Molecular Design and Synthesis of Ivermectin Hybrids Targeting Hepatic and Erythrocytic Stages of Plasmodium Parasites

J Med Chem. 2020 Feb 27;63(4):1750-1762. doi: 10.1021/acs.jmedchem.0c00033. Epub 2020 Feb 14.

Abstract

Ivermectin is a powerful endectocide, which reduces the incidence of vector-borne diseases. Besides its strong insecticidal effect on mosquito vectors of the disease, ivermectin inhibits Plasmodium falciparum sporogonic and blood stage development and impairs Plasmodium berghei development inside hepatocytes, both in vitro and in vivo. Herein, we present the first report on structural modification of ivermectin to produce dual-action molecular hybrids with good structure-dependent in vitro activity against both the hepatic and erythrocytic stages of P. berghei and P. falciparum infection, suggesting inclusion of ivermectin antimalarial hybrids in malaria control strategies. The most active hybrid displayed over threefold and 10-fold higher in vitro activity than ivermectin against hepatic and blood stage infections, respectively. Although an overwhelming insecticidal effect against Anopheles stephensi mosquitoes in laboratory conditions was not noticed, in silico docking analysis supports allosteric binding to glutamate-gated chloride channels similar to ivermectin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anopheles / drug effects
  • Antimalarials / chemical synthesis
  • Antimalarials / pharmacology*
  • Binding Sites
  • Chloride Channels / chemistry
  • Chloride Channels / metabolism
  • Drug Design
  • Insecticides / chemical synthesis
  • Insecticides / pharmacology
  • Ivermectin / analogs & derivatives*
  • Ivermectin / metabolism
  • Ivermectin / pharmacology*
  • Molecular Docking Simulation
  • Molecular Structure
  • Parasitic Sensitivity Tests
  • Plasmodium berghei / drug effects*
  • Plasmodium berghei / growth & development
  • Plasmodium falciparum / drug effects*
  • Plasmodium falciparum / growth & development
  • Protein Binding
  • Structure-Activity Relationship

Substances

  • Antimalarials
  • Chloride Channels
  • Insecticides
  • glutamate-gated chloride channels
  • Ivermectin