, Volume 28, Issue 3, pp 553–566 | Cite as

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

  • May Lee Low
  • Georgiana Paulus
  • Pierre Dorlet
  • Régis Guillot
  • Rozita Rosli
  • Nicolas Delsuc
  • Karen A. Crouse
  • Clotilde Policar


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.

Graphical Abstract


3-Acetylcoumarin S-Benzyldithiocarbazate Copper(II) Zinc(II) Rhenium(I) 







Chemical ionization


Cyclic voltammetry


Dulbecco’s modified Eagle’s medium




Dimethyl sulfoxide


Deuterated dimethyl sulfoxide


Estrogen receptor


Electron paramagnetic resonance


Electrospray ionization–mass spectra


Fast atom bombardment


Fourier transform-infrared spectroscopy


Gas chromatography–mass spectral


High resolution-mass spectra


Human breast carcinoma cells expressing nuclear estrogen receptors


Human breast carcinoma cells not expressing nuclear estrogen receptors


Mass spectroscopy


3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide


Nuclear magnetic resonance


Oak ridge thermal ellipsoid plot


Phosphate buffered saline




Reversed phase-high performance liquid chromatography


N′-[1-(2-Oxo-2H-chromen-3-yl)-ethylidene]-hydrazinecarbodithioic acid benzyl ester

% T

Percentage of transmission


Trifluoroacetic acid




X-ray diffractometry



Support for the Project came from Universiti Putra Malaysia (UPM), the Ministry of Higher Education (Malaysia), French ANR Blanc 2010, METABACT Grant and the French Infrastructure for Integrated Structural Biology (FRISBI) ANR-10-INSB-05-01. M. L. Low is grateful for the award of an Erasmus Mundus: Maheva Scholarship and a UPM Graduate Research Fellowship (GRF).

Supplementary material

10534_2015_9831_MOESM1_ESM.doc (1.7 mb)
Supplementary material 1 (DOC 1734 kb)


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Copyright information

© Springer Science+Business Media New York 2015

Authors and Affiliations

  • May Lee Low
    • 1
    • 2
  • Georgiana Paulus
    • 2
  • Pierre Dorlet
    • 3
  • Régis Guillot
    • 4
  • Rozita Rosli
    • 5
    • 6
  • Nicolas Delsuc
    • 1
  • Karen A. Crouse
    • 2
    • 7
  • Clotilde Policar
    • 1
  1. 1.École Normale Supérieure-PSL Research University, Département de Chimie, Sorbonne Universités - UPMC, Univ Paris 06, CNRS UMR 7203 LBMParisFrance
  2. 2.Department of ChemistryUniversiti Putra MalaysiaSerdangMalaysia
  3. 3.Laboratoire Stress Oxydant et Détoxication, Institute for Integrative Biology of the Cell (I2BC), Université Paris-Saclay, CEA, CNRS, Université Paris-SudGif sur Yvette CedexFrance
  4. 4.Institut de Chimie Moléculaire et des Matériaux d’OrsayUniversité Paris-SudOrsayFrance
  5. 5.UPM-MAKNA Cancer Research Laboratory, Institute of BioscienceUniversiti Putra MalaysiaSerdangMalaysia
  6. 6.Department of Obstetrics and Gynaecology, Faculty of Medicine and Health SciencesUniversiti Putra MalaysiaSerdangMalaysia
  7. 7.Department of ChemistryCape Breton UniversitySydneyCanada

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