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Anti-cancer and electrochemical properties of thiogenistein : new biologically active compound

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cris.lastimport.scopus2024-02-12T19:47:32Z
dc.abstract.enPharmacological and nutraceutical effects of isoflavones, which include genistein (GE), are attributed to their antioxidant activity protecting cells against carcinogenesis. The knowledge of the oxidation mechanisms of an active substance is crucial to determine its pharmacological properties. The aim of the present work was to explain complex oxidation processes that have been simulated during voltammetric experiments for our new thiolated genistein analog (TGE) that formed the self-assembled monolayer (SAM) on the gold electrode. The thiol linker assured a strong interaction of sulfur nucleophiles with the gold surface. The research comprised of the study of TGE oxidative properties, IR-ATR, and MALDI-TOF measurements of SAM before and after electrochemical oxidation. TGE has been shown to be electrochemically active. It undergoes one irreversible oxidation reaction and one quasi-reversible oxidation reaction in PBS buffer at pH 7.4. The oxidation of TGE results in electroactive products composed likely from TGE conjugates (e.g., trimers) as part of polymer. The electroactive centers of TGE and its oxidation mechanism were discussed using IR supported by quantum chemical and molecular mechanics calculations. Preliminary in-vitro studies indicate that TGE exhibits higher cytotoxic activity towards DU145 human prostate cancer cells and is safer for normal prostate epithelial cells (PNT2) than genistein itself.
dc.affiliationUniwersytet Warszawski
dc.contributor.authorStolarczyk, Elżbieta
dc.contributor.authorLEŚ, ANDRZEJ
dc.contributor.authorStolarczyk, Krzysztof
dc.contributor.authorSidoryk, Katarzyna
dc.contributor.authorŁaszcz, Marta
dc.contributor.authorMenaszek, Elżbieta
dc.contributor.authorStrzempek, Weronika
dc.date.accessioned2024-01-24T16:40:14Z
dc.date.available2024-01-24T16:40:14Z
dc.date.copyright2021-09-30
dc.date.issued2021
dc.description.accesstimeAT_PUBLICATION
dc.description.financePublikacja bezkosztowa
dc.description.number16
dc.description.versionFINAL_PUBLISHED
dc.description.volume22
dc.identifier.doi10.3390/IJMS22168783
dc.identifier.issn1422-0067
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/100779
dc.identifier.weblinkhttps://www.mdpi.com/1422-0067/22/16/8783/htm
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofInternational Journal of Molecular Sciences
dc.rightsCC-BY
dc.sciencecloudnosend
dc.subject.enanticancer drugs
dc.subject.ennanoparticles
dc.subject.enmolecular modeling
dc.subject.enoxidation mechanisms
dc.subject.enelectrochemistry
dc.subject.enMALDI
dc.subject.enspectroscopic data
dc.subject.encytotoxic study
dc.subject.enself-assembled monolayer
dc.subject.engold electrode
dc.titleAnti-cancer and electrochemical properties of thiogenistein : new biologically active compound
dc.typeJournalArticle
dspace.entity.typePublication