Glyceollin I enantiomers distinctly regulate ER-mediated gene expression

Autores
Payton Stewart, Florastina; Khupse, Rahul S.; Boue, Stephen M.; Elliot, Steven; Zimmermann, Maria Carla; Skripnikova, Elena V.; Ashe, Hasina; Tilghman, Syreeta L.; Beckman, Barbara S.; Cleveland, Thomas E.; McLachlan, John A.; Bhatnagar, Deepak; Wiese, Thomas E.; Erhardt, Paul; Burow, Matthew E.
Año de publicación
2010
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
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.
Fil: Payton Stewart, Florastina. University of Tulane; Estados Unidos
Fil: Khupse, Rahul S.. University of Toledo Center for Drug Design & Development; Estados Unidos
Fil: Boue, Stephen M.. Southern Regional Research Center; Estados Unidos
Fil: Elliot, Steven. University of Tulane; Estados Unidos
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
Fil: Skripnikova, Elena V.. Xavier University of Louisiana; Estados Unidos
Fil: Ashe, Hasina. Xavier University of Louisiana; Estados Unidos
Fil: Tilghman, Syreeta L.. University of Tulane; Estados Unidos
Fil: Beckman, Barbara S.. University of Tulane; Estados Unidos
Fil: Cleveland, Thomas E.. Southern Regional Research Center; Estados Unidos
Fil: McLachlan, John A.. University of Tulane; Estados Unidos. Xavier University of Louisiana; Estados Unidos
Fil: Bhatnagar, Deepak. Southern Regional Research Center; Estados Unidos
Fil: Wiese, Thomas E.. University of Tulane; Estados Unidos. Xavier University of Louisiana; Estados Unidos
Fil: Erhardt, Paul. University of Toledo. Center for Drug Design & Development; Estados Unidos
Fil: Burow, Matthew E.. University of Tulane; Estados Unidos
Materia
Antiestrogen
Breast Cancer
Enantiomers
Estrogen Receptor
Glyceollin
Pterocarpans
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/58472
Acceder
id CONICETDig_b8445a71375038a5962193982fb5d0ff
oai_identifier_str oai:ri.conicet.gov.ar:11336/58472
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Glyceollin I enantiomers distinctly regulate ER-mediated gene expressionPayton Stewart, FlorastinaKhupse, Rahul S.Boue, Stephen M.Elliot, StevenZimmermann, Maria CarlaSkripnikova, Elena V.Ashe, HasinaTilghman, Syreeta L.Beckman, Barbara S.Cleveland, Thomas E.McLachlan, John A.Bhatnagar, DeepakWiese, Thomas E.Erhardt, PaulBurow, Matthew E.AntiestrogenBreast CancerEnantiomersEstrogen ReceptorGlyceollinPterocarpanshttps://purl.org/becyt/ford/3.1https://purl.org/becyt/ford/3Glyceollins 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.Fil: Payton Stewart, Florastina. University of Tulane; Estados UnidosFil: Khupse, Rahul S.. University of Toledo Center for Drug Design & Development; Estados UnidosFil: Boue, Stephen M.. Southern Regional Research Center; Estados UnidosFil: Elliot, Steven. University of Tulane; Estados UnidosFil: 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; ArgentinaFil: Skripnikova, Elena V.. Xavier University of Louisiana; Estados UnidosFil: Ashe, Hasina. Xavier University of Louisiana; Estados UnidosFil: Tilghman, Syreeta L.. University of Tulane; Estados UnidosFil: Beckman, Barbara S.. University of Tulane; Estados UnidosFil: Cleveland, Thomas E.. Southern Regional Research Center; Estados UnidosFil: McLachlan, John A.. University of Tulane; Estados Unidos. Xavier University of Louisiana; Estados UnidosFil: Bhatnagar, Deepak. Southern Regional Research Center; Estados UnidosFil: Wiese, Thomas E.. University of Tulane; Estados Unidos. Xavier University of Louisiana; Estados UnidosFil: Erhardt, Paul. University of Toledo. Center for Drug Design & Development; Estados UnidosFil: Burow, Matthew E.. University of Tulane; Estados UnidosElsevier Science Inc2010-12info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/58472Payton 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; 870-8780039-128XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0039128X10001236info:eu-repo/semantics/altIdentifier/doi/10.1016/j.steroids.2010.05.007info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T14:36:49Zoai:ri.conicet.gov.ar:11336/58472instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-10-15 14:36:49.696CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Glyceollin I enantiomers distinctly regulate ER-mediated gene expression
title Glyceollin I enantiomers distinctly regulate ER-mediated gene expression
spellingShingle Glyceollin I enantiomers distinctly regulate ER-mediated gene expression
Payton Stewart, Florastina
Antiestrogen
Breast Cancer
Enantiomers
Estrogen Receptor
Glyceollin
Pterocarpans
title_short Glyceollin I enantiomers distinctly regulate ER-mediated gene expression
title_full Glyceollin I enantiomers distinctly regulate ER-mediated gene expression
title_fullStr Glyceollin I enantiomers distinctly regulate ER-mediated gene expression
title_full_unstemmed Glyceollin I enantiomers distinctly regulate ER-mediated gene expression
title_sort Glyceollin I enantiomers distinctly regulate ER-mediated gene expression
dc.creator.none.fl_str_mv Payton Stewart, Florastina
Khupse, Rahul S.
Boue, Stephen M.
Elliot, Steven
Zimmermann, Maria Carla
Skripnikova, Elena V.
Ashe, Hasina
Tilghman, Syreeta L.
Beckman, Barbara S.
Cleveland, Thomas E.
McLachlan, John A.
Bhatnagar, Deepak
Wiese, Thomas E.
Erhardt, Paul
Burow, Matthew E.
author Payton Stewart, Florastina
author_facet Payton Stewart, Florastina
Khupse, Rahul S.
Boue, Stephen M.
Elliot, Steven
Zimmermann, Maria Carla
Skripnikova, Elena V.
Ashe, Hasina
Tilghman, Syreeta L.
Beckman, Barbara S.
Cleveland, Thomas E.
McLachlan, John A.
Bhatnagar, Deepak
Wiese, Thomas E.
Erhardt, Paul
Burow, Matthew E.
author_role author
author2 Khupse, Rahul S.
Boue, Stephen M.
Elliot, Steven
Zimmermann, Maria Carla
Skripnikova, Elena V.
Ashe, Hasina
Tilghman, Syreeta L.
Beckman, Barbara S.
Cleveland, Thomas E.
McLachlan, John A.
Bhatnagar, Deepak
Wiese, Thomas E.
Erhardt, Paul
Burow, Matthew E.
author2_role author
author
author
author
author
author
author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv Antiestrogen
Breast Cancer
Enantiomers
Estrogen Receptor
Glyceollin
Pterocarpans
topic Antiestrogen
Breast Cancer
Enantiomers
Estrogen Receptor
Glyceollin
Pterocarpans
purl_subject.fl_str_mv https://purl.org/becyt/ford/3.1
https://purl.org/becyt/ford/3
dc.description.none.fl_txt_mv 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.
Fil: Payton Stewart, Florastina. University of Tulane; Estados Unidos
Fil: Khupse, Rahul S.. University of Toledo Center for Drug Design & Development; Estados Unidos
Fil: Boue, Stephen M.. Southern Regional Research Center; Estados Unidos
Fil: Elliot, Steven. University of Tulane; Estados Unidos
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
Fil: Skripnikova, Elena V.. Xavier University of Louisiana; Estados Unidos
Fil: Ashe, Hasina. Xavier University of Louisiana; Estados Unidos
Fil: Tilghman, Syreeta L.. University of Tulane; Estados Unidos
Fil: Beckman, Barbara S.. University of Tulane; Estados Unidos
Fil: Cleveland, Thomas E.. Southern Regional Research Center; Estados Unidos
Fil: McLachlan, John A.. University of Tulane; Estados Unidos. Xavier University of Louisiana; Estados Unidos
Fil: Bhatnagar, Deepak. Southern Regional Research Center; Estados Unidos
Fil: Wiese, Thomas E.. University of Tulane; Estados Unidos. Xavier University of Louisiana; Estados Unidos
Fil: Erhardt, Paul. University of Toledo. Center for Drug Design & Development; Estados Unidos
Fil: Burow, Matthew E.. University of Tulane; Estados Unidos
description 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.
publishDate 2010
dc.date.none.fl_str_mv 2010-12
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/58472
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
0039-128X
CONICET Digital
CONICET
url http://hdl.handle.net/11336/58472
identifier_str_mv 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
0039-128X
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0039128X10001236
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.steroids.2010.05.007
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier Science Inc
publisher.none.fl_str_mv Elsevier Science Inc
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.22299

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