title: New insight into the structural, electrochemical and biological aspects of macroacyclic Cu(II) complexes derived from S-substituted dithiocarbazate schiff bases.
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.
authors.affiliation: 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.
authors.forename: May Lee
authors.initials: ML
authors.lastname: Low
authors.affiliation: UMR-MD1, Aix-Marseille Université, IRBA, Faculté de Médecine, 27 boulevard Jean Moulin, 13385, Marseille, France.
authors.forename: Laure
authors.initials: L
authors.lastname: Maigre
authors.affiliation: Department of Chemistry, Universiti Putra Malaysia, 43400, Serdang, Selangor, Malaysia.
authors.forename: Mohamed Ibrahim M
authors.initials: MI
authors.lastname: Tahir
authors.affiliation: 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.
authors.forename: Edward R T
authors.initials: ER
authors.lastname: Tiekink
authors.affiliation: 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.
authors.forename: Pierre
authors.initials: P
authors.lastname: Dorlet
authors.affiliation: Institut de Chimie Moléculaire et des Matériaux d'Orsay, Bât. 420 Université Paris-Sud, 91405, Orsay, France.
authors.forename: Régis
authors.initials: R
authors.lastname: Guillot
authors.affiliation: Department of Chemistry, Universiti Putra Malaysia, 43400, Serdang, Selangor, Malaysia.
authors.forename: Thahira Begum
authors.initials: TB
authors.lastname: Ravoof
authors.affiliation: 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.
authors.forename: Rozita
authors.initials: R
authors.lastname: Rosli
authors.affiliation: UMR-MD1, Aix-Marseille Université, IRBA, Faculté de Médecine, 27 boulevard Jean Moulin, 13385, Marseille, France.
authors.forename: Jean-Marie
authors.initials: JM
authors.lastname: Pagès
authors.affiliation: 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.
authors.forename: Clotilde
authors.initials: C
authors.lastname: Policar
authors.affiliation: 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.
authors.forename: Nicolas
authors.initials: N
authors.lastname: Delsuc
authors.affiliation: 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.
authors.forename: Karen A
authors.initials: KA
authors.lastname: Crouse
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D045744:Cell Line, Tumor; D056831:Coordination Complexes / Q000737:chemistry / Q000494:pharmacology; D003300:Copper / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D006834:Hydrazines / Q000737:chemistry / Q000494:pharmacology; D047028:Macrocyclic Compounds / Q000737:chemistry / Q000494:pharmacology*; D012545:Schiff Bases / Q000737:chemistry* / Q000494:pharmacology
chemical_list: D000900:Anti-Bacterial Agents; D056831:Coordination Complexes; D006834:Hydrazines; D047028:Macrocyclic Compounds; D012545:Schiff Bases; C010877:carbazic acid; D003300:Copper
keywords: Bioactivity; Copper complexes; Dithiocarbazate; Gram-negative; Gram-positive; MCF-7; MDA-MB-231; Macroacyclic ligand; NNSS ligand; Schiff base; Tetradendate ligand