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

Result code in 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>

Alternative codes found

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

Result on the web

<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>

Result language

angličtina

Original language name

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

Original language description

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.

Czech name

—

Czech description

—

Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

—

OECD FORD branch

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

Project

<a href="/en/project/GA20-03187S" target="_blank" >GA20-03187S: Study of electrochemical and adsorption processes on nanostructured sp2 and sp3 carbon surfaces in relation to their physico-chemical characteristics</a><br>

Continuities

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2023

Confidentiality

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

Name of the periodical

Electrochimica acta

ISSN

0013-4686

e-ISSN

1873-3859

Volume of the periodical

468

Issue of the periodical within the volume

NOV 10 2023

Country of publishing house

GB - UNITED KINGDOM

Number of pages

14

Pages from-to

143162

UT code for WoS article

001082382500001

EID of the result in the Scopus database

2-s2.0-85171433226