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Selective, Cytotoxic Organoruthenium(II) Full‐Sandwich Complexes: A Structural, Computational and In Vitro Biological Study
Author(s) -
Loughrey Bradley T.,
Cunning Benjamin V.,
Healy Peter C.,
Brown Christopher L.,
Parsons Peter G.,
Williams Michael L.
Publication year - 2012
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201100637
Subject(s) - chemistry , cyclopentadienyl complex , ruthenium , cationic polymerization , stereochemistry , moiety , delocalized electron , nuclear magnetic resonance spectroscopy , electrospray ionization , cytotoxicity , mass spectrometry , crystallography , in vitro , organic chemistry , biochemistry , chromatography , catalysis
A structurally diverse range of lipophilic, cationic η 6 ‐arene η 5 ‐cyclopentadienyl (η 5 ‐Cp*) full‐sandwich complexes of ruthenium(II) have been prepared and structurally characterized by Fourier‐transform IR and NMR spectroscopy, electrospray mass spectrometry, and elemental microanalyses. Computational experiments incorporating the Hartree–Fock theory and the second‐order Møller–Plesset perturbation theory predict each complex to possess a uniform δ+ electrostatic potential, with the cationic charge of the [RuCp*] + moiety completely delocalizing throughout the molecular structure of each metallocene. In vitro cytotoxicity studies demonstrate these delocalized lipophilic cations to be potent growth inhibitors of eleven unique tumorigenic cell lines, while exhibiting significantly lower levels of toxicity towards both a normal human fibroblast and a mouse macrophage cell line. Single‐crystal X‐ray structural determinations are additionally reported for five complexes, [Ru(η 6 ‐C 6 H 5 (CH 2 ) 2 CH 3 )(η 5 ‐C 5 (CH 3 ) 5 )]BPh 4 , [Ru(η 6 ‐C 6 H 5 CO 2 CH 2 CH 3 )(η 5 ‐C 5 (CH 3 ) 5 )]BF 4 , [Ru(η 6 ‐C 10 H 8 )(η 5 ‐C 5 (CH 3 ) 5 )]BPh 4 , [Ru(η 6 ‐C 14 H 10 )(η 5 ‐C 5 (CH 3 ) 5 )]BPh 4 , and [Ru(η 6 ‐C 16 H 10 )(η 5 ‐C 5 (CH 3 ) 5 )]BPh 4 .