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

Muneebah Adams, Carmen de Kock, Peter J. Smith, Kirkwood M. Land, Nicole Liu, Melissa Hopper, Allyson Hsiao, Andrew R. Burgoyne, Tameryn Stringer, Mervin Meyer, Lubbe Wiesner, Kelly Chibale, Gregory S. Smith

Research output: Contribution to journalArticlepeer-review

42 Citations (SciVal)

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.
Original languageEnglish
Pages (from-to)2456-2468
Number of pages13
JournalDalton Transactions
Volume44
Issue number5
Early online date5 Jan 2015
DOIs
Publication statusPublished - 7 Feb 2015

Cite this