High-affinity recognition of HIV-1 frameshift-stimulating RNA alters frameshifting in vitro and interferes with HIV-1 infectivity

J Med Chem. 2014 Feb 13;57(3):723-32. doi: 10.1021/jm401438g. Epub 2014 Jan 15.

Abstract

The life cycle of the human immunodeficiency virus type 1 (HIV-1) has an absolute requirement for ribosomal frameshifting during protein translation in order to produce the polyprotein precursor of the viral enzymes. While an RNA stem-loop structure (the "HIV-1 Frameshift Stimulating Signal", or HIV-1 FSS) controls the frameshift efficiency and has been hypothesized as an attractive therapeutic target, developing compounds that selectively bind this RNA and interfere with HIV-1 replication has proven challenging. Building on our prior discovery of a "hit" molecule able to bind this stem-loop, we now report the development of compounds displaying high affinity for the HIV-1 FSS. These compounds are able to enhance frameshifting more than 50% in a dual-luciferase assay in human embryonic kidney cells, and they strongly inhibit the infectivity of pseudotyped HIV-1 virions.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Anti-HIV Agents / chemical synthesis
  • Anti-HIV Agents / chemistry
  • Anti-HIV Agents / pharmacology*
  • Cell Membrane Permeability
  • Cell Survival / drug effects
  • Disulfides / chemical synthesis
  • Disulfides / chemistry
  • Disulfides / pharmacology
  • Frameshifting, Ribosomal
  • HEK293 Cells
  • HIV-1 / drug effects
  • HIV-1 / genetics*
  • HIV-1 / pathogenicity
  • Humans
  • Luciferases, Firefly / genetics
  • Luciferases, Firefly / metabolism
  • Luciferases, Renilla / genetics
  • Luciferases, Renilla / metabolism
  • Nucleic Acid Conformation
  • Quinolines / chemical synthesis
  • Quinolines / chemistry
  • Quinolines / pharmacology*
  • RNA, Viral / genetics*
  • Stereoisomerism
  • Virion / drug effects
  • Virion / pathogenicity
  • Virus Replication / drug effects

Substances

  • Anti-HIV Agents
  • Disulfides
  • Quinolines
  • RNA, Viral
  • Luciferases, Renilla
  • Luciferases, Firefly