Scutellarein in organic solvents: changes in spectroscopic properties caused by solute-solvent interactions

Ushakou, Dzmitryi V.; Wróblewski, Tomasz

doi:10.1016/j.saa.2022.121027

Cited by 4 publications

(2 citation statements)

References 50 publications

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“…B3LYP functional in combination with Pople style basis sets represents a suitable method to calculate the properties of polyphenolic compounds, capable of producing reliable results at a reasonable computational cost 37 . For example, such computational protocol has been successfully applied to reproduce the spectroscopic properties of scutellarein, 38 or Cu(II) complexes with luteolin, 39 apigenin, 39 chrysin, 40 and quercetin 40 . In addition, B3LYP functional is often used to calculate the thermodynamic properties of various flavonoids 12,13 .…”

Section: Methodsmentioning

confidence: 99%

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: Methodsmentioning

confidence: 99%

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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“…The following example is tautomerization in scutellarein. The recent study has shown the possibility of ESIPT in scutellarein [ 48 ]. The structure of this flavone also contains three adjacent hydroxyl groups, that allows to consider a hypothetical ESIDPT process.…”

Section: Examples Of Compounds With Multiple Adjacent Hydroxyl Groupsmentioning

confidence: 99%

Stepwise Excited-state Double Proton Transfer and Fluorescence Decay Analysis

Wróblewski

Ushakou

2022

J Fluoresc

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This work considers excited state intramolecular proton transfers (ESIPT) occurred in multiple hydroxyl-containing compounds with one proton transfer site in the normal form. If several hydroxyl groups are located close to each other in a molecule, then the ESIPT process can lead to the next one. A proton donor site in the first ESIPT will be a proton acceptor during the second reaction. Therefore, a number of consecutive excited state proton transfers can occur. This work deals with the case of two successive proton transfers occurred in the molecular system. Such process is called as a stepwise excited state intramolecular double proton transfer (stepwise ESIDPT). It leads to the formation of two molecular tautomers. Therefore, fluorescence of such compounds can contain different emission bands correspond to emission of normal form and two tautomers. In this work, a rigorous analysis of fluorescence decay kinetics has been made using the model with three species, including a normal molecular form and two tautomers. The work presents theoretical framework of fluorescence decay analysis of ESIDPT process taking into account three species emission. Theoretically, the stepwise proton transfers can be consisted of more than two ESIPT reactions. It depends on molecular structure and number of involved hydroxyl groups. Here, a formal analysis of fluorescence decay kinetics has been made in the case of a stepwise process consisting of two proton transfers. Moreover, the quantum-chemical calculations have been performed in the case of scutellarein. It is a multiple hydroxyl-containing flavone and, therefore, it can be applied as a model molecule to study stepwise intramolecular proton transfers. The hypothetical scheme of ESIDPT has been proposed for this compound. Graphical abstract

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Insights into the complexation and oxidation of quercetin and luteolin in aqueous solutions in presence of selected metal cations

Malacaria

Bijlsma

Hilgers

et al. 2023

Journal of Molecular Liquids

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Scutellarein in organic solvents: changes in spectroscopic properties caused by solute-solvent interactions

Cited by 4 publications

References 50 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

Stepwise Excited-state Double Proton Transfer and Fluorescence Decay Analysis

Insights into the complexation and oxidation of quercetin and luteolin in aqueous solutions in presence of selected metal cations

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