In vitro and in vivo antiherpetic activity of three new synthetic brassinosteroid analogues

Brassinosteroids are a novel group of steroids that appear to be ubiquitous in plants and are essential for normal plant growth and development. It has been previously reported that brassinosteroid analogues exert an antiviral activity against herpes simplex virus type 1 (HSV-1) and arenaviruses. In...

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Autores principales:	Michelini, Flavia Mariana, Ramirez, Javier Alberto, Alche, Laura Edith
Publicado:	2004
Materias:	Antiviral activity Brassinosteroids HSV-1 Human conjunctive cell line Murine herpetic stromal keratitis Steroid 3beta bromo 5alpha 22,23 trihydroxystigmastan 6 one 3beta,5alpha,22,23 tetrahydroxystigmastan 6 one 5alpha fluoro 3beta 22,23 trihydroxystigmastan 6 one antivirus agent brassinosteroid steroid unclassified drug animal cell antiviral activity article cell division cell line comparative study cytotoxicity dose response drug synthesis eye injury Herpes simplex virus 1 human human cell immune mediated injury in vitro study in vivo study inflammation male morbidity mouse necrosis nonhuman sample stomatitis vascularization virus infection Animals Anti-Inflammatory Agents Antiviral Agents beta-Galactosidase Cell Line Cell Survival Cercopithecus aethiops Cholestanones Dose-Response Relationship, Drug Herpesvirus 1, Human Humans Inflammation Male Mice Mice, Inbred BALB C Models, Chemical Spectrophotometry Steroids Stigmasterol Time Factors Vero Cells Herpes Human herpesvirus 1 Murinae
Acceso en línea:	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0039128X_v69_n11-12_p713_Michelini http://hdl.handle.net/20.500.12110/paper_0039128X_v69_n11-12_p713_Michelini
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	paper:paper_0039128X_v69_n11-12_p713_Michelini
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spelling	paper:paper_0039128X_v69_n11-12_p713_Michelini2023-06-08T15:03:17Z In vitro and in vivo antiherpetic activity of three new synthetic brassinosteroid analogues Michelini, Flavia Mariana Ramirez, Javier Alberto Alche, Laura Edith Antiviral activity Brassinosteroids HSV-1 Human conjunctive cell line Murine herpetic stromal keratitis Steroid 3beta bromo 5alpha 22,23 trihydroxystigmastan 6 one 3beta,5alpha,22,23 tetrahydroxystigmastan 6 one 5alpha fluoro 3beta 22,23 trihydroxystigmastan 6 one antivirus agent brassinosteroid steroid unclassified drug animal cell antiviral activity article cell division cell line comparative study cytotoxicity dose response drug synthesis eye injury Herpes simplex virus 1 human human cell immune mediated injury in vitro study in vivo study inflammation male morbidity mouse necrosis nonhuman sample stomatitis vascularization virus infection Animals Anti-Inflammatory Agents Antiviral Agents beta-Galactosidase Cell Line Cell Survival Cercopithecus aethiops Cholestanones Dose-Response Relationship, Drug Herpesvirus 1, Human Humans Inflammation Male Mice Mice, Inbred BALB C Models, Chemical Spectrophotometry Steroids Stigmasterol Time Factors Vero Cells Herpes Human herpesvirus 1 Murinae Brassinosteroids are a novel group of steroids that appear to be ubiquitous in plants and are essential for normal plant growth and development. It has been previously reported that brassinosteroid analogues exert an antiviral activity against herpes simplex virus type 1 (HSV-1) and arenaviruses. In the present study, we report the chemical synthesis of compounds (22S,23S)-3β-bromo-5α,22,23-trihydroxystigmastan-6-one (2), (22S,23S)-5α-fluoro-3β-22,23-trihydroxystigmastan-6-one (3), (22S,23S)-3β,5α,22,23-tetrahydroxy-stigmastan-6-one (4) as well as their antiherpetic activity both in a human conjunctive cell line (IOBA-NHC) and in the murine herpetic stromal keratitis (HSK) experimental model. All compounds prevented HSV-1 multiplication in NHC cells in a dose dependent manner when added after infection with no cytotoxicity. Administration of compounds 2, 3, and 4 to the eyes of mice at 1, 2, and 3 days post-infection delayed and reduced the incidence of HSK, consisting mainly of inflammation, vascularization, and necrosis, compared to untreated, infected mice. However, viral titers of eye washes showed no differences among samples from treated and untreated mice. Since the decrease in the percentage of mice with ocular lesions occurred 5 days after treatment had ended, we suggest that brassinosteroids 2, 3, and 4 did not exert a direct antiviral effect in vivo, but rather may play a role in immune-mediated stromal inflammation, which would explain the improvement of the clinical signs of HSK observed. © 2004 Elsevier Inc. All rights reserved. Fil:Michelini, F.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:Alché, L.E. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2004 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0039128X_v69_n11-12_p713_Michelini http://hdl.handle.net/20.500.12110/paper_0039128X_v69_n11-12_p713_Michelini
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 activity Brassinosteroids HSV-1 Human conjunctive cell line Murine herpetic stromal keratitis Steroid 3beta bromo 5alpha 22,23 trihydroxystigmastan 6 one 3beta,5alpha,22,23 tetrahydroxystigmastan 6 one 5alpha fluoro 3beta 22,23 trihydroxystigmastan 6 one antivirus agent brassinosteroid steroid unclassified drug animal cell antiviral activity article cell division cell line comparative study cytotoxicity dose response drug synthesis eye injury Herpes simplex virus 1 human human cell immune mediated injury in vitro study in vivo study inflammation male morbidity mouse necrosis nonhuman sample stomatitis vascularization virus infection Animals Anti-Inflammatory Agents Antiviral Agents beta-Galactosidase Cell Line Cell Survival Cercopithecus aethiops Cholestanones Dose-Response Relationship, Drug Herpesvirus 1, Human Humans Inflammation Male Mice Mice, Inbred BALB C Models, Chemical Spectrophotometry Steroids Stigmasterol Time Factors Vero Cells Herpes Human herpesvirus 1 Murinae
spellingShingle	Antiviral activity Brassinosteroids HSV-1 Human conjunctive cell line Murine herpetic stromal keratitis Steroid 3beta bromo 5alpha 22,23 trihydroxystigmastan 6 one 3beta,5alpha,22,23 tetrahydroxystigmastan 6 one 5alpha fluoro 3beta 22,23 trihydroxystigmastan 6 one antivirus agent brassinosteroid steroid unclassified drug animal cell antiviral activity article cell division cell line comparative study cytotoxicity dose response drug synthesis eye injury Herpes simplex virus 1 human human cell immune mediated injury in vitro study in vivo study inflammation male morbidity mouse necrosis nonhuman sample stomatitis vascularization virus infection Animals Anti-Inflammatory Agents Antiviral Agents beta-Galactosidase Cell Line Cell Survival Cercopithecus aethiops Cholestanones Dose-Response Relationship, Drug Herpesvirus 1, Human Humans Inflammation Male Mice Mice, Inbred BALB C Models, Chemical Spectrophotometry Steroids Stigmasterol Time Factors Vero Cells Herpes Human herpesvirus 1 Murinae Michelini, Flavia Mariana Ramirez, Javier Alberto Alche, Laura Edith In vitro and in vivo antiherpetic activity of three new synthetic brassinosteroid analogues
topic_facet	Antiviral activity Brassinosteroids HSV-1 Human conjunctive cell line Murine herpetic stromal keratitis Steroid 3beta bromo 5alpha 22,23 trihydroxystigmastan 6 one 3beta,5alpha,22,23 tetrahydroxystigmastan 6 one 5alpha fluoro 3beta 22,23 trihydroxystigmastan 6 one antivirus agent brassinosteroid steroid unclassified drug animal cell antiviral activity article cell division cell line comparative study cytotoxicity dose response drug synthesis eye injury Herpes simplex virus 1 human human cell immune mediated injury in vitro study in vivo study inflammation male morbidity mouse necrosis nonhuman sample stomatitis vascularization virus infection Animals Anti-Inflammatory Agents Antiviral Agents beta-Galactosidase Cell Line Cell Survival Cercopithecus aethiops Cholestanones Dose-Response Relationship, Drug Herpesvirus 1, Human Humans Inflammation Male Mice Mice, Inbred BALB C Models, Chemical Spectrophotometry Steroids Stigmasterol Time Factors Vero Cells Herpes Human herpesvirus 1 Murinae
description	Brassinosteroids are a novel group of steroids that appear to be ubiquitous in plants and are essential for normal plant growth and development. It has been previously reported that brassinosteroid analogues exert an antiviral activity against herpes simplex virus type 1 (HSV-1) and arenaviruses. In the present study, we report the chemical synthesis of compounds (22S,23S)-3β-bromo-5α,22,23-trihydroxystigmastan-6-one (2), (22S,23S)-5α-fluoro-3β-22,23-trihydroxystigmastan-6-one (3), (22S,23S)-3β,5α,22,23-tetrahydroxy-stigmastan-6-one (4) as well as their antiherpetic activity both in a human conjunctive cell line (IOBA-NHC) and in the murine herpetic stromal keratitis (HSK) experimental model. All compounds prevented HSV-1 multiplication in NHC cells in a dose dependent manner when added after infection with no cytotoxicity. Administration of compounds 2, 3, and 4 to the eyes of mice at 1, 2, and 3 days post-infection delayed and reduced the incidence of HSK, consisting mainly of inflammation, vascularization, and necrosis, compared to untreated, infected mice. However, viral titers of eye washes showed no differences among samples from treated and untreated mice. Since the decrease in the percentage of mice with ocular lesions occurred 5 days after treatment had ended, we suggest that brassinosteroids 2, 3, and 4 did not exert a direct antiviral effect in vivo, but rather may play a role in immune-mediated stromal inflammation, which would explain the improvement of the clinical signs of HSK observed. © 2004 Elsevier Inc. All rights reserved.
author	Michelini, Flavia Mariana Ramirez, Javier Alberto Alche, Laura Edith
author_facet	Michelini, Flavia Mariana Ramirez, Javier Alberto Alche, Laura Edith
author_sort	Michelini, Flavia Mariana
title	In vitro and in vivo antiherpetic activity of three new synthetic brassinosteroid analogues
title_short	In vitro and in vivo antiherpetic activity of three new synthetic brassinosteroid analogues
title_full	In vitro and in vivo antiherpetic activity of three new synthetic brassinosteroid analogues
title_fullStr	In vitro and in vivo antiherpetic activity of three new synthetic brassinosteroid analogues
title_full_unstemmed	In vitro and in vivo antiherpetic activity of three new synthetic brassinosteroid analogues
title_sort	in vitro and in vivo antiherpetic activity of three new synthetic brassinosteroid analogues
publishDate	2004
url	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0039128X_v69_n11-12_p713_Michelini http://hdl.handle.net/20.500.12110/paper_0039128X_v69_n11-12_p713_Michelini
work_keys_str_mv	AT micheliniflaviamariana invitroandinvivoantiherpeticactivityofthreenewsyntheticbrassinosteroidanalogues AT ramirezjavieralberto invitroandinvivoantiherpeticactivityofthreenewsyntheticbrassinosteroidanalogues AT alchelauraedith invitroandinvivoantiherpeticactivityofthreenewsyntheticbrassinosteroidanalogues
_version_	1768543887671951360

In vitro and in vivo antiherpetic activity of three new synthetic brassinosteroid analogues

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