Evaluation of Estrogenic Potential of Flavonoids Using a Recombinant Yeast Strain and MCF7/BUS Cell Proliferation Assay

PLoS ONE

Volumn 8, Issue 10, 2013, Pages

  Resende, Flávia A ^a   de Oliveira, Ana Paula S ^a   de Camargo, Mariana S ^a   Vilegas, Wagner ^a   Varanda, Eliana A ^a  

^a SÃO PAULO STATE UNIVERSITY UNESP   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

3 HYDROXYFLAVONE; 7 HYDROXYFLAVONE; CHRYSIN; ESTRADIOL; ESTROGEN RECEPTOR; ESTROGEN RECEPTOR ALPHA; FISETIN; FLAVONE; FLAVONOID; GALANGIN; HYDROXYL GROUP; KAEMPFEROL; LUTEOLIN; PHYTOESTROGEN; PRIMULETIN; QUERCETIN;

ANTIESTROGENICITY; ARTICLE; ASSAY; BUS CELL; CELL LINE; CELL PROLIFERATION; CELL PROLIFERATION ASSAY; CELL STRAIN MCF 7; CONTROLLED STUDY; DRUG ACTIVITY; DRUG STRUCTURE; ESTROGEN ACTIVITY; FUNGAL STRAIN; HUMAN; HUMAN CELL; HYDROXYLATION; IN VITRO STUDY; NONHUMAN; RECOMBINANT YEAST ASSAY; TRANSCRIPTION INITIATION; YEAST;

CELL PROLIFERATION; CELL SURVIVAL; DNA, RECOMBINANT; FLAVONOIDS; HUMANS; HYDROXYLATION; MCF-7 CELLS; PHYTOESTROGENS; YEASTS;

EID: 84885068685     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0074881     Document Type: Article

References (31)

1. Brix R, Noguerol TN, Piña B, Balaam J, Nilsen AJ, et al. (2010) Evaluation of the suitability of recombinant yeast-based estrogenicity assays as a pre-screening tool in environmental samples. Environ Int 36: 361-367.
2. Tokarz J, Möller G, Angelis MH, Adamski J (2013) Zebrafish and steroids: what do we know and what do we need to know? J Steroid Biochem Mol Biol doi: 10.1016/j.jsbmb.2013.01.003.
3. Ogawa T, Ohta K, Iijima T, Suzuki T, Ohta S, et al. (2009) Synthesis and biological evaluation of p-carborane bisphenols and their derivatives: structure-activity relationship for estrogenic activity. Bioorg Med Chem 17: 1109-1117.
4. De Naeyer A, Vanden Berghe W, Pocock V, Milligan S, Haegeman G, et al. (2004) Estrogenic and anticarcinogenic properties of kurarinone, a lavandulyl flavanone from the roots of Sophora flavescens. J Nat Prod 67(11): 1829-32.
5. Sharan S, Nikhil K, Roy P, (2013) Effects of low dose treatment of tributyltin on the regulation of estrogen receptor functions in MCF-7 cells. Toxicol Appl Pharmacol. 269(2): 176-186.
6. Garcia-Reyero N, Grau E, Castillo M, López de Alda MJ, Barceló D, et al. (2001) Monitoring of endocrine disruptors in surface waters by the yeast recombinant assay. Environ Toxicol Chem 20: 1152-1158.
7. Céspedes R, Lacorte S, Raldúa D, Ginebreda A, Barceló D, et al, (2005) Distribution of endocrine disruptors in the Llobregat River basin (Catalonia, NE Spain). Chemosphere 61: 1710-1719.
8. Noguerol TN, Boronat S, Jarque S, Barceló D, Piña B, (2006) Detection of hormone receptor ligands in yeast by fluorogenic methods. Talanta 69(2): 351-358.
9. Garcia-Reyero N, Requena V, Petrovic M, Fischer B, Hansen PD, et al. (2004) Estrogenic potential of halogenated derivatives of nonylphenol ethoxylates and carboxylates. Environ Toxicol Chem 23: 705-711.
10. Green S, Chambon P (1991) The oestrogen receptor: from perception to mechanism. In: PARKER, M. G. (Ed.). Nuclear hormone receptors. London: Academic Press, p 15-38.
11. Schneider JC, Guarente L, (1991) Vectors for expression of cloned genes in yeast: Regulation, overproduction, and underproduction. Meth Enzymol 194: 373-388.
12. Villalobos M, Olea N, Brotons JA, Olea-Serrano MF, Ruiz de Almodovar JM, et al. (1995) The E-screen assay: a comparison of different MCF-7 cell stocks. Environ Health Perspect 103: 844-850.
13. Soto AM, Lin TM, Justicia H, Silvia RM, Sonnenschein C (1992) An "in culture" bioassay to assess the estrogenicity of xenobiotics. In: COLBORN T and CLEMENT C. (Eds.) Chemically induced alterations in sexual development: The wildlife/human connection Princeton, NJ: Princeton Scientific Publishing, p.295-309.
14. Tarnow P, Tralau T, Hunecke D, Luch A, (2013) Effects of triclocarban on the transcription of estrogen, androgen and aryl hydrocarbon receptor responsive genes in human breast cancer cells. Toxicol In Vitro 27(5): 1467-1475.
15. Schiliró T, Gorrasi I, Longo A, Coluccia S, Gilli G, (2011) Endocrine disrupting activity in fruits and vegetables evaluated with the E-screen assay in relation to pesticide residues. J Steroid Biochem Mol Biol 127: 139-146.
16. Kuch B, Kern F, Metzger JW, Von der Trenck KT, (2010) Effect-related monitoring: estrogen-like substances in groundwater. Environ Sci Poll Res Int 17: 250-260.
17. Choi SY, Ha TY, Ahn JY, Kim SR, Kang KS, et al. (2008) Estrogenic activities of isoflavones and flavones and their structure-activity relationships. Planta Med 74: 25-32.
18. Zand RS, Jenkins DJ, Diamandis EP, (2000) Steroid hormone activity of flavonoids and related compounds. Breast Cancer Res Treat 62: 35-49.
19. Ferguson LR, (2001) Role of plant polyphenols in genomic stability. Mutat Res 475: 89-111.
20. Kuiper GG, Lemmen JG, Carlsson B, Corton JC, Safe SH, et al. (1998) Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta. Endocrinol 139: 4252-4263.
21. Wanda GJ, Njamen D, Yankep E, Fotsing MT, Fomum ZT, et al. (2006) Estrogenic properties of isoflavones derived from Millettia griffoniana. Phytomed 13: 139-145.
22. Vanparys C, Depiereux S, Nadzialek S, Robbens J, Blust R, et al. (2010) Performance of the flow cytometric E-screen assay in screening estrogenicity of pure compounds and environmental samples. Sci Total Environ 408: 4451-4460.
23. Oh SM, Kim HR, Chung KH, (2009) In vitro estrogenic and antiestrogenic potential of chlorostyrenes. Toxicol In Vitro 23: 1242-1248.
24. Liu S, Han SJ, Smith CL, (2013) Cooperative activation of gene expression by agonists and antagonists mediated by estrogen receptor heteroligand dimer complexes. Mol Pharmacol 85(5): 1066-1077.
25. Fang H, Tong W, Shi LM, Blair R, Perkins R, et al. (2001) Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens. Chem Res Toxicol 14: 280-294.
26. Anstead GM, Carlson KE, Katzenellenbogen JA, (1997) The estradiol pharmacophore: ligand structure-estrogen receptor binding affinity relationships and a model for the receptor binding site. Steroids 62: 268-303.
27. Ward HA, Kuhnle GG, (2010) Phytoestrogen consumption and association with breast, prostate and colorectal cancer in EPIC Norfolk. Arch Biochem Bioph 501: 170-175.
28. Hou DX, Kumamoto T, (2010) Flavonoids as protein kinase inhibitors for cancer chemoprevention: direct binding and molecular modeling. Antiox Redox Signal 13: 691-719.
29. Duarte Silva I, Gaspar J, Gomes da Costa G, Rodrigues AS, Laires A, et al. (2000) Chemical features of flavonols affecting their genotoxicity. Potential implications in their use as therapeutical agents. Chem Biol Interact 124: 29-51.
30. Watanabe C, Egami T, Midorikawa K, Hiraku Y, Oikawa S, et al. (2010) DNA damage and estrogenic activity induced by the environmental pollutant 2-nitrotoluene and its metabolite. Environ Health Prev Med 15: 319-326.
31. De-Eknamkul W, Umehara K, Monthakantirat O, Toth R, Frecer V, et al. (2011) QSAR study of natural estrogen-like isoflavonoids and diphenolics from Thai medicinal plants. J Mol Graph Model 29: 784-794.