The Interplay of Ascorbic Acid with Quinones-Chelators-Influence on Lipid Peroxidation: Insight into Anticancer Activity.

Olga Yu Selyutina,Lidiya G Fedenok,Polina A Kononova,Nikolay E Polyakov,Vladimir E Koshman

doi:10.3390/antiox11020376

Olga Yu Selyutina, Lidiya G Fedenok + Show 3 more

Open Access

https://doi.org/10.3390/antiox11020376

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Abstract

Ascorbic acid is a multifaceted compound that can perform both antioxidant and pro-oxidant activities in the redox reactions induced by transition metal ions, so its role in nature and especially in the human body is still the subject of debate. In the present study, we have examined the influence of ascorbic acid on lipid peroxidation in a model system that mimics the cell membrane, namely micelles of linoleic acid (LA), induced by chelate complexes of iron and copper ions with quinone-chelator 2-phenyl-4-(butylamino)-naphtholquinoline-7,12-dione (Q1). This quinone effectively generates reactive oxygen species and semiquinone radicals inside cancer cells via a cycling redox reaction. Here it was demonstrated that in the absence of quinone-chelator ascorbic acid significantly accelerates the lipid peroxidation induced by both Fe(II) and Cu(II) ions. It has been shown also that Q1 chelate complexes with Fe(II) and Cu(II) ions are redox active in the LA micelles oxidation. No effect of ascorbate was detected on the reactivity of chelate complex with Fe(II) ions. On the other hand, ascorbate performs pro-oxidant activity in Q1-Cu(II) complex induced reaction. We can conclude that ascorbate-driven redox cycling of Q1 may promote its anti-tumor activity.

Highlights

Vitamin C or ascorbic acid (AA) is the most common vitamin, which is widely used as a nutraceutical supplement throughout the world [1,2]
Is a hydrophilic compound and slowly penetrates through the cell membrane via passive transport, and the main pathway of AA penetration into the cell is regulated by sodiumdependent vitamin C transporter 1 and 2 (SVCT1 and SVCT2) [3,4]
Study, we we have have examined examined the the influence influence of of ascorbic ascorbic acid acid on on lipid lipid peroxperoxiIn dation in model system system that that mimics mimics the the cell cellmembrane, membrane,namely namelymicelles micellesof oflinoleic linoleicacid, acid, idation in aa model induced by chelate complexes of iron and copper ions in the presence of hydrogen peroxide

Summary

Introduction

Vitamin C or ascorbic acid (AA) is the most common vitamin, which is widely used as a nutraceutical supplement throughout the world [1,2]. The bioavailability of ascorbic acid is dose-dependent (higher absorption is observed at a lower dose) and is actively transported through cell membranes [5]. The concentration of vitamin C in plasma varies in the range ~50–150 μM. Intracellular vitamin C levels can reach significantly higher concentrations, up to 4 mM in lymphocytes or 10 mM in neurons [5]. Studies on different cell cultures revealed a high level of AA in mitochondria isolated from various animal tissues [3,6]. It is interesting from the point of antioxidant/pro-oxidant activity of AA due to the intensive production of reactive oxygen species in mitochondria [3,6]

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