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Flavonoid‐Based Organometallics with Different Metal Centers – Investigations of the Effects on Reactivity and Cytotoxicity
Author(s) -
Kurzwernhart Andrea,
Mokesch Stephan,
Klapproth Erik,
AdibRavazi Mahsa S.,
Jakupec Michael A.,
Hartinger Christian G.,
Kandioller Wolfgang,
Keppler Bernhard K.
Publication year - 2016
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201501020
Subject(s) - chemistry , cytotoxicity , reactivity (psychology) , flavonoid , metal , organic chemistry , combinatorial chemistry , biochemistry , in vitro , antioxidant , medicine , alternative medicine , pathology
Flavonol‐derived Os II (cym) and Rh III ‐Cp* complexes were synthesized and the impact of the metal center on aqueous stability, reactivity toward biomolecules, and cytotoxic activity was compared to Ru II analogs. The Rh III 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 III to 5′‐dATP, whereas Ru II and Os II 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 M to low μ M range, confirming the flavonol scaffold as a promising O , O ‐chelating ligand system for the development of anticancer active organometallics.