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Materials 2013, 6(11), 5352-5366; doi:10.3390/ma6115352
Article

Synthesis, Molecular Structure and Cytotoxicity of Molecular Materials Based on Water Soluble Half-Sandwich Rh(III) and Ir(III) Tetranuclear Metalla-Cycles

1
,
2
,
2
 and
1,*
1 Institute of Chemistry, University of Neuchatel, Avenue de Bellevaux 51, Neuchatel CH-2000, Switzerland 2 Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL), Lausanne CH-1015, Switzerland
* Author to whom correspondence should be addressed.
Received: 1 October 2013 / Revised: 8 November 2013 / Accepted: 12 November 2013 / Published: 20 November 2013
(This article belongs to the Special Issue Supramolecular Cage Complexes)
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Abstract

The neutral dinuclear complexes [(η5-C5Me5)2Rh2(μ-dhnq)Cl2] (1) and [(η5-C5Me5)2Ir2(μ-dhnq)Cl2] (2) (dhnqH2 = 5,8-dihydroxy-1,4-naphthoquinone) were obtained from the reaction of [(η5-C5Me5)M(μ-Cl)Cl]2 (M = Rh, Ir) with dhnqH2 in the presence of CH3COONa. Treatment of 1 or 2 in methanol with linear ditopic ligands L (L = pyrazine, 4,4′-bipyridine or 1,2-bis(4-pyridyl)ethylene), in the presence of AgCF3SO3, affords the corresponding tetranuclear metalla-rectangles [(η5-C5Me5)4M4(μ-dhnq)2(μ-L)2]4+ (L = pyrazine, M = Rh, 3; M = Ir, 4; L = 4,4′-bipyridine, M = Rh, 5; M = Ir, 6; L = 1,2-bis(4-pyridyl)ethylene, M = Rh, 7; M = Ir, 8). All complexes were isolated as their triflate salts and were fully characterized by infrared, 1H and 13C NMR spectroscopy, and some representative complexes by single-crystal X-ray structure analysis. The X-ray structures of 3, 5 and 6 confirm the formation of the tetranuclear metalla-cycles, and suggest that complexes 5 and 6 possess a cavity of sufficient size to encapsulate small guest molecules. In addition, the antiproliferative activity of the metalla-cycles 38 was evaluated against the human ovarian A2780 (cisplatin sensitive) and A2780cisR (cisplatin resistant) cancer cell lines and on non-tumorigenic human embryonic kidney HEK293 cells. All cationic tetranuclear metalla-rectangles were found to be highly cytotoxic, with IC50 values in the low micromolar range.
Keywords: metalla-cycles; half-sandwich complexes; bioorganometallic chemistry; metal-based drugs; metalla-rectangles; anticancer activity metalla-cycles; half-sandwich complexes; bioorganometallic chemistry; metal-based drugs; metalla-rectangles; anticancer activity
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Gupta, G.; Murray, B.S.; Dyson, P.J.; Therrien, B. Synthesis, Molecular Structure and Cytotoxicity of Molecular Materials Based on Water Soluble Half-Sandwich Rh(III) and Ir(III) Tetranuclear Metalla-Cycles. Materials 2013, 6, 5352-5366.

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