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

Authors

Muneebah Adama, University of Cape Town
Carmen de Kock, University of Cape Town
Peter J. Smith, University of Cape Town
Kirkwood M. Land, University of the PacificFollow
Nicole Liu, University of the Pacific
Melissa Hopper, University of the Pacific
Allyson Hsiao, University of the Pacific
Andrew R. Burgoyne, University of Cape Town
Tameryn Stringer, University of Cape Town
Mervin Meyer, University of the Western Cape
Lubbe Wiesner, University of the Western Cape
Kelly Chibale, University of Cape Town
Gregory S. Smith, University of Cape TownFollow

ORCID

Kirkwood M. Land: 0000-0001-5951-9630

Document Type

Article

Publication Title

Dalton Transactions

Department

Biological Sciences

ISSN

Print: 1477-9226, Electronic: 1477-9234

Volume

44

Issue

5

DOI

10.1039/c4dt03234a

First Page

2456

Last Page

2468

Publication Date

1-15-2015

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 [(η(6-i)PrC6H4Me)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.

Recommended Citation

Adama, M., de Kock, C., Smith, P. J., Land, K. M., Liu, N., Hopper, M., Hsiao, A., Burgoyne, A. R., Stringer, T., Meyer, M., Wiesner, L., Chibale, K., & Smith, G. S. (2015). Improved antiparasitic activity by incorporation of organosilane entities into half-sandwich ruthenium(ii) and rhodium(iii) thiosemicarbazone complexes. Dalton Transactions, 44(5), 2456–2468. DOI: 10.1039/c4dt03234a
https://scholarlycommons.pacific.edu/cop-facarticles/805