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Ramírez, J.A.; Bruttomesso, A.C.; Michelini, F.M.; Acebedo, S.L.; Alché, L.E.; Galagovsky, L.R. "Syntheses of immunomodulating androstanes and stigmastanes: Comparison of their TNF-α inhibitory activity" (2007) Bioorganic and Medicinal Chemistry. 15(24):7538-7544
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Abstract:

In a previous work our group showed that some synthetic stigmastanes may play a role in immune-mediated inflammation. In this paper we report the syntheses of a series of new steroidal compounds derived from dehydroepiandrosterone and stigmasterol, and the evaluation of their in vitro inhibitory activity of the TNF-α production by macrophages. A preliminary qualitative structure-activity relationship was established. © 2007 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Syntheses of immunomodulating androstanes and stigmastanes: Comparison of their TNF-α inhibitory activity
Autor:Ramírez, J.A.; Bruttomesso, A.C.; Michelini, F.M.; Acebedo, S.L.; Alché, L.E.; Galagovsky, L.R.
Filiación:Departamento de Quimica Organica and UMYMFOR (CONICET-Facultad de Ciencias Exactas y Naturales), Universidad de Buenos Aires, Pabellon 2, Piso 3, Ciudad Universitaria, C1428EGA Buenos Aires, Argentina
Laboratorio de Virología: Agentes Antivirales y Citoprotectores, Departamento de Química Biológica, Facultad de Ciencias Exactas y Naturales, Pabellon 2, Piso 4, Ciudad Universitaria, C1428EGA Buenos Aires, Argentina
Palabras clave:Androstane; DHEA; Immune regulation; Steroids; Stigmastane; Tumor necrosis factor-α; 3beta bromo 5 hydroxy 5alpha androstane 6,17 dione; 3beta bromo 5 hydroxy dextro homo 17alpha oxa 5alpha androstane 6,17 dione; 3beta bromo 5alpha,6alpha epoxy dextro homo 17alpha oxaandrostan 17 one; 3beta bromo 5alpha,6alpha epoxyandrostan 17 one; 3beta bromostigmast 5 ene 22,23 diol; 3beta chlorostigmast 5 ene 22,23 diol; 3beta fluoro 5 hydroxy 5alpha stigmast 22 en 6 one; 3beta fluoro 5,22,23 trihydroxy 5alpha stigmastan 6 one; 3beta fluorostigmast 5 ene 22,23 diol; 3beta,5 dihydroxy 5alpha androstane 6,17 dione; androstane derivative; prasterone; steroid; stigmast 5 ene 3beta,22,23 triol; stigmasterol; tumor necrosis factor alpha; unclassified drug; animal cell; article; controlled study; drug activity; drug inhibition; in vitro study; macrophage; nonhuman; structure activity relation; Androstanes; Animals; Cell Line; Cholestanes; Dehydroepiandrosterone; Drug Evaluation, Preclinical; Immunologic Factors; Mice; Molecular Structure; Stigmasterol; Structure-Activity Relationship; Tumor Necrosis Factor-alpha
Año:2007
Volumen:15
Número:24
Página de inicio:7538
Página de fin:7544
DOI: http://dx.doi.org/10.1016/j.bmc.2007.09.012
Título revista:Bioorganic and Medicinal Chemistry
Título revista abreviado:Bioorg. Med. Chem.
ISSN:09680896
CODEN:BMECE
CAS:prasterone, 53-43-0; stigmasterol, 83-48-7; Androstanes; Cholestanes; Dehydroepiandrosterone, 53-43-0; Immunologic Factors; Stigmasterol, 83-48-7; Tumor Necrosis Factor-alpha
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09680896_v15_n24_p7538_Ramirez

Referencias:

  • Corral, L.G., Kaplan, G., (1999) Ann. Rheum. Dis., 58, p. 107
  • Magna, A.M., Takiya, C.M., Aruda, L.B., Pascarelli, B., Gomes, R.N., Faria, H.C., Lima, L.M., Barreiro, E.J., (2005) Int. Immunopharmacol., 5, p. 485
  • Kipper-Gaiperin, M., Galilly, R., Danenberg, H.D., Brenner, T., (1999) Int. J. Dev. Neurosci., 17, p. 765
  • Kim, S.K., Shin, M.S., Jung, B.K., Shim, J.Y., Won, H.S., Lee, P.R., Kim, A.., (2006) J. Reprod. Immunol., 70, p. 71
  • Loria, R.M., Regelson, W., Padgett, D.A., (1990) The Biologic Role of Dehydroepiandrosterone DHEA, pp. 107-130. , Kalimi M., and Regelson W. (Eds), Walter De Gruyter, New York
  • De Jonga, A., Plata, J., Mensink, R.P., (2003) J. Nutr. Biochem., 14, p. 362
  • Bouic, P.J.D., (2001) Curr. Opin. Clin. Nutr. Metab. Care, 4, p. 471
  • Michelini, F.M., Ramírez, J.A., Berra, A., Galagovsky, L.R., Alché, L.E., (2004) Steroids, 69, p. 713
  • Bose, A.K., Bansi, L., (1973) Tetrahedron Lett., 40, p. 3937
  • Hellrung, B., Voigt, B., Schmidt, J., Adam, G., (1997) Steroids, 62, p. 415
  • Galagovsky, L.R., Gros, E.G., Ramírez, J.A., (2001) Phytochemistry, 58, p. 973
  • Syamala, A., Baskaran, S., Chandrasekaran, S., (1992) J. Org. Chem., 57, p. 1928
  • Porzel, A., Marquandt, V., Adam, G., (1992) Magn. Reson. Chem., 30, p. 651
  • Hogan, M.M., Vogel, S.N., (1992) Current Protocols in Immunology, 6, p. 1. , Coligan J.E., Kruisbeek A.M., Margulies D.H., Shevach E.M., and Strober W. (Eds), Wiley, New York
  • Joyce, D.A., Steer, J.H., Abraham, L.J., (1997) Inflamm. Res., 46, p. 447
  • Dawidar, A.M., Saleh, A.A., Abdel-Malek, M.M., (1980) Z. Naturforsch., B: Anorg. Chem., Org. Chem., 35 b, p. 102
  • Denizot, F., Lang, R., (1986) J. Immunol. Methods, 89, p. 271
  • Decker, T., Lohmann-Mathess, M.L., Gifford, G.E., (1987) J. Immunol., 138, p. 957

Citas:

---------- APA ----------
Ramírez, J.A., Bruttomesso, A.C., Michelini, F.M., Acebedo, S.L., Alché, L.E. & Galagovsky, L.R. (2007) . Syntheses of immunomodulating androstanes and stigmastanes: Comparison of their TNF-α inhibitory activity. Bioorganic and Medicinal Chemistry, 15(24), 7538-7544.
http://dx.doi.org/10.1016/j.bmc.2007.09.012
---------- CHICAGO ----------
Ramírez, J.A., Bruttomesso, A.C., Michelini, F.M., Acebedo, S.L., Alché, L.E., Galagovsky, L.R. "Syntheses of immunomodulating androstanes and stigmastanes: Comparison of their TNF-α inhibitory activity" . Bioorganic and Medicinal Chemistry 15, no. 24 (2007) : 7538-7544.
http://dx.doi.org/10.1016/j.bmc.2007.09.012
---------- MLA ----------
Ramírez, J.A., Bruttomesso, A.C., Michelini, F.M., Acebedo, S.L., Alché, L.E., Galagovsky, L.R. "Syntheses of immunomodulating androstanes and stigmastanes: Comparison of their TNF-α inhibitory activity" . Bioorganic and Medicinal Chemistry, vol. 15, no. 24, 2007, pp. 7538-7544.
http://dx.doi.org/10.1016/j.bmc.2007.09.012
---------- VANCOUVER ----------
Ramírez, J.A., Bruttomesso, A.C., Michelini, F.M., Acebedo, S.L., Alché, L.E., Galagovsky, L.R. Syntheses of immunomodulating androstanes and stigmastanes: Comparison of their TNF-α inhibitory activity. Bioorg. Med. Chem. 2007;15(24):7538-7544.
http://dx.doi.org/10.1016/j.bmc.2007.09.012