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Multi-Residue Veterinary Drug Analysis of >200 Compounds Using MRM

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Multi-Residue Veterinary Drug Analysis of >200 Compounds Using MRM Multi-residue veterinary drug analysis of >200 compounds using MRM Spectrum mode by LC-MS/MS David Baker1, Laetitia Fages2, Eric Capodanno2, Neil Loftus1 1Shimadzu, Manchester, UK 2 Phytocontrol, Nimes, France 3. Results 3.1 Library identification using MRM Spectrum mode 3-2. Quantitation using MRM Spectrum mode 1. Introduction To assess the robustness of this approach the same sample was repeatedly injected using a Compound name Chlortetracycline OH O OH O O Chlortetracycline MRM Spectrum OH O OH O O method that compiled with the identification criteria set out in the EU guidelines OH 444.00 OH Veterinary drugs are used for therapeutic, metaphylactic, prophylactic and growth Accurate mass 479.1216 [M+H]+ Similarity Score 98 NH SANTE/11945/2015 that requires the retention time and the ion ratio from at least 2 MRM promotion purposes. To provide an assurance that food from animals is safe with regards Formula C22H23ClN2O8 2 Matrix Salmon 461.95 NH2 CAS 57-62-5 154.00 274.95 285.85 transitions to be within acceptable tolerance limits. The absolute response and signal variability to residues of veterinary medicines, regulatory authorities have established Maximum OH 98.05 303.05 H H 260.05 H H OH was compared to a method using a higher number of fragment ions (Table 2). Both methods Residue Limits (MRL’s) for certain drugs in target tissues and animal species and has also 370.95 MRM Spectrum Mode Cl HO CH3 N 0 Cl HO CH3 N 11 MRM’s acquired for H C CH H C CH resulted in a variance of less than 4%RSD (n=10 for each method; 10pg/uL spiked into salmon identified pharmacologically active compounds that are prohibited and considered a 3 3 260.05 303.05 370.95 3 3 chlortetracycline at 10pg/uL in egg. 98.05 154.00 274.95 285.85 Compound name Chlortetracycline matrix). hazard at any level (EU regulation EC 37/2010; Commission Decision 2003/181/EC; 1:479.10>444.00 (+) CE: -23V Precursor 479.10 [M+H]+ 156.05 Compound name Sulfamerazine 2:479.10>461.95 (+) CE: -35V MRM Spectrum mode 461.95 8.89e5 Sulfamerazine 21CFR Part 556 Tolerances for Residues of New Animal Drugs in Food). In this work, we Formula C22H23ClN2O8 Precursor 265.10 [M+H]+ Chlortetracycline Library MRM Spectrum 444.00 1pg/uL 3:479.10>154.00 (+) CE: -34V Higher specificity 92.05 108.05 Formula C11H12N4O2S CAS 57-62-5 Matrix Beef describe a method that delivers highly sensitive and selective triple quadrupole detection 4:479.10>98.05(+) CE: -45V Higher reporting confidence 100 150 200 250 300 350 400 450 m/z 172.05 CAS 127-79-7 together with MRM Spectrum mode to reduce false positive and false negative reporting. 5:479.10>260.05(+) CE: -60V Library searchable fragment data. 65.00 110.05 6:479.10>303.05(+) CE: -37V The number of precursor-fragment ion transitions Chlortetracycline 444.00 Chlortetracycline 444.00 Chlortetracycline 444.00 N MRM Spectrum mode acquires a high number of fragment ion transitions for each target 7:479.10>300.80(+) CE: -45V 80.05 O O monitored is limited only by the structural chemistry Similarity Score 99 Similarity Score 98 Similarity Score 99 38.95 66.05 93.10 199.10 8:479.10>287.90(+) CE: -53V 461.95 461.95 S compound generating a fragmentation spectra that could be used in routine library Matrix Beef Matrix Milk Matrix Egg 461.95 H C N NH 9:479.10>274.95(+) CE: -44V of the molecule. Typically more than 10 precursor- 0 20 40 60 80 100 120 140 160 180 m/z 3 searching and compound verification using reference library match scores. 10:479.10>370.95(+) CE: -31V fragment ion transitions were monitored for each 154.00 156.05 154.00 274.95 8.49e6 11:479.10>285.85(+) CE: -56V veterinary drug. 274.95 154.00 274.95 Sulfamerazine NH2 98.05 98.05 260.05 260.05 98.05 260.05 100pg/uL 92.05 303.05 108.05 172.05 2. Materials and Methods 303.05 370.95 303.05 370.95 370.95 Matrix Beef 65.00 110.05 Samples of beef, egg, honey, milk and salmon were extracted and spiked in the 6.50 6.75 7.00 7.25 7.50 min MRM Spectrum Mode 0 100 200 300 400 m/z 0 100 200 300 400 m/z 0 100 200 300 400 m/z 11 MRM’s acquired for calibration range 0.001 – 0.1 mg/kg. Repeatability was assessed at low and high Figure 1. MRM Spectrum mode was used to acquire a high number of fragment ions for each 80.05 sulfamerazine in beef. Figure 3. Library searchable MRM spectrum data for chlortetracycline in different matrices spiked at 38.95 66.05 93.10 199.10 veterinary drug target. For chlortetracycline, 11 precursor-fragment ion transitions were concentrations. Samples were measured using a Nexera UHPLC and the LCMS-8060 10pg/uL. 1:265.10>156.05 (+) CE: -17V acquired using optimized collision energies. By acquiring a high number of fragment ion 0 20 40 60 80 100 120 140 160 180 m/z triple quadrupole detector (Table 1). Over 200 veterinary drugs were targeted, with more Compound name Virginiamycin S1 2:265.10>92.05 (+) CE: -30V transitions, each target veterinary drug had a corresponding fragmentation spectra which could 3:265.10>172.05 (+) CE: -15V Virginiamycin S1 MRM Spectrum Precursor 824.35 [M+H]+ 4.5 Sulfamerazine than 2,000 MRM transitions in both ESI +/- during the 12minute gradient. OH 4:265.10>108.05 (+) CE: -26V be used in routine library searching and compound verification using reference library match 205.05 m/z 205.05 Formula C43H49N7O10 4 Calibration curve 1-100pg/uL + 5:265.10>65.00 (+) CE: -11V [Accurate mass 205.06077] NH2 CAS 23152-29-6 H C scores. (Chlortetratcycline is a tetracycline class of antimicrobial. According to the Sixth ESVAC N O 3 3.5 Matrix Beef Formula C10H9N2O3 (+4H) 6:265.10>110.05 (+) CE: -22V Liquid chromatography report published in 2016, of the overall sales of antimicrobials in the 29 EU countries in 2014, O 3 H3C 7:265.10>80.05 (+) CE: -15V 177.00 OH N H UHPLC Nexera LC system the largest amounts, expressed as a proportion of mg/PCU, were accounted for by tetracyclines 290.05 HN 2.5 8:265.10>38.95 (+) CE: -14V 162.10 481.05 O Analytical column Restek Biphenyl (100 x 2.1, 2.7µm) 663.20 2 9:265.10>199.10 (+) CE: -21V (33.4 %), penicillins (25.5%) and sulfonamides (11.0 %). Chlortetracycline was selected as a 259.10 453.10 566.15 NH OH C N Column temperature / Flow rate 40oC ; 0.4mL/minute N O 3 H 1.5 10:265.10>93.10 (+) CE: -30V representative target). 0 y = 0.0419x + 0.0085 Solvent A 0.1% formic acid 0.5mM ammonium formate solution H3C 11:265.10>66.05 (+) CE: -24V 259.10 453.10 566.15 O 1 R² = 0.9997 663.20 O Solvent B 0.1% formic acid in methanol 134.00 481.05 H3C O 290.05 OH H 0.5 Binary Gradient Time (mins) %B Time (mins) %B 177.00 HN N m/z 154.00 m/z 274.95 m/z 444.00 m/z 461.95 m/z 290.05 N 0 [Accurate mass 462.09557] NH O O 0.00 2 14.60 2 [Accurate mass 154.05042] [Accurate mass 275.04749] [Accurate mass 444.08501] [Accurate mass 290.11353] N O 0 20 40 60 80 100 5.60 5.70 min Formula C22H21NO8Cl + 12.50 100 17.50 Stop Formula C7H8NO3 (+4H) Formula C15H12O3Cl (+4H) Formula C22H19NO7Cl (+2H) Formula C14H16N3O4 (+4H) O CH Concentration (pg/uL) + + OH O OH O O H3C O H OH O OH2 O OH 14.50 100 OH O OH O O OH + 205.05 C O OH + Virginiamycin S1 Library MRM Spectrum C Figure 5. Library searchable MRM spectrum data for sulfamerazine over three orders of magnitude Mass spectrometry OH OH 150 200 250 300 350 400 450 500 550 600 650 m/z (1pfg/uL to 100pg/uL). Linear calibration curves were generated for all compounds with r2 typically CH HO CH N Cl 3 Cl 3 N HO CH H3C CH3 Mass spectrometer Shimadzu LCMS-8060 H3C CH3 Cl 3 N Virginiamycin S1 Virginiamycin S1 Virginiamycin S1 greater than 0.9996. Sulfamerazine was selected as a representative target. H3C CH3 Pause time/dwell time 1 msec/3 msec 444.00 205.05 Similarity Score 99 205.05 Similarity Score 99 205.05 Similarity Score 100 Polarity switching time Pos/neg switching time set to 5 msec Matrix Salmon Matrix Salmon Matrix Salmon m/z 303.05 Scope 218 drugs in positive ion mode (including internal standards) Injection1 Injection 5 Injection 10 [Accurate mass 303.04241] 11 drugs in negative ion mode m/z 98.05 Formula C16H12O4Cl +(4H) 177.00 177.00 461.95 177.00 4. Conclusions Structure Analytics (in house development tool) [Accurate mass 98.06059] OH O OH 162.10 290.05 162.10 162.10 290.05 566.15 290.05 Source temperatures (interface; heat block; DL) 350oC; 300oC; 150oC Formula C5H8NO (+4H) m/z 260.05 566.15 134.00 566.15 [Accurate mass 260.02402] 481.05 663.20 481.05 663.20 481.05 663.20 H C Gas flows (nebulising; heating; drying) 3L/min; 10 L/min; 10L/min 3 + + 259.10 453.10 259.10 453.10 259.10 453.10 • To reduce false negative and false positive reporting a higher number of MRM transitions were OH 154.00 Formula C14H9O3Cl• (+4H) CH2 N O OH Cl HO CH3 used for each veterinary drug target to increase the level of confidence in compound H3C CH3 200 300 400 500 600 m/z 200 300 400 500 600 m/z 200 300 400 500 600 m/z Table 1.
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