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Whithin this field sixteen novel Co(III) ternary complexes with the general formula [Co\n(4N)(flav)](ClO4)2, where 4N = tris(2-aminoethyl)amine (tren) or tris(2-pyridylmethyl)amine (tpa) and flav =\ndeprotonated form of differently substituted flavonols have been synthesized, characterized, and their cytotoxicity\nassayed under both normoxic and hypoxic conditions. Molecular structures of two free flavonols and seven\ncomplexes are also reported. In all the complexes the bioligands exhibited the expected (O,O) coordination mode\nand the complexes showed a slightly distorted octahedral geometry. Cyclic voltammetric studies revealed that\nboth the substituents of the flavonoles and the type of 4N donor ligands had an impact on the reduction potential\nof the complex. The ones containing tren demonstrated significantly higher stability than the tpa analogues,\nmaking these former compounds promising candidates for the development of hypoxia-activated prodrug\ncomplexes. Tpa complexes showed higher activity against both selected human cancer cell lines (A549, A431)\nthan their free ligand flavonols, indicating that the anticancer activity of the bioligand can be enhanced upon\ncomplexation. 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