Small molecule inhibitors of HIVgp41 N-heptad repeat trimer formation

Bioorg Med Chem Lett. 2015 Jul 15;25(14):2853-9. doi: 10.1016/j.bmcl.2015.04.067. Epub 2015 Apr 28.

Abstract

Identification of mechanistically novel anti-HIV fusion inhibitors was accomplished using a computer-aided structure-based design approach with the goal of blocking the formation of the N-heptad repeat (NHR) trimer of the viral protein gp41. A virtual screening strategy that included per-residue interaction patterns (footprints) was employed to identify small molecules compatible with putative binding pockets at the internal interface of the NHR helices at the core native viral six-helix bundle. From a screen of ∼2.8 million compounds using the DOCK program, 120 with favorable energetic and footprint overlap characteristics were purchased and experimentally tested leading to two compounds with favorable cell-cell fusion (IC50) and cytotoxicity profiles. Importantly, both hits were identified on the basis of scores containing footprint overlap terms and would not have been identified using the standard DOCK energy function alone. To our knowledge, these compounds represent the first reported small molecules that inhibit viral entry via the proposed NHR-trimer obstruction mechanism.

Keywords: DOCK; Docking; Footprint similarity; HIV; Virtual screening; gp41.

Publication types

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

MeSH terms

  • Binding Sites
  • Cell Line
  • Cell Survival / drug effects
  • Drug Design
  • HIV Envelope Protein gp41 / antagonists & inhibitors*
  • HIV Envelope Protein gp41 / metabolism
  • HIV Fusion Inhibitors / chemistry*
  • HIV Fusion Inhibitors / metabolism
  • HIV Fusion Inhibitors / toxicity
  • HIV-1 / metabolism*
  • Humans
  • Molecular Docking Simulation
  • Protein Multimerization / drug effects
  • Protein Structure, Tertiary
  • Small Molecule Libraries / chemistry*
  • Small Molecule Libraries / metabolism
  • Small Molecule Libraries / pharmacology
  • Virus Internalization / drug effects

Substances

  • HIV Envelope Protein gp41
  • HIV Fusion Inhibitors
  • Small Molecule Libraries