A study on redox reactions of the azo dye Sudan I and its hydroxylated metabolites on pyrolytic graphite and boron doped diamond electrodes to support electrochemical studies of metabolic transformations

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F68081707%3A_____%2F23%3A00577354" target="_blank" >RIV/68081707:_____/23:00577354 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/00216208:11310/23:10472921 RIV/00216224:14310/23:00133089

Výsledek na webu

<a href="https://www.sciencedirect.com/science/article/pii/S0013468623013348?via%3Dihub" target="_blank" >https://www.sciencedirect.com/science/article/pii/S0013468623013348?via%3Dihub</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.electacta.2023.143162" target="_blank" >10.1016/j.electacta.2023.143162</a>

Jazyk výsledku

angličtina

Název v původním jazyce

A study on redox reactions of the azo dye Sudan I and its hydroxylated metabolites on pyrolytic graphite and boron doped diamond electrodes to support electrochemical studies of metabolic transformations

Popis výsledku v původním jazyce

Sudan I (1-(Phenyldiazenyl)naphthalen-2-ol) is an orange industrial azo dye. It is utilized as a marker substrate in studies of metabolic transformation of xenobiotics through processes involving cytochrome P450 hydroxylase. In this complex study, redox and subsequent chemical/electrochemical reactions of Sudan I and its three major metabolites (4 '-hydroxy, 6-hydroxy, and 4 ',6-dihydroxy derivatives of Sudan I) were investigated using boron doped diamond and basal plane pyrolytic graphite electrodes. Cyclic voltammetry (CV) in Britton Robinson buffer pH 7 showed distinct differences in the number and potential of signals, depending on the number and positions of the hydroxy groups. While in CV scans initiated in anodic direction, primary oxidations of paired or unpaired hydroxy groups are dominating, cathodic scans lead primarily to reduction of the azo group and to cleavage of the parent compounds and formation of 1-aminonaphthalen-2-ol and aniline or their corresponding hydroxylated derivatives. These are oxidizable in reverse anodic scans. Combinations of CV scans can be used to distinguish among all tested compounds. Basal plane pyrolytic graphite electrode provides better sensitivity than boron doped diamond electrode due to enhanced adsorption of the aromatic analytes/intermediates. The possibility of detecting Sudan I and its metabolites in the presence of excess amounts of NADPH as an essential component of enzymatic hydroxylation systems, was tested. Although the oxidation signal of NADPH partially interferes with signals of primary oxidation of hydroxy groups (particularly for Sudan I), our results suggest that electrochemical assays could be applicable in monitoring transformation of Sudan I in biochemical studies.

Název v anglickém jazyce

A study on redox reactions of the azo dye Sudan I and its hydroxylated metabolites on pyrolytic graphite and boron doped diamond electrodes to support electrochemical studies of metabolic transformations

Popis výsledku anglicky

Sudan I (1-(Phenyldiazenyl)naphthalen-2-ol) is an orange industrial azo dye. It is utilized as a marker substrate in studies of metabolic transformation of xenobiotics through processes involving cytochrome P450 hydroxylase. In this complex study, redox and subsequent chemical/electrochemical reactions of Sudan I and its three major metabolites (4 '-hydroxy, 6-hydroxy, and 4 ',6-dihydroxy derivatives of Sudan I) were investigated using boron doped diamond and basal plane pyrolytic graphite electrodes. Cyclic voltammetry (CV) in Britton Robinson buffer pH 7 showed distinct differences in the number and potential of signals, depending on the number and positions of the hydroxy groups. While in CV scans initiated in anodic direction, primary oxidations of paired or unpaired hydroxy groups are dominating, cathodic scans lead primarily to reduction of the azo group and to cleavage of the parent compounds and formation of 1-aminonaphthalen-2-ol and aniline or their corresponding hydroxylated derivatives. These are oxidizable in reverse anodic scans. Combinations of CV scans can be used to distinguish among all tested compounds. Basal plane pyrolytic graphite electrode provides better sensitivity than boron doped diamond electrode due to enhanced adsorption of the aromatic analytes/intermediates. The possibility of detecting Sudan I and its metabolites in the presence of excess amounts of NADPH as an essential component of enzymatic hydroxylation systems, was tested. Although the oxidation signal of NADPH partially interferes with signals of primary oxidation of hydroxy groups (particularly for Sudan I), our results suggest that electrochemical assays could be applicable in monitoring transformation of Sudan I in biochemical studies.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10405 - Electrochemistry (dry cells, batteries, fuel cells, corrosion metals, electrolysis)

Projekt

<a href="/cs/project/GA20-03187S" target="_blank" >GA20-03187S: Studium elektrochemických a adsorpčních dějů na nanostrukturovaných sp2 a sp3 uhlíkových površích ve vztahu k jejich fyzikálně chemickým vlastnostem</a><br>

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2023

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

468

Číslo periodika v rámci svazku

NOV 10 2023

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

14

Strana od-do

143162

Kód UT WoS článku

001082382500001

EID výsledku v databázi Scopus

2-s2.0-85171433226