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Maltol‐Derived Ruthenium–Cymene Complexes with Tumor Inhibiting Properties: The Impact of Ligand–Metal Bond Stability on Anticancer Activity In Vitro
Author(s) -
Kandioller Wolfgang,
Hartinger Christian G.,
Nazarov Alexey A.,
Bartel Caroline,
Skocic Matthias,
Jakupec Michael A.,
Arion Vladimir B.,
Keppler Bernhard K.
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200901939
Subject(s) - chemistry , aquation , maltol , ruthenium , ligand (biochemistry) , reactivity (psychology) , stereochemistry , dimer , in vitro , medicinal chemistry , kinetics , receptor , biochemistry , organic chemistry , reaction rate constant , catalysis , medicine , physics , alternative medicine , pathology , quantum mechanics
Organometallic ruthenium–arene compounds bearing a maltol ligand have been shown to be nearly inactive in in vitro anticancer assays, presumably due to the formation of dimeric Ru II species in aqueous solutions. In an attempt to stabilize such complexes, [Ru(η 6 ‐ p ‐cymene)(XY)Cl] (XY=pyrones or thiopyrones) complexes with different substitution pattern of the (thio)pyrone ligands have been synthesized, their structures characterized spectroscopically, and their aquation behavior investigated as well as their tumor‐inhibiting potency. The aquation behavior of pyrone systems with electron‐donating substituents and of thiopyrone complexes was found to be significantly different from that of the maltol‐type complex reported previously. However, the formation of the dimer can be excluded as the primary reason for the inactivity of the complex because some of the stable compounds are not active in cancer cell lines either. In contrast, studies of their reactivity towards amino acids demonstrate different reactivities of the pyrone and thiopyrone complexes, and the higher stability of the latter probably renders them active against human tumor cells.