Novel nonnucleoside inhibitor of hepatitis C virus RNA-dependent RNA polymerase

Antimicrob Agents Chemother. 2004 Dec;48(12):4813-21. doi: 10.1128/AAC.48.12.4813-4821.2004.

Abstract

A novel nonnucleoside inhibitor of hepatitis C virus (HCV) RNA-dependent RNA polymerase (RdRp), [(1R)-5-cyano-8-methyl-1-propyl-1,3,4,9-tetrahydropyano[3,4-b]indol-1-yl] acetic acid (HCV-371), was discovered through high-throughput screening followed by chemical optimization. HCV-371 displayed broad inhibitory activities against the NS5B RdRp enzyme, with 50% inhibitory concentrations ranging from 0.3 to 1.8 microM for 90% of the isolates derived from HCV genotypes 1a, 1b, and 3a. HCV-371 showed no inhibitory activity against a panel of human polymerases, including mitochondrial DNA polymerase gamma, and other unrelated viral polymerases, demonstrating its specificity for the HCV polymerase. A single administration of HCV-371 to cells containing the HCV subgenomic replicon for 3 days resulted in a dose-dependent reduction of the steady-state levels of viral RNA and protein. Multiple treatments with HCV-371 for 16 days led to a >3-log10 reduction in the HCV RNA level. In comparison, multiple treatments with a similar inhibitory dose of alpha interferon resulted in a 2-log10 reduction of the viral RNA level. In addition, treatment of cells with a combination of HCV-371 and pegylated alpha interferon resulted in an additive antiviral activity. Within the effective antiviral concentrations of HCV-371, there was no effect on cell viability and metabolism. The intracellular antiviral specificity of HCV-371 was demonstrated by its lack of activity in cells infected with several DNA or RNA viruses. Fluorescence binding studies show that HCV-371 binds the NS5B with an apparent dissociation constant of 150 nM, leading to high selectivity and lack of cytotoxicity in the antiviral assays.

Publication types

  • Comparative Study

MeSH terms

  • Animals
  • Antiviral Agents / pharmacology*
  • Cells, Cultured
  • Chlorocebus aethiops
  • Cytopathogenic Effect, Viral
  • DNA-Directed DNA Polymerase / metabolism
  • Drug Evaluation, Preclinical
  • Enzyme Inhibitors / pharmacology*
  • Escherichia coli / genetics
  • HIV Reverse Transcriptase / analysis
  • HIV Reverse Transcriptase / metabolism
  • Hepacivirus / drug effects*
  • Hepacivirus / enzymology*
  • Humans
  • Indoles / pharmacology*
  • Interferon-alpha / pharmacology
  • Pyrans / pharmacology*
  • RNA-Dependent RNA Polymerase / antagonists & inhibitors*
  • Replicon / drug effects
  • Spectrometry, Fluorescence
  • Substrate Specificity
  • Vero Cells
  • Viral Nonstructural Proteins / antagonists & inhibitors
  • Viral Nonstructural Proteins / genetics
  • Viral Nonstructural Proteins / isolation & purification
  • Viral Nonstructural Proteins / metabolism

Substances

  • (5-cyano-8-methyl-1-propyl-1,3,4,9-tetrahydropyrano(3,4-b)indol-1-yl)acetic acid
  • Antiviral Agents
  • Enzyme Inhibitors
  • Indoles
  • Interferon-alpha
  • NS3 protein, hepatitis C virus
  • Pyrans
  • Viral Nonstructural Proteins
  • NS-5 protein, hepatitis C virus
  • RNA-Dependent RNA Polymerase
  • HIV Reverse Transcriptase
  • DNA-Directed DNA Polymerase