Anticancer activities of a β-amino alcohol ligand and nanoparticles of its copper(ii) and zinc(ii) complexes evaluated by experimental and theoretical methods

Abstract

2-(2-Hydroxyethylamino)ethylamino)cyclohexanol (HEAC) and copper and zinc complexes, [Cu(HEAC) Cl]Cl (1), [Cu(HEAC)Br]Br (2), [Zn(HEAC)Cl 2 ] (3), were prepared and identified by elemental analysis, FT-IR, UV-Vis, 1 H NMR spectroscopy and single-crystal X-ray diffraction. Also nanoparticles of 1-3 were prepared for anticancer studies by ultrasonic irradiation. Particle size and morphology of the nano particles are investigated by PXRD and SEM, respectively. X-ray analysis revealed that the ionic complexes 1 and 2 are isostructural. In the structure of complexes 1 and 2, the metal atom has a CuN 2 O 2 X (X: Cl (1), Br (2)) environment with square-pyramidal geometry, containing the tetradentate N 2 O 2 -donor HEAC. The bond length of the axial position in the square-pyramidal geometry of 1 and 2 is elongated. Complex 3 has a ZnN 2 OCl 2 environment with trigonal bipyramidal geometry around the zinc atom in which the HEAC acts as mer-N 2 O-donor. The ability of HEAC and nano particles 1-3 to interact with the nine biomacromolecules (BRAF kinase, CatB, DNA gyrase, HDAC7, rHA, RNR, TrxR, TS and Top II) are investigated by docking calculations. For examination of the docking results, the in vitro activities of four compounds against the human leukemia cell line K562 were investigated by evaluation of IC 50 values and mode of cell death (apoptosis). The thermodynamic stability of the compounds along with the charge distribution pattern were studied by DFT and NBO analysis, respectively.

Structural conversion of an oxazolidine ligand upon treatment with copper(I) and (II) halides; structural, spectral, theoretical and docking studies

“…For predicting the biological activities of AEPC and 1-3, interactions of these compounds with nine macromolecule receptors using Gold [34] docking software were studied. The Gold docking results are reported in terms of the values of fitness which means that the higher the fitness, the better the docked interaction of the compounds [18][19][20][21]. The results of the docking presented in this work are the best binding results out of the ten favorites predicted by Gold.…”

“…The general features from the Gold docking prediction (table 8) show that all studied structures can be considered as biologically active compounds [18][19][20]. The best predicted targets for AEPC is HDAC7, while for the studied complexes TrxR is the target.…”

“…For predicting the biological activities of the ligand and complexes, docking calculations were run to investigate the possibility of an interaction between these compounds and nine protein targets [18][19][20] to study the possibility of anticancer properties of the compounds, also acting as antimalarial agents [21].…”

A binuclear Cd(II) complex containing bridging pyrimidine-based ligands

“…Based on the calculated charge average for N atoms, the charges on the coordinated nitrogen atoms (N a and N c , Scheme 1) become more negative after coordination. Also, as is typical, the charge on the cadmium atom (+1.14) is lower than the formal charge (+2) owing to electron donation of the ligands upon complexation [25,26].…”

Reaction of 2-[(2-aminoethyl)amino]ethanol with pyridine-2-carbaldehyde and complexation of the products with CuII and CdII along with docking studies

“…In addition to the expected biological properties of POPME and PMAE, binding of PMAE to Cu II ion makes this complex a good choice for a biologically active compound (Shahabadi et al, 2017;Jopp et al, 2017;Sanz Del Olmo et al, 2017;Mardani et al, 2018b;Saghatforoush et al, 2018). To study the biological activities of PMAE and its copper complex along with POPME, docking calculations were run to investigate the possibility of interactions between these compounds and ten protein targets (Marandi et al, 2018a,b,c;Mardani et al, 2018a,b;Saghatforoush et al, 2018), namely BRAF kinase, Cathepsin B (CatB), DNA gyrase, Histone deacetylase (HDAC7), recombinant Human albumin (rHA), Ribonucleotide reductases (RNR), Thioredoxin reductase (TrxR), Thymidylate synthase (TS) and Topoisomerase II (Top II), along with B-DNA.…”