Design and synthesis of three Fe(III) mixed-ligand complexes: Exploration of their biological and phenoxazinone synthase-like activities

Ismael, Mohamed; Abdel‐Mawgoud, A. M.; Rabia, Mostafa K.; Abdou, Aly

doi:10.1016/j.ica.2020.119443

Cited by 60 publications

(94 citation statements)

References 54 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Quantum chemical descriptor set was chosen to obtain pertinent electronic and structural features [45]. The frontier molecular orbitals (FMOs), energy gap (ΔE = E LUMO -E HOMO ), electronegativity (χ = -½ (E HOMO + E LUMO )), electronic chemical potential (μ = ½ (E HOMO + E LUMO ) = -χ), global chemical hardness (η = ½ ( ELUMO -E HOMO )), global softness (σ = 1/2η), global electrophilicity index (ω = μ 2 /2η), and nucleophilicity index (Nu = 1/ω), and dipole moment were also calculated and analyzed at the same level of theory [15,58].…”

Section: Computational Detailsmentioning

confidence: 99%

Pharmacokinetics and drug-likeness of antidiabetic flavonoids: Molecular docking and DFT study

et al. 2021

View full text Add to dashboard Cite

Computer aided toxicity and pharmacokinetic prediction studies attracted the attention of pharmaceutical industries as an alternative means to predict potential drug candidates. In the present study, in-silico pharmacokinetic properties (ADME), drug-likeness, toxicity profiles of sixteen antidiabetic flavonoids that have ideal bidentate chelating sites for metal ion coordination were examined using SwissADME, Pro Tox II, vNN and ADMETlab web tools. Density functional theory (DFT) calculations were also employed to calculate quantum chemical descriptors of the compounds. Molecular docking studies against human alpha amylase were also conducted. The results were compared with the control drugs, metformin and acarbose. The drug-likeness prediction results showed that all flavonoids, except myricetin, were found to obey Lipinski’s rule of five for their drug like molecular nature. Pharmacokinetically, chrysin, wogonin, genistein, baicalein, and apigenin showed best absorption profile with human intestinal absorption (HIA) value of ≥ 30%, compared to the other flavonoids. Baicalein, butein, ellagic acid, eriodyctiol, Fisetin and quercetin were predicted to show carcinogenicity. The flavonoid derivatives considered in this study are predicted to be suitable molecules for CYP3A probes, except eriodyctiol which interacts with P-glycoprotein (p-gp). The toxicological endpoints prediction analysis showed that the median lethal dose (LD50) values range from 159–3919 mg/Kg, of which baicalein and quercetin are found to be mutagenic whereas butein is found to be the only immunotoxin. Molecular docking studies showed that the significant interaction (-7.5 to -8.3 kcal/mol) of the studied molecules in the binding pocket of the α-amylase protein relative to the control metformin with the crucial amino acids Asp 197, Glu 233, Asp 197, Glu 233, Trp 59, Tyr 62, His 101, Leu 162, Arg 195, His 299 and Leu 165. Chrysin was predicted to be a ligand with high absorption and lipophilicity with 84.6% absorption compared to metformin (78.3%). Moreover, quantum chemical, ADMET, drug-likeness and molecular docking profiles predicted that chrysin is a good bidentate ligand.

show abstract

Section: Computational Detailsmentioning

confidence: 99%

Pharmacokinetics and drug-likeness of antidiabetic flavonoids: Molecular docking and DFT study

et al. 2021

View full text Add to dashboard Cite

show abstract

“…The ∆E , the difference between E LUMO and E HOMO , is an indication of the reactivity of the molecules. [ 31 ] Accordingly, the smaller ∆E is the more reactive molecule towards docking. Thus, the global reactivity of the investigated compounds is CuLG > NiLG > FeLG.…”

Section: Resultsmentioning

confidence: 99%

“…The subject 1‐{(E)‐[(4‐methylphenyl) imino]methyl}‐2‐naphthol ligand, HL, was previously synthesized and characterized by our group. [ 31–33 ]…”

Section: Methodsmentioning

confidence: 99%

Synthesis, structural elucidation, and density functional theory investigation of new mononuclear Fe(III), Ni(II), and Cu(II) mixed‐ligand complexes: Biological and catalase mimicking activity exploration

Abdou

Abdel‐Mawgoud

2022

Applied Organom Chemis

Self Cite

View full text Add to dashboard Cite

The present paper deals with synthesis new mononuclear 1:1:1 metal:ligand:co‐ligand complexes, FeLG, NiLG, and CuLG, where L = 1‐{(E)‐[(4‐methylphenyl)imino]methyl}‐2‐naphthol and G = Glycine. The synthesized complexes were characterized based on elemental analysis, Fourier transform infrared spectroscopy (FT‐IR), ultraviolet–visible (UV–vis), mass spectra, molar conductance, magnetic susceptibility, and thermal analysis (TGA) in addition to stoichiometry determination via molar ratio method. The isolated metal complexes showed interesting geometry variation as tetrahedral for CuLG and octahedral for both FeLG and NiLG. The molecular structures of the titled compounds were optimized theoretically using density functional theory (DFT) approach, and the quantum chemical descriptors were calculated. The disk diffusion method was used to investigate the growth inhibition of the titled compounds aganist selected pathogenic bacterial and fungal strains. The metal complexes exhibited higher enhancement as antimicrobial candidates with lower minimum inhibitory concentration (MIC) than the free ligands, and in some cases, the complexes were closed to the standard species. Molecular docking investigation was carried out to ascertain the inhibitory action of the studied compounds against 1HNJ protein, the target enzyme for the antimicrobial agents. The results indicated that the FeLG has the highest binding affinity in comparison with other compounds. Thus, these molecules could be promising antimicrobial candidates. Furthermore, catalase mimicking activity of the complexes has been investigated. The data revealed that CuLG complex catalyzes the decomposition of hydrogen peroxide most effectively. Finally, the quantum chemical parameters of the titled complexes and other different compounds were correlated with their practical biological activity data in a trial to build a SAR model.

show abstract

“…The optimized geometries were confirmed to be real minima without any imaginary vibrational frequency by performing vibrational frequency calculations. The frontier molecular orbitals (highest occupied molecular orbital, HOMO, and lowest unoccupied molecular orbital, LUMO), energy gap (Δ E = E LUMO − E HOMO ), electronegativity ( χ = − ½ ( E HOMO + E LUMO )), electronic chemical potential ( μ = ½ ( E HOMO + E LUMO ) = − χ ), global chemical hardness ( η = ½ ( E LUMO − E HOMO )), global softness (σ = 1/2η), global electrophilicity index ( ω = μ 2 /2η ), and nucleophilicity index ( Nu = 1/ ω ) , dipole moment, natural atomic charges (NAC) and molecular electrostatic potential (MEP) of the synthesized compounds were also calculated and analyzed at the same level of theory [ 54 ]. The polarizability unites were converted from au into angstrom (au/1.88973), and then to Bohr 3 (angstrom * 0.529177) using standard conversion factors.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, antibacterial and antioxidant activities of Thiazole-based Schiff base derivatives: a combined experimental and computational study

et al. 2021

View full text Add to dashboard Cite

Background Thiazole-based Schiff base compounds display significant pharmacological potential with an ability to modulate the activity of many enzymes involved in metabolism. They also demonstrated to have antibacterial, antifungal, anti-inflammatory, antioxidant, and antiproliferative activities. In this work, conventional and green approaches using ZnO nanoparticles as catalyst were used to synthesize thiazole-based Schiff base compounds. Results Among the synthesized compounds, 11 showed good activities towards Gram-negative E. coli (14.40 ± 0.04), and Gram-positive S. aureus (15.00 ± 0.01 mm), respectively, at 200 μg/mL compared to amoxicillin (18.00 ± 0.01 mm and 17.00 ± 0.04). Compounds 7 and 9 displayed better DPPH radical scavenging potency with IC50 values of 3.6 and 3.65 μg/mL, respectively, compared to ascorbic acid (3.91 μg/mL). The binding affinity of the synthesized compounds against DNA gyrase B is within − 7.5 to − 6.0 kcal/mol, compared to amoxicillin (− 6.1 kcal/mol). The highest binding affinity was achieved for compounds 9 and 11 (− 6.9, and − 7.5 kcal/mol, respectively). Compounds 7 and 9 displayed the binding affinity values of − 5.3 to − 5.2 kcal/mol, respectively, against human peroxiredoxin 5. These values are higher than that of ascorbic acid (− 4.9 kcal/mol), in good agreement with the experimental findings. In silico cytotoxicity predictions showed that the synthesized compounds Lethal Dose (LD50) value are class three (50 ≤ LD50 ≤ 300), indicating that the compounds could be categorized under toxic class. Density functional theory calculations showed that the synthesized compounds have small band gap energies ranging from 1.795 to 2.242 eV, demonstrating that the compounds have good reactivities. Conclusions The synthesized compounds showed moderate to high antibacterial and antioxidant activities. The in vitro antibacterial activity and molecular docking analysis showed that compound 11 is a promising antibacterial therapeutics agent against E. coli, whereas compounds 7 and 9 were found to be promising antioxidant agents. Moreover, the green synthesis approach using ZnO nanoparticles as catalyst was found to be a very efficient method to synthesize biologically active compounds compared to the conventional method.

show abstract

Design and synthesis of three Fe(III) mixed-ligand complexes: Exploration of their biological and phenoxazinone synthase-like activities

Cited by 60 publications

References 54 publications

Pharmacokinetics and drug-likeness of antidiabetic flavonoids: Molecular docking and DFT study

Pharmacokinetics and drug-likeness of antidiabetic flavonoids: Molecular docking and DFT study

Synthesis, structural elucidation, and density functional theory investigation of new mononuclear Fe(III), Ni(II), and Cu(II) mixed‐ligand complexes: Biological and catalase mimicking activity exploration

Synthesis, antibacterial and antioxidant activities of Thiazole-based Schiff base derivatives: a combined experimental and computational study

Contact Info

Product

Resources

About