ABSTRACT
A new hexanuclear Zn(II) complex with the ligand 2,2'-(piperazine-1,4-diyl)bis(ethan-1-amine), [L3Zn6(OH)6][ClO4]6·3MeOH·7H2O, was synthesized. The crystal structure of this complex showed that each Zn atom is in a distorted tetrahedral coordination environment, surrounded by two nitrogen atoms from each ligand and two hydroxide groups, each of which bridges to another Zn atom. The anticancer activities of the ligand and its metal complex against the breast cancer cell line (MCF-7) indicated that the zinc complex had a greater anticancer activity. The free ligand and its metal complex were evaluated for antioxidant activity using the DPPH scavenging method. In addition, the antibacterial activities of both compounds were screened against Gram-positive (Staphylococcus aureus) and Gram-negative (Escherichia coli) bacteria. The interaction of these compounds with DNA and AChE was also investigated using molecular docking.
Subject(s)
Anti-Infective Agents , Coordination Complexes , Antioxidants/pharmacology , Antioxidants/chemistry , Molecular Docking Simulation , X-Rays , Ligands , Anti-Infective Agents/chemistry , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/chemistry , Coordination Complexes/chemistry , Zinc/pharmacology , Zinc/chemistry , Microbial Sensitivity TestsABSTRACT
A new ligand (L) containing two nitro phenyl rings as side chains was synthesized. The reaction of this ligand with copper(II) and zinc(II) metal ions gave complexes with different coordination environments. The free ligand and the metal complexes were characterized using a number of spectroscopic methods. The crystal structure of [ZnLBr]ClO4 showed that the Zn(II) ion was in a distorted square pyramidal environment. The crystal structure of [CuL](ClO4)2 showed that the Cu(II) ion is in a tetragonally distorted octahedral environment. Molecular docking studies with DNA indicated that the binding of L, [ZnLBr]ClO4 and [CuL](ClO4)2 involved the major groove of DNA, H-bonds and Vander Waals interactions. In contrast, the molecular docking of L, [ZnLBr]ClO4 and [CuL](ClO4)2 with human glutathione reductase (GR) showed that the dominant interactions of these compounds with GR were H-bonding, vander Waals and hydrophobic interactions. The antioxidant activity of the synthesized complexes was analyzed by the free radical scavenging activity using 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay with [CuL](ClO4)2 showing maximum activity. In addition, in vitro anticancer activity of the complexes against human breast MCF-7 cancer cell line was confirmed through 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium (MTT) assay. All compounds showed a dose-dependent inhibitory effect on the growth of breast cancer cells with the inhibition activity of [CuL](ClO4)2 being more active than the other synthesized compounds. Furthermore, results from the antibacterial activity screening of the compounds against two Gram-positive and Gram-negative pathogenic bacteria by the micro-broth dilution and disk diffusion methods indicated that [CuL](ClO4)2 complex had the strongest antibacterial potential.
Subject(s)
Coordination Complexes , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Coordination Complexes/chemistry , Coordination Complexes/pharmacology , Copper/chemistry , Crystallography, X-Ray , DNA/chemistry , Gram-Negative Bacteria , Humans , Ligands , Molecular Docking Simulation , Molecular Structure , X-Rays , Zinc/pharmacologyABSTRACT
The synthesis of five- and six-membered oxygen- and nitrogen-containing heterocycles has been regarded as the most fundamental issue in organic chemistry and chemical industry because they are used in producing high-value products. In this study, an efficient, economic, sustainable, and green protocol for multicomponent synthesis has been developed. The one-pot direct Knoevenagel condensation-Michael addition-cyclization sequences for the transformation of aromatic aldehydes, malononitrile, and 4-hydroxycoumarin or phthalhydrazide generate the corresponding dihydropyrano[2,3-c]chromenes and 1H-pyrazolo[1,2-b]phthalazine-5,10-diones over a novel mesoporous metal-organic framework-based supported Cu(II) nanocatalyst [UiO-66@Schiff-Base-Cu(II)] under ambient conditions. Moreover, the [UiO-66@Schiff-Base-Cu(II)] complex efficiently catalyzed the selectively large-scale synthesis of the target molecules with high yield and large turnover numbers. As presented, the catalyst demonstrates excellent reusability and stability and can be recycled up to six runs without noticeable loss of activity. Moreover, ICP-AES analysis showed that no leaching of Cu complex occurred during the recycling process of the heterogeneous [UiO-66@Schiff-Base-Cu(II)] nanocatalyst.
