Synthesis, anticancer activity and molecular docking study of Schiff base complexes containing thiazole moiety

Abd-Elzaher, Mokhles M.; Labib, Ammar A.; Mousa, Hanan A.; Moustafa, Samia A.; Ali, Mamdouh M.; El-Rashedy, Ahmed A.

doi:10.1016/j.bjbas.2016.01.001

Cited by 108 publications

(75 citation statements)

References 53 publications

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“…The cytotoxicity of the tested compounds was expressed as IC 50 , which is the median growth inhibitory concentration affording 50% cytotoxic effect against cancer cells after 48 h treatment with the tested compounds. The Cu(II) complex ( 4 ) was found to have the highest cytotoxicity against Hep‐G 2 and MCF‐7 cell lines with IC 50 = 6.10 and 5.2 μg ml −1 in comparison with H 4 L, doxorubicin and the other metal complexes . This is due to reduction of Cu(II) to Cu(I) by superoxide anion which is produced from the reduction of molecular oxygen that is generated in biological processes .…”

Section: Resultsmentioning

confidence: 98%

Coordination modes of multidentate azodye ligand derived from 4,4′‐methylenedianiline towards some transition metal ions: Synthesis, spectral characterization, thermal investigation and biological activity

Abouel‐Enein

Emam

Monir

2018

Applied Organom Chemis

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Nine new azodye metal complexes of Mn(II), Co(II), Ni(II), Cu(II), Cr(III), Fe(III), Ru(III), Hf(IV) and Zr(IV) ions have been prepared via the reaction of 5,5′‐((1E,1′E)‐(methylenebis(1,4‐phenylene))bis(diazene‐2,1‐diyl))bis(6‐hydroxy‐2‐thioxo‐2,3‐dihydropyrimidin‐4(5H)‐one) (H4L) with the corresponding metal salts affording sandwich (1 L:1 M), mononuclear (2 L:1 M), binuclear (1 L,2 M) and tetranuclear (1 L,4 M) complexes. Elemental analyses, spectral methods, magnetic moment measurements and thermal studies were utilized to confirm the mode of bonding and geometrical structure for the ligand and its metal complexes. Infrared spectral data show that the H4L ligand chelates with some metal ions in keto–enol–thione or keto–thione manner. It behaves in a neutral/dibasic tetradentate fashion in sandwich and binuclear complexes. Also, it acts as a neutral bidentate moiety in the Cr(III) complex. The spectra reveal that azo group participates in chelation in all complexes. Octahedral geometry was suggested for all chelates but the Cu(II) complex with square planar geometry. The thermal stability and decomposition of the compounds were studied, the data showing that the thermal decomposition ended with metal or metal oxide mixed with carbon as final product. The electron spin resonance spectrum of the Cu(II) complex demonstrates that the free electron is located in the ( dx2−y2) orbital. Measurements of biological activity against human cell lines Hep‐G2 and MCF‐7 reveal that the Cu(II) complex has a higher cytotoxicity in comparison to the free ligand and other metal complexes, with IC50 values of 6.10 and 5.2 μg ml−1, respectively, while the ligand has anti‐tumour activity relative to some of the investigated metal complexes.

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Section: Resultsmentioning

confidence: 98%

Coordination modes of multidentate azodye ligand derived from 4,4′‐methylenedianiline towards some transition metal ions: Synthesis, spectral characterization, thermal investigation and biological activity

Abouel‐Enein

Emam

Monir

2018

Applied Organom Chemis

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“…The Dock scoring in the MOE software was done utilizing the London DG scoring function, which was upgraded by using two unrelated refinement methods: the Grid‐Min pose and the force field were improved to check that the refined poses met the specified conformations. Auto‐rotatable bonds were allowed; the best 10 binding poses were directed to analysis for achieving the best score to compare the docking poses to the ligand in the co‐crystallized structure …”

Section: Methodsmentioning

confidence: 99%

Physicochemical characterization of nanobidentate ferrocene‐based Schiff base ligand and its coordination complexes: Antimicrobial, anticancer, density functional theory, and molecular operating environment studies

Mahmoud

2019

J Chinese Chemical Soc

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A novel bidentate Schiff base ligand (HL, Nanobidentate Ferrocene based Schiff base ligand L (has one replaceable proton H)) was prepared via the condensation of 2‐amino phenol with 2‐acetyl ferrocene. The ligand was characterized using elemental analysis, mass spectrometry, infrared (IR) spectroscopy, 1proton nuclear magnetic resonance (H‐NMR) spectroscopy, scanning electron microscopy (SEM), and thermal analysis. The corresponding 1:1 metal complexes with some transition‐metal ions were additionally characterized by their elemental analysis, molar conductance, SEM, and thermogravimetric ana1ysis (TGA). The complexes had the general formula [M(L)(Cl)(H2O)3]xCl·nH2O (M = Cr(III), Mn(II), Fe(III), Co(II), Ni(II), Cu(II), Zn(II), and Cd(II)), (x = 0 for Mn(II), Co(II), Ni(II), Cu(II), Zn(II), and Cd(II), x = 1 for Cr(III) and Fe(III)), (n = 1 for Cr(III), n = 3 for Mn(II) and Co(II), n = 4 for Fe(III), Ni(II), Cu(II), Zn(II), and Cd(II)). Density functional theory calculations on the HL ligand were also carried out in order to clarify molecular structures by the B31YP exchange‐correlation function. The results were subjected to molecular orbital diagram, highest occupied mo1ecu1ar orbital–lowest occupied molecular orbital, and molecular electrostatic potential calculations. The parent Schiff base and its eight metal complexes were assayed against four bacterial species (two Gram‐negative and two‐Gram positive) and four different antifungal species. The HL ligand was docked using molecular operating environment 2008 with crystal structures of oxidoreductase (1CX2), protein phosphatase of the fungus Candida albicans (5JPE), Gram(−) bacteria Escherichia coli (3T88), Gram(+) bacteria Staphylococcus aureus (3Q8U), and an androgen‐independent receptor of prostate cancer (1GS4). In order to assess cytotoxic nature of the prepared HL ligand and its complexes, the compounds were screened against the Michigan cancer foundation (MCF)‐7 breast cancer cell line, and the IC50 values of compounds were calculated.

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“…Succinctly, they are one of important class of compounds having therapeutic potential for the treatment of various diseases 24 . Schiff bases which can bind or cleave DNA are now in great consideration due to their importance in the development of anticancer and antimicrobial agents 1,4,5,6 . Schiff bases are characterized by imine group -N=CH-and they explicate the mechanism of transamination and racemization reactions in biological system 7 .…”

Section: Ijpsr (2018) Volume 9 Issue 1 (Research Article)mentioning

confidence: 99%

Untitled

2018

IJPSR

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Antibacterial activities, molecular docking and DNA cleavage activities of five structurally related Schiff bases [L3 (a), L3 (b), L3 (c) L3 (d) and L3 (e)] were performed and their structure activity relationship was studied. Antibacterial activities of these compounds against gram-negative and gram-positive bacteria were evaluated by using well diffusion method and the compound L3 (c); 1-[(E)-(4-hydroxyphenyl) iminomethyl] naphthalene-2-ol which carries two hydroxyl functional groups was observed as one of the most dynamic antibacterial agents. Docking interactions against p55blk kinase protein were investigated. The compound L3 (a); 1-[(E)-(3-nitrophenyl)iminomethyl]naphthalene-2-ol exhibited good docking proficiency with 24 interactions based on statistical potentials and the compound L3 (d); (E)-1-(2-methoxy-1-naphthyl)-N-(3-nitro phenyl) methanimine showed significant docking interaction based on hydrogen bonding. DNA cleavage efficiency of all the Schiff bases was investigated using Lambda DNA by gel electrophoresis method.

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Synthesis, anticancer activity and molecular docking study of Schiff base complexes containing thiazole moiety

Cited by 108 publications

References 53 publications

Coordination modes of multidentate azodye ligand derived from 4,4′‐methylenedianiline towards some transition metal ions: Synthesis, spectral characterization, thermal investigation and biological activity

Coordination modes of multidentate azodye ligand derived from 4,4′‐methylenedianiline towards some transition metal ions: Synthesis, spectral characterization, thermal investigation and biological activity

Physicochemical characterization of nanobidentate ferrocene‐based Schiff base ligand and its coordination complexes: Antimicrobial, anticancer, density functional theory, and molecular operating environment studies

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