Mechanism and spectrum of inhibition of a 4'-cyano modified nucleotide analog against diverse RNA polymerases of prototypic respiratory RNA viruses

J Biol Chem. 2024 Aug;300(8):107514. doi: 10.1016/j.jbc.2024.107514. Epub 2024 Jun 28.

Abstract

The development of safe and effective broad-spectrum antivirals that target the replication machinery of respiratory viruses is of high priority in pandemic preparedness programs. Here, we studied the mechanism of action of a newly discovered nucleotide analog against diverse RNA-dependent RNA polymerases (RdRps) of prototypic respiratory viruses. GS-646939 is the active 5'-triphosphate metabolite of a 4'-cyano modified C-adenosine analog phosphoramidate prodrug GS-7682. Enzyme kinetics show that the RdRps of human rhinovirus type 16 (HRV-16) and enterovirus 71 incorporate GS-646939 with unprecedented selectivity; GS-646939 is incorporated 20-50-fold more efficiently than its natural ATP counterpart. The RdRp complex of respiratory syncytial virus and human metapneumovirus incorporate GS-646939 and ATP with similar efficiency. In contrast, influenza B RdRp shows a clear preference for ATP and human mitochondrial RNA polymerase does not show significant incorporation of GS-646939. Once incorporated into the nascent RNA strand, GS-646939 acts as a chain terminator although higher NTP concentrations can partially overcome inhibition for some polymerases. Modeling and biochemical data suggest that the 4'-modification inhibits RdRp translocation. Comparative studies with GS-443902, the active triphosphate form of the 1'-cyano modified prodrugs remdesivir and obeldesivir, reveal not only different mechanisms of inhibition, but also differences in the spectrum of inhibition of viral polymerases. In conclusion, 1'-cyano and 4'-cyano modifications of nucleotide analogs provide complementary strategies to target the polymerase of several families of respiratory RNA viruses.

Keywords: COVID-19; RNA virus; RNA-dependent RNA polymerase; SARS-CoV-2; antiviral; coronavirus; enterovirus; influenza virus; nucleotide analog; pandemic preparedness; prototypic pathogens; remdesivir; respiratory syncytial virus; respiratory viruses; rhinovirus.

MeSH terms

  • Antiviral Agents* / chemistry
  • Antiviral Agents* / pharmacology
  • Humans
  • Metapneumovirus / drug effects
  • Nucleotides / chemistry
  • Nucleotides / metabolism
  • Nucleotides / pharmacology
  • RNA Viruses / drug effects
  • RNA Viruses / enzymology
  • RNA-Dependent RNA Polymerase* / antagonists & inhibitors
  • RNA-Dependent RNA Polymerase* / chemistry
  • RNA-Dependent RNA Polymerase* / metabolism

Substances

  • Antiviral Agents
  • RNA-Dependent RNA Polymerase
  • Nucleotides