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Unexpected influence of stereochemistry on the cytotoxicity of highly efficient Ti(IV) salan complexes: new mechanistic insights. | LitMetric

AI Article Synopsis

  • The study investigates how the stereochemistry of N-methylated Ti(IV) salan complexes affects their cytotoxicity, focusing on their hydrolytic stability.
  • Researchers synthesized various bis(isopropoxo) complexes with chiral and racemic forms, finding that racemic mixtures showed greater cytotoxicity than their enantiomers.
  • Further experiments with achiral and chiral sec-butoxo ligands indicated that stereochemistry had minimal impact on cytotoxicity, suggesting fast dissociation of labile ligands in creating polynuclear compounds.

Article Abstract

The effect of stereochemistry on the cytotoxicity of highly active and hydrolytically stable N-methylated Ti(IV) salan complexes is reported. Four bis(isopropoxo) complexes incorporating N-methylated salan ligands with different aromatic substitution patterns have been prepared in racemic and optically active forms for the first time by ligand-to-metal chiral induction from trans-diaminocyclohexyl-based chiral ligands. The configuration of the metal center that derives from that of the ligand has an enormous influence on cytotoxicity, with the racemic mixture mostly being more active than the single enantiomers that are of either similar or different activity. This implies that the active species is a salan-bound heterochiral polynuclear compound, interacting with a chiral target. Four additional complexes of achiral salan and chiral labile sec-butoxo ligands, analyzed as racemic and as homochiral, revealed no influence of stereochemistry, supporting early dissociation of the labile ligands to give the polynuclear products.

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Source
http://dx.doi.org/10.1002/chem.201102017DOI Listing

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