The Pronucleotide Approach. I. Synthesis, Anti-HIV Activity and Preliminary Stability Studies of Mononucleoside S,S′-Bis(O-acyl-2-oxyethyl) Phosphorodithiolates

N. Schlienger Laboratoire de Chimie Bioorganique, UMR CNRS-USTL 5625, Université Montpellier II, Case courrier 008, Place E. Bataillon, 34095, Montpellier, Cedex 5, France

C. Périgaud Laboratoire de Chimie Bioorganique, UMR CNRS-USTL 5625, Université Montpellier II, Case courrier 008, Place E. Bataillon, 34095, Montpellier, Cedex 5, France

G. Gosselin Laboratoire de Chimie Bioorganique, UMR CNRS-USTL 5625, Université Montpellier II, Case courrier 008, Place E. Bataillon, 34095, Montpellier, Cedex 5, France

I. Lefebvre Laboratoire de Chimie Bioorganique, UMR CNRS-USTL 5625, Université Montpellier II, Case courrier 008, Place E. Bataillon, 34095, Montpellier, Cedex 5, France

A. Pompon Laboratoire de Chimie Bioorganique, UMR CNRS-USTL 5625, Université Montpellier II, Case courrier 008, Place E. Bataillon, 34095, Montpellier, Cedex 5, France

A.-M. Aubertin Laboratoire de Chimie Bioorganique, UMR CNRS-USTL 5625, Université Montpellier II, Case courrier 008, Place E. Bataillon, 34095, Montpellier, Cedex 5, France

A. Kirn Université Louis Pasteur, Institut de Virologie, INSERM U 74, 67000, Strasbourg, France

J.-L. Imbach Laboratoire de Chimie Bioorganique, UMR CNRS-USTL 5625, Université Montpellier II, Case courrier 008, Place E. Bataillon, 34095, Montpellier, Cedex 5, France

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Abstract

The synthesis, in vitro anti-HIV activity, and preliminary stability studies of several mononucleoside phosphorodithiolate derivatives incorporating a new kind of bio-labile phosphate-protection, namely 0-pivaloyl-2-oxyethyl, are reported. Our preliminary results strongly support the hypothesis that such pronucleotides exert their biological effects via intracellular delivery of the corresponding 5′-mononucleotide.

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The Pronucleotide Approach. I. Synthesis, Anti-HIV Activity and Preliminary Stability Studies of Mononucleoside S,S′-Bis(O-acyl-2-oxyethyl) Phosphorodithiolates

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The Pronucleotide Approach. I. Synthesis, Anti-HIV Activity and Preliminary Stability Studies of Mononucleoside S,S′-Bis(O-acyl-2-oxyethyl) Phosphorodithiolates

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