Mass Spectrometry Imaging of Small Molecules: Methods and Protocols PDF
Preview Mass Spectrometry Imaging of Small Molecules: Methods and Protocols
Methods in Molecular Biology 2437 Young-Jin Lee Editor Mass Spectrometry Imaging of Small Molecules Methods and Protocols M M B ETHODS IN OLECULAR IO LO GY SeriesEditor JohnM.Walker School of Lifeand MedicalSciences University ofHertfordshire Hatfield, Hertfordshire, UK Forfurther volumes: http://www.springer.com/series/7651 For over 35 years, biological scientists have come to rely on the research protocols and methodologiesinthecriticallyacclaimedMethodsinMolecularBiologyseries.Theserieswas thefirsttointroducethestep-by-stepprotocolsapproachthathasbecomethestandardinall biomedicalprotocolpublishing.Eachprotocolisprovidedinreadily-reproduciblestep-by- step fashion, opening with an introductory overview, a list of the materials and reagents neededtocompletetheexperiment,andfollowedbyadetailedprocedurethatissupported with a helpful notes section offering tips and tricks of the trade as well as troubleshooting advice. These hallmark features were introduced by series editor Dr. John Walker and constitutethekeyingredientineachandeveryvolumeoftheMethodsinMolecularBiology series. Tested and trusted, comprehensive and reliable, all protocols from the series are indexedinPubMed. Mass Spectrometry Imaging of Small Molecules Methods and Protocols Edited by Young-Jin Lee Department of Chemistry, Iowa State University, Ames, IA, USA Editor Young-JinLee DepartmentofChemistry IowaStateUniversity Ames,IA,USA ISSN1064-3745 ISSN1940-6029 (electronic) MethodsinMolecularBiology ISBN978-1-0716-2029-8 ISBN978-1-0716-2030-4 (eBook) https://doi.org/10.1007/978-1-0716-2030-4 ©TheEditor(s)(ifapplicable)andTheAuthor(s),underexclusivelicensetoSpringerScience+BusinessMedia,LLC,part ofSpringerNature2022 Thisworkissubjecttocopyright.AllrightsaresolelyandexclusivelylicensedbythePublisher,whetherthewholeorpart of the material is concerned, specifically the rights of translation, reprinting, reuse of illustrations, recitation, broadcasting,reproductionon microfilmsorinanyotherphysicalway,andtransmissionorinformation storageand retrieval,electronicadaptation, computersoftware,orbysimilar ordissimilar methodologynow knownorhereafter developed. 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Preface The last decade has seen the evolution of mass spectrometry imaging (MSI) from an emerging technology to a matured and enabling technology that is commonly adopted for various biological and biomedical applications. Visualizing the localization of proteins wastheearlyfocusofthistechnology;however,themostpopularapplicationisnowonsmall moleculesincludingmetabolites,lipids,anddrugsthatwereonceregardedaschallengingin theearlydaysofthetechnique.AmethodbookinthissubjectwaspublishedintheMethods in Molecular Biology series six years ago in 2015, edited by Lin He. In the last few years, therehasbeenatremendousamountofnewdevelopmentinthefield.Thisnewbook,with the sametitle, is intended to bridge thegap byaddressingmany ofthe recent and exciting advancements. This book is organized into five themes that represent recent trends in MSI. Part I is comprised of innovative instrumental methods that allow for technological breakthrough. Localization of structural isomers can be determined by MS/MS imaging; however, some positiveionsdonotproduceusefulstructuralinformationinMS/MS.Chapter1describes howtoconvertpositiveionstonegativechargesthroughchargeinversionreactions,allow- ingforstructuralcharacterizationofthesechallengingions.MALDI-2,laser-inducedpost- ionization in matrix-assisted laser desorption ionization (MALDI), isa new technique that can dramatically enhance ion signals for many classes of small molecules. Chapter 2 illus- trateshowtoperformMALDI-2MSIinbothtop-illuminationandtransmissionmode.MSI oflivecellsisaninherentlychallengingtask.Chapter3tacklesthisissuewithanatmospheric pressureMSImethodusinglaserablationandatmosphericplasma,aswellassecondaryion mass spectrometry (SIMS) imaging of in-solution capped cells with single-layer graphene. Single cell metabolomics has become possible with high-spatial and high-mass resolution MSI.Forthispurpose,Chapter4combinesfiber-basedlaserablationelectrosprayionization (f-LAESI)with21TeslaFourierTransformIonCyclotronResonance(FTICR)-MS.Time- of-flight SIMS has the highest spatial resolution among MSI techniques but has had limitations in MS/MS capability until recently. Chapter 5 explains how to perform MS/MSofunknownionsbycombiningToF-SIMSandhybridSIMSforconsecutivetissue sections. MALDIisthemostpopularionizationmethodinMSI;however,theuseofanorganic matrixsignificantlylimitsitsapplicationtosmallmoleculesduetomassinterferenceorion suppression. Part II addresses a collection of alternative matrices, sometimes dubbed by variousacronyms,thathavebecomepopularinthelastdecadetoavoidtheissuesinherentto organic matrices. Chapters 6–9 describe how to synthesize or use alternative matrices for MSIincludingsiliconnanopostarrays(NAPA),metal-assistedLDI,nanostructureinitiator mass spectrometry (NIMS) with fluorinated gold nanoparticles, and nanoparticle-assisted laserdesorptionionization(Nano-PALDI),respectively. There are many challenges that hinder quantification with MS imaging. Part III encompasses new methods to address this issue of quantitative MSI. Chapter 10 details howtoperformnanosecondphotochemicalreaction(nsPCR)ontissueduringtheMALDI process, which showed dramatic improvement for the ion signals of amine-containing v vi Preface compounds and their quantifications. Chapter 11 overcomes common issues in MALDI quantificationusingamicrostructuredPDMSstamptopreciselycontrolthematrixdeposi- tion and the analyte extraction area. Extraction of small molecules followed by liquid chromatography(LC)-MSisbecomingpopular forquantitativeMSIasdescribedinChap- ters12and13usingdropletProbeMSandliquidmicrojunctionsurfacesampling(LMJSS), respectively. Part IV is composed of new types of applications in MSI. Chapter 14 adopts three different on-tissue chemical derivatization reactions to enhance metabolite coverage in MALDI-MSI. Chapter 15 extended the application of MSI for glycogen imaging using on-tissue enzyme digestion. Chapter 16 describes the multimodal imaging of free-floating brain sections using MSI and immunohistochemistry. In Chapter 17, silver ions are doped into nanospray desorption electrospray ionization (nano-DESI) to increase the specificity andsensitivityofdoublebondcontaininganalytes. DataanalysisisbecomingmoreandmoreimportantinMSI,particularlytounderstand the dataset beyond the visualization of a few targeted metabolites. As a sole chapter in Part V, Chapter 18 introduces multiple statistical methods for MSI including Multivariate Curve Resolution Alternating Square (MCR-ALS), Cluster Large Applications (CLARA) and Density-Based Spatial Clustering of Applications with Noise (DBSCAN) as unsuper- vised algorithms, Random Forest as a supervised machine learning, and Image Fusion to artificially enhance the spatial resolution of MSI by utilizing higher resolution optical images. This book does not cover all the recent developments in this subject, which is simply impossiblewithnewapproachesandmethodsbeingdevelopedandreportedeveryday,butI amproudthattheworkassembledhererepresentsmanyoftherecentkeydevelopments.I hopethisbookenablesnewcomerstograsptheoverallscopeofthetechnicaltrendandthe practical knowhow to adopt some of the methodology. This book will promote new ideas andencouragecurrentpractitionerstoexpandtheir researchintonewdirections. Lastly,Iwouldliketothankallthecontributorsofthisbook.Myappreciationisnotjust pertainingtothispublicationbutalsotheirdedicationtothecommunity.Iamgratefulfor this opportunity to work with many excellent scientists in the field and for being able to accomplishmyroleasacoordinator. Ames,IA,USA Young-JinLee Contents Preface ..................................................................... v Contributors................................................................. ix PART I INNOVATIONS IN INSTRUMENTAL METHODS FOR MASS SPECTROMETRY IMAGING 1 Gas-PhaseIon–IonReactionsforLipidIdentificationinBiological TissueSections ......................................................... 3 BooneM.Prentice 2 MALDI-2andt-MALDI-2MassSpectrometryImaging..................... 21 KlausDreisewerd,TanjaBien,andJensSoltwisch 3 AmbientMassSpectrometryImagingofSmallMolecules fromCellsandTissues................................................... 41 JaeYoungKim,HeejinLim,andDaeWonMoon 4 Single-CellMetabolomicswithRapidDetermination ofChemicalFormulasfromIsotopicFineStructures ........................ 61 LaithZ.Samarah,AkosVertes,andChristopherR.Anderton 5 TOF-SIMSImagingofBiologicalTissueSectionsandStructural DeterminationUsingTandemMS ........................................ 77 SebastiaanVanNuffelandAlainBrunelle PART II NEW TYPES OF LASER ABSORPTION METHODS IN MASS SPECTROMETRY IMAGING 6 MassSpectrometryImagingofBiologicalTissuesbyLaserDesorption IonizationfromSiliconNanopostArrays................................... 89 LaithZ.SamarahandAkosVertes 7 Metal-AssistedLaserDesorptionIonizationImagingMassSpectrometry ...... 99 Fre´de´ricFournelleandPierreChaurand 8 MassSpectrometryImagingofMetabolitesbyNanostructureInitiator MassSpectrometrywithFluorinatedGoldNanoparticles .................... 117 AmeliaPalermo 9 ImagingofPlantHormoneswithNanoparticle-AssistedLaser Desorption/IonizationMassSpectrometry ................................ 127 ShuTairaandKatsuhiroShiono PART III QUANTITATIVE MASS SPECTROMETRY IMAGING 10 NanosecondPhotochemicalReaction(nsPCR)forEnhancedMass SpectrometricIdentification,Quantification,andVisualization ofMetabolitesandNeuropeptides ........................................ 143 GongyuLi,YuanLiu,andLingjunLi vii viii Contents 11 ExtractionandUpconcentrationofAdsorbatesfromPreciselyDefinedArea forQuantitativeMALDIMassSpectrometryImaging....................... 159 SanghwanParkandChangYoungLee 12 DevelopmentandApplicationofDropletProbeMassSpectrometry forExaminingBiodistributionofTherapeutics ............................. 171 BingmingChen,MarissaVavrek,MarkT.Cancilla, andVilmosKertesz 13 QuantitativeMassSpectrometryImagingwithLiquidMicrojunction SurfaceSampling ....................................................... 181 QianWuandHongmeiLu PART IV NEW TYPES OF APPLICATIONS 14 EnhancingMetaboliteCoverageforMatrix-AssistedLaser Desorption/IonizationMassSpectrometryImagingThrough MultipleOn-TissueChemicalDerivatizations .............................. 197 KellyC.O’Neill,MariaEmiliaDuen˜as,EvanLarson, TrevorT.Forsman,andYoung-JinLee 15 Matrix-AssistedLaserDesorption/IonizationMassSpectrometry ImagingofGlycogenInSitu............................................. 215 TaraR.HawkinsonandRamonC.Sun 16 MALDIMassSpectrometryImagingofLipidsonFree-FloatingBrain SectionsandImmunohistochemicallyColocalizedMarkers ofNeurodegeneration................................................... 229 Sˇteˇpa´nStrnad,VeronikaStrnadova´,DavidSy´kora,JosefCvacˇka, LenkaMaletı´nska´,andVladimı´rVrkoslav 17 Silver-DopedNano-DESIMSIforIncreasedSpecificity andSensitivityofAlkenes................................................ 241 JohanLilljaandIngelaLanekoff PART V INNOVATIONS IN DATA ANALYSIS 18 ExtractMetabolomicInformationfromMassSpectrometryImages UsingAdvancedDataAnalysis............................................ 253 XiangTian,ZhuZou,andZhiboYang Index ...................................................................... 273 Contributors CHRISTOPHERR.ANDERTON • EnvironmentalMolecularSciencesLaboratoryandBiological SciencesDivision,PacificNorthwestNationalLaboratory,Richland,WA,USA TANJABIEN • InstituteofHygiene,UniversityofMu¨nster,Mu¨nster,Germany ALAINBRUNELLE • SorbonneUniversite´,CNRS,Laboratoired’Arche´ologieMole´culaireet Structurale,LAMS,Paris,France MARKT.CANCILLA • DepartmentofPreclinicalDevelopment,Merck&Co.,Inc., Kenilworth,NJ,USA PIERRECHAURAND • DepartmentofChemistry,Universite´deMontre´al,Montreal,QC, Canada BINGMINGCHEN • DepartmentofPreclinicalDevelopment,Merck&Co.,Inc.,Kenilworth, NJ,USA JOSEF CVACˇKA • InstituteofOrganicChemistryandBiochemistryoftheCzechAcademyof Sciences,Prague,CzechRepublic KLAUSDREISEWERD • InstituteofHygiene,UniversityofMu¨nster,Mu¨nster,Germany MARIAEMILIADUEN˜AS • DepartmentofChemistry,IowaStateUniversity,Ames,IA,USA TREVORT.FORSMAN • DepartmentofChemistry,IowaStateUniversity,Ames,IA,USA FRE´DE´RIC FOURNELLE • DepartmentofChemistry,Universite´deMontre´al,Montreal,QC, Canada TARA R.HAWKINSON • DepartmentofNeuroscience,UniversityofKentuckyCollegeof Medicine,Lexington,KY,USA VILMOSKERTESZ • BioanalyticalMassSpectrometryGroup,BiosciencesDivision,OakRidge NationalLaboratory,OakRidge,TN,USA JAEYOUNGKIM • SchoolofElectronicandElectricalEngineering,CollegeofITEngineering, KyungpookNationalUniversity,Daegu,RepublicofKorea INGELALANEKOFF • DepartmentofChemistry–BMC,UppsalaUniversity,Uppsala,Sweden EVANLARSON • DepartmentofChemistry,IowaStateUniversity,Ames,IA,USA CHANGYOUNGLEE • SchoolofEnergyandChemicalEngineering,UlsanNationalInstitute ofScienceandTechnology(UNIST),Ulsan,SouthKorea YOUNG-JINLEE • DepartmentofChemistry,IowaStateUniversity,Ames,IA,USA GONGYU LI • SchoolofPharmacy,UniversityofWisconsin-Madison,Madison,WI,USA; ResearchCenter forAnalyticalScienceandTianjinKeyLaboratoryofBiosensingand MolecularRecognition,CollegeofChemistry,NankaiUniversity,Tianjin,China LINGJUNLI • SchoolofPharmacy,UniversityofWisconsin-Madison,Madison,WI,USA JOHANLILLJA • DepartmentofChemistry–BMC,UppsalaUniversity,Uppsala,Sweden HEEJINLIM • DepartmentofNewBiology,DaeguGyeongbukInstituteofScienceand Technology(DGIST),Daegu,RepublicofKorea YUANLIU • SchoolofPharmacy,UniversityofWisconsin-Madison,Madison,WI,USA HONGMEILU • CollegeofChemistryandChemicalEngineering,CentralSouthUniversity, Changsha,Hunan,P.R.China LENKAMALETI´NSKA´ • InstituteofOrganicChemistryandBiochemistryoftheCzechAcademy ofSciences,Prague,CzechRepublic ix
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