Enhanced electrochemical determination of quercetin in a choline chloride-based ionic liquid

Guo, Meiling; Wang, Zhangxu; Wang, Zixin; Zhang, Lin

doi:10.1039/d2ay01972h

Cited by 7 publications

(2 citation statements)

References 52 publications

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“…Cyclic voltammetry is commonly used to characterize the reduction ability and electrochemical behavior of phenolic antioxidants [ 40 , 41 ]. Generally, there is a correlation between antioxidant and pro-oxidant activity and oxidation potential.…”

Section: Resultsmentioning

confidence: 99%

Hybrids of Sterically Hindered Phenols and Diaryl Ureas: Synthesis, Switch from Antioxidant Activity to ROS Generation and Induction of Apoptosis

Gibadullina,

Neganova,

Aleksandrova

et al. 2023

IJMS

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The utility of sterically hindered phenols (SHPs) in drug design is based on their chameleonic ability to switch from an antioxidant that can protect healthy tissues to highly cytotoxic species that can target tumor cells. This work explores the biological activity of a family of 45 new hybrid molecules that combine SHPs equipped with an activating phosphonate moiety at the benzylic position with additional urea/thiourea fragments. The target compounds were synthesized by reaction of iso(thio)cyanates with C-arylphosphorylated phenols containing pendant 2,6-diaminopyridine and 1,3-diaminobenzene moieties. The SHP/urea hybrids display cytotoxic activity against a number of tumor lines. Mechanistic studies confirm the paradoxical nature of these substances which combine pronounced antioxidant properties in radical trapping assays with increased reactive oxygen species generation in tumor cells. Moreover, the most cytotoxic compounds inhibited the process of glycolysis in SH-SY5Y cells and caused pronounced dissipation of the mitochondrial membrane of isolated rat liver mitochondria. Molecular docking of the most active compounds identified the activator allosteric center of pyruvate kinase M2 as one of the possible targets. For the most promising compounds, 11b and 17b, this combination of properties results in the ability to induce apoptosis in HuTu 80 cells along the intrinsic mitochondrial pathway. Cyclic voltammetry studies reveal complex redox behavior which can be simplified by addition of a large excess of acid that can protect some of the oxidizable groups by protonations. Interestingly, the re-reduction behavior of the oxidized species shows considerable variations, indicating different degrees of reversibility. Such reversibility (or quasi-reversibility) suggests that the shift of the phenol-quinone equilibrium toward the original phenol at the lower pH may be associated with lower cytotoxicity.

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Section: Resultsmentioning

confidence: 99%

Hybrids of Sterically Hindered Phenols and Diaryl Ureas: Synthesis, Switch from Antioxidant Activity to ROS Generation and Induction of Apoptosis

Gibadullina,

Neganova,

Aleksandrova

et al. 2023

IJMS

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show abstract

“…The detection of polyphenols relies on redox reactions involving these structures, which can be monitored by electrochemical techniques such as cyclic voltammetry. [18][19][20] For example, the detection of phenol and catechol at low concentrations (10 −8 M) has been achieved using nanocarbon electrodes. 21 Simultaneously detection of dihydroxybenzene (DHB) isomers were also achieved by electrochemical methods.…”

mentioning

confidence: 99%

Structure-dependent detection of polyphenols using crown ether-immobilized gold nanoparticles

Yamaki,

Seo,

Hatano

et al. 2024

RSC Adv.

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Perspectives for the use of deep eutectic solvents in the preparation of electrochemical sensors and biosensors

Brett

2024

Current Opinion in Electrochemistry

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Enhanced electrochemical determination of quercetin in a choline chloride-based ionic liquid

Abstract: Au nanoparticles and graphene were used as modified electrodes. A DES was used as an enhancer for quercetin detection. Strong H-bond interactions were formed between the DES and quercetin. Determination in Huang-Qi-Jing oral liquid was achieved.

Cited by 7 publications

References 52 publications

Hybrids of Sterically Hindered Phenols and Diaryl Ureas: Synthesis, Switch from Antioxidant Activity to ROS Generation and Induction of Apoptosis

Hybrids of Sterically Hindered Phenols and Diaryl Ureas: Synthesis, Switch from Antioxidant Activity to ROS Generation and Induction of Apoptosis

Structure-dependent detection of polyphenols using crown ether-immobilized gold nanoparticles

Perspectives for the use of deep eutectic solvents in the preparation of electrochemical sensors and biosensors

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