Electrochemical oxidation of non-aromatic sterols possessing double bond (s) in the steroid core on carbon-based electrodes

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F25%3A10504905" target="_blank" >RIV/00216208:11310/25:10504905 - isvavai.cz</a>

Výsledek na webu

<a href="https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=JH9xM0bAIZ" target="_blank" >https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=JH9xM0bAIZ</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.electacta.2025.146666" target="_blank" >10.1016/j.electacta.2025.146666</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Electrochemical oxidation of non-aromatic sterols possessing double bond (s) in the steroid core on carbon-based electrodes

Popis výsledku v původním jazyce

Sterols are essential components of eukaryotic cell membranes. They possess a hydroxyl group at C(3) and an unsaturated steroid skeleton. Their detection in biological and physiological matrices is rather challenging, relying on MS techniques or enzymatic assays. This study focused on exploring the electrochemical behavior of sterols in dependence on positioning and number of double bonds within the steroid core using cyclic voltammetry. The experiments were performed in the media of perchlorate salt or perchloric acid in acetonitrile using glassy carbon and boron doped diamond electrode. Sterols featuring Δ(5) double bond (cholesterol, stigmasterol, β-sitosterol) and Δ(7) lathosterol provide primary oxidation signals around +1.5 V to +1.7 V (vs. Ag/AgNO3 in acetonitrile). The oxidation potential of Δ(8) lanosterol (ca +1.1 V) and Δ(5,7) sterols (ergosterol, 7-dehydrocholesterol, around +0.8 V to +1.0 V) is shifted to less positive potential values. Notably, in the presence of perchloric acid, the oxidation signals of Δ(5,7) sterols exhibit time instability. It can be attributed to structural changes induced by dehydration, similar to cholesterol dehydration in the Liebermann-Burchard reaction. The lowest detection limits were obtained by differential pulse voltammetry in 0.1 mol L(-1) HClO4 in acetonitrile and are in the range from 0.4 to 0.6 µmol L(-1) for Δ(5,7) and Δ(8) sterols on BDD electrode and from 1.1 to 6.1 µmol L(-1) for Δ(5) and Δ(7) sterols on GC electrode. This electrode has limited use for the detection of Δ(5) sterols with a highly positive oxidation potential, in the 0.1 mol L(-1) NaClO4 in acetonitrile media. This study extends the knowledge on sterol redox processes and shows the potential of simple electrochemical methods for sterol detection using unmodified electrode materials.

Název v anglickém jazyce

Electrochemical oxidation of non-aromatic sterols possessing double bond (s) in the steroid core on carbon-based electrodes

Popis výsledku anglicky

Sterols are essential components of eukaryotic cell membranes. They possess a hydroxyl group at C(3) and an unsaturated steroid skeleton. Their detection in biological and physiological matrices is rather challenging, relying on MS techniques or enzymatic assays. This study focused on exploring the electrochemical behavior of sterols in dependence on positioning and number of double bonds within the steroid core using cyclic voltammetry. The experiments were performed in the media of perchlorate salt or perchloric acid in acetonitrile using glassy carbon and boron doped diamond electrode. Sterols featuring Δ(5) double bond (cholesterol, stigmasterol, β-sitosterol) and Δ(7) lathosterol provide primary oxidation signals around +1.5 V to +1.7 V (vs. Ag/AgNO3 in acetonitrile). The oxidation potential of Δ(8) lanosterol (ca +1.1 V) and Δ(5,7) sterols (ergosterol, 7-dehydrocholesterol, around +0.8 V to +1.0 V) is shifted to less positive potential values. Notably, in the presence of perchloric acid, the oxidation signals of Δ(5,7) sterols exhibit time instability. It can be attributed to structural changes induced by dehydration, similar to cholesterol dehydration in the Liebermann-Burchard reaction. The lowest detection limits were obtained by differential pulse voltammetry in 0.1 mol L(-1) HClO4 in acetonitrile and are in the range from 0.4 to 0.6 µmol L(-1) for Δ(5,7) and Δ(8) sterols on BDD electrode and from 1.1 to 6.1 µmol L(-1) for Δ(5) and Δ(7) sterols on GC electrode. This electrode has limited use for the detection of Δ(5) sterols with a highly positive oxidation potential, in the 0.1 mol L(-1) NaClO4 in acetonitrile media. This study extends the knowledge on sterol redox processes and shows the potential of simple electrochemical methods for sterol detection using unmodified electrode materials.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10406 - Analytical chemistry

Projekt

<a href="/cs/project/GA19-11268S" target="_blank" >GA19-11268S: Elektrochemické metody: Nové přístupy pro charakterizaci a analýzu steroidů</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2025

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Electrochimica Acta

ISSN

0013-4686

e-ISSN

1873-3859

Svazek periodika

536

Číslo periodika v rámci svazku

October

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

8

Strana od-do

146666

Kód UT WoS článku

001516777000001

EID výsledku v databázi Scopus

2-s2.0-105008335033