Deoxybenzoins are novel potent selective estrogen receptor modulators

Steroids

Volumn 72, Issue 9-10, 2007, Pages 693-704

  Papoutsi, Zoi ^a   Kassi, Eva ^a   Fokialakis, Nikolas ^b   Mitakou, Sofia ^b   Lambrinidis, George ^b   Mikros, Emmanuel ^b   Moutsatsou, Paraskevi ^a  

^a UNIVERSITY OF ATHENS MEDICAL SCHOOL   (Greece)

^b UNIVERSITY OF ATHENS   (Greece)

Author keywords

Breast cancer cells; Deoxybenzoins; Estrogen receptor; IGFBP 3; Osteoblasts; Selective estrogen receptor modulator (SERM)

Indexed keywords

CONNECTIVE TISSUE GROWTH FACTOR; DEOXYBENZOIN DERIVATIVE; ESTRADIOL; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; PROTEIN P52; RECEPTOR SUBTYPE; SELECTIVE ESTROGEN RECEPTOR MODULATOR; UNCLASSIFIED DRUG;

ARTICLE; CANCER CELL CULTURE; CELL VIABILITY; CONTROLLED STUDY; DRUG POTENCY; DRUG SELECTIVITY; HELA CELL; HORMONE SUBSTITUTION; HUMAN; HUMAN CELL; MINERALIZATION; MOLECULAR MODEL; OSTEOBLAST; REPORTER GENE;

BENZOIN; CALCIFICATION, PHYSIOLOGIC; CELL LINE, TUMOR; CELL SURVIVAL; ESTRADIOL; ESTROGEN ANTAGONISTS; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; ESTROGENS; FEMALE; GROWTH INHIBITORS; HUMANS; INSULIN-LIKE GROWTH FACTOR BINDING PROTEIN 3; MONTE CARLO METHOD; OSTEOBLASTS; PHYTOESTROGENS; SELECTIVE ESTROGEN RECEPTOR MODULATORS; TUMOR SUPPRESSOR PROTEINS;

EID: 34547198324     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2007.05.010     Document Type: Article

References (55)

1. Middleton Jr. E., Kandaswami C., and Theoharides T.C. The effects of plant flavonoids on mammalian cells: implications for inflammation, heart disease, and cancer. Pharmacol Rev 52 4 (2000) 673-751
2. Lissin L.W., and Cooke J.P. Phytoestrogens and cardiovascular health. J Am Coll Cardiol 35 6 (2000) 1403-1410
3. Ewies A.A. Phytoestrogens in the management of the menopause: up-to-date. Obstet Gynecol Surv 57 5 (2002) 306-313
4. Finkel E. Phyto-estrogens: the way to postmenopausal health?. Lancet 352 9142 (1998) 1762
5. Newbold R.R., Banks E.P., Bullock B., and Jefferson W.N. Uterine adenocarcinoma in mice treated neonatally with genistein. Cancer Res 61 11 (2001) 4325-4328
6. Hilaviki-Clarke L., Cho E., Onojafe I., Raygada M., and Clarke R. Maternal exposure to genistein during pregnancy increases carcinogen-induced mammary tumorigenesis in female rat offspring. Oncol Rep 6 5 (1999) 1089-1095
7. Allred C.D., Ju Y.H., Allred K.F., Chang J., and Helferich W.G. Dietary genistin stimulates growth of estrogen-dependent breast cancer tumors similar to that observed with genistein. Carcinogenesis 22 10 (2001) 1667-1673
8. Petrakis N.L., Barnes S., King E.B., Lowenstein J., Wiencke J., Lee M.M., et al. Stimulatory influence of soy protein isolate on breast secretion in pre-and postmenopausal women. Cancer Epidemiol Biomarkers Prev 5 10 (1996) 785-794
9. Nilsson S., Makela S., Treuter E., Tujague M., Thomsen J., Andersson G., et al. Mechanisms of estrogen action. Physiol Rev 81 4 (2001) 1535-1565
10. Weihua Z., Andersson S., Cheng G., Simpson E.R., Warner M., and Gustafsson J.A. Update on estrogen signalling. FEBS Lett 546 1 (2003) 17-24
11. Barkhem T., Carlsson B., Nilsson Y., Enmark E., Gustafsson J.A., and Nilsson S. Differential response of estrogen receptor alpha and estrogen receptor beta to partial estrogen agonists/antagonists. Mol Pharmacol 54 1 (1998) 105-112
12. Kuiper G.G., Lemmen J.G., Carlsson B., Corton J.C., Safe S.H., van der Saag P.T., et al. Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta. Endocrinology 139 10 (1998) 4252-4263
13. Mueller S.O., Simon S., Chae K., Metzler M., and Korach K.S. Phytoestrogens and their human metabolites show distinct agonistic and antagonistic properties on estrogen receptor α (ERα) and ERβ in human cells. Toxicol Sci 80 1 (2004) 14-25
14. Papoutsi Z., Kassi E., Mitakou S., Aligiannis N., Tsiapara A., Chrousos G.P., et al. Acteoside and martynoside exhibit estrogenic/antiestrogenic properties. J Steroid Biochem Mol Biol 98 1 (2006) 63-71
15. Papoutsi Z., Kassi E., Tsiapara A., Fokialakis N., Chrousos G.P., and Moutsatsou P. Evaluation of estrogenic/antiestrogenic activity of ellagic acid via the estrogen receptor subtypes ERα and ERβ. J Agric Food Chem 53 20 (2005) 7715-7720
16. Sanduja R., Weinheimer A.J., and Alam M. Albizoin: isolation and structure of a deoxybenzoin from the marine mollusk Nerita albicilla. J Chem Res Synop (1985) 56-57
17. Kiuchi F., Chen X., and Tsuda Y. Four new phenolic constituents from Licorise (root of Glycyrrhiza sp.). Heterocycles 31 (1990) 629-636
18. Niwa K., Hashimoto M., Morishita S., Yokoyama Y., Mori H., and Tamaya T. Preventive effects of Glycyrrhizae radix extract on estrogen-related endometrial carcinogenesis in mice. J Cancer Res 90 7 (1999) 726-732
19. Wahala K., and Hase T.A. Expedient synthesis of polyhydroxyisoflavonoids. J Chem Soc Perkin Trans 1 1 (1991) 3005-3008
20. Balasubramanian S., and Nair M.G. An efficient "one pot" synthesis of isoflavones. Synthetic Commun 30 (2000) 469-484
21. Fokialakis N., Lambrinidis G., Mitsiou D.J., Aligiannis N., Mitakou S., Skaltsounis L.A., et al. A new class of phytoestrogens: evaluation of the estrogenic activity of deoxybenzoins. Chem Biol 11 3 (2004) 397-406
22. Papoutsi Z., Kassi E., Papaevangeliou D., Pratsinis H., Zoumpourlis V., Halabalaki M., et al. Plant 2-arylobenzofurans demonstrate a selective estrogen receptor modulator profile. Steroids 69 11/12 (2004) 727-734
23. Kassi E., Papoutsi Z., Fokialakis N., Messari I., Mitakou S., and Moutsatsou P. Greek plant extracts exhibit selective estrogen receptor modulator (SERM)-like properties. J Agric Food Chem 52 23 (2004) 6956-6961
24. Stauffer S.R., Coletta C.J., Tedesco R., Nishigushi G., Carlson K., Sun J., et al. Pyrazole ligands: structure affinity/activity relationships and estrogen receptor-α-selective agonists. J Med Chem 43 26 (2000) 4934-4947
25. Meyers M.J., Sun J., Carlson K.E., Gwendolyn A.M., Katzenellenbogen B.S., and Katzenellenbogen J.A. Estrogen receptor-β potency-selective ligands: structure-activity relationship studies of diarylpropionitriles and their acetylene and polar analogues. J Med Chem 44 24 (2001) 4230-4251
26. Denizot F., and Lang R. Rapid colorimetric assay for cell growth and survival: modifications to the tetrozolium dye procedure giving improved sensitivity and reliability. J Immunol Methods 89 2 (1986) 271-277
27. Dang Z.C., van Bezooijen R.L., Karperien M., Papapoulos S.E., and Lowik C.W.G.M. Exposure of KS483 cells to estrogen enhances osteogenesis and inhibits adipogenesis. J Bone Miner Res 17 3 (2002) 394-405
28. Mohamadi F., Richards N.G.J., Guida W.C., Liskamp R., Caufield C., Chang G., et al. Macromodel-an integrated software system for modeling organic and bioorganic molecules using molecular mechanics. J Comput Chem 11 (1990) 440-467
29. Shiau A.K., Barstad D., Loria P.M., Cheng L., Kushner P.J., Agard D.A., et al. The structural basis of estrogen receptor/coactivator recognition and the antagonism of this interaction by tamoxifen. Cell 95 7 (1998) 927-937
30. Pike A.C.W., Brzozowski A.M., Hubbard R.E., Bonn T., Thorsell A.G., Engstrom O., et al. Structure of the ligand-binding domain of oestrogen receptor beta in the presence of a partial agonist and a full antagonist. EMBO J 18 17 (1999) 4608-4618
31. Brzozowski A.M., Pike A.C., Dauter Z., Hubbard R.E., Bonn T., Engstrom O., et al. Molecular basis of agonism and antagonism in oestrogen receptor. Nature 389 6652 (1997) 753-758
32. Gangloff M., Ruff M., Eiler S., Duclaud S., Wurtz J.M., and Moras D. Crystal structure of a mutant hERalpha ligand-binding domain reveals key structural features for the mechanism of partial agonism. J Biol Chem 276 18 (2001) 15059-15065
33. Diel P., Smolnikar K., and Michna H. In vitro test systems for the evaluation of the estrogenic activity of natural products. Planta Med 65 3 (1999) 197-203
34. Fürstenberger G., and Sonn H.-J. Insulin-like growth factors and cancer. Lancet Oncol 3 5 (2002) 298-302
35. Pratt S.E., and Pollak M.N. Estrogen and antiestrogen modulation of MCF7 human breast cancer cell proliferation is associated with specific alterations in accumulation of insulin-like growth factor binding proteins in conditioned media. Cancer Res 53 21 (1993) 5193-5198
36. Huynh H., Yang X., and Pollak M. Estradiol and antiestrogens regulate a growth inhibitory insulin-like growth factor binding protein 3 autocrine loop in human breast cancer cells. J Biol Chem 271 2 (1996) 1016-1021
37. Wang T.T., Sathyamoorthy N., and Phang J.M. Molecular effects of genistein on estrogen receptor mediated pathways. Carcinogenesis 17 2 (1996) 271-275
38. Maggliolini M., Sratti G., Vivacqua A., Gabriele S., Rago V., Loizzo M., et al. Estrogenic and antiproliferative activities of isoliquiritigenin in MCF-7 breast cancer cells. J Steroid Biochem Mol Biol 82 4/5 (2002) 315-322
39. Read L.D., Greene G.L., and Katzenellenbogen B.S. Regulation of estrogen receptor messenger ribonucleic acid and protein levels in human breast cancer cell lines by sex steroid hormones, their antagonist, and growth factors. Mol Endocrinol 3 2 (1989) 295-304
40. Ise R., Han D., Takahashi Y., Terasaka S., Inoue A., Tanji M., et al. Expression profiling of the estrogen responsive genes in response to phytoestrogens using a customized DNA microarrays. FEBS Lett 579 7 (2005) 1732-1740
41. Lu C., Shen Q., Dupre E., Kim H., Hilsenbeck S., and Brown P.H. cFos is critical for MCF-7 breast cancer cell growth. Oncogene 24 43 (2005) 6516-6521
42. Maggliolini M., Bonofiglio D., Marsico S., Panno M.L., Genni B., Picard D., et al. Estrogen receptor alpha mediates the proliferative but not the cytotoxic dose-dependent effects of two major phytoestrogens on human breast cancer cells. Mol Pharmacol 60 3 (2001) 595-602
43. Benassayag C., Perrot-Applanat M., and Ferre F. Phytoestrogens as modulators of steroid action in target cells. J Chromatogr B 777 1/2 (2002) 233-248
44. Monje P., and Boland R. Expression and cellular localization of naturally occurring beta estrogen receptors in uterine and mammary cell lines. J Cell Biochem 86 1 (2002) 136-144
45. Chang E.C., Frasor J., Komm B., and Katzenellenbogen B.S. Impact of estrogen receptor beta on gene networks regulated by estrogen receptor alpha in breast cancer cells. Endocrinology 147 10 (2006) 4831-4842
46. Littlefield B.A., Gurpide E., Markiewicz L., McKinley B., and Hochberg R.B. A simple and sensitive microtiter plate estrogen bioassay based on stimulation of alkaline phosphatase in Ishikawa cells: estrogenic action of delta 5 adrenal steroids. Endocrinology 127 6 (1990) 2757-2762
47. Markiewicz L., Garey J., Adlercreutz H., and Gurpide E. In vitro bioassays of non steroidal phytoestrogens. J Steroid Biochem Mol Biol 45 5 (1993) 399-405
48. Manolagas S.C., Kousteni S., and Jilka R.L. Sex steroids and bone. Recent Prog Horm Res 57 (2002) 385-409
49. Kousteni S., Han L., Chen J.R., Almeida M., Plotkin L.I., Bellido T., et al. Kinase-mediated regulation of common transcription factors accounts for the bone-protective effects of sex steroids. J Clin Invest 111 11 (2003) 1651-1664
50. Maeda T., Matsunuma A., Kawane T., and Horiuchi N. Simvastatin promotes osteoblast differentiation and mineralization in MC3T3-E1 cells. Biochem Biophys Res Commun 280 (2001) 874-877
51. McDougal K.E., Perry M.J., Gibson R.L., Colley S.M., Korach K.S., and Tobias J.H. Estrogen receptor alpha dependency of estrogen's stimulatory action on cancellous bone formation in male mice. Endocrinology 144 5 (2003) 1994-1999
52. Deroo B.J., and Korach K.S. Estrogen receptors and human disease. J Clin Invest 116 3 (2006) 561-570
53. Lindberg M.K., Moverate S., Skrtic S., Gao H., Dahlman-Wright K., Gustafsson J.A., et al. Estrogen receptor (ER)-β reduces ERα regulated gene transcription, supporting a "Ying Yang" relationship between ERα and ERβ in mice. Mol Endocrinol 17 2 (2003) 203-208
54. Windahl S.H., Andersson G., and Gustafsson J.A. Elucidation of estrogen receptor function in bone with the use of mouse models. Trends Endocrinol Metabol 13 5 (2002) 195-200
55. Dang Z.C., Andinot V., Papapoulos S.E., Bantin J.A., and Lowik C.W.G.M. Peroxisome proliferator-activated receptor γ (PPARγ) as a molecular target for the soy phytoestrogen genistein. J Biol Chem 278 2 (2003) 962-967