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Oxidation of Hydroxy- and Dihydroxybenzoic Acids Under the Udenfriend's Conditions. An HPLC Study

BACKGROUND: Non-enzymatic hydroxylation of aromatic compounds to the respective phenolic derivatives is a possible metabolic pathway of xenobiotics. The formed metabolites can undergo consecutive oxidative reactions with free radicals to form potential toxic molecules. OBJECTIVE: Development of HPLC...

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Autores principales: Kuzma, Mónika, Kovács, Nikoletta, Sziva, Lilla, Maász, Gábor, Avar, Péter, Perjési, Pál
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Bentham Open 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5815051/
https://www.ncbi.nlm.nih.gov/pubmed/29492167
http://dx.doi.org/10.2174/1874104501812010013
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author Kuzma, Mónika
Kovács, Nikoletta
Sziva, Lilla
Maász, Gábor
Avar, Péter
Perjési, Pál
author_facet Kuzma, Mónika
Kovács, Nikoletta
Sziva, Lilla
Maász, Gábor
Avar, Péter
Perjési, Pál
author_sort Kuzma, Mónika
collection PubMed
description BACKGROUND: Non-enzymatic hydroxylation of aromatic compounds to the respective phenolic derivatives is a possible metabolic pathway of xenobiotics. The formed metabolites can undergo consecutive oxidative reactions with free radicals to form potential toxic molecules. OBJECTIVE: Development of HPLC methods to separate, identify and quantitate the main products formed from salicylic acid, 2,3-dihydroxybenzoic acid and 2,5-dihydroxybenzoic acid under in vitro hydroxylation conditions (Udenfriend's system). METHOD: An RP-HPLC-UV-Vis method was developed to separate salicylic acid and isomeric dihydroxybenzoic acids formed in the Udenfriend's system. Confirmation of structures of the oxidized products of salicylic acid, 2,3-dihydroxybenzoic acid and 2,5-dihydroxybenzoic acid was performed by HPLC-ESI-MS/MS method. RESULTS: The HPLC-UV-Vis method was evaluated for a number of validation characteristics (selectivity, repeatability and intermediate precision, LOD, LOQ and calibration range). It was found that oxidation of salicylic acid resulted in the formation of 2,3- and 2,5-dihydroxybenzoic acids. Furthermore, the hydroxylated metabolites can be further metabolized under the Udenfriend’s conditions. CONCLUSION: The results give evidence for possible involvement of the oxidized metabolites of salicylic acid in the development of biological action of salicylates at the site of inflammation, where high hydroxyl radical level can be detected.
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spelling pubmed-58150512018-02-28 Oxidation of Hydroxy- and Dihydroxybenzoic Acids Under the Udenfriend's Conditions. An HPLC Study Kuzma, Mónika Kovács, Nikoletta Sziva, Lilla Maász, Gábor Avar, Péter Perjési, Pál Open Med Chem J Medicinal Chemistry BACKGROUND: Non-enzymatic hydroxylation of aromatic compounds to the respective phenolic derivatives is a possible metabolic pathway of xenobiotics. The formed metabolites can undergo consecutive oxidative reactions with free radicals to form potential toxic molecules. OBJECTIVE: Development of HPLC methods to separate, identify and quantitate the main products formed from salicylic acid, 2,3-dihydroxybenzoic acid and 2,5-dihydroxybenzoic acid under in vitro hydroxylation conditions (Udenfriend's system). METHOD: An RP-HPLC-UV-Vis method was developed to separate salicylic acid and isomeric dihydroxybenzoic acids formed in the Udenfriend's system. Confirmation of structures of the oxidized products of salicylic acid, 2,3-dihydroxybenzoic acid and 2,5-dihydroxybenzoic acid was performed by HPLC-ESI-MS/MS method. RESULTS: The HPLC-UV-Vis method was evaluated for a number of validation characteristics (selectivity, repeatability and intermediate precision, LOD, LOQ and calibration range). It was found that oxidation of salicylic acid resulted in the formation of 2,3- and 2,5-dihydroxybenzoic acids. Furthermore, the hydroxylated metabolites can be further metabolized under the Udenfriend’s conditions. CONCLUSION: The results give evidence for possible involvement of the oxidized metabolites of salicylic acid in the development of biological action of salicylates at the site of inflammation, where high hydroxyl radical level can be detected. Bentham Open 2018-01-31 /pmc/articles/PMC5815051/ /pubmed/29492167 http://dx.doi.org/10.2174/1874104501812010013 Text en © 2018 Kuzma et al. https://creativecommons.org/licenses/by/4.0/legalcode This is an open access article distributed under the terms of the Creative Commons Attribution 4. 0 International Public License (CC-BY 4. 0), a copy of which is available at: https://creativecommons. org/licenses/by/4. 0/legalcode. This license permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.
spellingShingle Medicinal Chemistry
Kuzma, Mónika
Kovács, Nikoletta
Sziva, Lilla
Maász, Gábor
Avar, Péter
Perjési, Pál
Oxidation of Hydroxy- and Dihydroxybenzoic Acids Under the Udenfriend's Conditions. An HPLC Study
title Oxidation of Hydroxy- and Dihydroxybenzoic Acids Under the Udenfriend's Conditions. An HPLC Study
title_full Oxidation of Hydroxy- and Dihydroxybenzoic Acids Under the Udenfriend's Conditions. An HPLC Study
title_fullStr Oxidation of Hydroxy- and Dihydroxybenzoic Acids Under the Udenfriend's Conditions. An HPLC Study
title_full_unstemmed Oxidation of Hydroxy- and Dihydroxybenzoic Acids Under the Udenfriend's Conditions. An HPLC Study
title_short Oxidation of Hydroxy- and Dihydroxybenzoic Acids Under the Udenfriend's Conditions. An HPLC Study
title_sort oxidation of hydroxy- and dihydroxybenzoic acids under the udenfriend's conditions. an hplc study
topic Medicinal Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5815051/
https://www.ncbi.nlm.nih.gov/pubmed/29492167
http://dx.doi.org/10.2174/1874104501812010013
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