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Issue 3, 2012
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Design of xanthone propionate photolabile protecting group releasing acyclovir for the treatment of ocular herpes simplex virus

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Abstract

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.

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

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Publication details

The article was received on 25 Sep 2011, accepted on 23 Nov 2011 and first published on 06 Jan 2012


Article type: Paper
DOI: 10.1039/C2PP05311J
Citation: Photochem. Photobiol. Sci., 2012,11, 539-547
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    Design of xanthone propionate photolabile protecting group releasing acyclovir for the treatment of ocular herpes simplex virus

    J. A. Blake, B. Bareiss, L. Jimenez, M. Griffith and J. C. Scaiano, Photochem. Photobiol. Sci., 2012, 11, 539
    DOI: 10.1039/C2PP05311J

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