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Inorganic Chemical Biology Inorganic Chemical Biology Principles, Techniques and Applications Edited by GILLES GASSER Department of Chemistry, University of Zurich, Switzerland Thiseditionfirstpublished2014 ©2014JohnWiley&Sons,Ltd Registeredoffice JohnWiley&SonsLtd,TheAtrium,SouthernGate,Chichester,WestSussex,PO198SQ,UnitedKingdom Fordetailsofourglobaleditorialoffices,forcustomerservicesandforinformationabouthowtoapplyforpermissiontoreuse thecopyrightmaterialinthisbookpleaseseeourwebsiteatwww.wiley.com. TherightoftheauthortobeidentifiedastheauthorofthisworkhasbeenassertedinaccordancewiththeCopyright,Designs andPatentsAct1988. Allrightsreserved.Nopartofthispublicationmaybereproduced,storedinaretrievalsystem,ortransmitted,inanyformorby anymeans,electronic,mechanical,photocopying,recordingorotherwise,exceptaspermittedbytheUKCopyright,Designs andPatentsAct1988,withoutthepriorpermissionofthepublisher. 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Nowarrantymaybecreatedorextendedbyanypromotionalstatementsforthiswork.Neitherthepublishernortheauthorshall beliableforanydamagesarisingherefrom. LibraryofCongressCataloging-in-PublicationData Inorganicchemicalbiology:principles,techniquesandapplications/editor,GillesGasser. p.;cm. Includesbibliographicalreferencesandindex. ISBN978-1-118-51002-5(cloth) I. Gasser,Gilles,editorofcompilation. [DNLM:1.BiochemicalPhenomena.2.Metals–chemistry.3.MacromolecularSubstances–chemistry.QU130.2] QP606.D46 ′ 572.43–dc23 2013049090 AcataloguerecordforthisbookisavailablefromtheBritishLibrary. ISBN:9781118510025 Typesetin10/12ptTimesLTStdbyLaserwordsPrivateLimited,Chennai,India 1 2014 Contents AbouttheEditor xiii ListofContributors xv Preface xix Acknowledgements xxi 1. NewApplicationsofImmobilizedMetalIonAffinityChromatography inChemicalBiology 1 RachelCodd,JiesiGu,NajwaEjjeandTulipLifa 1.1 Introduction 1 1.2 PrinciplesandTraditionalUse 2 1.3 ABriefHistory 4 1.4 NewApplication1:Non-proteinBasedLowMolecularWeight Compounds 5 1.4.1 Siderophores 6 1.4.2 AnticancerAgent:TrichostatinA 10 1.4.3 AnticancerAgent:Bleomycin 12 1.4.4 Anti-infectiveAgents 13 1.4.5 OtherAgents 14 1.4.6 SelectingaViableTarget 15 1.5 NewApplication2:Multi-dimensionalImmobilizedMetalIon AffinityChromatography 17 1.6 NewApplication3:Metabolomics 20 1.7 NewApplication4:Coordinate-bondDependentSolid-phase OrganicSynthesis 20 1.8 GreenChemistryTechnology 21 1.9 Conclusion 23 Acknowledgments 24 References 24 2. MetalComplexesasToolsforStructuralBiology 37 MichaelD.Lee,BimGrahamandJamesD.Swarbrick 2.1 StructuralBiologicalStudiesandtheMajorTechniquesEmployed 37 2.2 WhatdoMetalComplexeshavetoOffertheFieldofStructural Biology? 38 2.3 MetalComplexesforPhasinginX-rayCrystallography 39 vi Contents 2.4 MetalComplexesforDerivationofStructuralRestraintsvia ParamagneticNMRSpectroscopy 41 2.4.1 ParamagneticRelaxationEnhancement(PRE) 42 2.4.2 ResidualDipolarCoupling(RDC) 43 2.4.3 Pseudo-ContactShifts(PCS) 43 2.4.4 StrategiesforIntroducingLanthanideIonsinto Bio-Macromolecules 44 2.5 MetalComplexesasSpinLabelsforDistanceMeasurements viaEPRSpectroscopy 53 2.6 MetalComplexesasDonorsforDistanceMeasurementsvia LuminescenceResonanceEnergyTransfer(LRET) 54 2.7 ConcludingStatementsandFutureOutlook 56 References 56 3. AAS,XRF,andMSMethodsinChemicalBiologyofMetalComplexes 63 IngoOtt,ChristopheBiotandChristianHartinger 3.1 Introduction 63 3.2 AtomicAbsorptionSpectroscopy(AAS) 64 3.2.1 FundamentalsandBasicPrinciplesofAAS 64 3.2.2 InstrumentalandTechnicalAspectsofAAS 65 3.2.3 MethodDevelopmentandAspectsofPracticalApplication 67 3.2.4 SelectedApplicationExamples 69 3.3 TotalReflectionX-RayFluorescenceSpectroscopy(TXRF) 72 3.3.1 FundamentalsandBasicPrinciplesofTXRF 72 3.3.2 Instrumental/MethodicalAspectsofTXRFandApplications 73 3.4 SubcellularX-rayFluorescenceImagingofaRutheniumAnalogueof theMalariaDrugCandidateFerroquineUsingSynchrotronRadiation 74 3.4.1 ApplicationofX-rayFluorescenceinDrugDevelopment UsingFerroquineasanExample 75 3.5 MassSpectrometricMethodsinInorganicChemicalBiology 80 3.5.1 MassSpectrometryandInorganicChemicalBiology: SelectedApplications 83 3.6 Conclusions 90 Acknowledgements 90 References 90 4. MetalComplexesforCellandOrganismImaging 99 KennethYinZhangandKennethKam-WingLo 4.1 Introduction 99 4.2 PhotophysicalProperties 100 4.2.1 FluorescenceandPhosphorescence 100 4.2.2 Two-photonAbsorption 101 4.2.3 UpconversionLuminescence 102 Contents vii 4.3 DetectionofLuminescentMetalComplexesinanIntracellular Environment 104 4.3.1 ConfocalLaser-scanningMicroscopy 104 4.3.2 FluorescenceLifetimeImagingMicroscopy 105 4.3.3 FlowCytometry 106 4.4 CellandOrganismImaging 107 4.4.1 FactorsAffectingCellularUptake 107 4.4.2 OrganelleImaging 116 4.4.3 Two-photonandUpconversionEmissionImaging forCellsandOrganisms 133 4.4.4 IntracellularSensingandLabeling 136 4.5 Conclusion 143 Acknowledgements 143 References 143 5. CellularImagingwithMetalCarbonylComplexes 149 LucaQuaroniandFabioZobi 5.1 Introduction 149 5.2 VibrationalSpectroscopyofMetalCarbonylComplexes 151 5.3 MicroscopyandImagingofCellularSystems 154 5.3.1 TechniquesofVibrationalMicroscopy 155 5.4 InfraredMicroscopy 155 5.4.1 ConcentrationMeasurementswithIRSpectroscopyand Spectromicroscopy 157 5.4.2 WaterAbsorption 158 5.4.3 MetalCarbonylsasIRProbesforCellularImaging 158 5.4.4 InVivoUptakeandReactivityofMetalCarbonylComplexes 162 5.5 RamanMicroscopy 167 5.5.1 ConcentrationMeasurementswithRamanSpectroscopyand Spectromicroscopy 169 5.5.2 MetalCarbonylsasRamanProbesforCellularImaging 169 5.6 Near-fieldTechniques 171 5.6.1 ConcentrationMeasurementswithNear-fieldTechniques 172 5.6.2 High-resolutionMeasurementofIntracellularMetal–Carbonyl AccumulationbyPhotothermalInducedResonance 173 5.7 ComparisonofTechniques 175 5.8 ConclusionsandOutlook 176 Acknowledgements 177 References 178 6. ProbingDNAUsingMetalComplexes 183 LionelMarcélis,WillemVanderlindenandAndréeKirsch-DeMesmaeker 6.1 GeneralIntroduction 183 6.2 PhotophysicsofRu(II)Complexes 184 6.2.1 TheFirstRu(II)ComplexStudiedintheLiterature: [Ru(bpy) ]2+ 184 3 viii Contents 6.2.2 HomolepticComplexes 186 6.2.3 HeterolepticComplexes 186 6.2.4 PhotoinducedElectronTransfer(PET)andEnergy TransferProcesses 188 6.3 State-of-the-artontheInteractionsofMononuclearRu(II)Complexes withSimpleDouble-strandedDNA 190 6.3.1 StudiesonSimpleDouble-strandedDNAs 191 6.3.2 InfluenceofDNAontheEmissionProperties 193 6.4 StructuralDiversityoftheGeneticMaterial 194 6.4.1 MechanicalPropertiesofDNA 195 6.4.2 DNATopology 195 6.4.3 SMFStudywith[Ru(phen) (PHEHAT)]2+and 2 [Ru(TAP) (PHEHAT)]2+ 198 2 6.5 UnusualInteractionofDinuclearRu(II)ComplexeswithDifferent DNATypes 200 6.5.1 ReversibleInteractionof[{(Ru(phen) } HAT]4+with 2 2 DenaturedDNA 201 6.5.2 TargetingG-quadruplexeswithPhotoreactive [{Ru(TAP) } TPAC]4+ 204 2 2 6.5.3 ThreadingIntercalation 205 6.6 Conclusions 207 Acknowledgement 208 References 208 7. VisualizationofProteinsandCellsUsingDithiol-reactiveMetal Complexes 215 DaniellePark,IvanHoShon,MinhHua,VivienM.ChenandPhilipJ.Hogg 7.1 TheChemistryofAs(III)andSb(III) 215 7.2 CysteineDithiolsinProteinFunction 217 7.3 VisualizationofDithiolsinIsolatedProteinswithAs(III) 218 7.4 VisualizationofDithiolsontheMammalianCellSurfacewithAs(III) 218 7.5 VisualizationofDithiolsinIntracellularProteinswithAs(III) 219 7.6 VisualizationofTetracysteine-taggedRecombinantProteinsinCells withAs(III) 219 7.7 VisualizationofCellDeathintheMousewithOptically LabelledAs(III) 220 7.7.1 CellDeathinHealthandDisease 220 7.7.2 CellDeathImagingAgents 222 7.7.3 VisualizationofCellDeathinMouseTumours,Brainand ThrombiwithOpticallyLabelledAs(III) 223 7.8 VisualizationofCellDeathinMouseTumourswithRadio-labelled As(III) 225 7.9 SummaryandPerspectives 227 References 227