2',5'-Bis-O-(tert-butyldimethylsilyl)-3'-spiro-5''-(4''-amino-1'',2''- oxathiole-2'',2'-dioxide)pyrimidine (TSAO) nucleoside analogues: highlyselective inhibitors of human immunodeficiency virus type 1 that are targeted at the viral reverse transcriptase

Proc Natl Acad Sci U S A. 1992 May 15;89(10):4392-6. doi: 10.1073/pnas.89.10.4392.

Abstract

A series of pyrimidine nucleoside analogues containing [2',5'-bis-O-(tert-butyldimethylsilyl)-3'-spiro-5''-(4''-amino- 1'',2''-oxathiole-2'',2''-dioxide)]-beta-D-ribofuranose as the pentose were found to inhibit human immunodeficiency virus type 1 [HIV-1(IIIB)] replication at a concentration of 0.06-0.8 microM but were not cytotoxic at a 1000- to 10,000-fold higher concentration. These nucleoside derivatives were also effective against various other HIV-1 strains, including those resistant to 3'-azido-3'-deoxythymidine, but not against HIV-2, simian immunodeficiency virus, Moloney murine sarcoma virus, or other RNA or DNA viruses. They proved to be highly specific inhibitors of the RNA-dependent DNA polymerase function of the HIV-1 reverse transcriptase, showing no marked inhibition of the HIV-1 reverse transcriptase-associated DNA-dependent DNA polymerase activity, HIV-2 reverse transcriptase, DNA polymerase alpha, herpes simplex virus 1 DNA polymerase, or Thermus aquaticus DNA polymerase.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antiviral Agents / pharmacology*
  • Base Sequence
  • Cell Line
  • Cyclic S-Oxides / pharmacology
  • DNA, Viral / genetics*
  • HIV-1 / drug effects*
  • HIV-1 / enzymology*
  • HIV-1 / genetics
  • Heterocyclic Compounds / pharmacology*
  • Humans
  • Macrophages / physiology
  • Molecular Sequence Data
  • Molecular Structure
  • Monocytes / physiology
  • Oligodeoxyribonucleotides
  • Polymerase Chain Reaction
  • Proviruses / drug effects
  • Proviruses / enzymology
  • Proviruses / genetics
  • Pyrimidine Nucleosides / pharmacology*
  • RNA-Directed DNA Polymerase / adverse effects*
  • Silicon / pharmacology
  • Spiro Compounds / pharmacology
  • Structure-Activity Relationship

Substances

  • Antiviral Agents
  • Cyclic S-Oxides
  • DNA, Viral
  • Heterocyclic Compounds
  • Oligodeoxyribonucleotides
  • Pyrimidine Nucleosides
  • Spiro Compounds
  • RNA-Directed DNA Polymerase
  • Silicon