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Issue 5, 2015
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Improved antiparasitic activity by incorporation of organosilane entities into half-sandwich ruthenium(II) and rhodium(III) thiosemicarbazone complexes

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Abstract

A series of ferrocenyl- and aryl-functionalised organosilane thiosemicarbazone compounds was obtained via a nucleophilic substitution reaction with an amine-terminated organosilane. The thiosemicarbazone (TSC) ligands were further reacted with either a ruthenium dimer [(η6-iPrC6H4Me)Ru(μ-Cl)Cl]2 or a rhodium dimer [(Cp*)Rh(μ-Cl)Cl]2 to yield a series of cationic mono- and binuclear complexes. The thiosemicarbazone ligands, as well as their metal complexes, were characterised using NMR and IR spectroscopy, and mass spectrometry. The molecular structure of the binuclear ruthenium(II) complex was determined by single-crystal X-ray diffraction analysis. The thiosemicarbazones and their complexes were evaluated for their in vitro antiplasmodial activities against the chloroquine-sensitive (NF54) and chloroquine-resistant (Dd2) Plasmodium falciparum strains, displaying activities in the low micromolar range. Selected compounds were screened for potential β-haematin inhibition activity, and it was found that two Rh(III) complexes exhibited moderate to good inhibition. Furthermore, the compounds were screened for their antitrichomonal activities against the G3 Trichomonas vaginalis strain, revealing a higher percentage of growth inhibition for the ruthenium and rhodium complexes over their corresponding ligand.

Graphical abstract: Improved antiparasitic activity by incorporation of organosilane entities into half-sandwich ruthenium(ii) and rhodium(iii) thiosemicarbazone complexes

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Publication details

The article was received on 20 Oct 2014, accepted on 05 Dec 2014 and first published on 05 Jan 2015


Article type: Paper
DOI: 10.1039/C4DT03234A
Citation: Dalton Trans., 2015,44, 2456-2468
  • Open access: Creative Commons BY-NC license
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    Improved antiparasitic activity by incorporation of organosilane entities into half-sandwich ruthenium(II) and rhodium(III) thiosemicarbazone complexes

    M. Adams, C. de Kock, P. J. Smith, K. M. Land, N. Liu, M. Hopper, A. Hsiao, A. R. Burgoyne, T. Stringer, M. Meyer, L. Wiesner, K. Chibale and G. S. Smith, Dalton Trans., 2015, 44, 2456
    DOI: 10.1039/C4DT03234A

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