Synthesis, characterization and biological activity of Cu(II), Zn(II) and Re(I) complexes derived from S-benzyldithiocarbazate and 3-acetylcoumarin

• DOI: 10.1007/s10534-015-9831-2
• Publication Date: 2015-02-24T05:29:02Z
• Authors: May Lee Low; Georgiana Paulus; Pierre Dorlet; Régis Guillot; Rozita Rosli; Nicolas Delsuc; Karen A. Crouse; Clotilde Policar
• Keywords: Magnetic Resonance Spectroscopy; [CHIM.ORGA]Chemical Sciences/Organic chemistry; Cell Survival; [CHIM.ORGA] Chemical Sciences/Organic chemistry; 01 natural sciences; Mass Spectrometry; 0104 chemical sciences; 3. Good health; Zinc; Hydrazines; Rhenium; Coordination Complexes; Coumarins; Cell Line, Tumor; MCF-7 Cells; Humans; Copper

Cu(II), Zn(II) and Re(I) complexes have been synthesized with the Schiff base, N'-[1-(2-oxo-2H-chromen-3-yl)-ethylidene]-hydrazinecarbodithioic acid benzyl ester (SBCM-H) which was prepared by condensation of S-benzyldithiocarbazate and 3-acetylcoumarin. The metal complexes were characterized on the basis of various physico-chemical and spectroscopic techniques including elemental analysis and electrochemical studies, and FT-IR, UV-Vis, NMR, EPR and mass spectroscopy. The Schiff base was found to behave as a bidentate ligand coordinating with Cu(II) and Zn(II) in the thiolate form with 1:2 metal to ligand stoichiometry. Crystals suitable for X-ray diffractometry (XRD) were obtained from the reaction of ReCl(CO)5 with SBCM-H forming a centrosymmetric dimeric complex Re2L2(CO)6 linked by Re-S-Re bridges, where S is the thiolate sulfur of the N,S-bidentate ligand. This Re(I) complex is the first metal carbonyl complex with a bidentate dithiocarbazate ligand to have been characterized by XRD. Cytotoxicity assays revealed enhancement of the bioactivity of SBCM-H upon complexation. Both Cu(II) and Re(I) complexes are found to be active against human breast adenocarcinoma cancer cell lines MDA-MB-231 and MCF-7. TOC diagram.