Sterol analogues with diamide side chains interfere with the intracellular localization of viral glycoproteins

The need to develop novel antiviral agents encouraged us to assess the antiviral activity of synthetic sterol analogues with a diamide side chains. Cytotoxicity and antiviral activity of a family of azasterol previously synthesized was evaluated against herpes simplex virus 1 (HSV-1) (KOS and B2006)...

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Autores principales: Cabrera, Gabriela Myriam, Ramirez, Javier Alberto, Barquero, Andrea Alejandra
Publicado: 2012
Materias:
VSV
Acceso en línea:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0006291X_v427_n1_p107_Davola
http://hdl.handle.net/20.500.12110/paper_0006291X_v427_n1_p107_Davola
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spelling paper:paper_0006291X_v427_n1_p107_Davola2023-06-08T14:30:20Z Sterol analogues with diamide side chains interfere with the intracellular localization of viral glycoproteins Cabrera, Gabriela Myriam Ramirez, Javier Alberto Barquero, Andrea Alejandra Antiviral Azasterol Glycoprotein transport HSV-1 Ugi reaction VSV azacosterol diamide glycoprotein D n [(tert butylcarbamoyl)methyl] n (2 chlorophenyl) 3beta hydroxyandrost 5 ene 17beta carboxamide n [(tert butylcarbamoyl)methyl] n (2 ethyl 6 methylphenyl) 3beta hydroxyandrost 5 ene 17beta carboxamide n [(tert butylcarbamoyl)methyl] n (2 fluorophenyl) 3beta hydroxyandrost 5 ene 17beta carboxamide n [(tert butylcarbamoyl)methyl] n (3 trifluorophenyl) 3beta hydroxyandrost 5 ene 17beta carboxamide n [(tert butylcarbamoyl)methyl] n (3,4 dichlorophenyl) 3beta hydroxyandrost 5 ene 17beta carboxamide n [(tert butylcarbamoyl)methyl] n (4 fluorophenyl) 3beta hydroxyandrost 5 ene 17beta carboxamide n [(tert butylcarbamoyl)methyl] n (4 methoxyphenyl) 3beta hydroxyandrost 5 ene 17beta carboxamide n [(tert butylcarbamoyl)methyl] n (4 methylphenyl) 3beta hydroxyandrost 5 ene 17beta carboxamide unclassified drug virus glycoprotein animal cell antiviral activity article chemical reaction drug synthesis fluorescence analysis Herpes simplex virus 1 nonhuman priority journal protein localization virogenesis virus inhibition Antiviral Agents Diamide Herpesvirus 1, Human Humans Intracellular Space Sterols Viral Envelope Proteins Virus Replication Human herpesvirus 1 Vesicular stomatitis virus The need to develop novel antiviral agents encouraged us to assess the antiviral activity of synthetic sterol analogues with a diamide side chains. Cytotoxicity and antiviral activity of a family of azasterol previously synthesized was evaluated against herpes simplex virus 1 (HSV-1) (KOS and B2006) and vesicular stomatitis virus (VSV). This family of compounds was extended by the synthesis of novel analogs using an Ugi multicomponent reaction and their ability to inhibit viral multiplication was also evaluated. The results show that some of the compounds tested exert an antiviral activity. Besides, the effect of the azasterols on the intracellular localization of viral glycoproteins was examined. Strikingly, alteration on the glycoprotein D (gD) of HSV-1 fluorescence pattern was observed with both the antiherpetic compounds and the inactive azasterols. © 2012 Elsevier Inc. Fil:Cabrera, G.M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Ramírez, J.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Barquero, A.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2012 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0006291X_v427_n1_p107_Davola http://hdl.handle.net/20.500.12110/paper_0006291X_v427_n1_p107_Davola
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic Antiviral
Azasterol
Glycoprotein transport
HSV-1
Ugi reaction
VSV
azacosterol
diamide
glycoprotein D
n [(tert butylcarbamoyl)methyl] n (2 chlorophenyl) 3beta hydroxyandrost 5 ene 17beta carboxamide
n [(tert butylcarbamoyl)methyl] n (2 ethyl 6 methylphenyl) 3beta hydroxyandrost 5 ene 17beta carboxamide
n [(tert butylcarbamoyl)methyl] n (2 fluorophenyl) 3beta hydroxyandrost 5 ene 17beta carboxamide
n [(tert butylcarbamoyl)methyl] n (3 trifluorophenyl) 3beta hydroxyandrost 5 ene 17beta carboxamide
n [(tert butylcarbamoyl)methyl] n (3,4 dichlorophenyl) 3beta hydroxyandrost 5 ene 17beta carboxamide
n [(tert butylcarbamoyl)methyl] n (4 fluorophenyl) 3beta hydroxyandrost 5 ene 17beta carboxamide
n [(tert butylcarbamoyl)methyl] n (4 methoxyphenyl) 3beta hydroxyandrost 5 ene 17beta carboxamide
n [(tert butylcarbamoyl)methyl] n (4 methylphenyl) 3beta hydroxyandrost 5 ene 17beta carboxamide
unclassified drug
virus glycoprotein
animal cell
antiviral activity
article
chemical reaction
drug synthesis
fluorescence analysis
Herpes simplex virus 1
nonhuman
priority journal
protein localization
virogenesis
virus inhibition
Antiviral Agents
Diamide
Herpesvirus 1, Human
Humans
Intracellular Space
Sterols
Viral Envelope Proteins
Virus Replication
Human herpesvirus 1
Vesicular stomatitis virus
spellingShingle Antiviral
Azasterol
Glycoprotein transport
HSV-1
Ugi reaction
VSV
azacosterol
diamide
glycoprotein D
n [(tert butylcarbamoyl)methyl] n (2 chlorophenyl) 3beta hydroxyandrost 5 ene 17beta carboxamide
n [(tert butylcarbamoyl)methyl] n (2 ethyl 6 methylphenyl) 3beta hydroxyandrost 5 ene 17beta carboxamide
n [(tert butylcarbamoyl)methyl] n (2 fluorophenyl) 3beta hydroxyandrost 5 ene 17beta carboxamide
n [(tert butylcarbamoyl)methyl] n (3 trifluorophenyl) 3beta hydroxyandrost 5 ene 17beta carboxamide
n [(tert butylcarbamoyl)methyl] n (3,4 dichlorophenyl) 3beta hydroxyandrost 5 ene 17beta carboxamide
n [(tert butylcarbamoyl)methyl] n (4 fluorophenyl) 3beta hydroxyandrost 5 ene 17beta carboxamide
n [(tert butylcarbamoyl)methyl] n (4 methoxyphenyl) 3beta hydroxyandrost 5 ene 17beta carboxamide
n [(tert butylcarbamoyl)methyl] n (4 methylphenyl) 3beta hydroxyandrost 5 ene 17beta carboxamide
unclassified drug
virus glycoprotein
animal cell
antiviral activity
article
chemical reaction
drug synthesis
fluorescence analysis
Herpes simplex virus 1
nonhuman
priority journal
protein localization
virogenesis
virus inhibition
Antiviral Agents
Diamide
Herpesvirus 1, Human
Humans
Intracellular Space
Sterols
Viral Envelope Proteins
Virus Replication
Human herpesvirus 1
Vesicular stomatitis virus
Cabrera, Gabriela Myriam
Ramirez, Javier Alberto
Barquero, Andrea Alejandra
Sterol analogues with diamide side chains interfere with the intracellular localization of viral glycoproteins
topic_facet Antiviral
Azasterol
Glycoprotein transport
HSV-1
Ugi reaction
VSV
azacosterol
diamide
glycoprotein D
n [(tert butylcarbamoyl)methyl] n (2 chlorophenyl) 3beta hydroxyandrost 5 ene 17beta carboxamide
n [(tert butylcarbamoyl)methyl] n (2 ethyl 6 methylphenyl) 3beta hydroxyandrost 5 ene 17beta carboxamide
n [(tert butylcarbamoyl)methyl] n (2 fluorophenyl) 3beta hydroxyandrost 5 ene 17beta carboxamide
n [(tert butylcarbamoyl)methyl] n (3 trifluorophenyl) 3beta hydroxyandrost 5 ene 17beta carboxamide
n [(tert butylcarbamoyl)methyl] n (3,4 dichlorophenyl) 3beta hydroxyandrost 5 ene 17beta carboxamide
n [(tert butylcarbamoyl)methyl] n (4 fluorophenyl) 3beta hydroxyandrost 5 ene 17beta carboxamide
n [(tert butylcarbamoyl)methyl] n (4 methoxyphenyl) 3beta hydroxyandrost 5 ene 17beta carboxamide
n [(tert butylcarbamoyl)methyl] n (4 methylphenyl) 3beta hydroxyandrost 5 ene 17beta carboxamide
unclassified drug
virus glycoprotein
animal cell
antiviral activity
article
chemical reaction
drug synthesis
fluorescence analysis
Herpes simplex virus 1
nonhuman
priority journal
protein localization
virogenesis
virus inhibition
Antiviral Agents
Diamide
Herpesvirus 1, Human
Humans
Intracellular Space
Sterols
Viral Envelope Proteins
Virus Replication
Human herpesvirus 1
Vesicular stomatitis virus
description The need to develop novel antiviral agents encouraged us to assess the antiviral activity of synthetic sterol analogues with a diamide side chains. Cytotoxicity and antiviral activity of a family of azasterol previously synthesized was evaluated against herpes simplex virus 1 (HSV-1) (KOS and B2006) and vesicular stomatitis virus (VSV). This family of compounds was extended by the synthesis of novel analogs using an Ugi multicomponent reaction and their ability to inhibit viral multiplication was also evaluated. The results show that some of the compounds tested exert an antiviral activity. Besides, the effect of the azasterols on the intracellular localization of viral glycoproteins was examined. Strikingly, alteration on the glycoprotein D (gD) of HSV-1 fluorescence pattern was observed with both the antiherpetic compounds and the inactive azasterols. © 2012 Elsevier Inc.
author Cabrera, Gabriela Myriam
Ramirez, Javier Alberto
Barquero, Andrea Alejandra
author_facet Cabrera, Gabriela Myriam
Ramirez, Javier Alberto
Barquero, Andrea Alejandra
author_sort Cabrera, Gabriela Myriam
title Sterol analogues with diamide side chains interfere with the intracellular localization of viral glycoproteins
title_short Sterol analogues with diamide side chains interfere with the intracellular localization of viral glycoproteins
title_full Sterol analogues with diamide side chains interfere with the intracellular localization of viral glycoproteins
title_fullStr Sterol analogues with diamide side chains interfere with the intracellular localization of viral glycoproteins
title_full_unstemmed Sterol analogues with diamide side chains interfere with the intracellular localization of viral glycoproteins
title_sort sterol analogues with diamide side chains interfere with the intracellular localization of viral glycoproteins
publishDate 2012
url https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0006291X_v427_n1_p107_Davola
http://hdl.handle.net/20.500.12110/paper_0006291X_v427_n1_p107_Davola
work_keys_str_mv AT cabreragabrielamyriam sterolanalogueswithdiamidesidechainsinterferewiththeintracellularlocalizationofviralglycoproteins
AT ramirezjavieralberto sterolanalogueswithdiamidesidechainsinterferewiththeintracellularlocalizationofviralglycoproteins
AT barqueroandreaalejandra sterolanalogueswithdiamidesidechainsinterferewiththeintracellularlocalizationofviralglycoproteins
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