PMID: 11900349Mar 20, 2002Paper

Antiviral activity of cyclosaligenyl prodrugs of acyclovir, carbovir and abacavir

Antiviral Chemistry & Chemotherapy
J BalzariniC Meier

Abstract

The cyclosaligenyl (cycloSal) derivatives of the monophosphates of three acyclic or carbocyclic guanosine analogues, for example, acyclovir (ACV), carbovir (CBV) and abacavir (ABC), were investigated for their activity against retrovirus (HIV, Moloney sarcoma virus) and herpes simplex virus (HSV) activity in cell culture. The extent of the antiviral potency of the prodrugs depended on the nature of the nucleoside, the substituent on the cycloSal moiety and the virus investigated. Most notably, and unlike the parent compound ACV, cycloSal-ACV monophosphate (MP) prodrugs retained pronounced activity against ACV-resistant (thymidine kinase-deficient) HSV-1 and also gained anti-HIV activity. While the cycloSal-CBVMP prodrugs did not show enhanced activity compared with the parent compound CBV, the cycloSal-ABCMP prodrugs afforded markedly increased potency against both HSV and HIV. Our data indicate that the cycloSal prodrug approach can be useful to deliver directly the MP derivatives of nucleoside analogues into the intact, virus-infected cells, thus improving and extending the antiviral potency and spectrum of the drugs against retro- and herpesvirus strains.

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Citations

Mar 6, 2015·Clinical Infectious Diseases : an Official Publication of the Infectious Diseases Society of America·Christophe VanpouilleLeonid Margolis
Dec 13, 2006·Nucleosides, Nucleotides & Nucleic Acids·Mariola Koszytkowska-StawińskaErik De Clercq
Mar 27, 2004·Nucleosides, Nucleotides & Nucleic Acids·Chris MeierJan Balzarini
Feb 21, 2008·Antimicrobial Agents and Chemotherapy·Parmjeet RandhawaMatthews Bradley
Jan 16, 2021·Journal of Pharmaceutical Sciences·Maria Silvia Gurgel AssisAndré Luís Morais Ruela
May 20, 2021·Chemistry of Heterocyclic Compounds·Vladimir E Kataev, Bulat F Garifullin
May 26, 2004·Bioorganic & Medicinal Chemistry·T K VenkatachalamF M Uckun
Mar 6, 2007·Journal of Medicinal Chemistry·Nicolas GischChris Meier

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