Analytical and Biological Characterization of Halogenated Gemfibrozil Produced through Chlorination of Wastewater

详细信息    查看全文

• 作者：Daryl N. Bulloch ; Ramon Lavado ; Kristy L. Forsgren ; Szabolcs Beni ; Daniel Schlenk ; Cynthia K. Larive
• 刊名：Environmental Science & Technology (ES&T)
• 出版年：2012
• 出版时间：May 15, 2012
• 年：2012
• 卷：46
• 期：10
• 页码：5583-5589
• 全文大小：301K
• 年卷期：v.46,no.10(May 15, 2012)
• ISSN：1520-5851

文摘

The cholesterol-lowering pharmaceutical gemfibrozil is a relevant environmental contaminant because of its frequency of detection in U.S. wastewaters at concentrations which have been shown to disrupt endocrine function in aquatic species. The treatment of gemfibrozil solutions with sodium hypochlorite yielded a 4鈥?chlorinated gemfibrozil analog (chlorogemfibrozil). In the presence of bromide ion, as is often encountered in municipal wastewater, hypobromous acid generated through a halogen exchange reaction produced an additional 4鈥?brominated gemfibrozil product (bromogemfibrozil). Standards of chloro- and bromogemfibrozil were synthesized, isolated and characterized using mass spectrometry and NMR spectroscopy. Mass spectrometry was used to follow the in situ halogenation reaction of gemfibrozil in deionized water and wastewater matrices, and to measure levels of gemfibrozil (254 卤 20 ng/L), chlorogemfibrozil (166 卤 121 ng/L), and bromogemfibrozil (50 卤 11 ng/L) in advanced primary wastewater treatment effluent treated by chlorination. Chlorogemfibrozil demonstrated a significant (p < 0.05) reduction in the levels of 11-ketotestosterone at 55.1 渭g/L and bromogemfibrozil demonstrated a significant (p < 0.05) reduction in the levels of testosterone at 58.8 渭g/L in vivo in Japanese medaka in a 21 day exposure. These results indicated that aqueous exposure to halogenated degradates of gemfibrozil enhanced the antiandrogenicity of the parent compound in a model fish species, demonstrating that chlorination may increase the toxicity of pharmaceutically active compounds in surface water.