Design of xanthone propionate photolabile protecting group releasing acyclovir for the treatment of ocular herpes simplex virus

Autores
Blake, Jessie A.; Bareiss, Bettina; Jimenez, Liliana Beatriz; Griffith, May; Scaiano, J. C.
Año de publicación
2012
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
We have attached the antiviral drug acyclovir (ACV) to a xanthone photolabile protecting group (or photocage) through the O6 position of acyclovir, a procedure designed for the treatment of ocular herpes simplex virus infections. Acyclovir is photoreleased from the photocage, under physiological conditions, with a quantum yield (ΦACV release) of 0.1-0.3 and an uncaging cross section (Φ·ε) of 450?1350 M cm−1. We demonstrate that this photorelease method outcompetes alternative reaction pathways, such as protonation. Furthermore, complete release of the drug is theoretically possible given a sufficient dose of light . Surprisingly the acyclovir photocage, also showed some antiviral activity towards HSV-1.
Fil: Blake, Jessie A.. University of Ottawa. Faculty of Science; Canadá
Fil: Bareiss, Bettina. University of Ottawa; Canadá
Fil: Jimenez, Liliana Beatriz. University of Ottawa. Faculty of Science; Canadá. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Griffith, May. University of Ottawa; Canadá
Fil: Scaiano, J. C.. University of Ottawa. Faculty of Science; Canadá
Materia
acyclovir
photorelease
xanthone
photocage
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:11336/268780
Acceder
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network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Design of xanthone propionate photolabile protecting group releasing acyclovir for the treatment of ocular herpes simplex virusBlake, Jessie A.Bareiss, BettinaJimenez, Liliana BeatrizGriffith, MayScaiano, J. C.acyclovirphotoreleasexanthonephotocagehttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1We have attached the antiviral drug acyclovir (ACV) to a xanthone photolabile protecting group (or photocage) through the O6 position of acyclovir, a procedure designed for the treatment of ocular herpes simplex virus infections. Acyclovir is photoreleased from the photocage, under physiological conditions, with a quantum yield (ΦACV release) of 0.1-0.3 and an uncaging cross section (Φ·ε) of 450?1350 M cm−1. We demonstrate that this photorelease method outcompetes alternative reaction pathways, such as protonation. Furthermore, complete release of the drug is theoretically possible given a sufficient dose of light . Surprisingly the acyclovir photocage, also showed some antiviral activity towards HSV-1.Fil: Blake, Jessie A.. University of Ottawa. Faculty of Science; CanadáFil: Bareiss, Bettina. University of Ottawa; CanadáFil: Jimenez, Liliana Beatriz. University of Ottawa. Faculty of Science; Canadá. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaFil: Griffith, May. University of Ottawa; CanadáFil: Scaiano, J. C.. University of Ottawa. Faculty of Science; CanadáRoyal Society of Chemistry2012-03info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/268780Blake, Jessie A.; Bareiss, Bettina; Jimenez, Liliana Beatriz; Griffith, May; Scaiano, J. C.; Design of xanthone propionate photolabile protecting group releasing acyclovir for the treatment of ocular herpes simplex virus; Royal Society of Chemistry; Photochemical and Photobiological Sciences; 11; 3; 3-2012; 539-5471474-905XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/content/articlelanding/2012/pp/c2pp05311jinfo:eu-repo/semantics/altIdentifier/doi/10.1039/C2PP05311Jinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-10T13:10:13Zoai:ri.conicet.gov.ar:11336/268780instacron: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:34982025-09-10 13:10:13.873CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Design of xanthone propionate photolabile protecting group releasing acyclovir for the treatment of ocular herpes simplex virus
title Design of xanthone propionate photolabile protecting group releasing acyclovir for the treatment of ocular herpes simplex virus
spellingShingle Design of xanthone propionate photolabile protecting group releasing acyclovir for the treatment of ocular herpes simplex virus
Blake, Jessie A.
acyclovir
photorelease
xanthone
photocage
title_short Design of xanthone propionate photolabile protecting group releasing acyclovir for the treatment of ocular herpes simplex virus
title_full Design of xanthone propionate photolabile protecting group releasing acyclovir for the treatment of ocular herpes simplex virus
title_fullStr Design of xanthone propionate photolabile protecting group releasing acyclovir for the treatment of ocular herpes simplex virus
title_full_unstemmed Design of xanthone propionate photolabile protecting group releasing acyclovir for the treatment of ocular herpes simplex virus
title_sort Design of xanthone propionate photolabile protecting group releasing acyclovir for the treatment of ocular herpes simplex virus
dc.creator.none.fl_str_mv Blake, Jessie A.
Bareiss, Bettina
Jimenez, Liliana Beatriz
Griffith, May
Scaiano, J. C.
author Blake, Jessie A.
author_facet Blake, Jessie A.
Bareiss, Bettina
Jimenez, Liliana Beatriz
Griffith, May
Scaiano, J. C.
author_role author
author2 Bareiss, Bettina
Jimenez, Liliana Beatriz
Griffith, May
Scaiano, J. C.
author2_role author
author
author
author
dc.subject.none.fl_str_mv acyclovir
photorelease
xanthone
photocage
topic acyclovir
photorelease
xanthone
photocage
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv We have attached the antiviral drug acyclovir (ACV) to a xanthone photolabile protecting group (or photocage) through the O6 position of acyclovir, a procedure designed for the treatment of ocular herpes simplex virus infections. Acyclovir is photoreleased from the photocage, under physiological conditions, with a quantum yield (ΦACV release) of 0.1-0.3 and an uncaging cross section (Φ·ε) of 450?1350 M cm−1. We demonstrate that this photorelease method outcompetes alternative reaction pathways, such as protonation. Furthermore, complete release of the drug is theoretically possible given a sufficient dose of light . Surprisingly the acyclovir photocage, also showed some antiviral activity towards HSV-1.
Fil: Blake, Jessie A.. University of Ottawa. Faculty of Science; Canadá
Fil: Bareiss, Bettina. University of Ottawa; Canadá
Fil: Jimenez, Liliana Beatriz. University of Ottawa. Faculty of Science; Canadá. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Griffith, May. University of Ottawa; Canadá
Fil: Scaiano, J. C.. University of Ottawa. Faculty of Science; Canadá
description We have attached the antiviral drug acyclovir (ACV) to a xanthone photolabile protecting group (or photocage) through the O6 position of acyclovir, a procedure designed for the treatment of ocular herpes simplex virus infections. Acyclovir is photoreleased from the photocage, under physiological conditions, with a quantum yield (ΦACV release) of 0.1-0.3 and an uncaging cross section (Φ·ε) of 450?1350 M cm−1. We demonstrate that this photorelease method outcompetes alternative reaction pathways, such as protonation. Furthermore, complete release of the drug is theoretically possible given a sufficient dose of light . Surprisingly the acyclovir photocage, also showed some antiviral activity towards HSV-1.
publishDate 2012
dc.date.none.fl_str_mv 2012-03
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/11336/268780
Blake, Jessie A.; Bareiss, Bettina; Jimenez, Liliana Beatriz; Griffith, May; Scaiano, J. C.; Design of xanthone propionate photolabile protecting group releasing acyclovir for the treatment of ocular herpes simplex virus; Royal Society of Chemistry; Photochemical and Photobiological Sciences; 11; 3; 3-2012; 539-547
1474-905X
CONICET Digital
CONICET
url http://hdl.handle.net/11336/268780
identifier_str_mv Blake, Jessie A.; Bareiss, Bettina; Jimenez, Liliana Beatriz; Griffith, May; Scaiano, J. C.; Design of xanthone propionate photolabile protecting group releasing acyclovir for the treatment of ocular herpes simplex virus; Royal Society of Chemistry; Photochemical and Photobiological Sciences; 11; 3; 3-2012; 539-547
1474-905X
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/content/articlelanding/2012/pp/c2pp05311j
info:eu-repo/semantics/altIdentifier/doi/10.1039/C2PP05311J
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
dc.publisher.none.fl_str_mv Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
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
_version_ 1842980512587579392
score 12.993085

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