Synthesis and evaluation of new polynuclear organometallic Ru(II), Rh(III) and Ir(III) pyridyl ester complexes as in vitro antiparasitic and antitumor agents

Prinessa Chellan; Kirkwood M. Land; Ajit Shokar; Aaron Au; Seung Hwan An; Dale Taylor; Peter J. Smith; Tina Riedel; Paul J. Dyson; Kelly Chibale; Gregory S. Smith

doi:10.1039/C3DT52090K

Synthesis and evaluation of new polynuclear organometallic Ru(ii), Rh(iii) and Ir(iii) pyridyl ester complexes as in vitro antiparasitic and antitumor agents†

Prinessa Chellan,^a Kirkwood M. Land,^b Ajit Shokar,^b Aaron Au,^b Seung Hwan An,^b Dale Taylor,^c Peter J. Smith,^c Tina Riedel,^d Paul J. Dyson,^d Kelly Chibale^a and Gregory S. Smith*^a

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^a Department of Chemistry, University of Cape Town, Private Bag, Rondebosch 7701, South Africa
E-mail: gregory.smith@uct.ac.za
Fax: +27-21-6505195
Tel: +27-21-6505279

^b Department of Biological Sciences, University of the Pacific, Stockton, CA 95211, USA

^c Division of Pharmacology, Department of Medicine, University of Cape Town, K45, OMB, Groote Schuur Hospital, Observatory, South Africa

^d Institut des Sciences et Ingénierie Chimiques, Ecole Polytechnique Fédérale de Lausanne (EPFL), CH-1015 Lausanne, Switzerland

Abstract

New polynuclear organometallic Platinum Group Metal (PGM) complexes containing di- and tripyridyl ester ligands have been synthesised and characterised using analytical and spectroscopic techniques including ¹H, ¹³C NMR and infrared spectroscopy. Reaction of these polypyridyl ester ligands with either [Ru(p-cymene)Cl₂]₂, [Rh(C₅Me₅)Cl₂]₂ or [Ir(C₅Me₅)Cl₂]₂ dimers yielded the corresponding di- or trinuclear organometallic complexes. The polyaromatic ester ligands act as monodentate donors to each metal centre and this coordination mode was confirmed upon elucidation of the molecular structures for two of the dinuclear complexes. The di- and trinuclear PGM complexes synthesized were evaluated for inhibitory effects on the human protozoal parasites Plasmodium falciparum strain NF54 (chloroquine sensitive), Trichomonas vaginalis strain G3 and the human ovarian cancer cell lines, A2780 (cisplatin-sensitive) and A2780cisR (cisplatin-resistant) cell lines. All of the complexes were observed to have moderate to high antiplasmodial activities and the compounds with the best activities were evaluated for their ability to inhibit formation of synthetic hemozoin in a cell free medium. The in vitro antitumor evaluation of these complexes revealed that the trinuclear pyridyl ester complexes demonstrated moderate activities against the two tumor cell lines and were also less toxic to model non-tumorous cells.

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Synthesis and evaluation of new polynuclear organometallic Ru(ii), Rh(iii) and Ir(iii) pyridyl ester complexes as in vitro antiparasitic and antitumor agents†

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Synthesis and evaluation of new polynuclear organometallic Ru(II), Rh(III) and Ir(III) pyridyl ester complexes as in vitro antiparasitic and antitumor agents

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