Analysis of Protein-Phenolic Compound Modifications Using Electrochemistry Coupled to Mass Spectrometry

Kallinich, Constanze; Schefer, Simone; Rohn, Sascha

doi:10.3390/molecules23020264

Cited by 9 publications

(1 citation statement)

References 31 publications

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“…The ROXY™ electrochemical system is a technique that can be applied for mimicking drug metabolism [ 30 , 31 ] or for interaction studies [ 32 ] as well as other electrochemical cells coupled on-line to the electrospray ionisation (ESI)-MS for study of biological redox reactions [ 33 ]. In the work of Sagandykova and co-workers [ 34 ], the electrochemical unit coupled to ESI-MS was used for fragmentation activity relationships of selected flavonoids.…”

Section: Resultsmentioning

confidence: 99%

Thiogenistein—Antioxidant Chemistry, Antitumor Activity, and Structure Elucidation of New Oxidation Products

Stolarczyk

Strzempek

Łaszcz

et al. 2022

IJMS

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Isoflavonoids such as genistein (GE) are well known antioxidants. The predictive biological activity of structurally new compounds such as thiogenistein (TGE)—a new analogue of GE—becomes an interesting way to design new drug candidates with promising properties. Two oxidation strategies were used to characterize TGE oxidation products: the first in solution and the second on the 2D surface of the Au electrode as a self-assembling TGE monolayer. The structure elucidation of products generated by different oxidation strategies was performed. The electrospray ionization mass spectrometry (ESI-MS) was used for identifying the product of electrochemical and hydrogen peroxide oxidation in the solution. Fourier transform infrared spectroscopy (FT-IR) with the ATR mode was used to identify a product after hydrogen peroxide treatment of TGE on the 2D surface. The density functional theory was used to support the experimental results for the estimation of antioxidant activity of TGE as well as for the molecular modeling of oxidation products. The biological studies were performed simultaneously to assess the suitability of TGE for antioxidant and antitumor properties. It was found that TGE was characterized by a high cytotoxic activity toward human breast cancer cells. The research was also carried out on mice macrophages, disclosing that TGE neutralized the production of the LPS-induced reactive oxygen species (ROS) and exhibits ABTS(2,2′-azino-bis-3-(ethylbenzothiazoline-6-sulphonic acid) radical scavenging ability. In the presented study, we identified the main oxidation products of TGE generated under different environmental conditions. The electroactive centers of TGE were identified and its oxidation mechanisms were proposed. TGE redox properties can be related to its various pharmacological activities. Our new thiolated analogue of genistein neutralizes the LPS-induced ROS production better than GE. Additionally, TGE shows a high cytotoxic activity against human breast cancer cells. The viability of MCF-7 (estrogen-positive cells) drops two times after a 72-h incubation with 12.5 μM TGE (viability 53.86%) compared to genistein (viability 94.46%).

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Section: Resultsmentioning

confidence: 99%

Thiogenistein—Antioxidant Chemistry, Antitumor Activity, and Structure Elucidation of New Oxidation Products

Stolarczyk

Strzempek

Łaszcz

et al. 2022

IJMS

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Recent Developments in Electrochemistry–Mass Spectrometry

Herl

Matysik

2020

ChemElectroChem

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Hyphenation of electrochemistry and mass spectrometry is an attractive method to investigate oxidation and reduction processes. By using mass spectrometry, electrochemically generated products can be identified. In this Review, different approaches to electrochemistry–mass spectrometry will be summarized, including hyphenation of electrochemical flow cells to mass spectrometry as well as integration of separation steps between electrochemical reactions and detection of products. Fields of application range from bioanalytical studies to studies regarding corrosion, electrosynthesis and energy carriers. Important historical developments will be highlighted, followed by an overview of terminology and instrumental setups and discussion of developments within recent years (2017–2020).

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Combination of electrochemical unit and ESI‐MS in fragmentation of flavonoids

Sagandykova

Szultka‐Młyńska

Walczak-Skierska

et al. 2020

Phytochemical Analysis

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Introduction: Predictive approaches on the activity of natural compounds based on the fragmentation by instrumental techniques are important for consideration of such molecules as drug candidates and defining new structures with promising properties. Since flavonoids are well-known antioxidants, their redox properties can be related to their pharmacological activity. Objectives: In this work, the potential of electrochemical unit coupled to electrospray ionisation mass spectrometry (ESI-MS) was assessed for fragmentation activity relationships studies of selected flavonoids. Methodology: Methodology of this research included electrochemical conversion of standards of flavonoids at different pH values and their further analysis with the use of ESI-MS. In addition, signals obtained from the blank samples were also identified and used for interpretation due to electrochemical nature of the ESI source. Half maximal inhibitory concentration (IC 50 ) values of flavonoids for 2,2 0 -azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) and 2,2-diphenyl-1-picrylhydrazyl (DPPH) antioxidant activity assays were analysed for possible correlation with the structures of flavonoids and products of electrochemical conversion.Results: Fragmentation activity relationships were suggested using the proposed approach and for some of the flavonoids it was not specific enough to determine the input of a particular structural feature to the activity, but for others they were in agreement with those found in the literature. Obtained results showed potential of the proposed approach for application in plant sciences as a fast pre-screening tool for newly isolated bioactive compounds.

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Analysis of Protein-Phenolic Compound Modifications Using Electrochemistry Coupled to Mass Spectrometry

Cited by 9 publications

References 31 publications

Thiogenistein—Antioxidant Chemistry, Antitumor Activity, and Structure Elucidation of New Oxidation Products

Thiogenistein—Antioxidant Chemistry, Antitumor Activity, and Structure Elucidation of New Oxidation Products

Recent Developments in Electrochemistry–Mass Spectrometry

Combination of electrochemical unit and ESI‐MS in fragmentation of flavonoids

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