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Mixed-mode liquid chromatography coupled to tandem mass spectrometry for the analysis of aminoglycosides in meat

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Abstract

A novel LC-MS/MS method has been developed for the determination of 13 aminoglycoside antibiotics in meat products. Among the chromatographic columns tested, the mixed-mode Obelisc R provided the best performance. Electrospray has been used for the coupling of the LC and the effect of temperature on the ionization has been evaluated. The mass spectra of AGs have been studied in order to select the most adequate precursor and product ions for quantitation and confirmation in SRM mode, showing that the single charged [M+H]+ provided better precisions than the double charged [M+2H]2+. Accurate mass measurements have been performed in order to confirm the molecular composition of the product ions, allowing the establishment of a new mechanism for some product ions of STR and DHSTR. A sample treatment based on an extraction and a SPE clean-up has been applied to a wide variety of meat products such as frankfurters; sausages; and minced meat of pork, veal, and chicken. Method limits of quantitation in the low microgram per kilogram level (1–50 μg kg−1), precisions %RSD below 15 % and accuracies expressed as relative errors below 23 % have been obtained, making the proposed method suitable for routine analysis.

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References

  1. Stead DA (2000) Current methodologies for the analysis of aminoglycosides. J Chromatogr B 747:69–93

    Article  CAS  Google Scholar 

  2. Bogialli S, Curini R, Di Corcia A, Laganà A, Mele M, Nazzari M (2005) Simple confirmatory assay for analyzing residues of aminoglycoside antibiotics in bovine milk: hot water extraction followed by liquid chromatography–tandem mass spectrometry. J Chromatogr A 1067:93–100

    Article  CAS  Google Scholar 

  3. European Commission (2003) Regulation (EC) No 1831/2003 of the European Parliament and of the Council of 22 September 2003 on additives for use in animal nutrition. Off J Eur Communities L268:29–43

    Google Scholar 

  4. Guthrie OW (2008) Aminoglycoside induced ototoxicity. Toxicology 249:91–96

    Article  Google Scholar 

  5. Cherlet M, De Baere S, De Backer P (2007) Quantitative determination of dihydrostreptomycin in bovine tissues and milk by liquid chromatography-electrospray ionization-tandem mass spectrometry. J Mass Spectrom 42:647–656

    Article  CAS  Google Scholar 

  6. European Commission (2009) Council Regulation (EEC) No.37/2010 of 22 December 2009: on pharmacologically active substances and their classification regarding maximum residue limits in foodstuffs of animal origin. Off J Eur Communities L15:1

    Google Scholar 

  7. Blasco C, Picó Y, Torres CM (2007) Progress in analysis of residual antibacterials in food. TrAC Trends Anal Chem 26:895–913

    Article  CAS  Google Scholar 

  8. Bogialli S, Di Corcia A (2009) Recent applications of liquid chromatography-mass spectrometry to residue analysis of antimicrobials in food of animal origin. Anal Bioanal Chem 395:947–966

    Article  CAS  Google Scholar 

  9. McGlinchey TA, Rafter PA, Regan F, McMahon GP (2008) A review of analytical methods for the determination of aminoglycoside and macrolide residues in food matrices. Anal Chim Acta 624:1–15

    Article  CAS  Google Scholar 

  10. Gaugain-Juhel M, Delepine B, Gautier S, Fourmond MP, Gaudin V, Hurtaud-Pessel D, Verdon E, Sanders P (2009) Validation of a liquid chromatography-tandem mass spectrometry screening method to monitor 58 antibiotics in milk: a qualitative approach. Food Addit Contam 26:1459–1471

    Article  CAS  Google Scholar 

  11. Róna K, Klausz G, Keller E, Szakay M, Laczay P, Shem-Tov M, Székely-Körmöczy P (2009) Determination of paromomycin residues in turkey tissues by liquid chromatography/mass spectrometry. J Chromatogr B 877:3792–3798

    Article  Google Scholar 

  12. Hornish RE, Wiest JR (1998) Quantitation of spectinomycin residues in bovine tissues by ion-exchange high-performance liquid chromatography with post-column derivatization and confirmation by reversed-phase high-performance liquid chromatography-atmospheric pressure chemical ionization tandem mass spectrometry. J Chromatogr A 812:11

    Article  Google Scholar 

  13. Kaufmann A, Butcher P, Maden K (2012) Determination of aminoglycoside residues by liquid chromatography and tandem mass spectrometry in a variety of matrices. Anal Chim Acta 711:46–53

    Article  CAS  Google Scholar 

  14. Almeida MP, Rezende CP, Souza LF, Brito RB (2012) Validation of a quantitative and confirmatory method for residue analysis of aminoglycoside antibiotics in poultry, bovine, equine and swine kidney through liquid chromatography-tandem mass spectrometry. Food Addit Contam 29:517–525

    Article  CAS  Google Scholar 

  15. Lehotay SJ, Mastovska K, Lightfield AR, Nunez A, Dutko T, Ng C, Bluhm L (2013) Rapid analysis of aminoglycoside antibiotics in bovine tissues using disposable pipette extraction and ultrahigh performance liquid chromatography-tandem mass spectrometry. J Chromatogr A 1313:103–112

    Article  CAS  Google Scholar 

  16. U.S. Department of Agriculture, Food Safety and Inspection Service, R01b: screening and confirmation of aminoglycosides by LC-MS/MS, chemistry laboratory guidebook, April 2013 http://www.fsis.usda.gov/wps/portal/fsis/topics/science/laboratories-and-procedures/guidebooks-and-methods/chemistry-laboratory-guidebook. Accessed Jan 2014

  17. Alpert AJ (1990) Hydrophilic-interaction chromatography for the separation of peptides, nucleic acids and other polar compounds. J Chromatogr 499:177–196

    Article  CAS  Google Scholar 

  18. Kahsay G, Song H, Van Schepdael A, Cabooter D, Adams E (2014) Hydrophilic interaction chromatography (HILIC) in the analysis of antibiotics. J Pharm Biomed Anal 87:142–154

    Article  CAS  Google Scholar 

  19. Bohm DA, Stachel CS, Gowik P (2013) Validation of a method for the determination of aminoglycosides in different matrices and species based on an in-house concept. Food Addit Contam 30:1037–1043

    Article  CAS  Google Scholar 

  20. Kumar P, Rubies A, Companyo R, Centrich F (2012) Determination of aminoglycoside residues in kidney and honey samples by hydrophilic interaction chromatography-tandem mass spectrometry. J Sep Sci 35:2710–2717

    Article  CAS  Google Scholar 

  21. Kumar P, Rubies A, Companyo R, Centrich F (2012) Hydrophilic interaction chromatography for the analysis of aminoglycosides. J Sep Sci 35:498–504

    Article  CAS  Google Scholar 

  22. Chen Y, Hu X, Xiao X (2010) Sample preparation for determination of neomycin in swine tissues by liquid chromatography-fluorescence detection. Anal Lett 43:2496–2504

    Article  CAS  Google Scholar 

  23. Suhren G, Knappstein K (1998) Detection of incurred dihydrostreptomycin residues in milk by liquid chromatography and preliminary confirmation methods. Analyst 123:2797–2801

    Article  CAS  Google Scholar 

  24. Pyun CW, Abd El-Aty AM, Hashim MM, Shim JH, Lee SK, Choi KD, Park KH, Shin HC, Lee C (2008) Monitoring of streptomycin and dihydrostreptomycin residual levels in porcine meat press juice and muscle via solid-phase fluorescence immunoassay and confirmatory analysis by liquid chromatography after post-column derivatization. Biomed Chromatogr 22:254–259

    Article  CAS  Google Scholar 

  25. Kotretsou SI (2004) Determination of aminoglycosides and quinolones in food using tandem mass spectrometry: a review. Crit Rev Food Sci Nutr 44:173–184

    Article  CAS  Google Scholar 

  26. Grahek R, Zupancic-Kralj L (2009) Identification of gentamicin impurities by liquid chromatography tandem mass spectrometry. J Pharm Biomed Anal 50:1037–1043

    Article  CAS  Google Scholar 

  27. (2002) Commission Decision (EC) No. 2002/657/EC of 12 August 2002 implementing Council Directive 96/23/EC concerning the performance of analytical methods and the interpretation of results. Off J Eur Communities L 221:8

  28. Lammerhofer M, Richter M, Wu J, Nogueira R, Bicker W, Lindner W (2008) Mixed-mode ion-exchangers and their comparative chromatographic characterization in reversed-phase and hydrophilic interaction chromatography elution modes. J Sep Sci 31:2572–2588

    Article  Google Scholar 

  29. Novakova L, Solichova D, Solich P (2009) Hydrophilic interaction liquid chromatography–charged aerosol detection as a straightforward solution for simultaneous analysis of ascorbic acid and dehydroascorbic acid. J Chromatogr A 1216:4574–4581

    Article  CAS  Google Scholar 

  30. Bu X, Skrdla PJ, Dormer PG, Bereznitski Y (2010) Separation of triphenyl atropisomers of a pharmaceutical compound on a novel mixed mode stationary phase: a case study involving dynamic chromatography, dynamic NMR and molecular modeling. J Chromatogr A 1217:7255–7264

    Article  CAS  Google Scholar 

  31. Oertel R, Neumeister V, Kirch W (2004) Hydrophilic interaction chromatography combined with tandem-mass spectrometry to determine six aminoglycosides in serum. J Chromatogr A 1058:197–201

    Article  CAS  Google Scholar 

  32. Oertel R, Renner U, Kirch W (2004) Determination of neomycin by LC–tandem mass spectrometry using hydrophilic interaction chromatography. J Pharm Biomed Anal 35:633–638

    Article  CAS  Google Scholar 

  33. Bock K, Pedersen C, Heding H (1974) Carbon-13 NMR spectroscopic study of α- and β-streptomycin. J Antibiot 27:139–140

    Article  CAS  Google Scholar 

  34. Girod M, Moyano E, Campbell DI, Cooks RG (2011) Accelerated bimolecular reactions in microdroplets studied by desorption electrospray ionization mass spectrometry. Chem Sci 2:501

    Article  CAS  Google Scholar 

  35. Zhu WX, Yang JZ, Wei W, Liu YF, Zhang SS (2008) Simultaneous determination of 13 aminoglycoside residues in foods of animal origin by liquid chromatography-electrospray ionization tandem mass spectrometry with two consecutive solid-phase extraction steps. J Chromatogr A 1207:29–37

    Article  CAS  Google Scholar 

  36. Goolsby BJ, Brodbelt JS (2000) Analysis of protonated and alkali metal cationized aminoglycoside antibiotics by collision-activated dissociation and infrared multi-photon dissociation in the quadrupole ion trap. J Mass Spectrom 35:1011–1024

    Article  CAS  Google Scholar 

  37. Hu P, Chess EK, Brynjelsen S, Jakubowski G, Melchert J, Hammond RB (2000) Collisionally activated dissociations of aminocyclitol.aminoglycoside antibiotics and their application in the identification of a new compound in trobramycin samples. J Am Soc Mass Spectrom 11:200–209

    Article  CAS  Google Scholar 

  38. Ishii R, Horie M, Chan W, MacNeil J (2008) Multi-residue quantitation of aminoglycoside antibiotics in kidney and meat by liquid chromatography with tandem mass spectrometry. Food Addit Contam 25:1509–1519

    Article  CAS  Google Scholar 

  39. Chiaochan C, Koesukwiwat U, Yudthavorasit S, Leepipatpiboon N (2010) Efficient hydrophilic interaction liquid chromatography-tandem mass spectrometry for the multiclass analysis of veterinary drugs in chicken muscle. Anal Chim Acta 682:117–129

    Article  CAS  Google Scholar 

  40. Gremilogianni AM, Megoulas NC, Koupparis MA (2010) Hydrophilic interaction vs ion pair liquid chromatography for the determination of streptomycin and dihydrostreptomycin residues in milk based on mass spectrometric detection. J Chromatogr A 1217:6646–6651

    Article  CAS  Google Scholar 

  41. Cherlet M, De Baere S, De Backer P (2000) Determination of gentamicin in swine and calf tissues by high-performance liquid chromatography combined with electrospray ionization mass spectrometry. J Mass Spectrom 35:1342–1350

    Article  CAS  Google Scholar 

  42. Berrada H, Molto JC, Manes J, Font G (2010) Determination of aminoglycoside and macrolide antibiotics in meat by pressurized liquid extraction and LC-ESI-MS. J Sep Sci 33:522–529

    Article  CAS  Google Scholar 

  43. Bousova K, Senyuva H, Mittendorf K (2013) Quantitative multi-residue method for determination antibiotics in chicken meat using turbulent flow chromatography coupled to liquid chromatography-tandem mass spectrometry. J Chromatogr A 1274:19–27

    Article  CAS  Google Scholar 

  44. Hurtaud-Pessel D, Jagadeshwar-Reddy T, Verdon E (2011) Development of a new screening method for the detection of antibiotic residues in muscle tissues using liquid chromatography and high resolution mass spectrometry with a LC-LTQ-Orbitrap instrument. Food Addit Contam 28:1340–1351

    Article  CAS  Google Scholar 

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Acknowledgments

The authors gratefully acknowledge the financial support received from Spain’s Ministry of Science and Technology under project CTQ2012-30836. Élida Alechaga is grateful to Spain’s Ministry of Education for an FPU grant. The authors also wish to thank Cromlab (Spain) for kindly providing the chromatographic column.

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Authors and Affiliations

  1. Department of Analytical Chemistry, University of Barcelona, Diagonal 645, 08028, Barcelona, Spain

    Élida Alechaga, Encarnación Moyano & M. Teresa Galceran

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  1. Élida Alechaga
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  2. Encarnación Moyano
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  3. M. Teresa Galceran
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Correspondence to Encarnación Moyano.

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Alechaga, É., Moyano, E. & Galceran, M.T. Mixed-mode liquid chromatography coupled to tandem mass spectrometry for the analysis of aminoglycosides in meat. Anal Bioanal Chem 406, 4941–4953 (2014). https://doi.org/10.1007/s00216-014-7912-7

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  • DOI: https://doi.org/10.1007/s00216-014-7912-7

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