The DOI matches its Crossref record; 7 of the 7 references it cites were found in a registry or an index.
Occurrence, Synthesis, and Mammalian Cell Cytotoxicity and Genotoxicity of Haloacetamides: An Emerging Class of Nitrogenous Drinking Water Disinfection Byproducts
Abstract
The haloacetamides, a class of emerging nitrogenous drinking water disinfection byproduct (DBPs), were analyzed for their chronic cytotoxicity and for the induction of genomic DNA damage in Chinese hamster ovary cells. The rank order for cytotoxicity of 13 haloacetamides was DIAcAm > IAcAm > BAcAm > TBAcAm > BIAcAm > DBCAcAm > CIAcAm > BDCAcAm > DBAcAm > BCAcAm > CAcAm > DCAcAm > TCAcAm. The rank order of their genotoxicity was TBAcAm > DIAcAm ≈ IAcAm > BAcAm > DBCAcAm > BIAcAm > BDCAcAm > CIAcAm > BCAcAm > DBAcAm > CAcAm > TCAcAm. DCAcAm was not genotoxic. Cytotoxicity and genotoxicity were primarily determined by the leaving tendency of the halogens and followed the order I > Br >> Cl. With the exception of brominated trihaloacetamides, most of the toxicity rank order was consistent with structure–activity relationship expectations. For di- and trihaloacetamides, the presence of at least one good leaving halogen group (I or Br but not Cl) appears to be critical for significant toxic activity. Log P was not a factor for monohaloacetamides but may play a role in the genotoxicity of trihaloacetamides and possible activation of dihaloacetamides by intracellular GSH and -SH compounds. With the advent of the U.S. EPA Stage 2 DBP regulations, water utilities are considering the use of disinfectants that are alternatives to chlorine. The use of these alternative disinfectants will shift the distribution of DBP chemical classes. The emergence of new, highly toxic iodinated, nitrogenous DBPs, as illustrated by the discovery of bromoiodoacetamide as a new DBP, underscores the importance of comparative toxicity studies to assist in the overall goal of safer drinking water practice.
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Cites
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Self-citationOccurrence of a new generation of disinfection byproducts†
Krasner, S. W., Weinberg, H. S., Richardson, S. D., Pastor, S. J., Chinn, R., Sclimenti, M. J., Onstad, G. D., & Thruston, A. D. (2006) · Environmental Science & Technology · doi:10.1021/es060353j · Cited by 1,633
Self-citationHaloacetonitriles vs. Regulated Haloacetic Acids: Are Nitrogen-Containing DBPs More Toxic?
Muellner, M. G., Wagner, E. D., McCalla, K., Richardson, S. D., Woo, Y.-T., & Plewa, M. J. (2007) · Environmental Science & Technology · doi:10.1021/es0617441 · Cited by 751
Self-citationTrihalomethanes in Drinking Water and Spontaneous Abortion
Waller, K., Swan, S. H., DeLorenze, G., & Hopkins, B. (1998) · Epidemiology · doi:10.1097/00001648-199803000-00006 · Cited by 434
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
Assessment of lifetime exposure to trihalomethanes through different routes
Villanueva, C. M., Cantor, K. P., Grimalt, J. O., Castaño-Vinyals, G., Malats, N., Silverman, D., Tardon, A., Garcia-Closas, R., Serra, C., Carrato, A., et al. (2006) · Occupational and Environmental Medicine · doi:10.1136/oem.2005.023069 · Cited by 71
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Cited by
Occurrence and Mammalian Cell Toxicity of Iodinated Disinfection Byproducts in Drinking Water
Richardson, S. D., Fasano, F., Ellington, J. J., Crumley, F. G., Buettner, K. M., Evans, J. J., Blount, B. C., Silva, L. K., Waite, T. J., Luther, G. W., et al. (2008) · Environmental Science & Technology · doi:10.1021/es801169k · Cited by 655
Self-citationLi, L., Gao, N., Deng, Y., Yao, J., & Zhang, K. (2012) · Water Research · doi:10.1016/j.watres.2011.12.026 · Cited by 485
Richardson, S. D., DeMarini, D. M., Kogevinas, M., Fernandez, P., Marco, E., Lourencetti, C., Ballesté, C., Heederik, D., Meliefste, K., McKague, A. B., et al. (2010) · Environmental Health Perspectives · doi:10.1289/ehp.1001965 · Cited by 327
Self-citationVillanueva, C. M., Kogevinas, M., Cordier, S., Templeton, M. R., Vermeulen, R., Nuckols, J. R., Nieuwenhuijsen, M. J., & Levallois, P. (2014) · Environmental Health Perspectives · doi:10.1289/ehp.1206229 · Cited by 256
Drinking water treatment response following a Colorado wildfire
Hohner, A. K., Cawley, K., Oropeza, J., Summers, R. S., & Rosario-Ortiz, F. L. (2016) · Water Research · doi:10.1016/j.watres.2016.08.034 · Cited by 141
Metadata
- Authors
- Plewa, M. J., Muellner, M. G., Richardson, S. D., Fasano, F., Buettner, K. M., Woo, Y.-T., McKague, A. B., & Wagner, E. D.
- Venue
- Environmental Science & Technology
- Publisher
- American Chemical Society (ACS)
- Published
- 2007-12-12
- Volume
- 42
- Issue
- 3
- Pages
- 955-961
- ISSN
- 0013-936X (ISSN-L)
- 1520-5851
- OpenAlex
- W2035651035
- Cited by
- 556
- References
- 7
- FWCI
- 5.21
- Type
- journal article
- Language
- en
- Open access
- closed
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