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

0577354 - BFÚ 2024 RIV GB eng J - Článek v odborném periodiku
Ondráčková, Anna - Stiborová, M. - Dračínská, H. - Havran, Luděk - Schwarzová-Pecková, Karolina - Fojta, Miroslav
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. Roč. 468, NOV 10 2023 (2023), č. článku 143162. ISSN 0013-4686. E-ISSN 1873-3859
Grant CEP: GA ČR(CZ) GA20-03187S
Institucionální podpora: RVO:68081707
Klíčová slova: Adsorption * Borondoped diamond * Pyrolytic graphite * Voltammetry * Sudan I * Reduction * Oxidation * Hydroxylation * Metabolites
Obor OECD: Electrochemistry (dry cells, batteries, fuel cells, corrosion metals, electrolysis)
Impakt faktor: 6.6, rok: 2022
Způsob publikování: Omezený přístup
https://www.sciencedirect.com/science/article/pii/S0013468623013348?via%3Dihub

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.
Trvalý link: https://hdl.handle.net/11104/0349132