6,19-Sulfur-bridged progesterone analogues with antiimmunosuppressive activity

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...

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Autores: Veleiro, Adriana Silvia, Pecci, Adali, Monteserín, María C., Baggio, Ricardo Fortunato, Garland, María T., Lantos, Carlos Pedro, Burton, Gerardo
Formato: artículo
Estado:Versión publicada
Fecha de publicación:2005
País:Argentina
Recursos:Consejo Nacional de Investigaciones Científicas y Técnicas
Repositorio:CONICET Digital (CONICET)
Idioma:inglés
OAI Identifier:oai:ri.conicet.gov.ar:11336/98780
Acesso em linha:http://hdl.handle.net/11336/98780
Access Level:acceso abierto
Palavra-chave:steroid analogs
https://purl.org/becyt/ford/3.5
https://purl.org/becyt/ford/3
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spelling 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 Técnicas2024-05-08T14:19:33Zoai: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:34982024-05-08 14:19:34.203CONICET 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
https://purl.org/becyt/ford/3.5
https://purl.org/becyt/ford/3
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
https://purl.org/becyt/ford/3.5
https://purl.org/becyt/ford/3
topic steroid analogs
https://purl.org/becyt/ford/3.5
https://purl.org/becyt/ford/3
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
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
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 15,811543

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