Plant 2-arylobenzofurans demonstrate a selective estrogen receptor modulator profile

Steroids

Volumn 69, Issue 11-12, 2004, Pages 727-734

  Papoutsi, Zoi ^a   Kassi, Eva ^a   Papaevangeliou, Dimitra ^a,b   Pratsinis, Harris ^a   Zoumpourlis, Vassilis ^c   Halabalaki, Maria ^d   Mitakou, Sofia ^d   Kalofoutis, Anastasios ^a   Moutsatsou, Paraskevi ^a  

^a UNIVERSITY OF ATHENS MEDICAL SCHOOL   (Greece)

^b Pharmaceutical Industry   (Greece)

^c INSTITUTE OF BIOLOGY   (Greece)

^d UNIVERSITY OF ATHENS   (Greece)

Author keywords

Antiestrogen; Arylobenzofurans; Breast cancer; Mineralization; Osteoblast; Selective estrogen receptor modulators

Indexed keywords

ALIZARIN RED S; ALKALINE PHOSPHATASE; ANTIESTROGEN; BENZOFURAN DERIVATIVE; CALCIUM; CHLORAMPHENICOL ACETYLTRANSFERASE; EBENFURAN 1; EBENFURAN 2; EBENFURAN 3; ESTRADIOL; ESTROGEN; ESTROGEN RECEPTOR; FULVESTRANT; SELECTIVE ESTROGEN RECEPTOR MODULATOR; SOMATOMEDIN BINDING PROTEIN 3; UNCLASSIFIED DRUG;

ADENOCARCINOMA; ARTICLE; BONE CELL; BREAST CANCER; CALCIUM BLOOD LEVEL; CANCER CELL; CELL CULTURE; CELL DIFFERENTIATION; CELL LINE; CELL PROLIFERATION; CONTROLLED STUDY; ENZYMATIC ASSAY; ESTROGEN ACTIVITY; HELA CELL; HISTOCHEMISTRY; HUMAN; HUMAN CELL; HUMAN TISSUE; MINERALIZATION; OSTEOBLAST; OSTEOPOROSIS; SUPERNATANT; UTERINE CERVIX CARCINOMA;

ADENOCARCINOMA; ALKALINE PHOSPHATASE; ANIMALS; ANTHRAQUINONES; BENZOFURANS; CALCIUM; CELL DIFFERENTIATION; CELL LINE; CELL LINE, TUMOR; CHLORAMPHENICOL O-ACETYLTRANSFERASE; DOSE-RESPONSE RELATIONSHIP, DRUG; ESTRADIOL; ESTROGEN RECEPTOR MODULATORS; ESTROGENS; FEMALE; FURANS; HELA CELLS; HUMANS; INSULIN-LIKE GROWTH FACTOR BINDING PROTEIN 3; MICE; OSTEOBLASTS; PLANTS; PLANTS, MEDICINAL; RECEPTORS, ESTROGEN; TETRAZOLIUM SALTS; THIAZOLES; TIME FACTORS; TRANSFECTION; UTERINE CERVICAL NEOPLASMS;

FELIS CATUS; MINK CELL FOCUS-FORMING VIRUS; ONOBRYCHIS;

EID: 9644273990     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2004.07.005     Document Type: Article

References (30)

1. D.M. Tham, C.D. Gardner, and W.L. Haskell Potential health benefits of dietary phytoestrogens: a review of the clinical, epidemiological and mechanistic evidence J Clin Endocrinol Metab 83 1998 2223 2235
2. A. Brzezinski, and A. Debi Phytoestrogens: the "natural" selective estrogen receptor modulators? Eur J Obstet Gynecol Reprod Biol 85 1999 47 51
3. M.P. Warren, B. Shortle, and J.E. Dominguez Use of alternative therapies in menopause Best Pract Res Clin Obstet Gynaecol 16 2002 411 448
4. M. Halabalaki, N. Aligiannis, Z. Papoutsi, S. Mitakou, P. Moutsatsou, and C.E. Sekeris Three new arylobenzofurans from Onobrychis ebenoides and evaluation of their binding affinity for the estrogen receptor J Nat Prod 63 2000 1672 1674
5. E. Galbiati, P.L. Caruso, G. Amari, E. Armani, S. Ghirardi, and M. Delcanale Effects of 3-phenyl-4-[4-[2(1-piperidinyl)ethoxy]phenyl]methyl-2H-1- benzopyran-7-ol (CHF 4056), a novel nonsteroid estrogen agonist/antagonist, on reproductive and nonreproductive tissue J Pharmacol Exp Ther. 300 2002 802 809
6. E. Von Angerer, C. Biberger, and S. Leichtl Studies on heterocycle-based pure estrogen antagonists Ann NY Acad Sci 761 1995 176 191
7. H. Huynh, X. Yang, and M. Pollak 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 1996 1016 1021
8. Z.C. Dang, R.L. van Bezooijen, M. Karperien, S.E. Papapoulos, and C.W.G.M. Löwik Exposure of KS483 cells to estrogen enhances osteogenesis and inhibits adipogenesis J Bone Miner Res 17 2002 394 405
9. P. Moutsatsou, and C.E. Sekeris Estrogen and progesterone receptors in the endometrium Ann NY Acad Sci 816 1997 99 115
10. V. Zoumpourlis, D.J. Kerr, and D.A. Spandidos Differential interaction of cisplatin with the HIV-1 long terminal repeat in a resistant ovarian carcinoma cell line Anticancer Drugs 4 1993 77 83
11. T. Maeda, A. Matsunuma, T. Kawane, and N. Horiuchi Simvastatin promotes osteoblast differentiation and mineralization in MC3T3-E1 cells Biochem Biophys Res Commun 280 2001 874 877
12. C. Chen, and H. Okayama High-efficiency transformation of mammalian cells by plasmid DNA Mol Cell Biol 7 1987 2745 2752
13. J.C. Reese, and B.S. Katzenellenbogen Examination of the DNA-binding ability of estrogen receptor in whole cells: implications for hormone-independent transactivation and the actions of antiestrogens Mol Cell Biol 12 1992 4535 4538
14. A. Howell, C.K. Osborne, C. Morris, and A.E. Wakeling ICI 182780 (Faslodex): development of a novel,"pure" antiestrogen Cancer 89 4 2000 817 825
15. P. Diel, K. Smolnikar, and H. Michna In vitro test systems for the evaluation of the estrogenic activity of natural products Planta Med 65 1999 197 203
16. J.L. Martin, J.A. Coverley, S.T. Pattison, and R.C. Baxter Insulin-like growth factor-binding protein-3 produciton by MCF-7 breast cancer cells: Stimulation by retinoic acid and cyclic adenosine monophosphate and differential effects of estradiol Endocrinology 136 1995 1219 1226
17. S.E. Pratt, and M.N. Pollak 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 1993 5193 5198
18. R.C. Baxter, and C.L. Martin Radioimmunoassay of growth hormone-dependent insulinlike growth factor binding protein in human plasma J Clin Invest 78 1986 1504 1512
19. G. Fürstenberger, and H.-J. Sonn Insulin-like growth factors and cancer Lancet Oncol 3 2002 298 302
20. K.E. Wangen, A.M. Duncan, B.E. Merz-Demlow, X. Xu, R. Marcus, and W.R. Phipps Effects of soy isoflavones on markers of bone turnover in premenopausal and postmenopausal women J Clin Endocrinol Metab 85 2000 3043 3048
21. B.H. Arjmandi, R.S. Birnbaum, S. Juma, E. Barengolts, and S.C. Kukreja The synthetic phytoestrogen, ipriflavone, and estrogen prevent bone loss by different mechanisms Calcif Tissue Int 66 2000 61 65
22. K. Mizutani, K. Ikeda, Y. Kawai, and Y. Yamori Resveratrol stimulates the proliferation and differentiation of osteoblastic MC3T3-E1 cells Biochem Biophys Res Commun 253 1998 859 863
23. F. Denizof, and R. Lang Rapid colorimetric assay for cell growth and survival: modifications to the tetrozolium dye procedure giving improved sensitivity and reliability J Immunol Methods 89 1986 271 277
24. 3H] luteolin Steroids 66 2001 709 719
25. S. Caltagirone, F.O. Ranelletti, A. Rinelli, N. Maggiano, A. Colasante, and P. Musiani Interaction with type II estrogen binding sites and antiproliferative activity of tamoxifen and quercetin in human non-small-cell lung cancer Am J Respir Cell Mol Biol 17 1997 51 59
26. E. Sivridis, C.H. Buckley, and H. Fox Type I and type II estrogen and progesterone binding sites in endometrial carcinomas: their value in predicting survival Int J Gynecol Cancer 3 1993 80 88
27. W. Washington, L. Hubert, D. Jones, and W.G. Gray Bisphenol a binds to the low-affinity estrogen binding site In Vitro Mol Toxicol 14 2001 43 51
28. A. McDougal, M. Wormke, C. Calvin, and S. Safe Tamoxifen-induced antitumorigenic/antiestrogenic action synergized by a selective aryl hydrocarbon receptor modulator Cancer Res 61 2001 3902 3907
29. N. Durani, R. Jain, A. Saeed, D.K. Dikshit, S. Durani, and R.S. Kapil Structure-activity relationship of antiestrogens: a study using triarylbutenone, benzofuran, and triarylfuran analogues as models for triarylethylenes and triarylpropenones J Med Chem 32 1989 1700 1707
30. T.A. Grese, S. Cho, D.R. Finley, A.G. Godfrey, C.D. Jones, and C.D. Lugar III Structure-activity relationships of selective estrogen receptor modulators: modifications to the 2-arylbenzothiophene core of raloxifene J Med Chem 40 1997 146 167