High-throughput identification of microbial transformation products of organic micropollutants

Environmental Science and Technology

Volumn 44, Issue 17, 2010, Pages 6621-6627

  Helbling, Damian E ^a   Hollender, Juliane ^a   Kohler, Hans Peter E ^a   Singer, Heinz ^a   Fenner, Kathrin ^a,b  

^a SWISS FEDERAL INSTITUTE OF AQUATIC SCIENCE AND TECHNOLOGY   (Switzerland)

^b ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATED SLUDGE; BEZAFIBRATE; DATA PROCESSING METHODS; EXPOSURE POTENTIAL; HIGH-THROUGHPUT; LEVETIRACETAM; LINEAR ION TRAP; MEDIATED REACTIONS; MICROBIAL TRANSFORMATION; ORBITRAP; ORGANIC MICROPOLLUTANTS; OSELTAMIVIR; PREDICTION TOOLS; REACTION PATHWAYS; STRUCTURE-BASED; TARGET SCREENING; TRANSFORMATION PRODUCTS; TRANSFORMATION REACTIONS; VALSARTAN;

BATCH REACTORS; BIOCHEMISTRY; MASS SPECTROMETRY; PESTICIDES; WASTEWATER; WASTEWATER TREATMENT;

DATA PROCESSING;

ATENOLOL; BEZAFIBRATE; DIAZEPAM; ETIRACETAM; NAPROPAMIDE; OSELTAMIVIR; PESTICIDE; PROPACHLOR; SURFACE WATER; VALSARTAN; XENOBIOTIC AGENT;

ACTIVATED SLUDGE; BIOTRANSFORMATION; DATA ACQUISITION; DRUG; MASS SPECTROMETRY; MICROBIAL ACTIVITY; ORGANIC POLLUTANT; TRANSFORMATION; WASTEWATER;

ACTIVATED SLUDGE; ARTICLE; BATCH REACTOR; BIOTRANSFORMATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INFORMATION PROCESSING; ION TRAP MASS SPECTROMETRY; POLLUTANT; WASTE WATER TREATMENT PLANT;

AMINES; BACTERIA; BEZAFIBRATE; BIOTRANSFORMATION; ENVIRONMENTAL POLLUTANTS; HIGH-THROUGHPUT SCREENING ASSAYS; ORGANIC CHEMICALS; PESTICIDES; PHARMACEUTICAL PREPARATIONS;

EID: 77956157233     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es100970m     Document Type: Article

References (35)

1. Kolpin, D. W.; Furlong, E. T.; Meyer, M. T.; Thurman, E. M.; Zaugg, S. D.; Barber, L. B.; Buxton, H. T. Pharmaceuticals, hormones, and other organic wastewater contaminants in US streams, 1999-2000: A national reconnaissance Environ. Sci. Technol. 2002, 36 (6) 1202-1211
2. Kümmerer, K. Drugs in the environment: Emission of drugs, diagnostic aids and disinfectants into wastewater by hospitals in relation to other sources-A review Chemosphere 2001, 45 (6-7) 957-969
3. Onesios, K. M.; Yu, J. T.; Bouwer, E. J. Biodegradation and removal of pharmaceuticals and personal care products in treatment systems: a review Biodegradation 2009, 20 (4) 441-466
4. Giger, W.; Gabriel, F. L. P.; Jonkers, N.; Wettstein, F. E.; Kohler, H. P. E. Environmental fate of phenolic endocrine disruptors: Field and laboratory studies Philos. Trans. R. Soc., A 2009, 367 (1904) 3941-3963
5. Kosjek, T.; Heath, E.; Perez, S.; Petrovic, M.; Barcelo, D. Metabolism studies of diclofenac and clofibric acid in activated sludge bioreactors using liquid chromatography with quadrupole-time-of-flight mass spectrometry J. Hydrol. 2009, 372 (1-4) 109-117
6. Nalecz-Jawecki, G.; Wojcik, T.; Sawicki, J. Evaluation of in vitro biotransformation of propranolol with HPLC, MS/MS, and two bioassays Environ. Toxicol. 2008, 23 (1) 52-58
7. Perez, S.; Barcelo, D. Application of advanced MS techniques to analysis and identification of human and microbial metabolites of pharmaceuticals in the aquatic environment Trac.-Trend. Anal. Chem. 2007, 26 (6) 494-514
8. Eichhorn, P.; Ferguson, P. L.; Perez, S.; Aga, D. S. Application of ion trap-MS with QqTOF-MS in the identification H/D exchange and of microbial degradates of trimethoprim in nitrifying activated sludge Anal. Chem. 2005, 77 (13) 4176-4184
9. Haiss, A.; Kummerer, 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 (2) 294-302
10. Langin, A.; Alexy, R.; Konig, A.; Kummerer, K. Deactivation and transformation products in biodegradability testing of beta-lactams amoxicillin and piperacillin Chemosphere 2009, 75 (3) 347-354
11. Quintana, J. B.; Weiss, S.; Reemtsma, T. Pathways and metabolites of microbial degradation of selected acidic pharmaceutical and their occurrence in municipal wastewater treated by a membrane bioreactor Water Res. 2005, 39 (12) 2654-2664
12. Radjenovic, J.; Perez, S.; Petrovic, M.; Barcelo, D. Identification and structural characterization of biodegradation products of atenolol and glibenclamide by liquid chromatography coupled to hybrid quadrupole time-of-flight and quadrupole ion trap mass spectrometry J. Chromatogr., A 2008, 1210 (2) 142-153
13. Schulz, M.; Löffler, D.; Wagner, M.; Ternes, T. A. Transformation of the X-ray contrast medium lopromide in soil and biological wastewater treatment Environ. Sci. Technol. 2008, 42 (19) 7207-7217
14. Zwiener, C.; Seeger, S.; Glauner, T.; Frimmel, F. H. Metabolites from the biodegradation of pharmaceutical residues of ibuprofen in biofilm reactors and batch experiments Anal. Bioanal. Chem. 2002, 372 (4) 569-575
15. Krauss, M.; Hollender, J.; Singer, H. P. LC-high resolution MS in environmental analysis: from target screening to the identification of unknowns. Anal. Bioanal. Chem. 2010, 397 (3), 943 - 951.
16. Peterman, S. M.; Duczak Jr, N.; Kalgutkar, A. S.; Lame, M. E.; Soglia, J. R. Application of a linear ion trap/Orbitrap mass spectrometer in metabolite characterization studies: Examination of the human liver microsomal metabolism of the non-tricyclic anti-depressant nefazodone using data-dependent accurate mass measurements J. Am. Soc. Mass Spectrom. 2006, 17 (3) 363-375
17. Ruan, Q.; Peterman, S.; Szewc, M. A.; Ma, L.; Cui, D.; Humphreys, W. G.; Zhu, M. S. An integrated method for metabolite detection and identification using a linear ion trap/Orbitrap mass spectrometer and multiple data processing techniques: application to indinavir metabolite detection J. Mass Spectrom. 2008, 43 (2) 251-261
18. Gao, J.; Ellis, L. B. M.; Wackett, L. P. The University of Minnesota Biocatalysis/Biodegradation Database: improving public access Nucleic Acids Res. 2010, 38, D488-D491
19. Kern, S.; Fenner, K.; Singer, H. P.; Schwarzenbach, R. P.; Hollender, J. Identification of transformation products of organic contaminants in natural waters by computer-aided prediction and high-resolution mass spectrometry Environ. Sci. Technol. 2009, 43 (18) 7039-7046
20. Helbling, D. E.; Hollender, J.; Kohler, H. P. E.; Fenner, K. A structure-based interpretation of biotransformation pathways of amide-containing compounds in sludge-seeded bioreactors. Environ. Sci. Technol. 2010 (doi: 10.1021/es101035b).
21. Joss, A.; Boehler, M.; Wedi, D.; Siegrist, H. Proposing a method for online permeability monitoring in membrane bioreactors Water Sci. Technol. 2009, 60 (2) 497-506
22. Clesceri, L. S.; Greenberg, A. E.; Eaton, A. D., Eds. Standard Methods for the Examination of Water and Wastewater, 20th ed.; American Public Health Association/American Water Works Association/Water Environment Federation: Washington, DC, 1998.
23. Hollender, J.; Zimmermann, S. G.; Koepke, S.; Krauss, M.; McArdell, C. S.; Ort, C.; Singer, H.; Von Gunten, U.; Siegrist, H. Elimination of organic micropollutants in a municipal wastewater treatment plant upgraded with a full-scale post-ozonation followed by sand filtration Environ. Sci. Technol. 2009, 43 (20) 7862-7869
24. Fick, J.; Lindberg, R. H.; Tysklind, M.; Haemig, P. D.; Waldenstrom, J.; Wallensten, A.; Olsen, B. Antiviral oseltamivir is not removed or degraded in normal sewage water treatment: Implications for development of resistance by influenza A virus. PLoS ONE 2007, 2 (10 10.1371/journal.pone.0000986
25. Kasprzyk-Hordern, B.; Dinsdale, R. M.; Guwy, A. J. The occurrence of pharmaceuticals, personal care products, endocrine disruptors and illicit drugs in surface water in South Wales, UK Water Res. 2008, 42 (13) 3498-3518
26. Maurer, M.; Escher, B. I.; Richle, P.; Schaffner, C.; Alder, A. C. Elimination of beta-blockers in sewage treatment plants Water Res. 2007, 41 (7) 1614-1622
27. Löffler, D.; Römbke, J.; Meller, M.; Ternes, T. A. Environmental fate of pharmaceuticals in water/sediment systems Environ. Sci. Technol. 2005, 39 (14) 5209-5218
28. Field, J. A.; Sierra-Alvarez, R. Microbial transformation of chlorinated benzoates Rev. Environ. Sci. Bio/Technol. 2008, 7 (3) 191-210
29. Habicht, S. C.; Vinueza, N. R.; Archibold, E. F.; Duan, P.; Kenttämaa, H. I. Identification of the carboxylic acid functionality by using electrospray ionization and ion-molecule reactions in a modified linear quadrupole ion trap mass spectrometer Anal. Chem. 2008, 80 (9) 3416-3421
30. González Alonso, S.; Catalá, M.; Maroto, R. R.; Gil, J. L. R.; de Miguel, Á. G.; Valcárcel, Y. Pollution by psychoactive pharmaceuticals in the Rivers of Madrid metropolitan area (Spain) Environ. Int. 2009, 36 (2) 195-201
31. Stamper, D. M.; Tuovinen, O. H. Biodegradation of the acetanilide herbicides alachlor, metolachlor, and propachlor Crit. Rev. Microbiol. 1998, 24 (1) 1-22
32. Rivera-Cancel, G.; Bocioaga, D.; Hay, A. G. Bacterial degradation of N, N-diethyl-m-toluarnide (DEET): Cloning and heterologous expression of DEET hydrolase Appl. Environ. Microbiol. 2007, 73 (9) 3105-3108
33. Draft Assessment Report; European Commission EU Review Programme, 2005, (http://dar.efsa.europa.eu/dar-web/provision).
34. Hole, S. J.; McClure, N. C.; Powles, S. B. Rapid degradation of carbetamide upon repeated application to Australian soils Soil Biol. Biochem. 2001, 33 (6) 739-745
35. Liu, S. Y.; Shocken, M.; Rosazza, J. P. N. Microbial Transformations of Clomazone J. Agric. Food Chem. 1996, 44 (1) 313-319