Stringer T., Taylor D., Guzgay H., Shokar A., Au A., Smith P.J., Hendricks D.T., Land K.M., Egan T.J., Smith G.S.
Department of Chemistry, University of Cape Town, Rondebosch, South Africa; Division of Clinical Pharmacology, Department of Medicine, University of Cape Town Medical School, Observatory, South Africa; Division of Medical Biochemistry, University of Cape Town, Rondebosch, South Africa; Department of Biological Sciences, University of the Pacific, Stockton, CA, United States
Stringer, T., Department of Chemistry, University of Cape Town, Rondebosch, South Africa; Taylor, D., Division of Clinical Pharmacology, Department of Medicine, University of Cape Town Medical School, Observatory, South Africa; Guzgay, H., Division of Medical Biochemistry, University of Cape Town, Rondebosch, South Africa; Shokar, A., Department of Biological Sciences, University of the Pacific, Stockton, CA, United States; Au, A., Department of Biological Sciences, University of the Pacific, Stockton, CA, United States; Smith, P.J., Division of Clinical Pharmacology, Department of Medicine, University of Cape Town Medical School, Observatory, South Africa; Hendricks, D.T., Division of Medical Biochemistry, University of Cape Town, Rondebosch, South Africa; Land, K.M., Department of Biological Sciences, University of the Pacific, Stockton, CA, United States; Egan, T.J., Department of Chemistry, University of Cape Town, Rondebosch, South Africa; Smith, G.S., Department of Chemistry, University of Cape Town, Rondebosch, South Africa
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. © 2015 Royal Society of Chemistry.