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Issue 11, 2013
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Highly cytotoxic diruthenium trithiolato complexes of the type [(η6-p-MeC6H4Pri)2Ru22-SR)3]+: synthesis, characterization, molecular structure and in vitro anticancer activity

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Abstract

A new series of cationic dinuclear p-cymene ruthenium complexes bridged by three thiophenolato ligands containing various substituents mainly in meta and ortho positions, [(η6-p-MeC6H4Pri)2Ru22-SR)3]+ (R = 3-C6H4Me: 1; R = 3-C6H4OMe: 2; R = 3-C6H4OEt: 3; R = 3-C6H4CF3: 4; R = 3-C6H4NH2: 5; R = 3-C6H4Cl: 6; R = 2-C6H4Me: 7; R = 2-C6H4OMe: 8; R = 2-C6H4Pri: 9; R = 2-C6H4CF3: 10; R = npt: 11 (npt = 2-naphthyl); R = mco: 12 (mco = 4-methylcoumarinyl); R = 3,5-C6H3Me2: 13; R = 3,5-C6H3(CF3)2: 14; R = 3,5-C6H3Cl2: 15; R = 3,4-C6H3(OMe)2: 16), have been prepared from the reaction of the neutral p-cymene diruthenium dichloride dimer, [(η6-p-MeC6H4Pri)2Ru2Cl4], with the corresponding thiophenol RSH. All cationic complexes have been isolated as their chloride salts and fully characterized by spectroscopic and analytical methods. The molecular structures of 10 and 15 have been solved by a single-crystal X-ray structure analysis of [10]Cl and [15]Cl, which show that the two ruthenium atoms adopt a pseudo-octahedral geometry without a metal–metal bond in accordance with the noble gas rule. All complexes are highly cytotoxic towards human ovarian cancer cells, the IC50 values being mostly in the nanomolar range. Complex 9 shows the highest cytotoxicity with an IC50 value of 0.03 μM towards the A2780 cell line and the cisplatin-resistant mutant A2780cisR. The cytotoxicity of these complexes, which belong to the most active ruthenium anticancer compounds reported so far, can be correlated with the lipophilicity of the corresponding thiols. In comparison with the previous series, the results demonstrate that the positions of the substituents in the thiopenolato bridges are not as important as the nature of the substituents, alkyl substituents being the best ones in line with their lipophilic character.

Graphical abstract: Highly cytotoxic diruthenium trithiolato complexes of the type [(η6-p-MeC6H4Pri)2Ru2(μ2-SR)3]+: synthesis, characterization, molecular structure and in vitro anticancer activity

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Supplementary files

Article information


Submitted
06 May 2013
Accepted
08 Jul 2013
First published
09 Jul 2013

New J. Chem., 2013,37, 3503-3511
Article type
Paper

Highly cytotoxic diruthenium trithiolato complexes of the type [(η6-p-MeC6H4Pri)2Ru22-SR)3]+: synthesis, characterization, molecular structure and in vitro anticancer activity

F. Giannini, L. E. H. Paul, J. Furrer, B. Therrien and G. Süss-Fink, New J. Chem., 2013, 37, 3503
DOI: 10.1039/C3NJ00476G

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