New insight into the structural, electrochemical and biological aspects of macroacyclic Cu(II) complexes derived from S-substituted dithiocarbazate schiff bases

Low ML 1 , Maigre L 2 , Tahir MI 3 , Tiekink ER 4 , Dorlet P 5 , Guillot R 6 Show all authors , Ravoof TB 3 , Rosli R 7 , Pagès JM 2 , Policar C 8 , Delsuc N 9 , Crouse KA 10

Affiliations 

  • 1 Department of Chemistry, Universiti Putra Malaysia, 43400, Serdang, Selangor, Malaysia; 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
  • 2 UMR-MD1, Aix-Marseille Université, IRBA, Faculté de Médecine, 27 boulevard Jean Moulin, 13385, Marseille, France
  • 3 Department of Chemistry, Universiti Putra Malaysia, 43400, Serdang, Selangor, Malaysia
  • 4 Research Centre for Crystalline Materials, Faculty of Science and Technology, Sunway University, No. 5 Jalan Universiti, 47500, Bandar Sunway, Selangor Darul Ehsan, Malaysia. Electronic address: edward.tiekink@gmail.com
  • 5 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
  • 6 Institut de Chimie Moléculaire et des Matériaux d'Orsay, Bât. 420 Université Paris-Sud, 91405, Orsay, France
  • 7 Department of Obstetrics and Gynaecology, Universiti Putra Malaysia, 43400, Serdang, Selangor, Malaysia; UPM-MAKNA Cancer Research Laboratory, Institute of Bioscience, Universiti Putra Malaysia, 43400, Serdang, Selangor, Malaysia
  • 8 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. Electronic address: clotilde.policar@ens.fr
  • 9 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. Electronic address: nicolas.delsuc@upmc.fr
  • 10 Department of Chemistry, Universiti Putra Malaysia, 43400, Serdang, Selangor, Malaysia; Department of Chemistry, Cape Breton University, Sydney, Nova Scotia, B1P 6L2, Canada. Electronic address: kacrouse@gmail.com
Eur J Med Chem, 2016 Sep 14;120:1-12.
PMID: 27183379 DOI: 10.1016/j.ejmech.2016.04.027

Abstract

Copper (II) complexes synthesized from the products of condensation of S-methyl- and S-benzyldithiocarbazate with 2,5-hexanedione (SMHDH2 and SBHDH2 respectively) have been characterized using various physicochemical (elemental analysis, molar conductivity, magnetic susceptibility) and spectroscopic (infrared, electronic) methods. The structures of SMHDH2, its copper (II) complex, CuSMHD, and the related CuSBHD complex as well as a pyrrole byproduct, SBPY, have been determined by single crystal X-ray diffraction. In order to provide more insight into the behaviour of the complexes in solution, electron paramagnetic resonance (EPR) and electrochemical experiments were performed. Antibacterial activity and cytotoxicity were evaluated. The compounds, dissolved in 0.5% and 5% DMSO, showed a wide range of antibacterial activity against 10 strains of Gram-positive and Gram-negative bacteria. Investigations of the effects of efflux pumps and membrane penetration on antibacterial activity are reported herein. Antiproliferation activity was observed to be enhanced by complexation with copper. Preliminary screening showed Cu complexes are strongly active against human breast adenocarcinoma cancer cell lines MDA-MB-231 and MCF-7.

* Title and MeSH Headings from MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine.

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