Monoamine Oxidase: Methods and Protocols (Methods in Molecular Biology, 2558) PDF
Preview Monoamine Oxidase: Methods and Protocols (Methods in Molecular Biology, 2558)
Methods in Molecular Biology 2558 Claudia Binda Editor Monoamine Oxidase 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. Monoamine Oxidase Methods and Protocols Edited by Claudia Binda Department of Biology and Biotechnology, University of Pavia, Pavia, Italy Editor ClaudiaBinda DepartmentofBiologyandBiotechnology UniversityofPavia Pavia,Italy ISSN1064-3745 ISSN1940-6029 (electronic) MethodsinMolecularBiology ISBN978-1-0716-2642-9 ISBN978-1-0716-2643-6 (eBook) https://doi.org/10.1007/978-1-0716-2643-6 ©TheEditor(s)(ifapplicable)andTheAuthor(s),underexclusivelicensetoSpringerScience+BusinessMedia,LLC,part ofSpringerNature2023 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. Theuseofgeneraldescriptivenames,registerednames,trademarks,servicemarks,etc.inthispublicationdoesnotimply, evenintheabsenceofaspecificstatement,thatsuchnamesareexemptfromtherelevantprotectivelawsandregulations andthereforefreeforgeneraluse. Thepublisher,theauthors,andtheeditorsaresafetoassumethattheadviceandinformationinthisbookarebelievedto betrueandaccurateatthedateofpublication.Neitherthepublishernortheauthorsortheeditorsgiveawarranty, expressedorimplied,withrespecttothematerialcontainedhereinorforanyerrorsoromissionsthatmayhavebeen made.Thepublisherremainsneutralwithregardtojurisdictionalclaimsinpublishedmapsandinstitutionalaffiliations. ThisHumanaimprintispublishedbytheregisteredcompanySpringerScience+BusinessMedia,LLC,partofSpringer Nature. Theregisteredcompanyaddressis:1NewYorkPlaza,NewYork,NY10004,U.S.A. Preface This volume of the Methods in Molecular Biology series is specifically dedicated to mono- amine oxidases (MAOs). Among the different enzymes that catalyse the oxidation of a carbon-nitrogen bond in bioactive substrates, MAOs play a key role in the central nervous systembydeaminatingaromaticneurotransmitterssuchasdopamine,serotonin,andadren- aline. Moreover, xenobiotic compounds containing primary, secondary, or even tertiary amino groups that may be introduced pharmacologically or with one’s diet may be sub- strates for MAOs. Two isozymes, MAO A and MAO B, are expressed in mammals, which share 70% sequence identity and are both FAD-dependent enzymes anchored to the outer mitochondrialmembranethroughaC-terminalα-helix. MAOs have been known for almost a century, given that the identification of an oxidative deamination activity on tyramine was published in 1928. Since then, a huge number of studies on MAOs have been reported yielding more than 24,000 results by searching PubMed with the keyword “monoamine oxidase”. Other eukaryotic MAO enzymes were discovered such as fungal MAO N that is about 25% identical to MAO A/MAO B and is devoid of the membrane-binding domain, which makes this enzyme idealforbiocatalyticindustrialapplicationsthatinvolveanamineoxidationstep.Thisbook willfocusonmethodsusedtostudymammalian(mainlyhuman)MAOAandMAOBthat, for their central rolein neurotransmitter metabolism, are validateddrug targets for neuro- pathologies such as Parkinson’s and Alzheimer’s diseases and depression. In addition, the clinical context involving MAO A and MAO B is expanding as these enzymes are widely expressed not only in the brain but also in other organs such as heart, liver, placenta, and platelets. Their enzymatic activity, which generates high levels of hydrogen peroxide as secondary product, is supposed to contribute to the onset of ageing-related cardiovascular diseasesandcertaintypesofsolidtumoursbyincreasingcellularoxidativestress. MammalianMAOshavebeenextensivelystudied,bothbiochemicallywithinthespecific contextofflavoenzymes(coveringalsopurelymechanisticaspects)andpharmacologicallyin theframeworkoftheirinvolvementinneurologicaldiseases.Thisbookaimsatprovidinga picture of the main methods to study mammalian MAOs, ranging from cell biology to computationalchemistry.Acollectionof17chaptershavebeenwrittenbyscientistsactively involved in this field who contributed to developing most of the described methods. The first two chapters are focused on methods used to obtain pure samples of MAO A and MAO B, either from natural tissues (Chap. 1) or as recombinant proteins (Chap. 2). The former was routinely used before the advent of molecular biology techniques and may be stillusefulwhennativetissue-specificenzymesarerequired,thelatterentailedthedevelop- ment of a eukaryotic expression system in Pichia pastoris which was then extensively used also for other membrane proteins. Chapters 3, 4, 5, 6, 7, and 8 concern assays and techniques used to measure MAO enzymatic activity and perform inhibition studies. Chapter 9 is focused on protocol to crystallize human MAO B, which so far has been the most characterized form from a structural point of view. Chapters 10, 11, 12, 13, and 14 describedifferentmethodstoaddresscellularlocalizationandfunctionofMAOs,eitherin cell lines or in animal models. The last chapters (Chaps. 15, 16, and 17) are dedicated to computationalmethodsappliedtorationaldrugdesignapproachesthatareusedtodevelop newMAOinhibitors. v vi Preface Some of the methods described in this book were elaborated many years ago and they arestillused,insomecasesoptimizedwithtechnologicalimprovements.For thisreason,it may be difficult to learn and reproducibly apply these MAO-specific methods simply following the experimental section of articles. I hope this book may be useful for scientists interestedinstudyingMAOsandothersimilaramineoxidaseenzymes. Pavia,Italy ClaudiaBinda Contents Preface ..................................................................... v Contributors................................................................. ix 1 PurificationofMAOAandMAOBfromMammalianTissueSources......... 1 DaleE.Edmondson 2 PurificationofRecombinantEukaryoticMAOAandMAOB UtilizingthePichiapastorisExpressionSystem ...... ........ ....... ........ 11 DaleE.Edmondson 3 ThePeroxidase-CoupledAssaytoMeasureMAOEnzymaticActivity.......... 23 JoanaReisandClaudiaBinda 4 MeasurementofMAOEnzymaticActivitybySpectrophotometric DirectAssays ....... ....... ........ ....... ....... ........ ....... ........ 35 JoanaReisandClaudiaBinda 5 RadiochemicalAssayofMonoamineOxidaseActivity ... ..... ...... ....... .. 45 AndrewHolt 6 MAOVisibleSpectroscopyforLigandInteractions,RedoxChemistry, andKineticsofIrreversibleInhibition ....... ....... ........ ....... ........ 63 RonaR.Ramsay 7 ConventionalReceptorRadioligandBindingTechniquesApplied totheStudyofMonoamineOxidase ........ ....... ........ ....... ........ 75 AndrewHolt 8 AssayofMAOInhibitionbyChromatographicTechniques (HPLC/HPLC-MS) ....... ........ ...... ....... ....... .. ....... ........ 97 Toma´sHerraiz 9 CrystallizationofHumanMonoamineOxidaseB.... ........ ....... ........ 115 ClaudiaBinda,DaleE.Edmondson,andAndreaMattevi 10 DetectingMonoamineOxidaseAandBProteins:AWesternBlotting ProtocolandSomePracticalConsiderations ........ ........ ....... ........ 123 JenniferN.K.Nyarko,RyanM.Heistad,PaulR.Pennington, andDarrellD.Mousseau 11 An(Immuno)FluorescenceProtocolforMonitoringMonoamine OxidaseA/BProteinDistributionWithintheCell........... ....... ........ 143 TylerJ.Wenzel,JenniferN.K.Nyarko,RyanM.Heistad, PaulR.Pennington,ChrisP.Phenix,andDarrellD.Mousseau 12 ExpressionandFunctionofMAOAinCardiacCellsbyMeans ofAdenovirus-MediatedGeneTransfer...... ....... ........ ....... ........ 163 YohanSantin,AngeloParini,andJeanneMialet-Perez 13 InVitroandInVivoAssaysCharacterizingMAOAFunctioninCancers...... 171 BoyangJasonWuandJeanC.Shih vii viii Contents 14 InVivoStudyofMonoamineOxidasesUsingMultisiteIntracerebral Microdialysis ....... ....... ........ ....... ....... ........ ....... ........ 183 PhilippeDeDeurwaerde`re,NouhadSamb,HasnaElBoukhari, Re´miCorne,AbdeslamChagraoui,andGiuseppeDiGiovanni 15 InformedUseof3D-QSARfor theRationalDesignofCoumarin DerivativesasPotentandSelectiveMAOBInhibitors........ ....... ........ 197 NicolaGambacorta,MarcoCatto,LeonardoPisani, AngeloCarotti,andOrazioNicolotti 16 Hansch-TypeQSARModelsfor theRationalDesignofMAO Inhibitors:BasicPrinciplesandMethodology ....... ........ ....... ........ 207 LeonardoPisani,ModestodeCandia,MariagraziaRullo, andCosimoD.Altomare 17 ComputationalChemistryandMolecularModelingofReversible MAOInhibitors ... ........ ........ ....... ....... ........ ....... ........ 221 KemalYelekc¸iandSafiyeSag˘ Erdem Index ...................................................................... 253 Contributors COSIMOD.ALTOMARE • DepartmentofPharmacy-Pharmaceutical Sciences,Universityof Bari“AldoMoro”,Bari,Italy CLAUDIABINDA • DepartmentofBiologyandBiotechnology,UniversityofPavia,Pavia,Italy ANGELOCAROTTI • DepartmentofPharmacy-PharmaceuticalSciences,UniversityofBari “AldoMoro”,Bari,Italy MARCOCATTO • DepartmentofPharmacy-Pharmaceutical Sciences,UniversityofBari “AldoMoro”,Bari,Italy ABDESLAMCHAGRAOUI • NormandieUniversity,UNIROUEN,INSERM,U1239,CHU Rouen,NeuronalandNeuroendocrineDifferentiationandCommunicationLaboratory, InstituteforResearchandInnovationinBiomedicineofNormandy(IRIB),Rouen, France;DepartmentofMedicalBiochemistry,RouenUniversityHospital,Rouen,France RE´MICORNE • CentreNationaldelaRechercheScientifique(Unite´MixtedeRecherche 5287),BordeauxCedex,France MODESTODECANDIA • DepartmentofPharmacy-PharmaceuticalSciences,Universityof Bari“AldoMoro”,Bari,Italy PHILIPPEDEDEURWAERDE`RE • CentreNationaldelaRechercheScientifique(Unite´Mixtede Recherche5287),BordeauxCedex,France GIUSEPPE DIGIOVANNI • DepartmentofPhysiologyandBiochemistry,FacultyofMedicine andSurgery,UniversityofMalta,Msida,Malta;SchoolofBiosciences,CardiffUniversity, Cardiff,UK DALEE.EDMONDSON • DepartmentofBiochemistry,EmoryUniversity,Atlanta,GA,USA HASNAELBOUKHARI • CentreNationaldelaRechercheScientifique(Unite´Mixtede Recherche5287),BordeauxCedex,France SAFIYESAG˘ ERDEM • DepartmentofChemistry,FacultyofArtsandSciences,Marmara University,Istanbul,Turkey NICOLA GAMBACORTA • DepartmentofPharmacy-PharmaceuticalSciences,Universityof Bari“AldoMoro”,Bari,Italy RYANM.HEISTAD • DepartmentofPsychiatry,UniversityofSaskatchewan,Saskatoon,SK, Canada TOMA´SHERRAIZ • InstitutodeCienciayTecnologı´adeAlimentosyNutrici(cid:1)on(ICTAN), SpanishNationalResearchCouncil(CSIC),Madrid,Spain ANDREWHOLT • NeurochemicalResearchUnit,DepartmentofPsychiatry,Facultyof MedicineandDentistry,UniversityofAlberta,Edmonton,AB,Canada ANDREA MATTEVI • DepartmentofBiologyandBiotechnology,UniversityofPavia,Pavia, Italy JEANNEMIALET-PEREZ • InstituteofMetabolicandCardiovascularDiseases(I2MC), INSERM,Universite´deToulouse,Toulouse,France DARRELLD.MOUSSEAU • DepartmentofPsychiatry,UniversityofSaskatchewan,Saskatoon, SK,Canada ORAZIONICOLOTTI • DepartmentofPharmacy-PharmaceuticalSciences,UniversityofBari “AldoMoro”,Bari,Italy JENNIFERN.K.NYARKO • DepartmentofPsychiatry,UniversityofSaskatchewan,Saskatoon, SK,Canada ix
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