9-[(2RS)-3-fluoro-2-phosphonylmethoxypropyl] derivatives of purines: a class of highly selective antiretroviral agents in vitro and in vivo

Proc Natl Acad Sci U S A. 1991 Jun 1;88(11):4961-5. doi: 10.1073/pnas.88.11.4961.

Abstract

A new class of compounds, 9-[(2RS)-3-fluoro-2-phosphonylmethoxypropyl] [(RS)-FPMP] derivatives of purines, is described that has selective activity against a broad spectrum of retroviruses [including human immunodeficiency virus type 1 (HIV-1) and type 2 (HIV-2)] but not other RNA or DNA viruses. This activity spectrum is completely different from that of the parental compounds, 9-[(2S)-3-hydroxy-2-phosphonylmethoxypropyl] [(S)-HPMP] derivatives of purines, which are active against a broad range of DNA viruses. The racemic (RS)-FPMP derivatives of adenine and 2,6-diaminopurine, termed (RS)-FPMPA and (RS)-FPMPDAP, respectively, are markedly more selective as in vitro antiretroviral agents than their 9-(2-phosphonylmethoxyethyl) (PME) counterparts, PMEA and PMEDAP. Also, (RS)-FPMPA and (RS)-FPMPDAP have a substantially higher therapeutic index in mice in inhibiting Moloney murine sarcoma virus-induced tumor formation and associated death and are markedly less inhibitory to human bone marrow cells than PMEA and PMEDAP. The diphosphate derivative of (RS)-FPMPA [(RS)-FPMPApp] is a potent and selective inhibitor of HIV-1 reverse transcriptase but not of HSV-1 DNA polymerase or DNA polymerase alpha. (RS)-FPMPApp, akin to PMEA diphosphate (PMEApp), acts as a DNA chain terminator. The DNA chain-terminating properties of PMEApp and (RS)-FPMPApp seem to be a prerequisite for acyclic nucleoside phosphonates to exhibit antiretrovirus (i.e., anti-HIV) activity.

Publication types

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

MeSH terms

  • Adenine / analogs & derivatives*
  • Adenine / chemical synthesis
  • Adenine / pharmacology
  • Animals
  • Antiviral Agents / pharmacology*
  • Avian Myeloblastosis Virus / enzymology
  • Cell Line
  • Cell Transformation, Neoplastic / drug effects
  • DNA Replication / drug effects
  • HIV / enzymology
  • HIV Reverse Transcriptase
  • HIV-1 / drug effects
  • HIV-2 / drug effects
  • Humans
  • Mice
  • Organophosphonates*
  • Organophosphorus Compounds / chemical synthesis
  • Organophosphorus Compounds / pharmacology*
  • Purines / chemical synthesis
  • Purines / pharmacology*
  • Retroviridae / drug effects*
  • Reverse Transcriptase Inhibitors*
  • Simian Immunodeficiency Virus / drug effects
  • Structure-Activity Relationship

Substances

  • Antiviral Agents
  • Organophosphonates
  • Organophosphorus Compounds
  • Purines
  • Reverse Transcriptase Inhibitors
  • 9-(3-fluoro-2-phosphonylmethoxypropyl)adenine
  • HIV Reverse Transcriptase
  • Adenine