Evaluating the in vitro antidiabetic, antibacterial and antioxidant properties of copper(II) Schiff base complexes: An experimental and computational studies

Yusuf, Tunde L.; Waziri, Ibrahim; Olofinsan, Kolawole A.; Akintemi, Eric O.; Hosten, Eric C.; Muller, Alfred J.

doi:10.1016/j.molliq.2023.122845

Cited by 15 publications

(5 citation statements)

References 48 publications

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“…It could be concluded that in the DPPH assay, the coordination of ligands to the copper(II) metal center appears to be beneficial for antiradical potency as was previously reported [ 88 , 89 , 90 ]. In general, no similar correlation was found for complexes C1 – 4 compared with their ligands L1 – 4 in the ABTS analysis.…”

Section: Resultssupporting

confidence: 55%

Copper(II) Complexes with 1-(Isoquinolin-3-yl)heteroalkyl-2-ones: Synthesis, Structure and Evaluation of Anticancer, Antimicrobial and Antioxidant Potential

Balewski,

Plech,

Korona-Głowniak

et al. 2023

IJMS

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Four copper(II) complexes, C1–4, derived from 1-(isoquinolin-3-yl)heteroalkyl-2-one ligands L1–4 were synthesized and characterized using an elemental analysis, IR spectroscopic data as well as single crystal X-ray diffraction data for complex C1. The stability of complexes C1–4 under conditions mimicking the physiological environment was estimated using UV-Vis spectrophotometry. The antiproliferative activity of both ligands L1–4 and copper(II) compounds C1–4 were evaluated using an MTT assay on four human cancer cell lines, A375 (melanoma), HepG2 (hepatoma), LS-180 (colon cancer) and T98G (glioblastoma), and a non-cancerous cell line, CCD-1059Sk (human normal skin fibroblasts). Complexes C1–4 showed greater potency against HepG2, LS180 and T98G cancer cell lines than etoposide (IC50 = 5.04–14.89 μg/mL vs. IC50 = 43.21–>100 μg/mL), while free ligands L1–4 remained inactive in all cell lines. The prominent copper(II) compound C2 appeared to be more selective towards cancer cells compared with normal cells than compounds C1, C3 and C4. The treatment of HepG2 and T98G cells with complex C2 resulted in sub-G1 and G2/M cell cycle arrest, respectively, which was accompanied by DNA degradation. Moreover, the non-cytotoxic doses of C2 synergistically enhanced the cytotoxic effects of chemotherapeutic drugs, including etoposide, 5-fluorouracil and temozolomide, in HepG2 and T98G cells. The antimicrobial activities of ligands L2–4 and their copper(II) complexes C2–4 were evaluated using different types of Gram-positive bacteria, Gram-negative bacteria and yeast species. No correlation was found between the results of the antiproliferative and antimicrobial experiments. The antioxidant activities of all compounds were determined using the DPPH and ABTS radical scavenging methods. Antiradical tests revealed that among the investigated compounds, copper(II) complex C4 possessed the strongest antioxidant properties. Finally, the ADME technique was used to determine the physicochemical and drug-likeness properties of the obtained complexes.

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Section: Resultssupporting

confidence: 55%

Copper(II) Complexes with 1-(Isoquinolin-3-yl)heteroalkyl-2-ones: Synthesis, Structure and Evaluation of Anticancer, Antimicrobial and Antioxidant Potential

Balewski,

Plech,

Korona-Głowniak

et al. 2023

IJMS

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“…The crystal structures of the proteins corresponding to the experimental biological assays, as considered in a previous study by Yusuf and co‐workers, [32] were retrieved from the Research Collaboratory for Structural Bioinformatics (RCSB) website (https://www.rcsb.org/). The chosen crystal structures and their macromolecular information are contained in Table 2.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Therapeutic Potential of selected Schiff Bases: In vitro Antibacterial, Antioxidant, Antidiabetic, and Computational Studies

Adeleke,

Oladipo,

Luckay

et al. 2024

ChemistrySelect

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In this study, three Schiff base compounds, (E)‐N‐(4‐bromophenyl)‐1‐(2‐nitrophenyl)methanimine (L1), (E)‐2‐((mesitylimino)methyl)phenol (L2), and (E)‐N‐(4‐bromophenyl)‐1‐(pyridin‐2‐yl)methanimine (L3), were synthesized and characterized by various spectroscopic techniques. The antibacterial activity of the compounds was evaluated against Gram‐positive and Gram‐negative bacteria, with L3 demonstrating the most significant activity. The compounds were also evaluated for their antioxidant activity using DPPH, FRAP, and NO scavenging assays. While the compounds exhibited concentration‐dependent scavenging of free radicals, their activity was not as significant as that of the reference, Trolox. Furthermore, L1–L3 were tested for their α‐amylase and α‐glucosidase inhibitory activity, with L1 showing the highest inhibitory activity among the three compounds. The DFT study showed that L1 is the most chemically reactive among the three compounds, having the lowest energy band gap value of 3.82 eV in acetonitrile, the experimental solvent. Molecular docking predicted that L1 and L2 have very strong inhibition equivalents to the standard drugs against bacteria and diabetes. All the compounds showed stronger inhibition against α‐glucosidase than acarbose, while only L1 and L2 exhibited stronger inhibition against α‐amylase than acarbose. It can be deduced that the theoretical studies corroborate well with the experimental, and compounds with the electron‐withdrawing group displayed better medicinal properties than their electron‐donating counterparts.

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“…Subsequently, AutoDock tools [ 46 ] facilitated the molecular docking of all designed compounds, enabling an in-depth exploration of potential interactions and the determination of binding affinities within the active site of the receptor. The docking simulation was conducted through a total of 9 runs, and the complex resulting from the run with the lowest binding affinity, corresponding to an RMSD of 0, was selected and subjected to analysis [ 47 ]. The calculated Root-Mean-Squared Deviation (RMSD) value of 0.217 Å (below 2 Å) indicates a minimal deviation between the initial ligand and the docked ligand ( Figure 9 ).…”

Section: Methodsmentioning

confidence: 99%

“…complex resulting from the run with the lowest binding affinity, corresponding to an RMSD of 0, was selected and subjected to analysis [47]. The calculated Root-Mean-Squared Deviation (RMSD) value of 0.217 Å (below 2 Å) indicates a minimal deviation between the initial ligand and the docked ligand (Figure 9).…”

Section: Molecular Dockingmentioning

confidence: 99%

Integrative Approach for Designing Novel Triazole Derivatives as α-Glucosidase Inhibitors: QSAR, Molecular Docking, ADMET, and Molecular Dynamics Investigations

Abchir,

Khedraoui,

Nour

et al. 2024

Pharmaceuticals

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In response to the increasing prevalence of diabetes mellitus and the limitations associated with the current treatments, there is a growing need to develop novel medications for this disease. This study is focused on creating new compounds that exhibit a strong inhibition of alpha-glucosidase, which is a pivotal enzyme in diabetes control. A set of 33 triazole derivatives underwent an extensive QSAR analysis, aiming to identify the key factors influencing their inhibitory activity against α-glucosidase. Using the multiple linear regression (MLR) model, seven promising compounds were designed as potential drugs. Molecular docking and dynamics simulations were employed to shed light on the mode of interaction between the ligands and the target, and the stability of the obtained complexes. Furthermore, the pharmacokinetic properties of the designed compounds were assessed to predict their behavior in the human body. The binding free energy was also calculated using MMGBSA method and revealed favorable thermodynamic properties. The results highlighted three novel compounds with high biological activity, strong binding affinity to the target enzyme, and suitability for oral administration. These results offer interesting prospects for the development of effective and well-tolerated medications against diabetes mellitus.

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Evaluating the in vitro antidiabetic, antibacterial and antioxidant properties of copper(II) Schiff base complexes: An experimental and computational studies

Cited by 15 publications

References 48 publications

Copper(II) Complexes with 1-(Isoquinolin-3-yl)heteroalkyl-2-ones: Synthesis, Structure and Evaluation of Anticancer, Antimicrobial and Antioxidant Potential

Copper(II) Complexes with 1-(Isoquinolin-3-yl)heteroalkyl-2-ones: Synthesis, Structure and Evaluation of Anticancer, Antimicrobial and Antioxidant Potential

Synthesis and Therapeutic Potential of selected Schiff Bases: In vitro Antibacterial, Antioxidant, Antidiabetic, and Computational Studies

Integrative Approach for Designing Novel Triazole Derivatives as α-Glucosidase Inhibitors: QSAR, Molecular Docking, ADMET, and Molecular Dynamics Investigations

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