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 principales:	Veleiro, A.S., Pecci, A., Monteserín, M.C., Baggio, R., Garland, M.T., Lantos, C.P., Burton, G.
Formato:	JOUR
Materias:	19 sulfanylpregn 5 ene 21 hydroxy 6,19 epithioprogesterone 21 hydroxy 6,19 epithioprogesterone s,s dioxide 6,19 epithioprogesterone dexamethasone fluorescein isothiocyanate immunoglobulin enhancer binding protein lipocortin 5 progesterone derivative sulfur derivative tumor necrosis factor alpha unclassified drug animal cell antiimmunosuppressive activity apoptosis article controlled study cyclization drug activity drug structure drug synthesis enzyme inhibition HeLa cell human human cell iodination nonhuman parameter rat structure analysis thymocyte Animals Apoptosis Cercopithecus aethiops COS Cells Desoxycorticosterone Dexamethasone Glucocorticoids Hela Cells Humans Immune Tolerance Male Mice Molecular Conformation Molecular Structure NF-kappa B Progesterone Rats Rats, Sprague-Dawley Receptors, Progesterone Stereoisomerism Structure-Activity Relationship Sulfides Thymus Gland Tumor Necrosis Factor-alpha
Acceso en línea:	http://hdl.handle.net/20.500.12110/paper_00222623_v48_n18_p5675_Veleiro
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

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spelling	todo:paper_00222623_v48_n18_p5675_Veleiro2023-10-03T14:30:15Z 6,19-Sulfur-bridged progesterone analogues with antiimmunosuppressive activity Veleiro, A.S. Pecci, A. Monteserín, M.C. Baggio, R. Garland, M.T. Lantos, C.P. Burton, G. 19 sulfanylpregn 5 ene 21 hydroxy 6,19 epithioprogesterone 21 hydroxy 6,19 epithioprogesterone s,s dioxide 6,19 epithioprogesterone dexamethasone fluorescein isothiocyanate immunoglobulin enhancer binding protein lipocortin 5 progesterone derivative sulfur derivative tumor necrosis factor alpha unclassified drug animal cell antiimmunosuppressive activity apoptosis article controlled study cyclization drug activity drug structure drug synthesis enzyme inhibition HeLa cell human human cell iodination nonhuman parameter rat structure analysis thymocyte Animals Apoptosis Cercopithecus aethiops COS Cells Desoxycorticosterone Dexamethasone Glucocorticoids Hela Cells Humans Immune Tolerance Male Mice Molecular Conformation Molecular Structure NF-kappa B Progesterone Rats Rats, Sprague-Dawley Receptors, Progesterone Stereoisomerism Structure-Activity Relationship Sulfides Thymus Gland Tumor Necrosis Factor-alpha 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, A.S. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Pecci, A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Burton, G. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_00222623_v48_n18_p5675_Veleiro
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	19 sulfanylpregn 5 ene 21 hydroxy 6,19 epithioprogesterone 21 hydroxy 6,19 epithioprogesterone s,s dioxide 6,19 epithioprogesterone dexamethasone fluorescein isothiocyanate immunoglobulin enhancer binding protein lipocortin 5 progesterone derivative sulfur derivative tumor necrosis factor alpha unclassified drug animal cell antiimmunosuppressive activity apoptosis article controlled study cyclization drug activity drug structure drug synthesis enzyme inhibition HeLa cell human human cell iodination nonhuman parameter rat structure analysis thymocyte Animals Apoptosis Cercopithecus aethiops COS Cells Desoxycorticosterone Dexamethasone Glucocorticoids Hela Cells Humans Immune Tolerance Male Mice Molecular Conformation Molecular Structure NF-kappa B Progesterone Rats Rats, Sprague-Dawley Receptors, Progesterone Stereoisomerism Structure-Activity Relationship Sulfides Thymus Gland Tumor Necrosis Factor-alpha
spellingShingle	19 sulfanylpregn 5 ene 21 hydroxy 6,19 epithioprogesterone 21 hydroxy 6,19 epithioprogesterone s,s dioxide 6,19 epithioprogesterone dexamethasone fluorescein isothiocyanate immunoglobulin enhancer binding protein lipocortin 5 progesterone derivative sulfur derivative tumor necrosis factor alpha unclassified drug animal cell antiimmunosuppressive activity apoptosis article controlled study cyclization drug activity drug structure drug synthesis enzyme inhibition HeLa cell human human cell iodination nonhuman parameter rat structure analysis thymocyte Animals Apoptosis Cercopithecus aethiops COS Cells Desoxycorticosterone Dexamethasone Glucocorticoids Hela Cells Humans Immune Tolerance Male Mice Molecular Conformation Molecular Structure NF-kappa B Progesterone Rats Rats, Sprague-Dawley Receptors, Progesterone Stereoisomerism Structure-Activity Relationship Sulfides Thymus Gland Tumor Necrosis Factor-alpha Veleiro, A.S. Pecci, A. Monteserín, M.C. Baggio, R. Garland, M.T. Lantos, C.P. Burton, G. 6,19-Sulfur-bridged progesterone analogues with antiimmunosuppressive activity
topic_facet	19 sulfanylpregn 5 ene 21 hydroxy 6,19 epithioprogesterone 21 hydroxy 6,19 epithioprogesterone s,s dioxide 6,19 epithioprogesterone dexamethasone fluorescein isothiocyanate immunoglobulin enhancer binding protein lipocortin 5 progesterone derivative sulfur derivative tumor necrosis factor alpha unclassified drug animal cell antiimmunosuppressive activity apoptosis article controlled study cyclization drug activity drug structure drug synthesis enzyme inhibition HeLa cell human human cell iodination nonhuman parameter rat structure analysis thymocyte Animals Apoptosis Cercopithecus aethiops COS Cells Desoxycorticosterone Dexamethasone Glucocorticoids Hela Cells Humans Immune Tolerance Male Mice Molecular Conformation Molecular Structure NF-kappa B Progesterone Rats Rats, Sprague-Dawley Receptors, Progesterone Stereoisomerism Structure-Activity Relationship Sulfides Thymus Gland Tumor Necrosis Factor-alpha
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.
format	JOUR
author	Veleiro, A.S. Pecci, A. Monteserín, M.C. Baggio, R. Garland, M.T. Lantos, C.P. Burton, G.
author_facet	Veleiro, A.S. Pecci, A. Monteserín, M.C. Baggio, R. Garland, M.T. Lantos, C.P. Burton, G.
author_sort	Veleiro, A.S.
title	6,19-Sulfur-bridged progesterone analogues with antiimmunosuppressive activity
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
url	http://hdl.handle.net/20.500.12110/paper_00222623_v48_n18_p5675_Veleiro
work_keys_str_mv	AT veleiroas 619sulfurbridgedprogesteroneanalogueswithantiimmunosuppressiveactivity AT peccia 619sulfurbridgedprogesteroneanalogueswithantiimmunosuppressiveactivity AT monteserinmc 619sulfurbridgedprogesteroneanalogueswithantiimmunosuppressiveactivity AT baggior 619sulfurbridgedprogesteroneanalogueswithantiimmunosuppressiveactivity AT garlandmt 619sulfurbridgedprogesteroneanalogueswithantiimmunosuppressiveactivity AT lantoscp 619sulfurbridgedprogesteroneanalogueswithantiimmunosuppressiveactivity AT burtong 619sulfurbridgedprogesteroneanalogueswithantiimmunosuppressiveactivity
_version_	1782024344050860032

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

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