Identification of metabolites and thermal transformation products of quinolones in raw Cow's milk by liquid chromatography coupled to high-resolution mass spectrometry

Journal of Agricultural and Food Chemistry

Volumn 62, Issue 8, 2014, Pages 2008-2021

  Junza, Alexandra ^a   Barbosa, Sergio ^a   Codony, M Rosa ^b   Jubert, Anna ^b   Barbosa, Jose ^a   Barrón, Dolores ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

^b Laboratori Interprofessional Lleter de Catalunya (ALLIC)   (Spain)

Author keywords

antibiotics; elucidation; LTQ Orbitrap; metabolites; milk; quinolones; thermal treatments; ToF; transformation products

Indexed keywords

ANTIINFECTIVE AGENT; DRUG RESIDUE; QUINOLONE DERIVATIVE;

ANIMAL; ARTICLE; BIOTRANSFORMATION; CATTLE; CHEMICAL STRUCTURE; CHEMISTRY; HEAT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; METABOLISM; MILK; TANDEM MASS SPECTROMETRY;

ANIMALS; ANTI-BACTERIAL AGENTS; BIOTRANSFORMATION; CATTLE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DRUG RESIDUES; HOT TEMPERATURE; MILK; MOLECULAR STRUCTURE; QUINOLONES; TANDEM MASS SPECTROMETRY;

ANTIBIOTICS; BIOMOLECULES; CHROMATOGRAPHY; DAIRY PRODUCTS; HEAT TREATMENT; ISOMERS; KETONES; LIQUIDS; MASS SPECTROMETRY; METABOLITES; MICROORGANISMS; ORGANIC POLYMERS; SPECTROMETRY;

ELUCIDATION; LTQ ORBITRAP; MILK; QUINOLONES; TOF; TRANSFORMATION PRODUCTS;

LIQUID CHROMATOGRAPHY;

EID: 84894797845     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf405554z     Document Type: Article

References (51)

1. Hammerum, A. M.; Heuer, O. E.; Lester, C. H.; Agers, Y.; Seyfarth, A. M.; Emborg, H. D.; Frimodt-Moller, N.; Monnet, D. L. Comment on: Withdrawal of growth-promoting antibiotics in Europe and its effects in relation to human health Int. J. Antimicrob. Agents 2007, 30, 466-468
2. Fábrega, A.; Sánchez-Céspedes, J.; Soto, S.; Vila, J. Quinolone resistance in the food chain Int. J. Antimicrob. Agents 2008, 31, 307-315
3. Commission of the European Communities. Off. J. Eur. Communities 2009, L15/1, No. 37/2010, Dec 22.
4. Zorraquino, M. A.; Althaus, R. L.; Roca, M.; Molina, M. P. Effect of heat treatments on aminoglycosides in milk J. Food Prot. 2009, 72, 1338-1341
5. Early, R. The Technology of Dairy Products, 2 nd ed.; Aspen Publishers; Gaithersburg, MD, USA, 1998.
6. Picó, Y.; Barceló, D. The expanding role of LC/MS in analyzing metabolites and degradation products of food contaminants Trends Anal. Chem. 2008, 27, 821-835
7. Becker, M.; Zittlan, E.; Petz, M. Residue analysis of 15 penicillins and cephalosporins in bovine muscle, kidney and milk by liquid chromatography-tandem mass spectrometry Anal. Chim. Acta 2004, 520, 19-32
8. Junza, A.; Amatya, R.; Barrón, D.; Barbosa, J. Comparative study of the LC-MS/MS and UPLC-MS/MS for the multi-residue analysis of quinolones, penicillins and cephalosporins in cow milk, and validation according to the regulation 2002/657/EC J. Chromatogr., B 2011, 879, 2601-2610
9. Reyns, T.; Cherlet, M.; De Baere, S.; De Backer, P.; Croubels, S. Rapid method for the quantification of amoxicillin and its major metabolites in pig tissues by liquid chromatography-tandem mass spectrometry with emphasis on stability issues J. Chromatogr., B 2008, 861, 108-116
10. Granelli, K.; Elgerud, C.; Lundström, A.; Ohlsson, A.; Sjöberg, P. Rapid multi-residue analysis of antibiotics in muscle by liquid chromatography-tandem mass spectrometry Anal. Chim. Acta 2009, 637, 87-91
11. Martínez-Huélamo, M.; Jiménez-Gámez, E.; Hermo, M. P.; Barrón, D.; Barbosa, J. Determination of penicillins in milk using LC-UV, LC-MS and LC-MS/MS J. Chromatogr., A 2009, 32, 2385-2393
12. Nemutlu, E.; Kir, S.; Katlan, D.; Beksaç, M. S. Simultaneous multiresponse optimization of an HPLC method to separate seven cephalosporins in plasma and amniotic fluid: application to validation and quantification of cefepime, cefixime and cefoperazone Talanta 2009, 80, 117-126
13. Mol, H. G. J.; Plaza-Bolaños, P.; Zomer, P.; de Rijk, T. C.; Stolker, A. A. M.; Mulder, P. P. J. Toward a generic extraction method for simultaneous determination of pesticides, mycotoxins, plant toxins, and veterinary drugs in feed and food matrixes Anal. Chem. 2008, 80, 9450-9459
14. Marazuela, M. D.; Bogialli, S. A review of novel strategies of sample preparation for the determination of antibacterial residues in foodstuffs using liquid chromatography-based analytical methods Anal. Chim. Acta 2009, 645, 5-17
15. Moreno-Bondi, M. C.; Marazuela, M. D.; Herranz, S.; Rodríguez, E. An overview of sample preparation procedures for LC-MS multiclass antibiotic determination in environmental and food samples Anal. Bioanal. Chem. 2009, 395, 921-946
16. Blasco, C.; Torres, C. M.; Picó, Y. Progress in analysis of residual antibacterials in food Trends Anal. Chem. 2007, 26, 895-913
17. Andreu, V.; Blasco, C.; Picó, Y. Analytical strategies to determine quinolone residues in food and the environment Trends Anal. Chem. 2007, 26, 534-556
18. Bogialli, S.; Di Corcia, A. Recent applications of liquid chromatography-mass spectrometry to residue analysis of antimicrobials in food of animal origin Anal. Bioanal. Chem. 2009, 395, 947-966
19. Tang, Q.; Yang, T.; Tan, X.; Luo, J. Simultaneous determination of fluoroquinolone antibiotic residues in milk sample by solid-phase extraction-liquid chromatography-tandem mass spectrometry J. Agric. Food Chem. 2009, 57, 4535-4539
20. Romero-González, R.; Aguilera-Luiz, M. M.; Plaza-Bolaños, P.; Garrido Frenich, A.; Martínez Vidal, J. L. Food contaminant analysis at high resolution mass spectrometry: application for the determination of veterinary drugs in milk J. Chromatogr., A 2011, 1218, 9353-9365
21. Kaufmann, A. Strategy for the elucidation of elemental compositions of trace analytes based on a mass resolution of 100 000 full width at half maximum Rapid Commun. Mass Spectrom. 2010, 24, 2035-2045
22. Zhu, M.; Ma, L.; Zhang, D.; Ray, K.; Zhao, W.; Humphreys, W. G.; Skiles, G.; Sanders, M.; Zhang, H. Detection and characterization of metabolites in biological matrices using mass defect filtering of liquid chromatography/high resolution mass spectrometry data Drug Metab. Dispos. 2006, 34, 1722-1733
23. Nägele, E.; Moritz, R. Structure elucidation of degradation products of the antibiotic amoxicillin with ion trap MS n and accurate mass determination by ESI TOF J. Am. Soc. Mass Spectrom. 2005, 16, 1670-1676
24. Calza, P.; Medana, C.; Carbone, F.; Giancotti, V.; Baiocchi, C. Characterization of intermediate compounds formed upon photoinduced degradation of quinolones by high-performance liquid chromatography/high-resolution multiple-stage mass spectrometry Rapid Commun. Mass Spectrom. 2008, 22, 1533-1552
25. Gómez, M. J.; Gómez-Ramos, M. M.; Malato, O.; Mezcua, M.; Fernández-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 database J. Chromatogr., A 2010, 1217, 7038-7054
26. Kaufmann, A. Determination of the elemental composition of trace analytes in complex matrices using exact masses of product ions and corresponding neutral losses Rapid Commun. Mass Spectrom. 2007, 21, 2003-2013
27. Berendsen, B. J. A.; Essers, M. L.; Mulder, P. P. J.; van Bruchem Lommen, A.; van Overbeek, W. M.; Stolker, L. A. M. Newly identified degradation products of ceftiofur and cephapirin impact the analytical approach for quantitative analysis of kidney J. Chromatogr., A 2009, 1216, 8177-8186
28. Krauss, M.; Singer, H.; Hollonder, J. LC-high resolution MS in environmental analysis: from target screening to the identification of unknowns Anal. Bioanal. Chem. 2010, 397, 943-951
29. Prasad, B.; Garg, A.; Takwani, H.; Singh, S. Metabolite identification by liquid chromatography-mass spectrometry Trends Anal. Chem. 2011, 30, 360-387
30. Lacorte, S.; Fernández-Alba, A. R. Time of flight mass spectrometry applied to the liquid chromatography analysis of pesticides in water and food Mass Spectrom. Rev. 2006, 25, 866-880
31. Malik, A. K.; Blasco, C.; Picó, Y. Liquid chromatography-mass spectrometry in food safety J. Chromatogr., A 2010, 1217, 4018-4040
32. Koulman, A.; Lane, G. A.; Harrison, S. J.; Volmer, D. A. From differentiating metabolites to biomarkers Anal. Bioanal. Chem. 2009, 394, 663-670
33. Jacobs, D. M.; Spiesser, L.; Garnier, M.; de Roo, N.; van Dorsten Hollebrands, B.; van Velzen, E.; Draijer, R.; van Duynhoven, J. SPE-NMR metabolite sub-profiling of urine Anal. Bioanal. Chem. 2012, 404, 2349-2361
34. Sturini, M.; Speltini, A.; Maraschi, F.; Profumo, A.; Pretali, L.; Fasani, E.; Albini, A. Photochemical degradation of marbofloxacin and enrofloxacin in natural waters Environ. Sci. Technol. 2010, l44, 4564-4569
35. Anadón, A.; Martínez-Larrañaga, M. R.; Iturbe, J.; Martínez, M. A.; Díaz, M. J.; Frejo, M. T.; Martínez, M. Pharmacokinetics and residues of ciprofloxacin and its metabolites in broiler chickens Res. Vet. Sci. 2001, 71, 101-109
36. Turnipseed, S. B.; Storey, J. M.; Clark, S. B.; Miller, K. E. Analysis of veterinary drugs and metabolites in milk using quadrupole time-of-flight liquid chromatography-mass spectrometry J. Agric. Food Chem. 2011, 59, 7569-7581
37. 14C-labeled and non-labeled difloxacin in pigs after oral administration, and antimicrobial activity of manure containing difloxacin and its metabolites Environ. Res. 2009, 109, 225-231
38. Turiel, E.; Bordin, G.; Rodríguez, A. R. Study of the evolution and degradation products of ciprofloxacin and oxolinic acid in river water samples by HPLC-UV/MS/MS-MS J. Environ. Monit. 2005, 7, 189-195
39. Volmer, D. A.; Mansoori, B.; Locke, S. J. Study of 4-quinolone antibiotics in biological samples by short-column liquid chromatography coupled with electrospray ionization tandem mass spectrometry Anal. Chem. 1997, 69, 4143-4155
40. Terzic, S.; Senta, I.; Matosic, M.; Ahel, M. Identification of biotransformation products of macrolide and fluoroquinolone antimicrobials in membrane bioreactor treatment by ultrahigh-performance liquid chromatography/quadrupole time-of-flight mass spectrometry.) Anal. Bioanal. Chem. 2011, 401, 353-363
41. http://mzmine.sourceforge.net (accessed Jan 17, 2014).
42. Pluskal, T.; Castillo, S.; Villar-Briones, A.; Oresic, M. MZmine 2: Modular framework for processing, visualizing, and analyzing mass spectrometry-based molecular profile data Bioinformatics 2010, 11, 395-405
43. Wu, L.; Liu, D. Q. Data-dependent tandem mass spectrometry of doubly protonated molecules in pharmaceutical analysis Rapid Commun. Mass Spectrom. 2007, 21, 455-458
44. Clemente, M.; Hermo, M. P.; Barrón, D.; Barbosa, J. Confirmatory and quantitative analysis using experimental design for the extraction and liquid chromatography-UV, liquid chromatography-mass spectrometry and liquid chromatography-mass spectrometry/mass spectrometry determination of quinolones in turkey muscle J. Chromatogr., A 2006, 1135, 170-178
45. Picó, Y.; Andreu, V. Fluoroquinolones in soil-risks and challenges Anal. Bioanal. Chem. 2007, 387, 1287-1299
46. Hermo, M. P.; Barrón, D.; Barbosa, J. Multiresidue determination of quinolones regulated by the European Union in bovine and porcine plasma. Application of chromatographic and capillary electrophoretic methodologies J. Chromatogr., A 2008, 1201, 1-14
47. Kaufmann, A.; Butcher, P.; Maden, K.; Widmer, M.; Giles, K.; Uría, D. Are liquid chromatography/electrospray tandem quadrupole fragmentation ratios unequivocal confirmation criteria? Rapid Commun. Mass Spectrom. 2009, 23, 985-998
48. Thermo Scientific Analytical Tools for Metabolism. Biotransformation Reference Guide, 2009.
49. http://foodbs.org/examples/milk (accessed Jan 17, 2014).
50. Rust, H.; Scheer, M.; Hallenbach, W. BAYER AG, Preparation of quinolone and naphthylidinone N -oxides as antibacterials. Patent ES 2 161 361 T3, January 12, 2001.
51. Badertscher, M.; Bischofberger, K.; Munk, M. E.; Pretsch, E. A novel formalism to characterize the degree of unsaturation of organic molecules J. Chem. Inf. Comput. Sci. 2001, 41, 889-893