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Wachsman, M.B.; Ramírez, J.A.; Talarico, L.B.; Galagovsky, L.R.; Coto, C.E. "Antiviral activity of natural and synthetic brassinosteroids" (2004) Current Medicinal Chemistry: Anti-Infective Agents. 3(2):163-179
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Abstract:

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.

Registro:

Documento: Artículo
Título:Antiviral activity of natural and synthetic brassinosteroids
Autor:Wachsman, M.B.; Ramírez, J.A.; Talarico, L.B.; Galagovsky, L.R.; Coto, C.E.
Filiación:Laboratorio de Virología, Departamento de Quimica Biologica, Universidad de Buenos Aires, Pabellón 2, Piso 4, 1428 Buenos Aires, Argentina
Departamento de Quimica Organica, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, Piso 4, 1428 Buenos Aires, Argentina
Palabras clave:Antiviral; Arenaviridae; Brassinosteroids derivatives; Herpes simplex virus; Measles virus; 2 alpha 3 alpha 22,23 tetrahydroxy 5 alpha stigmastan 6 one; 2 alpha 3 alpha 22,23 tetrahydroxy homo 7 oxastigmastan 6 one; 2 alpha 3 alpha 5 alpha 22,23 pentahydroxystigmatan 6 one; 2 alpha 3 alpha dihydroxy 5 alpha stigmast 22 en 6 one; 2 alpha 3 alpha dihydroxy 6 alpha fluoro 5 alpha stigmast 22 ene; 2,3,22,23 bisacetyliden 2 alpha 3 alpha 22,23 tetrahydroxy 5 alpha sigmastan 6 one; 3 alpha 22,23 trihydroxy 5 alpha stigmastan 6 one; 3 alpha fluoro 22,23 dihydroxy 5 alpha stigmastan 6 one; 3 beta 5 alpha dihydroxystigmast 22 en 6 one; 3 beta acetoxy 22,23 dihydroxy 5 alpha stigmastan 6 one; 3 beta acetoxy 22,23 trihydroxy 5 alpha stigmastan 6 one; 3 beta acetoxy 5 alpha 22,23 trihydrostigmastan 6 one; 3 beta bromo 5 alpha 22,23 trihydroxystigmastan 6 one; 3 beta bromo 5 alpha hydroxystigmast 22 en 6 one; 3 beta fluoro 5 alpha 22,23 trihydroxystigmastan 6 one; aciclovir; brassinolide; brassinosteroid; epoxide; foscarnet; lactone; orthoesterol A; orthoesterol B; orthoesterol C; phytosterol; ribavirin; stigmasterol; unclassified drug; unindexed drug; weibensterol A; weibensterol B; antiviral activity; Arenavirus; cell division; chemical analysis; DNA virus; drug classification; drug isolation; drug selectivity; drug synthesis; enzyme activity; gene expression; genetic analysis; Herpes simplex virus 1; Herpes simplex virus 2; Junin virus; Measles virus; nonhuman; Paramyxovirus; plant; plant development; plant stress; review; RNA virus; root growth; stem elongation; stereochemistry; structure activity relation
Año:2004
Volumen:3
Número:2
Página de inicio:163
Página de fin:179
DOI: http://dx.doi.org/10.2174/1568012043354026
Título revista:Current Medicinal Chemistry: Anti-Infective Agents
Título revista abreviado:Curr. Med. Chem.: Anti-Infect. Agents
ISSN:15680126
CODEN:CMCAF
CAS:aciclovir, 59277-89-3; brassinolide, 72962-43-7; foscarnet, 4428-95-9; lactone, 1338-03-0; ribavirin, 36791-04-5; stigmasterol, 83-48-7
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_15680126_v3_n2_p163_Wachsman

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Citas:

---------- APA ----------
Wachsman, M.B., Ramírez, J.A., Talarico, L.B., Galagovsky, L.R. & Coto, C.E. (2004) . Antiviral activity of natural and synthetic brassinosteroids. Current Medicinal Chemistry: Anti-Infective Agents, 3(2), 163-179.
http://dx.doi.org/10.2174/1568012043354026
---------- CHICAGO ----------
Wachsman, M.B., Ramírez, J.A., Talarico, L.B., Galagovsky, L.R., Coto, C.E. "Antiviral activity of natural and synthetic brassinosteroids" . Current Medicinal Chemistry: Anti-Infective Agents 3, no. 2 (2004) : 163-179.
http://dx.doi.org/10.2174/1568012043354026
---------- MLA ----------
Wachsman, M.B., Ramírez, J.A., Talarico, L.B., Galagovsky, L.R., Coto, C.E. "Antiviral activity of natural and synthetic brassinosteroids" . Current Medicinal Chemistry: Anti-Infective Agents, vol. 3, no. 2, 2004, pp. 163-179.
http://dx.doi.org/10.2174/1568012043354026
---------- VANCOUVER ----------
Wachsman, M.B., Ramírez, J.A., Talarico, L.B., Galagovsky, L.R., Coto, C.E. Antiviral activity of natural and synthetic brassinosteroids. Curr. Med. Chem.: Anti-Infect. Agents. 2004;3(2):163-179.
http://dx.doi.org/10.2174/1568012043354026