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    Synthesis, antimicrobial activity and chemotherapeutic potential of inorganic derivatives of 2-(40-thiazolyl)benzimidazole{thiabendazole}: X-ray crystal structures of [Cu(TBZH)2Cl]Cl • H2O • EtOH and TBZH2NO3 (TBZH¼thiabendazole)


    Devereux, Michael and McCann, Malachy and O'Shea, Denis and Kelly, Rachel and Egan, Denise and Deegan, Carol and Kavanagh, Kevin and McKee, Vickie and Finn, Gregory J. (2004) Synthesis, antimicrobial activity and chemotherapeutic potential of inorganic derivatives of 2-(40-thiazolyl)benzimidazole{thiabendazole}: X-ray crystal structures of [Cu(TBZH)2Cl]Cl • H2O • EtOH and TBZH2NO3 (TBZH¼thiabendazole). Journal of Inorganic Biochemistry, 98 (6). pp. 1023-1031. ISSN 0162-0134

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    Abstract

    Thiabendazole (TBZH) reacts with iron(III) nitrate causing protonation of the ligand to yield the nitrate salt [TBZH2NO3] (1). Reaction of TBZH with copper(II) acetate results in the deprotonation of the ligand yielding [Cu(TBZ)2 • (H2O)2] (2). Reactions of TBZH with the chloride, nitrate and butanedioate salts of copper(II) yields [Cu(TBZH)2Cl]Cl • H2O • EtOH (3), [Cu(TBZH)2(NO3)2] (4) and [Cu(TBZH)(O2C–CH2CH2–CO2)] (5), respectively. The TBZH acts as a neutral chelating ligand in 3–5. Molecular structures of 1 and 3 were determined crystallographically. In 1, the asymmetric unit contains one TBZHþ 2 cation and one NO 3 anion. The structure of 3 comprises a five coordinate copper centre with the metal bound to two chelating TBZH ligands and one chloride. The geometry is best described as trigonal bipyramidal. Hydrogen bonding connects the complex cation with the uncoordinated chloride anion and the water and ethanol solvate molecules. Compound 1 and the copper complexes 2–5, the metal free ligands and a number of simple copper(II) salts were each tested for their ability to inhibit the growth of Candida albicans. The metal free TBZH and its nitrate salt (1) exhibited very poor activity. Complex 2, in which the TBZH is present as an anionic ligand (TBZ), exhibits moderate activity towards the pathogen. Chelation of the neutral TBZH to copper centres (complexes 3–5) results in potent anticandida activity. The dimethyl sulphoxide (DMSO) soluble complexes 3 and 4, along with metal free TBZH were assessed for their cancer chemotherapeutic potential towards two human epithelial-derived cancer model cell lines. Complexes 3 and 4 displayed similar dose-dependent cytotoxicity in both cell lines with IC50 values of approximately 50 lM, which were found to be significantly lower than that for metal free TBZH.

    Item Type: Article
    Keywords: : Anti-fungal; Candida; Chemotherapeutic potential; Metal complexes; Thiabendazole;
    Academic Unit: Faculty of Science and Engineering > Chemistry
    Item ID: 6998
    Identification Number: https://doi.org/10.1016/j.jinorgbio.2004.02.020
    Depositing User: Dr. Malachy McCann
    Date Deposited: 01 Mar 2016 15:37
    Journal or Publication Title: Journal of Inorganic Biochemistry
    Publisher: Elsevier
    Refereed: Yes
    URI:

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