Use of orbitrap-MS/MS and QSAR analyses to estimate mutagenic transformation products of iopamidol generated during ozonation and chlorination

Chemosphere

Volumn 148, Issue , 2016, Pages 233-240

  Matsushita, Taku ^a   Hashizuka, Masahiro ^a   Kuriyama, Taisuke ^a   Matsui, Yoshihiko ^a   Shirasaki, Nobutaka ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Ames assay; Disinfection by product; Drinking water treatment; Mutagenicity; X ray contrast medium

Indexed keywords

CARBONYL COMPOUNDS; CHLORINATION; CHROMATOGRAPHIC ANALYSIS; COMPUTATIONAL CHEMISTRY; CONTRAST MEDIA; OZONE WATER TREATMENT; OZONIZATION; POSITIVE IONS; POTABLE WATER; PROPIONIC ACID; X RAYS;

AMES ASSAY; CONTRAST MEDIUM; DISINFECTION BY-PRODUCT; MUTAGENICITY; POSITIVE CORRELATIONS; QUANTITATIVE STRUCTURE ACTIVITY RELATIONSHIP; TRANSFORMATION PRODUCTS; WATER PURIFICATION;

OZONE;

IOPAMIDOL; CHLORINE; MUTAGENIC AGENT; OZONE; WATER POLLUTANT;

BIOASSAY; CHLORINATION; DISINFECTION; DRINKING WATER; DRUG; MEASUREMENT METHOD; MUTAGENICITY; OZONE; TRANSFORMATION; WATER TREATMENT; X-RAY SPECTROSCOPY;

ARTICLE; CHEMICAL STRUCTURE; CHLORINATION; METABOLIC ACTIVATION; MOLECULAR WEIGHT; MUTAGENICITY; OZONATION; QUANTITATIVE STRUCTURE ACTIVITY RELATION; SOLID PHASE EXTRACTION; TANDEM MASS SPECTROMETRY; WATER MANAGEMENT; CHEMISTRY; DRUG EFFECTS; GENETICS; HALOGENATION; LIQUID CHROMATOGRAPHY; MUTAGEN TESTING; PROCEDURES; SALMONELLA ENTERICA SEROVAR TYPHIMURIUM; TOXICITY; WATER POLLUTANT;

CHLORINE; CHROMATOGRAPHY, LIQUID; HALOGENATION; IOPAMIDOL; MUTAGENICITY TESTS; MUTAGENS; OZONE; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; SALMONELLA TYPHIMURIUM; SOLID PHASE EXTRACTION; TANDEM MASS SPECTROMETRY; WATER POLLUTANTS, CHEMICAL; WATER PURIFICATION;

EID: 84960365478     PISSN: 00456535     EISSN: 18791298     Source Type: Journal    
DOI: 10.1016/j.chemosphere.2016.01.037     Document Type: Article

References (26)

1. Bruchet A., Hochereau C., Picard C., Decottignies V., Rodrigues J.M., Janex-Habibi M.L. Analysis of drugs and personal care products in French source and drinking waters: the analytical challenge and examples of application. Water Sci. Technol. 2005, 52:53-61.
2. Busetti F., Linge K.L., Rodriguez C., Heitz A. Occurrence of iodinated X-ray contrast media in indirect potable reuse systems. J. Environ. Sci. Health, Part A 2010, 45:542-548.
3. Christiansen C. X-ray contrast media-an overview. Toxicology 2005, 209:185-187.
4. Duirk S.E., Lindell C., Cornelison C.C., Kormos J., Ternes T.A., Attene-Ramos M., Osiol J., Wagner E.D., Plewa M.J., Richardson S.D. Formation of toxic iodinated disinfection by-products from compounds used in medical imaging. Environ. Sci. Technol. 2011, 45:6845-6854.
5. ECHA Guidance on Information Requirements and Chemical Safety Assessment Chapter R.7a: Endpoint Specific Guidance 2008, http://echa.europa.eu/reach_en.asp.
6. Hainfeld J.F., Slatkin D.N., Focella T.M., Smilowitz H.M. Gold nanoparticles: a new X-ray contrast agent. Br. J. Radiol. 2006, 79:248-253.
7. Hansen K., Mika S., Schroeter T., Sutter A., ter Laak A., Steger-Hartmann T., Heinrich N., Müller K.-R. Benchmark data set for in silico prediction of Ames mutagenicity. J. Chem. Inf. Model. 2009, 49:2077-2081.
8. Haworth S., Lawlor T., Mortelmans K., Speck W., Zeiger E. Salmonella mutagenicity test results for 250 chemicals. Environ. Mutagen. 1983, 5:3-49.
9. Huber M.M., GÖbel A., Joss A., Hermann N., LÖffler D., McArdell C.S., Ried A., Siegrist H., Ternes T.A., von Gunten U. Oxidation of pharmaceuticals during ozonation of municipal wastewater effluents: a pilot study. Environ. Sci. Technol. 2005, 39:4290-4299.
10. Kazius J., McGuire R., Bursi R. Derivation and validation of toxicophores for mutagenicity prediction. J. Med. Chem. 2004, 48:312-320.
11. Kormos J.L., Schulz M., Kohler H.-P.E., Ternes T.A. Biotransformation of selected iodinated X-ray contrast media and characterization of microbial transformation pathways. Environ. Sci. Technol. 2010, 44:4998-5007.
12. Kormos J.L., Schulz M., Ternes T.A. Occurrence of iodinated X-ray contrast media and their biotransformation products in the urban water cycle. Environ. Sci. Technol. 2011, 45:8723-8732.
13. Matsushita T., Kobayashi N., Hashizuka M., Sakuma H., Kondo T., Matsui Y., Shirasaki N. Changes in mutagenicity and acute toxicity of solutions of iodinated X-ray contrast media during chlorination. Chemosphere 2015, 135:101-107.
14. Mckinstry D.N., Rommel A.J., Sugerman A.A. Pharmacokinetics, metabolism, and excretion of iopamidol in healthy subjects. Investig. Radiol. 1984, 19:S171-S174.
15. Pérez S., Barceló D. Fate and occurrence of X-ray contrast media in the environment. Anal. Bioanal. Chem. 2007, 387:1235-1246.
16. Pauwels B., Verstraete W. The treatment of hospital wastewater: an appraisal. J. Water Health 2006, 4:405-416.
17. Plewa M.J., Wagner E.D., Richardson S.D., Thruston A.D., Woo Y.-T., McKague A.B. Chemical and biological characterization of newly discovered iodoacid drinking water disinfection byproducts. Environ. Sci. Technol. 2004, 38:4713-4722.
18. 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., McKague A.B., Miltner R.J., Wagner E.D., Plewa M.J. Occurrence and mammalian cell toxicity of iodinated disinfection byproducts in drinking water. Environ. Sci. Technol. 2008, 42:8330-8338.
19. Seitz W., Jiang J.-Q., Schulz W., Weber W.H., Maier D., Maier M. Formation of oxidation by-products of the iodinated X-ray contrast medium iomeprol during ozonation. Chemosphere 2008, 70:1238-1246.
20. Seitz W., Weber W.H., Jiang J.-Q., Lloyd B.J., Maier M., Maier D., Schulz W. Monitoring of iodinated X-ray contrast media in surface water. Chemosphere 2006, 64:1318-1324.
21. Simazaki D., Kubota R., Suzuki T., Akiba M., Nishimura T., Kunikane S. Occurrence of selected pharmaceuticals at drinking water purification plants in Japan and implications for human health. Water Res. 2015, 76:187-200.
22. Ternes T.A., Bonerz M., Herrmann N., Teiser B., Andersen H.R. Irrigation of treated wastewater in Braunschweig, Germany: an option to remove pharmaceuticals and musk fragrances. Chemosphere 2007, 66:894-904.
23. Ternes T.A., Hirsch R. Occurrence and behavior of X-ray contrast media in sewage facilities and the aquatic environment. Environ. Sci. Technol. 2000, 34:2741-2748.
24. Ternes T.A., Stüber J., Herrmann N., McDowell D., Ried A., Kampmann M., Teiser B. Ozonation: a tool for removal of pharmaceuticals, contrast media and musk fragrances from wastewater?. Water Res. 2003, 37:1976-1982.
25. Wendel F.M., Lütke Eversloh C., Machek E.J., Duirk S.E., Plewa M.J., Richardson S.D., Ternes T.A. Transformation of iopamidol during chlorination. Environ. Sci. Technol. 2014, 48:12689-12697.
26. Zeiger E. Carcinogenicity of mutagens: predictive capability of the salmonella mutagenesis assay for rodent carcinogenicity. Cancer Res. 1987, 47:1287-1296.