[Cu(dipicolinoylamide)(NO3)(H2O)] as anti-COVID-19 and antibacterial drug candidate: Design, synthesis, crystal structure, DFT and molecular docking

Abdel‐Rahman, Laila H.; Basha, Maram T.; Al–Farhan, Badriah Saad; Shehata, Mohamed; Mohamed, Shaaban K.; Ramli, Youssef

doi:10.1016/j.molstruc.2021.131348

Cited by 17 publications

(9 citation statements)

References 28 publications

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“…The graphical representation of the molecular docking, that is, drugs-receptor H. bond interactions, receptor side surface H. bond interactions, and 2D-ligand-receptor H. bond interactions, was shown for all of the studied materials [64,65] (Figure 6a-c). Compared with the other copper complexes reported in the literature, [66] these complexes showed more negative binding energies, which could be attributed to the electron-withdrawing groups of the aldehyde and BTZ moieties.…”

Section: Molecular Docking With Sars-cov-2 Virus (Covid-19 Disease) A...mentioning

confidence: 56%

Synthesis and characterization of two new mixed‐ligand Cu(II) complexes of a tridentate NN'O type Schiff base ligand and N‐donor heterocyclic co‐ligands: In vitro anticancer assay, DNA/human leukemia/COVID‐19 molecular docking studies, and pharmacophore modeling

Ghasemi

Behzad

Khaleghian

et al. 2022

Applied Organom Chemis

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Two new mixed-ligand complexes with general formula [Cu(SB)(L')]ClO 4(1 and 2) were synthesized and characterized by different spectroscopic and analytical techniques including Fourier transform infrared (FT-IR) and UV-Vis spectroscopy and elemental analyses. The SB ligand is an unsymmetrical tridentate NN'O type Schiff base ligand that was derived from the condensation of 1,2-ethylenediamine and 5-bromo-2-hydroxy-3-nitrobenzaldehyde. The L' ligand is pyridine in (1) and 2,2 0 -dimethyl-4,4 0 -bithiazole (BTZ) in (2). Crystal structure of (2) was also obtained. The two complexes were used as anticancer agents against leukemia cancer cell line HL-60 and showed considerable anticancer activity. The anticancer activity of these complexes was comparable with the standard drug 5-fluorouracil (5-FU). Molecular docking and pharmacophore studies were also performed on DNA (PDB:1BNA) and leukemia inhibitor factor (LIF) (PDB:1EMR) to further investigate the anticancer and anti-COVID activity of these complexes. The molecular docking results against DNA revealed that (1) preferentially binds to the major groove of DNA receptor whereas (2) binds to the minor groove. Complex (2) performed better with 1EMR. The experimental and theoretical results showed good correlation. Molecular docking and pharmacophore studies were also applied to study the interactions between the synthesized complexes and SARS-CoV-2 virus receptor protein (PDB ID:6LU7). The results revealed that complex (2) had better interaction than (1), the free ligands (SB and BTZ), and the standard drug favipiravir.anticancer, COVID-19, mixed-ligand, molecular docking, unsymmetrical Schiff base CCDC number 2089608 contains the supplementary crystallographic data for complex (2). These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif (supporting information).

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Section: Molecular Docking With Sars-cov-2 Virus (Covid-19 Disease) A...mentioning

confidence: 56%

Synthesis and characterization of two new mixed‐ligand Cu(II) complexes of a tridentate NN'O type Schiff base ligand and N‐donor heterocyclic co‐ligands: In vitro anticancer assay, DNA/human leukemia/COVID‐19 molecular docking studies, and pharmacophore modeling

Ghasemi

Behzad

Khaleghian

et al. 2022

Applied Organom Chemis

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“…[30,44] As a result, the pH range for various implementations of the new metal chelates should be between 4 and 11. [45]…”

Section: Stability Range Of the Complexesmentioning

confidence: 99%

Synthesis, spectroscopic, DFT calculations, antimicrobial, cytotoxicity, and DNA binding studies of novel Cu (II), Ni (II), Zn (II), and VO (II) Schiff base complexes based on ibuprofen

Abdel‐Rahman

Abdel‐Mawgoud

Mohamed

et al. 2022

Applied Organom Chemis

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The ibuprofen Schiff base ligand (HL) [HL=2-(4-Isobutyl-phenyl)-propionic acid (3-hydroxy-naphthalen-2-ylmethylene)-hydrazide] and its Cu (II), Ni (II), Zn (II), and VO (II) chelates were synthesized and characterized. The spectral data revealed that the Schiff base ligand HL coordinated to Cu (II), Ni (II), Zn (II), and VO (II) via azomethine nitrogen and phenolic oxygen. NiL and CuL have square planar geometry, ZnL has octahedral geometry, and VOL has square pyramidal geometry. Density functional calculations (DFT) were performed to examine the molecular geometry. The results of continuous variation and molar ratio methods supported the ratio of (M:L) to be (1:1). The antimicrobial activity of the new Ibuprofen Schiff base ligand and its metal complexes was tested in vitro against bacterial pathogens and fungi. The results revealed that the antimicrobial efficacy follows the order: CuL is the highly inhibitor complex compared with ketoconazole and gentamicin as reference drugs. The in vitro cytotoxic activity of the new ligand and its complexes was also investigated against Hep-G2, MCF-7, and HCT-116 cell lines. The results showed again that CuL is the highest active agent compared with Vinblastine drug. The CT-DNA binding ability of the studied complexes was evaluated by absorption spectroscopic titrations and gel electrophoresis. The results showed that the complexes have good binding propensity, and their binding constant values were from 3.1 Â 10 5 to 6.1 Â 10 5 M À1 .

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“…The theoretical study of the prepared Schiff base ligand and Cu(II) complex were performed on the Gaussian09 package 25 at the B3LYP level of theory. The computations were conducted via 6–311G++(d,p) 26 basis set for H 2 L atoms and LANL2DZ 27 basis set with effective core potential (ECP) for copper atoms. Theoretical IR spectra were computed at the same level of the theory to confirm the absence of imaginary frequencies as shown in Figures S8 and S9.…”

Section: Methodsmentioning

confidence: 99%

Facile synthesis and grafting of N₂O₂‐Cu(II) Schiff base complex onto graphene oxide surface: Aspects of its antimicrobial, anticancer, antiCOVID‐19 and photodegradation of methylene blue

Abdel‐Rahman,

Shehata,

Ahmed

et al. 2024

Vietnam Journal of Chemistry

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In this study, a facile synthesis and grafting method is reported for tetradentate Cu(II) Schiff base complex onto the surface of graphene oxide (GO). The Schiff base Cu‐complex was synthesized through the condensation reaction between 2,3‐diamino pyridine and 2‐hydroxy‐1‐naphthaldehyde, followed by the addition of Cu(II) ion to afford N2O2‐Cu(II) complex. The GO was prepared through a modified Hummers’ method and characterized using various spectroscopic and microscopic techniques. The Schiff base Cu‐complex was then grafted onto the surface of GO via a simple solution‐phase reaction, resulting in the formation of N2O2‐Cu(II) Schiff base/GO composite. The fabricated composite was characterized using FTIR spectroscopy, UV–vis, X‐ray diffraction (XRD), and scanning electron microscopy (SEM). Importantly, the prepared N2O2‐Cu(II) Schiff base complex exhibited excellent DNA interaction as well as efficient antimicrobial and anticancer activities. Additionally, it demonstrated potent anticancer activity against hepatocellular carcinoma cells (HepG‐2), and colon cancer cells (HCT‐116) and exhibited promising activity against the COVID‐19 receptor (PDB ID: 6LU7) along with the human DNA receptor (PDB ID: 1BNA). Furthermore, this fabricated heterogeneous catalyst showed enhanced photodegradation of MB with ≈92% conversion and four times recyclability. The overall results suggest that the Cu(II) Schiff base/GO composite has potential applications in various medical and environmental fields, including photodegradation/elimination of harmful organic dyes for water treatment applications.

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[Cu(dipicolinoylamide)(NO3)(H2O)] as anti-COVID-19 and antibacterial drug candidate: Design, synthesis, crystal structure, DFT and molecular docking

Cited by 17 publications

References 28 publications

Synthesis and characterization of two new mixed‐ligand Cu(II) complexes of a tridentate NN'O type Schiff base ligand and N‐donor heterocyclic co‐ligands: In vitro anticancer assay, DNA/human leukemia/COVID‐19 molecular docking studies, and pharmacophore modeling

Synthesis and characterization of two new mixed‐ligand Cu(II) complexes of a tridentate NN'O type Schiff base ligand and N‐donor heterocyclic co‐ligands: In vitro anticancer assay, DNA/human leukemia/COVID‐19 molecular docking studies, and pharmacophore modeling

Synthesis, spectroscopic, DFT calculations, antimicrobial, cytotoxicity, and DNA binding studies of novel Cu (II), Ni (II), Zn (II), and VO (II) Schiff base complexes based on ibuprofen

Facile synthesis and grafting of N₂O₂‐Cu(II) Schiff base complex onto graphene oxide surface: Aspects of its antimicrobial, anticancer, antiCOVID‐19 and photodegradation of methylene blue

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[Cu(dipicolinoylamide)(NO3)(H2O)] as anti-COVID-19 and antibacterial drug candidate: Design, synthesis, crystal structure, DFT and molecular docking

Cited by 17 publications

References 28 publications

Synthesis and characterization of two new mixed‐ligand Cu(II) complexes of a tridentate NN'O type Schiff base ligand and N‐donor heterocyclic co‐ligands: In vitro anticancer assay, DNA/human leukemia/COVID‐19 molecular docking studies, and pharmacophore modeling

Synthesis and characterization of two new mixed‐ligand Cu(II) complexes of a tridentate NN'O type Schiff base ligand and N‐donor heterocyclic co‐ligands: In vitro anticancer assay, DNA/human leukemia/COVID‐19 molecular docking studies, and pharmacophore modeling

Synthesis, spectroscopic, DFT calculations, antimicrobial, cytotoxicity, and DNA binding studies of novel Cu (II), Ni (II), Zn (II), and VO (II) Schiff base complexes based on ibuprofen

Facile synthesis and grafting of N2O2‐Cu(II) Schiff base complex onto graphene oxide surface: Aspects of its antimicrobial, anticancer, antiCOVID‐19 and photodegradation of methylene blue

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Facile synthesis and grafting of N₂O₂‐Cu(II) Schiff base complex onto graphene oxide surface: Aspects of its antimicrobial, anticancer, antiCOVID‐19 and photodegradation of methylene blue