Analytical and biological characterization of halogenated gemfibrozil produced through chlorination of wastewater

Bulloch, D. N. and Lavado, R. and Forsgren, K. L. and Béni, Szabolcs and Schlenk, D. (2012) Analytical and biological characterization of halogenated gemfibrozil produced through chlorination of wastewater. Environmental Science and Technology, 46 (10). pp. 5583-5589. ISSN 0013-936X (print), 1520-5851 (online)

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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′-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′-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 ± 20 ng/L), chlorogemfibrozil (166 ± 121 ng/L), and bromogemfibrozil (50 ± 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 μg/L and bromogemfibrozil demonstrated a significant (p < 0.05) reduction in the levels of testosterone at 58.8 μg/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. © 2012 American Chemical Society.

Item Type: Article
Uncontrolled Keywords: Water Pollutants, Chemical; Waste Disposal, Fluid; Time Factors; particulate matter; Animals; waste water management; synthesis; sewage effluent; pollutant; Oryzias; nonhuman; in vivo study; Halogenation; Environmental impact; endocrine function; controlled study; ARTICLE; animal experiment; ADSORPTION; wastewater; TOXICITY; pollution exposure; pollution effect; nuclear magnetic resonance; Ion exchange; fishery modeling; fish; endocrine disruptor; DRUG; chlorite; testosterone; surface water; hypochlorite sodium; halogen; gemfibrozil; bromide ion; Effluents; Wastewater treatment; Nuclear magnetic resonance spectroscopy; Mass Spectrometry; Deionized water; CHLORINATION; Water and wastewater; Sodium hypochlorites; Primary wastewater treatment; Pharmaceutically active compounds; Parent compounds; Municipal wastewaters; Japanese medaka; IN-VIVO; IN-SITU; hypobromous acid; Halogen exchange; Gemfibrozils; Fish species; Environmental contaminant; Endocrine functions; Bromide ions; Biological characterization; aquatic species
Subjects: Q Science / természettudomány > QD Chemistry / kémia > QD01 Analytical chemistry / analitikai kémia
R Medicine / orvostudomány > RM Therapeutics. Pharmacology / terápia, gyógyszertan
T Technology / alkalmazott, műszaki tudományok > TD Environmental technology. Sanitary engineering / környezetvédelem, hulladékkezelés, egészségügyi mérnöki technika (ivóvízellátási és szennyvízkezelési technika)
Depositing User: MTMT SWORD
Date Deposited: 17 Feb 2016 14:53
Last Modified: 17 Feb 2016 14:53

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