Haloacetonitriles vs. Regulated Haloacetic Acids: Are Nitrogen-Containing DBPs More Toxic?
Abstract
Haloacetonitriles (HANs) are toxic nitrogenous drinking water disinfection byproducts (N-DBPs) and are observed with chlorine, chloramine, or chlorine dioxide disinfection. Using microplate-based Chinese hamster ovary (CHO) cell assays for chronic cytotoxicity and acute genotoxicity, we analyzed 7 HANs: iodoacetonitrile (IAN), bromoacetonitrile (BAN), dibromoacetonitrile (DBAN), bromochloroacetonitrile (BCAN), chloroacetonitrile (CAN), dichloroacetonitrile (DCAN), and trichloroacetonitrile (TCAN). The cytotoxic potency (%C1/2 values) ranged from 2.8 microM (DBAN) to 0.16 mM (TCAN), with a descending rank order of DBAN > IAN approximately BAN > BCAN > DCAN > CAN > TCAN. HANs induced acute genomic DNA damage; the single cell gel electrophoresis (SCGE) genotoxicity potency ranged from 37 microM (IAN) to 2.7 mM (DCAN). The rank order of declining genotoxicity was IAN > BAN approximately DBAN > BCAN > CAN > TCAN > DCAN. The accompanying structure-activity analysis of these HANs was in general agreement with the genotoxicity rank order. These data were incorporated into our growing quantitative comparative DBP cytotoxicity and genotoxicity databases. As a chemical class, the HANs are more toxic than regulated carbon-based DBPs, such as the haloacetic acids. The toxicity of N-DBPs may become a health concern because of the increased use of alternative disinfectants, such as chloramines, which may enhance the formation of N-DBPs, including HANs.
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UV irradiation promotes the formation of THMs and some nitrogenous DBPs which might be more toxic than carbon-based DBPs.
“However, UV irradiation promotes the formation of THMs and some nitrogenous DBPs (e.g., CH 3 NCl 2 , CNCHCl 2 , and CNCl) which might be more toxic than the carbon-based DBPs (Muellner et al., 2007;Weng et al., 2012;Weng et al., 2013).”
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Out of more than six hundred halogenation byproducts identified to date, only eleven are currently subject to strict EPA regulation.
“Strikingly, out of more than six hundred halogenation byproducts identified as of to date, only eleven are currently subject to strict EPA regulation (124).”
From Hypochlorous Acid: From Innate Immune Factor and Environmental Toxicant to Chemopreventive Agent Targeting Solar UV-Induced Skin Cancer (2022) · cites this paper as [124]
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Drinking water contaminants and adverse pregnancy outcomes: a review.
Bove, F., Shim, Y., & Zeitz, P. (2002) · Environmental Health Perspectives · doi:10.1289/ehp.02110s161 · Cited by 315 · see citing works
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RICHARDSON, S., PLEWA, M., WAGNER, E., SCHOENY, R., & DEMARINI, D. (2007) · Mutation Research/Reviews in Mutation Research · doi:10.1016/j.mrrev.2007.09.001 · Cited by 3,317 · see citing works
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Weaver, W. A., Li, J., Wen, Y., Johnston, J., Blatchley, M. R., & Blatchley III, E. R. (2009) · Water Research · doi:10.1016/j.watres.2009.04.035 · Cited by 172 · see citing works
Yang, L., Chen, X., She, Q., Cao, G., Liu, Y., Chang, V. W.-C., & Tang, C. Y. (2018) · Environment International · doi:10.1016/j.envint.2018.10.024 · Cited by 144 · see citing works
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Self-citationDeng, Y., Zhang, Y., Zhang, R., Wu, B., Ding, L., Xu, K., & Ren, H. (2014) · Environmental Science & Technology · doi:10.1021/es502010v · Cited by 91 · see citing works
Bradley, P. M., LeBlanc, D. R., Romanok, K. M., Smalling, K. L., Focazio, M. J., Cardon, M. C., Clark, J. M., Conley, J. M., Evans, N., Givens, C. E., et al. (2021) · Environment International · doi:10.1016/j.envint.2021.106487 · Cited by 43 · see citing works
Snell, J. A., Jandova, J., & Wondrak, G. T. (2022) · Frontiers in Oncology · doi:10.3389/fonc.2022.887220 · Cited by 37 · see citing works
- Authors
- Muellner, M. G., Wagner, E. D., McCalla, K., Richardson, S. D., Woo, Y.-T., & Plewa, M. J.
- Affiliations
- Environmental Protection Agency (US)
- Venue
- Environmental Science & Technology
- Publisher
- American Chemical Society (ACS)
- Published
- 2006-12-06
- Volume
- 41
- Issue
- 2
- Pages
- 645-651
- ISSN
- 0013-936X (ISSN-L)
- 1520-5851
- OpenAlex
- W2062929894
- Cited by
- 751
- References
- 1
- Citations by year
- 2026: 37 · 2025: 44 · 2024: 48 · 2023: 51 · 2022: 60 · 2021: 50 · 2020: 61 · 2019: 61 · 2018: 42 · 2017: 52 · 2016: 46 · 2015: 34 · 2014: 27 · 2013: 28 · 2012: 21
- FWCI
- 10.40
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Environmental Science & Technology (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Physical Sciences › Environmental Science › Health, Toxicology and Mutagenesis › Water Treatment and Disinfection
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Cancer Research › Carcinogens and Genotoxicity Assessment
- Physical Sciences › Environmental Science › Health, Toxicology and Mutagenesis › Environmental Toxicology and Ecotoxicology
- Keywords
- haloacetonitriles, drinking water disinfection by-products, haloacetic acids, cytotoxicity, genotoxicity, dibromoacetonitrile, trichloroacetonitrile, chloramines, chlorine disinfection, structure-activity relationship, comet assay, alternative disinfectants
- MeSH terms
- Acetates, Acetonitriles, Animals, Cell Count, Cricetulus, Disinfection, Electrophoresis, Cricetinae, Hydrocarbons, Halogenated, Mutagenicity Tests, Regression Analysis, Water Supply, CHO Cells, Water Purification, Quantitative Structure-Activity Relationship, Cell Proliferation
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