Polyamine quinoline rhodium complexes: synthesis and pharmacological evaluation as antiparasitic agents against Plasmodium falciparum and Trichomonas vaginalis

Dalton Trans. 2015 Sep 7;44(33):14906-17. doi: 10.1039/c5dt02378e.

Abstract

A series of mono- and bis-salicylaldimine ligands and their corresponding Rh(i) complexes were prepared. The compounds were characterised using standard spectroscopic techniques including NMR, IR spectroscopy and mass spectrometry. The salicylaldimine ligands and complexes were screened for antiparasitic activity against two strains of Plasmodium falciparum i.e. the NF54 CQ-sensitive and K1 CQ-resistant strain as well as against the G3 isolate of Trichomonas vaginalis. The monomeric salicylaldimine quinolines exhibited good activity against the NF54 strain and the dimeric salicylaldimine quinolines exhibited no cross resistance across the two strains. The binuclear 5-chloro Rh(i) complex displayed the best activity against the Trichomonas vaginalis parasite, possibly a consequence of its enhanced lipophilicity. The compounds were also screened for cytotoxicity in vitro against WHCO1 oesophageal cancer cells. The monomeric salicylaldimine quinolines exhibited high selectivity towards malaria parasites compared to cancer cells, while the dimeric compounds were less selective.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antiparasitic Agents / chemical synthesis
  • Antiparasitic Agents / chemistry
  • Antiparasitic Agents / pharmacology*
  • Coordination Complexes / chemical synthesis
  • Coordination Complexes / chemistry
  • Coordination Complexes / pharmacology
  • Female
  • Humans
  • Malaria, Falciparum / drug therapy*
  • Plasmodium falciparum / drug effects*
  • Polyamines / chemical synthesis
  • Polyamines / chemistry
  • Polyamines / pharmacology
  • Quinolines / chemical synthesis
  • Quinolines / chemistry
  • Quinolines / pharmacology*
  • Rhodium / chemistry
  • Rhodium / pharmacology*
  • Structure-Activity Relationship
  • Trichomonas Vaginitis / drug therapy*
  • Trichomonas vaginalis / drug effects*

Substances

  • Antiparasitic Agents
  • Coordination Complexes
  • Polyamines
  • Quinolines
  • Rhodium
  • quinoline