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Design of xanthone propionate photolabile protecting group releasing acyclovir for the treatment of ocular herpes simplex virus
University of Ottawa.
University of Ottawa.
University of Ottawa.
Linköping University, Department of Clinical and Experimental Medicine, Ophthalmology. Linköping University, Faculty of Health Sciences.ORCID iD: 0000-0003-1222-6720
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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
Abstract [en]

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.
National Category
Medical and Health Sciences
URN: urn:nbn:se:liu:diva-76028DOI: 10.1039/c2pp05311jISI: 000300991600014OAI: 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||Available from: 2012-03-29 Created: 2012-03-23 Last updated: 2013-12-17

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Griffith, May
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