A DFT Study of Structural and Bonding Properties of Complexes Obtained from First-Row Transition Metal Chelation by 3-Alkyl-4-phenylacetylamino-4,5-dihydro-1H-1,2,4-triazol-5-one and Its Derivatives

Nono, Hubert Jean; Mama, Désiré Bikele; Ghogomu, Julius Numbonui; Younang, Elie

doi:10.1155/2017/5237865

Cited by 15 publications

(6 citation statements)

References 39 publications

(41 reference statements)

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“…The energy value of HOMO is lower than LUMO for MP, indicating the ability of the MP molecule to donate electrons to the metal ion and to accept electrons as a charge transfer. [ 31 ]…”

Section: Resultsmentioning

confidence: 99%

Transition metal complexes of 6‐mercaptopurine: Characterization, Theoretical calculation, DNA‐Binding, molecular docking, and anticancer activity

Sharfalddin

Emwas

Jaremko

et al. 2020

Applied Organom Chemis

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6‐mercaptopurine (6‐MP) is used for treating various cancers and autoimmune disorders. A few examples of transition metal complexes of 6‐MP have been shown to enhance its anticancer activity, but many remain untested. We isolated five highly stable and colored metal complexes of 6‐MP and confirmed their structures by elemental analysis, spectral, and thermal techniques. Infrared (IR) spectra revealed that 6‐MP is a bidentate ligand that interacts through sulfur and pyrimidine nitrogen in a 1:2 (M:L) molar ratio. The magnetic susceptibility and electron paramagnetic resonance (EPR) spectra for the Cu(II) complex revealed an octahedral arrangement around the metal ion with strong covalent bonding. The fully optimized geometries of the metal structures obtained using density function theory (DFT)/B3LYP calculations were used to verify the structural and biological features. DNA titration revealed that the octahedral Cu(II) complex has a critical binding constant value of Kb = 8 × 105. Docking studies using three different cancer protein receptors were used to predict the biological applications of the synthesized drug‐metal complexes. Finally, cytotoxicity assays against a myeloma cancer cell line (MM) and a colon cancer cell line (Caco‐2) revealed favorable anticancer activity for the copper complex, exceeding that of the gold‐standard chemotherapeutic cisplatin.

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“…The energy value of HOMO is lower than LUMO for MP, indicating the ability of the MP molecule to donate electrons to the metal ion and to accept electrons as a charge transfer. [ 31 ]…”

Section: Resultsmentioning

confidence: 99%

Transition metal complexes of 6‐mercaptopurine: Characterization, Theoretical calculation, DNA‐Binding, molecular docking, and anticancer activity

Sharfalddin

Emwas

Jaremko

et al. 2020

Applied Organom Chemis

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“…It is known that high eigenvalue of HOMO and small band gap energy between HOMO and LUMO of a compound are associated with its high antioxidant activity [ 72 ]. Having this in mind, we analyzed the quantum mechanical descriptors of all the compounds.…”

Section: Resultsmentioning

confidence: 99%

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

et al. 2021

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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.

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“…Compared to optimizations with a computationally intensive polarizable continuum model in DFT considering the solvent effect, the gas-phase calculation has been shown to be a fast and reasonable alternative for obtaining a good description of bond lengths and angles for typical biological molecules. The hybrid GGA (generalized gradient approximation) exchange–correlation functional, B3LYP (Becke’s three parameter Lee–Yang–Parr) was employed, along with the LANL2DZ (Los Alamos effective-core potential) basis set for the Zn(II) metal and the 6-31G(d,p) basis set for the hydrogen, carbon, and oxygen atoms of the complex. , The B3LYP functional has been shown to provide a reliable description of the electronic structures of biomolecules interacting with transition metals . To reduce the computational cost associated with geometry optimization of Zn(II)–EGCG complexes, we replaced the bulky catechin group with the −CH 3 group, as shown in Figure a,b.…”

Section: Methodsmentioning

confidence: 99%

Zinc–Epigallocatechin-3-gallate Network-Coated Nanocomposites against the Pathogenesis of Amyloid-Beta

Andrikopoulos

Nandakumar

et al. 2023

ACS Appl. Mater. Interfaces

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The aggregation of amyloid beta (Aβ) is a hallmark of Alzheimer’s disease (AD), a major cause of dementia and an unmet challenge in modern medicine. In this study, we constructed a biocompatible metal–phenolic network (MPN) comprising a polyphenol epigallocatechin gallate (EGCG) scaffold coordinated by physiological Zn(II). Upon adsorption onto gold nanoparticles, the MPN@AuNP nanoconstruct elicited a remarkable potency against the amyloid aggregation and toxicity of Aβ in vitro. The superior performance of MPN@AuNP over EGCG@AuNP was attributed to the porosity and hence larger surface area of the MPN in comparison with that of EGCG alone. The atomic detail of Zn(II)–EGCG coordination was unraveled by density functional theory calculations and the structure and dynamics of Aβ aggregation modulated by the MPN were further examined by discrete molecular dynamics simulations. As MPN@AuNP also displayed a robust capacity to cross a blood–brain barrier model through the paracellular pathway, and given the EGCG’s function as an anti-amyloidosis and antioxidation agent, this MPN-based strategy may find application in regulating the broad AD pathology beyond protein aggregation inhibition.

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A DFT Study of Structural and Bonding Properties of Complexes Obtained from First-Row Transition Metal Chelation by 3-Alkyl-4-phenylacetylamino-4,5-dihydro-1H-1,2,4-triazol-5-one and Its Derivatives

Cited by 15 publications

References 39 publications

Transition metal complexes of 6‐mercaptopurine: Characterization, Theoretical calculation, DNA‐Binding, molecular docking, and anticancer activity

Transition metal complexes of 6‐mercaptopurine: Characterization, Theoretical calculation, DNA‐Binding, molecular docking, and anticancer activity

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

Zinc–Epigallocatechin-3-gallate Network-Coated Nanocomposites against the Pathogenesis of Amyloid-Beta

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