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Exploring the Versatility of Cycloplatinated Thiosemicarbazones as Antitumor and Antiparasitic Agents

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Department of Chemistry, University of Cape Town, Private Bag, Rondebosch 7701, South Africa
Department of Biological Sciences, University of the Pacific, Stockton, California 95211, United States
§ Institut des Sciences et Ingénierie Chimiques, Ecole Polytechnique Fédérale de Lausanne (EPFL), CH-1015 Lausanne, Switzerland
Division of Pharmacology, Department of Medicine, University of Cape Town, K45, OMB, Groote Schuur Hospital, Observatory, 7925, South Africa
Institute of Infectious Disease and Molecular Medicine, University of Cape Town, Rondebosch 7701, South Africa
*Tel: +27-21-6505279. Fax: +27-21-6505195. E-mail: [email protected]
Cite this: Organometallics 2012, 31, 16, 5791–5799
Publication Date (Web):July 26, 2012
https://doi.org/10.1021/om300334z
Copyright © 2012 American Chemical Society

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    Abstract

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    Tridentate cycloplatinated thiosemicarbazone complexes have been prepared from a biologically significant ligand, 3,4-dichloroacetophenone thiosemicarbazone (1). The tetranuclear complex 2 was prepared by reaction of the ligand with K2[PtCl4]. Two mononuclear (3 and 4) and two dinuclear (5 and 6) complexes were isolated upon cleavage of the Pt–Sbridging bonds of the tetranuclear complex 2 with the appropriate phosphane ligand. Each complex was characterized using various analytical and spectroscopic techniques, and the molecular structures of 24 were also elucidated. The in vitro antiparasitic activities of these complexes against Plasmodium falciparum strains (D10 (chloroquine sensitive) and Dd2 (chloroquine resistant)) and Trichomonas vaginalis have been determined. Preliminary studies into their potential plasmodial target in the form of β-hematin formation inhibition assays were also completed. Preliminary results suggest that ligand 1 and complex 3 do not hinder formation of β-hematin. The antiproliferative activity of the complexes against the cisplatin-senstive A2780 and cisplatin-resistant A2780cisR human ovarian cancer cell lines has been evaluated. The complexes were found to exhibit moderate to weak inhibitory activities.

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    CIF files giving crystallographic data for complexes 2·3DMSO, 3·2DMSO, and 4. This material is available free of charge via the Internet at http://pubs.acs.org. CCDC 866790, 866791, and 866792 also contain supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, U.K.; fax (internat.) +44-1223/336-033; e-mail [email protected]).

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