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.

海南lamp（Petromyzon marinus）是大湖地区的一种破坏性入侵物种，在1900年代中期导致本地鱼类种群崩溃。3-三氟甲基-4-硝基苯酚（TFM）是一种选择性杀虫剂，自1960年代以来就已应用于五大湖中受海角rey侵染的支流，杀死幼虫，并减少了90％的人口。然而，海藻类和非目标物种对TFM的代谢尚未完全阐明。阐明TFM代谢对于理解其作用方式和可能的环境影响至关重要。在这里，我们描述了从海lamp鱼和三种非目标物种的肝脏中TFM代谢物的筛选，鉴定，合成和结构表征，它们在TFM暴露中生存能力不同。我们确定了葡萄糖醛酸化，硫酸化，N-乙酰化，谷胱甘肽共轭和芳香族硝基还原作为潜在的排毒机制。合成了七种代谢物，用作鱼类中TFM代谢的标志物。定量的¹ H NMR用于分析合成的代谢物储备溶液，然后将其用作标准材料以开发用于TFM代谢物的定量LC-MS / MS方法。