Table Of ContentControl of Amphiphile Self-Assembling
at the Molecular Level:
Supra-Molecular Assemblies
with Tuned Physicochemical Properties
for Delivery Applications
1271
ACS SYMPOSIUM SERIES
Control of Amphiphile Self-Assembling
at the Molecular Level:
Supra-Molecular Assemblies
with Tuned Physicochemical Properties
for Delivery Applications
Marc A. Ilies, Editor
Temple University School of Pharmacy
Philadelphia, Pennsylvania
Sponsored by the
ACSDivisionofColloidandSurfaceChemistry
AmericanChemicalSociety,Washington,DC
DistributedinprintbyOxfordUniversityPress
LibraryofCongressCataloging-in-PublicationData
Names:Ilies,MarcA.,editor.|AmericanChemicalSociety.Divisionof
ColloidandSurfaceChemistry.
Title:Controlofamphiphileself-assemblingatthemolecularlevel:
supra-molecularassemblieswithtunedphysicochemicalpropertiesfor
deliveryapplications/MarcA.Ilies,editor,TempleUniversitySchoolof
Pharmacy,Philadelphia,Pennsylvania;sponsoredbytheACSDivisionof
ColloidandSurfaceChemistry.
Description:Washington,DC:AmericanChemicalSociety,[2017]|Series:ACS
symposiumseries;1271|Includesbibliographicalreferencesandindex.
Identifiers:LCCN2017052433(print)|LCCN2017054832(ebook)|ISBN
9780841232730(ebook)|ISBN9780841232747
Subjects:LCSH:Amphiphiles.|Self-assembly(Chemistry)|Biological
transport.|Supramolecularchemistry.
Classification:LCCQD382.A47(ebook)|LCCQD382.A47C662017(print)|DDC
615.1/9--dc23
LCrecordavailableathttps://lccn.loc.gov/2017052433
ThepaperusedinthispublicationmeetstheminimumrequirementsofAmericanNational
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Foreword
The ACS Symposium Series was first published in 1974 to provide a
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Beforeagreeingtopublishabook,theproposedtableofcontentsisreviewed
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Contents
Preface.............................................................................................................................. ix
1. SyntheticDeliverySystemsforDNA,siRNA,andmRNABasedon
PyridiniumAmphiphiles ......................................................................................... 1
MarcAIlies,UttamSatyal,andVishnuD.Sharma
2. DesigningPolymerMicellesofControlledSize,Stability,andFunctionality
forsiRNADelivery................................................................................................. 35
ChristinaM.Bailey,RamanathanNagarajan,andTerriA.Camesano
3. UtilizingCholesterolNanodomainsforNucleicAcidDelivery.......................... 71
JamieL.Betker,LongXu,YeZhang,andThomasJ.Anchordoquy
4. InSilicoSelf-AssemblyofNanoparticleswithApplicationsinDrug
Delivery ................................................................................................................... 95
EditheSelwaandBogdanI.Iorga
5. CharacterizingPEGChainsTetheredontoMicellesandLiposomesApplied
asDrugDeliveryVehiclesUsingScatteringTechniques .................................. 115
ShotaFujii,MinaSakuragi,andKazuoSakurai
6. StrategiesforFunctionalizingLipoprotein-BasedNanoparticles ................... 131
SeanF.Gilmore,WeiHe,AmyRasley,andNicholasO.Fischer
7. RationallyControlledSelf-AssemblyBehaviorofInorganic-Organic
HybridsinSolution .............................................................................................. 151
YangChuandTianboLiu
8. Sn2LipaseLabileProdrugsandContact-FacilitatedDrugDeliveryfor
Lipid-EncapsulatedNanomedicines................................................................... 189
D.Pan,G.Cui,C.T.N.Pham,M.H.Tomasson,K.N.Weilbaecher,andG.M.Lanza
9. Interface-EngineeredAmphiphilicBlockCopolymerswithTuned
EnzymaticResistanceforControlledDeliveryofChemotherapeutic
Drugs ..................................................................................................................... 211
UttamSatyal,VishnuDuttSharma,JenniferA.Shif,andMarcA.Ilies
10. BiocompatibleNanoparticlesforSelectiveDrugReleaseatCancerCells ..... 231
FilizKaragöz,RobertDorresteijn,KlausMüllen,andMarkusKlapper
vii
11. InverseFlashNanoPrecipitationforBiologicsEncapsulation: Nanoparticle
FormationandIonicStabilizationinOrganicSolvents ................................... 249
RobertF.PagelsandRobertK.Prud’homme
12. Inverse Flash NanoPrecipitation for Biologics Encapsulation:
UnderstandingProcessLossesviaanExtractionProtocol .............................. 275
ChesterE.MarkwalterandRobertK.Prud’homme
13. EngineeredCellPenetratingPeptides................................................................ 297
WeiliMaandWonH.Suh
Editor’sBiography....................................................................................................... 321
Indexes
AuthorIndex ................................................................................................................ 325
SubjectIndex................................................................................................................ 327
viii
Preface
This book has its sources in the symposium with the same title, held at the
252nd ACS National Meeting in Philadelphia, PA on August 21–25, 2016. The
symposiumwassponsoredbytheACSDivisionofColloidandSurfaceChemistry,
aspartofitscontinuingsymposiaonamphiphilesandtheirself-assemblies. Iam
indebted to Dr. Ramanathan Nagarajan (Natick Soldier Research, Development
&EngineeringCenter,Natick,MA),ProgramChairforACSDivisionofColloid
and Surface Chemistry, for his efforts to accommodate this symposium, for his
scientific contributions to the symposium and to this book, and for his constant
support.
The main focus of the book is the design, synthesis and characterization
of amphiphile self-assemblies and the dynamic assessment of these assemblies
as delivery systems for drugs and nucleic acids. As delivery systems, these
supra-molecular assemblies have the ability to change the pharmacokinetics
and volume of distribution of their cargo, to protect it from premature
decomposition or inactivation, and to control the spatial-temporal location
and duration of the therapeutic effect associated with cargo delivery. Many
biocompatible/biodegradable delivery systems present in the market today or
in advanced clinical trials are made of self-assembled amphiphilic molecules
of different types and molecular weights. Their physicochemical and delivery
abilitiesaredeterminedbyphysicochemicalparametersofindividualamphiphiles
and of the loaded cargo. Therefore, substantial efforts were made towards the
design of novel amphiphiles with encapsulation and delivery properties tailored
fordifferentcargosandfordifferentbiologicalapplications.
Different chapters of the book present delivery systems made out of
large variety of amphiphiles, including simple surfactants, gemini surfactants,
pseudo-gemini surfactants, lipids, lipophilic polycations, dendrimers, natural
and synthetic polymers and their conjugates. The cargo encapsulated by these
amphiphiles is quite diverse too: chemotherapeutic cytotoxic drugs, peptide,
proteins, nucleic acids (pDNA, siRNA, mRNA). The book also presents the
formulation protocols and parameters used in the component or cargo loading
process, with theoretical support and rationale. It reveals how formulation
technology can affect the drug loading ability, physicochemical properties,
dynamicstabilityandunloadingpropertiesofthedeliverysystem,acrossdifferent
classesofamphiphilesandcargos.
Twomaindifferentstrategiesarecurrentlyusedinthedesignofamphiphile-
based delivery systems for drugs and nucleic acids. In formulation-based
strategies, amphiphiles of different packing parameters and physicochemical
properties are blended together, simultaneously or sequentially with the cargo,
ix
