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

• 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.

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MEDICINE

MEDICIN

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