Qualitative environmental risk assessment of photolytic transformation products of iodinated X-ray contrast agent diatrizoic acid

Science of the Total Environment

Volumn 482-483, Issue 1, 2014, Pages 378-388

  Rastogi, Tushar ^a   Leder, Christoph ^a   Kümmerer, Klaus ^a  

^a LEUPHANA UNIVERSITY OF LÜNEBURG   (Germany)

Author keywords

Diatrizoic acid; Iodinated contrast media; Qualitative environmental risk assessment; Quantitative structure activity relationships (QSAR); US EPA PBT profiler

Indexed keywords

AEROBIC BIODEGRADABILITY; ENVIRONMENTAL RISK ASSESSMENT; IODINATED CONTRAST MEDIA; PHOTOLYTIC TRANSFORMATION; QUALITATIVE RISK ASSESSMENT; QUANTITATIVE RISK ASSESSMENT; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIPS; US EPA PBT PROFILER;

BIOACCUMULATION; BIOCHEMISTRY; BIODEGRADATION; BIOMOLECULES; DYES; ENVIRONMENTAL PROTECTION AGENCY; METABOLITES; MOLECULAR GRAPHICS;

RISK ASSESSMENT;

DIATRIZOATE; DRUG METABOLITE;

AQUATIC ECOSYSTEM; BIODEGRADATION; DRUG; ENVIRONMENTAL FATE; ENVIRONMENTAL RISK; METABOLITE; OXIC CONDITIONS; POLLUTION EXPOSURE; PROFILER; QUALITATIVE ANALYSIS; REGRESSION ANALYSIS; RISK ASSESSMENT; TOXICOLOGY; X-RAY;

AQUATIC ENVIRONMENT; ARTICLE; BIODEGRADATION; COMPUTER MODEL; COMPUTER PROGRAM; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; ECOTOXICOLOGY; GENOTOXICITY; MUTAGENICITY; PHOTODEGRADATION; PHOTOLYSIS; POLLUTION MONITORING; PRIORITY JOURNAL; QUALITATIVE ANALYSIS; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RISK ASSESSMENT;

DIATRIZOIC ACID; IODINATED CONTRAST MEDIA; QUALITATIVE ENVIRONMENTAL RISK ASSESSMENT; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIPS (QSAR); US EPA PBT PROFILER;

BIODEGRADATION, ENVIRONMENTAL; CONTRAST MEDIA; DIATRIZOATE; MODELS, CHEMICAL; PHOTOLYSIS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; RISK ASSESSMENT; WATER POLLUTANTS, CHEMICAL;

EID: 84897848777     PISSN: 00489697     EISSN: 18791026     Source Type: Journal    
DOI: 10.1016/j.scitotenv.2014.02.139     Document Type: Article

References (68)

1. Andreucci M., Fuiano G., Presta P., Esposito P., Faga T., Bisesti V., et al. Radiocontrast media cause dephosphorylation of Akt and downstream signaling targets in human renal proximal tubular cells. Biochem Pharmacol 2006, 72:1334-1342.
2. Arnold W.A., McNeill K. Transformation of pharmaceuticals in the environment: photolysis and other abiotic processes. Comprehensive analytical chemistry analysis, fate and removal of pharmaceuticals in the water cycle 2007, 361-385. Elsevier. M. Petrović, D. Barceló (Eds.).
3. Arnot J.A., Gobas F.A. A review of bioconcentration factor (BCF) and bioaccumulation factor (BAF) assessments for organic chemicals in aquatic organisms. Environ Rev 2006, 14:257-297.
4. Boxall A.B..A. Transformation products of synthetic chemicals in the environment 2009, Springer Berlin Heidelberg, Berlin, Heidelberg. 2nd ed.
5. Bryan R.N., Centeno R.S., Hershkowitz N., Poelstra R.J., Osato M.S. Neurotoxicity of iohexol: a new nonionic contrast medium. Radiology 1982, 145:379-382.
6. Chakravarti S.K., Saiakhov R.D., Klopman G. Optimizing predictive performance of case ultra expert system models using the applicability domains of individual toxicity alerts. J Chem Inf Model 2012, 52:2609-2618.
7. Chang H., Hu J., Wang L., Shao B. Occurrence of sulfonamide antibiotics in sewage treatment plants. Chin Sci Bull 2008, 53:514-520.
8. Clements R.G., Nabholz J.V., Johnson D.E., Zeeman M.G. The use of quantitative structure-activity relationships (qsars) as screening tools in environmental assessment. Environmental toxicology and risk assessment, 2nd volume 1993, 555-570. ASTM, Philadelphia. J.W. Gorsuch, J.F. Dwyer, C. Ingersoll, T.W. La Point (Eds.).
9. Dimitrov S., Dimitrova N., Parkerton T., Comber M., Bonnell M., Mekenyan O. Base-line model for identifying the bioaccumulation potential of chemicals. SAR QSAR Environ Res 2005, 16:531-554.
10. Dimitrov S., Dimitrova N., Georgieva D., Vasilev K., Hatfield T., Straka J., et al. Simulation of chemical metabolism for fate and hazard assessment. III. New developments of the bioconcentration factor base-line model. SAR QSAR Environ Res 2012, 23:17-36.
11. ECHA. Guidance on information requirements and chemical safety assessment - ECHA 2012. (accessed November 18, 2013). http://echa.europa.eu/web/guest/guidance-documents/guidance-on-information-requirements-and-chemical-safety-assessment.
12. Environmental Protection Agency Persistent bioaccumulative toxic (PBT) chemicals; lowering of reporting thresholds for certain PBT chemicals; addition of certain PBT chemicals; community right-to-know toxic chemical reporting 1999, Federal Register Environmental Documents USEPA.
13. Environmental Protection Agency Category for persistent, bioaccumulative, and toxic new chemical substances 1999, Federal Register Environmental Documents USEPA.
14. Escher B.I., Fenner K. Recent advances in environmental risk assessment of transformation products. Environ Sci Technol 2011, 45:3835-3847.
15. European Commission Technical guidance document on risk assessment part II 2003, [http://ec.europa.eu/environment/chemicals/exist_subst/pdf/tgdpart2_2ed.pdf].
16. European Commission Technical guidance document on risk assessment part III 2003, [http://echa.europa.eu/documents/10162/16960216/tgdpart3_2ed_en.pdf].
17. European Medicine Agency Guideline on the environmental risk assessment of medicinal products for human use 2005, [http://www.iss.it/binary/farm2/cont/guideline%20environmental%20risk%20assessment%20medicinal%20products.1109243627.pdf].
18. Fatta-Kassinos D., Meric S., Nikolaou A. Pharmaceutical residues in environmental waters and wastewater: current state of knowledge and future research. Anal Bioanal Chem 2011, 399:251-275.
19. Friedrich J., Längin A., Kümmerer K. Comparison of an electrochemical and luminescence-based oxygen measuring system for use in the biodegradability testing according to closed bottle test (OECD 301D). Clean-Soil, Air, Water 2013, 41:251-257.
20. Grönewäller E.F., Wahl H.G., Kehlbach R., Rodemann H.P., Claussen C.D., Duda S.H. Stabilität jodhaltiger röntgenkontrastmittel unter uv-laser-bestrahlung und toxizität der photoprodukte. Rofo 1998, 169:537-541.
21. Haiß A., Kümmerer K. Biodegradability of the X-ray contrast compound diatrizoic acid, identification of aerobic degradation products and effects against sewage sludge micro-organisms. Chemosphere 2006, 62:294-302.
22. Han G.H., Hur H.G., Kim S.D. Ecotoxicological risk of pharmaceuticals from wastewater treatment plants in Korea: occurrence and toxicity to daphnia magna. Environ Toxicol Chem 2006, 25:265-271.
23. Hapeshi E., Lambrianides A., Koutsoftas P., Kastanos E., Michael C., Fatta-Kassinos D. Investigating the fate of iodinated X-ray contrast media iohexol and diatrizoate during microbial degradation in an MBBR system treating urban wastewater. Environ Sci Pollut Res 2013, 20:3592-3606.
24. Harmon R.C., Duffy S.P., Terneus M.V., Ball J.G., Valentovic M.A. Characterization of a novel model for investigation of radiocontrast nephrotoxicity. Nephrol Dial Transplant 2009, 24:763-768.
25. Heberer T. Occurrence, fate, and removal of pharmaceutical residues in the aquatic environment: a review of recent research data. Toxicol Lett 2002, 131:5-17.
26. Hennebel T., de Corte S., Vanhaecke L., Vanherck K., Forrez I., de Gusseme B., et al. Removal of diatrizoate with catalytically active membranes incorporating microbially produced palladium nanoparticles. Water Res 2010, 44:1498-1506.
27. Howard P.H., Muir D.C.G. Identifying new persistent and bioaccumulative organics among chemicals in commerce II: pharmaceuticals. Environ Sci Technol 2011, 45:6938-6946.
28. ISO 8245 Water quality-guidelines for the determination of total organic carbon (TOC) and dissolved organic carbon (DOC) 1999, 2nd ed.
29. Jeong J., Jung J., Cooper W.J., Song W. Degradation mechanisms and kinetic studies for the treatment of X-ray contrast media compounds by advanced oxidation/reduction processes. Water Res 2010, 44:4391-4398.
30. Joss A., Keller E., Alder A.C., Göbel A., McArdell C.S., Ternes T., et al. Removal of pharmaceuticals and fragrances in biological wastewater treatment. Water Res 2005, 39:3139-3152.
31. Joss A., Zabczynski S., Göbel A., Hoffmann B., Löffler D., McArdell C.S., et al. Biological degradation of pharmaceuticals in municipal wastewater treatment: proposing a classification scheme. Water Res 2006, 40:1686-1696.
32. Kalsch W. Biodegradation of the iodinated X-ray contrast media diatrizoate and iopromide. Sci Total Environ 1999, 225:143-153.
33. Kanda R., Griffin P., James H.A., Fothergill J. Pharmaceutical and personal care products in sewage treatment works. J Environ Monit 2003, 5:823-830.
34. Khetan S.K., Collins T.J. Human pharmaceuticals in the aquatic environment: a challenge to green chemistry. Chem Rev 2007, 107:2319-2364.
35. Kiliç M., Çinar Z. Hydroxyl radical reactions with 4-chlorophenol as a model for heterogeneous photocatalysis. J Mol Struct (THEOCHEM) 2008, 851:263-270.
36. 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.
37. Kümmerer K. Pharmaceuticals in the environment: sources, fate, effects and risks 2008, Springer-Verlag. 3rd ed.
38. Kümmerer K., Steger-Hartmann T., Baranyai A., Bürhaus I. Examination of the biodegradation of the antineoplastics cyclophosphamide and ifosfamide with the closed bottle test (OECD 301 D). Zentralbl Hyg Umweltmed 1996, 198:215-225.
39. La Farré M., Pérez S., Kantiani L., Barceló D. Fate and toxicity of emerging pollutants, their metabolites and transformation products in the aquatic environment. TrAC Trends Anal Chem 2008, 27:991-1007.
40. Laboratory of Mathematical Chemistry B OASIS Catalogic software V. 5.11.6TB 2012, [http://oasis-lmc.org/].
41. Mahmoud W.M.M., Kümmerer K. Captopril and its dimer captopril disulfide: Photodegradation, aerobic biodegradation and identification of transformation products by HPLC-UV and LC-ion trap-MSn. Chemosphere 2012, 88:1170-1177.
42. Messana J.M., Cieslinski D.A., Nguyen V.D., Humes H.D. Comparison of the toxicity of the radiocontrast agents, iopamidol and diatrizoate, to rabbit renal proximal tubule cells in vitro. J Pharmacol Exp Ther 1988, 244:1139-1144.
43. Meylan W.M., Howard P.H. Atom/fragment contribution method for estimating octanol-water partition coefficients. J Pharm Sci 1995, 84:83-92.
44. Michael I., Rizzo L., McArdell C.S., Manaia C.M., Merlin C., Schwartz T., et al. Urban wastewater treatment plants as hotspots for the release of antibiotics in the environment: a review. Water Res 2013, 47:957-995.
45. Miège C., Choubert J.M., Ribeiro L., Eusèbe M., Coquery M. Fate of pharmaceuticals and personal care products in wastewater treatment plants-conception of a database and first results. Environ Pollut 2009, 157:1721-1726.
46. Nyholm N. The european system of standardized legal tests for assessing the biodegradability of chemicals. Environ Toxicol Chem 1991, 10:1237-1246.
47. OECD OECD guidelines for the testing of chemicals: ready biodegradability 301F: manometric respiratory test 1992, OECD Pub.
48. OECD OECD Guidelines for the testing of chemicals: ready biodegradability 301D: closed bottle test 1992, OECD Pub.
49. OECD Revised introduction of the OECD guidelines for testing of chemicals 2006, OECD Pub.
50. OECD Guidelines for testing of chemicals: test no. 316: phototransformation of chemicals in water direct photolysis 2008, OECD Pub, Paris.
51. Putschew A., Jekel M. Iodinated X-ray contrast media. Organic pollutants in the water cycle: Properties, occurrence, analysis and environmental relevance of polar compounds 2006, 87-98. Wiley-VCH; John Wiley, Weinheim, Chichester. T. Reemtsma, M. Jekel (Eds.).
52. Putschew A., Wischnack S., Jekel M. Occurrence of triiodinated X-ray contrast agents in the aquatic environment. Sci Total Environ 2000, 255:129-134.
53. Roberts G., Myatt G., Johnson W., Cross K., Blower P. LeadScope: software for exploring large sets of screening data. J Chem Inf Model 2000, 40:1302-1314.
54. Saiakhov R., Chakravarti S., Klopman G. Effectiveness of CASE ultra expert system in evaluating adverse effects of drugs. Mol Inf 2013, 32:87-97.
55. 2. Appl Catal Environ 2013, 129:13-29.
56. Santos L.H.M.L.M., Araújo A.N., Fachini A., Pena A., Delerue-Matos C., Montenegro M.C.B.S.M. Ecotoxicological aspects related to the presence of pharmaceuticals in the aquatic environment. J Hazard Mater 2010, 175:45-95.
57. Sedykh A., Saiakhov R., Klopman G. META V-a model of photodegradation for the prediction of photoproducts of chemicals under natural-like conditions. Chemosphere 2001, 45:971-981.
58. Seitz W., Weber W.H., Jiang J., Lloyd B.J., Maier M., Maier D., et al. Monitoring of iodinated X-ray contrast media in surface water. Chemosphere 2006, 64:1318-1324.
59. 2-photocatalyzed transformation of the recalcitrant X-ray contrast agent diatrizoate. Appl Catal Environ 2013, 129:114-122.
60. Svetlichnyi V.A., Chaikovskaya O.N., Bazyl O.K., Kuznetsova R.T., Sokolova I.V., et al. Photolysis of phenol and para-chlorophenol by UV laser excitation. High Energy Chem 2001, 35:258-264.
61. 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.
62. Ternes T.A., Joss A., Siegrist H. Peer Reviewed: scrutinizing pharmaceuticals and personal care products in wastewater treatment. Environ Sci Technol 2004, 38:392A.
63. Trautwein C., Kümmerer K. Incomplete aerobic degradation of the antidiabetic drug Metformin and identification of the bacterial dead-end transformation product Guanylurea. Chemosphere 2011, 85:765-773.
64. Trautwein C., Kümmerer K. Ready biodegradability of trifluoromethylated phenothiazine drugs, structural elucidation of their aquatic transformation products, and identification of environmental risks studied by LC-MSn and QSAR. Environ Sci Pollut Res 2012, 19:3162-3177.
65. Trovó A.G., Nogueira R.F.P., Agüera A., Fernandez-Alba A.R., Sirtori C., Malato S. Degradation of sulfamethoxazole in water by solar photo-Fenton. Chemical and toxicological evaluation. Water Res 2009, 43:3922-3931.
66. U.S. Environmental Protection Agency EHAC. PBT Profiler: A Component of OPPT's P2 Frame work V 2.000.2012; (accessed August 08, 2013). http://www.pbtprofiler.net/.
67. Velo-Gala I., López-Peñalver J.J., Sánchez-Polo M., Rivera-Utrilla J. Ionic X-ray contrast media degradation in aqueous solution induced by gamma radiation. Chem Eng J 2012, 195-6:369-376.
68. Wheeler L.A., Norman A., Riley R. Mutagenicity of diatrizoate and other triiodobenzoic acid derivatives in the Ames Salmonella/microsome test. Proc West Pharmacol Soc 1980, 23:249-253.