Discovery of 4-oxoquinolines, a new chemical class of anti-HIV-1 compounds

Antiviral Res. 2019 Feb:162:101-109. doi: 10.1016/j.antiviral.2018.12.012. Epub 2018 Dec 21.

Abstract

Antiretroviral therapy (ART) against HIV-1 infection offers the promise of controlling disease progression and prolonging the survival of HIV-1-infected patients. However, even the most potent ART regimens available today cannot cure HIV-1. Because patients will be exposed to ART for many years, physicians and researchers must anticipate the emergence of drug-resistant HIV-1, potential adverse effects of the current drugs, and need for future drug development. In this study, we screened a small-molecule compound library using cell-based anti-HIV-1 assays and discovered a series of novel anti-HIV-1 compounds, 4-oxoquinolines. These compounds exhibited potent anti-HIV-1 activity (EC50 < 0.1 μM) with high selectivity indexes (CC50/EC50 > 2500) and favorable pharmacokinetic profiles in mice. Surprisingly, our novel compounds have a chemical backbone similar to the clinically used integrase (IN) strand transfer inhibitor (INSTI) elvitegravir, although they lack the crucial 3-carboxylate moiety needed for the common INSTI diketo motif. Indeed, the new 4-oxoquinoline derivatives have no detectable INSTI activity. In addition, various drug-resistant HIV-1 strains did not display cross resistance to these compounds. Interestingly, time-of-addition experiments indicated that the 4-oxoquinoline derivative remains its anti-HIV-1 activity even after the viral integration stage. Furthermore, the compounds significantly suppressed p24 antigen production in HIV-1 latently infected cells exposed with tumor necrosis factor alpha. These findings suggest that our 4-oxoquinoline derivatives with no 3-carboxylate moiety may become novel lead compounds in the development of anti-HIV-1 drugs.

Keywords: 4-Oxoquinoline; Anti-HIV; Antiviral compound; Integrase strand-transfer inhibitor; Latently infected cell; Tat.

Publication types

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

MeSH terms

  • 4-Quinolones / pharmacokinetics*
  • 4-Quinolones / pharmacology*
  • Animals
  • Anti-HIV Agents / pharmacokinetics*
  • Anti-HIV Agents / pharmacology*
  • Drug Discovery
  • HEK293 Cells
  • HIV-1 / drug effects*
  • Heterocyclic Compounds, 3-Ring / pharmacology
  • Humans
  • Male
  • Mice
  • Mice, Inbred ICR
  • Microbial Sensitivity Tests
  • Small Molecule Libraries

Substances

  • 4-Quinolones
  • Anti-HIV Agents
  • Heterocyclic Compounds, 3-Ring
  • Small Molecule Libraries