Abstract:Key indicators: single-crystal X-ray study; T = 291 K; mean (C-C) = 0.006 Å; R factor = 0.045; wR factor = 0.121; data-to-parameter ratio = 13.2.The Cu II atoms in the two independent molecules of the title compound, [Cu(C 7 H 5 O 3 ) 2 (C 14 H 12 N 2 )], are each coordinated by a bidentate 2,9-dimethyl-1,10-phenanthroline (dmphen) molecule and two monodentate 2-hydroxybenzoate anions in a distorted tetrahedral geometry. The crystal packing is stabilized by intramolecular hydrogen bonding andinteractions betwe… Show more
“…Instead a four-coordinate complex is envisaged with the copper(II) centre bound to the bathocuproinedisulfonic acid disodium moiety via two nitrogen atoms and to two indomethacin units via monodentate interactions (as depicted in Figure 1). Indeed, copper(II) complexes with two 2,9-dimethyl-1,10-phenanthroline ligands, or one 2,9-dimethyl-1,10-phenanthroline ligand and two monodentate ligands have been reported to adopt distorted tetrahedral structures [19,20,21]. The presence of the disulfonic acid disodium groups promotes water solubility, therefore as well as being more stable towards biological reduction (than 1 ), 2 is expected to be more hydrophilic (than 1 ) and thus more suitable for in vivo administration and drug formulation.…”
Copper(II) complexes bearing nonsteroidal anti-inflammatory drugs (NSAIDs) are known to potently kill cancer stem cells (CSCs), a subpopulation of tumour cells with high metastatic and relapse fidelity. One of the major disadvantages associated to these copper(II) complexes is their instability in the presence of strong cellular reductants (such as ascorbic acid). Here we present a biologically stable copper(II)-NSAID complex containing a bathocuproinedisulfonic acid disodium ligand and two indomethacin moieties, Cu(bathocuproinedisulfonic acid disodium)(indomethacin)2, 2. The copper(II) complex, 2 kills bulk breast cancer cells and breast CSC equally (in the sub-micromolar range) and displays very low toxicity against non-tumorigenic breast and kidney cells (IC50 value > 100 µM). Three-dimensional cell culture studies show that 2 can significantly reduce the number and size of breast CSC mammospheres formed (from single suspensions) to a similar level as salinomycin (an established anti-breast CSC agent). The copper(II) complex, 2 is taken up reasonably by breast CSCs and localises largely in the cytoplasm (>90%). Cytotoxicity studies in the presence of specific inhibitors suggest that 2 induces CSC death via a reactive oxygen species (ROS) and cyclooxygenase isoenzyme-2 (COX-2) dependent apoptosis pathway.
“…Instead a four-coordinate complex is envisaged with the copper(II) centre bound to the bathocuproinedisulfonic acid disodium moiety via two nitrogen atoms and to two indomethacin units via monodentate interactions (as depicted in Figure 1). Indeed, copper(II) complexes with two 2,9-dimethyl-1,10-phenanthroline ligands, or one 2,9-dimethyl-1,10-phenanthroline ligand and two monodentate ligands have been reported to adopt distorted tetrahedral structures [19,20,21]. The presence of the disulfonic acid disodium groups promotes water solubility, therefore as well as being more stable towards biological reduction (than 1 ), 2 is expected to be more hydrophilic (than 1 ) and thus more suitable for in vivo administration and drug formulation.…”
Copper(II) complexes bearing nonsteroidal anti-inflammatory drugs (NSAIDs) are known to potently kill cancer stem cells (CSCs), a subpopulation of tumour cells with high metastatic and relapse fidelity. One of the major disadvantages associated to these copper(II) complexes is their instability in the presence of strong cellular reductants (such as ascorbic acid). Here we present a biologically stable copper(II)-NSAID complex containing a bathocuproinedisulfonic acid disodium ligand and two indomethacin moieties, Cu(bathocuproinedisulfonic acid disodium)(indomethacin)2, 2. The copper(II) complex, 2 kills bulk breast cancer cells and breast CSC equally (in the sub-micromolar range) and displays very low toxicity against non-tumorigenic breast and kidney cells (IC50 value > 100 µM). Three-dimensional cell culture studies show that 2 can significantly reduce the number and size of breast CSC mammospheres formed (from single suspensions) to a similar level as salinomycin (an established anti-breast CSC agent). The copper(II) complex, 2 is taken up reasonably by breast CSCs and localises largely in the cytoplasm (>90%). Cytotoxicity studies in the presence of specific inhibitors suggest that 2 induces CSC death via a reactive oxygen species (ROS) and cyclooxygenase isoenzyme-2 (COX-2) dependent apoptosis pathway.
“…Cu(phen)2(Hsal)]. [Hsal][H2O]},[9], dimeric {[Cu2(phen)2(sal)2]•2H2O}[9] and polymeric forms[13] depending on the nature of ligands, and reaction conditions such as temperature, pH, solvent system etc[14][15]. The carboxylate moiety being coordinatively flexible, can assume monodentate, bidentate, or bridging coordination modes.…”
Two copper(II) coordination complexes, formulated as [Cu(tmen)(ClBA)2] (1) and [Cu(tmen)(Hsal)2.H2O] (2), (where tmen = N,N,N′,N′-tetramethylethylenediamine (C6H16N2), ClBA = 2-chlorobenzoate (C7H4ClO2 1-) and Hsal 1-(C7H5O3 1-) = monoanion of o-hydroxybenzoic acid (salicylic acid), have been synthesized and characterized by elemental combustion analysis, spectroscopic techniques, thermal studies and single crystal X-ray analyses. The complex (1) consists of two distinct monomeric units in which coordination environment around the central copper(II) ion is a distorted octahedron with CuN2O4 chromophore, constituted by; a chelating tmen molecule, and two 2-chlorobenzoate 1anions coordinated through their carboxylate-O atoms in an asymmetrical bidentate fashion. The complex (2), is also a monomer and consists of CuN2O3 chromophore, in which tmen is coordinated to Cu(II) through its two N atoms in a chelating bidentate fashion, an aqua-O and the two o-hydroxybenzoate 1-(HSal 1-) anions coordinated through one of their carboxylate-O atoms in a monodentate mode, forming a square pyramidal structure. Hydrogen bonding interactions especially of O-HO, N-HO, and C-HCl types interweave monomeric units and stabilize the overall crystal structures in both complexes. Thermal analysis and antibacterial activities of 1 and 2, against various bacterial strains are also investigated.
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