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Can Substitution of Chlorides Enhance the Cytotoxicity of Vanadocene Dichloride?
Author(s) -
Vinklárek Jaromír,
Hurychová Hana,
Honzíček Jan,
Šebestová Lucie,
Padělková Zdeňka,
Řezáčová Martina
Publication year - 2013
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.201201505
Subject(s) - chemistry , trifluoromethanesulfonate , cytotoxicity , chelation , ligand (biochemistry) , medicinal chemistry , aqueous solution , electron paramagnetic resonance , chloride , stereochemistry , in vitro , inorganic chemistry , organic chemistry , catalysis , receptor , biochemistry , physics , nuclear magnetic resonance
A series of vanadocene complexes [Cp′ 2 V( L )][OTf] 2 (Cp′ = η 5 ‐C 5 H 5 , η 5 ‐C 5 H 4 Me; L = phen, 5‐NO 2 ‐phen, 5‐NH 2 ‐phen, 4,7‐Ph 2 ‐phen) was prepared and characterized by mass spectrometry and EPR spectroscopy. Structures of two complexes that contain an N , N′ ‐chelating ligand, [(η 5 ‐C 5 H 4 Me) 2 V(phen)][OTf] 2 · 0.5Me 2 CO and [(η 5 ‐C 5 H 5 ) 2 V(5‐NH 2 ‐phen)][OTf] 2 , and the triflate intermediate [(η 5 ‐C 5 H 5 ) 2 V(OTf) 2 ] were further confirmed by X‐ray diffraction analysis. The cytotoxicity study has shown that complexes that contain phenanthroline ligands have considerably higher in vitro activity toward human leukemia cells MOLT‐4 and HL‐60 than their parent dichlorides ([Cp′ 2 VCl 2 ]). The high activity of these complexes coheres with their higher stability in various aqueous media. This study has further shown that substitution of chloride ligands in the vanadocene dichloride has a considerably higher effect on cytotoxicity than expected on the basis of established mechanistic rules.