Unexpected influence of stereochemistry on the cytotoxicity of highly efficient Ti IV salan complexes: New mechanistic insights

Cesar M. Manna, Gad Armony, Edit Y. Tshuva*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

37 Scopus citations

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.

Original languageEnglish
Pages (from-to)14094-14103
Number of pages10
JournalChemistry - A European Journal
Volume17
Issue number50
DOIs
StatePublished - 9 Dec 2011

Keywords

  • chiral induction
  • cytotoxicity
  • phenolato ligands
  • salan
  • titanium

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