Kurzwernhart, Andrea;
Mokesch, Stephan;
Klapproth, Erik;
Adib‐Ravazi, Mahsa S.;
Jakupec, Michael A.;
Hartinger, Christian G.;
Kandioller, Wolfgang;
Keppler, Bernhard K.
Flavonoid‐Based Organometallics with Different Metal Centers – Investigations of the Effects on Reactivity and Cytotoxicity
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Media type:
E-Article
Title:
Flavonoid‐Based Organometallics with Different Metal Centers – Investigations of the Effects on Reactivity and Cytotoxicity
Contributor:
Kurzwernhart, Andrea;
Mokesch, Stephan;
Klapproth, Erik;
Adib‐Ravazi, Mahsa S.;
Jakupec, Michael A.;
Hartinger, Christian G.;
Kandioller, Wolfgang;
Keppler, Bernhard K.
Published:
Wiley, 2016
Published in:
European Journal of Inorganic Chemistry, 2016 (2016) 2, Seite 240-246
Language:
English
DOI:
10.1002/ejic.201501020
ISSN:
1434-1948;
1099-0682
Origination:
Footnote:
Description:
<jats:title>Abstract</jats:title><jats:p>Flavonol‐derived Os<jats:sup>II</jats:sup>(cym) and Rh<jats:sup>III</jats:sup>‐Cp* complexes were synthesized and the impact of the metal center on aqueous stability, reactivity toward biomolecules, and cytotoxic activity was compared to Ru<jats:sup>II</jats:sup> analogs. The Rh<jats:sup>III</jats:sup> complexes were the most stable to ligand release in aqueous solution and showed the highest preference for ubiquitin binding. Investigations on the reactivity toward nucleoside triphosphates revealed the clear affinity of Rh<jats:sup>III</jats:sup> to 5′‐dATP, whereas Ru<jats:sup>II</jats:sup> and Os<jats:sup>II</jats:sup> prefer binding to 5′‐dGTP. Simultaneous incubation with amino acids and nucleoside triphosphates reveals the preference toward amino acids, indicating that binding to proteins might be a key step in the mechanism of action of this compound class. The complexes exhibit in vitro anticancer activities in the high n<jats:sc>M</jats:sc> to low μ<jats:sc>M</jats:sc> range, confirming the flavonol scaffold as a promising <jats:italic>O</jats:italic>,<jats:italic>O</jats:italic>‐chelating ligand system for the development of anticancer active organometallics.</jats:p>