Interrogating a hexokinase-selected small-molecule library for inhibitors of Plasmodium falciparum hexokinase

Antimicrob Agents Chemother. 2013 Aug;57(8):3731-7. doi: 10.1128/AAC.00662-13. Epub 2013 May 28.

Abstract

Parasites in the genus Plasmodium cause disease throughout the tropic and subtropical regions of the world. P. falciparum, one of the deadliest species of the parasite, relies on glycolysis for the generation of ATP while it inhabits the mammalian red blood cell. The first step in glycolysis is catalyzed by hexokinase (HK). While the 55.3-kDa P. falciparum HK (PfHK) shares several biochemical characteristics with mammalian HKs, including being inhibited by its products, it has limited amino acid identity (~26%) to the human HKs, suggesting that enzyme-specific therapeutics could be generated. To that end, interrogation of a selected small-molecule library of HK inhibitors has identified a class of PfHK inhibitors, isobenzothiazolinones, some of which have 50% inhibitory concentrations (IC50s) of <1 μM. Inhibition was reversible by dilution but not by treatment with a reducing agent, suggesting that the basis for enzyme inactivation was not covalent association with the inhibitor. Lastly, six of these compounds and the related molecule ebselen inhibited P. falciparum growth in vitro (50% effective concentration [EC50] of ≥ 0.6 and <6.8 μM). These findings suggest that the chemotypes identified here could represent leads for future development of therapeutics against P. falciparum.

Publication types

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

MeSH terms

  • Amino Acid Sequence
  • Antimalarials / pharmacology*
  • Azoles / pharmacology
  • Benzothiazoles / pharmacology*
  • Dose-Response Relationship, Drug
  • Enzyme Inhibitors / pharmacology
  • Glycolysis
  • Hexokinase / antagonists & inhibitors*
  • Inhibitory Concentration 50
  • Isoindoles
  • Molecular Sequence Data
  • Organoselenium Compounds / pharmacology
  • Parasitic Sensitivity Tests
  • Plasmodium falciparum / drug effects*
  • Plasmodium falciparum / enzymology
  • Plasmodium falciparum / growth & development
  • Protozoan Proteins / antagonists & inhibitors*
  • Recombinant Proteins / metabolism
  • Small Molecule Libraries / pharmacology*
  • Structure-Activity Relationship

Substances

  • Antimalarials
  • Azoles
  • Benzothiazoles
  • Enzyme Inhibitors
  • Isoindoles
  • Organoselenium Compounds
  • Protozoan Proteins
  • Recombinant Proteins
  • Small Molecule Libraries
  • ebselen
  • Hexokinase

Associated data

  • SWISSPROT/Q02155