Chemical analysis of non-antimicrobial veterinary drug residues in food

633 Pages·2016·8.721 MB·English

by  Kay, Jack F., MacNeil, James D., Wang, Jian

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ChemicalAnalysisofNon-antimicrobial
VeterinaryDrugResiduesinFood
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WILEYSERIESONMASSSPECTROMETRY
SeriesEditors
DominicM.Desiderio
DepartmentsofNeurologyandBiochemistry
UniversityofTennesseeHealthScienceCenter
JosephA.Loo
DepartmentofChemistryandBiochemistryUCLA
FoundingEditors
NicoM.M.Nibbering(1938–2014)
DominicM.Desiderio
Acompletelistofthetitlesinthisseriesappearsattheendofthisvolume.
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Chemical Analysis of Non-antimicrobial
Veterinary Drug Residues in Food
EditedbyJackF.Kay,JamesD.MacNeil,andJianWang
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Copyright©2017byJohnWiley&Sons,Inc.Allrightsreserved
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LibraryofCongressCataloging-in-PublicationData
Names:Kay,JackF.,editor.|MacNeil,JamesD.,editor.|Wang,Jian,1964-
editor.
Title:Chemicalanalysisofnon-antimicrobialveterinarydrugresiduesin
food/editedbyJackF.Kay,JamesD.MacNeil,JianWang.
Description:Hoboken,NewJersey:JohnWiley&Sons,Inc.,[2017]|Includes
bibliographicalreferencesandindex.
Identifiers:LCCN2016033527|ISBN9781118695074(cloth)|ISBN9781119325901
(epub)
Subjects:LCSH:Veterinarydrugresidues.|Foodcontamination.
Classification:LCCRA1270.V47C44252017|DDC664/.07–dc23LCrecordavailableat
https://lccn.loc.gov/2016033527
Setin10/12pt,WarnockProbySPiGlobal,Chennai,India
PrintedintheUnitedStatesofAmerica
10 9 8 7 6 5 4 3 2 1
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ThisbookisdedicatedtothememoryofDr.JohnJ.O’RangersJr.,11June1936–20
January2013.
Johnwasinternationallywellknownandrespectedinthefieldofveterinarydrug
residuechemistryandinternationalregulations.BothDr.JamesMacNeilandDr.
JackKaywerehonoredtohaveknownandworkedwithhimovermanyyearsand
alsotocallhimafriend.Developinginternationalcooperationand
understandingwasacornerstoneofJohn’sviewoflifeandworkethic,regardless
ofthemorepoliticallyopinionatedviewsheldbysome.Manyinternational
developmentsinthisfieldandfriendshipsaretheresultoftheworkJohn
conductedbehindthescenestobreakdownbarriers.Hetrulywasoneofakind
andhispassingleavesusallimpoverished.
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vii
Contents
Preface xix
ListofContributors xxi
AbouttheEditors xxv
1 BasicConsiderationsfortheAnalystforVeterinaryDrug
ResidueAnalysisinAnimalTissues 1
JamesD.MacNeilandJackF.Kay
1.1 Introduction 1
1.2 Pharmacokinetics 1
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1.3 MetabolismandDistribution 3
1.4 ChoiceofAnalyticalMethod 5
1.5 ImportanceofRegulatoryLimits 7
1.5.1 DerivationoftheAcceptableDailyIntake 7
1.5.2 DerivationoftheAcuteReferenceDose 9
1.5.3 DerivationofMaximumResidueLimits 10
1.5.4 DerivationofTolerances 12
1.6 InternationalObligationsforRegulatoryAnalyticalLaboratories 13
1.6.1 LaboratoryAccreditation 13
1.6.2 ValidationofAnalyticalMethods 14
1.6.3 ConsistentUseofTerminology 15
1.6.4 SampleHandlingandRetention 16
1.6.5 ConfirmatoryAnalysis 17
1.6.6 QualityAssuranceMeasures 19
1.6.7 ProficiencyTesting 19
1.6.8 ReportingofResults 19
1.7 Conclusions 21
References 21
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viii Contents
2 EmergingTechniquesinSampleExtractionandRapid
Analysis 27
WendyC.Andersen,SherriB.Turnipseed,andJackJ.Lohne
2.1 Introduction 27
2.2 SampleExtraction 28
2.2.1 SolventExtractionandProteinPrecipitation 29
2.2.2 PhaseSeparationbySalt-InducedPartitioning 30
2.2.3 PhaseSeparationbyLow-TemperaturePartitioning 30
2.2.4 PhysicalSeparationbyultra-filtration 31
2.2.5 SampleExtractionwithGreenChemistryTechniques 32
2.2.5.1 PressurizedLiquidExtraction 32
2.2.5.2 RoomTemperatureIonicLiquids 32
2.2.5.3 Ultrasound-AssistedExtraction 33
2.2.5.4 Microwave-AssistedExtraction 34
2.3 ExtractClean-upwithSolid-PhaseSorbents 34
2.3.1 Solid-PhaseExtractionFormats 35
2.3.1.1 CartridgeSPE 35
2.3.1.2 OnlineCartridgeSPE 35
2.3.1.3 TurbulentFlowClean-up 35
2.3.1.4 DispersiveSPE 36
2.3.1.5 MatrixSolid-PhaseDispersion 37
(cid:2) 2.3.1.6 SupportedLiquidExtraction 38 (cid:2)
2.3.2 Solid-PhaseSorbentChemistry 38
2.3.2.1 SorbentsforSPEanddSPE 38
2.3.2.2 MolecularRecognitionBasedonMolecularlyImprinted
Polymers 39
2.3.2.3 MolecularRecognitionBasedonAptamers 40
2.3.2.4 RestrictedAccessMaterials 41
2.3.2.5 Nanomaterials 43
2.4 Micro-extractionTechniquesforSolventandSorbentExtraction 47
2.4.1 SolventMicro-extraction 47
2.4.1.1 SingleDropMicro-extraction 47
2.4.1.2 DispersiveLiquid–LiquidMicro-extraction 48
2.4.1.3 HollowFiberMicro-extraction 50
2.4.2 SorbentMicro-extraction 51
2.4.2.1 Solid-PhaseMicro-extraction 52
2.4.2.2 StirBarSorptiveExtraction 52
2.4.2.3 FabricPhaseSorptiveExtraction 53
2.5 EmergingTechniquesinLiquidChromatography 54
2.5.1 UltrahighPerformanceLiquidChromatography 54
2.5.2 Core–ShellColumns 54
2.5.3 HydrophilicInteractionLiquidChromatography 55
2.5.4 OtherEmergingLCTechniques 56
2.6 DirectMassSpectrometryAnalysisofSampleExtracts 57
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Contents ix
2.6.1 FlowInjectionMassSpectrometry 57
2.6.2 DirectDesorption/IonizationMassSpectrometry 58
2.6.2.1 APCI-BasedTechniques 59
2.6.2.2 ESI-BasedTechniques 63
2.6.3 DirectMSConsiderationsforRegulatoryAnalysis 65
2.7 IonMobilitySpectrometry 66
2.8 Conclusions 67
References 68
3 CapabilitiesandLimitationsofHigh-ResolutionMass
Spectrometry(HRMS):time-of-flightandOrbitrapTM 93
AntonKaufmannandPhilTeale
3.1 AvailableTechnology 93
3.1.1 TOF 94
3.1.2 OrbitrapTM 99
3.2 CapabilitiesandLimitationsoftheTechnologyasComparedto
LC-MS/MS(TandemQuadrupoleMassSpectrometer) 104
3.2.1 Selectivity 105
3.2.2 Quantification 108
3.2.3 Sensitivity 108
3.2.4 ValidationofHRMS-BasedMethods 110
(cid:2) 3.2.5 MethodDiagnosisTools 112 (cid:2)
3.3 AnalyticalMethodsforVeterinaryDrugResidues 112
3.3.1 InitialApplications(Non-antimicrobialVeterinaryDrugs) 112
3.3.2 MethodsLimitedtoaSingle-DrugGroup 113
3.3.3 MethodsCoveringMultiple-DrugGroups 114
3.3.4 MethodComponents 115
3.3.4.1 ExtractionandClean-up 115
3.3.4.2 Separation 117
3.3.5 ResidueTestingofAnabolicSteroidsandGrowthPromoters 119
3.4 DopingControl 121
3.4.1 GC-HRMS 121
3.4.2 AccurateMassLC-MSandLC-MS/MSinDopingControl 122
3.4.3 “DiluteandShoot”withAccurateMassLC-MS 123
3.5 AccurateMassMSinResearchandMetabolismStudies 124
3.6 DesignerDrugsandGenericDetectionStrategies 125
3.6.1 MetabolomicsinFood/ResidueAnalysis 127
3.7 TheFutureofAccurateMassSpectrometryinResidueAnalysis 129
References 131
4 Hormonesand𝛃-Agonists 141
LeendertA.vanGinkel,ToineBovee,MarcoH.Blokland,SaskiaS.Sterk,
NathalieG.E.Smits,JelkaPleadinandAnaVulic´
4.1 Introduction 141
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x Contents
4.2 AdvancesinClassicalAnalysisofExogenousSynthetic
Hormones 143
4.2.1 Multi-methods:Multi-residueMethods(MRMs)andMulti-class,
Multi-residueMethods(MCMRs) 143
4.2.2 AlternativesinSamplePreparationandClean-up 144
4.2.2.1 Generic 144
4.2.2.2 QuEChERS 144
4.2.2.3 MolecularlyImprintedPolymers(MIPs) 154
4.2.2.4 Hollow-FiberMicro-extractionsandSimilarTechniques 154
4.2.2.5 DiluteandShoot 155
4.2.3 AdvancesinSeparation 155
4.2.3.1 MiniaturizedSeparationTechniques 155
4.2.3.2 TurbulentFlowLC 156
4.2.3.3 IonMobilitySpectrometry 156
4.2.3.4 TechniquestoFacilitateIRMS:High-TemperatureLC,
Two-DimensionalChromatography,andOthers 156
4.2.4 AdvancesinDetection 157
4.2.4.1 Isotope-RatioMassSpectrometry(IRMS) 158
4.2.4.2 AmbientIonizationMassSpectrometry(AMS) 158
4.2.4.3 OtherTechniques 159
4.2.5 ClassicandNewAnalyticalMatrices 160
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4.2.6 ConclusionsonAnalysisofExogenousSyntheticHormones 161
4.3 Bio-BasedScreeningMethodsforSteroidHormones,β-Agonists,and
GrowthHormones 161
4.3.1 Estrogens 162
4.3.1.1 BindingAssaysforEstrogens 162
4.3.1.2 BioassaysforEstrogens 164
4.3.2 Androgens 166
4.3.2.1 BindingAssaysforAndrogens 166
4.3.2.2 BioassaysforAndrogens 168
4.3.3 MetabolicProfilingAssaytoDetectAbuseofEstrogensand
Androgens 171
4.3.4 ProgestagensandGlucocorticoids 171
4.3.4.1 BindingAssaysforProgestagensandGlucocorticoids 171
4.3.4.2 BioassaysforProgestagensandGlucocorticoids 172
4.3.5 Thyreostatics 173
4.3.6 β-Agonists 175
4.3.6.1 BindingAssaysforβ-Agonists 175
4.3.6.2 Bioassaysforβ-Agonists 176
4.3.7 GrowthHormones 177
4.3.7.1 RecombinantGrowthHormoneinCattle 177
4.3.7.2 GrowthHormoneinFish 178
4.3.7.3 GrowthHormoneinHorse 179
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Contents xi
4.3.8 ConclusionsandFutureDevelopmentsinBio-BasedScreening
Methods 179
4.4 NaturalHormones 180
4.4.1 NaturalCompoundsFormedDuringtheDigestionProcess 182
4.4.1.1 Prednisolone 182
4.4.2 Feed-RelatedCompounds 183
4.4.2.1 Thiouracil 183
4.4.2.2 Zeranol 184
4.4.3 TheNaturalHormones17β-Estradiol,17β-Testosterone,and
Progesterone 186
4.4.4 Nortestosterone 189
4.4.5 Boldenone 192
4.4.6 ProteinHormones 195
4.4.6.1 Insulin 195
4.4.6.2 Insulin-LikeGrowthFactor-1(IGF-1) 196
4.4.6.3 GrowthHormone 196
4.4.6.4 GrowthHormoneSecretagogues 197
4.4.7 FuturePerspectives(NaturalHormones) 199
4.5 ControlforSyntheticβ-Agonists:ScreeningandConfirmatory
Methods 199
4.5.1 BasicInformationonNatureandRegulatoryControls 199
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4.5.3 TherapeuticUseandAbuse 202
4.5.4 AbsorptionandElimination 203
4.5.5 BioavailabilityandResidues 203
4.5.6 DeterminationinBiologicalMaterials 204
4.5.6.1 SamplePreparationTechniques 204
4.5.6.2 ScreeningMethods 206
4.5.6.3 CurrentApproachesinAnalysisofβ-Agonists 206
4.5.7 FuturePerspective(β-Agonists) 208
References 210
5 AnalysisofAnthelminticandAnticoccidialDrugResiduesin
Animal-DerivedFoods 245
SarahTuck,AmbroseFureyandMartinDanaher
5.1 Introduction 245
5.2 ChemistryandModeofAction 246
5.2.1 Benzimidazoles 246
5.2.2 Imidazothiazoles 249
5.2.3 Tetrahydropyrimidines 249
5.2.4 Organophosphates 250
5.2.5 Flukicides 251
5.2.6 MacrocyclicLactones 251
5.2.7 OtherAnthelminticDrugs 252
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