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

Biometals. 2015 Jun;28(3):553-66. doi: 10.1007/s10534-015-9831-2. Epub 2015 Feb 25.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Coordination Complexes / chemical synthesis*
  • Coordination Complexes / chemistry*
  • Copper / chemistry*
  • Coumarins / chemistry*
  • Humans
  • Hydrazines / chemistry*
  • MCF-7 Cells
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Rhenium / chemistry*
  • Zinc / chemistry*

Substances

  • Coordination Complexes
  • Coumarins
  • Hydrazines
  • 3-acetylcoumarin
  • Rhenium
  • Copper
  • Zinc