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
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/8276
Ver los metadatos del registro completo
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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 Técnicas2025-09-29T10:41:13Zoai: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:34982025-09-29 10:41:13.598CONICET 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) |
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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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13.070432 |