Application of APGC-MS/MS for determination of PCDD/Fs and PCBs in Feed and Food Matrices

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1 eseminar Advances in Food Safety Analysis September 1-19, 213 Application of APGC-MS/MS for determination of PCDD/Fs and PCBs in Feed and Food Matrices Alexander Kotz 1, Wim Traag 2, Helmut Winterhalter 1, Rainer Malisch 1 and Jody Dunstan 3 1 European Union Reference Laboratory for Dioxins and PCBs in Feed and Food, Freiburg, Germany 2 RIKILT- Institute of Food Safety, Wageningen, The Netherlands 3 Waters, Manchester, UK 1 / APGC-MS/MS

2 PCDD/Fs and PCBs 2 / APGC-MS/MS

3 Dioxins and PCBs Toxic and persistent organic contaminants (Stockholm convention POPs): Polychlorinated Dibenzo-p-dioxins (PCDDs) and Dibenzofurans (PCDFs) O O Br Cl x Cl y Br x 'Cl y ' PBr PCDD PXDD / ClDD C 12 C 12 H H 8-n 8-n Cl X Cl n O 2 2 Br Cl Cl x y O Br Cl 'Cl x y ' y PBr PXDF PCDF / ClDF C 12 H 8-n X Cl n n O 21 possible congeners, 17 toxicologically relevant Polychlorinated Biphenyls (PCBs) with dioxin-like activity (DL-PCBs) 29 possible congeners, 12 with dioxin-like activity C 12 H 1-n Cl n 3 / APGC-MS/MS

4 Chemical properties: Dioxins and PCBs Properties, sources, health effects Lipophilic, persistent in the environment, ability for biomagnification and bioconcentration PCDD/Fs are formed unintentionally as by-products in chemical and combustion processes PCBs were intentionally produced for various technical applications 9 % of human exposure through food (especially food of animal origin) Health effects of PCDD/Fs and DL-PCBs (long-term exposure): Possible human carcinogens Reproductive and developmental problems Damage of the immune system, interference with hormones,... 4 / APGC-MS/MS

5 EU Criteria for Screening and Confirmatory Methods 5 / APGC-MS/MS

6 Current EU regulations on analytical criteria Methods of analysis (Commission Regulations (EC) No 152/29 (Feed), (EU) No 252/212 (Food)): Screening methods: Selection of samples exceeding maximum or action levels (cost-effective high sample-throughput, aim to avoid false-compliant results) e.g. GC-MS, GC-MS/MS methods, bioanalytical methods Confirmation of results in samples with significant level with a confirmatory method Confirmatory methods: Unequivocally identification and quantification of PCDD/Fs and DL-PCBs at level of interest Confirmation of results obtained from screening Determination of low background levels Use of all 13 C-labelled internal standards (PCDD/Fs and DL-PCBs) GC-HRMS methods Screening with bioanalytical or physico-chemical methods Confirmatory methods False-compliant rate < 5 % Trueness - 2 to + 2 % Repeatability (RSD r ) < 2 % Within-laboratory reproducibility (RSD R ) < 25 % < 15 % 6 / APGC-MS/MS

7 Application of MS/MS for determination of PCDD/Fs and PCBs Publications: Comparison of GC-MS and GC-MS/MS (environmental, technical samples): Simon et al. 1988, Hardin et al. 1989, Reiner et al. 199, Curvin et al. 1989, Clement et al Application of ion-trap-ms, comparison of techniques: March et al. 2, Hayward et al. 21, Focant et al. 21, 25, Kemmochi et al. 22, Malavia et al Development of harmonized criteria in 21: Malisch et al. 21 Lack of sensitivity of GC-MS/MS in comparison to GC-HRMS (food, feed) Possible use of GC-MS/MS as screening method GC-HRMS as confirmatory method 7 / APGC-MS/MS

8 Application of MS/MS for determination of PCDD/Fs and PCBs Recent developments: Comparison of GC-MS/MS and GC-HRMS (food, feed) Bernsmann et al. 211, Ingelido et al. 211, Kotz et al. 211, Leondiadis et al Working group of EURL and network of NRLs Evaluation of GC-MS/MS and development of analytical criteria Proposed amendments of analytical criteria for inclusion of MS/MS as confirmatory method (Kotz et al. 213) 8 / APGC-MS/MS

9 Proposed amendments for GC-MS/MS by network of EURL and NRLs* Amendment of criteria for confirmatory methods for inclusion of MS/MS (tandem mass spectrometry): Calculation of LOQ based on signal-to-noise ratio or lowest concentration point on calibration curve Monitoring of at least 2 specific precursor ions, each with one specific corresponding transition product ion for all labelled and unlabelled analytes in the scope of analysis (comparable to GC-HRMS) Resolution for each quadrupole equal to or better than unit mass resolution (unit mass resolution: sufficient resolution to separate two peaks one mass unit apart) in order to minimize possible interferences on the analytes of interest Maximum permitted tolerance of relative ion intensities of ± 15% for selected transition product ions in comparison to calculated or measured values (average from calibration standards) Further criteria as described, for example, in standard EN and/or in EPA methods 1613 and 1668 as revised, except the obligation to use GC-HRMS have to be followed * Kotz A et al. (212) Organohalogen Compd 74: / APGC-MS/MS

10 Methods 1 / APGC-MS/MS

11 Extraction and Clean-up Food/Feed sample Sample pre-treatment Extraction Determination of lipid content Gel permation chromatography Multi-layer silica column Florisil column n-heptane fraction Toluene fraction Carbon column for PCB Carbon column for PCDD/F n-hexane fraction n-hexane/toluene fraction Toluene fraction Toluene fraction Indicator PCBs Mono-ortho-PCBs Non-ortho-PCBs Multi-layer silica column GC-HRMS PCDD/Fs APGC-MS/MS 11 / APGC-MS/MS

12 APGC Ionization 12 / APGC-MS/MS

13 APGC-MS/MS parameters Waters Xevo TQ-S with APGC source APGC and MS/MS settings APGC Source Ionisation API+ Source Dry N 2 Source temperature 15 C Corona current 2. µa Sampling cone voltage 35 V Cone gas flow 2 L/h Auxiliary gas flow 3 L/h GC make-up flow 15 ml/min Multiple reaction monitoring Precursor Ion M + Product Ion M-COCl + Collision energy 31 V Collision gas flow.3 ml/min (Argon) Cycle time ca..4 s Dwell time 48 ms 13 / APGC-MS/MS

14 APGC-MS/MS parameters Agilent GC 789A Injector and GC settings (5 µl injection) Injector settings (PCDD/Fs) Injector Injector liner Injected volume Vent pressure / flow / end time PTV programme Multimode injector, solvent vent mode Deactivated dimpled cold splitless liner, 2mm ID 5 µl (toluene) 5 kpa, 1 ml/min,.5 min 1 C,.5 min, 7 C/min, 34 C, 2 min GC settings (PCDD/Fs) Analytical column DB-5MS 6 m x.25 mm,.25 µm (Agilent) Uncoated column (heated transfer line) Rxi guard column ca..5 m x.25 mm (Restek) Carrier gas / flow Helium, 1.4 ml/min (constant flow) GC oven programme 9 C, 1.5 min, 2 C/min to 25 C, 2.5 C/min to 285 C, 25 C/min to 34 C, 6.5 min Heated transfer line 36 C 14 / APGC-MS/MS

15 Working range and limit of quantification 15 / APGC-MS/MS

16 Intensity Working range / LOQ Current Regulations TEQ Demonstration of performance of a method in the range of the level of interest (e.g..5x, 1x and 2x), with an acceptable CV Limit of quantification about 1/5th of the level of interest Difference between upper bound and lower bound Congener Detectable quantities of PCDD/Fs in upper femtogram range Specific limit of quantification of an individual congener: concentration of an analyte in the extract of a sample which produces an instrumental response at two different ions to be monitored with an S/N (signal/noise) ratio of 3:1 for the less sensitive signal Peak-to-peak signal-to-noise ratio S/N = 6:1 Signal intensity Noise Time Illustration signal-to-noise-ratio: Sigma-Aldrich 16 / APGC-MS/MS

17 Proposed amendments of current criteria Congener LOQ Inclusion of two different approaches for calculation of the LOQ Approach 1: Calculation of LOQ from signal-to-noise ratio (as defined in current regulations) Approach 2: Calculation based on calibration curve, if signal-to-noise ratio does not provide reliable results: "Lowest concentration point on a calibration curve that gives an acceptable ( 3 %) and consistent (measured at least at the start and at the end of an analytical series of samples) deviation to the average relative response factor calculated for all points on the calibration curve in each series of samples." 17 / APGC-MS/MS

18 % % Signal-to-noise ratio Calibration Eich_1L cdx_ > 257 S/N:PtP= Mar-213 7:5:59 32 > 257 (TCDD) 1.24e4 S/N peak-to-peak 19:1 (noise range 2 min) 62.5 fg 2,3,7,8-TCDD 18.6 Time Calculation of reasonable LOQ from signal-to-noise-ratio theoretically possible, but ion ratio and relative response factors important additional criteria! Eich_1L 1:2 cdx_ > 257 S/N:PtP= Mar-213 2:45:21 32 > 257 (TCDD) 2.52e3 S/N peak-to-peak 3:1 (noise range 2 min) 3.1 fg 2,3,7,8-TCDD Time 18 / APGC-MS/MS

19 Ion ratio and relative response factor Proposed criteria for MS/MS as confirmatory method Calculation of LOQ based on calibration curve: Relative ion intensities within ± 15% of calculated or measured values Relative response factor (RRF) of lowest concentration point on a calibration with deviation 3 % of average relative response factor 19 / APGC-MS/MS

20 Relative Abundance Calculation of ion abundance ratios MS/MS Quan Ion Precursor Ion C 12 H 35 4 Cl 4 O 2 Precursor Ion C 12 H 35 4 Cl 37 3 ClO 2 Relative Abundance 78 Relative Abundance 1 -CO 35 Cl TCDD -CO 37 Cl Target Ion -CO 35 Cl C 12 H 4 35 Cl 3 37 ClO H 4 35 Cl 2 37 Cl 2 O 2 C 12 H 4 35 Cl 4 O C 12 H 4 35 Cl 37 Cl 3 O m/z Product Ion C 11 H 4 35 Cl 3 O Product Ion C 11 H 4 35 Cl 3 O Product Ion C 11 H 4 35 Cl 2 37 ClO Probability 1 % Probability 25 % Probability 75 % Calculated ion abundance ratio (Quan Ion / Target Ion): 1.4 Calculated ion abundance ratio comparable with measured ratios, if identical collision energy and collision gas pressure/flow applied 2 / APGC-MS/MS

21 Calculated ion abundance ratios MS/MS Depending on... Relative abundance of selected precursor ion Probability of loss of CO 35 Cl and CO 37 Cl for formation of each product ion Congener Transition Ratio Congener Transition Ratio 12 C 13 C 12 C 13 C 12 C 13 C 12 C 13 C TCDD 32 > > > > TCDF 34 > > > > PeCDD 354 > > > > PeCDF 338 > > > > HxCDD 39 > > > > HxCDF 374 > > > > HpCDD 424 > > > > HpCDF 48 > > > > OCDD 458 > > > > OCDF 442 > > > > / APGC-MS/MS

22 Ion abundance ratio PCDD/F Comparison: Calibration Calculated values Mean of E1L 1:2* E5L QC limits around the theoretical ion abundance ratios: ± 15 % Calculated (+/- 15%) Calibration *Inclusion of dilutions in calibration depending on deviations for ion ratio, response factor 22 / APGC-MS/MS

23 E1L 1:2 E1L 1:2 E1L 1:2 E1L 1:2 E1L 1:1 E1L 1:1 E1L 1:1 E1L 1:1 E1L 1:5 E1L 1:5 E1L 1:5 E1L 1:5 E1L 1:2 E1L 1:2 E1L 1:2 E1L 1:2 E1L E1L E1L E1L E2L E2L E2L E2L E3L E3L E3L E3L E4L E4L E4L E4L E5L E5L E5L E5L Relative Response Factor Deviation of mean [%] E1L 1:2 E1L 1:2 E1L 1:2 E1L 1:2 E1L 1:1 E1L 1:1 E1L 1:1 E1L 1:1 E1L 1:5 E1L 1:5 E1L 1:5 E1L 1:5 E1L 1:2 E1L 1:2 E1L 1:2 E1L 1:2 E1L E1L E1L E1L E2L E2L E2L E2L E3L E3L E3L E3L E4L E4L E4L E4L E5L E5L E5L E5L Ion abundance ratio Deviation of theoretical value [%] Evaluation of calibration runs Calculation of LOQ ,3,7,8-TCDF Calculated ratio: Fourfold injection of each calibration standard including dilutions LOQ based on ion ratio and RRF: E1L 1:5 (=12.5 fg) fg 62.5 fg on column 2.5 pg ,3,7,8-TCDF RRF 2 3 Calculation for every congener for every sequence necessary Additional consideration of recovery and sample intake / APGC-MS/MS -3

24 Comparison of results HRMS MS/MS 24 / APGC-MS/MS

25 Deviation of MS/MS results of HRMS [%] Food / Feed Samples PCDD/F Deviation of MS/MS results from HRMS Measurement of same extracts using GC-HRMS and APGC-MS/MS Comparison of APGC- MS/MS results with HRMS QC-charts WHO-PCDD/F-TEQ [pg/g fat, wet weight, ng/kg product (12% moisture)] Eggs Feed Fish Human milk Meat/Fat/Oil APGC-MS/MS results comparable with HRMS: deviation mostly < 2 % Higher deviations of MS/MS at low concentrations possibly caused by different calculation of LOQ 25 / APGC-MS/MS

26 Deviation of MS/MS results [%] Trueness PT sample and QC material Deviation of APGC-MS/MS results from reference values (mean 6.8 %) Comparison of APGC- MS/MS results with PT assigned values or median of HRMS QC-charts WHO-PCDD/F-TEQ [pg/g fat, ng/kg product (12% moisture)] PT assigned value HRMS QC-chart median Deviations mostly < 2 % Deviations > 2 % for single analysis acceptable, if average value 2 % Trueness: Closeness of agreement between the average value obtained from a large series of test results and an accepted reference value. (Commission Decision 22/657/EC) For confirmatory methods: -2 to + 2 % 26 / APGC-MS/MS

27 [pg WHO-TEQ/g fat] [pg/g fat] Repeatability (1) Animal fat Mixed animal fat [pg/g fat] Fivefold injection of food/feed extracts: WHO-TEQ: CV < 3 % Major congeners: CV < 12 % (contribution TEQ > 5 %) Mixed animal fat [pg TEQ/g fat] GC-HRMS (QC-chart) APGC-MS/MS / APGC-MS/MS

28 322 > Apr-213 1:34:42 Repeatability 1.2e4 (2) 13-Apr-213 9:53: > (TCDD) Animal fat 7:49:35-2,3,7,8-TCDD 13-Apr e > (TCDD) 13-Apr e4 9:12: > (TCDD) > (TCDD) e > (TCDD) e > (TCDD) e > (TCDD) e4 32 > > (TCDD) e fg 2,3,7,8-TCDD > (TCDD) 13-Apr e4 8:3:53 Fivefold injection of same > (TCDD) 1.2e4 sample extract of animal fat: 2,3,7,8-TCDD: Mean :.2 pg/g fat CV: 4 % QK2_T T Time cdx_ Smooth(Mn,1x1) % cdx_ Smooth(Mn,1x1) QK2_T T % Time Time Time % F1:MRM of 8 channels,api > e min 2,3,7,8-12 C-TCDD F1:MRM of 8 channels,api > e min cdx_ Smooth(Mn,1x1) QK2_T T Time F1:MRM of 8 channels,api > e+5 % cdx_ Smooth(Mn,1x1) QK2_T T % 2,3,7,8-13 C-TCDD min F1:MRM of 8 channels,api > e+5 % min 28 / APGC-MS/MS

29 Reduction of clean-up (1) Method Food/Feed sample Sample pre-treatment Extraction Determination of lipid content Check of possibility of reduction of number of clean-up steps and applicability of faster screening / confirmatory method Comparison between normal and reduced clean-up Gel permation chromatography Carbon column PCDD/Fs Multi-layer silica column Florisil column Carbon column Di-ortho-PCBs Mono-ortho-PCBs Non-ortho-PCBs Reduction of number of clean-up steps: I. Skip of carbon column for cleaning of PCDD/F fraction II. Skip of florisil column (for separation of PCDD/Fs and PCBs) and carbon column 29 / APGC-MS/MS

30 Reduction of clean-up (2) Samples Test with different naturally contaminated food samples Mixed animal fat Fish oil Hen s eggs Comparison of results of MS/MS with target values from HRMS-QC charts 3 / APGC-MS/MS

31 [pg/g fat] [pg/g fat] [pg/g fat] Comparison of congener results Mixed animal fat Fish oil Interferences Hen s eggs Comparable results for animal fat and hen s eggs Increase of TEQ by 4 % for fish oil 4 2 GC-HRMS (QC-chart) APGC-MS/MS (normal cleanup) APGC-MS/MS (without carbon column) APGC-MS/MS (without florisil and carbon) 31 / APGC-MS/MS

32 % % % % % % % % % % % % Mixed animal fat QK2 I (normal) 18-May-213 1:23:19 cdx_ > (TCDD C13) 1.5e cdx_ > (TCDD C13) 1.5e cdx_ > (TCDD) 1.5e4 322 > 259 Normal clean-up Occurrence of additional peaks with less number of clean-up steps No considerable increasing of baseline noise for APGC-MS/MS observed cdx_ > (TCDD) 1.5e4 32 > fg 2,3,7,8-TCDD Time QK2 II (-carbon) 18-May-213 3:28:2 cdx_ > (TCDD C13) 1.5e4 Without carbon column cdx_ > (TCDD C13) e QK2 III (-carbon -florisil) 18-May-213 4:51:1 cdx_ > (TCDD C13) e4 Without florisil, carbon column cdx_ > (TCDD C13) 1.5e cdx_ > (TCDD) 1.5e cdx_ > (TCDD) 1.5e4 5 fg 2,3,7,8-TCDD Time cdx_ > (TCDD) 1.5e cdx_ > (TCDD) 1.5e fg 2,3,7,8-TCDD Time 32 / APGC-MS/MS

33 Summary First experiences show sufficient sensitivity of the APGC-MS/MS for monitoring of maximum and action levels for PCDD/Fs in feed and food matrices Results for APGC-MS/MS comparable with GC-HRMS and able to meet current analytical criteria of EU regulations Application of different clean-up methods show, that the extraction and clean-up steps have considerable influence on the analytical results Interferences in chromatograms Deviations of MS/MS results from target value Interfering substances not separable by HRMS or MS/MS Application of 13 C-labeled internal standards for all relevant congeners advisable for MS/MS for possible correction of interfering substances influencing the ionisation 33 / APGC-MS/MS

34 Conclusions Criteria for MS/MS Proposed amendments allow use of GC-MS/MS (tandem mass spectrometry) as confirmatory methods (alternative to GC-HRMS) Comparable strict criteria also for MS/MS systems (as for HRMS) in order to maintain the requested high analytical quality and reliability for confirmation of the levels of PCDD/Fs and DL-PCBs Proposed amendments of EU regulations for application of GC- MS/MS as confirmatory method can be met by the EI-GC-MS/MS and APGC-MS/MS systems Apart from the detection system (in this case HRMS and MS/MS), extraction and clean-up process have a profound influence on the quality of the analytical results. 34 / APGC-MS/MS

35 Acknowledgements We would like to thank our colleagues at the EU-RL/ Kornelia Adamovic, Katharina Djuchin, Stefan Leswal, Indra Peters, Renate Tritschler, Jutta Schächtele and Kerstin Wahl for their technical and scientific support, the network of the EU-RL and the National Reference Laboratories for Dioxins and PCBs in Feed and Food for their scientific support, the European Commission for the financial support of the work of the EU-RL and Waters for providing an APGC-MS/MS system. Thank you very much for your attention! 35 / APGC-MS/MS

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