Enantiomeric 2',3'-dideoxycytidine derivatives are potent human immunodeficiency virus inhibitors in cell cultures

G Gosselin; C Mathé; M C Bergogne; A M Aubertin; A Kirn; R F Schinazi; J P Sommadossi; J L Imbach

Enantiomeric 2',3'-dideoxycytidine derivatives are potent human immunodeficiency virus inhibitors in cell cultures

C R Acad Sci III. 1994 Jan;317(1):85-9.

Authors

G Gosselin¹, C Mathé, M C Bergogne, A M Aubertin, A Kirn, R F Schinazi, J P Sommadossi, J L Imbach

Affiliation

¹ Laboratoire de Chimie Bioorganique, URA CNRS 488, Université de Montpellier-II, Sciences et Techniques du Languedoc, Montpellier, France.

PMID: 7987696

Abstract

2',3'-dideoxy-beta-L-cytidine (beta-L-DDC) and its 5-fluoro derivative (beta-L-5-F-DDC) have been stereospecifically synthesized by a multi-step reaction sequence from L-xylose and their anti-HIV properties examined. Among these two L-enantiomers, the hitherto unknown beta-L-5-F-DDC emerged as a potent anti-HIV-1 and HIV-2 compound in different cell culture systems, with selectivity indices similar or superior to those of the currently licensed drug DDC which has the natural beta-D configuration.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cells, Cultured
HIV / drug effects*
HIV / growth & development
HIV-1 / drug effects
HIV-2 / drug effects
Molecular Conformation
Stereoisomerism
Zalcitabine / analogs & derivatives*
Zalcitabine / chemical synthesis
Zalcitabine / pharmacology

Substances

2',3'-dideoxy-beta-5-fluorocytidine
Zalcitabine