Are 5'-O-carbamate-2',3'-dideoxythiacytidine new anti-HIV and anti-HBV nucleoside drugs or prodrugs?

  • Bioorg Med Chem Lett. 2003 Aug 4;13(15):2459-63. doi: 10.1016/s0960-894x(03)00496-7.
Carole Anastasi  1 ,  Patrick Vlieghe ,  Olivier Hantz ,  Olivier Schorr ,  Christophe Pannecouque ,  Myriam Witvrouw ,  Erik De Clercq ,  Pascal Clayette ,  Nathalie Dereuddre-Bosquet ,  Dominique Dormont ,  Françoise Gondois-Rey ,  Ivan Hirsch ,  Jean-Louis Kraus
Affiliations
  • 1. Laboratoire de Chimie Biomoléculaire, INSERM U-382, IBDM, Université Méditerranée, Parc Scientifique de Luminy, 163 avenue de Luminy, case 901, 13288 Marseille Cedex 9, France.
PMID: 12852943 DOI: 10.1016/s0960-894x(03)00496-7
Abstract

In contrast to 5'-O-carbonate 3TC derivatives (23, 24), which are clearly 3TC prodrugs, the corresponding 3TC carbamates (15-21 and 25), found to be very stable compounds with respect to enzymatic hydrolysis (cellular lysates and culture cell media) and still active on both HIV-1 and HBV infected cells, may not be 3TC prodrugs. The Antiviral properties as well as the mechanism of action of 3TC analogues have been studied and evaluated.