Designing a pronucleotide stratagem: lessons from amino acid phosphoramidates of anticancer and antiviral pyrimidines.

Dan P Drontle, Carston R Wagner

Journal: Mini reviews in medicinal chemistry 2004;4(4):409-19

PMID: 15134543

Abstract

Phosphoramidate pronucleotides have proven to be an effective strategy for the intracellular delivery of nucleoside 5'-monophosphates. This review will summarize our efforts to understand the in vitro and in vivo behavior of phosphoramidate monoesters of 3'-azido-3'-deoxythymidine (AZT), 3'-fluoro-3'-deoxythymidine (FLT) and 5-fluoro-2'-deoxyuridine (FUdR). Insights drawn from these studies have proved valuable for the future design of phosphoramidate-based pronucleotides.

Address: Department of Medicinal Chemistry, College of Pharmacy, University of Minnesota, Minneapolis, Minnesota 55455, USA.

DOI: 10.2174/1389557043403945

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MeSH Terms: Amides, Amino Acids, Antineoplastic Agents, Antiviral Agents, Dideoxynucleosides, Drug Design, Fluorodeoxyuridylate, Humans, Molecular Structure, Nucleotides, Phosphoric Acids, Prodrugs, Pyrimidines, Time Factors, Zidovudine