Identification and characterization of a novel estrogenic ligand actinopolymorphol A

Biochemical Pharmacology

Volumn 80, Issue 8, 2010, Pages 1221-1229

  Powell, Emily ^a   Huang, Sheng Xiong ^b   Xu, Yong ^d   Rajski, Scott R ^b   Wang, Yidan ^a   Peters, Noel ^c   Guo, Song ^c   Eric Xu, H ^d   Hoffmann, F Michael ^a,c   Shen, Ben ^b   Xu, Wei ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

^b UNIVERSITY OF WISCONSIN MADISON   (United States)

^c UNIVERSITY OF WISCONSIN   (United States)

^d VAN ANDEL RESEARCH INSTITUTE   (United States)

Author keywords

BRET; Estrogen receptor ; Estrogen receptor ; Soil bacteria; Xenoestrogens

Indexed keywords

ACTINOPOLYMORPHOL A; ESTROGEN; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; HETERODIMER; HOMODIMER; UNCLASSIFIED DRUG; ACETIC ACID DERIVATIVE; ESTROGEN RECEPTOR; PHENOL DERIVATIVE; PROTEIN BINDING;

ARTICLE; BIOLUMINESCENCE RESONANCE ENERGY TRANSFER; CELL COUNT; CELL PROLIFERATION; CELL VIABILITY; CONTROLLED STUDY; DIMERIZATION; HIGH THROUGHPUT SCREENING; HORMONE RECEPTOR INTERACTION; HUMAN; HUMAN CELL; PRIORITY JOURNAL; PROTEIN CONFORMATION; REVERSE TRANSCRIPTION POLYMERASE CHAIN REACTION; SOIL MICROFLORA; WESTERN BLOTTING; AGONISTS; ANIMAL; BACTERIA; BIOASSAY; BREAST TUMOR; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; FEMALE; METABOLISM; MICROBIOLOGY; RAT; TUMOR CELL LINE;

ACETATES; ANIMALS; BACTERIA; BIOLOGICAL ASSAY; BREAST NEOPLASMS; CELL LINE, TUMOR; DOSE-RESPONSE RELATIONSHIP, DRUG; ESTROGENS; FEMALE; HUMANS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PHENOLS; PROTEIN BINDING; PROTEIN CONFORMATION; RATS; RECEPTORS, ESTROGEN; SOIL MICROBIOLOGY;

EID: 77956229208     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bcp.2010.06.030     Document Type: Article

References (41)

1. Chang E.C., Frasor J., Komm B., Katzenellenbogen B.S. Impact of estrogen receptor beta on gene networks regulated by estrogen receptor alpha in breast cancer cells. Endocrinology 2006, 147:4831-4842.
2. Helguero L.A., Faulds M.H., Gustafsson J.A., Haldosen L.A. Estrogen receptors alfa (ERalpha) and beta (ERbeta) differentially regulate proliferation and apoptosis of the normal murine mammary epithelial cell line HC11. Oncogene 2005, 24:6605-6616.
3. Liu M.M., Albanese C., Anderson C.M., Hilty K., Webb P., Uht R.M., et al. Opposing action of estrogen receptors alpha and beta on cyclin D1 gene expression. J Biol Chem 2002, 277:24353-24360.
4. Pettersson K., Delaunay F., Gustafsson J.A. Estrogen receptor beta acts as a dominant regulator of estrogen signaling. Oncogene 2000, 19:4970-4978.
5. Shoker B.S., Jarvis C., Sibson D.R., Walker C., Sloane J.P. Oestrogen receptor expression in the normal and pre-cancerous breast. J Pathol 1999, 188:237-244.
6. Tilli M.T., Frech M.S., Steed M.E., Hruska K.S., Johnson M.D., Flaws J.A., et al. Introduction of estrogen receptor-alpha into the tTA/TAg conditional mouse model precipitates the development of estrogen-responsive mammary adenocarcinoma. Am J Pathol 2003, 163:1713-1719.
7. Kato S., Endoh H., Masuhiro Y., Kitamoto T., Uchiyama S., Sasaki H., et al. Activation of the estrogen receptor through phosphorylation by mitogen-activated protein kinase. Science 1995, 270:1491-1494.
8. Aronica S.M., Katzenellenbogen B.S. Stimulation of estrogen receptor-mediated transcription and alteration in the phosphorylation state of the rat uterine estrogen receptor by estrogen, cyclic adenosine monophosphate, and insulin-like growth factor-I. Mol Endocrinol 1993, 7:743-752.
9. Ignar-Trowbridge D.M., Nelson K.G., Bidwell M.C., Curtis S.W., Washburn T.F., McLachlan J.A., et al. Coupling of dual signaling pathways: epidermal growth factor action involves the estrogen receptor. Proc Natl Acad Sci USA 1992, 89:4658-4662.
10. Bunone G., Briand P.A., Miksicek R.J., Picard D. Activation of the unliganded estrogen receptor by EGF involves the MAP kinase pathway and direct phosphorylation. EMBO J 1996, 15:2174-2183.
11. Filardo E.J., Quinn J.A., Bland K.I., Frackelton A.R. Estrogen-induced activation of Erk-1 and Erk-2 requires the G protein-coupled receptor homolog, GPR30, and occurs via trans-activation of the epidermal growth factor receptor through release of HB-EGF. Mol Endocrinol 2000, 14:1649-1660.
12. Monroe D.G., Secreto F.J., Subramaniam M., Getz B.J., Khosla S., Spelsberg T.C. Estrogen receptor alpha and beta heterodimers exert unique effects on estrogen- and tamoxifen-dependent gene expression in human U2OS osteosarcoma cells. Mol Endocrinol 2005, 19:1555-1568.
13. Stossi F., Barnett D.H., Frasor J., Komm B., Lyttle C.R., Katzenellenbogen B.S. Transcriptional profiling of estrogen-regulated gene expression via estrogen receptor (ER) alpha or ERbeta in human osteosarcoma cells: distinct and common target genes for these receptors. Endocrinology 2004, 145:3473-3486.
14. Powell E., Xu W. Intermolecular interactions identify ligand-selective activity of estrogen receptor alpha/beta dimers. Proc Natl Acad Sci USA 2008, 105:19012-19017.
15. Liu X., Tani A., Kimbara K., Kawai F. Metabolic pathway of xenoestrogenic short ethoxy chain-nonylphenol to nonylphenol by aerobic bacteria, Ensifer sp. strain AS08 and Pseudomonas sp. strain AS90. Appl Microbiol Biotechnol 2006, 72:552-559.
16. Gorbach S.L. Estrogens, breast cancer, and intestinal flora. Rev Infect Dis 1984, 6(Suppl. 1):S85-S90.
17. Xie L.H., Ahn E.M., Akao T., Abdel-Hafez A.A., Nakamura N., Hattori M. Transformation of arctiin to estrogenic and antiestrogenic substances by human intestinal bacteria. Chem Pharm Bull (Tokyo) 2003, 51:378-384.
18. Hori Y., Abe Y., Ezaki M., Goto T., Okuhara M., Kohsaka M. R1128 substances, novel non-steroidal estrogen-receptor antagonists produced by a Streptomyces. I. Taxonomy, fermentation, isolation and biological properties. J Antibiot (Tokyo) 1993, 46:1055-1062.
19. Hori Y., Abe Y., Nishimura M., Goto T., Okuhara M., Kohsaka M. R1128 substances, novel non-steroidal estrogen-receptor antagonists produced by a Streptomyces. III. Pharmacological properties and antitumor activities. J Antibiot (Tokyo) 1993, 46:1069-1075.
20. Hori Y., Takase S., Shigematsu N., Goto T., Okuhara M., Kohsaka M. R1128 substances, novel non-steroidal estrogen-receptor antagonists produced by a Streptomyces. II. Physico-chemical properties and structure determination. J Antibiot (Tokyo) 1993, 46:1063-1068.
21. Kondo H., Nakajima S., Yamamoto N., Okura A., Satoh F., Suda H., et al. BE-14348 substances, new specific estrogen-receptor binding inhibitors. Production, isolation, structure determination and biological properties. J Antibiot (Tokyo) 1990, 43:1533-1542.
22. Matseliukh B.P., Polishchuk L.V., Lutchenko V.V., Bambura O.I., Kopiyko O.P. Synthesis of daidzein and genistein by streptomycetes and their effect on production of antibiotics. Mikrobiol Z 2005, 67:12-21.
23. Kang J.H., Katayama Y., Kondo F. Biodegradation or metabolism of bisphenol A: from microorganisms to mammals. Toxicology 2006, 217:81-90.
24. John D.M., White G.F. Mechanism for biotransformation of nonylphenol polyethoxylates to xenoestrogens in Pseudomonas putida. J Bacteriol 1998, 180:4332-4338.
25. Clavel T., Henderson G., Alpert C.A., Philippe C., Rigottier-Gois L., Dore J., et al. Intestinal bacterial communities that produce active estrogen-like compounds enterodiol and enterolactone in humans. Appl Environ Microbiol 2005, 71:6077-6085.
26. Newman D.J., Cragg G.M., Snader K.M. Natural products as sources of new drugs over the period 1981-2002. J Nat Prod 2003, 66:1022-1037.
27. Powell E., Wang Y., Shapiro D.J., Xu W. Differential requirements of Hsp90 and DNA for the formation of estrogen receptor homodimers and heterodimers. J Biol Chem 2010, 285:16125-16134.
28. Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 1983, 65:55-63.
29. Pfleger K.D., Eidne K.A. Illuminating insights into protein-protein interactions using bioluminescence resonance energy transfer (BRET). Nat Methods 2006, 3:165-174.
30. Wang C.L., Takenaka S., Murakami S., Aoki K. Isolation of a benzoate-utilizing Pseudomonas strain from soil and production of catechol from benzoate by transpositional mutants. Microbiol Res 2001, 156:151-158.
31. Tsai S.C., Tsai L.D., Li Y.K. An isolated Candida albicans TL3 capable of degrading phenol at large concentration. Biosci Biotechnol Biochem 2005, 69:2358-2367.
32. Sweetman A.J., Valle M.D., Prevedouros K., Jones K.C. The role of soil organic carbon in the global cycling of persistent organic pollutants (POPs): interpreting and modelling field data. Chemosphere 2005, 60:959-972.
33. Du Y., Zhou M., Lei L. Role of the intermediates in the degradation of phenolic compounds by Fenton-like process. J Hazard Mater 2006, 136:859-865.
34. Tremblay A., Tremblay G.B., Labrie F., Giguere V. Ligand-independent recruitment of SRC-1 to estrogen receptor beta through phosphorylation of activation function AF-1. Mol Cell 1999, 3:513-519.
35. Maruyama S., Fujimoto N., Asano K., Ito A., Usui T. Expression of estrogen receptor alpha and beta mRNAs in prostate cancers treated with leuprorelin acetate. Eur Urol 2000, 38:635-639.
36. Bolger R., Wiese T.E., Ervin K., Nestich S., Checovich W. Rapid screening of environmental chemicals for estrogen receptor binding capacity. Environ Health Perspect 1998, 106:551-557.
37. Parker G.J., Law T.L., Lenoch F.J., Bolger R.E. Development of high throughput screening assays using fluorescence polarization: nuclear receptor-ligand-binding and kinase/phosphatase assays. J Biomol Screen 2000, 5:77-88.
38. 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 1998, 139:4252-4263.
39. Baker M.E. Flavonoids as hormones. A perspective from an analysis of molecular fossils. Adv Exp Med Biol 1998, 439:249-267.
40. Peters N.K., Frost J.W., Long S.R. A plant flavone, luteolin, induces expression of Rhizobium meliloti nodulation genes. Science 1986, 233:977-980.
41. Huang S.-X., Powell E., Rajski S., Zhao L.-Z., Jiang C.-L., Duan Y., et al. Discovery and total synthesis of a new estrogen receptor heterodimerizing actinopolymorphol A from Actinopolymorpha rutilus. Organic Letters 2010, in press.