Antiplasmodial activity and mechanism of action of RSM-932A, a promising synergistic inhibitor of Plasmodium falciparum choline kinase

Antimicrob Agents Chemother. 2013 Dec;57(12):5878-88. doi: 10.1128/AAC.00920-13. Epub 2013 Sep 16.

Abstract

We have investigated the mechanism of action of inhibition of the choline kinase of P. falciparum (p.f.-ChoK) by two inhibitors of the human ChoKα, MN58b and RSM-932A, which have previously been shown to be potent antitumoral agents. The efficacy of these inhibitors against p.f.-ChoK is investigated using enzymatic and in vitro assays. While MN58b may enter the choline/phosphocholine binding site, RSM-932A appears to have an altogether novel mechanism of inhibition and is synergistic with respect to both choline and ATP. A model of inhibition for RSM-932A in which this inhibitor traps p.f.-ChoK in a phosphorylated intermediate state blocking phosphate transfer to choline is presented. Importantly, MN58b and RSM-932A have in vitro inhibitory activity in the low nanomolar range and are equally effective against chloroquine-sensitive and chloroquine-resistant strains. RSM-932A and MN58b significantly reduced parasitemia and induced the accumulation of trophozoites and schizonts, blocking intraerythrocytic development and interfering with parasite egress or invasion, suggesting a delay of the parasite maturation stage. The present data provide two new potent structures for the development of antimalarial compounds and validate p.f.-ChoK as an accessible drug target against the parasite.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenosine Triphosphate / chemistry
  • Adenosine Triphosphate / metabolism
  • Aniline Compounds / pharmacology*
  • Antimalarials / pharmacology*
  • Antineoplastic Agents / pharmacology*
  • Butanes / pharmacology*
  • Chloroquine / pharmacology
  • Choline / chemistry
  • Choline / metabolism
  • Choline Kinase / antagonists & inhibitors*
  • Choline Kinase / chemistry
  • Choline Kinase / metabolism
  • Dose-Response Relationship, Drug
  • Drug Synergism
  • Enzyme Inhibitors / pharmacology
  • Erythrocytes / drug effects
  • Erythrocytes / parasitology
  • Escherichia coli / genetics
  • Humans
  • Kinetics
  • Parasitic Sensitivity Tests
  • Phosphorylation / drug effects
  • Plasmodium falciparum / drug effects*
  • Plasmodium falciparum / enzymology
  • Plasmodium falciparum / growth & development
  • Protozoan Proteins / antagonists & inhibitors*
  • Protozoan Proteins / chemistry
  • Protozoan Proteins / metabolism
  • Pyridinium Compounds / pharmacology*
  • Quinolinium Compounds / pharmacology*
  • Recombinant Proteins / chemistry
  • Recombinant Proteins / metabolism
  • Trophozoites / drug effects
  • Trophozoites / enzymology
  • Trophozoites / growth & development

Substances

  • 1,4-(4-4'-Bis-((4-(dimethylamine)pyridinium-1-yl) methyl)diphenyl)butane dibromide
  • Aniline Compounds
  • Antimalarials
  • Antineoplastic Agents
  • Butanes
  • Enzyme Inhibitors
  • Protozoan Proteins
  • Pyridinium Compounds
  • Quinolinium Compounds
  • RSM-932A
  • Recombinant Proteins
  • Chloroquine
  • Adenosine Triphosphate
  • Choline Kinase
  • Choline