Effect of glucosamine conjugation to zinc(II) complexes of a bis-pyrazole ligand: Syntheses, characterization and anticancer activity.

Effect of glucosamine conjugation to zinc(II) complexes of a bis-pyrazole ligand: Syntheses, characterization and anticancer activity. J Inorg Biochem. 2014 Jul 22;140C:131-142 Authors: Bhattacharyya S, Sarkar A, Dey SK, Mukherjee A Abstract The bis(3,5-dimethyl-1H- pyrazol-1yl)acetic acid (bdmpza) ligand was conjugated with tert-butyl-N-(2-aminoethyl) carbonate, methyl-2-amino-4-(methylthio)butanoate and 1,3,4,6-tetra-O-acetyl-β-d-glucosamine hydrochloride via amide coupling method to form three ligands L1-L3 which were then reacted with Zn(II) salts to form four zinc complexes (1-4). The complexes were characterized by (1)H NMR, (13)C NMR, electrospray ionization mass spectrometry (ESI-MS), FT-IR, CHN analyses. Complexes 1, 2 and 4 were also characterized by single crystal X-ray diffraction. It was found that Zn(II) salts could selectively remove the acetyl group from anomeric position leaving everything else intact. The cytotoxicity studies of the ligand and the complexes showed that the conjugation to acetylated glucosamine enhances cytotoxic ability although the complexes become more hydrophilic. Cytotoxicity studies in human breast adenocarcinoma (MCF-7), human cervical cancer (HeLa WT) and human lung adenocarcinoma (A549) showed that the acetylated glucosamine conjugation to the bis-pyrazole ligated Zn(II) complex led to 2-4 fold increase in cytotoxicity (IC50 values ca. 57-80μM) against HeLa WT and MCF-7 cell lines. The Zn(...
Source: Journal of Inorganic Biochemistry - Category: Biochemistry Authors: Tags: J Inorg Biochem Source Type: research