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Parabanic acid is the singlet oxygen specific oxidation product of uric acid

Uric acid quenches singlet oxygen physically or reacts with it, but the oxidation product has not been previously characterized. The present study determined that the product is parabanic acid, which was confirmed by LC/TOFMS analysis. Parabanic acid was stable at acidic pH (<5.0), but hydrolyzed...

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Autores principales: Iida, Sayaka, Ohkubo, Yuki, Yamamoto, Yorihiro, Fujisawa, Akio
Formato: Online Artículo Texto
Lenguaje:English
Publicado: the Society for Free Radical Research Japan 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5703782/
https://www.ncbi.nlm.nih.gov/pubmed/29203957
http://dx.doi.org/10.3164/jcbn.17-24
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author Iida, Sayaka
Ohkubo, Yuki
Yamamoto, Yorihiro
Fujisawa, Akio
author_facet Iida, Sayaka
Ohkubo, Yuki
Yamamoto, Yorihiro
Fujisawa, Akio
author_sort Iida, Sayaka
collection PubMed
description Uric acid quenches singlet oxygen physically or reacts with it, but the oxidation product has not been previously characterized. The present study determined that the product is parabanic acid, which was confirmed by LC/TOFMS analysis. Parabanic acid was stable at acidic pH (<5.0), but hydrolyzed to oxaluric acid at neutral or alkaline pH. The total yields of parabanic acid and oxaluric acid based on consumed uric acid were ~100% in clean singlet oxygen production systems such as UVA irradiation of Rose Bengal and thermal decomposition of 3-(1,4-dihydro-1,4-epidioxy-4-methyl-1-naphthyl)propionic acid. However, the ratio of the amount of uric acid consumed to the total amount of singlet oxygen generated was less than 1/180, indicating that most of the singlet oxygen was physically quenched. The total yields of parabanic acid and oxaluric acid were high in the uric acid oxidation systems with hydrogen peroxide plus hypochlorite or peroxynitrite. They became less than a few percent in peroxyl radical-, hypochlorite- or peroxynitrite-induced oxidation of uric acid. These results suggest that parabanic acid could be an in vivo probe of singlet oxygen formation because of the wide distribution of uric acid in human tissues and extracellular spaces. In fact, sunlight exposure significantly increased human skin levels of parabanic acid.
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spelling pubmed-57037822017-12-04 Parabanic acid is the singlet oxygen specific oxidation product of uric acid Iida, Sayaka Ohkubo, Yuki Yamamoto, Yorihiro Fujisawa, Akio J Clin Biochem Nutr Original Article Uric acid quenches singlet oxygen physically or reacts with it, but the oxidation product has not been previously characterized. The present study determined that the product is parabanic acid, which was confirmed by LC/TOFMS analysis. Parabanic acid was stable at acidic pH (<5.0), but hydrolyzed to oxaluric acid at neutral or alkaline pH. The total yields of parabanic acid and oxaluric acid based on consumed uric acid were ~100% in clean singlet oxygen production systems such as UVA irradiation of Rose Bengal and thermal decomposition of 3-(1,4-dihydro-1,4-epidioxy-4-methyl-1-naphthyl)propionic acid. However, the ratio of the amount of uric acid consumed to the total amount of singlet oxygen generated was less than 1/180, indicating that most of the singlet oxygen was physically quenched. The total yields of parabanic acid and oxaluric acid were high in the uric acid oxidation systems with hydrogen peroxide plus hypochlorite or peroxynitrite. They became less than a few percent in peroxyl radical-, hypochlorite- or peroxynitrite-induced oxidation of uric acid. These results suggest that parabanic acid could be an in vivo probe of singlet oxygen formation because of the wide distribution of uric acid in human tissues and extracellular spaces. In fact, sunlight exposure significantly increased human skin levels of parabanic acid. the Society for Free Radical Research Japan 2017-11 2017-09-05 /pmc/articles/PMC5703782/ /pubmed/29203957 http://dx.doi.org/10.3164/jcbn.17-24 Text en Copyright © 2017 JCBN http://creativecommons.org/licenses/by/3.0/ This is an open access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Original Article
Iida, Sayaka
Ohkubo, Yuki
Yamamoto, Yorihiro
Fujisawa, Akio
Parabanic acid is the singlet oxygen specific oxidation product of uric acid
title Parabanic acid is the singlet oxygen specific oxidation product of uric acid
title_full Parabanic acid is the singlet oxygen specific oxidation product of uric acid
title_fullStr Parabanic acid is the singlet oxygen specific oxidation product of uric acid
title_full_unstemmed Parabanic acid is the singlet oxygen specific oxidation product of uric acid
title_short Parabanic acid is the singlet oxygen specific oxidation product of uric acid
title_sort parabanic acid is the singlet oxygen specific oxidation product of uric acid
topic Original Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5703782/
https://www.ncbi.nlm.nih.gov/pubmed/29203957
http://dx.doi.org/10.3164/jcbn.17-24
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