Fast-Acting Small Molecules Targeting Malarial Aspartyl Proteases, Plasmepsins, Inhibit Malaria Infection at Multiple Life Stages

ACS Infect Dis. 2019 Feb 8;5(2):184-198. doi: 10.1021/acsinfecdis.8b00197. Epub 2019 Jan 2.

Abstract

The eradication of malaria remains challenging due to the complex life cycle of Plasmodium and the rapid emergence of drug-resistant forms of Plasmodium falciparum and Plasmodium vivax. New, effective, and inexpensive antimalarials against multiple life stages of the parasite are urgently needed to combat the spread of malaria. Here, we synthesized a set of novel hydroxyethylamines and investigated their activities in vitro and in vivo. All of the compounds tested had an inhibitory effect on the blood stage of P. falciparum at submicromolar concentrations, with the best showing 50% inhibitory concentrations (IC50) of around 500 nM against drug-resistant P. falciparum parasites. These compounds showed inhibitory actions against plasmepsins, a family of malarial aspartyl proteases, and exhibited a marked killing effect on blood stage Plasmodium. In chloroquine-resistant Plasmodium berghei and P. berghei ANKA infected mouse models, treating mice with both compounds led to a significant decrease in blood parasite load. Importantly, two of the compounds displayed an inhibitory effect on the gametocyte stages (III-V) of P. falciparum in culture and the liver-stage infection of P. berghei both in in vitro and in vivo. Altogether, our findings suggest that fast-acting hydroxyethylamine-phthalimide analogs targeting multiple life stages of the parasite could be a valuable chemical lead for the development of novel antimalarial drugs.

Keywords: hydroxyethylamine; marked killing inhibitor; multistage malaria inhibitor; phthalimide; plasmepsins.

Publication types

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

MeSH terms

  • Animals
  • Antimalarials / chemical synthesis
  • Antimalarials / pharmacology*
  • Aspartic Acid Endopeptidases / metabolism*
  • Chloroquine / analogs & derivatives
  • Drug Discovery
  • Ethylamines / chemical synthesis
  • Ethylamines / pharmacology*
  • Inhibitory Concentration 50
  • Life Cycle Stages
  • Mice
  • Phthalimides / pharmacology
  • Plasmodium berghei / drug effects
  • Plasmodium falciparum / drug effects*
  • Plasmodium falciparum / enzymology

Substances

  • Antimalarials
  • Ethylamines
  • Phthalimides
  • phthalimide
  • Chloroquine
  • Aspartic Acid Endopeptidases
  • plasmepsin