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

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 (Φ(ACV 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.

• Authors: Jessie A Blake, Bettina Bareiss, Liliana Jimenez, May Griffith, J C Scaiano
• Journal: Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology (Photochem Photobiol Sci) Vol. 11 Issue 3 Pg. 539-47 (Mar 2012) ISSN: 1474-9092 [Electronic] England
• PMID: 22222893 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Antiviral Agents
• Propionates
• Xanthones
• xanthone
• Acyclovir

Topics

• Acyclovir (chemistry, therapeutic use)
• Antiviral Agents (chemistry, therapeutic use)
• Keratitis, Herpetic (drug therapy)
• Molecular Structure
• Photolysis
• Propionates (chemical synthesis, chemistry)
• Ultraviolet Rays
• Xanthones (chemical synthesis, chemistry)