Bistacrines as potential antitrypanosomal agents

Bioorg Med Chem. 2017 Aug 15;25(16):4526-4531. doi: 10.1016/j.bmc.2017.06.051. Epub 2017 Jul 1.

Abstract

Human African Trypanosomiasis (HAT) is caused by two subspecies of the genus Trypanosoma, namely Trypanosoma brucei rhodesiense and Trypanosoma brucei gambiense. The disease is fatal if left untreated and therapy is limited due to only five non-adequate drugs currently available. In preliminary studies, dimeric tacrine derivatives were found to inhibit parasite growth with IC50-values in the nanomolar concentration range. This prompted the synthesis of a small, but smart library of monomeric and dimeric tacrine-type compounds and their evaluation of antiprotozoal activity. Rhodesain, a lysosomal cathepsin-L like cysteine protease of T. brucei rhodesiense is essential for parasite survival and likely target of the tacrine derivatives. In addition, the inhibition of trypanothione reductase by bistacrines was found. This flavoprotein oxidoreductase is the main defense against oxidative stress in the thiol redox system unique for protozoa.

Keywords: Antitrypanosomal drugs; Bistacrine; Rhodesain; Trypanothione reductase.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cell Line
  • Cell Proliferation / drug effects
  • Dose-Response Relationship, Drug
  • Mice
  • Molecular Structure
  • Parasitic Sensitivity Tests
  • Structure-Activity Relationship
  • Tacrine / chemistry
  • Tacrine / pharmacology*
  • Trypanocidal Agents / pharmacology*
  • Trypanosoma brucei brucei / cytology
  • Trypanosoma brucei brucei / drug effects*
  • Trypanosomiasis, African / drug therapy*

Substances

  • Trypanocidal Agents
  • Tacrine