Quinoxaline-based inhibitors of Ebola and Marburg VP40 egress

Bioorg Med Chem Lett. 2016 Aug 1;26(15):3429-35. doi: 10.1016/j.bmcl.2016.06.053. Epub 2016 Jun 23.

Abstract

We prepared a series of quinoxalin-2-mercapto-acetyl-urea analogs and evaluated them for their ability to inhibit viral egress in our Marburg and Ebola VP40 VLP budding assays in HEK293T cells. We also evaluated selected compounds in our bimolecular complementation assay (BiMC) to detect and visualize a Marburg mVP40-Nedd4 interaction in live mammalian cells. Antiviral activity was assessed for selected compounds using a live recombinant vesicular stomatitis virus (VSV) (M40 virus) that expresses the EBOV VP40 PPxY L-domain. Finally selected compounds were evaluated in several ADME assays to have an early assessment of their drug properties. Our compounds had low nM potency in these assays (e.g., compounds 21, 24, 26, 39), and had good human liver microsome stability, as well as little or no inhibition of P450 3A4.

Keywords: Antiviral therapeutic; Budding; Ebola virus; L-domain; Marburg virus; Nedd4; PPxY; RNA viruses; Virus egress.

MeSH terms

  • Animals
  • Antiviral Agents / chemical synthesis
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology*
  • Cytochrome P-450 CYP3A / metabolism
  • Cytochrome P-450 CYP3A Inhibitors / chemical synthesis
  • Cytochrome P-450 CYP3A Inhibitors / chemistry
  • Cytochrome P-450 CYP3A Inhibitors / pharmacology*
  • Dose-Response Relationship, Drug
  • Ebolavirus / chemistry
  • HEK293 Cells
  • Humans
  • Marburgvirus / chemistry
  • Mice
  • Microbial Sensitivity Tests
  • Microsomes, Liver / chemistry
  • Microsomes, Liver / metabolism
  • Molecular Structure
  • Quinoxalines / chemical synthesis
  • Quinoxalines / chemistry
  • Quinoxalines / pharmacology*
  • Structure-Activity Relationship
  • Vesicular stomatitis Indiana virus / drug effects*
  • Viral Matrix Proteins / antagonists & inhibitors*

Substances

  • Antiviral Agents
  • Cytochrome P-450 CYP3A Inhibitors
  • Quinoxalines
  • VP40 protein, virus
  • Viral Matrix Proteins
  • Cytochrome P-450 CYP3A
  • CYP3A4 protein, human