Novel AR-12 derivatives, P12-23 and P12-34, inhibit flavivirus replication by blocking host de novo pyrimidine biosynthesis

Emerg Microbes Infect. 2018 Nov 21;7(1):187. doi: 10.1038/s41426-018-0191-1.

Abstract

The genus Flavivirus contains many important pathogens, including dengue virus (DENV), Zika virus (ZIKV), and Japanese encephalitis virus (JEV). AR-12 is a celecoxib-derived anticancer agent that possesses antiviral activity against a broad range of viruses. We pharmacologically exploited this unique activity to develop additional antiviral agents, resulting in the production of the AR-12 derivatives P12-23 and P12-34. At nanomolar concentrations, these compounds were effective in suppressing DENV, ZIKV and JEV replication, exhibiting 10-fold improvements in the efficacy and selectivity indices as compared to AR-12. Regarding the mode of antiviral action, P12-23 and P12-34 inhibited viral RNA replication but had no effect on viral binding, entry or translation. Moreover, these AR-12 derivatives co-localized with mitochondrial markers, and their antiviral activity was lost in mitochondria-depleted cells. Interestingly, exogenous uridine or orotate, the latter being a metabolite of the mitochondrial enzyme dihydroorotate dehydrogenase (DHODH), abolished the antiviral activity of AR-12 and its derivatives. As DHODH is a key enzyme in the de novo pyrimidine biosynthesis pathway, these AR-12 derivatives may act by targeting pyrimidine biosynthesis in host cells to inhibit viral replication. Importantly, treatment with P12-34 significantly improved the survival of mice that were subcutaneously challenged with DENV. Thus, P12-34 may warrant further evaluation as a therapeutic to control flaviviral outbreaks.

MeSH terms

  • A549 Cells
  • Animals
  • Antiviral Agents / pharmacology
  • Biosynthetic Pathways
  • Cell Line
  • Dengue Virus / drug effects
  • Dihydroorotate Dehydrogenase
  • Flavivirus / drug effects
  • Flavivirus / physiology*
  • Host-Pathogen Interactions
  • Humans
  • Mice
  • Oxidoreductases Acting on CH-CH Group Donors / metabolism
  • Pyrazoles / chemistry*
  • Pyrazoles / pharmacology*
  • Pyrimidines / biosynthesis*
  • Sulfonamides / chemistry*
  • Sulfonamides / pharmacology*
  • Uridine / pharmacology
  • Virus Replication / drug effects*
  • Zika Virus / drug effects

Substances

  • Antiviral Agents
  • Dihydroorotate Dehydrogenase
  • OSU 03012
  • Pyrazoles
  • Pyrimidines
  • Sulfonamides
  • Oxidoreductases Acting on CH-CH Group Donors
  • pyrimidine
  • Uridine