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Chemical-Functional Diversity in Cell-Penetrating Peptides.doc

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Chemical-Functional Diversity in Cell-Penetrating Peptides

Chemical-FunctionalDiversityinCell-Penetrating Peptides SofieStalmans1,EvelienWynendaele1,NathalieBracke1,BertGevaert1,MatthiasD’Hondt1, KathelijnePeremans2,ChristianBurvenich2,BartDeSpiegeleer1* 1Drug Quality and Registration (DruQuaR) Group, Faculty of Pharmaceutical Sciences, Ghent University, Ghent, Belgium, 2Department of Medical Imaging and ComparativePhysiologyandBiometrics,FacultyofVeterinaryMedicine,GhentUniversity,Merelbeke,Belgium Abstract Cell-penetrating peptides (CPPs) are a promising tool to overcome cell membrane barriers. They have already been successfullyappliedascarriersforseveralproblematiccargoes,likee.g.plasmidDNAand(si)RNA,openingdoorsfornew therapeutics.AlthoughseveralhundredsofCPPsarealreadydescribedintheliterature,onlyafewcommercialapplications ofCPPsarecurrentlyavailable.Cellularuptakestudiesofthesepeptidessufferfrominconsistenciesinusedtechniquesand otherexperimentalconditions,leadingtouncertaintiesabouttheiruptakemechanismsandstructuralproperties.Toclarify the structural characteristics influencing the cell-penetrating properties of peptides, the chemical-functional space of peptides,alreadyinvestigatedforcellularuptake,wasexplored.For186peptides,anewcell-penetrating(CP)-responsewas proposed,baseduponthescatteredquantitativeresultsforcellularinfluxavailableintheliterature.Principalcomponent analysis(PCA)andaquantitativestructure-propertyrelationshipstudy(QSPR),usingchemo-moleculardescriptorsandour newly defined CP-response, learned that besides typical well-known properties of CPPs, i.e. positive charge and amphipathicity, the shape, structure complexity and the 3D-pattern of constituting atoms influence the cellular uptake capacityofpeptides. Citation: StalmansS,WynendaeleE,BrackeN,GevaertB,D’HondtM,etal.(2013)Chemical-Functional Diversity inCell-PenetratingPeptides.PLoSONE8(8): e71752.doi:10.1371/journal.pone.0071752 Editor:PaulTaylor,UniversityofEdinburgh,UnitedKingdom ReceivedApril18,2013;AcceptedJuly3,2013;PublishedAugust