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Methylated Phenylarsenical Metabolites Discovered in Chicken Liver
We report the discovery of three toxicologically relevant methylated phenylarsenical metabolites in the liver of chickens fed 3‐nitro‐4‐hydroxyphenylarsonic acid (ROX), a feed additive in poultry production that is still in use in several countries. Methyl‐3‐nitro‐4‐hydroxyphenylarsonic acid (methyl...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2017
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5573966/ https://www.ncbi.nlm.nih.gov/pubmed/28470989 http://dx.doi.org/10.1002/anie.201700736 |
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author | Peng, Hanyong Hu, Bin Liu, Qingqing Li, Jinhua Li, Xing‐Fang Zhang, Hongquan Le, X. Chris |
author_facet | Peng, Hanyong Hu, Bin Liu, Qingqing Li, Jinhua Li, Xing‐Fang Zhang, Hongquan Le, X. Chris |
author_sort | Peng, Hanyong |
collection | PubMed |
description | We report the discovery of three toxicologically relevant methylated phenylarsenical metabolites in the liver of chickens fed 3‐nitro‐4‐hydroxyphenylarsonic acid (ROX), a feed additive in poultry production that is still in use in several countries. Methyl‐3‐nitro‐4‐hydroxyphenylarsonic acid (methyl‐ROX), methyl‐3‐amino‐4‐hydroxyphenylarsonic acid (methyl‐3‐AHPAA), and methyl‐3‐acetamido‐4‐hydroxyphenylarsonic acid (or methyl‐N‐acetyl‐ROX, methyl‐N‐AHPAA) were identified in such chicken livers, and the concentration of methyl‐ROX was as high as 90 μg kg(−1), even after a five‐day clearance period. The formation of these newly discovered methylated metabolites from reactions involving trivalent phenylarsonous acid substrates, S‐adenosylmethionine, and the arsenic (+3 oxidation state) methyltransferase enzyme As3MT suggests that these compounds are formed by addition of a methyl group to a trivalent phenylarsenical substrate in an enzymatic process. The IC(50) values of the trivalent phenylarsenical compounds were 300–30 000 times lower than those of the pentavalent phenylarsenicals. |
format | Online Article Text |
id | pubmed-5573966 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-55739662017-09-15 Methylated Phenylarsenical Metabolites Discovered in Chicken Liver Peng, Hanyong Hu, Bin Liu, Qingqing Li, Jinhua Li, Xing‐Fang Zhang, Hongquan Le, X. Chris Angew Chem Int Ed Engl Communications We report the discovery of three toxicologically relevant methylated phenylarsenical metabolites in the liver of chickens fed 3‐nitro‐4‐hydroxyphenylarsonic acid (ROX), a feed additive in poultry production that is still in use in several countries. Methyl‐3‐nitro‐4‐hydroxyphenylarsonic acid (methyl‐ROX), methyl‐3‐amino‐4‐hydroxyphenylarsonic acid (methyl‐3‐AHPAA), and methyl‐3‐acetamido‐4‐hydroxyphenylarsonic acid (or methyl‐N‐acetyl‐ROX, methyl‐N‐AHPAA) were identified in such chicken livers, and the concentration of methyl‐ROX was as high as 90 μg kg(−1), even after a five‐day clearance period. The formation of these newly discovered methylated metabolites from reactions involving trivalent phenylarsonous acid substrates, S‐adenosylmethionine, and the arsenic (+3 oxidation state) methyltransferase enzyme As3MT suggests that these compounds are formed by addition of a methyl group to a trivalent phenylarsenical substrate in an enzymatic process. The IC(50) values of the trivalent phenylarsenical compounds were 300–30 000 times lower than those of the pentavalent phenylarsenicals. John Wiley and Sons Inc. 2017-05-04 2017-06-06 /pmc/articles/PMC5573966/ /pubmed/28470989 http://dx.doi.org/10.1002/anie.201700736 Text en © 2017 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution‐NonCommercial‐NoDerivs (http://creativecommons.org/licenses/by-nc-nd/4.0/) License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made. |
spellingShingle | Communications Peng, Hanyong Hu, Bin Liu, Qingqing Li, Jinhua Li, Xing‐Fang Zhang, Hongquan Le, X. Chris Methylated Phenylarsenical Metabolites Discovered in Chicken Liver |
title | Methylated Phenylarsenical Metabolites Discovered in Chicken Liver |
title_full | Methylated Phenylarsenical Metabolites Discovered in Chicken Liver |
title_fullStr | Methylated Phenylarsenical Metabolites Discovered in Chicken Liver |
title_full_unstemmed | Methylated Phenylarsenical Metabolites Discovered in Chicken Liver |
title_short | Methylated Phenylarsenical Metabolites Discovered in Chicken Liver |
title_sort | methylated phenylarsenical metabolites discovered in chicken liver |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5573966/ https://www.ncbi.nlm.nih.gov/pubmed/28470989 http://dx.doi.org/10.1002/anie.201700736 |
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