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Contents Vol 63(11)

Influence of the Arene Ligand and the Leaving Group on the Anticancer Activity of (Thio)maltol Ruthenium(ii)–(η6-Arene) Complexes

Muhammad Hanif A , Patricia Schaaf A , Wolfgang Kandioller A , Michaela Hejl A , Michael A. Jakupec A B , Alexander Roller A , Bernhard K. Keppler A B and Christian G. Hartinger A B C
+ Author Affiliations
- Author Affiliations

A University of Vienna, Institute of Inorganic Chemistry, Waehringer Straße 42, A-1090 Vienna, Austria.

B University of Vienna, Research Platform ‘Translational Cancer Therapy Research’, Waehringer Straße 42, A-1090 Vienna, Austria.

C Corresponding author. Email: christian.hartinger@univie.ac.at

Australian Journal of Chemistry 63(11) 1521-1528 https://doi.org/10.1071/CH10232
Submitted: 7 June 2010  Accepted: 22 September 2010   Published: 11 November 2010

Abstract

Maltol and its metal complexes have shown promising applications in medicinal chemistry. We report here the synthesis and characterization of Ru(η6-arene)(halido) coordination compounds bearing maltol or thiomaltol ligands and studies on their behaviour in aqueous solution, their reactions with the DNA model guanosine 5′-monophosphate (5′-GMP) and their in vitro anticancer activity in human tumour cell lines. The compounds hydrolyze rapidly and quantitatively to the respective aqua species by exchange of the halido ligand. With pKa values of >8, such species would also be present in biological media and they proved reactive to 5′-GMP. The thiomaltol compounds show promising in vitro activity with IC50 values (50% inhibitory concentration) in the low micromolar range, whereas activity of the maltol complexes is marginal. Variation of the arene ligand (benzene, toluene, p-cymene or biphenyl) resulted only in minor changes in activity.


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