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5353947 
Journal Article 
Metabolism of a sea lamprey pesticide by fish liver enzymes part A: identification and synthesis of TFM metabolites 
Bussy, U; Chung-Davidson, YW; Buchinger, T; Li, K; Smith, SA; Jones, AD; Li, W 
2018 
Yes 
Analytical and Bioanalytical Chemistry
ISSN: 1618-2642
EISSN: 1618-2650 
410 
6 
1749-1761 
English 
29282500 
WOS:000424643800013 
The sea lamprey (Petromyzon marinus) is a destructive invasive species in the Great Lakes that contributed to the collapse of native fish populations in the mid-1900s. 3-Trifluoromethyl-4-nitrophenol (TFM) is a selective pesticide that has been applied to sea lamprey infested tributaries of the Great Lakes to kill larvae since the 1960s and has reduced the populations by as much as 90%. However, the metabolism of TFM by sea lamprey and non-target species is not fully illuminated. Elucidation of TFM metabolism is critical for understanding its mode of action and possible environmental impact. Here, we describe the screening, identification, synthesis and structural characterization of TFM metabolites in livers from sea lamprey and three non-target species that differ in their ability to survive TFM exposure. We identified glucuronidation, sulfation, N-acetylation, glutathione conjugation, and aromatic nitro group reduction as potential detoxification mechanisms. Seven metabolites were synthesized for use as markers of TFM metabolism in fish. Quantitative 1H NMR was used to assay synthesized metabolite stock solutions that were then used as standard material to develop a quantitative LC-MS/MS method for TFM metabolites.