Biotransformation of benzotriazoles: Insights from transformation product identification and compound-specific isotope analysis

Environmental Science and Technology

Volumn 48, Issue 8, 2014, Pages 4435-4443

  Huntscha, Sebastian ^a,b   Hofstetter, Thomas B ^a,b   Schymanski, Emma L ^a   Spahr, Stephanie ^a   Hollender, Juliane ^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 PROCESS; BIODEGRADATION; DEGRADATION; ISOTOPES; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; PHOTODEGRADATION; WASTEWATER TREATMENT;

BIOLOGICAL DEGRADATION; BIOLOGICAL WASTE WATER TREATMENT; CARBON AND NITROGEN ISOTOPES; COMPOUND-SPECIFIC ISOTOPE ANALYSIS; ORGANIC MICRO-POLLUTANTS; TANDEM MASS SPECTROMETRY; TRANSFORMATION PRODUCTS; WASTEWATER EFFLUENTS;

EFFLUENTS;

1H BENZOTRIAZOLE; 4 METHYL 1H BENZOTRIAZOLE; 5 METHYL 1H BENZOTRIAZOLE; BENZOTRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ACTIVATED SLUDGE; AQUATIC ENVIRONMENT; BIODEGRADATION; BIOTRANSFORMATION; CORROSION; HYDROXYL RADICAL; ISOTOPIC ANALYSIS; ORGANIC COMPOUND; OXIDATION; POLLUTANT; WASTEWATER; WATER TREATMENT;

ACTIVATED SLUDGE; ALKYLATION; ARTICLE; BIODEGRADATION; BIOTRANSFORMATION; CONTROLLED STUDY; HYDROXYLATION; ISOTOPE ANALYSIS; LIQUID CHROMATOGRAPHY; OXIDATION; TANDEM MASS SPECTROMETRY; WASTE WATER MANAGEMENT; WASTE WATER TREATMENT PLANT;

BATCH CELL CULTURE TECHNIQUES; BIODEGRADATION, ENVIRONMENTAL; BIOREACTORS; BIOTRANSFORMATION; CARBON ISOTOPES; CHEMICAL FRACTIONATION; ISOTOPE LABELING; NITROGEN ISOTOPES; SEWAGE; TIME FACTORS; TRIAZOLES;

EID: 84898838736     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es405694z     Document Type: Article

References (46)

1. Schwarzenbach, R. P.; Egli, T.; Hofstetter, T. B.; von Gunten, U.; Wehrli, B., Global Water Pollution and Human Health. In Annual Review of Environment and Resources, Vol. 35, Gadgil, A., Liverman, D. M., Eds.; Annual Reviews: Palo Alto, 2010; Vol. 35, pp 109-136.
2. Schwarzenbach, R. P.; Escher, B. I.; Fenner, K.; Hofstetter, T. B.; Johnson, C. A.; von Gunten, U.; Wehrli, B. The challenge of micropollutants in aquatic systems Science 2006, 313 (5790) 1072-1077
3. Helbling, D. E.; Hollender, J.; Kohler, H. P.; Singer, H.; Fenner, K. High-throughput identification of microbial transformation products of organic micropollutants Environ. Sci. Technol. 2010, 44 (17) 6621-6627
4. Kern, S.; Baumgartner, R.; Helbling, D. E.; Hollender, J.; Singer, H.; Loos, M. J.; Schwarzenbach, R. P.; Fenner, K. A tiered procedure for assessing the formation of biotransformation products of pharmaceuticals and biocides during activated sludge treatment J. Environ. Monit.: JEM 2010, 12 (11) 2100-2111
5. Nödler, K.; Hillebrand, O.; Idzik, K.; Strathmann, M.; Schiperski, F.; Zirlewagen, J.; Licha, T. Occurrence and fate of the angiotensin II receptor antagonist transformation product valsartan acid in the water cycle: A comparative study with selected β-blockers and the persistent anthropogenic wastewater indicators carbamazepine and acesulfame Water Res. 2013, 47, 6650-6659
6. Kormos, J. L.; Schulz, M.; Kohler, H. P.; Ternes, T. A. Biotransformation of selected iodinated X-ray contrast media and characterization of microbial transformation pathways Environ. Sci. Technol. 2010, 44 (13) 4998-5007
7. Prasse, C.; Wagner, M.; Schulz, R.; Ternes, T. A. Biotransformation of the antiviral drugs acyclovir and penciclovir in activated sludge treatment Environ. Sci. Technol. 2011, 45 (7) 2761-2769
8. Wick, A.; Wagner, M.; Ternes, T. A. Elucidation of the transformation pathway of the opium alkaloid codeine in biological wastewater treatment Environ. Sci. Technol. 2011, 45 (8) 3374-3385
9. Hofstetter, T. B.; Berg, M. Assessing transformation processes of organic contaminants by compound-specific stable isotope analysis TrAC-Trends Anal. Chem. 2011, 30 (4) 618-627
10. Krauss, M.; Singer, H.; Hollender, J. LC-high resolution MS in environmental analysis: From target screening to the identification of unknowns Anal Bioanal Chem 2010, 397 (3) 943-951
11. Giger, W.; Schaffner, C.; Kohler, H.-P. E. Benzotriazole and tolyltriazole as aquatic contaminants. 1. Input and occurrence in rivers and lakes Environ. Sci. Technol. 2006, 40 (23) 7186-7192
12. 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
13. Loos, R.; Gawlik, B. M.; Locoro, G.; Rimaviciute, E.; Contini, S.; Bidoglio, G. EU-wide survey of polar organic persistent pollutants in European river waters Environ. Pollut. 2009, 157 (2) 561-568
14. Weiss, S.; Jakobs, J.; Reemtsma, T. Discharge of three benzotriazole corrosion inhibitors with municipal wastewater and improvements by membrane bioreactor treatment and ozonation Environ. Sci. Technol. 2006, 40 (23) 7193-7199
15. Voutsa, D.; Hartmann, P.; Schaffner, C.; Giger, W. Benzotriazoles, alkylphenols and bisphenol A in municipal wastewaters and in the Glatt River, Switzerland Environ. Sci. Pollut. Res. Int. 2006, 13 (5) 333-341
16. Hart, D. S.; Davis, L. C.; Erickson, L. E.; Callender, T. M. Sorption and partitioning parameters of benzotriazole compounds Microchem. J. 2004, 77 (1) 9-17
17. Cornell, J. S.; Pillard, D. A.; Hernandez, M. T. Comparative measures of the toxicity of component chemicals in aircraft deicing fluid Environ. Toxicol. Chem. 2000, 19 (6) 1465-1472
18. Kiss, A.; Fries, E. Occurrence of benzotriazoles in the rivers Main, Hengstbach, and Hegbach (Germany) Environ. Sci. Pollut. Res. Int. 2009, 16 (6) 702-710
19. Katritzky, A. R.; Lan, X.; Yang, J. Z.; Denisko, O. V. Properties and synthetic utility of N-substituted benzotriazoles Chem. Rev. 1998, 98 (2) 409-548
20. Reemtsma, T.; Miehe, U.; Duennbier, U.; Jekel, M. Polar pollutants in municipal wastewater and the water cycle: occurrence and removal of benzotriazoles Water Res. 2010, 44 (2) 596-604
21. Janna, H.; Scrimshaw, M. D.; Williams, R. J.; Churchley, J.; Sumpter, J. P. From dishwasher to tap? Xenobiotic substances benzotriazole and tolyltriazole in the environment Environ. Sci. Technol. 2011, 45 (9) 3858-3864
22. Weiss, S.; Reemtsma, T. Determination of benzotriazole corrosion inhibitors from aqueous environmental samples by liquid chromatography- electrospray ionization-tandem mass spectrometry Anal. Chem. 2005, 77 (22) 7415-7420
23. 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
24. Elsner, M.; Jochmann, M. A.; Hofstetter, T. B.; Hunkeler, D.; Bernstein, A.; Schmidt, T. C.; Schimmelmann, A. Current challenges in compound-specific stable isotope analysis of environmental organic contaminants Anal. Bioanal. Chem. 2012, 403 (9) 2471-91
25. Hofstetter, T. B.; Schwarzenbach, R. P.; Bernasconi, S. M. Assessing transformation processes of organic compounds using stable isotope fractionation Environ. Sci. Technol. 2008, 42 (21) 7737-7743
26. Schmidt, T. C.; Zwank, L.; Elsner, M.; Berg, M.; Meckenstock, R. U.; Haderlein, S. B. Compound-specific stable isotope analysis of organic contaminants in natural environments: A critical review of the state of the art, prospects, and future challenges Anal. Bioanal. Chem. 2004, 378 (2) 283-300
27. Elsner, M. Stable isotope fractionation to investigate natural transformation mechanisms of organic contaminants: principles, prospects and limitations J. Environ. Monit.: JEM 2010, 12 (11) 2005-2031
28. Hofstetter, T. B.; Berg, M. Assessing transformation processes of organic contaminants by compound-specific stable isotope analysis TrAC Trends Anal. Chem. 2011, 30 (4) 618-627
29. Spahr, S.; Huntscha, S.; Bolotin, J.; Maier, M. P.; Elsner, M.; Hollender, J.; Hofstetter, T. B. Compound-specific isotope analysis of benzotriazole and its derivatives Anal. Bioanal. Chem. 2013, 405 (9) 2843-2856
30. Clesceri, L. S.; Greenberg, A. E.; Eaton, A. D. EDS. Standard Methods for the Examination of Water and Wastewater, 20 th ed.; American Public Health Association/American Water Works Association/Water Environment Federation: Washington, DC, 1998.
31. Huntscha, S.; Singer, H. P.; McArdell, C. S.; Frank, C. E.; Hollender, J. Multiresidue analysis of 88 polar organic micropollutants in ground, surface and wastewater using online mixed-bed multilayer solid-phase extraction coupled to high performance liquid chromatography-tandem mass spectrometry J. Chromatogr. A 2012, 1268, 74-83
32. Gao, J.; Ellis, L. B.; Wackett, L. P. The University of Minnesota Biocatalysis/Biodegradation Database: improving public access Nucleic Acids Res. 2010, 38 (Database issue) D488-491
33. Meringer, M.; Reinker, S.; Zhang, J.; Muller, A. MS/MS data improves automated determination of molecular formulas by mass spectrometry Match 2011, 65 (2) 259-290
34. Benecke, C.; Grüner, T.; Kerber, A.; Laue, R.; Wieland, T. Molecular structure generation with MOLGEN, new features and future developments Fresenius' J. Anal. Chem. 1997, 359 (1) 23-32
35. Wolf, S.; Schmidt, S.; Muller-Hannemann, M.; Neumann, S. In silico fragmentation for computer assisted identification of metabolite mass spectra BMC Bioinformatics 2010, 11, 148
36. Royal Society of Chemistry: http:/www.chemspider.com/ (Accessed 10 Dec 2012).
37. Alvarez-Cohen, L.; Speitel, G. E., Jr. Kinetics of aerobic cometabolism of chlorinated solvents Biodegradation 2001, 12 (2) 105-126
38. Liu, Y. S.; Ying, G. G.; Shareef, A.; Kookana, R. S. Biodegradation of three selected benzotriazoles under aerobic and anaerobic conditions Water Res. 2011, 45 (16) 5005-5014
39. NIST Mass Spectral Library. National Institute of Standards and Technology (NIST): Gaithersburg (MD), USA, 2011.
40. Schymanski, E. L.; Singer, H. P.; Longrée, P.; Loos, M.; Ruff, M.; Stravs, M. A.; Ripollés Vidal, C.; Hollender, J. Strategies to characterize polar organic contamination in wastewater: Exploring the capability of high resolution mass spectrometry Environ. Sci. Technol. 2014, 48 (3) 1811-1818
41. Finšgar, M.; Milošev, I. Corrosion study of copper in the presence of benzotriazole and its hydroxy derivative Mater. Corros. 2011, 62 (10) 956-966
42. König, W.; Geiger, R. A new method for synthesis of peptides: Activation of the carboxyl group with dicyclohexylcarbodiimide using 1-hydroxybenzotriazoles as additives Chem. Ber. 1970, 103 (3) 788-798
43. Wehrstedt, K. D.; Wandrey, P. A.; Heitkamp, D. Explosive properties of 1-hydroxybenzotriazoles J Hazard Mater. 2005, 126 (1-3) 1-7
44. Fritsche, A.; Deguara, H.; Lehr, M. Convenient synthesis of tert -butyl esters of indole-5-carboxylic acid and related heterocyclic carboxylic acids Synth. Commun. 2006, 36 (21) 3117-3123
45. Wijker, R. S.; Kurt, Z.; Spain, J. C.; Bolotin, J.; Zeyer, J.; Hofstetter, T. B. Isotope fractionation associated with the biodegradation of 2- and 4-nitrophenols via monooxygenation pathways Environ. Sci. Technol. 2013, 47, 14185-14193
46. Centler, F.; Hesse, F.; Thullner, M. Estimating pathway-specific contributions to biodegradation in aquifers based on dual isotope analysis: Theoretical analysis and reactive transport simulations J. Contam. Hydrol. 2013, 152, 97-116