Cu(II) complexes of flavonoids in solution: Impact of the Cu(II) ion on the antioxidant and DNA-intercalating properties

Šimunková, Miriama; Biela, Monika; Štekláč, Marek; Hlinčík, Andrej; Klein, Erik; Malček, Michal

doi:10.1016/j.molliq.2022.119230

Cited by 6 publications

(12 citation statements)

References 56 publications

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“…On the contrary, the coordination of Cu(II) ion via the Cu1 site is exclusively preferred in the case of scutellarein (BP ratio 100%; see Table 4). Overall, these results are in agreement with the previous reports about the Cu(II) binding site preference in different flavonoids, such as luteolin, 39 quercetin, 40,75 kaempferol, 51,52 or genistein. 76 Calculated Δ r H values of Cu(II) binding in 1:1 ratio are similar for both FLs under study, being around À400 kJ mol À1 .…”

Section: Dft Calculations-binding Modes and Thermodynamics Of Cu(ii)-...supporting

confidence: 93%

“…The charge distribution was selected based on our previous publications, in which we have explored the effect of various charge distributions on the outcomes of molecular docking. 51,52 The unliganded structure of the calf thymus DNA (CT-DNA) dodecamer d (CGCGAATTCGCG) (PDB ID: 1bna) 53 was downloaded from the RCSB database 54 to serve as targets for molecular docking studies. The binding potential toward DNA was calculated in grid box encapsulating whole DNA strand, centered at (15, 21, 9) Å with the dimensions of 75 Â 75 Â 126 and a resolution of 0.325 Å.…”

Section: Molecular Docking Studiesmentioning

confidence: 99%

“…This setup was selected to ensure compatibility with our previous works detailing the binding of flavonoid complexes to CT-DNA. 51,52 The predicted hydrogen bond pattern was analyzed with AutoDock4.2.6 suite utilities. The binding constants at a temperature consistent with the experiment (T = 298.15 K) were calculated from the free binding energies as follows:…”

Section: Molecular Docking Studiesmentioning

confidence: 99%

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The effect of Cu(II) ion on antioxidant and DNA‐binding mechanism of baicalein and scutellarein: Spectroscopic, theoretical, and molecular docking study

Malček Šimunková,

Štekláč,

Raptová

et al. 2024

Applied Organom Chemis

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Flavonoids are a group of polyphenolic compounds known to possess good radical scavenging activity. It was also shown that their anti/prooxidant properties are strongly structure‐dependent and can be modified by metal ion binding. The structural parameters also appear to be key factors during their DNA‐binding abilities. This work deals with spectroscopic and theoretical studies of two flavonoids, baicalein and scutellarein, alone, and in the presence of redox‐active metal ion Cu(II). Cu(II) is the catalytic active ion in Fenton‐like reactions and can enhance the production of reactive oxygen species or, when bound to the flavonoid, influence its antioxidant potential. UV–Vis spectroscopy showed that the electronic properties of the parent flavonoids are changed following the CuCl2 addition. Job's plot method revealed the 1:1 binding mode of interaction in DMSO and DMSO/PBS solvent. The ABTS•+ assay showed only a negligible effect of Cu(II) presence on the antioxidant properties of baicalein and scutellarein. The mix of the natural reductant, glutathione, with flavonoids showed a synergistic effect in ABTS•+ inhibition; however, this effect was suppressed by the presence of Cu(II). Absorption titration and molecular docking studies showed an effective DNA binding of both flavonoids that is further enhanced by the presence of Cu(II). DFT calculations were carried out to identify the most energetically stable Cu(II)–flavonoid structures as well as to determine the ability of their hydroxyl groups to undergo homolytic or heterolytic cleavage.

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Section: Dft Calculations-binding Modes and Thermodynamics Of Cu(ii)-...supporting

confidence: 93%

Section: Molecular Docking Studiesmentioning

confidence: 99%

Section: Molecular Docking Studiesmentioning

confidence: 99%

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The effect of Cu(II) ion on antioxidant and DNA‐binding mechanism of baicalein and scutellarein: Spectroscopic, theoretical, and molecular docking study

Malček Šimunková,

Štekláč,

Raptová

et al. 2024

Applied Organom Chemis

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“…Similarly, C:G interactions are

kcal mol −1 in MM against

kcal mol −1 in PA. The lack of screening may be a problem for nucleotide interactions beyond those of pairs in a double-helix [ 97 ], as occur in packed DNA, in non-canonical or transitional structures [ 98 , 99 , 100 , 101 ], or in complexes with ligands [ 102 , 103 , 104 ].…”

Section: Resultsmentioning

confidence: 99%

The Importance of Charge Transfer and Solvent Screening in the Interactions of Backbones and Functional Groups in Amino Acid Residues and Nucleotides

Sládek

Fedorov

2022

IJMS

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Quantum mechanical (QM) calculations at the level of density-functional tight-binding are applied to a protein–DNA complex (PDB: 2o8b) consisting of 3763 atoms, averaging 100 snapshots from molecular dynamics simulations. A detailed comparison of QM and force field (Amber) results is presented. It is shown that, when solvent screening is taken into account, the contributions of the backbones are small, and the binding of nucleotides in the double helix is governed by the base–base interactions. On the other hand, the backbones can make a substantial contribution to the binding of amino acid residues to nucleotides and other residues. The effect of charge transfer on the interactions is also analyzed, revealing that the actual charge of nucleotides and amino acid residues can differ by as much as 6 and 8% from the formal integer charge, respectively. The effect of interactions on topological models (protein -residue networks) is elucidated.

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“…Analysis of organic components in Huangqin aqueous extracts with the potential to form metal complexes. Research has indicated that organic components in traditional medicinal plants can form metal complexes with trace metal ions, and these metal complexes exhibit biological activities that differ from those of ligands and metal ions, [29][30][31][32][33] resulting in considerable interest among scientists. However, as a consequence of the variety and low content of metal complexes in medicinal plants, as well as the difficulty of their separation and purification using existing instruments and techniques, this type of active component has not been reported in medicinal plant extracts.…”

Section: Discovery Of Antibacterial Metal Complexes In Aqueous Extrac...mentioning

confidence: 99%

Discovery of metal complexes with antibacterial properties in aqueous extracts of Radix scutellariae and a study of the antibacterial properties of the baicalin–manganese complex

Liu

Jiang

Peng

et al. 2023

Inorg. Chem. Front.

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Cu(II) complexes of flavonoids in solution: Impact of the Cu(II) ion on the antioxidant and DNA-intercalating properties

Cited by 6 publications

References 56 publications

The effect of Cu(II) ion on antioxidant and DNA‐binding mechanism of baicalein and scutellarein: Spectroscopic, theoretical, and molecular docking study

The effect of Cu(II) ion on antioxidant and DNA‐binding mechanism of baicalein and scutellarein: Spectroscopic, theoretical, and molecular docking study

The Importance of Charge Transfer and Solvent Screening in the Interactions of Backbones and Functional Groups in Amino Acid Residues and Nucleotides

Discovery of metal complexes with antibacterial properties in aqueous extracts of Radix scutellariae and a study of the antibacterial properties of the baicalin–manganese complex

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