title: Solution conformational features and interfacial properties of an intrinsically disordered peptide coupled to alkyl chains: a new class of peptide amphiphiles.
abstract: Owing to the large panel of biological functions of peptides and their high specificity and potency, the development of peptide-based therapeutic and diagnostic tools has received increasing interest. Peptide amphiphiles (PAs) are an emerging class of molecules in which a bioactive peptide is covalently conjugated to a hydrophobic moiety. Due to the coexistence in the molecule of a hydrophilic peptide sequence and a hydrophobic group, PAs are able to self-assemble spontaneously into a variety of nanostructures, such as monolayers, bilayers, and vesicles. In this work we have synthesized a disordered peptide, henceforth called R11, and two lipophilic derivatives of R11 bearing two alkyl chains, connected or not to R11 by an ethoxylic-based linker. The structural properties in solution of these new PAs were investigated using CD and NMR. R11 lipophilic derivatives display typical features of PAs, such as the formation of micelles and unilamellar vesicles. In addition, their surface properties were studied using Langmuir monomolecular films and the results obtained support the formation of molecular aggregates upon compression of the PA films. The presence of the alkyl chains induces not only the self-assembly of these new PAs into supramolecular aggregates but also a gain of structure within the disordered peptide.
authors.affiliation: Dipartimento di Farmacia and CIRPeB, Università degli Studi Federico II di Napoli, Via Mezzocannone, 16 80134 Naples, Italy.
authors.forename: Antonella
authors.initials: A
authors.lastname: Accardo
authors.forename: Marilisa
authors.initials: M
authors.lastname: Leone
authors.forename: Diego
authors.initials: D
authors.lastname: Tesauro
authors.forename: Rosa
authors.initials: R
authors.lastname: Aufiero
authors.forename: Anaïs
authors.initials: A
authors.lastname: Bénarouche
authors.forename: Jean-François
authors.initials: JF
authors.lastname: Cavalier
authors.forename: Sonia
authors.initials: S
authors.lastname: Longhi
authors.forename: Frederic
authors.initials: F
authors.lastname: Carriere
authors.forename: Filomena
authors.initials: F
authors.lastname: Rossi
mesh_terms: D002942:Circular Dichroism; D057927:Hydrophobic and Hydrophilic Interactions; D064267:Intrinsically Disordered Proteins / Q000737:chemistry*; D008081:Liposomes; D008823:Micelles; D049329:Nanostructures / Q000737:chemistry*; D019906:Nuclear Magnetic Resonance, Biomolecular; D010455:Peptides / Q000032:analysis / Q000138:chemical synthesis / Q000737:chemistry*; D011485:Protein Binding; D011487:Protein Conformation; D013499:Surface Properties; D013501:Surface-Active Agents / Q000737:chemistry*
chemical_list: D064267:Intrinsically Disordered Proteins; D008081:Liposomes; D008823:Micelles; D010455:Peptides; D013501:Surface-Active Agents