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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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Formato: | Online Artículo Texto |
Lenguaje: | English |
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the Society for Free Radical Research Japan
2017
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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. |
format | Online Article Text |
id | pubmed-5703782 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | the Society for Free Radical Research Japan |
record_format | MEDLINE/PubMed |
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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