Polyhydroxylated sulfated steroids derived from 5α-cholestanes as antiviral agents against herpes simplex virus

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Twelve polyhydroxylated sulfated steroids synthesized from a 5α-cholestane skeleton with different substitutions in C-2, C-3 and C-6 were evaluated for cytotoxicity and antiviral activity against herpes simplex virus (HSV) by a virus plaque reduction assay. Four compounds elicited a selective inhibi...

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Autores principales: Pujol, C.A., Sepúlveda, C.S., Richmond, V., Maier, M.S., Damonte, E.B.
Formato: JOUR
Materias:
5α-Cholestanes
Antiviral activity
Herpes simplex virus
Polyhydroxylated sulfated steroids
antivirus agent
cholestane derivative
steroid
animal
cell line
chemical structure
chemistry
drug effects
genital herpes
herpes simplex
Herpes simplex virus 1
Herpes simplex virus 2
human
physiology
structure activity relation
virology
virus entry
Animals
Antiviral Agents
Cell Line
Cholestanes
Herpes Genitalis
Herpes Simplex
Herpesvirus 1, Human
Herpesvirus 2, Human
Humans
Molecular Structure
Steroids
Structure-Activity Relationship
Virus Internalization
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_03048608_v161_n7_p1993_Pujol
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id todo:paper_03048608_v161_n7_p1993_Pujol
record_format dspace
spelling todo:paper_03048608_v161_n7_p1993_Pujol2023-10-03T15:21:02Z Polyhydroxylated sulfated steroids derived from 5α-cholestanes as antiviral agents against herpes simplex virus Pujol, C.A. Sepúlveda, C.S. Richmond, V. Maier, M.S. Damonte, E.B. 5α-Cholestanes Antiviral activity Herpes simplex virus Polyhydroxylated sulfated steroids antivirus agent cholestane derivative steroid animal cell line chemical structure chemistry drug effects genital herpes herpes simplex Herpes simplex virus 1 Herpes simplex virus 2 human physiology structure activity relation virology virus entry Animals Antiviral Agents Cell Line Cholestanes Herpes Genitalis Herpes Simplex Herpesvirus 1, Human Herpesvirus 2, Human Humans Molecular Structure Steroids Structure-Activity Relationship Virus Internalization Twelve polyhydroxylated sulfated steroids synthesized from a 5α-cholestane skeleton with different substitutions in C-2, C-3 and C-6 were evaluated for cytotoxicity and antiviral activity against herpes simplex virus (HSV) by a virus plaque reduction assay. Four compounds elicited a selective inhibitory effect against HSV. The disodium salt of 2β,3α-dihydroxy-6E-hydroximine-5α-cholestane-2,3-disulfate, named compound 7, was the most effective inhibitor of HSV-1, HSV-2 and pseudorabies virus (PrV) strains, including acyclovir-resistant variants, in human and monkey cell lines. Preliminary mechanistic studies demonstrated that compound 7 did not affect the initial steps of virus entry but inhibited a subsequent event in the infection process of HSV. © 2016, Springer-Verlag Wien. Fil:Pujol, C.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Sepúlveda, C.S. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Maier, M.S. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Damonte, E.B. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_03048608_v161_n7_p1993_Pujol
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic 5α-Cholestanes
Antiviral activity
Herpes simplex virus
Polyhydroxylated sulfated steroids
antivirus agent
cholestane derivative
steroid
animal
cell line
chemical structure
chemistry
drug effects
genital herpes
herpes simplex
Herpes simplex virus 1
Herpes simplex virus 2
human
physiology
structure activity relation
virology
virus entry
Animals
Antiviral Agents
Cell Line
Cholestanes
Herpes Genitalis
Herpes Simplex
Herpesvirus 1, Human
Herpesvirus 2, Human
Humans
Molecular Structure
Steroids
Structure-Activity Relationship
Virus Internalization
spellingShingle 5α-Cholestanes
Antiviral activity
Herpes simplex virus
Polyhydroxylated sulfated steroids
antivirus agent
cholestane derivative
steroid
animal
cell line
chemical structure
chemistry
drug effects
genital herpes
herpes simplex
Herpes simplex virus 1
Herpes simplex virus 2
human
physiology
structure activity relation
virology
virus entry
Animals
Antiviral Agents
Cell Line
Cholestanes
Herpes Genitalis
Herpes Simplex
Herpesvirus 1, Human
Herpesvirus 2, Human
Humans
Molecular Structure
Steroids
Structure-Activity Relationship
Virus Internalization
Pujol, C.A.
Sepúlveda, C.S.
Richmond, V.
Maier, M.S.
Damonte, E.B.
Polyhydroxylated sulfated steroids derived from 5α-cholestanes as antiviral agents against herpes simplex virus
topic_facet 5α-Cholestanes
Antiviral activity
Herpes simplex virus
Polyhydroxylated sulfated steroids
antivirus agent
cholestane derivative
steroid
animal
cell line
chemical structure
chemistry
drug effects
genital herpes
herpes simplex
Herpes simplex virus 1
Herpes simplex virus 2
human
physiology
structure activity relation
virology
virus entry
Animals
Antiviral Agents
Cell Line
Cholestanes
Herpes Genitalis
Herpes Simplex
Herpesvirus 1, Human
Herpesvirus 2, Human
Humans
Molecular Structure
Steroids
Structure-Activity Relationship
Virus Internalization
description Twelve polyhydroxylated sulfated steroids synthesized from a 5α-cholestane skeleton with different substitutions in C-2, C-3 and C-6 were evaluated for cytotoxicity and antiviral activity against herpes simplex virus (HSV) by a virus plaque reduction assay. Four compounds elicited a selective inhibitory effect against HSV. The disodium salt of 2β,3α-dihydroxy-6E-hydroximine-5α-cholestane-2,3-disulfate, named compound 7, was the most effective inhibitor of HSV-1, HSV-2 and pseudorabies virus (PrV) strains, including acyclovir-resistant variants, in human and monkey cell lines. Preliminary mechanistic studies demonstrated that compound 7 did not affect the initial steps of virus entry but inhibited a subsequent event in the infection process of HSV. © 2016, Springer-Verlag Wien.
format JOUR
author Pujol, C.A.
Sepúlveda, C.S.
Richmond, V.
Maier, M.S.
Damonte, E.B.
author_facet Pujol, C.A.
Sepúlveda, C.S.
Richmond, V.
Maier, M.S.
Damonte, E.B.
author_sort Pujol, C.A.
title Polyhydroxylated sulfated steroids derived from 5α-cholestanes as antiviral agents against herpes simplex virus
title_short Polyhydroxylated sulfated steroids derived from 5α-cholestanes as antiviral agents against herpes simplex virus
title_full Polyhydroxylated sulfated steroids derived from 5α-cholestanes as antiviral agents against herpes simplex virus
title_fullStr Polyhydroxylated sulfated steroids derived from 5α-cholestanes as antiviral agents against herpes simplex virus
title_full_unstemmed Polyhydroxylated sulfated steroids derived from 5α-cholestanes as antiviral agents against herpes simplex virus
title_sort polyhydroxylated sulfated steroids derived from 5α-cholestanes as antiviral agents against herpes simplex virus
url http://hdl.handle.net/20.500.12110/paper_03048608_v161_n7_p1993_Pujol
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AT richmondv polyhydroxylatedsulfatedsteroidsderivedfrom5acholestanesasantiviralagentsagainstherpessimplexvirus
AT maierms polyhydroxylatedsulfatedsteroidsderivedfrom5acholestanesasantiviralagentsagainstherpessimplexvirus
AT damonteeb polyhydroxylatedsulfatedsteroidsderivedfrom5acholestanesasantiviralagentsagainstherpessimplexvirus
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