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" (2005) Journal of Medicinal Chemistry. 48(18):5675-5683
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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.


Documento: Artículo
Título:6,19-Sulfur-bridged progesterone analogues with antiimmunosuppressive activity
Autor:Veleiro, A.S.; Pecci, A.; Monteserín, M.C.; Baggio, R.; Garland, M.T.; Lantos, C.P.; Burton, G.
Filiación:Departamento de Química Orgánica, UMYMFOR (CONICET-FCEN), Universidad de Buenos Aires, C1428EGA Buenos Aires, Argentina
Departamento de Química Biológica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, C1428EGA Buenos Aires, Argentina
Departamento de Física, Facultad de Ciencias Físicas y Matemáticas, Universidad de Chile, Av. Blanco Encalada 2008, Santiago, Chile
Departamento de Física, Comisión Nacional de Energía Atómica, Av. del Libertador 8250, C1429 Buenos Aires, Argentina
Palabras clave: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
Página de inicio:5675
Página de fin:5683
Título revista:Journal of Medicinal Chemistry
Título revista abreviado:J. Med. Chem.
CAS:dexamethasone, 50-02-2; fluorescein isothiocyanate, 25168-13-2, 27072-45-3, 3326-32-7; lipocortin 5, 111237-10-6; 21-hydroxy-6,19-epithiopregn-4-ene-3,20-dione; Desoxycorticosterone, 64-85-7; Dexamethasone, 50-02-2; Glucocorticoids; NF-kappa B; Progesterone, 57-83-0; Receptors, Progesterone; Sulfides; Tumor Necrosis Factor-alpha


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---------- APA ----------
Veleiro, A.S., Pecci, A., Monteserín, M.C., Baggio, R., Garland, M.T., Lantos, C.P. & Burton, G. (2005) . 6,19-Sulfur-bridged progesterone analogues with antiimmunosuppressive activity. Journal of Medicinal Chemistry, 48(18), 5675-5683.
---------- CHICAGO ----------
Veleiro, A.S., Pecci, A., Monteserín, M.C., Baggio, R., Garland, M.T., Lantos, C.P., et al. "6,19-Sulfur-bridged progesterone analogues with antiimmunosuppressive activity" . Journal of Medicinal Chemistry 48, no. 18 (2005) : 5675-5683.
---------- MLA ----------
Veleiro, A.S., Pecci, A., Monteserín, M.C., Baggio, R., Garland, M.T., Lantos, C.P., et al. "6,19-Sulfur-bridged progesterone analogues with antiimmunosuppressive activity" . Journal of Medicinal Chemistry, vol. 48, no. 18, 2005, pp. 5675-5683.
---------- VANCOUVER ----------
Veleiro, A.S., Pecci, A., Monteserín, M.C., Baggio, R., Garland, M.T., Lantos, C.P., et al. 6,19-Sulfur-bridged progesterone analogues with antiimmunosuppressive activity. J. Med. Chem. 2005;48(18):5675-5683.