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...
| Autores: | , , , , , , |
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| Tipo de recurso: | artículo |
| Estado: | Versión publicada |
| Fecha de publicación: | 2005 |
| País: | Argentina |
| Institución: | Consejo Nacional de Investigaciones Científicas y Técnicas |
| Repositorio: | CONICET Digital (CONICET) |
| Idioma: | inglés |
| OAI Identifier: | oai:ri.conicet.gov.ar:11336/98780 |
| Acceso en línea: | http://hdl.handle.net/11336/98780 |
| Access Level: | acceso abierto |
| Palabra clave: | steroid analogs https://purl.org/becyt/ford/3.5 https://purl.org/becyt/ford/3 |
| Sumario: | 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. |
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