Investigation of pharmaceuticals and illicit drugs in waters by liquid chromatography-high-resolution mass spectrometry

TrAC - Trends in Analytical Chemistry

Volumn 63, Issue , 2014, Pages 140-157

  Hernandez F ^a   Ibanez M ^a   Bade, R ^a   Bijlsma, L ^a   Sancho, J V ^a  

^a UNIVERSITAT JAUME I   (Spain)

Author keywords

Emerging contaminant; High resolution mass spectrometry (HRMS); Illicit drug; LC HRMS; Liquid chromatography (LC); Orbitrap; Pharmaceutical; Screening; Time of flight; Transformation product

Indexed keywords

DRUG PRODUCTS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IMPURITIES; LIQUIDS; MASS SPECTROMETRY; ORGANIC POLLUTANTS; SCREENING;

EMERGING CONTAMINANT; HIGHRESOLUTION MASS SPECTROMETRY (HRMS); ILLICIT DRUG; LC-HRMS; ORBITRAP; TIME OF FLIGHT; TRANSFORMATION PRODUCTS;

HIGH PRESSURE LIQUID CHROMATOGRAPHY;

AMOXICILLIN; AMPHETAMINE; ANTIBIOTIC AGENT; ATENOLOL; BENZOYLECGONINE; CARBAMAZEPINE; CLARITHROMYCIN; COCAINE; DICLOFENAC; ENALAPRIL; ENALAPRILAT; GLIBENCLAMIDE; ILLICIT DRUG; LEVAMISOLE; LINCOMYCIN; METHADONE; OMEPRAZOLE; OSELTAMIVIR; SILDENAFIL; SULFADIMIDINE; SULFAMETHOXAZOLE; TRIMETHOPRIM; ZANAMIVIR;

ACCURACY; ANALYTIC METHOD; DRUG SCREENING; LIQUID CHROMATOGRAPHY; MASS SPECTROMETER; MASS SPECTROMETRY; PERSISTENT ORGANIC POLLUTANT; RETROSPECTIVE STUDY; REVIEW; SENSITIVITY ANALYSIS; TANDEM MASS SPECTROMETRY; TIME OF FLIGHT MASS SPECTROMETRY; ULTRA PERFORMANCE LIQUID CHROMATOGRAPHY;

EID: 84911996851     PISSN: 01659936     EISSN: 18793142     Source Type: Journal    
DOI: 10.1016/j.trac.2014.08.003     Document Type: Review

References (123)

1. Richardson S.D. Environmental mass spectrometry: emerging contaminants and current issues. Anal. Chem 2012, 84:747-778.
2. Vázquez-Roig P., Blasco C., Picó Y. Advances in the analysis of legal and illegal drugs in the aquatic environment. Trends Anal. Chem 2013, 50:65-77.
3. Petrie B., McAdam E.J., Scrimshaw M.D., Lester J.N., Cartmell E. Fate of drugs during wastewater treatment. Trends Anal. Chem 2013, 49:145-159.
4. Kosjek T., Heath E., Petrović M., Barceló D. Mass spectrometry for identifying pharmaceutical biotransformation products in the environment. Trends Anal. Chem 2007, 26:1076-1085.
5. Petrovic M., Barceló D. LC-MS for identifying photodegradation products of pharmaceuticals in the environment. Trends Anal. Chem 2007, 26:486-493.
6. Agüera A., Martínez Bueno M.J., Fernández-Alba A.R. New trends in the analytical determination of emerging contaminants and their transformation products in environmental waters. Environ. Sci. Pollut. Res. Int 2013, 20:3496-3515.
7. Castiglioni S., Thomas K.V., Kasprzyk-Hordern B., Vandam L., Griffiths P. Testing wastewater to detect illicit drugs: state of the art, potential and research needs. Sci. Total Environ 2014, 487:613-620.
8. Thomas K.V., Bijlsma L., Castiglioni S., Covaci A., Emke E., Grabic R., et al. Comparing illicit drug use in 19 European cities through sewage analysis. Sci. Total Environ 2012, 432:432-439.
9. Castiglioni S., Bijlsma L., Covaci A., Emke E., Hernández F., Reid M., et al. Evaluation of uncertainties associated with the determination of community drug use through the measurement of sewage drug biomarkers. Environ. Sci. Technol 2013, 47:1452-1460.
10. Petrovic M., Farré M., Lopez de Alda M., Perez S., Postigo C., Köck M., et al. Recent trends in the liquid chromatography-mass spectrometry analysis of organic contaminants in environmental samples. J. Chromatogr. A 2010, 4004-4017.
11. Pozo O.J., Guerrero C., Sancho J.V., Ibáñez M., Pitarch E., Hogendoorn E., et al. Efficient approach for the reliable quantification and confirmation of antibiotics in water using on-line solid-phase extraction liquid chromatography/tandem mass spectrometry. J. Chromatogr. A 2006, 1103:83-93.
12. Baker D.R., Kasprzyk-Hordern B. Multi-residue determination of the sorption of illicit drugs and pharmaceuticals to wastewater suspended particulate matter using pressurised liquid extraction, solid phase extraction and liquid chromatography coupled with tandem mass spectrometry. J. Chromatogr. A 2011, 1218:8036-8059.
13. Farré M., Holčapek M., Schoenmakers P.J., Kantiani L., Petrovic M., Pérez S., et al. Achievements and future trends in the analysis of emerging organic contaminants in environmental samples by mass spectrometry and bioanalytical techniques. J. Chromatogr. A 2012, 1259:86-99.
14. Gracia-Lor E., Sancho J.V., Hernández F. Multi-class determination of around 50 pharmaceuticals, including 26 antibiotics, in environmental and wastewater samples by ultra-high performance liquid chromatography-tandem mass spectrometry. J. Chromatogr. A 2011, 1218:2264-2275.
15. 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, 397:943-951.
16. Díaz R., Ibáñez M., Sancho J.V., Hernández F. Target and non-target screening strategies for organic contaminants, residues and illicit substances in food, environmental and human biological samples by UHPLS-QTOF-MS. Anal. Methods 2012, 196-209.
17. Plumb R., Castro-Pérez J., Granger J., Beattie I., Joncour K., Wright A. Ultra-performance liquid chromatography coupled to quadrupole-orthogonal time-of-flight mass spectrometry. Rapid Commun. Mass Spectrom 2004, 18:2331-2337.
18. Hernández F., Sancho J.V., Ibáñez M., Abad E., Portolés T., Mattioli L. Current use of high-resolution mass spectrometry in the environmental sciences. Anal. Bioanal. Chem 2012, 403:1251-1264.
19. Kaufmann A., Butcher P., Maden K., Walker S., Widmer M. Comprehensive comparison of liquid chromatography selectivity as provided by two types of liquid chromatography detectors (high resolution mass spectrometry and tandem mass spectrometry): "where is the crossover point?". Anal. Chim. Acta 2010, 673:60-72.
20. Bijlsma L., Emke E., Hernández F., de Voogt P., Hernandez F. Performance of the linear ion trap Orbitrap mass analyzer for qualitative and quantitative analysis of drugs of abuse and relevant metabolites in sewage water. Anal. Chim. Acta 2013, 768:102-110.
21. Hernández F., Ibáñez M., Gracia-Lor E., Sancho J.V. Retrospective LC-QTOF-MS analysis searching for pharmaceutical metabolites in urban wastewater. J. Sep. Sci 2011, 34:3517-3526.
22. Boix C., Ibáñez M., Sancho J.V., Niessen W.M.A., Hernández F. Investigating the presence of omeprazole in waters by liquid chromatography coupled to low and high resolution mass spectrometry: degradation experiments. J. Mass Spectrom 2013, 48:1091-1100.
23. Boix C., Ibáñez M., Zamora T., Sancho J.V., Niessen W.M.A., Hernández F. Identification of new omeprazole metabolites in wastewaters and surface waters. Sci. Total Environ 2014, 468-469:706-714.
24. Ibáñez M., Sancho J.V., Bijlsma L., van Nuijs A.L.N., Covaci A., Hernández F. Comprehensive analytical strategies based on high-resolution time-of-flight mass spectrometry to identify new psychoactive substances. Trends Anal. Chem 2014, 57:107-117.
25. Ibáñez M., Sancho J.V., Pozo Ó.J., Niessen W., Hernández F. Use of quadrupole time-of-flight mass spectrometry in the elucidation of unknown compounds present in environmental water. Rapid Commun. Mass Spectrom 2005, 19:169-178.
26. Hug C., Ulrich N., Schulze T., Brack W., Krauss M. Identification of novel micropollutants in wastewater by a combination of suspect and nontarget screening. Environ. Pollut 2014, 184C:25-32.
27. Kern S., Baumgartner R., Helbling D.E., Hollender J., Singer H., Loos M.J., et al. A tiered procedure for assessing the formation of biotransformation products of pharmaceuticals and biocides during activated sludge treatment. J. Environ. Monit 2010, 12:2100-2111.
28. 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, 43:7039-7046.
29. Boix C., Ibáñez M., Bijlsma L., Sancho J.V., Hernández F. Investigation of cannabis biomarkers and transformation products in waters by liquid chromatography coupled to time of flight and triple quadrupole mass spectrometry. Chemosphere 2014, 99:64-71.
30. Bijlsma L., Boix C., Niessen W.M.A., Ibáñez M., Sancho J.V., Hernández F. Investigation of degradation products of cocaine and benzoylecgonine in the aquatic environment. Sci. Total Environ 2013, 443:200-208.
31. Calza P., Medana C., Padovano E., Giancotti V., Baiocchi C. Identification of the unknown transformation products derived from clarithromycin and carbamazepine using liquid chromatography/high-resolution mass spectrometry. Rapid Commun. Mass Spectrom 2012, 26:1687-1704.
32. Calza P., Medana C., Padovano E., Dal Bello F., Baiocchi C. Identification of the unknown transformation products derived from lincomycin using LC-HRMS technique. J. Mass Spectrom 2012, 47:751-759.
33. Bateman K.P., Castro-perez J., Wrona M., Shockcor J.P., Yu K., Oballa R., et al. MS E with mass defect filtering for in vitro and in vivo metabolite identification. Rapid Commun. Mass Spectrom 2007, 21:1485-1496.
34. Zhang Y., Ficarro S.B., Li S., Marto J.A. Optimized Orbitrap HCD for quantitative analysis of phosphopeptides. J. Am. Soc. Mass Spectrom 2009, 20:1425-1434.
35. González-Mariño I., Quintana J.B., Rodriguez I., González-Díez M., Cela R. Screening and selective quantification of illicit drugs in wastewater by mixed-mode solid-phase extraction and quadrupole-time-of-flight liquid chromatography-mass spectrometry. Anal. Chem 2012, 84:1708-1717.
36. Ferrer I., Thurman E.M. Analysis of 100 pharmaceuticals and their degradates in water samples by liquid chromatography/quadrupole time-of-flight mass spectrometry. J. Chromatogr. A 2012, 1259:148-157.
37. Sherma J., John D., Larkin F.H. UPLC: Ultra-performance liquid chromatography. J. AOAC Int 2005, 88:63A-67A.
38. Mezcua M., Agüera A., Lliberia J.L., Cortés M.A., Bagó B., Fernández-Alba A.R. Application of ultra performance liquid chromatography-tandem mass spectrometry to the analysis of priority pesticides in groundwater. J. Chromatogr. A 2006, 1109:222-227.
39. Leandro C.C., Hancock P., Fussell R.J., Keely B.J. Comparison of ultra-performance liquid chromatography and high-performance liquid chromatography for the determination of priority pesticides in baby foods by tandem quadrupole mass spectrometry. J. Chromatogr. A 2006, 1103:94-101.
40. Pozo O.J., Barreda M., Sancho J.V., Hernández F., Ll Lliberia J., Cortés M.A., et al. Multiresidue pesticide analysis of fruits by ultra-performance liquid chromatography tandem mass spectrometry. Anal. Bioanal. Chem 2007, 389:1765-1771.
41. Kasprzyk-Hordern B., Dinsdale R.M., Guwy A.J. Multi-residue method for the determination of basic/neutral pharmaceuticals and illicit drugs in surface water by solid-phase extraction and ultra performance liquid chromatography-positive electrospray ionisation tandem mass spectrometry. J. Chromatogr. A 2007, 1161:132-145.
42. Gros M., Rodríguez-Mozaz S., Barceló D. Fast and comprehensive multi-residue analysis of a broad range of human and veterinary pharmaceuticals and some of their metabolites in surface and treated waters by ultra-high-performance liquid chromatography coupled to quadrupole-linear ion trap tandem. J. Chromatogr. A 2012, 1248:104-121.
43. van Nuijs A.L.N., Castiglioni S., Tarcomnicu I., Postigo C., Lopez de Alda M., Neels H., et al. Illicit drug consumption estimations derived from wastewater analysis: a critical review. Sci. Total Environ 2011, 409:3564-3577.
44. Hardman M., Makarov A.A. Interfacing the orbitrap mass analyzer to an electrospray ion source. Anal. Chem 2003, 75:1699-1705.
45. Hu Q., Noll R.J., Li H., Makarov A., Hardman M., Graham Cooks R. The Orbitrap: a new mass spectrometer. J. Mass Spectrom 2005, 40:430-443.
46. Kellmann M., Muenster H., Zomer P., Mol H. Full scan MS in comprehensive qualitative and quantitative residue analysis in food and feed matrices: how much resolving power is required?. J. Am. Soc. Mass Spectrom 2009, 20:1464-1476.
47. Makarov A., Scigelova M. Coupling liquid chromatography to Orbitrap mass spectrometry. J. Chromatogr. A 2010, 1217:3938-3945.
48. Pinhancos R., Maass S., Ramanathan D.M. High-resolution mass spectrometry method for the detection, characterization and quantitation of pharmaceuticals in water. J. Mass Spectrom 2011, 46:1175-1181.
49. Wille K., Claessens M., Rappé K., Monteyne E., Janssen C.R., De Brabander H.F., et al. Rapid quantification of pharmaceuticals and pesticides in passive samplers using ultra high performance liquid chromatography coupled to high resolution mass spectrometry. J. Chromatogr. A 2011, 1218:9162-9173.
50. Rodayan A., Segura P.A., Yargeau V. Ozonation of wastewater: removal and transformation products of drugs of abuse. Sci. Total Environ 2014, 487:763-770.
51. Zonja B., Gonçalves C., Pérez S., Delgado A., Petrovic M., Alpendurada M.F., et al. Evaluation of the phototransformation of the antiviral zanamivir in surface waters through identification of transformation products. J. Hazard. Mater 2014, 265:296-304.
52. Marchese S., Gentili A., Perret D., Ascenzo D., Pastori F. Quadrupole time-of-flight versus triple-quadrupole mass spectrometry for the determination of non-steroidal antiinflammatory drugs in surface water by liquid chromatography/tandem mass spectrometry. Rapid Commun. Mass Spectrom 2003, 17:879-886.
53. Ferrer I. Liquid chromatography/time-of-flight/mass spectrometry (LC/TOF/MS) for the analysis of emerging contaminants. Trends Anal. Chem 2003, 22:750-756.
54. Ferrer I., Thurman E.M. Liquid chromatography/mass spectrometry, MS/MS and time of flight MS: analysis of emerging contaminants. ACS Symp. Ser 2003, 850:1-13.
55. Farré M., Gros M., Hernández B., Petrovic M., Hancock P., Barceló D. Analysis of biologically active compounds in water by ultra-performance liquid chromatography quadrupole time-of-flight mass spectrometry. Rapid Commun. Mass Spectrom 2008, 22:41-51.
56. Stolker A.A.M., Niesing W., Hogendoorn E.A., Versteegh J.F.M., Fuchs R., Brinkman U.A.T. Liquid chromatography with triple-quadrupole or quadrupole-time of flight mass spectrometry for screening and confirmation of residues of pharmaceuticals in water. Anal. Bioanal. Chem 2004, 378:955-963.
57. Stolker A.A.M., Niesing W., Fuchs R., Vreeken R.J., Niessen W.M.A., Brinkman U.A.T. Liquid chromatography with triple-quadrupole and quadrupole-time-of-flight mass spectrometry for the determination of micro-constituents - a comparison. Anal. Bioanal. Chem 2004, 378:1754-1761.
58. Petrović M., Hernando M.D., Díaz-Cruz M.S., Barceló D. Liquid chromatography-tandem mass spectrometry for the analysis of pharmaceutical residues in environmental samples: a review. J. Chromatogr. A 2005, 1067:1-14.
59. Petrović M., Barcelo D. Application of liquid chromatography / quadrupole time-of-flight mass spectrometry (LC-QqTOF-MS). J. Mass Spectrom 2006, 41:1259-1267.
60. Barceló D., Petrovic M. Challenges and achievements of LC-MS in environmental analysis: 25 years on. Trends Anal. Chem 2007, 26:2-11.
61. Hernández F., Sancho J.V., Ibáñez M., Guerrero C. Antibiotic residue determination in environmental waters by LC-MS. Trends Anal. Chem 2007, 26:466-485.
62. Wong C.S., MacLeod S.L. JEM spotlight: recent advances in analysis of pharmaceuticals in the aquatic environment. J. Environ. Monit 2009, 11:923-936.
63. Ferrer I., Thurman M.E. Analysis of pharmaceuticals in drinking water, groundwater, surface water, and wastewater. Comprehensive Analytical Chemistry, vol. 62, Analysis, Removal, Effects and Risk of pharmaceuticals in the water cycle: occurrence and transformation in the environment (electronic book) 2013, 91-128. Elsevier. M. Petrovic, S. Perez, D. Barcelo (Eds.).
64. Martínez Bueno M.J., Agüera A., Gómez M.J., Hernando M.D., García-Reyes J.F., Fernandez-Alba A.R. Application of liquid chromatography/quadrupole-linear Ion trap mass spectrometry and time-of-flight mass spectrometry to the determination of pharmaceuticals and related contaminants in wastewater. Anal. Chem 2007, 79:9372-9384.
65. López-Roldán R., de Alda M.L., Gros M., Petrovic M., Martín-Alonso J., Barceló D. Advanced monitoring of pharmaceuticals and estrogens in the Llobregat River basin (Spain) by liquid chromatography-triple quadrupole-tandem mass spectrometry in combination with ultra performance liquid chromatography-time of flight-mass spectrometry. Chemosphere 2010, 80:1337-1344.
66. Leknes H., Sturtzel I.E., Dye C. Environmental release of oseltamivir from a Norwegian sewage treatment plant during the 2009 influenza A (H1N1) pandemic. Sci. Total Environ 2012, 414:632-638.
67. Magnér J., Filipovic M., Alsberg T. Application of a novel solid-phase-extraction sampler and ultra-performance liquid chromatography quadrupole-time-of-flight mass spectrometry for determination of pharmaceutical residues in surface sea water. Chemosphere 2010, 80:1255-1260.
68. Rodríguez-Álvarez T., Rodil R., Celz R., Quintana J.B. Ion-pair reversed-phase liquid chromatography-quadrupole-time-of-flight and triple-quadrupole-mass-spectrometry determination of ethyl sulfate in wastewater for alcohol consumption tracing. J. Chromatogr. A 2014, 35-42.
69. Ibáñez M., Guerrero C., Sancho J.V., Hernández F. Screening of antibiotics in surface and wastewater samples by ultra-high-pressure liquid chromatography coupled to hybrid quadrupole time-of-flight mass spectrometry. J. Chromatogr. A 2009, 1216:2529-2539.
70. Vergeynst L., Van Langenhove H., Joos P., Demeestre K. High-resolution time-of-flight mass spectrometry for suspect screening and target quantification of pharmaceuticals in river water. Commun. Agric. Appl. Biol. Sci 2013, 78:9-14.
71. Petrovic M., Gros M., Barceló D. Multi-residue analysis of pharmaceuticals in wastewater by ultra-performance liquid chromatography-quadrupole-time-of-flight mass spectrometry. J. Chromatogr. A 2006, 1124:68-81.
72. Lavén M., Alsberg T., Yu Y., Adolfsson-Erici M., Sun H. Serial mixed-mode cation- and anion-exchange solid-phase extraction for separation of basic, neutral and acidic pharmaceuticals in wastewater and analysis by high-performance liquid chromatography-quadrupole time-of-flight mass spectrometry. J. Chromatogr. A 2009, 1216:49-62.
73. Hernández F., Bijlsma L., Sancho J.V., Díaz R., Ibáñez M. Rapid wide-scope screening of drugs of abuse, prescription drugs with potential for abuse and their metabolites in influent and effluent urban wastewater by ultrahigh pressure liquid chromatography-quadrupole-time-of-flight-mass spectrometry. Anal. Chim. Acta 2011, 684:96-106.
74. Gómez M.J., Gómez-Ramos M.M., Malato O., Mezcua M., Férnandez-Alba A.R. Rapid automated screening, identification and quantification of organic micro-contaminants and their main transformation products in wastewater and river waters using liquid chromatography-quadrupole-time-of-flight mass spectrometry with an accurate-mass. J. Chromatogr. A 2010, 1217:7038-7054.
75. Masiá A., Ibáñez M., Blasco C., Sancho J.V., Picó Y., Hernández F. Combined use of liquid chromatography triple quadrupole mass spectrometry and liquid chromatography quadrupole time-of-flight mass spectrometry in systematic screening of pesticides and other contaminants in water samples. Anal. Chim. Acta 2013, 761:117-127.
76. Horai H., Arita M., Kanaya S., Nihei Y., Ikeda T., Suwa K., et al. MassBank: a public repository for sharing mass spectral data for life sciences. J. Mass Spectrom 2010, 45:703-714.
77. Bijlsma L., Emke E., Hernández F., de Voogt P. Investigation of drugs of abuse and relevant metabolites in Dutch sewage water by liquid chromatography coupled to high resolution mass spectrometry. Chemosphere 2012, 89:1399-1406.
78. Cahill M.G., Dineen B.A., Stack M.A., James K.J. A critical evaluation of liquid chromatography with hybrid linear ion trap-Orbitrap mass spectrometry for the determination of acidic contaminants in wastewater effluents. J. Chromatogr. A 2012, 1270:88-95.
79. de Jongh C.M., Kooij P.J.F., de Voogt P., ter Laak T.L. Screening and human health risk assessment of pharmaceuticals and their transformation products in Dutch surface waters ad drinking water. Sci. Total Environ 2012, 70-77.
80. Kosma C.I., Lambropoulou D.A., Albanis T.A. Investigation of PPCPs in wastewater treatment plants in Greece: occurrence, removal and environmental risk assessment. Sci. Total Environ 2014, 466-467:421-438.
81. Chiaia-Hernandez A.C., Krauss M., Hollender J. Screening of lake sediments for emerging contaminants by liquid chromatography atmospheric pressure photoionization and electrospray ionization coupled to high resolution mass spectrometry. Environ. Sci. Technol 2013, 47:976-986.
82. ter Laak T.L., Puijker L.M., van Leerdam J.A., Raat K.J., Kolkman A., de Voogt P., et al. Broad target chemical screening approach used as tool for rapid assessment of groundwater quality. Sci. Total Environ 2012, 427-428:308-313.
83. Emke E., Evans S., Kasprzyk-Hordern B., de Voogt P. Enantiomer profiling of high loads of amphetamine and MDMA in communal sewage: a Dutch perspective. Sci. Total Environ 2014, 487:666-672.
84. Helbling D.E., Hollender J., Kohler H.-P.E., Singer H., Fenner K. High-throughput identification of microbial transformation products of organic micropollutants. Environ. Sci. Technol 2010, 44:6621-6627.
85. Hollender J., Zimmermann S.G., Koepke S., Krauss M., McArdell C.S., Ort C., et al. 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, 43:7862-7869.
86. Radjenović J., Petrović M., Barceló D. Advanced mass spectrometric methods applied to the study of fate and removal of pharmaceuticals in wastewater treatment. Trends Anal. Chem 2007, 26:1132-1144.
87. Kosjek T., Žigon D., Kralj B., Heath E. The use of quadrupole-time-of-flight mass spectrometer for the elucidation of diclofenac biotransformation products in wastewater. J. Chromatogr. A 2008, 1215:57-63.
88. Boreen A.L., Arnold W.A., McNeill K. Triplet-sensitized photodegradation of sulfa drugs containing six-membered heterocyclic groups: identification of an SO2 extrusion photoproduct. Environ. Sci. Technol 2005, 39:3630-3638.
89. Eichhorn P., Ferguson P.L., Pérez S., Aga D.S. Application of ion trap-MS with H/D exchange and QqTOF-MS in the identification of microbial degradates of trimethoprim in nitrifying activated sludge. Anal. Chem 2005, 77:4176-4184.
90. Eichhorn P., Pérez S., Aceña J., Gardinali P., Abad J.L., Barceló D. Identification of phototransformation products of sildenafil (Viagra) and its N-demethylated human metabolite under simulated sunlight. J. Mass Spectrom 2012, 47:701-711.
91. Pérez-Parada A., Agüera A., Gómez-Ramos M.D.M., García-Reyes J.F., Heinzen H., Fernández-Alba A.R. Behavior of amoxicillin in wastewater and river water: identification of its main transformation products by liquid chromatography/electrospray quadrupole time-of-flight mass spectrometry. Rapid Commun. Mass Spectrom 2011, 25:731-742.
92. Doll T.E., Frimmel F.H. Fate of pharmaceuticals - photodegradation by simulated solar UV-light. Chemosphere 2003, 52:1757-1769.
93. Latch D.E., Stender B.L., Packer J.L., Arnold W.A., McNeill K. Photochemical fate of pharmaceuticals in the environment: cimetidine and ranitidine. Environ. Sci. Technol 2003, 37:3342-3350.
94. Boreen A.L., Arnold W.A., McNeill K. Photodegradation of pharmaceuticals in the aquatic environment: a review. Aquat. Sci 2003, 65:320-341.
95. DellaGreca M., Fiorentino A., Iesce M.R., Isidori M., Nardelli A., Previtera L., et al. Identification of phototransformation products of prednisone by sunlight: toxicity of the drug and its derivatives on aquatic organisms. Environ. Toxicol. Chem 2003, 22:534-539.
96. Halling-Sørensen B., Sengeløv G., Tjørnelund J. Toxicity of tetracyclines and tetracycline degradation products to environmentally relevant bacteria, including selected tetracycline-resistant bacteria. Arch. Environ. Contam. Toxicol 2002, 42:263-271.
97. Agüera A., Pérez Estrada L.A., Ferrer I., Thurman E.M., Malato S., Fernández-Alba A.R. Application of time-of-flight mass spectrometry to the analysis of phototransformation products of diclofenac in water under natural sunlight. J. Mass Spectrom 2005, 40:908-915.
98. Pérez S., Eichhorn P., Barceló D. Structural characterization of photodegradation products of enalapril and its metabolite enalaprilat obtained under simulated environmental conditions by hybrid quadrupole-linear ion trap-MS and quadrupole-time-of-flight-MS. Anal. Chem 2007, 79:8293-8300.
99. Calza P., Medana C., Padovano E., Giancotti V., Minero C. Fate of selected pharmaceuticals in river waters. Environ. Sci. Pollut. Res. Int 2013, 20:2262-2270.
100. Postigo C., Sirtori C., Oller I., Malato S., Maldonado M.I., López de Alda M., et al. Photolytic and photocatalytic transformation of methadone in aqueous solutions under solar irradiation: kinetics, characterization of major intermediate products and toxicity evaluation. Water Res 2011, 45:4815-4826.
101. Postigo C., Sirtori C., Oller I., Malato S., Maldonado M.I., López de Alda M., et al. Solar transformation and photocatalytic treatment of cocaine in water: kinetics, characterization of major intermediate products and toxicity evaluation. Appl. Catal. B Environ 2011, 104:37-48.
102. Rivera-Utrilla J., Sánchez-Polo M., Ferro-García M.Á., Prados-Joya G., Ocampo-Pérez R. Pharmaceuticals as emerging contaminants and their removal from water. A review. Chemosphere 2013, 93:1268-1287.
103. Klavarioti M., Mantzavinos D., Kassinos D. Removal of residual pharmaceuticals from aqueous systems by advanced oxidation processes. Environ. Int 2009, 35:402-417.
104. Dantas R.F., Canterino M., Marotta R., Sans C., Esplugas S., Andreozzi R. Bezafibrate removal by means of ozonation: primary intermediates, kinetics, and toxicity assessment. Water Res 2007, 41:2525-2532.
105. Gómez-Ramos M.D.M., Mezcua M., Agüera A., Fernández-Alba A.R., Gonzalo S., Rodríguez A., et al. Chemical and toxicological evolution of the antibiotic sulfamethoxazole under ozone treatment in water solution. J. Hazard. Mater 2011, 192:18-25.
106. Radjenović J., Matošić M., Mijatović I., Petrović M., Barceló D. Membrane Bioreactor (MBR) as an advanced wastewater treatment technology. Hdb. Env. Chem 2008, 5:37-101. in: D. Barceló, M. Petrovic (Editors), Water Pollut., Springer Berlin Heidelberg, Berlin, Heidelberg.
107. Radjenović J., Pérez S., Petrović M., Barceló 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, 1210:142-153.
108. García-Galán M.J., Rodríguez-Rodríguez C.E., Vicent T., Caminal G., Díaz-Cruz M.S., Barceló D. Biodegradation of sulfamethazine by Trametes versicolor: removal from sewage sludge and identification of intermediate products by UPLC-QqTOF-MS. Sci. Total Environ 2011, 409:5505-5512.
109. Hernández F., Sancho J.V., Ibáñez M., Portolés T. TOF and QTOF-MS for identifying unknown contaminants and degradation products in the environment. Encycl. Anal. Chem 2011, John Wiley & Sons, Ltd., Chichester. R.A. Meyers (Ed.).
110. Grange A.H., Zumwalt M.C., Sovocool G.W. Determination of ion and neutral loss compositions and deconvolution of product ion mass spectra using an orthogonal acceleration time-of-flight mass spectrometer and an ion correlation program. Rapid Commun. Mass Spectrom 2006, 20:89-102.
111. Terzic S., Ahel M. Nontarget analysis of polar contaminants in freshwater sediments influenced by pharmaceutical industry using ultra-high-pressure liquid chromatography-quadrupole time-of-flight mass spectrometry. Environ. Pollut 2011, 159:557-566.
112. Ferrer I., Thurman E.M. Identification of a new antidepressant and its glucuronide metabolite in water samples using liquid chromatography/quadrupole time-of-flight mass spectrometry. Anal. Chem 2010, 82:8161-8168.
113. Díaz R., Ibáñez M., Sancho J.V., Hernández F. Building an empirical mass spectra library for screening of organic pollutants by ultra-high-pressure liquid chromatography/ hybrid quadrupole time-of-flight mass spectrometry. Rapid Commun. Mass Spectrom 2011, 25:355-369.
114. Ibáñez M., Sancho J.V., McMillan D., Rao R., Hernández F. Rapid non-target screening of organic pollutants in water by ultraperformance liquid chromatography coupled to time-of-light mass spectrometry. Trends Anal. Chem 2008, 27:481-489.
115. Gómez-Ramos M.D.M., Pérez-Parada A., García-Reyes J.F., Fernández-Alba A.R., Agüera A. Use of an accurate-mass database for the systematic identification of transformation products of organic contaminants in wastewater effluents. J. Chromatogr. A 2011, 1218:8002-8012.
116. Martínez Bueno M.J., Ulaszewska M.M., Gómez M.J., Hernando M.D., Fernández-Alba A.R. Simultaneous measurement in mass and mass/mass mode for accurate qualitative and quantitative screening analysis of pharmaceuticals in river water. J. Chromatogr. A 2012, 1256:80-88.
117. Nurmi J., Pellinen J., Rantalainen A.-L. Critical evaluation of screening techniques for emerging environmental contaminants based on accurate mass measurements with time-of-flight mass spectrometry. J. Mass Spectrom 2012, 47:303-312.
118. Hogenboom A.C., van Leerdam J.A., de Voogt P. Accurate mass screening and identification of emerging contaminants in environmental samples by liquid chromatography-hybrid linear ion trap Orbitrap mass spectrometry. J. Chromatogr. A 2009, 510-519.
119. Schymanski E.L., Singer H.P., Longrée P., Loos M., Ruff M., Stravs M.A., et al. Strategies to characterize polar organic contamination in wastewater: exploring the capability of high resolution mass spectrometry. Environ. Sci. Technol 2014, 48:1811-1818.
120. Nurmi J., Pellinen J. Multiresidue method for the analysis of emerging contaminants in wastewater by ultra performance liquid chromatography-time-of-flight mass spectrometry. J. Chromatogr. A 2011, 1218:6712-6719.
121. Díaz R., Ibáñez M., Sancho J.V., Hernández F. Qualitative validation of a liquid chromatography-quadrupole-time of flight mass spectrometry screening method for organic pollutants in waters. J. Chromatogr. A 2013, 1276:47-57.
122. Bagnati R., Davoli E. Analytical methods for the detection of illicit drugs in wastewaters and surface waters. Illicit Drugs in the Environment: Occurence, Analysis and Fate Using Mass Spectrometry 2011, 55-67. John Wiley & Sons, Inc. S. Castiglioni, E. Zuccato, R. Fanelli (Eds.).
123. van der Aa M., Bijlsma L., Emke E., Dijkman E., van Nuijs A.L.N., van de Ven B., et al. Risk assessment for drugs of abuse in the Dutch watercycle. Water Res 2013, 47:1848-1857.