Alpha-carboxynucleoside phosphonates: direct-acting inhibitors of viral DNA polymerases

Future Med Chem. 2019 Jan;11(2):137-154. doi: 10.4155/fmc-2018-0324. Epub 2019 Jan 16.

Abstract

Acyclic nucleoside phosphonates represent a well-defined class of clinically used nucleoside analogs. All acyclic nucleoside phosphonates need intracellular phosphorylation before they can bind viral DNA polymerases. Recently, a novel class of alpha-carboxynucleoside phosphonates have been designed to mimic the natural 2'-deoxynucleotide 5'-triphosphate substrates of DNA polymerases. They contain a carboxyl group in the phosphonate moiety linked to the nucleobase through a cyclic or acyclic bridge. Alpha-carboxynucleoside phosphonates act as viral DNA polymerase inhibitors without any prior requirement of metabolic conversion. Selective inhibitory activity against retroviral reverse transcriptase and herpesvirus DNA polymerases have been demonstrated. These compounds have a unique mechanism of inhibition of viral DNA polymerases, and provide possibilities for further modifications to optimize and fine tune their antiviral DNA polymerase spectrum.

Keywords: HIV; acyclic nucleoside phosphonate (ANP); chemotherapeutics; herpesviruses; nucleoside-analog inhibitor; reverse transcriptase (RT); viral DNA polymerase; α-carboxynucleoside phosphonate (α-CNP).

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Review

MeSH terms

  • Animals
  • Antiviral Agents / chemistry*
  • Antiviral Agents / pharmacology*
  • DNA-Directed DNA Polymerase
  • Drug Discovery
  • Exodeoxyribonucleases / antagonists & inhibitors
  • Herpes Simplex / drug therapy
  • Humans
  • Models, Molecular
  • Nucleic Acid Synthesis Inhibitors / chemistry*
  • Nucleic Acid Synthesis Inhibitors / pharmacology*
  • Nucleosides / analogs & derivatives*
  • Nucleosides / pharmacology*
  • Organophosphonates / chemistry*
  • Organophosphonates / pharmacology*
  • Reverse Transcriptase Inhibitors / chemistry
  • Reverse Transcriptase Inhibitors / pharmacology
  • Viral Proteins / antagonists & inhibitors
  • Virus Diseases / drug therapy
  • Viruses / drug effects
  • Viruses / enzymology

Substances

  • Antiviral Agents
  • Nucleic Acid Synthesis Inhibitors
  • Nucleosides
  • Organophosphonates
  • Reverse Transcriptase Inhibitors
  • Viral Proteins
  • DNA-Directed DNA Polymerase
  • Exodeoxyribonucleases
  • DNA polymerase, Simplexvirus