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dc.contributor.author
Payton Stewart, Florastina
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Khupse, Rahul S.
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Boue, Stephen M.
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Elliot, Steven
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Zimmermann, Maria Carla
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Skripnikova, Elena V.
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Ashe, Hasina
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Tilghman, Syreeta L.
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Beckman, Barbara S.
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Cleveland, Thomas E.
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McLachlan, John A.
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Bhatnagar, Deepak
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Wiese, Thomas E.
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Erhardt, Paul
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Burow, Matthew E.
dc.date.available
2018-09-05T20:39:20Z
dc.date.issued
2010-12
dc.identifier.citation
Payton Stewart, Florastina; Khupse, Rahul S.; Boue, Stephen M.; Elliot, Steven; Zimmermann, Maria Carla; et al.; Glyceollin I enantiomers distinctly regulate ER-mediated gene expression; Elsevier Science Inc; Steroids; 75; 12; 12-2010; 870-878
dc.identifier.issn
0039-128X
dc.identifier.uri
http://hdl.handle.net/11336/58472
dc.description.abstract
Glyceollins are pterocarpan phytoalexins elicited in high concentrations when soybeans are stressed. We have previously reported that the three glyceollin isomers (GLY I-III) exhibit antiestrogenic properties, which may have significant biological effects upon human exposure. Of the three isomers, we have recently shown that glyceollin I is the most potent antiestrogen. Natural (-)-glyceollin I recently was synthesized along with its racemate and unnatural (+) enantiomer. In this study, we compared the glyceollin I enantiomers' ER binding affinity, ability to inhibit estrogen responsive element transcriptional (ERE) activity and endogenous gene expression in MCF-7 cells. The results demonstrated similar binding affinities for both ERα and ERβ. Reporter gene assays in MCF-7 cells revealed that while (+)-glyceollin I slightly stimulated ERE transcriptional activity, (-)-glyceollin I decreased activity induced by estrogen. Co-transfection reporter assays performed in HEK 293 cells demonstrated that (+)-glyceollin I increased ERE transcriptional activity of ERα and ERβ with and without estrogen with no antiestrogenic activity observed. Conversely, (-)-glyceollin I decreased the activity of both ER subtypes stimulated by estradiol demonstrating potent antiestrogenic properties. Additionally, each Gly I enantiomer induced unique gene expression profiles in a PCR array panel of genes commonly altered in breast cancer.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
Elsevier Science Inc
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dc.rights
info:eu-repo/semantics/openAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject
Antiestrogen
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Breast Cancer
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Enantiomers
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Estrogen Receptor
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Glyceollin
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Pterocarpans
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Inmunología
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Medicina Básica
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CIENCIAS MÉDICAS Y DE LA SALUD
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dc.title
Glyceollin I enantiomers distinctly regulate ER-mediated gene expression
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
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info:eu-repo/semantics/publishedVersion
dc.date.updated
2018-08-17T19:00:33Z
dc.journal.volume
75
dc.journal.number
12
dc.journal.pagination
870-878
dc.journal.pais
Países Bajos
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dc.journal.ciudad
Amsterdam
dc.description.fil
Fil: Payton Stewart, Florastina. University of Tulane; Estados Unidos
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Fil: Khupse, Rahul S.. University of Toledo Center for Drug Design & Development; Estados Unidos
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Fil: Boue, Stephen M.. Southern Regional Research Center; Estados Unidos
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Fil: Elliot, Steven. University of Tulane; Estados Unidos
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Fil: Zimmermann, Maria Carla. University of Tulane; Estados Unidos. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Nordeste; Argentina. Universidad Nacional del Nordeste. Facultad de Medicina; Argentina
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Fil: Skripnikova, Elena V.. Xavier University of Louisiana; Estados Unidos
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Fil: Ashe, Hasina. Xavier University of Louisiana; Estados Unidos
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Fil: Tilghman, Syreeta L.. University of Tulane; Estados Unidos
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Fil: Beckman, Barbara S.. University of Tulane; Estados Unidos
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Fil: Cleveland, Thomas E.. Southern Regional Research Center; Estados Unidos
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Fil: McLachlan, John A.. University of Tulane; Estados Unidos. Xavier University of Louisiana; Estados Unidos
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Fil: Bhatnagar, Deepak. Southern Regional Research Center; Estados Unidos
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Fil: Wiese, Thomas E.. University of Tulane; Estados Unidos. Xavier University of Louisiana; Estados Unidos
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Fil: Erhardt, Paul. University of Toledo. Center for Drug Design & Development; Estados Unidos
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Fil: Burow, Matthew E.. University of Tulane; Estados Unidos
dc.journal.title
Steroids
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dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0039128X10001236
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info:eu-repo/semantics/altIdentifier/doi/https://doi.org/10.1016/j.steroids.2010.05.007
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