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Structure-activity relationships for cytotoxic ruthenium(II) arene complexes containing N,N-, N,O-, and O,O-chelating ligands

Habtemariam, Abraha and Melchart, Michael and Fernandez, Rafael and Parsons, Simon and Oswald, Iain D. H. and Parkin, Andrew and Fabbiani, Francesca P. A. and Davidson, James E. and Dawson, Alice and Aird, Rhona E. and Jodrell, Duncan I. and Sadler, Peter J. (2006) Structure-activity relationships for cytotoxic ruthenium(II) arene complexes containing N,N-, N,O-, and O,O-chelating ligands. Journal of Medicinal Chemistry, 49 (23). pp. 6858-6868. ISSN 0022-2623

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Abstract

We report structure-activity relationships for organometallic Ru-II complexes of the type [( eta(6)-arene) Ru-( XY) Cl] Z, where XY is an N, N-( diamine), N, O-( e. g., amino acidate), or O,O- ( e. g., beta-diketonate) chelating ligand, the arene ranges from benzene derivatives to fused polycyclic hydrocarbons, and Z is usually PF6. The X-ray structures of 13 complexes are reported. All have the characteristic "piano-stool" geometry. The complexes most active toward A2780 human ovarian cancer cells contained XY) ethylenediamine ( en) and extended polycyclic arenes. Complexes with polar substituents on the arene or XY) bipyridyl derivatives exhibited reduced activity. The activity of the O, O- chelated complexes depended strongly on the substituents and on the arene. For arene) p-cymene, XY) amino acidate complexes were inactive. Complexes were not cross-resistant with cisplatin, and cross-resistance to Adriamycin was circumvented by replacing XY) en with 1,2-phenylenediamine. Some complexes were also active against colon, pancreatic, and lung cancer cells.