Antiviral effect of brassinosteroids against herpes virus and arenaviruses

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A natural brassinosteroid and a series of synthetic derivatives were found to be good inhibitors of herpes simplex virus type 1 (HSV-1) and arenavirus replication in cell culture. The synthetic compounds tested were analogues of the 24(S) ethylbrassinone. Compounds (22R,23R,24S)-2α, 3α,5α,22,23-pent...

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Autor principal: Wachsman, M.B
Otros Autores: López, E.M.F, Ramírez, Javier Alberto, Galagovsky, L.R, Coto, C.E
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: International Medical Press Ltd 2000
Acceso en línea:Registro en Scopus
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Biblioteca Central Dr. Luis F. Leloir (FCEN) de Universidad de Buenos Aires
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100 1 |a Wachsman, M.B. 
245 1 0 |a Antiviral effect of brassinosteroids against herpes virus and arenaviruses 
260 |b International Medical Press Ltd  |c 2000 
270 1 0 |m Wachsman, M.B.; Laboratorio de Virologia, Departamento de Quimica Biologica, Universidad de Buenos Aires, Ciudad Universitaria, 1428 Buenos Aires, Argentina; email: wachsman@qb.fcen.uba.ar 
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504 |a Brosa, C., Biological effects of brassinosteroids (1997) Biochemistry and Functions of Sterols, pp. 201-220. , Edited by EJ Parish and D Nes. Boca Raton: CRC Press 
504 |a Brosa, C., Zamora, I., Terricabras, E., Soca, L., Peracaula, R., Rodríguez-Santamarta, C., Synthesis and molecular modeling: Related approaches to progress in brassinosteroid research (1997) Lipids, 32, pp. 1341-1347 
504 |a Caballero, G.M., Gros, E.G., Teme Centurión, O.M., Galagovsky, L.R., FAB mass spectrometry of brassinosteroids analogues (1997) Journal of the American Mass Spectroscopy Society, 8, pp. 270-274 
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504 |a Enria, D.A., Briggiler, A.M., Levis, S., Vallejos, D., Maiztegui, J.I., Canonico, P.G., Tolerance and antiviral effect of ribavirin in patients with Argentine hemorrhagic fever (1987) Antiviral Research, 7, pp. 353-359 
504 |a Enria, D.A., Maiztegui, J.I., Antiviral treatment of Argentine hemorrhagic fever (1994) Antiviral Research, 23, pp. 23-31 
504 |a Fujioka, S., Sakurai, A., Brassinosteroids (1997) Natural Product Reports, 14, pp. 1-10 
504 |a Jacobsen, E.N., Marko, I., Mungall, W.S., Schroder, G., Sharpless, K.B., Asymmetric dihydroxylation via ligand-accelerated catalysis (1988) Journal of the American Chemical Society, 110, pp. 1968-1970 
504 |a Kenyon, R.H., Canonico, P.G., Green, D.E., Peters, C.J., Effect of ribavirin and tributylribavirin on Argentine hemorrhagic fever (Junin Virus) in guinea pigs (1986) Antimicrobial Agents and Chemotherapy, 29, pp. 521-523 
504 |a McMorris, T.C., Recent developments in the field of plant steroids hormones (1997) Lipids, 32, pp. 1303-1308 
504 |a McMorris, T.C., Patil, T.A., Chavez, R.G., Baker, M.E., Clouse, S.D., Synthesis and biological activity of 28-homobrassinolide and analogs (1994) Phytochemistry, 36, pp. 585-589 
504 |a Rodriguez, M., McCormick, J.B., Weissenbacher, M.C., Antiviral effect of ribavirin on Junin virus replication in vitro (1986) Revista Argentina de Microbiología, 18, pp. 69-74 
504 |a Sidwell, R.W., Ribavirin. In vitro antiviral activity (1980) Ribavirin, a Broad Spectrum Antiviral Agent, pp. 23-42. , Edited by RA Smith and W Kirpatrick W. New York: Academic Press 
504 |a Teme Centurión, O.M., Galagovsky, L.R., Alternative synthesis of 24(S)-homoethylcastasterone from stigmasterol (1998) Anales de la Asociación Química Argentina, 86, pp. 104-109 
504 |a Wada, K., Marumo, S., Abe, H., Marishita, T., Nakamura, R., Uchishama, M., Mori, K., A rice lamina inclination test. A micro-quantitative bioassay for brassinosteroids (1984) Agricultural Biologycal Chemistry, 48, pp. 719-726 
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506 |2 openaire  |e Política editorial 
520 3 |a A natural brassinosteroid and a series of synthetic derivatives were found to be good inhibitors of herpes simplex virus type 1 (HSV-1) and arenavirus replication in cell culture. The synthetic compounds tested were analogues of the 24(S) ethylbrassinone. Compounds (22R,23R,24S)-2α, 3α,5α,22,23-pentahydroxy-stigmastan-6-one and (22R,23R,24S)-3β-bromo-5α,22,23-trihydroxy stigm-astan-6-one were cytotoxic at concentrations of 20-40 μM. (22S,23S,24S)-2α,3α,22,23-tetrahydroxy-5α,stigmastan-6-one, (22R,23R,24S)-3β-acetoxy-22,23-dihydroxy-5α-cholestan-6-one, (22S,23S,24S)-3β-bromo-22,23-dihydroxy-5α-chol-estan-6-one and (22S,23S,24S)-3β-bromo-5α,22,23-trihydroxy-stigmastan-6-one were the most active of the series against HSV-1, with selectivity index (SI) values (CC50/EC50) ranging from 10.6 to 16.5. The majority of the compounds were potent inhibitors of arenaviruses, (22S,23S,24S)-3β-bromo-5α,22,23-trihydroxy-stig-mastan-6-one being the most active, with SI values of 307.8 and 692.5 for Tacaribe and Junin viruses, respectively. The antiviral activity of brassinosteroid derivatives was not because of direct inactivation; time-of-addition experiments suggested that a late step in HSV-1 multiplication was affected, whereas arenaviruses remained susceptible to the compounds throughout the replicative cycle.  |l eng 
593 |a Laboratorio de Virología, Depto. de Quim. Biológica, Universidad de Buenos Aires, Ciudad Universitaria, 1428 Buenos Aires, Argentina 
593 |a Depto. de Quim. Orgánica, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, 1428 Buenos Aires, Argentina 
690 1 0 |a ARENAVIRUSES 
690 1 0 |a BRASSINOSTEROIDS 
690 1 0 |a HERPES SIMPLEX VIRUS TYPE 1 
690 1 0 |a JUNIN VIRUS 
690 1 0 |a ACICLOVIR 
690 1 0 |a ANTIVIRUS AGENT 
690 1 0 |a BRASSINOSTEROID 
690 1 0 |a ANIMAL CELL 
690 1 0 |a ANTIVIRAL ACTIVITY 
690 1 0 |a ARENAVIRUS 
690 1 0 |a ARTICLE 
690 1 0 |a CONTROLLED STUDY 
690 1 0 |a DRUG CYTOTOXICITY 
690 1 0 |a HERPES SIMPLEX VIRUS 1 
690 1 0 |a HERPES VIRUS 
690 1 0 |a JUNIN VIRUS 
690 1 0 |a NONHUMAN 
690 1 0 |a PRIORITY JOURNAL 
690 1 0 |a VERO CELL 
690 1 0 |a VIROGENESIS 
690 1 0 |a VIRUS REPLICATION 
700 1 |a López, E.M.F. 
700 1 |a Ramírez, Javier Alberto 
700 1 |a Galagovsky, L.R. 
700 1 |a Coto, C.E. 
773 0 |d International Medical Press Ltd, 2000  |g v. 11  |h pp. 71-77  |k n. 1  |p Antiviral Chem. Chemother.  |x 09563202  |t Antiviral Chemistry and Chemotherapy 
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