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

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cris.lastimport.scopus2024-02-12T20:55:46Z
dc.abstract.plsoflavonoids 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 ransform 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%).
dc.affiliationUniwersytet Warszawski
dc.contributor.authorStolarczyk, Elżbieta U.
dc.contributor.authorStrzempek, Weronika
dc.contributor.authorŁaszcz, Marta
dc.contributor.authorLEŚ, ANDRZEJ
dc.contributor.authorMenaszek, Elżbieta
dc.contributor.authorStolarczyk, Krzysztof
dc.date.accessioned2024-01-26T10:51:59Z
dc.date.available2024-01-26T10:51:59Z
dc.date.copyright2022-07-15
dc.date.issued2022
dc.description.accesstimeAT_PUBLICATION
dc.description.financePublikacja bezkosztowa
dc.description.number14
dc.description.versionFINAL_PUBLISHED
dc.description.volume23
dc.identifier.doi10.3390/IJMS23147816
dc.identifier.issn1422-0067
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/123339
dc.identifier.weblinkhttps://www.mdpi.com/1422-0067/23/14/7816/pdf
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofInternational Journal of Molecular Sciences
dc.relation.pages7816
dc.rightsCC-BY
dc.sciencecloudnosend
dc.subject.enantioxidant
dc.subject.enantitumor
dc.subject.enbiologically active compounds
dc.subject.enelectrochemistry
dc.subject.enelectrospray ion- ization
dc.subject.enstructure elucidation
dc.subject.enidentification
dc.subject.enmolecular modeling
dc.subject.enoxidation mechanisms
dc.subject.enspectroscopic data
dc.titleThiogenistein—Antioxidant Chemistry, Antitumor Activity, and Structure Elucidation of New Oxidation Products
dc.typeJournalArticle
dspace.entity.typePublication