| 17397929 |
Devereux M, O Shea D, Kellett A, McCann M, Walsh M, Egan D, Deegan C, Kedziora K, Rosair G, Muller-Bunz H: Synthesis, X-ray crystal structures and biomimetic and anticancer activities of novel copper (II) benzoate complexes incorporating 2-(4'-thiazolyl) benzimidazole (thiabendazole), 2-(2-pyridyl) benzimidazole and 1,10-phenanthroline as chelating nitrogen donor ligands. J Inorg Biochem. 2007 Jun;101(6):881-92. Epub 2007 Feb 14.
Cu (BZA)(2)(EtOH)(0.5) (1) was generated by the reaction of copper (II) hydroxide with benzoic acid (BZAH). [Cu (TBZH)(2)(BZA)](BZA).0.5TBZH.H (2) O (2) and [Cu (2-PyBZIMH)(2-PyBZIM)(BZA)].1.66EtOH (3) were obtained when 1 reacted with Thiabendazole (TBZH) and 2-(2-pyridyl) benzimidazole (2-PyBZIMH), respectively. [Cu (BZA)(2)(phen)(H (2) O)] (4) was isolated from the reaction of benzoic acid and 1,10-phenanthroline (phen) with copper (II) acetate dihydrate. Molecular structures of 2, 3 and 4 were determined crystallographically. 2 and 3 are hydrogen bonded dimers and trimers, respectively. The copper centres in complexes 2 and 3 are bis-chelate derivatives that have N (4) O ligation and their geometry is very similar being approximately square-pyramidal. However whereas in complex 2 both TBZH ligands are neutral in 3 one of the 2-PyBZIMH chelators is deprotonated on each copper. The structural results for 4 represent a re-examination of this crystallographically known compound for which no hydrogen atom coordinates have been previously reported. It crystallises as a hydrogen bonded dimmer and is a mono-chelate of phen with each copper centre possessing N (2) O (3) ligation and square pyramidal geometry. The catalase and superoxide dismutase (SOD) activities of the four complexes along with those of the known phenanthroline complexes [Cu (mal)(phen)(2)] and [Cu (phendione)(3)](ClO (4))(2) (malH (2)=malonic acid and phendione=1,10-phenanthroline-5,6-dione) were investigated. Complexes 1-4, the metal free ligands and a simple copper (II) salt were assessed for their cancer chemotherapeutic potential against the hepatocellular carcinoma (Hep-G (2)) and kidney adenocarcinoma (A-498) cell lines. TBZH, 2-PyBZIMH and benzoic acid when uncoordinated to a metal centre offer poor chemotherapeutic potential. copper (II) benzoate is significantly more active than the free acid. The bis-chelate derivatives [Cu (TBZH)(2)(BZA)](BZA).0.5TBZH.H (2) O (2) and [Cu (2-PyBZIMH)(2-PyBZIM)(BZA)].1.66EtOH (3) elicit a significant cytotoxic response to the cancer cell lines tested. Replacing TBZH and 2-PyBZIMH with phen to give [Cu (BZA)(2)(phen)(H (2) O)] (4) does not significantly increase the anti-cancer activity. |
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