Optimization and Evaluation of Antiparasitic Benzamidobenzoic Acids as Inhibitors of Kinetoplastid Hexokinase 1

ChemMedChem. 2017 Dec 7;12(23):1994-2005. doi: 10.1002/cmdc.201700592. Epub 2017 Nov 16.

Abstract

Kinetoplastid-based infections are neglected diseases that represent a significant human health issue. Chemotherapeutic options are limited due to toxicity, parasite susceptibility, and poor patient compliance. In response, we studied a molecular-target-directed approach involving intervention of hexokinase activity-a pivotal enzyme in parasite metabolism. A benzamidobenzoic acid hit with modest biochemical inhibition of Trypanosoma brucei hexokinase 1 (TbHK1, IC50 =9.1 μm), low mammalian cytotoxicity (IMR90 cells, EC50 >25 μm), and no appreciable activity on whole bloodstream-form (BSF) parasites was optimized to afford a probe with improved TbHK1 potency and, significantly, efficacy against whole BSF parasites (TbHK1, IC50 =0.28 μm; BSF, ED50 =1.9 μm). Compounds in this series also inhibited the hexokinase enzyme from Leishmania major (LmHK1), albeit with less potency than toward TbHK1, suggesting that inhibition of the glycolytic pathway may be a promising opportunity to target multiple disease-causing trypanosomatid protozoa.

Keywords: antiparasitic agents; benzamidobenzamidines; leishmania; sleeping sickness; trypanosomes.

Publication types

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

MeSH terms

  • Antiparasitic Agents / chemical synthesis
  • Antiparasitic Agents / chemistry
  • Antiparasitic Agents / pharmacology*
  • Benzamides / chemical synthesis
  • Benzamides / chemistry
  • Benzamides / pharmacology*
  • Benzoates / chemical synthesis
  • Benzoates / chemistry
  • Benzoates / pharmacology*
  • Dose-Response Relationship, Drug
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Hexokinase / antagonists & inhibitors*
  • Hexokinase / metabolism
  • Leishmania major / drug effects
  • Leishmania major / enzymology
  • Leishmania major / growth & development
  • Molecular Structure
  • Parasitic Sensitivity Tests
  • Structure-Activity Relationship
  • Trypanosoma brucei brucei / drug effects
  • Trypanosoma brucei brucei / enzymology
  • Trypanosoma brucei brucei / growth & development

Substances

  • Antiparasitic Agents
  • Benzamides
  • Benzoates
  • Enzyme Inhibitors
  • Hexokinase