Semiempirical studies, spectral analysis, in vitro antibacterial and DNA degradation studies of heterocyclic thiosemicarbazone ligand and its metal complexes

Yousef, Tarek A.; Al-Duaij, Omar K.; El‐Reash, G.M. Abu; Morshedy, R.M. El

doi:10.1016/j.molliq.2016.07.075

Cited by 35 publications

(44 citation statements)

References 48 publications

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“…When the system acquires an additional electronic charge (Δ N max ) from the environment, the electrophilicity index ( χ ) is positive. The direction of charge transfer is entirely determined by the electronic chemical potential ( Pi ) of the molecule because an electrophile is a chemical species capable of accepting electrons from the environment and its energy must decrease upon accepting an electronic charge . Therefore, its electronic chemical potential must be negative, as supported by the values in Table and Supporting Information Table S1.…”

Section: Resultsmentioning

confidence: 96%

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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Section: Resultsmentioning

confidence: 96%

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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“…This is also confirmed from the calculated chemical potential Pi . The reactivity index measures the stabilization in energy when the system acquires an additional electronic charge (Δ N max ) from the environment; the electrophilicity index ( χ ) is positive. Definite quantity and direction of the charge transfer is completely determined by the electronic chemical potential ( Pi ) of the molecule because an electrophile is a chemical species capable of accepting electrons from the environment and its energy must decrease upon accepting electronic charge . Therefore, its electronic chemical potential must be negative exactly as supported by the values in Tables and .…”

Section: Resultsmentioning

confidence: 98%

Synthesis, characterization, density functional theory, X‐ray study, thermal stability, and biological and MOE relevance of metal complexes of griseofulvin

Mahmoud

2018

Applied Organom Chemis

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Metal(II) and metal(III) coordination compounds of griseofulvin (GFV) drug were synthesized. The structure of the ligand was determined on the basis of elemental analyses, infrared and 1 H NMR spectroscopies and thermal studies.GFV behaved as a neutral tridentate chelating agent and coordinated to metal ions through three oxygen atoms: two methoxy groups and oxygen atom of furan ring. Metal complexes were characterized by means of elemental analyses and molar conductance, spectral (infrared, electron spin resonance) and thermal studies. All the complexes showed molar conductance behaviour corresponding to an electrolytic nature. All the complexes showed octahedral geometry, except [Zn(GFV)Cl]Cl that showed tetrahedral geometry. Density functional theory (DFT) calculations were employed to understand and estimate the contribution of each interaction in the formation of the assembly using several theoretical models. The computed parameters from DFT calculations for structure optimizations and vibrational frequencies were in good agreement with the experimental data. Newly synthesized metal complexes in addition to GFV were examined against opportunistic pathogens. The biological applications of complexes were studied with two Gram-positive bacteria (Bacillus subtilis and Staphylococcus aureus) and two Gram-negative bacteria (Escherichia coli and Neisseria gonorrhoeae) as well as their antifungal activity against Candida albicans. Results suggested that metal complexes were more biologically sensitive than free ligand. The complexes showed a moderate inhibition of MCF7 breast cancer cell line growth. Molecular docking studies further helped in understanding the mode of action of the compounds through their various interactions with the crystal structures of: human serum albumin (PDB: 5FUO), Staphylococcus aureus nucleoside (PDB: 3Q8U), human acetylcholinesterase (PDB: 1B41) and the human DNA-Topo I complex (PDB: 1SC7).

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“…This fact agree well with results that parent molecule H 4 BPCD have lowest value of χ so it could be considered as Lewis base (soft base). Thus Lewis base ligands are most efficacy for complex formation . Thereby, it is deduced that the ligand with a proper softness (σ) value has a good propensity to coordinate metal ions effectively .…”

Section: Resultsmentioning

confidence: 99%

Spectroscopic investigation, DFT, fluorescence, molecular docking and biological studies of divalent and trivalent binuclear complexes prepared from benzoyl thiosemicarbazide derivative of 2‐benzylmalonohydrazide

El‐Morshedy

El‐Gamil²,

Abou-Elzahab

et al. 2019

Applied Organom Chemis

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The binuclear Cr (III), Mn (II) and Fe (III) complexes of N,N′‐(2,2′‐(2‐benzylmalonyl)bis (hydrazine‐1‐carbonothioyl))dibenzamide (H4BPCD), which derived from the combination of 2‐benzylmalonohydrazide suspension with benzoyl‐isothiocyanate, have been isolated and investigated by the necessary analytical and spectroscopic techniques. The IR studies show that H4BPCD dispose as a mono‐negative hexadentate ligand (NOS)2 towards Mn (II) ion and tetra‐negative hexadentate (NOS)2 towards both Cr (III) and Fe (III) ions. The values of molar conductance in DMSO suggested the non‐electrolytic nature for all complexes. The magnetic measurements and the electronic transitions data confirmed the hexa‐coordinate geometry of complexes. The DFT geometry optimization of all compounds and IR comparative study of both theoretical and experimental of H4BPCD were carried out. Moreover, the H4BPCD and its Cr (III) complex displayed intra ligand (π → π*) fluorescence emission spectra which corroborate their photoactive nature. The coordinated and crystalline water molecules have been investigated by (TG/DTG) studies. The kinetic and thermodynamic parameters were computed using Horowitz‐ Metzger, Coats‐Redfern and Broido methods. Biological studies of DNA binding, minimum inhibitory concentration, in vitro determination of SOD‐like activity and MTT‐cytotoxicity assay as well as molecular docking studies were tested for the ligand and its complexes.

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Semiempirical studies, spectral analysis, in vitro antibacterial and DNA degradation studies of heterocyclic thiosemicarbazone ligand and its metal complexes

Cited by 35 publications

References 48 publications

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

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

Synthesis, characterization, density functional theory, X‐ray study, thermal stability, and biological and MOE relevance of metal complexes of griseofulvin

Spectroscopic investigation, DFT, fluorescence, molecular docking and biological studies of divalent and trivalent binuclear complexes prepared from benzoyl thiosemicarbazide derivative of 2‐benzylmalonohydrazide

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