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

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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.

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Scheme 1
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Abbreviations

Abs:

Absorbance

ACN:

Acetonitrile

CI:

Chemical ionization

CV:

Cyclic voltammetry

DMEM:

Dulbecco’s modified Eagle’s medium

DMF:

Dimethylformamide

DMSO:

Dimethyl sulfoxide

DMSO-d6 :

Deuterated dimethyl sulfoxide

ER:

Estrogen receptor

EPR:

Electron paramagnetic resonance

ESI–MS:

Electrospray ionization–mass spectra

FAB:

Fast atom bombardment

FT-IR:

Fourier transform-infrared spectroscopy

GC–MS:

Gas chromatography–mass spectral

HR-MS:

High resolution-mass spectra

MCF-7:

Human breast carcinoma cells expressing nuclear estrogen receptors

MDA-MB-231:

Human breast carcinoma cells not expressing nuclear estrogen receptors

MS:

Mass spectroscopy

MTT:

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

NMR:

Nuclear magnetic resonance

ORTEP:

Oak ridge thermal ellipsoid plot

PBS:

Phosphate buffered saline

Pyta:

4-(2-Pyridyl)-1,2,3-triazole

RP-HPLC:

Reversed phase-high performance liquid chromatography

SBCM-H:

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

% T:

Percentage of transmission

TFA:

Trifluoroacetic acid

UV–Vis:

Ultraviolet–Visible

XRD:

X-ray diffractometry

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Acknowledgments

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).

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Authors and Affiliations

  1. École Normale Supérieure-PSL Research University, Département de Chimie, Sorbonne Universités - UPMC, Univ Paris 06, CNRS UMR 7203 LBM, 24, rue Lhomond, 75005, Paris, France

    May Lee Low, Nicolas Delsuc & Clotilde Policar

  2. Department of Chemistry, Universiti Putra Malaysia, 43400, Serdang, Selangor, Malaysia

    May Lee Low, Georgiana Paulus & Karen A. Crouse

  3. Laboratoire Stress Oxydant et Détoxication, Institute for Integrative Biology of the Cell (I2BC), Université Paris-Saclay, CEA, CNRS, Université Paris-Sud, Bât 532 CEA Saclay, 91191, Gif sur Yvette Cedex, France

    Pierre Dorlet

  4. Institut de Chimie Moléculaire et des Matériaux d’Orsay, Université Paris-Sud, Bât. 420, 91405, Orsay, France

    Régis Guillot

  5. UPM-MAKNA Cancer Research Laboratory, Institute of Bioscience, Universiti Putra Malaysia, 43400, Serdang, Selangor, Malaysia

    Rozita Rosli

  6. Department of Obstetrics and Gynaecology, Faculty of Medicine and Health Sciences, Universiti Putra Malaysia, 43400, Serdang, Selangor, Malaysia

    Rozita Rosli

  7. Department of Chemistry, Cape Breton University, Sydney, NS, B1P 6L2, Canada

    Karen A. Crouse

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  1. May Lee Low
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  2. Georgiana Paulus
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Low, M.L., Paulus, G., Dorlet, P. et al. Synthesis, characterization and biological activity of Cu(II), Zn(II) and Re(I) complexes derived from S-benzyldithiocarbazate and 3-acetylcoumarin. Biometals 28, 553–566 (2015). https://doi.org/10.1007/s10534-015-9831-2

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  • DOI: https://doi.org/10.1007/s10534-015-9831-2

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