4'C-ethynyl-thymidine acts as a chain terminator during DNA-synthesis catalyzed by HIV-1 reverse transcriptase

Bioorg Med Chem Lett. 2005 Feb 15;15(4):869-71. doi: 10.1016/j.bmcl.2004.12.072.

Abstract

Recently, 4'C-ethynyl nucleoside analogues have been identified as highly potent agents against HIV-1, including several multidrug-resistant strains. In contrast to most known nucleoside inhibitors 4'C-ethynyl nucleoside analogues possess a 3'-hydroxyl function. Here we show that the 5'O-triphosphate of 4'C-ethynyl thymidine gets readily incorporated into a nascent DNA strand by HIV-1 reverse transcriptase and significantly inhibits further post-incorporation chain extension by the enzyme.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis / drug effects
  • HIV Reverse Transcriptase / metabolism*
  • Kinetics
  • Protein Biosynthesis / drug effects*
  • Reverse Transcriptase Inhibitors / chemistry
  • Reverse Transcriptase Inhibitors / pharmacology*
  • Structure-Activity Relationship
  • Thymidine / analogs & derivatives*
  • Thymidine / metabolism
  • Thymidine / pharmacology*

Substances

  • 4'C-ethynyl-thymidine
  • Reverse Transcriptase Inhibitors
  • HIV Reverse Transcriptase
  • Thymidine