Chemical and biological characterization of newly discovered iodoacid drinking water disinfection byproducts

Environmental Science and Technology

Volumn 38, Issue 18, 2004, Pages 4713-4722

  Plewa, Michael J ^a   Wagner, Elizabeth D ^a   Richardson, Susan D ^b   Thruston Jr , Alfred D ^b   Woo, Yin Tak ^b   McKague, A Bruce ^c  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

^b U S ENVIRONMENTAL PROTECTION AGENCY   (United States)

^c CanSyn Chem Corp   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; BYPRODUCTS; CELLS; DISINFECTION; ORGANIC ACIDS; TOXICITY;

CYTOTOXICITY; DISINFECTION BYPRODUCTS (DBP); IODOACID DRINKING WATER; MONOHALOGENATED ACETIC ACIDS;

POTABLE WATER;

ACETIC ACID DERIVATIVE; ACID; ACRYLIC ACID DERIVATIVE; BROMOACETIC ACID; CHLOROACETIC ACID; DRINKING WATER; IODOACETIC ACID; IODOACID; UNCLASSIFIED DRUG;

CHEMICAL ANALYSIS; DISINFECTION; DRINKING WATER;

ANIMAL CELL; ARTICLE; BACTERIAL STRAIN; BROMINATION; CHLORINATION; CHO CELL; CONTROLLED STUDY; CORRELATION ANALYSIS; CYTOTOXICITY; DISINFECTION; GENOTOXICITY; HALOGENATION; MAMMAL CELL; NONHUMAN; SALMONELLA TYPHIMURIUM; SAMPLE; STRUCTURE ANALYSIS; WATER CONTAMINATION; WATER QUALITY;

ACETIC ACIDS; ANIMALS; CHLORAMINES; CHO CELLS; CRICETINAE; CRICETULUS; DISINFECTANTS; DISINFECTION; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HUMANS; IODIDES; IODOACETIC ACID; ISOMERISM; MUTAGENICITY TESTS; SALMONELLA TYPHIMURIUM; WATER POLLUTANTS, CHEMICAL; WATER PURIFICATION; WATER SUPPLY;

ANIMALIA; BACTERIA (MICROORGANISMS); CRICETINAE; CRICETULUS GRISEUS; MAMMALIA; SALMONELLA TYPHIMURIUM;

EID: 4544226414     PISSN: 0013936X     EISSN: None     Source Type: Journal    
DOI: 10.1021/es049971v     Document Type: Article

References (54)

1. U.S. EPA. Municipal drinking water disinfection; U.S. Government Printing Office: Washington, DC, 1992; EPA/625/1-92/021.
2. Minear, R. A.; Amy, G. L. Disinfection By-Products in Water Treatment: The Chemistry of Their Formation and Control; Lewis Publishers: Boca Raton, FL, 1996.
3. Richardson, S. D. Drinking Water Disinfection By-products. In The Encyclopedia of Environmental Analysis and Remediation; John Wiley & Sons: New York, 1998; Vol. 3, p 1398.
4. Betts, K. Growing concern about disinfection byproducts. Environ. Sci. Technol. 1998, 32, 546.
5. Richardson, S. D.; Simmons, J. E.; Rice, G. Disinfection byproducts: the next generation. Environ. Sci. Technol. 2002, 36, 1198A.
6. Morris, R. D.; Audet, A. M.; Angelillo, I. F.; Chalmers, T. C.; Mosteller, F. Chlorination, chlorination by-products and cancer: a meta-analysis. Am. J. Public Health 1992, 82, 955.
7. Koivusalo, M.; Jaakkola, J. J. K.; Vartiainen, T.; Hakulinen, T.; Karjalainen, S.; Pukkala, E.; Tuomisto, J. Drinking water mutagenicity and gastrointestinal and urinary tract cancers: an ecological study in Finland. Am J. Public Health 1994, 84, 1223.
8. Bull, R. J.; Birnbaum, L. S.; Cantor, K.; Rose, J.; Butterworth: B. E.; Pegram, R.; Tuomisto, J. Water chlorination: essential process or cancer hazard? Fundam. Appl. Toxicol. 1995, 28, 155.
9. Swan, S. H.; Neutra, R. R.; Wrensch, M.; Hertz-Picciotto, I.; Windham, G. C.; Fenster, L.; Epstein, D. M.; Deane, M. Is drinking water related to spontaneous abortion? Reviewing the evidence from the California Department of Health Services studies. Epidemiology 1992, 3, 83.
10. Waller, K.; Swan, S. H.; Windham, S. C.; Fenster, L. Influence of exposure assessment methods on risk estimates in an epidemiologic study of total trihalomethane exposure and spontaneous abortion. J. Exp. Anal. Environ. Epidemiol. 2001, 11, 522.
11. Weinberg, H. Disinfection byproducts in drinking water: the analytical challenge. Anal. Chem. 1999, 71, 801A.
12. Stevens, A. A.; Moore, L. A.; Slocum, C. J.; Smith, B. L.; Seeger, D. R.; Ireland, J. C. In Disinfection By-Products: Current Perspectives; American Water Works Association: Denver, CO, 1989.
13. Krasner, S. W.; Chinn, R.; Hwang, C. J.; Barrett, S. E. Proceedings of the 1990 American Water Works Association Water Quality Technology Conference; American Water Works Association: Denver, CO, 1991.
14. Zhang, X.; Echigo, S.; Minear, R. A.; Plewa, M. J. Characterization and comparison of disinfection by-products of four major disinfectants. In Natural Organic Matter and Disinfection Byproducts; American Chemical Society: Washington, DC, 2000; p 299.
15. Richardson, S. D.; Thruston, A. D., Jr.; Rav-Acha, C.; Groisman, L.; Popilevsky, I.; Juraev, O.; Glezer, V.; McKague, A. B.; Plewa, M. J.; Wagner, E. D. Tribromopyrrole, brominated acids, and other disinfection byproducts produced by disinfection of drinking water rich in bromide. Environ. Sci. Technol. 2003, 37, 3782.
16. McCulloch, A. Trichloroacetic acid in the environment. Chemosphere 2002, 47, 667.
17. Krasner, S. W.; McGuire, M. J.; Jacangelo, J. G.; Patania, N. L.; Reagan, K. M.; Aieta, E. M. The occurrence of disinfection byproducts in USA drinking water. J. Am. Water Works Assoc. 1989, 81 (8), 41.
18. Richardson, S. D.; Thruston, A. D., Jr.; Caughran, T. V.; Chen, P. H.; Collette, T. W.; Floyd, T. L.; Schenck, K. M.; Lykins, B. W., Jr.; Sun, G.-R.; Majetich, G. Identification of new drinking water disinfection byproducts formed in the presence of bromide. Environ. Sci. Technol. 1999, 33, 3378.
19. Giller, S.; Le Crieux, F.; Erb, F.; Marzin, D. Comparative genotoxicity of halogenated acetic acids found in drinking water. Mutagenesis 1997, 12, 321.
20. Nelson, M. A.; Bull, R. J. Induction of strand breaks in DNA by trichloroethylene and metabolites in rat and mouse liver in vivo. Toxicol. Appl. Pharmacol. 1988, 94, 45.
21. Kargalioglu, Y.; McMillan, B. J.; Minear, R. A.; Plewa, M. J. An analysis of the cytotoxicity and mutagenicity of drinking water disinfection by-products in Salmonella typhimurium. Teratog. Carcinog. Mutagen. 2002, 22, 113.
22. Plewa, M. J.; Kargalioglu, Y.; Vankerk, D.; Minear, R. A.; Wagner, E. D. Mammalian cell cytotoxicity and genotoxicity analysis of drinking water disinfection by-products. Environ. Mol. Mutagen. 2002, 40, 134.
23. Weinberg, H. S.; Krasner, S. W.; Richardson, S. D.; Thruston, A. D., Jr. The Occurrence of Disinfection By-Products (DBPs) of Health Concern in Drinking Water: Results of a Nationwide DBP Occurrence Study, U.S. Environmental Protection Agency, National Exposure Research Laboratory: Athens, GA, 2002; EPA/600/R-02/068; www.epa.gov/athens/publications/EPA_600_R02_068.pdf.
24. Hunter, E. S., III; Tugman, J. A. Inhibitors of glycolytic metabolism affect neurulation-staged mouse conceptuses in vitro. Teratology 1995, 52, 317.
25. Hunter, E. S., III; Rogers, E. H.; Schmid, J. E.; Richard, A. Comparative effects of haloacetic acids in whole embryo culture. Teratology 1996, 54, 57.
26. Cobb, R. L. Synthesis and properties of triiodoacetic acid and its salts. J. Org. Chem. 1958, 23, 1368.
27. Strauss, F.; Kollek, L.; Heyn, W. Replacement of positive hydrogen by halogen. I. Ber. 1930, 63, 1868.
28. Andersson, K. Addition of halogens to propiolic and tetrolic acid. Chem. Scr. 1972, 2, 117.
29. Baldwin, J. E.; Beyeler, A.; Cox, R. J.; Keats, C.; Pritchard, G. J.; Adlington, R. M.; Watkins, D. J. Reinvestigation of the dimerisation process forming isoglaucanic acid. Tetrahedron 1999, 55, 7363.
30. Maron, D. M.; Ames, B. N. Revised methods for the Salmonella mutagenicity test. Mutat. Res. 1983, 113, 173.
31. Wagner, E. D.; Rayburn, A. L.; Anderson, D.; Plewa, M. J. Analysis of mutagens with single cell gel electrophoresis, flow cytometry, and forward mutation assays in an isolated clone of Chinese hamster ovary cells. Environ. Mol. Mutagen. 1998, 32, 360.
32. Plewa, M. J.; Wagner, E. D.; Jazwierska, P.; Richardson, S. D.; Chen, P. H.; McKague, A. B. Halonitromethane drinking water disinfection byproducts: chemical characterization and mammalian cell cytotoxicity and genotoxicity. Environ. Sci. Technol. 2004, 38, 62.
33. Henderson, L.; Wolfreys, A.; Fedyk, J.; Bowmer, C.; Windebank, S. The ability of the comet assay to discriminate between genotoxins and cytotoxins. Mutagenesis 1998, 13, 89.
34. Box, G. E. P.; Hunter, W. G.; Hunter, J. S. Statistics for Experimenters: An Introduction to Design, Data Analysis, and Model Building; John Wiley & Sons: New York, 1978.
35. Lovell, D. P.; Thomas, G.; Dubow, R. Issues related to the experimental design and subsequent statistical analysis of in vivo and in vitro Comet studies. Teratog. Carcinog. Mutagen. 1999, 19, 109.
36. Bichsel, Y.; von Gunten, U. Oxidation of iodide and hypoiodous acid in the disinfection of natural waters. Environ. Sci. Technol. 1999, 33, 4040.
37. Bichsel, Y.; von Gunten, U. Formation of iodo-trihalomethanes during disinfection and oxidation of iodide containing waters. Environ. Sci. Technol. 2000, 34, 2784.
38. Xu, X.; Mariano, T. M.; Laskin, J. D.; Weisel, C. P. Percutaneous absorption of trihalomethanes, haloacetic acids, and haloketones. Toxicol. Appl. Pharmacol. 2002, 184, 19.
39. Yoshikawa, M.; Shudo, S.; Sanui, K.; Ogata, N. Active transport of organic acids through poly(4-vinylpyridine-co-acrylonitrile) membranes. J. Membr. Sci. 1986, 26, 51.
40. Hayes, F. D.; Short, R. D.; Gibson, J. E. Differential toxicity of monochloroacetate, monofluoroacetateand monoiodoacetate in rats. Toxicol. Appl. Pharmacol. 1973, 26, 93.
41. Loudon, G. M. Organic Chemistry, 3rd ed.; Benjamin/Cummings Publishing Co.: Redwood, CA, 1995.
42. Richard, A. M.; Hunter, E. S., III. Quantitative structure-activity relationships for the developmental toxicity of haloacetic acids in mammalian whole embryo culture. Teratology 1996, 53, 352.
43. Woo, Y. T.; Arcos, J. C.; Lai, D. Y. Structural and functional criteria for assessing carcinogenic potential of chemicals; the state-of-the-art predictive formalism. In Handbook of Carcinogen Testing; Noyes Publishing: Park Ridge, NJ, 1985.
44. Higgins, T. J.; Bailey, P. J. The effects of cyanide and iodoacetate intoxication and ischaemia on enzyme release from the perfused rat heart. Biochim. Biophys. Acta 1983, 762, 67.
45. Andres, M. I.; Repetto, G.; Sanz, P.; Repetto, M. Comparative effects of the metabolic inhibitors 2,4-dinitrophenol and iodoacetate on mouse neuroblastoma cells in vitro. Toxicology 1996, 110, 123.
46. Lash, L. H.; Tokarz, J. J.; Chen, Z.; Pedrosi, B. M.; Woods, E. B. ATP depletion by iodoacetate and cyanide in renal distal tubular cells. J. Pharmacol. Exp. Ther. 1996, 276, 194.
47. Hilliard, C. A.; Armstrong, M. J.; Bradt, C. I.; Hill, R. B.; Greenwood, S. K.; Galloway, S. Chromosome aberrations in vitro related to cytotoxicity of nonmutagenic chemicals and metabolic poisons. Environ. Mol. Mittagen. 1998, 31, 316.
48. Chamberlain, M. P.; Lock, E. A.; Reed, C. J. Investigations of the pathways of toxicity of methyl iodide in the rat nasal cavity. Toxicology 1998, 129, 169.
49. Chamberlain, M. P.; Sturgess, N. C.; Lock, E. A.; Reed, C. J. Methyl iodide toxicity in rat cerebellar granule cells in vitro: the role of glutathione. Toxicology 1999, 139, 27.
50. Wilhelm, D.; Bender, K.; Knebel, A.; Angel, P. The level of intracellular glutathione is a key regulator for the induction of stress-activated signal transduction pathways including Jun N-terminal protein kinases and p38 kinase by alkylating agents. Mol. Cell. Biol. 1997, 17, 4792.
51. Gwynn, R. H.; Salaman, M. H. Studies on co-carcinogenesis, SH-reactors and other substances tested for co-carcinogenic action in mouse skin. Br. J. Cancer 1953, 7, 482.
52. NTP. Toxicology and Carcinogenesis Studies of Monochloroacetic Acid in F344IN Rats and B6C3F1 Mice (Gavage Studies); NTP Technical Report 396; National Toxicology Program: Research Triangle Park, NC, 1992.
53. IARC. Int. Agency Res. Monogr. 1999, No. 71, 1503.
54. Mansch, C.; Leo, A.; Hoekman, D. Exploring QSAR. Hydrophobic, Electronic and Steric Constants; American Chemical Society: Washington, DC, 1995.