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

J 2023

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

ONDRÁČKOVÁ, Anna, Marie STIBOROVÁ, Helena DRAČÍNSKÁ, Ludek HAVRAN, Karolina SCHWARZOVÁ-PECKOVÁ et. al.

Basic information

Original 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

Authors

ONDRÁČKOVÁ, Anna (203 Czech Republic, belonging to the institution), Marie STIBOROVÁ, Helena DRAČÍNSKÁ, Ludek HAVRAN, Karolina SCHWARZOVÁ-PECKOVÁ and Miroslav FOJTA

Edition

Electrochimica Acta, Elsevier, 2023, 0013-4686

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10403 Physical chemistry

Country of publisher

United Kingdom of Great Britain and Northern Ireland

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 6.600 in 2022

RIV identification code

RIV/00216224:14310/23:00133089

Organization unit

Faculty of Science

DOI

http://dx.doi.org/10.1016/j.electacta.2023.143162

UT WoS

001082382500001

Keywords in English

Adsorption; Boron -doped diamond; Pyrolytic graphite; Voltammetry; Sudan I; Reduction; Oxidation; Hydroxylation; Metabolites

Abstract

V originále

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.

Citovat

ONDRÁČKOVÁ, Anna, Marie STIBOROVÁ, Helena DRAČÍNSKÁ, Ludek HAVRAN, Karolina SCHWARZOVÁ-PECKOVÁ and Miroslav FOJTA. 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. Electrochimica Acta. Elsevier, 2023, vol. 468, November, p. 1-14. ISSN 0013-4686. Available from: https://dx.doi.org/10.1016/j.electacta.2023.143162.

@article{2362580,
   author = {Ondráčková, Anna and Stiborová, Marie and Dračínská, Helena and Havran, Ludek and SchwarzováandPecková, Karolina and Fojta, Miroslav},
   article_number = {November},
   doi = {http://dx.doi.org/10.1016/j.electacta.2023.143162},
   keywords = {Adsorption; Boron -doped diamond; Pyrolytic graphite; Voltammetry; Sudan I; Reduction; Oxidation; Hydroxylation; Metabolites},
   language = {eng},
   issn = {0013-4686},
   journal = {Electrochimica Acta},
   title = {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},
   url = {https://doi.org/10.1016/j.electacta.2023.143162},
   volume = {468},
   year = {2023}
}

TY  - JOUR
ID  - 2362580
AU  - Ondráčková, Anna - Stiborová, Marie - Dračínská, Helena - Havran, Ludek - Schwarzová-Pecková, Karolina - Fojta, Miroslav
PY  - 2023
TI  - 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
JF  - Electrochimica Acta
VL  - 468
IS  - November
SP  - 1-14
EP  - 1-14
PB  - Elsevier
SN  - 00134686
KW  - Adsorption
KW  - Boron -doped diamond
KW  - Pyrolytic graphite
KW  - Voltammetry
KW  - Sudan I
KW  - Reduction
KW  - Oxidation
KW  - Hydroxylation
KW  - Metabolites
UR  - https://doi.org/10.1016/j.electacta.2023.143162
N2  - 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.
ER  -

ONDRÁČKOVÁ, Anna, Marie STIBOROVÁ, Helena DRAČÍNSKÁ, Ludek HAVRAN, Karolina SCHWARZOVÁ-PECKOVÁ and Miroslav FOJTA. 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. \textit{Electrochimica Acta}. Elsevier, 2023, vol.~468, November, p.~1-14. ISSN~0013-4686. Available from: https://dx.doi.org/10.1016/j.electacta.2023.143162.

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