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Title: Ruthenium arene anti-cancer complexes
Author: Bugarcic, Tijana
Awarding Body: University of Edinburgh
Current Institution: University of Edinburgh
Date of Award: 2008
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This thesis is concerned with the synthesis and characterization of novel RuII arene anti-cancer complexes, containing different arenes and chelating ligands, especially arenes that can act as intercalators and chelating ligands that are redox-active. Synthesis and characterization of complexes of the type [(H6-arene)Ru(en)Cl]+, where the arene is ortho-, meta- or para-terphenyl (o-, m- or p-terp) are reported. [(H6-p-terp)Ru(en)Cl]+ has a similar potency to cisplatin and much higher activity against cancer cell lines than o- and m-terp analogues. The p-terp complex binds to DNA rapidly and quantitatively and the experimental data are consistent with combined intercalative and monofunctional (coordination) binding mode of [(H6-p-terp)Ru(en)Cl]+. The o- and m-terp analogues bind to DNA preferentially through coordination of ruthenium. The synthesis and characterization of RuII arene complexes containing 2,2’-bipyridine (bipy), 2,2’-bipyridine-3,3’-diol (bipy(OH)2) or deprotonated 2,2’-bipyridine-3,3’-diol (bipy(OH)O) as chelating ligands and different arenes are reported, including several x-ray crystal structures. In aqueous solution only the deprotonated (bipy(OH)O) form of the 2,2’-bipyridine-3,3’-diol is present in the complexes. Hydrolysis of these complexes in aqueous solution is relatively fast (37°C) and when the arene is biphenyl, initial aquation is followed by partial arene loss. Complexes with bipy(OH)O as chelating ligands, in general exhibit good cytotoxicity towards A2780 human ovarian cancer cells. Oxidation of the o-phenylenediamine (o-pda) chelating ligand in [(H6-arene)Ru(o-pda)Cl]+ to o-benzoquinonediimine (o-bqdi) leads to loss of cytotoxic activity. The x-ray crystal structures of [(H6-p-cym)Ru(o-pda)Cl][PF6] and [(H6-hmb)Ru(o-bqdi)Cl][PF6] are reported.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available