Design, synthesis, spectral characterization, photo‐cleavage, and in vitro evaluation of anticancer activities of new transition metal complexes of piperazine based Schiff base‐oxime ligand

Abstract

The newly synthesized Schiff base‐oxime ligand, namely, (2Z,3E)‐3‐((3‐(4‐(3‐(((2E,3E)‐3‐(hydroxyimino)butan‐2‐ylidene)amino)propyl)piperazin‐1‐yl)propyl)imino)butan‐2‐one oxime (H2L) and its Co (II), Cu (II), and Zn (II) complexes were reported. The characterization was accomplished with the aid of CHN‐EA, mass, fourier transform infrared spectroscopy (FT‐IR), electronic spectra, magnetic moment, molar conductance and TGA. According to the spectroscopic approaches, the synthesized ligand (H2L) may act as a tetradentate or hexadentate (bis‐tridentate) coordinating ligand through the azomethine nitrogen, piperazinyl nitrogens, and oximato‐nitrogens affording distorted square planar mononuclear Co (II) complex or tetrahedrally distorted square planar binuclear Cu (II) and Zn (II) complexes whereas the coordination mode varies according to the nature of the metal ion. The microbial resistance of all the synthesized compounds was evaluated and reported. Findings showed that the Cu (II) complex has mostly the highest inhibitory effects against all tested microbial strains. Besides, the anticancer nature of the studied compounds was also evaluated against a panel of three different human cancer cells, including (HCT‐116), (MDA‐MB‐231), (HepG2) in addition to the (WI‐38) used as a healthy cells. In general, the Cu (II) complex displayed the best cytotoxic profiles against the tested cells than the Co (II) and Zn (II) complexes with negligible toxicity towards the (WI‐38) normal cells. The DNA cleavage activities of all tested compounds were assayed against pBR322 plasmid DNA. Whereas, the Cu (II) complex showed the highest DNA cleavage propensity, which proceeds predominantly via the oxidative mechanism. Additionally, flow cytometric analysis dictates that the Cu (II) complex induces cell cycle arrest in S‐phase and apoptotic cell death on HCT‐116 cells. The morphological transformations distinguished in HCT‐116 cells treated with Cu (II) complex have been depicted with the aid of scanning electron microscopy (SEM). The docking results indicate that the Cu (II) complex strongly interacts with human colon cancer (6GUE), Escherichia coli (3T88), Klebsiella pneumoniae (4HL2), and Staphylococcus aureus (3WQU) proteins, through different modes of interactions that harmonize successfully with the experimental results.

Novel hybrid thiazoles, bis-thiazoles linked to azo-sulfamethoxazole: Synthesis, docking, and antimicrobial activity

“…Thus, molecular docking has been utilized to give additional insight into the potential molecular mechanism of the synthesized compounds. Molecular docking has greatly contributed to the pursuit of potentially new compounds of therapeutic interest as an innovative approach for rationalizing, forecasting the affinities of compounds at a molecular basis, and assessing the suitable orientations and binding of compounds under study at pockets of receptor proteins [ [78] , [79] , [80] ]. The primary objective is to investigate how our novel sulfonamides will interact with different bacterial proteins, namely MurE ligase (PDB ID: 4C13 ), tyrosyl-tRNA synthetase (PDB ID: 1JIJ ), and dihydropteroate synthase (PDB ID: 1AJ0 ), that are considered as crucial targets for finding broad-spectrum antibiotics [ [81] , [82] , [83] , [84] , [85] , [86] , [87] ].…”

Hantzsch‐Like Synthesis, DNA Photocleavage, DNA/BSA Binding, and Molecular Docking Studies of Bis(sulfanediyl)bis(tetrahydro‐5‐deazaflavin) Analogs Linked to Naphthalene Core

“…The three‐dimensional (3D) structure of 14b was drawn by the Molecular Operating Environment (MOE‐2015) software [67,68] . Energy minimization was carried out using MOE by default force‐field MMFF94x method while keeping RMS gradient at 0.001 kcal mole −1 .…”

“…The three-dimensional (3D) structure of 14b was drawn by the Molecular Operating Environment (MOE-2015) software. [67,68] Energy minimization was carried out using MOE by default force-field MMFF94x method while keeping RMS gradient at 0.001 kcal mole À 1 . The crystallographic structures of the DNA and BSA were obtained from the protein data bank (PDB ID: 1BNA and 4OR0, respectively).…”

“…Bovine serum albumin (BSA), one of SAs, is frequently used in biochemical studies due to its structural similarities with human serum albumin and a variety of physiological functions. Therefore, considerable attention has recently been paid to synthesize novel anticancer drugs that target DNA and/or proteins with potential cytotoxicity [67–69] …”

Synthesis of a new sulfadimidine Schiff base and their nano complexes as potential anti-COVID-19 and anti-cancer activity

“…Furthermore, Schiff bases are an essential class of ligands in coordination chemistry. Schiff bases have also been demonstrated to have antibacterial, antifungal, antimalarial, antiviral, anti-inflammatory, and antipyretic effects, among other biological actions [10][11][12][13][14][15] . The creation of novel compounds with unique physical, chemical, and biological properties results from the synthesis of nano-sized complexes 16 .…”