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Methods in Molecular Biology 2622 Gerard G.M. D'Souza Hongwei Zhang Editors Liposomes Methods and Protocols Third Edition 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. Liposomes Methods and Protocols Third Edition Edited by ' Gerard G. M. D Souza and Hongwei Zhang School of Pharmacy, MCPHS University, Boston, MA, USA Editors GerardG.M.D'Souza HongweiZhang SchoolofPharmacy SchoolofPharmacy MCPHSUniversity MCPHSUniversity Boston,MA,USA Boston,MA,USA ISSN1064-3745 ISSN1940-6029 (electronic) MethodsinMolecularBiology ISBN978-1-0716-2953-6 ISBN978-1-0716-2954-3 (eBook) https://doi.org/10.1007/978-1-0716-2954-3 ©TheEditor(s)(ifapplicable)andTheAuthor(s),underexclusivelicensetoSpringerScience+BusinessMedia,LLC,part ofSpringerNature2017,2023 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 The first edition of MiMB Liposomes Methods and Protocols was a two-volume edition that compiled a diverse array of protocols for pharmaceutical nanocarriers and biological mem- branemodels.Thesecondeditionontheotherhandemergedasasingle-volumecollection of basic protocols that was intended to serve as a complimentary everyday companion for scientists at all levels interested in using liposomes for drug delivery purposes. The continued popularity of MiMB Liposomes Methods and Protocols led to this third edition being developed. In this edition, we have sought to continue with the theme of ensuring thatfundamentalprotocolsfor thepreparationandcharacterizationofliposomesaremain- tained in a single convenient volume and ensuring that tried and tested protocols remain accessible to established and new investigators alike. The focus remains on entry-level protocols for the preparation of liposomes, physicochemical characterization of liposomes, lipid analysis, drug encapsulation, surface modification, stimuli response as well as cellular interaction, and biodistribution. Also essential to the continued health of the field of liposomology is an up-to-date history of its evolution. To this end, Chapter 1 from the second edition has been revised. The new version titled “From Olive Oil Emulsions to COVID-19 Vaccines: Liposomes Came First” is highly recommended as required reading for anyone interested in liposomology. We are extremely grateful to all the contributors to this edition and to Prof. John Walker the MiMB series editor for his guidance in the preparation of this edition. It is our hope that this volume will continue to serve as a convenient reference for graduate students, postdoctoral researchers, as well as established investigators utilizing lipid-based systems in the fields of cell and molecular biology, drug delivery,andphysicalchemistry. Boston,MA,USA GerardG.M.D'Souza HongweiZhang v Contents Preface ..................................................................... v Contributors................................................................. ix 1 FromOliveOilEmulsionstoCOVID-19Vaccines:Liposomes CameFirst ......... ....... ........ ....... ....... ........ ....... ........ 1 VolkmarWeissig 2 PreparationofDRVLiposomes...... ....... ....... ........ ....... ........ 21 SophiaG.Antimisiaris 3 PreparationofSmallUnilamellarVesicleLiposomesUsingDetergent DialysisMethod .... ....... ... ..... ...... ....... ...... ... ....... ........ 49 QingyueZhongandHongweiZhang 4 Thin-FilmHydrationFollowedbyExtrusionMethod forLiposomePreparation........... ....... ....... ........ ....... ........ 57 HongweiZhang 5 EthanolInjectionMethodforLiposomePreparation......... ....... ........ 65 GuangshengDuandXunSun 6 PreparationofGiantVesicleswithMixedSingle-Tailed andDouble-TailedLipids......... .. ...... .... .... ........ ....... ........ 71 LaurenA.LoweandAnnaWang 7 ScalableLiposomeSynthesisbyHighAspectRatioMicrofluidic FlowFocusing...... ....... ........ ....... ....... ........ ....... ........ 87 JungYeonHan,ZhuChen,andDonL.Devoe 8 PreparationofDoxorubicinLiposomesbyRemote LoadingMethod.... ....... ........ ...... ....... ......... ....... ........ 95 JianChen 9 MagneticThermosensitiveLiposomesLoadedwithDoxorubicin..... ........ 103 MohamadAlawak,AliceAbuDayyih,IbrahimAwak, BerndGutberlet,KonradEngelhardt,andUdoBakowsky 10 PreparationandPhysicalCharacterizationofDNABinding CationicLiposomes........ ........ ....... ....... ........ ....... ........ 121 VaibhavSaxena 11 TunablepHSensitiveLipoplexes .... ....... .... ... ... ..... ....... ........ 127 He´le`neDhotel,MichelBessodes,andNathalieMignet 12 SolidLipidNanoparticlesforDrugDelivery ........ ........ ....... ........ 139 Wei-ChungLuoandXiulingLu 13 StableDiscoidalBicelles:Formulation,Characterization, andFunctions...... ....... ........ ....... ....... ........ ....... ........ 147 YingLiu,YanXia,ArminTahmasbiRad, WafaAresh,JustinM.Fang,andMu-PingNieh vii viii Contents 14 ThePost-insertionMethodfor thePreparation ofPEGylatedLiposomes.... ........ ....... ....... ........ ....... ........ 159 SherifE.Emam,NehalE.Elsadek,TaroShimizu, andTatsuhiroIshida 15 ClickChemistryforLiposomeSurfaceModification ......... ....... ........ 173 MariaVittoriaSpanedda,MarcellaDeGiorgi,BeátriceHeurtault, AntoineKichler,LineBourel-Bonnet,andBenoıˆtFrisch 16 SurfaceModificationofLiposomesUsingFolicAcid......... ....... ........ 191 MengranGuo,ZhongshanHe,XiHe,andXiangrongSong 17 PreparationandCharacterizationofTrastuzumabFab-Conjugated Liposomes(Immunoliposomes) ..... ....... ..... .. ...... .. ...... ...... ... 197 ShanShanJin,HuiminLi,andYuhongXu 18 Pyrophosphorylated-Cholesterol-ModifiedBone-Targeting LiposomeFormulationProcedure .......... ....... ........ ....... ........ 207 YanzhiLiu,ZhenshanJia,LuoyangMa,andDongWang 19 MethodofSimultaneousAnalysisofLiposomeComponents UsingHPTLC/FID ....... ........ ....... ....... ........ ....... ........ 221 SophiaHatziantoniouandCostasDemetzos 20 High-PerformanceLiquidChromatographyCoupledwithTandem MassSpectrometryMethodfor theIdentificationandQuantification ofLipidsinLiposomes .. ... ........ ....... ....... ........ ....... ........ 227 YujieShiandXiaonaLi 21 DPHProbeMethodforLiposome-MembraneFluidity Determination...... ....... ........ ....... ....... ........ ....... ........ 241 WeiHe 22 ImagingofLiposomesbyNegativeStainingTransmissionElectron MicroscopyandCryogenicTransmissionElectronMicroscopy ....... ..... ... 245 AnandS.Ubhe 23 VisualizationandCharacterizationofLiposomesbyAtomic ForceMicroscopy.......... ........ ....... ....... ........ ....... ........ 253 KonradEngelhardt,EduardPreis,andUdoBakowsky 24 DeterminationoftheSubcellularDistributionofFluorescently LabeledLiposomesUsingConfocalMicroscopy..... ........ ....... ........ 265 MelaniA.Solomon 25 LiposomeBiodistributionviaEuropiumComplexes.......... ....... ........ 277 NathalieMignetandDanielScherman 26 QuantificationofaFluorescentLipidDOPE-NBDbyanHPLC MethodinBiologicalTissue:ApplicationtoStudyLiposomes’ UptakebyHumanPlacenta......... ....... ....... ........ ....... ........ 289 LouiseFliedel,NathalieMignet,ThierryFournier, KarineAndrieux,andKhairAlhareth Index .......... ........ ....... ........ ....... ....... ........ ....... ........ 303 Contributors MOHAMADALAWAK • DepartmentofPharmaceuticsandBiopharmaceutics, Universityof Marburg,Marburg,Germany KHAIRALHARETH • Universite´ParisCite´,CNRS,INSERM,UTCBS,Unite´desTechnologies ChimiquesetBiologiquespourlaSante´,Paris,France KARINEANDRIEUX • Universite´ParisCite´,CNRS,INSERM,UTCBS,Unite´desTechnologies ChimiquesetBiologiquespourlaSante´,Paris,France SOPHIAG.ANTIMISIARIS • LaboratoryofPharmaceuticalTechnology,Departmentof Pharmacy,UniversityofPatras,Patras,Greece;InstituteofChemicalEngineering Sciences,FoundationforResearchandTechnologyHellas,FORTH/ICE-HT,Patras, Greece WAFAARESH • DepartmentofBiomedicalEngineering,UniversityofConnecticut,Storrs, CT,USA IBRAHIMAWAK • DepartmentofPharmaceuticsandBiopharmaceutics,Universityof Marburg,Marburg,Germany UDOBAKOWSKY • DepartmentofPharmaceuticsandBiopharmaceutics,Universityof Marburg,Marburg,Germany MICHELBESSODES • Universite´deParisCite´,CNRS,INSERM,UTCBS,Unite´des TechnologiesChimiquesetBiologiquespourlaSante´,Faculte´dePharmacie,Paris,France LINE BOUREL-BONNET • LaboratoiredeConceptionetApplicationsdesMolećulesBioactives, UMR7199CNRS/Universite´deStrasbourg,e´quipe3BIO,Faculte´dePharmacie,Illkirch, France JIANCHEN • SchoolofPharmacy,ShanghaiJiaoTongUniversity,Shanghai,China ZHUCHEN • DepartmentofMechanicalEngineering,UniversityofMaryland,CollegePark, MD,USA ALICEABUDAYYIH • DepartmentofPharmaceuticsandBiopharmaceutics,Universityof Marburg,Marburg,Germany MARCELLADEGIORGI • LaboratoiredeConceptionetApplicationsdesMolećulesBioactives, UMR7199CNRS/Universite´deStrasbourg,e´quipe3BIO,Faculte´dePharmacie,Illkirch, France COSTASDEMETZOS • FacultyofPharmacy,DepartmentofPharmaceuticalTechnology, NationalandKapodistrianUniversityofAthens,Athens,Greece DONL.DEVOE • DepartmentofMechanicalEngineering,UniversityofMaryland,College Park,MD,USA HE´LE`NEDHOTEL • Universite´deParisCite´,CNRS,INSERM,UTCBS,Unite´des TechnologiesChimiquesetBiologiquespourlaSante´,Faculte´dePharmacie,Paris,France GUANGSHENG DU • WestChinaSchoolofPharmacy,SichuanUniversity,Chengdu,China NEHALE.ELSADEK • DepartmentofPharmacokineticsandBiopharmaceutics,Instituteof BiomedicalSciences,TokushimaUniversity,Tokushima,Japan SHERIFE.EMAM • DepartmentofPharmacokineticsandBiopharmaceutics,Instituteof BiomedicalSciences,TokushimaUniversity,Tokushima,Japan;FacultyofPharmacy, DepartmentofPharmaceuticsandIndustrialPharmacy,ZagazigUniversity,Zagazig, Egypt ix x Contributors KONRADENGELHARDT • DepartmentofPharmaceuticsandBiopharmaceutics,Universityof Marburg,Marburg,Germany JUSTINM.FANG • DepartmentofBiomedicalEngineering,UniversityofConnecticut,Storrs, CT,USA LOUISEFLIEDEL • Universite´ParisCite´,CNRS,INSERM,UTCBS,Unite´desTechnologies ChimiquesetBiologiquespourlaSante´,Paris,France;Universite´ParisCite´,INSERM, PathophysiologyandPharmacotoxicologyoftheHumanPlacenta,PreandPostnatal MicrobiotaUnit(3PHM),Paris,France THIERRYFOURNIER • Universite´ParisCite´,INSERM,Pathophysiologyand PharmacotoxicologyoftheHumanPlacenta,PreandPostnatalMicrobiotaUnit(3PHM), Paris,France BENOIˆTFRISCH • LaboratoiredeConceptionetApplicationsdesMolećulesBioactives,UMR 7199CNRS/Universite´deStrasbourg,e´quipe3BIO,Faculte´dePharmacie,Illkirch,France MENGRANGUO • DepartmentofCriticalCareMedicine,StateKeyLaboratoryofBiotherapy andCancerCenter,WestChinaHospital,SichuanUniversity,Chengdu,China BERNDGUTBERLET • DepartmentofPharmaceuticsandBiopharmaceutics,Universityof Marburg,Marburg,Germany JUNGYEONHAN • DepartmentofMechanicalEngineering,UniversityofMaryland,College Park,MD,USA SOPHIAHATZIANTONIOU • DepartmentofPharmacy,LaboratoryofPharmaceutical Technology,SchoolofHealthSciences,UniversityofPatras,Rion,Greece WEIHE • SchoolofPharmacy,ChinaPharmaceuticalUniversity,Nanjing,China XIHE • DepartmentofCriticalCareMedicine,StateKeyLaboratoryofBiotherapyand CancerCenter,WestChinaHospital,SichuanUniversity,Chengdu,China ZHONGSHANHE • DepartmentofCriticalCareMedicine,StateKeyLaboratoryof BiotherapyandCancerCenter,WestChinaHospital,SichuanUniversity,Chengdu,China BEÁTRICEHEURTAULT • LaboratoiredeConceptionetApplicationsdesMolećulesBioactives, UMR7199CNRS/Universite´deStrasbourg,e´quipe3BIO,Faculte´dePharmacie,Illkirch, France TATSUHIROISHIDA • DepartmentofPharmacokineticsandBiopharmaceutics,Instituteof BiomedicalSciences,TokushimaUniversity,Tokushima,Japan ZHENSHANJIA • DepartmentofPharmaceuticalSciences,CollegeofPharmacy,Universityof NebraskaMedicalCenter,Omaha,NE,USA SHANSHANJIN • HangzhouHighfiledBipharmaceuticalsInc.,Hangzhou,China ANTOINEKICHLER • LaboratoiredeConceptionetApplicationsdesMolećulesBioactives, UMR7199CNRS/Universite´deStrasbourg,e´quipe3BIO,Faculte´dePharmacie,Illkirch, France HUIMINLI • YunnanKeyLaboratoryofScreeningandResearchonAnti-pathogenPlant ResourcesinWesternYunnan,DaliUniversity,Dali,China XIAONALI • DepartmentofPharmacy,PekingUniversityThirdHospital,Beijing,People’s RepublicofChina YANZHILIU • DepartmentofPharmaceuticalSciences,CollegeofPharmacy,Universityof NebraskaMedicalCenter,Omaha,NE,USA;ZhanjiangCentralHospital,Guangdong MedicalUniversity,Zhanjiang,PRChina YING LIU • DepartmentofChemicalandBiomolecularEngineering,Universityof Connecticut,Storrs,CT,USA