Synthesis, Characterisation and Biological Activity of Novel Carboxylate Complexes Incorporating Phenanthroline and Benzimidazole Ligands
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This thesis reports results in two related areas: (1) the synthesis, characterisation and biological activity of soluble metal carboxylate complexes incorporating 1,10-phenanthroline and related ligands and (ii) the synthesis, characterisation and biological activity of Copper(II) complexes containing benzimidazole type ligands. 2,2-dimethylpentanedioic acid (2-dmepdaH2) and 3,3-dimethylpentanedioic acid (3-dmepdaHs) were reacted with copper (II) acetate to yield the novel soluble complexes [Cu(2-dmepda)(H2O)3]2 (1) and [Cu(3-dmepda)(H2)]3]2(2). Reaction of (1) and (2) with either 1,10-phenanthroline or 2,2’-bipyridine generated a series of novel soluble dicarboxylate complexes. The X-ray crystal structure of [Cu(2-dmepda)(bipy)(EtOH)]2-2EtOH and [Cu(3-dmepda)(bipy)(h2o)]2 were determined. The anti-Candida activity of all the soluble 2-dmpeda and 3-dmpeda complexes were determined. Significantly only the two non-phenanthroline complexes [Cu(2-dmepd)]H2O)3]2, [Cu(3-dmepda)(H2O),]2 and [Cu92-dmepda](phen)(H2O)]2.0.5phen(3) exhibited fungitoxic activity. A range of novel metal acetate (metal=Cu(II, Mn(II) and Zn(II) complexes incorporating the chelating 1,10-phenanthroline and the non-chelating 1,7-and 4,7-phenanthroline ligands were synthesised and characterised. The anti-Candida activity of these complexes was studies. Whereas the 1,10-phenanthroline complexes possessed good to moderate anti-fungal activity the complexes containing the non-chelating phenanthroline ligands were essentially inactive. 21 novel Copper(II) complexes were synthesised using simple Benzimidazole and Benzimidazole carboxylic acid ligands. These compounds were characterised using spectroscopic and physical methods. The X-ray crystal structure of [Cu(BZDtac)(1,10-phen)2]BZDtac.5H2)(BZDtacH=Benzimidazolylthioacetic acid were determined. The chloride,nitrate and sulphate salts of copper(II) were reacted with the chelating ligand Thiabendazole (TBZH) to yield salt like compounds. The reaction with copper (11) acetate yielded the previously unknown [Cu(TBZ)2(H2O)2]n. The X-ray crystal structure of [Cu(TBZH)2C1]C1.H2O.EtOH was determined. 7 novel Copper(II) (a,w-dicarboxylate) complexes incorporating Thiabendazole wee generated and characterised. The anti-Candida activity of all of the benzimidazole and thiabendazole complexes was examined. Unlike 1,10-phenanthroline the ‘metal free’ benzimidazole and thiabendazole were inactive against the pathogen, however, a range of their copper complexes were found to exhibit very good anti-fungal activity. The chemotherapeutic potential of a number of the complexes generated during this study was examined against human derived cancer cell line. Sever of the copper(II) complexes were found to exhibit significant activity.
O'Shea, D. (2004). Synthesis, characterisation and biological activity of novel carboxylate complexes incorporating phenanthroline and benzimidazole ligands,/i>. Doctoral thesis. Technological University Dublin. doi:10.21427/D7SK6G
Successfully submitted for the award of Doctor of Philosophy (Ph.D.) to the Technological University Dublin in 2004.