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Issue 17, 2013
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3-Hydroxyflavones vs. 3-hydroxyquinolinones: structure–activity relationships and stability studies on RuII(arene) anticancer complexes with biologically active ligands

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Abstract

RuII6-arene) complexes, especially with bioactive ligands, are considered to be very promising compounds for anticancer drug design. We have shown recently that RuII6-p-cymene) complexes with 3-hydroxyflavone ligands exhibit very high in vitro cytotoxic activities correlating with a strong inhibition of topoisomerase IIα. In order to expand our knowledge about the structure–activity relationships and to determine the impact of lipophilicity of the arene ligand and of the hydrolysis rate on anticancer activity, a series of novel 3-hydroxyflavone derived RuII6-arene) complexes were synthesised. Furthermore, the impact of the heteroatom in the bioactive ligand backbone was studied by comparing the cytotoxic activity of RuII6-p-cymene) complexes of 3-hydroxyquinolinone ligands with that of their 3-hydroxyflavone analogues. To better understand the behaviour of these RuII complexes in aqueous solution, the stability constants and pKa values for complexes and the corresponding ligands were determined. Furthermore, the interaction with the DNA model 5′-GMP and with a series of amino acids was studied in order to identify potential biological target structures.

Graphical abstract: 3-Hydroxyflavones vs. 3-hydroxyquinolinones: structure–activity relationships and stability studies on RuII(arene) anticancer complexes with biologically active ligands

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Publication details

The article was received on 21 Sep 2012, accepted on 01 Nov 2012 and first published on 06 Nov 2012


Article type: Paper
DOI: 10.1039/C2DT32206D
Citation: Dalton Trans., 2013,42, 6193-6202
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    3-Hydroxyflavones vs. 3-hydroxyquinolinones: structure–activity relationships and stability studies on RuII(arene) anticancer complexes with biologically active ligands

    A. Kurzwernhart, W. Kandioller, É. A. Enyedy, M. Novak, M. A. Jakupec, B. K. Keppler and C. G. Hartinger, Dalton Trans., 2013, 42, 6193
    DOI: 10.1039/C2DT32206D

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