Abstract
Pharmacological 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.
Highlights
Genistein (GE) belongs to the group of isoflavones found mainly in soybeans [1,2].Some studies suggest that frequent consumption of soy-based products in Asian countries reduces the incidence of breast and prostate cancer compared to Western countries.Genistein has antioxidant, anti-inflammatory, antiangiogenic, pro-apoptotic, and antiproliferative properties, which gives it great potential for use in anti-cancer therapy
In our previous article [5], we described experiments performed by cyclic voltammetry with free genistein dissolved in PBS buffer pH 7.4 using a glassy carbon electrode (GCE)
In the first anode half-cycle, we observed the first peak at approx. 0.4 V which corresponded to the irreversible oxidation of the hydroxyl group on the C40 carbon ring of genistein, while a second peak at approx. 0.8 V corresponded to the oxidation of hydroxyl groups on the C5, C7 carbon ring of genistein
Summary
Genistein (GE) belongs to the group of isoflavones found mainly in soybeans [1,2].Some studies suggest that frequent consumption of soy-based products in Asian countries reduces the incidence of breast and prostate cancer compared to Western countries.Genistein has antioxidant, anti-inflammatory, antiangiogenic, pro-apoptotic, and antiproliferative properties, which gives it great potential for use in anti-cancer therapy. Genistein (GE) belongs to the group of isoflavones found mainly in soybeans [1,2]. Some studies suggest that frequent consumption of soy-based products in Asian countries reduces the incidence of breast and prostate cancer compared to Western countries. Anti-inflammatory, antiangiogenic, pro-apoptotic, and antiproliferative properties, which gives it great potential for use in anti-cancer therapy. It has been shown that genistein may influence the regulation of apoptosis, angiogenesis, metastasis, and various stages of the cell cycle. In addition to acting on transcription factors, genistein induces stress on the endoplasmic reticulum, which in turn leads to the apoptosis of neoplastic cells. It has been shown to induce apoptosis in cancer cells by targeting the PPAR (peroxisome proliferator-activated receptor) signaling cascade
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