Angewandte Chemie - International Edition
Angewandte Chemie - International Edition
5 years ago

Methylated Phenylarsenical Metabolites Discovered in Chicken Liver

Methylated Phenylarsenical Metabolites Discovered in Chicken Liver
Hanyong Peng, X. Chris Le, Bin Hu, Qingqing Liu, Hongquan Zhang, Jinhua Li, Xing-Fang Li
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 IC50 values of the trivalent phenylarsenical compounds were 300–30 000 times lower than those of the pentavalent phenylarsenicals. Toxic chicken: Three toxicologically relevant methylated phenylarsenical metabolites were detected in the liver of chickens fed 3-nitro-4-hydroxyphenylarsonic acid (roxarsone), a feed additive in poultry production that is still in use in several countries. These compounds are likely formed by methylation of trivalent phenylarsonous acid substrates in the presence of an arsenic methyltransferase.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201700736

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