Study of different substituted cyclic and acyclic benzylpronucleotides of d4T relative to their hydrolytic stability and antiviral activity

Nucleosides Nucleotides Nucleic Acids. 2003 May-Aug;22(5-8):791-5. doi: 10.1081/ncn-120022636.

Abstract

CycloSal-d4TMP and two different bis(benzyl) phosphate triesters of the antivirally active nucleoside analog d4T were studied with regard to their chemical hydrolysis behavior at pH 7.3, in CEM/0 cell extracts, and their anti-HIV activity. In contrast to triesters 2-4, bis-(o-AB)-d4TMP 1 was found to be chemically exquisitely stable. All compounds led to the formation of d4TMP in cell extracts and all triesters achieved the TK-bypass.

MeSH terms

  • Anti-HIV Agents / chemical synthesis*
  • Anti-HIV Agents / chemistry
  • Anti-HIV Agents / pharmacology
  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology
  • Benzyl Compounds
  • Dideoxynucleotides
  • Drug Design
  • Drug Stability
  • Humans
  • Hydrolysis
  • Stavudine / analogs & derivatives*
  • Stavudine / chemical synthesis*
  • Stavudine / chemistry
  • Stavudine / pharmacokinetics
  • Tumor Cells, Cultured

Substances

  • 2',3'-dideoxy-2',3'-didehydrothymidine monophosphate
  • Anti-HIV Agents
  • Antiviral Agents
  • Benzyl Compounds
  • Dideoxynucleotides
  • Stavudine