Antiherpes virus activities of new 6-19 carbon-bridged steroids and some synthetic precursors

Autores
Petrera, Erina; Joselevich, Maria; Ghini, Alberto Antonio; Burton, Gerardo; Coto, Celia Esther
Año de publicación
2003
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Three synthetic 6,19-carbon bridged steroids: 3β,20β -diacetyloxy-5α-chloro-19a(R)-hydroxy-6,19-methanopregnane, 3β,20β-diacetyloxy-5α-chloro-6,19-methanopregnane, 6,19-methanopregn-4-ene-3,20-dione and four synthetic precursors: 3β,20β-diacetyloxy-19-hydroxypregn-5-ene, 3β,20β -diacetyloxy-pregn-5-en-19-al, 3β,20β -diacetyloxy-19(E)-(methoxymethylidene)-pregn-5-ene and 20β -acetyloxy-3β-hydroxy-19(E)-(methoxymethylidene)-pregn-5-ene were tested against herpes virus replication in cell cultures. Several compounds were cytotoxic for stationary cells. Antiviral studies performed with all compounds against HSV-1 indicated a dose-dependent virus susceptibility with selectivity indexes (SI) values in the range 1.7-183.2. Selected compounds were also tested against HSV-2 and the SI values obtained were in the range of 31-273. Attempts to reveal the step of virus multiplication affected by pregnanes were performed with one compound. HSV-1 virus incubation with the compound did not alter the ability of virus particles to infect cells; moreover, neither virus adsorption nor penetration appeared to be affected. The drug must be present during at least the first 7 h of the virus cycle to inhibit more than 90% of virus production. All these results suggest that these novel molecules interfere with an intracellular step of virus multiplication, thus behaving like true antivirals.
Fil: Petrera, Erina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Biológica. Laboratorio de Virología; Argentina
Fil: Joselevich, Maria. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
Fil: Ghini, Alberto Antonio. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
Fil: Burton, Gerardo. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
Fil: Coto, Celia Esther. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Biológica. Laboratorio de Virología; Argentina
Materia
ANTIVIRAL ACTIVITY
CARBON-BRIDGED STEROIDS
HERPES VIRUS
PREGNANES
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/85635
Acceder
id CONICETDig_db21ef8f2f2a89b58ee233362003ea0c
oai_identifier_str oai:ri.conicet.gov.ar:11336/85635
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Antiherpes virus activities of new 6-19 carbon-bridged steroids and some synthetic precursorsPetrera, ErinaJoselevich, MariaGhini, Alberto AntonioBurton, GerardoCoto, Celia EstherANTIVIRAL ACTIVITYCARBON-BRIDGED STEROIDSHERPES VIRUSPREGNANEShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Three synthetic 6,19-carbon bridged steroids: 3β,20β -diacetyloxy-5α-chloro-19a(R)-hydroxy-6,19-methanopregnane, 3β,20β-diacetyloxy-5α-chloro-6,19-methanopregnane, 6,19-methanopregn-4-ene-3,20-dione and four synthetic precursors: 3β,20β-diacetyloxy-19-hydroxypregn-5-ene, 3β,20β -diacetyloxy-pregn-5-en-19-al, 3β,20β -diacetyloxy-19(E)-(methoxymethylidene)-pregn-5-ene and 20β -acetyloxy-3β-hydroxy-19(E)-(methoxymethylidene)-pregn-5-ene were tested against herpes virus replication in cell cultures. Several compounds were cytotoxic for stationary cells. Antiviral studies performed with all compounds against HSV-1 indicated a dose-dependent virus susceptibility with selectivity indexes (SI) values in the range 1.7-183.2. Selected compounds were also tested against HSV-2 and the SI values obtained were in the range of 31-273. Attempts to reveal the step of virus multiplication affected by pregnanes were performed with one compound. HSV-1 virus incubation with the compound did not alter the ability of virus particles to infect cells; moreover, neither virus adsorption nor penetration appeared to be affected. The drug must be present during at least the first 7 h of the virus cycle to inhibit more than 90% of virus production. All these results suggest that these novel molecules interfere with an intracellular step of virus multiplication, thus behaving like true antivirals.Fil: Petrera, Erina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Biológica. Laboratorio de Virología; ArgentinaFil: Joselevich, Maria. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; ArgentinaFil: Ghini, Alberto Antonio. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; ArgentinaFil: Burton, Gerardo. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; ArgentinaFil: Coto, Celia Esther. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Biológica. Laboratorio de Virología; ArgentinaInternational Medical Press2003-09info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/85635Petrera, Erina; Joselevich, Maria; Ghini, Alberto Antonio; Burton, Gerardo; Coto, Celia Esther; Antiherpes virus activities of new 6-19 carbon-bridged steroids and some synthetic precursors; International Medical Press; Antiviral Chemistry & Chemotherapy; 14; 5; 9-2003; 243-2480956-3202CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://journals.sagepub.com/doi/abs/10.1177/095632020301400503info:eu-repo/semantics/altIdentifier/doi/10.1177/095632020301400503info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T15:03:40Zoai:ri.conicet.gov.ar:11336/85635instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-10-15 15:03:40.628CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Antiherpes virus activities of new 6-19 carbon-bridged steroids and some synthetic precursors
title Antiherpes virus activities of new 6-19 carbon-bridged steroids and some synthetic precursors
spellingShingle Antiherpes virus activities of new 6-19 carbon-bridged steroids and some synthetic precursors
Petrera, Erina
ANTIVIRAL ACTIVITY
CARBON-BRIDGED STEROIDS
HERPES VIRUS
PREGNANES
title_short Antiherpes virus activities of new 6-19 carbon-bridged steroids and some synthetic precursors
title_full Antiherpes virus activities of new 6-19 carbon-bridged steroids and some synthetic precursors
title_fullStr Antiherpes virus activities of new 6-19 carbon-bridged steroids and some synthetic precursors
title_full_unstemmed Antiherpes virus activities of new 6-19 carbon-bridged steroids and some synthetic precursors
title_sort Antiherpes virus activities of new 6-19 carbon-bridged steroids and some synthetic precursors
dc.creator.none.fl_str_mv Petrera, Erina
Joselevich, Maria
Ghini, Alberto Antonio
Burton, Gerardo
Coto, Celia Esther
author Petrera, Erina
author_facet Petrera, Erina
Joselevich, Maria
Ghini, Alberto Antonio
Burton, Gerardo
Coto, Celia Esther
author_role author
author2 Joselevich, Maria
Ghini, Alberto Antonio
Burton, Gerardo
Coto, Celia Esther
author2_role author
author
author
author
dc.subject.none.fl_str_mv ANTIVIRAL ACTIVITY
CARBON-BRIDGED STEROIDS
HERPES VIRUS
PREGNANES
topic ANTIVIRAL ACTIVITY
CARBON-BRIDGED STEROIDS
HERPES VIRUS
PREGNANES
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Three synthetic 6,19-carbon bridged steroids: 3β,20β -diacetyloxy-5α-chloro-19a(R)-hydroxy-6,19-methanopregnane, 3β,20β-diacetyloxy-5α-chloro-6,19-methanopregnane, 6,19-methanopregn-4-ene-3,20-dione and four synthetic precursors: 3β,20β-diacetyloxy-19-hydroxypregn-5-ene, 3β,20β -diacetyloxy-pregn-5-en-19-al, 3β,20β -diacetyloxy-19(E)-(methoxymethylidene)-pregn-5-ene and 20β -acetyloxy-3β-hydroxy-19(E)-(methoxymethylidene)-pregn-5-ene were tested against herpes virus replication in cell cultures. Several compounds were cytotoxic for stationary cells. Antiviral studies performed with all compounds against HSV-1 indicated a dose-dependent virus susceptibility with selectivity indexes (SI) values in the range 1.7-183.2. Selected compounds were also tested against HSV-2 and the SI values obtained were in the range of 31-273. Attempts to reveal the step of virus multiplication affected by pregnanes were performed with one compound. HSV-1 virus incubation with the compound did not alter the ability of virus particles to infect cells; moreover, neither virus adsorption nor penetration appeared to be affected. The drug must be present during at least the first 7 h of the virus cycle to inhibit more than 90% of virus production. All these results suggest that these novel molecules interfere with an intracellular step of virus multiplication, thus behaving like true antivirals.
Fil: Petrera, Erina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Biológica. Laboratorio de Virología; Argentina
Fil: Joselevich, Maria. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
Fil: Ghini, Alberto Antonio. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
Fil: Burton, Gerardo. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
Fil: Coto, Celia Esther. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Biológica. Laboratorio de Virología; Argentina
description Three synthetic 6,19-carbon bridged steroids: 3β,20β -diacetyloxy-5α-chloro-19a(R)-hydroxy-6,19-methanopregnane, 3β,20β-diacetyloxy-5α-chloro-6,19-methanopregnane, 6,19-methanopregn-4-ene-3,20-dione and four synthetic precursors: 3β,20β-diacetyloxy-19-hydroxypregn-5-ene, 3β,20β -diacetyloxy-pregn-5-en-19-al, 3β,20β -diacetyloxy-19(E)-(methoxymethylidene)-pregn-5-ene and 20β -acetyloxy-3β-hydroxy-19(E)-(methoxymethylidene)-pregn-5-ene were tested against herpes virus replication in cell cultures. Several compounds were cytotoxic for stationary cells. Antiviral studies performed with all compounds against HSV-1 indicated a dose-dependent virus susceptibility with selectivity indexes (SI) values in the range 1.7-183.2. Selected compounds were also tested against HSV-2 and the SI values obtained were in the range of 31-273. Attempts to reveal the step of virus multiplication affected by pregnanes were performed with one compound. HSV-1 virus incubation with the compound did not alter the ability of virus particles to infect cells; moreover, neither virus adsorption nor penetration appeared to be affected. The drug must be present during at least the first 7 h of the virus cycle to inhibit more than 90% of virus production. All these results suggest that these novel molecules interfere with an intracellular step of virus multiplication, thus behaving like true antivirals.
publishDate 2003
dc.date.none.fl_str_mv 2003-09
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/85635
Petrera, Erina; Joselevich, Maria; Ghini, Alberto Antonio; Burton, Gerardo; Coto, Celia Esther; Antiherpes virus activities of new 6-19 carbon-bridged steroids and some synthetic precursors; International Medical Press; Antiviral Chemistry & Chemotherapy; 14; 5; 9-2003; 243-248
0956-3202
CONICET Digital
CONICET
url http://hdl.handle.net/11336/85635
identifier_str_mv Petrera, Erina; Joselevich, Maria; Ghini, Alberto Antonio; Burton, Gerardo; Coto, Celia Esther; Antiherpes virus activities of new 6-19 carbon-bridged steroids and some synthetic precursors; International Medical Press; Antiviral Chemistry & Chemotherapy; 14; 5; 9-2003; 243-248
0956-3202
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://journals.sagepub.com/doi/abs/10.1177/095632020301400503
info:eu-repo/semantics/altIdentifier/doi/10.1177/095632020301400503
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv International Medical Press
publisher.none.fl_str_mv International Medical Press
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.22299

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