Design of xanthone propionate photolabile protecting group releasing acyclovir for the treatment of ocular herpes simplex virus
2012 (English)In: Photochemical and Photobiological Sciences, ISSN 1474-905X, E-ISSN 1474-9092, Vol. 11, no 3, 539-547 p.Article in journal (Refereed) Published
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 (Phi(ACV release)) of 0.1-0.3 and an uncaging cross section (Phi.epsilon) 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.
Place, publisher, year, edition, pages
Royal Society of Chemistry , 2012. Vol. 11, no 3, 539-547 p.
Medical and Health Sciences
IdentifiersURN: urn:nbn:se:liu:diva-76028DOI: 10.1039/c2pp05311jISI: 000300991600014OAI: oai:DiVA.org:liu-76028DiVA: diva2:512812
Funding Agencies|Natural Sciences and Engineering Research Council (NSERC)||Canadian Institutes of Health Research (CIHR Regenerative Medicine Team)|92100337436-07|Canadian Foundation for Innovation||province of Ontario||2012-03-292012-03-232013-12-17