Issue 3, 2008
From the journal:

New Journal of Chemistry

A cytotoxic bis(carbene)gold(i) complex of ferrocenyl complexes: synthesis and structural characterisation†

Ulrike E. I. Horvath,*a   Gino Bentivoglio,b   Michael Hummel,b   Herwig Schottenberger,b   Klaus Wurst,b   Margo J. Nell,c   Constance E. J. van Rensburg,c   Stephanie Cronjea  and  Helgard G. Raubenheimer*a  

* Corresponding authors

a Department of Chemistry and Polymer Science, University of Stellenbosch, Private Bag X1, Matieland, South Africa
E-mail: hgr@sun.ac.za, uhorvath@gmail.com
Fax: +27 21 808 3849
Tel: +27 21 808 3850

b Institut für Allgemeine, Anorganische und Theoretische Chemie, Leopold Franzens Universität, Innrain 52a, Innsbruck, Austria

c Department of Pharmacology, Faculty of Medicine, University of Pretoria, P.O. Box 2034, Pretoria, South Africa

Abstract

The N-heterocyclic carbene (NHC) precursors 1-[(E)-2-butenyl]-3-(4-ferrocenylphenyl)imidazolium bromide (2) and 1-[(E)-2-butenyl]-3-(4-ferrocenylphenyl)imidazolium tetrafluoroborate (3) were derived from 1-(4-ferrocenylphenyl)imidazole. Ferrocenyl complex 3 reacts with Ag2O and chloro(dimethylsulfide)gold(I) in the presence of tetraethylammonium chloride to produce the mixed metal species bis{1-[(E)-2-butenyl]-3-(4-ferrocenylphenyl)-2H-imidazol-2-ylidene}gold(I) tetrafluoroborate (4). Single crystal X-ray structure analyses of 1, 3 and 4 indicate that the NCHN-hydrogen in 3 is hydrogen bonded to the BF4− anion [C(H1)⋯F, 3.265(4) Å], as is also reflected in the position of its 1H NMR chemical shift. Cytotoxicity studies show that complex 4 is selective for cancer cells and active against the tumour cell lines Jurkat and MCF 7.

Graphical abstract: A cytotoxic bis(carbene)gold(i) complex of ferrocenyl complexes: synthesis and structural characterisation

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Article information

DOI
https://doi.org/10.1039/B713917A
Article type
Paper
Submitted
11 Sep 2007
Accepted
19 Nov 2007
First published
12 Dec 2007

New J. Chem., 2008,32, 533-539

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A cytotoxic bis(carbene)gold(I) complex of ferrocenyl complexes: synthesis and structural characterisation

U. E. I. Horvath, G. Bentivoglio, M. Hummel, H. Schottenberger, K. Wurst, M. J. Nell, C. E. J. van Rensburg, S. Cronje and H. G. Raubenheimer, New J. Chem., 2008, 32, 533 DOI: 10.1039/B713917A

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