Antiviral activity of natural and synthetic brassinosteroids

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Since the discovery of brassinolide, a C28 steroid with an unusual lactone B-ring structure, more than 60 related compounds -collectively known as brassinosteroids (BRs) - have been isolated from a wide variety of plant species. Exogenous application of BRs to plants at nanomolar to micromolar conce...

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Autor principal: Wachsman, M.B
Otros Autores: Ramírez, Javier Alberto, Talarico, L.B, Galagovsky, L.R, Coto, C.E
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: 2004
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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024 7 |2 cas  |a aciclovir, 59277-89-3; brassinolide, 72962-43-7; foscarnet, 4428-95-9; lactone, 1338-03-0; ribavirin, 36791-04-5; stigmasterol, 83-48-7 
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245 1 0 |a Antiviral activity of natural and synthetic brassinosteroids 
260 |c 2004 
270 1 0 |m Wachsman, M.B.; Laboratorio de Virología, Departamento de Quimica Biologica, Universidad de Buenos Aires, Pabellón 2, Piso 4, 1428 Buenos Aires, Argentina; email: wachsman@qb.fcen.uba.ar 
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506 |2 openaire  |e Política editorial 
520 3 |a Since the discovery of brassinolide, a C28 steroid with an unusual lactone B-ring structure, more than 60 related compounds -collectively known as brassinosteroids (BRs) - have been isolated from a wide variety of plant species. Exogenous application of BRs to plants at nanomolar to micromolar concentrations has a broad spectrum of growth responses, such as stem elongation, inhibition of root growth, promotion of cell division and enhancement of stress resistance, brought about by changes in enzyme activity and gene expression. In the last years, biochemical and genetic analysis provided compelling evidence for an essential role of BRs in plant development. In this paper, we review our synthetic methods to obtain BRs analogues and report the scope of antiviral activity of these compounds against RNA and DNA viruses. Some of the compounds showed selectivity indexes (SI) 10- to 18- fold higher than ribavirin, a broad spectrum antiviral compound, when tested against Junin virus (JV) (Arenaviridae); a good antiviral activity against measles virus (MV) (Paramixoviridae), with SI values also higher than ribavirin used as reference drug, and a similar or lower activity against herpes simplex type 1 and 2 (HSV-1 and HSV-2) (Herpesviridae) when compared to foscarnet or acyclovir, respectively. Structure activity relationship studies (SAR) are analyzed, in order to detect which stereochemistry, type and position of functional groups are needed to develop a selective class of virus inhibitors. © 2004 Bentham Science Publishers Ltd.  |l eng 
593 |a Laboratorio de Virología, Departamento de Quimica Biologica, Universidad de Buenos Aires, Pabellón 2, Piso 4, 1428 Buenos Aires, Argentina 
593 |a Departamento de Quimica Organica, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, Piso 4, 1428 Buenos Aires, Argentina 
690 1 0 |a ANTIVIRAL 
690 1 0 |a ARENAVIRIDAE 
690 1 0 |a BRASSINOSTEROIDS DERIVATIVES 
690 1 0 |a HERPES SIMPLEX VIRUS 
690 1 0 |a MEASLES VIRUS 
690 1 0 |a 2 ALPHA 3 ALPHA 22,23 TETRAHYDROXY 5 ALPHA STIGMASTAN 6 ONE 
690 1 0 |a 2 ALPHA 3 ALPHA 22,23 TETRAHYDROXY HOMO 7 OXASTIGMASTAN 6 ONE 
690 1 0 |a 2 ALPHA 3 ALPHA 5 ALPHA 22,23 PENTAHYDROXYSTIGMATAN 6 ONE 
690 1 0 |a 2 ALPHA 3 ALPHA DIHYDROXY 5 ALPHA STIGMAST 22 EN 6 ONE 
690 1 0 |a 2 ALPHA 3 ALPHA DIHYDROXY 6 ALPHA FLUORO 5 ALPHA STIGMAST 22 ENE 
690 1 0 |a 2,3,22,23 BISACETYLIDEN 2 ALPHA 3 ALPHA 22,23 TETRAHYDROXY 5 ALPHA SIGMASTAN 6 ONE 
690 1 0 |a 3 ALPHA 22,23 TRIHYDROXY 5 ALPHA STIGMASTAN 6 ONE 
690 1 0 |a 3 ALPHA FLUORO 22,23 DIHYDROXY 5 ALPHA STIGMASTAN 6 ONE 
690 1 0 |a 3 BETA 5 ALPHA DIHYDROXYSTIGMAST 22 EN 6 ONE 
690 1 0 |a 3 BETA ACETOXY 22,23 DIHYDROXY 5 ALPHA STIGMASTAN 6 ONE 
690 1 0 |a 3 BETA ACETOXY 22,23 TRIHYDROXY 5 ALPHA STIGMASTAN 6 ONE 
690 1 0 |a 3 BETA ACETOXY 5 ALPHA 22,23 TRIHYDROSTIGMASTAN 6 ONE 
690 1 0 |a 3 BETA BROMO 5 ALPHA 22,23 TRIHYDROXYSTIGMASTAN 6 ONE 
690 1 0 |a 3 BETA BROMO 5 ALPHA HYDROXYSTIGMAST 22 EN 6 ONE 
690 1 0 |a 3 BETA FLUORO 5 ALPHA 22,23 TRIHYDROXYSTIGMASTAN 6 ONE 
690 1 0 |a ACICLOVIR 
690 1 0 |a BRASSINOLIDE 
690 1 0 |a BRASSINOSTEROID 
690 1 0 |a EPOXIDE 
690 1 0 |a FOSCARNET 
690 1 0 |a LACTONE 
690 1 0 |a ORTHOESTEROL A 
690 1 0 |a ORTHOESTEROL B 
690 1 0 |a ORTHOESTEROL C 
690 1 0 |a PHYTOSTEROL 
690 1 0 |a RIBAVIRIN 
690 1 0 |a STIGMASTEROL 
690 1 0 |a UNCLASSIFIED DRUG 
690 1 0 |a UNINDEXED DRUG 
690 1 0 |a WEIBENSTEROL A 
690 1 0 |a WEIBENSTEROL B 
690 1 0 |a ANTIVIRAL ACTIVITY 
690 1 0 |a ARENAVIRUS 
690 1 0 |a CELL DIVISION 
690 1 0 |a CHEMICAL ANALYSIS 
690 1 0 |a DNA VIRUS 
690 1 0 |a DRUG CLASSIFICATION 
690 1 0 |a DRUG ISOLATION 
690 1 0 |a DRUG SELECTIVITY 
690 1 0 |a DRUG SYNTHESIS 
690 1 0 |a ENZYME ACTIVITY 
690 1 0 |a GENE EXPRESSION 
690 1 0 |a GENETIC ANALYSIS 
690 1 0 |a HERPES SIMPLEX VIRUS 1 
690 1 0 |a HERPES SIMPLEX VIRUS 2 
690 1 0 |a JUNIN VIRUS 
690 1 0 |a MEASLES VIRUS 
690 1 0 |a NONHUMAN 
690 1 0 |a PARAMYXOVIRUS 
690 1 0 |a PLANT 
690 1 0 |a PLANT DEVELOPMENT 
690 1 0 |a PLANT STRESS 
690 1 0 |a REVIEW 
690 1 0 |a RNA VIRUS 
690 1 0 |a ROOT GROWTH 
690 1 0 |a STEM ELONGATION 
690 1 0 |a STEREOCHEMISTRY 
690 1 0 |a STRUCTURE ACTIVITY RELATION 
700 1 |a Ramírez, Javier Alberto 
700 1 |a Talarico, L.B. 
700 1 |a Galagovsky, L.R. 
700 1 |a Coto, C.E. 
773 0 |d 2004  |g v. 3  |h pp. 163-179  |k n. 2  |p Curr. Med. Chem.: Anti-Infect. Agents  |x 15680126  |t Current Medicinal Chemistry: Anti-Infective Agents 
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