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Whelan 1,2 Martin Danaher 1, Ambrose Furey 2

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Whelan 1,2 Martin Danaher 1, Ambrose Furey 2 Quantitative and confirmatory analysis of veterinary drug residues in food of animal origin by UPLC- MS/MS after QuEChERS clean-up Michelle Whelan 1,2 Martin Danaher 1, Ambrose Furey 2. Ashtown Food Research Centre 1, C ork Institute of Technology 2. Topics Covered • ProSafeBeef • Food Safety – Background – Anti-parasitic • Method Development – Existing method – New method – Sample preparation • Method Validation – Milk, Liver and Muscle • Method Performance • Future Work ProSafeBeef ProSafeBeef • Advancing Beef Safety and Quality through Research and Innovation: European Framework Programme 6 • The ProSafeBeef consortium is multidisciplinary and comprised of 41 participants from research institutes, universities, private companies and industry organizations from 13 European countries, as well as Brazil, United States, Canada, Australia and New Zealand. • ProSafeBeef is divided into 7 separate management/research areas • Piller 1 - Quantitative Risk assessment for microbial and chemical contaminants Aim of Chemical Contaminants section 1.4 of Pillar 1 • Develop assays for anthelmintic residues • Transfer method to project partners, QUB, AFBI, IAEA, and Microbioticos • Inter-laboratory studies • Survey of EU beef (n = 1000 samples) • Exposure assessment • Quantitative risk assessment of chemical residues in beef • Dissemination Europe Climates Sampling Plan ProSafeBeef • Important to identify the key anthelmintic drugs and their usage in different animal species • Also need knowledge of the time of application • Risk based approach is more likely to identify non-compliant results and will give greater consumer protection • Sampling is biased and may portray a negative image of food Food Safety Food Safety • Main concern over benzimidazoles is due to their teratogenic properties (males and females) – Research has shown that OFZ causes birth defects if used in pregnant ewes • Secondary metabolite is generally the most toxic – Oxfendazole more toxic than fenbendazole – Hydroxy-mebendazole more toxic than mebendazole Background • National Reference Laboratory for anthelmintic agents. • Veterinary drug residues are tested for at AFRC as part of the National Monitoring Plan. • Anthelmintics important in Ireland due to the extensive nature of farming • In early 2008: Four separate LC methods for anthelmintics in milk and liver (n=19 residues). • No method for flukicide and levamisole • Desired multi method for anthelmintics in milk, liver and muscle • Developed a multi method mid 2008 and demonstrated it at CRL in May 2009 Anthelmintics Anthelmintics drugs are used for controlling the following worms: Nematodes (roundworms) Cestodes (tapeworms) Trematodes (Flukes) Three main classes of drugs used for the treatment are: Benzimidazoles Avermectins Flukicides Economic losses Weight loss Poor wool growth and quality Reduced milk production Method development List of Analytes Abamectin Mebendazole Levamisole Doramectin Hydroxy Mebendazole Coumaphos Emamectin Amino Mebendazole Coumaphos-Oxon Eprinomectin Flubendazole Rafoxanide Ivermectin Hydroxy Flubendazole Oxyclozanide Moxidectin Amino Flubendazole Niclozamide Cambendazole Fenbendazole Nitroxinil Albendazole Fenbendazole Sulphone Bithionol Albendazole Sulphone Oxfendazole Clorsulon Albendazole Sulphoxide Triclabendazole Closantel Albendazole amino Oxibendazole Triclabendazole sulphone Sulphone 5 Hydroxy- Morantel Triclabendazole Thiabendazole Sulphoxide Thiabendazole Haloxon Existing LC-MS/MS method • Quechers sample preparation was developed in USDA by Brian Kinsella • LC-MS/MS method was developed using Agilent 1100 and an Applied Biosystems API 3000 using a Prodigy C18 column, (150 x 3, 5 µm) • Two injections (pos and neg modes) 24 mins each. • Two internal standards • Only detects TCB and TCB-SO • LOQ 5ppb • Kinsella et al. Current UPLC-MS/MS method • Modified sample preparation developed in USDA to detect lower levels – Scaled up Clean up step – Concentration step using DMSO • LC-MS/MS method was developed using Acquity UPLC and Waters MicroMass Quattro Premier XE using a HSS T3 column, (100 x 2.1 mm; 1.8 µm) • ONE injections (covers both pos and neg modes) 12.5 mins • 21 internal standards, 15 Deuterated • Detects all the TCB metabolites • LOQ < 2ppb UPLC Conditions • Column: HSS T3 (100 x 2.1 Time A% B% Curve mm; 1.8 µm) 0.00 100 0 1 • Column Temp. : 60 °C 0.50 100 0 6 • MPA : 0.01% CH 3COOH in 5.00 50 50 6 H 0 + ACN (90 + 10, v/v) 2 7.00 10 90 6 • MPB : 5 mM Ammon. Form. in MeOH + ACN (75 + 25, v/v) 8.50 10 90 6 • Flow rate: 0.6 ml min -1 8.51 0 100 6 • Injection: 5 µl 9.50 0 100 6 • Run time: 12.5 min 9.51 100 0 6 12.50 100 0 6 Sample Preparation for non-MRL Substances ••ExtractionExtraction 10 g sample + 12 ml MeCN Homogenise (only for liver and muscle) Add 4g MgSO 4 and 1g NaCl Shake for 1 minute and Centrifuge for 12 minutes ••CleanClean upup andand ConcentrationConcentration Pour supernatant into centrifuge tube containing 1.5g MgSO 4 and 0.5g C 18 Mix for 30 seconds and Centrifuge for 10 minutes Transfer 6 mls to a test tube containing 250µl of DMSO Evaporate MeCN under nitrogen (60 °C) ••AnalysisAnalysis Filter the extracts and add to auto sampler vial. Inject Sample Preparation for MRL Substances ••ExtractionExtraction 10 g sample + 12 ml MeCN Homogenise (only for liver and muscle) Add 4g MgSO 4 and 1g NaCl Shake for 1 minute and Centrifuge for 10 minutes ••CleanClean upup andand ConcentrationConcentration Add 1ml of the supernatant into micro-centrifuge tube containing 150mg MgSO 4 and 50mg C 18 Mix for 30 seconds and Centrifuge for 2 minutes ••AnalysisAnalysis Filter the extracts and add to auto sampler vial. Inject Method validation Method Validation According to 2002/657/EC guidelines. Specificity was carried out using 20 blank samples. Linearity: > 0.98 Recovery Experiments: - 1, 1.5, 2 times the chosen level, (or) 0.5, 1, 1.5 times MRL Within laboratory repeatability with single analyst - 1, 1.5, 2 times the chosen level, (or) 0.5, 1, 1.5 times MRL Within laboratory reproducibility with three analysts - 1, 1.5, 2 times the chosen level, (or) 0.5, 1, 1.5 times MRL CC α and CC β values were calculated at 1, 1.5, 2 times the chosen level, or 0.5, 1, 1.5 times MRL. S/N ratio is typically >100 Ion Ratios very consistent and reproducible through-out runs. Recovery at validated levels for Muscle 160.0 1 1.5 2 140.0 120.0 100.0 80.0 60.0 40.0 20.0 0.0 34.0 32.0 30.0 28.0 26.0 24.0 22.0 Within Laboratory Reproducibility - Muscle - Benz 20.0 18.0 % CV 16.0 14.0 12.0 10.0 8.0 6.0 4.0 2.0 0.0 0.5 Albendazole Albendazole-sulphoxide 1 Albendazole-sulphone 1.5 Albendazole-amino-sulphone Cambendazole Fenbendazole Oxfendazole Fenbendazole-sulphone Flubendazole Amino-flubendazole Hydroxy-flubendazole Mebendazole Amino-mebendazole Hydroxy-mebendazole Oxibendazole Triclabendazole Triclabendazole-sulphoxide Triclabendazole-sulphone Thiabendazole 5-hydroxy-thiabendazole 34.0 32.0 30.0 28.0 26.0 Within Laboratory Reproducibility - Muscle - Fluke 24.0 22.0 20.0 18.0 % CV 16.0 14.0 12.0 10.0 8.0 6.0 4.0 2.0 0.5 0.0 1 Levamisole 1.5 Bithionol Clorsulon Closantel Morantel - Aver Niclosamide Nitroxynil Oxyclozanide Rafoxanide Coumaphos Coumaphos-oxon Haloxon Abamectin Doramectin Emamectin Eprinomectin Ivermectin Moxidectin Recovery at validated levels for Milk 180.0 160.0 140.0 1 1.5 2 120.0 100.0 80.0 60.0 40.0 20.0 0.0 32.0 Within Laboratory Reproducibility - Milk - Benz 30.0 28.0 0.5 1 1.5 26.0 24.0 22.0 20.0 18.0 16.0 14.0 % CV % 12.0 10.0 8.0 6.0 4.0 2.0 0.0 Within Laboratory Reproducibility - Milk - Fluke and 30.0 28.0 Aver 26.0 1 1.5 2 24.0 22.0 20.0 18.0 % CV % 16.0 14.0 12.0 10.0 8.0 6.0 4.0 2.0 0.0 Recovery at validated levels for Liver 160.0 1 1.5 2 140.0 120.0 100.0 80.0 60.0 40.0 20.0 0.0 30.0 Within Laboratory Reproducibility - Liver - Benz 28.0 26.0 1 1.5 2 24.0 22.0 20.0 18.0 16.0 14.0 % CV % 12.0 10.0 8.0 6.0 4.0 2.0 0.0 42.0 Within Laboratory Reproducibility - Liver - Fluke - Aver 40.0 38.0 1 1.5 2 36.0 34.0 32.0 30.0 28.0 26.0 24.0 22.0 20.0 % CV % 18.0 16.0 14.0 12.0 10.0 8.0 6.0 4.0 2.0 0.0 CC α and CC β for Milk milk LOR/MRL CC CC β µg/kg µg/kg Albendazole 100 107.40 116.61 Albendazole-sulphoxide 100 122.75 145.50 Albendazole-sulphone 100 104.77 115.75 Albendazole-amino-sulphone 100 104.52 119.96 Cambendazole 2 0.70 1.20 Fenbendazole 10 10.79 12.16 Oxfendazole 10 12.05 13.78 Fenbendazole-sulphone 10 10.84 11.81 Flubendazole 2 1.53 2.61 Amino-flubendazole 2 0.82 1.41 Hydroxy-flubendazole 2 0.80 1.36 Mebendazole 2 0.70 1.19 Amino-mebendazole 2 0.92 1.56 Hydroxy-mebendazole 2 0.69 1.17 Oxibendazole 2 1.95 3.32 Triclabendazole 2 0.71 1.20 Triclabendazole-sulphoxide 2 0.90 1.53 Triclabendazole-sulphone 2 1.33 2.26 Thiabendazole 2 1.65 2.81 5-hydroxy-thiabendazole 2 1.49 2.54 CC α and CC β for Milk Milk LOR/MRL CC CC β µg/kg Levamisole 2 1.26 2.14 Bithionol 4 1.59 2.71 Clorsulon 4 0.87 1.48 Closantel 2 1.07 1.82 Morantel 50 57.89 71.15 Niclosamide 2 0.74 1.27 Nitroxynil 2 0.66 1.12 Oxyclozanide 10 14.36 20.1 Rafoxanide 2 0.80 1.36 Coumaphos 2 0.82 1.40 Coumaphos-oxon 2 0.87 1.48 Haloxon 2 0.89 1.52 Abamectin 2 0.77 1.31 Doramectin 2 1.13 1.92 Emamectin 2 0.74 1.26 Eprinomectin 20 22.03 24.61 Ivermectin 2 0.74 1.25 Moxidectin 40 45.04 51.88 CC α and CC β for Bovine Liver Liver LOR/MRL CC CC β µg/kg µg/kg Albendazole 1000 1092.30 1173.85 Albendazole-sulphoxide 1000 1385.08 3844.29 Albendazole-sulphone 1000 1396.67 2403.42 Albendazole-amino-sulphone 1000 1051.59 1169.45 Cambendazole 2 0.32 0.55 Fenbendazole 500 552.81 620.57 Oxfendazole 500 537.20 589.62 Fenbendazole-sulphone
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