6,19-Sulfur-bridged progesterone analogues with antiimmunosuppressive activity
- Autores
- Veleiro, Adriana Silvia; Pecci, Adali; Monteserín, María C.; Baggio, Ricardo Fortunato; Garland, María T.; Lantos, Carlos Pedro; Burton, Gerardo
- Año de publicación
- 2005
- Idioma
- inglés
- Tipo de recurso
- artículo
- Estado
- versión publicada
- Descripción
- Sulfur-bridged pregnanes 6,19-epithioprogesterone, 21-hydroxy-6,19- epithioprogesterone, and the corresponding sulfoxides and sulfones were synthesized and tested as blockers of the immunosuppresive activity of dexamethasone in rat thymocytes. A new one-pot procedure is described for the preparation of 6,19-epithioprogesterone and related compounds by iodocyclization of a 19-sulfanylpregn-5-ene. Antiimmunosuppresive activity was evaluated by the ability of the different steroids to block dexamethasone-mediated apoptosis in thymocytes and dexamethasone-mediated inhibition of the NFκ-B transcription factor activity. DNA fragmentation and annexin V-FITC positive cells were taken as parameters of apoptosis whereas NFκ-B activity was tested by the expression of the reporter vector κB-luciferase by TNF-α in Hela cells. 21-Hydroxy-6,19-epithioprogesterone S,S-dioxide had improved activity in both parameters, while 21-hydroxy-6,19-epithioprogesterone had improved activity only in blocking dexamethasone-induced programmed cell death. © 2005 American Chemical Society.
Fil: Veleiro, Adriana Silvia.
Fil: Pecci, Adali. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Fisiología, Biología Molecular y Neurociencias. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Fisiología, Biología Molecular y Neurociencias; Argentina
Fil: Monteserín, M.C..
Fil: Baggio, Ricardo Fortunato.
Fil: Garland, M.T..
Fil: Lantos, Carlos Pedro. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química Biológica de la Facultad de Ciencias Exactas y Naturales. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química Biológica de la Facultad de Ciencias Exactas y Naturales; Argentina
Fil: Burton, Gerardo. - Materia
- steroid analogs
- Nivel de accesibilidad
- acceso abierto
- Condiciones de uso
- https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
- Repositorio
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/98780
Ver los metadatos del registro completo
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6,19-Sulfur-bridged progesterone analogues with antiimmunosuppressive activityVeleiro, Adriana SilviaPecci, AdaliMonteserín, María C.Baggio, Ricardo FortunatoGarland, María T.Lantos, Carlos PedroBurton, Gerardosteroid analogshttps://purl.org/becyt/ford/3.5https://purl.org/becyt/ford/3Sulfur-bridged pregnanes 6,19-epithioprogesterone, 21-hydroxy-6,19- epithioprogesterone, and the corresponding sulfoxides and sulfones were synthesized and tested as blockers of the immunosuppresive activity of dexamethasone in rat thymocytes. A new one-pot procedure is described for the preparation of 6,19-epithioprogesterone and related compounds by iodocyclization of a 19-sulfanylpregn-5-ene. Antiimmunosuppresive activity was evaluated by the ability of the different steroids to block dexamethasone-mediated apoptosis in thymocytes and dexamethasone-mediated inhibition of the NFκ-B transcription factor activity. DNA fragmentation and annexin V-FITC positive cells were taken as parameters of apoptosis whereas NFκ-B activity was tested by the expression of the reporter vector κB-luciferase by TNF-α in Hela cells. 21-Hydroxy-6,19-epithioprogesterone S,S-dioxide had improved activity in both parameters, while 21-hydroxy-6,19-epithioprogesterone had improved activity only in blocking dexamethasone-induced programmed cell death. © 2005 American Chemical Society.Fil: Veleiro, Adriana Silvia.Fil: Pecci, Adali. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Fisiología, Biología Molecular y Neurociencias. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Fisiología, Biología Molecular y Neurociencias; ArgentinaFil: Monteserín, M.C..Fil: Baggio, Ricardo Fortunato.Fil: Garland, M.T..Fil: Lantos, Carlos Pedro. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química Biológica de la Facultad de Ciencias Exactas y Naturales. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química Biológica de la Facultad de Ciencias Exactas y Naturales; ArgentinaFil: Burton, Gerardo.American Chemical Society2005-09info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/98780Veleiro, Adriana Silvia; Pecci, Adali; Monteserín, María C.; Baggio, Ricardo Fortunato; Garland, María T.; et al.; 6,19-Sulfur-bridged progesterone analogues with antiimmunosuppressive activity; American Chemical Society; Journal of Medicinal Chemistry; 48; 18; 9-2005; 5675-56830022-2623CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1021/jm049266xinfo:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/jm049266xinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T12:07:45Zoai:ri.conicet.gov.ar:11336/98780instacron: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 12:07:45.768CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse |
dc.title.none.fl_str_mv |
6,19-Sulfur-bridged progesterone analogues with antiimmunosuppressive activity |
title |
6,19-Sulfur-bridged progesterone analogues with antiimmunosuppressive activity |
spellingShingle |
6,19-Sulfur-bridged progesterone analogues with antiimmunosuppressive activity Veleiro, Adriana Silvia steroid analogs |
title_short |
6,19-Sulfur-bridged progesterone analogues with antiimmunosuppressive activity |
title_full |
6,19-Sulfur-bridged progesterone analogues with antiimmunosuppressive activity |
title_fullStr |
6,19-Sulfur-bridged progesterone analogues with antiimmunosuppressive activity |
title_full_unstemmed |
6,19-Sulfur-bridged progesterone analogues with antiimmunosuppressive activity |
title_sort |
6,19-Sulfur-bridged progesterone analogues with antiimmunosuppressive activity |
dc.creator.none.fl_str_mv |
Veleiro, Adriana Silvia Pecci, Adali Monteserín, María C. Baggio, Ricardo Fortunato Garland, María T. Lantos, Carlos Pedro Burton, Gerardo |
author |
Veleiro, Adriana Silvia |
author_facet |
Veleiro, Adriana Silvia Pecci, Adali Monteserín, María C. Baggio, Ricardo Fortunato Garland, María T. Lantos, Carlos Pedro Burton, Gerardo |
author_role |
author |
author2 |
Pecci, Adali Monteserín, María C. Baggio, Ricardo Fortunato Garland, María T. Lantos, Carlos Pedro Burton, Gerardo |
author2_role |
author author author author author author |
dc.subject.none.fl_str_mv |
steroid analogs |
topic |
steroid analogs |
purl_subject.fl_str_mv |
https://purl.org/becyt/ford/3.5 https://purl.org/becyt/ford/3 |
dc.description.none.fl_txt_mv |
Sulfur-bridged pregnanes 6,19-epithioprogesterone, 21-hydroxy-6,19- epithioprogesterone, and the corresponding sulfoxides and sulfones were synthesized and tested as blockers of the immunosuppresive activity of dexamethasone in rat thymocytes. A new one-pot procedure is described for the preparation of 6,19-epithioprogesterone and related compounds by iodocyclization of a 19-sulfanylpregn-5-ene. Antiimmunosuppresive activity was evaluated by the ability of the different steroids to block dexamethasone-mediated apoptosis in thymocytes and dexamethasone-mediated inhibition of the NFκ-B transcription factor activity. DNA fragmentation and annexin V-FITC positive cells were taken as parameters of apoptosis whereas NFκ-B activity was tested by the expression of the reporter vector κB-luciferase by TNF-α in Hela cells. 21-Hydroxy-6,19-epithioprogesterone S,S-dioxide had improved activity in both parameters, while 21-hydroxy-6,19-epithioprogesterone had improved activity only in blocking dexamethasone-induced programmed cell death. © 2005 American Chemical Society. Fil: Veleiro, Adriana Silvia. Fil: Pecci, Adali. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Fisiología, Biología Molecular y Neurociencias. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Fisiología, Biología Molecular y Neurociencias; Argentina Fil: Monteserín, M.C.. Fil: Baggio, Ricardo Fortunato. Fil: Garland, M.T.. Fil: Lantos, Carlos Pedro. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química Biológica de la Facultad de Ciencias Exactas y Naturales. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química Biológica de la Facultad de Ciencias Exactas y Naturales; Argentina Fil: Burton, Gerardo. |
description |
Sulfur-bridged pregnanes 6,19-epithioprogesterone, 21-hydroxy-6,19- epithioprogesterone, and the corresponding sulfoxides and sulfones were synthesized and tested as blockers of the immunosuppresive activity of dexamethasone in rat thymocytes. A new one-pot procedure is described for the preparation of 6,19-epithioprogesterone and related compounds by iodocyclization of a 19-sulfanylpregn-5-ene. Antiimmunosuppresive activity was evaluated by the ability of the different steroids to block dexamethasone-mediated apoptosis in thymocytes and dexamethasone-mediated inhibition of the NFκ-B transcription factor activity. DNA fragmentation and annexin V-FITC positive cells were taken as parameters of apoptosis whereas NFκ-B activity was tested by the expression of the reporter vector κB-luciferase by TNF-α in Hela cells. 21-Hydroxy-6,19-epithioprogesterone S,S-dioxide had improved activity in both parameters, while 21-hydroxy-6,19-epithioprogesterone had improved activity only in blocking dexamethasone-induced programmed cell death. © 2005 American Chemical Society. |
publishDate |
2005 |
dc.date.none.fl_str_mv |
2005-09 |
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/11336/98780 Veleiro, Adriana Silvia; Pecci, Adali; Monteserín, María C.; Baggio, Ricardo Fortunato; Garland, María T.; et al.; 6,19-Sulfur-bridged progesterone analogues with antiimmunosuppressive activity; American Chemical Society; Journal of Medicinal Chemistry; 48; 18; 9-2005; 5675-5683 0022-2623 CONICET Digital CONICET |
url |
http://hdl.handle.net/11336/98780 |
identifier_str_mv |
Veleiro, Adriana Silvia; Pecci, Adali; Monteserín, María C.; Baggio, Ricardo Fortunato; Garland, María T.; et al.; 6,19-Sulfur-bridged progesterone analogues with antiimmunosuppressive activity; American Chemical Society; Journal of Medicinal Chemistry; 48; 18; 9-2005; 5675-5683 0022-2623 CONICET Digital CONICET |
dc.language.none.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
info:eu-repo/semantics/altIdentifier/doi/10.1021/jm049266x info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/jm049266x |
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 application/pdf application/pdf application/pdf application/pdf |
dc.publisher.none.fl_str_mv |
American Chemical Society |
publisher.none.fl_str_mv |
American Chemical Society |
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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1846782443950964736 |
score |
12.928904 |