Synthesis and antileishmanial activities of 4,5-di-substituted acridines as compared to their 4-mono-substituted homologues

Bioorg Med Chem. 2005 Oct 1;13(19):5560-8. doi: 10.1016/j.bmc.2005.06.045.

Abstract

Newly synthesized 4,5-di-substituted acridines were assessed for in vitro antileishmanial activities as compared to those of their 4-mono-substituted homologues. Mono-substituted acridines exhibited a weak specificity for Leishmania parasites. Di-substituted acridines, on the contrary, displayed interesting amastigote-specific activities through a mechanism of action that might not involve intercalation to DNA. This antileishmanial property, associated with a low antiproliferative activity towards human cells, led to the identification of a new class of promising acridine derivatives such as 4,5-bis(hydroxymethyl)acridine with a nonclassical mechanism of action based on the inhibition of Leishmania internalization within macrophages. In the meantime, the effects of experimental lighting on the biological properties of acridines were assessed: experimental lighting did not significantly improve the antileishmanial activity of the compounds since it produced a greater toxicity against human cells.

MeSH terms

  • Acridines / chemical synthesis*
  • Acridines / classification
  • Acridines / pharmacology*
  • Animals
  • Cell Line
  • Cell Proliferation / drug effects
  • Dose-Response Relationship, Drug
  • Humans
  • Leishmania / drug effects*
  • Macrophages / drug effects
  • Macrophages / parasitology
  • Molecular Structure
  • Monocytes / drug effects
  • Monocytes / parasitology
  • Parasitic Sensitivity Tests
  • Species Specificity

Substances

  • Acridines