Structural, thermogravimetric, B3LYP and biological studies on some heterocyclic thiosemicarbazide copper (II) complexes and evaluation of their molecular docking

A new Schiff base hydrazone (Z)‐2‐(2‐aminothiazol‐4‐yl)‐N′‐(2‐hydroxy‐3‐methoxybenzylidene) acetohydrazide (H2L) and its chelates [VO (HL)2]·5H2O, [Cu (HL)Cl(H2O)]·2H2O and [Fe(L)Cl(H2O)2]·3H2O have been isolated and characterized using different physico‐chemical methods, for example infrared (IR), electron paramagnetic resonance (EPR), thermogravimetric analysis and DTG in the solid state, and 1H‐NMR, 13C‐NMR and UV in solution. Magnetic and UV–visible measurements proposed that the coordination environments are square pyramidal, tetrahedral and octahedral geometries for oxovanadium (IV), Cu (II) and Fe (III), respectively. The ligand acts as mono‐negative NO towards oxovanadium (IV) and Cu (II) ions, and bi‐negative ONO for Fe (III) ion. The geometries of the ligand and its complexes were performed using Gaussian 9 program with density functional theory. The EPR spectral data of oxovanadium (IV) and Cu (II) chelates confirmed the mentioned geometries. The molecular modeling was done, and illustrated bond lengths, bond angles, molecular electrostatic potential, Mulliken atomic charges and chemical reactivity for the inspected compounds. Theoretical IR and 1H‐NMR of the free ligand were calculated. Furthermore, thermodynamic and kinetic parameters for thermal decomposition steps were studied. Docking study of H2L was applied against the proteins of both bacterial strains Staphylococcus aureus and Escherichia coli, as well as the protein of xanthine oxidase as antioxidant agent by Schrödinger suite program utilizing XP glide protocol. Furthermore, antimicrobial, antioxidant and DNA‐binding activities of the compounds have been carried out.

Section: Methodsmentioning

confidence: 99%

“…In continuance of our earlier work, we presented here the coordination manner of H 2 L with oxovanadium (IV), Cu (II) and Fe (III) ions utilizing modeling and spectroscopic techniques in addition to molecular docking of the ligand against two bacterial strains, DNA‐binding and antioxidant activities.…”

Section: Introductionmentioning

confidence: 96%

Synthesis, spectroscopic, DFT, biological studies and molecular docking of oxovanadium (IV), copper (II) and iron (III) complexes of a new hydrazone derived from heterocyclic hydrazide

El‐Gammal

El‐Reash

Bedier

2019

“…Based on these images, the particle size was found to be around 100 nm, with the particles being both cubic and spherical. Although different methods have been applied to prepare nanoparticles from metal oxides, this report is a scarce report on the synthesis of nanoparticles of metal Schiff base complexes.…”

Section: Resultsmentioning

confidence: 99%

“…This metal‐complexing ability is responsible for their biological activity. Thiosemicarbazide derivatives also show a wide range of biological activity, acting as antioxidant, antimicrobial, anticonvulsant, anticancer, antimalarial, and anti‐inflammatory agents . Because of the ease of coordination of thiosemicarbazide with transition metals, they influence the latter's chemical and biological properties.…”

Section: Introductionmentioning

confidence: 99%

Evaluation of newly synthesized derivatives of bis(hydrazine‐1‐carbothioamide) and their metal complexes synthesized in bulk and nano size as potent anticancer agents

Taha

Saleh

Elhady

et al. 2019

A series of new metal complexes were synthesized in both bulk and nano size using green methods, starting with the reaction of (E)-N′-[(E)-2bromobenzylidene]-4-oxo-4-(piperidin-1-yl)but-2-enehydrazide with thiosemicarbazide and different metal halides such as CuI·2H 2 O, CuCl 2 ·2H 2 O, CoCl 2 ·2H 2 O, and ZnCl 2 ·2H 2 O, and metal nitrate such as Ga(NO 3 ) 3 ·2H 2 O.Structures of these metal complexes were confirmed using different spectroscopic methods, elemental analysis, electronic spectra, and microanalytical methods (scanning electron microscopy and transmission electron microscopy) for nano complexes. The distorted octahedral geometry for all complexes was suggested based on magnetic moments and electronic spectral studies. The cytotoxic activity of the compounds was investigated against human hepatocellular carcinoma (HepG2) and human colorectal carcinoma (HCT-116) cell lines. Most tested compounds had higher inhibitory activity than the standard vinblastine drug. Interestingly, the nano-sized Ga(III) complex 11 was the most potent compound against the two tested cell lines, with 50% inhibitory concentration (IC 50 ) of 2.56 μg/mL for HepG2, compared with the reference drug vinblastine (IC 50 15.6 μg/mL), and IC 50 4.64 μg/mL for HCT-116, compared with the standard (IC 50 13.9 μg/mL). The bioassay results helped us identify new potent and selective anticancer agents.

“…Moreover, the Cu (II) complexes exhibited antioxidant activity of diphenyl picryl hydrazyl (DPPH) scavenging and superoxide dismutase (SOD) like activity . An extension of previous work, this work purposes to prepare and characterize Cr (III), Mn (II) and Cu (II) complexes of ( E )‐ N ‐(2‐hydroxy‐3‐methoxy benzylidene)picolinohydrazide (H 2 POV). The possible approaches of chelation, geometries and the complexes bonding are concluded by magnetic measurements, quantum calculations (DFT) and the various spectroscopic techniques ( 1 H NMR, 13 C NMR, FT‐IR, EI‐Mass spectra, UV–visible and EPR).…”

Section: Introductionmentioning

confidence: 99%

Spectroscopic and theoretical studies on Cr (III), Mn (II) and Cu (II) complexes of hydrazone derived from picolinic hydrazide and O‐vanillin and evaluation of biological potency

Al‐Hazmi

Abou‐Melha

El‐Metwaly

et al. 2019

Trivalent Cr (III) and divalent of both Mn (II) and Cu (II) complexes containing hydrazone ligands derived from the condensation of picolinohydrazide with O‐vanillin were synthesised and characterized by elemental analysis, spectral and magnetic measurements. The suggested octahedral structures were confirmed by applying DFT optimization and conformational studies. The thermal decomposition behaviour of Mn (II) complex is discussed. The evaluation of kinetic parameters (Ea, A, ∆H, ∆S and ∆G) of all thermal degradation stages have been evaluated using Coats‐Redfern and Horowitz‐Metzger approaches. The band gap results suggested that these complexes are semi‐conductors and lie in same range of highly efficient photovoltaic materials. Antibacterial studies showed that higher activity of complexes than of ligands. Assay on the antioxidant activity (DPPH and SOD) of the above complexes revealed the high SOD‐activity of Mn (II) complex and high DPPH‐activity for ligand.