Selective activity of 2,4-diaryl-1,2,3,4-tetrahydroquinolines on Trypanosoma cruzi epimastigotes and amastigotes expressing β-galactosidase

Bioorg Med Chem Lett. 2013 Sep 1;23(17):4851-6. doi: 10.1016/j.bmcl.2013.06.079. Epub 2013 Jul 12.

Abstract

The growth inhibitory effect on Trypanosoma cruzi epimastigotes and the unspecific cytotoxicity over NCTC-929 fibroblasts of two series of previously synthesized 2,4-diaryl-1,2,3,4-tetrahydroquinolines (THQ), have been studied in vitro and compared with those of benznidazole (BZ). Derivatives AR39, AR40, AR41, AR91 and DM15 achieved outstanding selectivity indexes (SI) on the extracellular form (SITHQ>SIBZ>9.44) and thus, were tested in a more specific in vitro assay against amastigotes, showing less effectiveness than the reference drug (SIBZ>320) but also accomplishing great selectivity on the intracellular stage (SITHQ>25). These promising results, supported by the in silico prediction of high bioavailability and less potential risk than benznidazole, reveal several tetrahydroquinolines as prototypes of potential antichagasic drugs.

Keywords: Cytotoxicity; Lipinski’s rule; OSIRIS software; Tetrahydroquinolines; Trypanosoma cruzi.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cell Line
  • Chagas Disease / drug therapy
  • Fibroblasts / cytology
  • Fibroblasts / drug effects
  • Gene Expression
  • Humans
  • Mice
  • Nitroimidazoles / chemistry
  • Nitroimidazoles / pharmacology
  • Nitroimidazoles / toxicity
  • Quinolines / chemistry*
  • Quinolines / pharmacology*
  • Quinolines / toxicity
  • Trypanocidal Agents / chemistry*
  • Trypanocidal Agents / pharmacology*
  • Trypanocidal Agents / toxicity
  • Trypanosoma cruzi / drug effects*
  • Trypanosoma cruzi / enzymology*
  • Trypanosoma cruzi / genetics
  • Trypanosoma cruzi / growth & development
  • beta-Galactosidase / genetics

Substances

  • Nitroimidazoles
  • Quinolines
  • Trypanocidal Agents
  • 1,2,3,4-tetrahydroquinoline
  • beta-Galactosidase
  • benzonidazole