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Analytical and Toxicological Characterization of Novel Nitrogen Containing Disinfection Byproducts Open Access


Other title
Disinfection byproducts
Mass spectrometry
Analytical chemistry
In vitro toxicology
Type of item
Degree grantor
University of Alberta
Author or creator
Boyd, Jessica M.
Supervisor and department
Le, X. Chris (Laboratory Medicine and Pathology)
Li, Xing-Fang (Laboratory Medicine and Pathology)
Examining committee member and department
Acker, Jason (Laboratory Medicine and Pathology)
Leslie, Elaine (Physiology)
Lucy, Chuck (Chemistry)
Martin, Jonathan (Laboratory Medicine and Pathology)
Siu, Michael (Chemistry, York University)
Medical Sciences- Laboratory Medicine and Pathology

Date accepted
Graduation date
Doctor of Philosophy
Degree level
Disinfection byproducts (DBPs) are an unwanted consequence of water disinfection. Consumption of chlorinated drinking water has been associated with an increased risk of bladder cancer; however, the DBP or DBPs responsible has not been identified. The N-nitrosamines are a class of DBPs that are known rodent carcinogens. They are more potent than the currently regulated DBPs and may be capable of causing health effects at low ng/L concentrations. Due to these possible health concerns, the study of nitrosamines in drinking water is warranted. Gas chromatography mass spectrometry (GC-MS) is the main technique used for nitrosamine analysis, but cannot directly detect thermally unstable or non-volatile nitrosamines. A liquid chromatography tandem MS (LC-MS/MS) method was developed that is capable of detecting GC-detectable nitrosamines, such as N-nitrosodimethylamine (NDMA), and GC-non-detectable nitrosamines. Using this method, N-nitrosodiphenylamine (NDPhA), a thermally unstable nitrosamine, was detected as a DBP from an authentic drinking water sample. A survey of 38 North American drinking water systems using the LC-MS/MS method found that NDMA was the most commonly detected nitrosamine (28 of 38 systems) followed by NDPhA (6 of 38 systems). A real-time cell electronic sensing (RT-CES) technique was developed and demonstrated as a useful tool for DBP toxicity testing. NDPhA was more cytotoxic than NDMA in four cell lines. Further mechanistic analysis determined that NDPhA induces cell cycle arrest, which is different than other nitrosamines such as NDMA. Studies on nitrosamine formation showed the important role of source water. Disinfectant type alone was not sufficient to determine which nitrosamines are formed. Additional studies determined that diphenylamine (DPhA) can form NDPhA, particularly in the presence of monochloramine. This reaction also formed phenazine and N-chlorophenazine. Further investigation determined that phenazine containing natural products produced by bacteria are also precursors for the phenazine containing DBPs. These results suggest that the currently monitored nitrosamines are not widespread enough to be solely responsible for the observed increase in bladder cancer risk. However, there are several locations where elevated nitrosamine concentrations are a concern. Until the DBP cancer culprit is identified, reduction of overall DBP formation through source water management and careful monitoring of the disinfection process is the best practice to manage cancer risks posed by DBPs.
Permission is hereby granted to the University of Alberta Libraries to reproduce single copies of this thesis and to lend or sell such copies for private, scholarly or scientific research purposes only. Where the thesis is converted to, or otherwise made available in digital form, the University of Alberta will advise potential users of the thesis of these terms. The author reserves all other publication and other rights in association with the copyright in the thesis and, except as herein before provided, neither the thesis nor any substantial portion thereof may be printed or otherwise reproduced in any material form whatsoever without the author's prior written permission.
Citation for previous publication
Zhao, Y.Y., Boyd, J., Hrudey, S.E., Li, X.-F. (2006). Characterization of new nitrosamines in drinking water using liquid chromatography tandem mass spectrometry. Environ. Sci. Technol. 40: 7636-7641.Boyd, J.M., Huang, L., Xie, L., Moe, B., Gabos, S., Hrudey, S., Li, X.-F. (2008). A cell-microelectronic sensing technique for profiling cytotoxicity of chemicals. Anal. Chim. Acta. 615(1): 80-87.Zhao, Y.Y., Boyd, J.M., Woodbeck, M., Andrews, R., Qin, F., Hrudey, S.E., Li, X.-F. (2008). Formation of N-nitrosamines from eleven disinfection treatments of seven different surface waters. Environ. Sci. Technol. 42(13): 4857-4862.Zhou, WJ, Boyd, J.M., Qin F., Hrudey, S.E., Li, X.-F. (2009) Formation of N-nitrosodiphenylamine and two new N-containing disinfection byproducts from choramination of water containing diphenylamine. Environ. Sci. Technol. 43(21): 8443-8448.Boyd, J.M., Hrudey, S.E., Li, X-F., Richardson, S.D. (2011) Solid-phase extraction and high-performance liquid chromatography mass spectrometry analysis of nitrosamines in treated drinking water and wastewater. TrAC. 30(9):1410-1421.Boyd, J.M., Zhao, Y.Y., Wagner, M, Qin, F., Levallois, P., Legay, C., Charrois, J.W.A., Richardson, S.D., Hrudey, S.E., Li, X.F. Liquid chromatography-tandem mass spectrometry determination of N-nitrosodiphenylamine and N-nitrosodimethylamine in thirty-eight drinking water systems. Proceedings of the International Water Association’s Biannual Water Congress, Montreal, Quebec Sept 2010.

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