A new class of phytoestrogens: Evaluation of the estrogenic activity of deoxybenzoins

Chemistry and Biology

Volumn 11, Issue 3, 2004, Pages 397-406

  Fokialakis, Nikolas ^a   Lambrinidis, George ^a   Mitsiou, Dimitra J ^b   Aligiannis, Nektarios ^a   Mitakou, Sofia ^a   Skaltsounis, Alexios Leandros ^a   Pratsinis, Harris ^c   Mikros, Emmanuel ^a   Alexis, Michael N ^b  

^a UNIVERSITY OF ATHENS   (Greece)

^b INSTITUTE OF BIOLOGY   (Greece)

^c INSTITUTE OF NANOSCIENCE AND NANOTECHNOLOGY   (Greece)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALINE PHOSPHATASE; BENZOIN; DAIDZEIN; DEOXYBENZOIN; DRUG DERIVATIVE; ESTRADIOL; ESTROGEN RECEPTOR; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; ISOFLAVONE DERIVATIVE; PHYTOESTROGEN; PLANT MEDICINAL PRODUCT;

ARTICLE; CELL DIVISION; CELL LINE; CHEMICAL STRUCTURE; CHEMISTRY; CLASSIFICATION; CONFORMATION; DRUG EFFECT; ENZYME ACTIVATION; EVALUATION; GENETIC TRANSCRIPTION; GENETICS; HUMAN; METABOLISM; REPORTER GENE; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ALKALINE PHOSPHATASE; BENZOIN; CELL DIVISION; CELL LINE; ENZYME ACTIVATION; ESTRADIOL; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; GENES, REPORTER; HUMANS; ISOFLAVONES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PHYTOESTROGENS; PLANT PREPARATIONS; RECEPTORS, ESTROGEN; STRUCTURE-ACTIVITY RELATIONSHIP; TRANSCRIPTION, GENETIC;

EID: 6444224110     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chembiol.2004.02.014     Document Type: Article

References (43)

1. Adlercreutz H. Phyto-oestrogens and cancer. Lancet Oncol. 3:2002;364-373.
2. Setchell K.D., Cassidy A. Dietary isoflavones. biological effects and relevance to human health J. Nutr. 129:1999;758S-767S.
3. Moggs J.G., Orphanides G. Estrogen receptors. orchestrators of pleiotropic cellular responses EMBO Rep. 2:2001;775-781.
4. Kuiper G.G.J.M., Carlsson B., Gradien K., Enmark E., Haggblad J., Nilsson S., Gustafsson J.A. Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta. Endocrinology. 138:1997;863-870.
5. An J., Tzagarakis-Foster C., Scharschmidt T.C., Lomri N., Leitman D.C. Estrogen receptor beta-selective transcriptional activity and recruitment of coregulators by phytoestrogens. J. Biol. Chem. 276:2001;17808-17814.
6. Brzozowski A.M., Pike A.C., Dauter Z., Hubbard R.E., Bonn T., Engstrom O., Ohman L., Greene G.L., Gustafsson J.A., Carlquist M. Molecular basis of agonism and antagonism in the oestrogen receptor. Nature. 389:1997;753-758.
7. Shiau A.K., Barstad D., Loria P.M., Cheng L., Kushner P.J., Agard D.A., Greene G.L. The structural basis of estrogen receptor/coactivator recognition and the antagonism of this interaction by tamoxifen. Cell. 95:1998;927-937.
8. Pike A.C.W., Brzozowski A.M., Hubbard R.E., Bonn T., Thorsell A.G., Engstrom O., Ljunggren J., Gustafsson J.E., Carlquist M. Structure of the ligand-binding domain of oestrogen receptor beta in the presence of a partial agonist and a full antagonist. EMBO J. 18:1999;4608-4618.
9. Hermanson O., Glass C.K., Rosenfeld M.G. Nuclear receptor coregulators. multiple modes of modification Trends Endocrinol. Metab. 13:2002;55-60.
10. Sanduja, R., Weinheimer, A.J., and Alam M. (1985). Albizoin: isolation and structure of a Deoxybenzoin from the marine mollusc Nerita albicilla. J. Chem. Res. Synop., 56-57.
11. Wahala K., Hase T.A. Expedient synthesis of polyhydroxyisoflavonoids. J. Chem. Soc. Perkin Trans. 1:1991;3005-3008.
12. Kiuchi F., Chen X., Tsuda Y. Four new phenolic constituents from Licorise (root of Glycyrrhiza sp.). Heterocycles. 31:1990;629-636.
13. Beck A.B., Kowala C., Lamberton J.A. 2,4-Dihydroxy-4'-methoxybenzil, a probable artefact from formononetin in subterranean clover extracts. Aust. J. Chem. 19:1966;1755-1757.
14. Niwa K., Hashimoto M., Morishita S., Yokoyama Y., Mori H., Tamaya T. Preventive effects of Glycyrrhizae radix extract on estrogen-related endometrial carcinogenesis in mice. Jpn. J. Cancer Res. 90:1999;726-732.
15. Stevens M.F.G., Mc Call C.J., Lelieveld P., Alexander P., Richter A., Davies D.E. Structural studies on bioactive compounds.23. Synthesis of polyhydroxylated 2-phenylbenzothiazoles and a comparison of their cytotoxicities and pharmacological properties with genistein and quercetin. J. Med. Chem. 37:1994;1689-1695.
16. Nakanishi S., Myers T.C., Jensen E.V. Acid-catalyzed decomposition of chloro- and fluoroformates. J. Am. Chem. Soc. 77:1955;5033-5034.
17. Bolger R., Wiese T.E., Ervin K., Nestich S., Checovich W. Rapid screening of environmental chemicals for estrogen receptor binding capacity. Environ. Health Perspect. 106:1998;551-557.
18. Maggiolini M., Bonofiglio D., Marsico S., Panno M.L., Cenni B., Picard D., Ando S. Estrogen receptor alpha mediates the proliferative but not the cytotoxic dose-dependent effects of two major phytoestrogens on human breast cancer cells. Mol. Pharmacol. 60:2001;595-602.
19. Vladusic E.A., Hornby A.E., Guerra-Vladusic F.K., Lakins J., Lupu R. Expression and regulation of estrogen receptor beta in human breast tumors and cell lines. Oncol. Rep. 7:2000;157-167.
20. Monje P., Boland R. Expression and cellular localization of naturally occurring beta estrogen receptors in uterine and mammary cell lines. J. Cell. Biochem. 86:2002;136-144.
21. Lascombe I., Beffa D., Ruegg U., Tarradellas J., Wahli W. Estrogenic activity assessment of environmental chemicals using in vitro assays. identification of two new estrogenic compounds Environ. Health Perspect. 108:2000;621-629.
22. Peterson G., Barnes S. Genistein inhibits both estrogen and growth factor-stimulated proliferation of human breast cancer cells. Cell Growth Differ. 7:1996;1345-1351.
23. Razandi M., Pedram A., Park S.T., Levin E.R. Proximal events in signaling by plasma membrane estrogen receptors. J. Biol. Chem. 278:2003;2701-2712.
24. Razandi M., Pedram A., Greene G.L., Levin E.R. Cell membrane and nuclear estrogen receptors (ERs) originate from a single transcript. studies of ERalpha and ERbeta expressed in Chinese hamster ovary cells Mol. Endocrinol. 13:1999;307-319.
25. Migliaccio A., Castoria G., Di Domenico M., de Falco A., Bilancio A., Lombardi M., Bottero D., Varricchio L., Nanayakkara M., Rotondi A.et al. Sex steroid hormones act as growth factors. J. Steroid Biochem. Mol. Biol. 83:2003;31-35.
26. Cowley S.M., Parker M.G. A comparison of transcriptional activation by ER alpha and ER beta. J. Steroid Biochem. Mol. Biol. 69:1999;165-175.
27. Metzger D., Berry M., Ali S., Chambon P. Effect of antagonists on DNA binding properties of the human estrogen receptor in vitro and in vivo. Mol. Endocrinol. 9:1995;579-591.
28. Pettersson K., Delaunay F., Gustafsson J.A. Estrogen receptor beta acts as a dominant regulator of estrogen signaling. Oncogene. 19:2000;4970-4978.
29. Matsuda K., Ochiai I., Nishi M., Kawata M. Colocalization and ligand-dependent discrete distribution of the estrogen receptor (ER)alpha and (ER)beta. Mol. Endocrinol. 16:2002;2215-2230.
30. Littlefield B.A., Gurpide E., Markiewicz L., McKinley B., 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. 127:1990;2757-2762.
31. Markiewicz L., Garey J., Adlercreutz H., Gurpide E. In vitro bioassays of non-steroidal phytoestrogens. J. Steroid Biochem. Mol. Biol. 45:1993;399-405.
32. Mohamadi F., Richards N.G.J., Guida W.C., Liskamp R., Caufield C., Chang G., Hendrickson T., Still W.C. Macromodel. an integrated software system for modeling organic and bioorganic molecules using molecular mechanics J. Comput. Chem. 11:1990;440-467.
33. Blaney J., Weiner P.K., Dearing A., Kolmman P.A., Jorgensen E.C., Oatley S.J., Burridge J.M., Blake J.F. Molecular mechanics simulation of protein-ligand interactions. binding of thyroid hormone analogues to prealbumin J. Am. Chem. Soc. 104:1982;6424-6434.
34. Gangloff M., Ruff M., Eiler S., Duclaud S., Wurtz J.M., Moras D. Crystal structure of a mutant hERalpha ligand-binding domain reveals key structural features for the mechanism of partial agonism. J. Biol. Chem. 276:2001;15059-15065.
35. Gao H., Katzenellenbogen J.A., Garg R., Hansch C. Comparative QSAR analysis of estrogen receptor ligands. Chem. Rev. 99:1999;723-744.
36. Manolagas S.C., Kousteni S. Perspective. nonreproductive sites of action of reproductive hormones Endocrinology. 142:2001;2200-2204.
37. Shoker B.S., Shoker B.S., Jarvis C., Clarke R.B., Anderson E., Hewlett J., Davies M.P., Sibson D.R., Sloane J.P. Estrogen receptor-positive proliferating cells in the normal and precancerousbreast. Am. J. Pathol. 155:1999;1811-1815.
38. Roger P., Sahla M.E., Makela S., Gustafsson J.A., Baldet P., Rochefort H. Decreased expression of estrogen receptor beta protein in proliferative preinvasive mammary tumors. Cancer Res. 61:2001;2537-2541.
39. Balasubramanian S., Nair M.G. An efficient "one pot" synthesis of isoflavones. Synthetic Communications. 30:2000;469-484.
40. Denizot F., Lang R. Rapid colorimetric assay for cell growth and survival. Modifications to the tetrazolium dye procedure giving improved sensitivity and reliability. J. Immunol. Methods. 89:1986;271-277.
41. Berthois Y., Katzenellenbogen J.A., Katzenellenbogen B.S. Phenol red in tissue culture media is a weak estrogen. implications concerning the study of estrogen-responsive cells in culture Proc. Natl. Acad. Sci. USA. 83:1986;2496-2500.
42. Stewart J.J.P. A semiempirical molecular orbital program. J. Comput. Aided Mol. Des. 4:1990;1-105.
43. Vedani A., Hutha D.W. A new force field for modelling metalloproteins. J. Am. Chem. Soc. 112:1990;4759-4767.