Activities of the four optical isomers of 2',3'-dideoxy-3'-thiacytidine (BCH-189) against human immunodeficiency virus type 1 in human lymphocytes

Antimicrob Agents Chemother. 1992 Mar;36(3):672-6. doi: 10.1128/AAC.36.3.672.

Abstract

Four different isomers of 2',3'-dideoxy-3'-thiacytidine [beta-DL-(+-)-BCH-189] were evaluated in primary human lymphocytes infected with human immunodeficiency virus type 1. The beta-L-(-) isomer was the most potent enantiomer, with a median effective concentration of 1.8 nM and no discernible cytotoxicity up to 100 microM. The relative order of potencies for the isomers was beta-L-(-) greater than beta-DL-(+-) racemic greater than beta-D-(+) greater than alpha-L-(+) greater than alpha-D-(-). The beta-L-(-) enantiomer was as potent as 3'-azido-3'-deoxythymidine.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Antiviral Agents / pharmacology*
  • HIV-1 / drug effects*
  • Humans
  • Lamivudine
  • Lymphocytes / drug effects*
  • Lymphocytes / microbiology
  • Microbial Sensitivity Tests
  • Stereoisomerism
  • Structure-Activity Relationship
  • Zalcitabine / analogs & derivatives*
  • Zalcitabine / pharmacology
  • Zidovudine / pharmacology

Substances

  • Antiviral Agents
  • Lamivudine
  • Zidovudine
  • Zalcitabine