal receptor for 1, 25(OH)(2)D(3). I. Chick intestine
    • Nemere, I.; Ray, R.; McManus, W. Immunochemical studies on the putative plasmalemmal receptor for 1, 25(OH)(2)D(3). I. Chick intestine. Am. J. Physiol. Endocrinol. Metab. 2000, 278, E1104–E1114.
    • (2000) Am. J. Physiol. Endocrinol. Metab , vol.278 , pp. E1104-E1114
    • Nemere, I.1    Ray, R.2    McManus, W.3
  • 10
    • 77950629508 scopus 로고    scopus 로고
    • Nuclear translocation of the 1,25D3-MARRS (membrane associated rapid response to steroids) receptor protein and NFkappaB in differentiating NB4 leukemia cells
    • Wu, W.; Beilhartz, G.; Roy, Y.; Richard, C.L.; Curtin, M.; Brown, L.; Cadieux, D.; Coppolino, M.; Farach-Carson, M.C.; Nemere, I.; et al. Nuclear translocation of the 1,25D3-MARRS (membrane associated rapid response to steroids) receptor protein and NFkappaB in differentiating NB4 leukemia cells. Exp. Cell Res. 2010, 316, 1101–1108.
    • (2010) Exp. Cell Res , vol.316 , pp. 1101-1108
    • Wu, W.1    Beilhartz, G.2    Roy, Y.3    Richard, C.L.4    Curtin, M.5    Brown, L.6    Cadieux, D.7    Coppolino, M.8    Farach-Carson, M.C.9    Nemere, I.10
  • 11
    • 84883386049 scopus 로고    scopus 로고
    • Plasma membrane Pdia3 and VDR interact to elicit rapid responses to 1α,25(OH)2D3
    • Chen, J.; Doroudi, M.; Cheung, J.; Grozier, A.L.; Schwartz, Z.; Boyan, B.D. Plasma membrane Pdia3 and VDR interact to elicit rapid responses to 1α,25(OH)2D3. Cell. Signal. 2013, 27, 2362–2373.
    • (2013) Cell. Signal , vol.27 , pp. 2362-2373
    • Chen, J.1    Doroudi, M.2    Cheung, J.3    Grozier, A.L.4    Schwartz, Z.5    Boyan, B.D.6
  • 13
    • 0035996631 scopus 로고    scopus 로고
    • Synthesis and antiproliferative activity of side-chain unsaturated and homologated analogs of 1,25-dihydroxyvitamin D(2). (24E)-(1S)-24-Dehydro-24a-homo-1,25-dihydroxyergocalciferol and congeners
    • Chodynski, M.; Wietrzyk, J.; Marcinkowska, E.; Opolski, A.; Szelejewski, W.; Kutner, A. Synthesis and antiproliferative activity of side-chain unsaturated and homologated analogs of 1,25-dihydroxyvitamin D(2). (24E)-(1S)-24-Dehydro-24a-homo-1,25-dihydroxyergocalciferol and congeners. Steroids 2002, 67, 789–798.
    • (2002) Steroids , vol.67 , pp. 789-798
    • Chodynski, M.1    Wietrzyk, J.2    Marcinkowska, E.3    Opolski, A.4    Szelejewski, W.5    Kutner, A.6
  • 15
    • 38949187926 scopus 로고    scopus 로고
    • The effect of combined treatment on head and neck human cancer cell lines with novel analogs of calcitriol and cytostatics
    • Wietrzyk, J.; Milczarek, M.; Kutner, A. The effect of combined treatment on head and neck human cancer cell lines with novel analogs of calcitriol and cytostatics. Oncol. Res. 2007, 16, 517–525.
    • (2007) Oncol. Res , vol.16 , pp. 517-525
    • Wietrzyk, J.1    Milczarek, M.2    Kutner, A.3
  • 16
    • 49749135218 scopus 로고    scopus 로고
    • Toxicity and antitumor activity of the vitamin D analogs PRI-1906 and PRI-1907 in combined treatment with cyclophosphamide in a mouse mammary cancer model
    • Wietrzyk, J.; Nevozhay, D.; Milczarek, M.; Filip, B.; Kutner, A. Toxicity and antitumor activity of the vitamin D analogs PRI-1906 and PRI-1907 in combined treatment with cyclophosphamide in a mouse mammary cancer model. Cancer Chemother. Pharmacol. 2008, 62, 787–797.
    • (2008) Cancer Chemother. Pharmacol , vol.62 , pp. 787-797
    • Wietrzyk, J.1    Nevozhay, D.2    Milczarek, M.3    Filip, B.4    Kutner, A.5
  • 19
    • 0033566941 scopus 로고    scopus 로고
    • 5,6-trans-16-ene-vitamin D3: A new class of potent inhibitors of proliferation of prostate, breast, and myeloid leukemic cells
    • Hisatake, J.; Kubota, T.; Hisatake, Y.; Uskokovic, M.; Tomoyasu, S.; Koeffler, H.P. 5,6-trans-16-ene-vitamin D3: A new class of potent inhibitors of proliferation of prostate, breast, and myeloid leukemic cells. Cancer Res. 1999, 59, 4023–4029.
    • (1999) Cancer Res , vol.59 , pp. 4023-4029
    • Hisatake, J.1    Kubota, T.2    Hisatake, Y.3    Uskokovic, M.4    Tomoyasu, S.5    Koeffler, H.P.6
  • 20
    • 0018132317 scopus 로고
    • Studies on the mode of action of vitamin D—XIV. Quantitative assessment of the structural requirements for the interaction of 1 alpha, 25-dihydroxyvitamin D3 with its chick intestinal mucosa receptor system
    • Wecksler, W.R.; Okamura, W.H.; Norman, A.W. Studies on the mode of action of vitamin D—XIV. Quantitative assessment of the structural requirements for the interaction of 1 alpha, 25-dihydroxyvitamin D3 with its chick intestinal mucosa receptor system. J. Steroid Biochem. 1978, 9, 929–937.
    • (1978) J. Steroid Biochem , vol.9 , pp. 929-937
    • Wecksler, W.R.1    Okamura, W.H.2    Norman, A.W.3
  • 22
    • 33745505524 scopus 로고    scopus 로고
    • Convergent synthesis of vitamin D analogs (Konwergentna synteza analogów witamin D)
    • Kutner, A. Convergent synthesis of vitamin D analogs (Konwergentna synteza analogów witamin D). Przemysł Chemiczny 2006, 85, 322–329.
    • (2006) Przemysł Chemiczny , vol.85 , pp. 322-329
    • Kutner, A.1
  • 25
    • 0035924933 scopus 로고    scopus 로고
    • Novel versatile approach to an enantiopure 19-nor, des-C,D vitamin D3 derivative
    • Hilpert, H.; Wirz, B. Novel versatile approach to an enantiopure 19-nor, des-C,D vitamin D3 derivative. Tetrahedron 2001, 57, 681–694.
    • (2001) Tetrahedron , vol.57 , pp. 681-694
    • Hilpert, H.1    Wirz, B.2
  • 28
    • 0033557922 scopus 로고    scopus 로고
    • 1,25-Dihydroxyvitamin D3 enhances the susceptibility of breast cancer cells to doxorubicin-induced oxidative damage
    • Ravid, A.; Rocker, D.; Machlenkin, A.; Rotem, C.; Hochman, A.; Kessler-Icekson, G.; Liberman, U.A.; Koren, R. 1,25-Dihydroxyvitamin D3 enhances the susceptibility of breast cancer cells to doxorubicin-induced oxidative damage. Cancer Res. 1999, 59, 862–867.
    • (1999) Cancer Res , vol.59 , pp. 862-867
    • Ravid, A.1    Rocker, D.2    Machlenkin, A.3    Rotem, C.4    Hochman, A.5    Kessler-Icekson, G.6    Liberman, U.A.7    Koren, R.8
  • 29
    • 0035145803 scopus 로고    scopus 로고
    • Activation of extracellular signal-regulated kinases (ERKs) defines the first phase of 1,25-dihydroxyvitamin D3-induced differentiation of HL60 cells
    • Wang, X.; Studzinski, G.P. Activation of extracellular signal-regulated kinases (ERKs) defines the first phase of 1,25-dihydroxyvitamin D3-induced differentiation of HL60 cells. J. Cell Biochem. 2001, 80, 471–482.
    • (2001) J. Cell Biochem , vol.80 , pp. 471-482
    • Wang, X.1    Studzinski, G.P.2
  • 31
    • 35348963580 scopus 로고    scopus 로고
    • The antitumor effect of lowered doses of cytostatics combined with new analogs of vitamin D in mice
    • Wietrzyk, J.; Nevozhay, D.; Filip, B.; Milczarek, M.; Kutner, A. The antitumor effect of lowered doses of cytostatics combined with new analogs of vitamin D in mice. Anticancer Res. 2007, 27, 3387–3398.
    • (2007) Anticancer Res , vol.27 , pp. 3387-3398
    • Wietrzyk, J.1    Nevozhay, D.2    Filip, B.3    Milczarek, M.4    Kutner, A.5
  • 32
    • 85126120353 scopus 로고    scopus 로고
    • The Scripps Research Institute: La Jolla, CA, USA
    • Trotter, J. WinMDI Version 2.9. The Scripps Research Institute: La Jolla, CA, USA, 2000.
    • (2000) WinMDI Version 2.9
    • Trotter, J.1
  • 33
    • 11144334613 scopus 로고    scopus 로고
    • Side-chain-modified analogs of calcitriol cause resistance of human HL-60 promyelocytic leukemia cells to drug-induced apoptosis
    • Chrobak, A.; Radzikowski, C.; Opolski, A. Side-chain-modified analogs of calcitriol cause resistance of human HL-60 promyelocytic leukemia cells to drug-induced apoptosis. Steroids 2005, 70, 19–27.
    • (2005) Steroids , vol.70 , pp. 19-27
    • Chrobak, A.1    Radzikowski, C.2    Opolski, A.3
  • 34
    • 0028013219 scopus 로고
    • Altered susceptibility of differentiating HL-60 cells to apoptosis induced by antitumor drugs
    • Del Bino, G.; Li, X.; Traganos, F.; Darzynkiewicz, Z. Altered susceptibility of differentiating HL-60 cells to apoptosis induced by antitumor drugs. Leukemia 1994, 8, 281–288.
    • (1994) Leukemia , vol.8 , pp. 281-288
    • Del Bino, G.1    Li, X.2    Traganos, F.3    Darzynkiewicz, Z.4
  • 35
    • 0032056362 scopus 로고    scopus 로고
    • 1Alpha,25-dihydroxyvitamin D3 inhibits programmed cell death in HL-60 cells by activation of sphingosine kinase
    • Kleuser, B.; Cuvillier, O.; Spiegel, S. 1Alpha,25-dihydroxyvitamin D3 inhibits programmed cell death in HL-60 cells by activation of sphingosine kinase. Cancer Res. 1998, 58, 1817–1824.
    • (1998) Cancer Res , vol.58 , pp. 1817-1824
    • Kleuser, B.1    Cuvillier, O.2    Spiegel, S.3
  • 36
    • 0031586330 scopus 로고    scopus 로고
    • Antiapoptotic action of 1,25-dihydroxyvitamin D3 is associated with increased mitochondrial MCL-1 and RAF-1 proteins and reduced release of cytochrome C
    • Wang, X.; Studzinski, G.P. Antiapoptotic action of 1,25-dihydroxyvitamin D3 is associated with increased mitochondrial MCL-1 and RAF-1 proteins and reduced release of cytochrome C. Exp. Cell Res. 1997, 235, 210–217.
    • (1997) Exp. Cell Res , vol.235 , pp. 210-217
    • Wang, X.1    Studzinski, G.P.2
  • 37
    • 0034902292 scopus 로고    scopus 로고
    • Potentiation of the antiproliferative effect in vitro of doxorubicin, cisplatin and genistein by new analogues of vitamin D
    • Siwinska, A.; Opolski, A.; Chrobak, A.; Wietrzyk, J.; Wojdat, E.; Kutner, A.; Szelejewski, W.; Radzikowski, C. Potentiation of the antiproliferative effect in vitro of doxorubicin, cisplatin and genistein by new analogues of vitamin D. Anticancer Res. 2001, 21, 1925–1929.
    • (2001) Anticancer Res , vol.21 , pp. 1925-1929
    • Siwinska, A.1    Opolski, A.2    Chrobak, A.3    Wietrzyk, J.4    Wojdat, E.5    Kutner, A.6    Szelejewski, W.7    Radzikowski, C.8
  • 38
    • 82555197933 scopus 로고    scopus 로고
    • The in-vitro antiproliferative effect of PRI-2191 and imatinib applied in combined treatment with cisplatin, idarubicin, or docetaxel on human leukemia cells
    • Switalska, M.; Nasulewicz-Goldeman, A.; Opolska, A.; Maciejewska, M.; Kutner, A.; Wietrzyk, J. The in-vitro antiproliferative effect of PRI-2191 and imatinib applied in combined treatment with cisplatin, idarubicin, or docetaxel on human leukemia cells. Anticancer Drugs 2012, 23, 70–80.
    • (2012) Anticancer Drugs , vol.23 , pp. 70-80
    • Switalska, M.1    Nasulewicz-Goldeman, A.2    Opolska, A.3    Maciejewska, M.4    Kutner, A.5    Wietrzyk, J.6
  • 39
    • 84879045910 scopus 로고    scopus 로고
    • Vitamin D analogs enhance the anticancer activity of 5-fluorouracil in an in vivo mouse colon cancer model
    • Milczarek, M.; Psurski, M.; Kutner, A.; Wietrzyk, J. Vitamin D analogs enhance the anticancer activity of 5-fluorouracil in an in vivo mouse colon cancer model. BMC Cancer 2013, 13, doi:10.1186/1471-2407-13-294.
    • (2013) BMC Cancer , vol.13
    • Milczarek, M.1    Psurski, M.2    Kutner, A.3    Wietrzyk, J.4
  • 40
    • 0027195046 scopus 로고
    • Sex steroids induced up-regulation of 1,25-(OH)2 vitamin D3 receptors in T 47D breast cancer cells
    • Escaleira, M.T.; Sonohara, S.; Brentani, M.M. Sex steroids induced up-regulation of 1,25-(OH)2 vitamin D3 receptors in T 47D breast cancer cells. J. Steroid Biochem. Mol. Biol. 1993, 45, 257–263.
    • (1993) J. Steroid Biochem. Mol. Biol , vol.45 , pp. 257-263
    • Escaleira, M.T.1    Sonohara, S.2    Brentani, M.M.3
  • 41
    • 0027276092 scopus 로고
    • Antitumor effect of 22-oxa-calcitriol, a noncalcemic analogue of calcitriol, in athymic mice implanted with human breast carcinoma and its synergism with tamoxifen
    • Abe-Hashimoto, J.; Kikuchi, T.; Matsumoto, T.; Nishii, Y.; Ogata, E.; Ikeda, K. Antitumor effect of 22-oxa-calcitriol, a noncalcemic analogue of calcitriol, in athymic mice implanted with human breast carcinoma and its synergism with tamoxifen. Cancer Res. 1993, 53, 2534–2537.
    • (1993) Cancer Res , vol.53 , pp. 2534-2537
    • Abe-Hashimoto, J.1    Kikuchi, T.2    Matsumoto, T.3    Nishii, Y.4    Ogata, E.5    Ikeda, K.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.