Synthesis and biological evaluation of salpichrolide analogues as antiestrogenic agents

Autores
Sonego, Juan Manuel; Rivero, Ezequiel Mariano; Gargiulo, Lucía; Luthy, Isabel Alicia; Alvarez, Lautaro Damian; Veleiro, Adriana Silvia; Burton, Gerardo
Año de publicación
2014
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The antiestrogenic activity of three natural salpichrolides A, G and B (1, 3 and 4) and of five synthetic analogs containing an aromatic D ring and a simplified side chain (5–9), was evaluated on MCF-7 cells. The 2,3-ene-1-keto steroids 8 and 9 were obtained from 3β-acetoxy-17(13→18)-abeo-5αH-pregna-13,15,17-trien-20-one, the key step for these syntheses being a Wharton carbonyl rearrangement of a 1,2-epoxy-3-keto steroid to the allylic alcohol using hydrazine hydrate. The antiestrogenic activity was evaluated by performing dose–response experiments in ER(+) MCF-7 breast cancer cells. Dose-dependent proliferation was quantified via [3H]-thymidine incorporation after 3 days treatment. Salpichrolides A, G and B and analogs 5, 8 and 9 were active as antiestrogens with compound 9 being the most active of the synthetic analogs. Compounds 5 and 9 were also evaluated against the ER(−) cell line MDA-MB-231 and shown to be inactive.
Fil: Sonego, Juan Manuel. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos Aplicados a la Química Orgánica (i); Argentina
Fil: Rivero, Ezequiel Mariano. Fundacion de Instituto de Biologia y Medicina Experimental; Argentina
Fil: Gargiulo, Lucía. Fundacion de Instituto de Biologia y Medicina Experimental; Argentina
Fil: Luthy, Isabel Alicia. Fundacion de Instituto de Biologia y Medicina Experimental; Argentina
Fil: Alvarez, Lautaro Damian. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos Aplicados a la Química Orgánica (i); Argentina
Fil: Veleiro, Adriana Silvia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos Aplicados a la Química Orgánica (i); Argentina
Fil: Burton, Gerardo. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos Aplicados a la Química Orgánica (i); Argentina
Materia
Antiestrogenic Activity
Salpichrolides
Withanolides
Antiproliferative Activity
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/8276
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/8276
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis and biological evaluation of salpichrolide analogues as antiestrogenic agentsSonego, Juan ManuelRivero, Ezequiel MarianoGargiulo, LucíaLuthy, Isabel AliciaAlvarez, Lautaro DamianVeleiro, Adriana SilviaBurton, GerardoAntiestrogenic ActivitySalpichrolidesWithanolidesAntiproliferative Activityhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The antiestrogenic activity of three natural salpichrolides A, G and B (1, 3 and 4) and of five synthetic analogs containing an aromatic D ring and a simplified side chain (5–9), was evaluated on MCF-7 cells. The 2,3-ene-1-keto steroids 8 and 9 were obtained from 3β-acetoxy-17(13→18)-abeo-5αH-pregna-13,15,17-trien-20-one, the key step for these syntheses being a Wharton carbonyl rearrangement of a 1,2-epoxy-3-keto steroid to the allylic alcohol using hydrazine hydrate. The antiestrogenic activity was evaluated by performing dose–response experiments in ER(+) MCF-7 breast cancer cells. Dose-dependent proliferation was quantified via [3H]-thymidine incorporation after 3 days treatment. Salpichrolides A, G and B and analogs 5, 8 and 9 were active as antiestrogens with compound 9 being the most active of the synthetic analogs. Compounds 5 and 9 were also evaluated against the ER(−) cell line MDA-MB-231 and shown to be inactive.Fil: Sonego, Juan Manuel. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos Aplicados a la Química Orgánica (i); ArgentinaFil: Rivero, Ezequiel Mariano. Fundacion de Instituto de Biologia y Medicina Experimental; ArgentinaFil: Gargiulo, Lucía. Fundacion de Instituto de Biologia y Medicina Experimental; ArgentinaFil: Luthy, Isabel Alicia. Fundacion de Instituto de Biologia y Medicina Experimental; ArgentinaFil: Alvarez, Lautaro Damian. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos Aplicados a la Química Orgánica (i); ArgentinaFil: Veleiro, Adriana Silvia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos Aplicados a la Química Orgánica (i); ArgentinaFil: Burton, Gerardo. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos Aplicados a la Química Orgánica (i); ArgentinaElsevier Masson2014-05info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/8276Sonego, Juan Manuel; Rivero, Ezequiel Mariano; Gargiulo, Lucía; Luthy, Isabel Alicia; Alvarez, Lautaro Damian; et al.; Synthesis and biological evaluation of salpichrolide analogues as antiestrogenic agents; Elsevier Masson; European Journal Of Medical Chemistry; 82; 5-2014; 233-2410223-5234enginfo:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0223523414004991info:eu-repo/semantics/altIdentifier/doi/10.1016/j.ejmech.2014.05.067info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T12:13:46Zoai:ri.conicet.gov.ar:11336/8276instacron: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:34982025-10-22 12:13:46.296CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis and biological evaluation of salpichrolide analogues as antiestrogenic agents
title Synthesis and biological evaluation of salpichrolide analogues as antiestrogenic agents
spellingShingle Synthesis and biological evaluation of salpichrolide analogues as antiestrogenic agents
Sonego, Juan Manuel
Antiestrogenic Activity
Salpichrolides
Withanolides
Antiproliferative Activity
title_short Synthesis and biological evaluation of salpichrolide analogues as antiestrogenic agents
title_full Synthesis and biological evaluation of salpichrolide analogues as antiestrogenic agents
title_fullStr Synthesis and biological evaluation of salpichrolide analogues as antiestrogenic agents
title_full_unstemmed Synthesis and biological evaluation of salpichrolide analogues as antiestrogenic agents
title_sort Synthesis and biological evaluation of salpichrolide analogues as antiestrogenic agents
dc.creator.none.fl_str_mv Sonego, Juan Manuel
Rivero, Ezequiel Mariano
Gargiulo, Lucía
Luthy, Isabel Alicia
Alvarez, Lautaro Damian
Veleiro, Adriana Silvia
Burton, Gerardo
author Sonego, Juan Manuel
author_facet Sonego, Juan Manuel
Rivero, Ezequiel Mariano
Gargiulo, Lucía
Luthy, Isabel Alicia
Alvarez, Lautaro Damian
Veleiro, Adriana Silvia
Burton, Gerardo
author_role author
author2 Rivero, Ezequiel Mariano
Gargiulo, Lucía
Luthy, Isabel Alicia
Alvarez, Lautaro Damian
Veleiro, Adriana Silvia
Burton, Gerardo
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv Antiestrogenic Activity
Salpichrolides
Withanolides
Antiproliferative Activity
topic Antiestrogenic Activity
Salpichrolides
Withanolides
Antiproliferative Activity
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The antiestrogenic activity of three natural salpichrolides A, G and B (1, 3 and 4) and of five synthetic analogs containing an aromatic D ring and a simplified side chain (5–9), was evaluated on MCF-7 cells. The 2,3-ene-1-keto steroids 8 and 9 were obtained from 3β-acetoxy-17(13→18)-abeo-5αH-pregna-13,15,17-trien-20-one, the key step for these syntheses being a Wharton carbonyl rearrangement of a 1,2-epoxy-3-keto steroid to the allylic alcohol using hydrazine hydrate. The antiestrogenic activity was evaluated by performing dose–response experiments in ER(+) MCF-7 breast cancer cells. Dose-dependent proliferation was quantified via [3H]-thymidine incorporation after 3 days treatment. Salpichrolides A, G and B and analogs 5, 8 and 9 were active as antiestrogens with compound 9 being the most active of the synthetic analogs. Compounds 5 and 9 were also evaluated against the ER(−) cell line MDA-MB-231 and shown to be inactive.
Fil: Sonego, Juan Manuel. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos Aplicados a la Química Orgánica (i); Argentina
Fil: Rivero, Ezequiel Mariano. Fundacion de Instituto de Biologia y Medicina Experimental; Argentina
Fil: Gargiulo, Lucía. Fundacion de Instituto de Biologia y Medicina Experimental; Argentina
Fil: Luthy, Isabel Alicia. Fundacion de Instituto de Biologia y Medicina Experimental; Argentina
Fil: Alvarez, Lautaro Damian. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos Aplicados a la Química Orgánica (i); Argentina
Fil: Veleiro, Adriana Silvia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos Aplicados a la Química Orgánica (i); Argentina
Fil: Burton, Gerardo. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos Aplicados a la Química Orgánica (i); Argentina
description The antiestrogenic activity of three natural salpichrolides A, G and B (1, 3 and 4) and of five synthetic analogs containing an aromatic D ring and a simplified side chain (5–9), was evaluated on MCF-7 cells. The 2,3-ene-1-keto steroids 8 and 9 were obtained from 3β-acetoxy-17(13→18)-abeo-5αH-pregna-13,15,17-trien-20-one, the key step for these syntheses being a Wharton carbonyl rearrangement of a 1,2-epoxy-3-keto steroid to the allylic alcohol using hydrazine hydrate. The antiestrogenic activity was evaluated by performing dose–response experiments in ER(+) MCF-7 breast cancer cells. Dose-dependent proliferation was quantified via [3H]-thymidine incorporation after 3 days treatment. Salpichrolides A, G and B and analogs 5, 8 and 9 were active as antiestrogens with compound 9 being the most active of the synthetic analogs. Compounds 5 and 9 were also evaluated against the ER(−) cell line MDA-MB-231 and shown to be inactive.
publishDate 2014
dc.date.none.fl_str_mv 2014-05
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/11336/8276
Sonego, Juan Manuel; Rivero, Ezequiel Mariano; Gargiulo, Lucía; Luthy, Isabel Alicia; Alvarez, Lautaro Damian; et al.; Synthesis and biological evaluation of salpichrolide analogues as antiestrogenic agents; Elsevier Masson; European Journal Of Medical Chemistry; 82; 5-2014; 233-241
0223-5234
url http://hdl.handle.net/11336/8276
identifier_str_mv Sonego, Juan Manuel; Rivero, Ezequiel Mariano; Gargiulo, Lucía; Luthy, Isabel Alicia; Alvarez, Lautaro Damian; et al.; Synthesis and biological evaluation of salpichrolide analogues as antiestrogenic agents; Elsevier Masson; European Journal Of Medical Chemistry; 82; 5-2014; 233-241
0223-5234
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/S0223523414004991
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.ejmech.2014.05.067
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
application/pdf
application/pdf
application/pdf
application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier Masson
publisher.none.fl_str_mv Elsevier Masson
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 12.982451

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