title: Incorporation of a Non-Natural Arginine Analogue into a Cyclic Peptide Leads to Formation of Positively Charged Nanofibers Capable of Gene Transfection.
abstract: Functionalization of the tetracationic cyclic peptide (Ka)4 with a single guanidiniocarbonyl pyrrole (GCP) moiety, a weakly basic but highly efficient arginine analogue, completely alters the self-assembly properties of the peptide. In contrast to the nonfunctionalized peptide 2, which does not self-assemble, GCP-containing peptide 1 forms cationic nanofibers of micrometer length. These aggregates are efficient gene transfection vectors. DNA binds to their cationic surface and is efficiently delivered into cells.
authors.affiliation: Institute for Organic Chemistry, University of Duisburg-Essen, 45117 Essen (Germany).
authors.forename: Mao
authors.initials: M
authors.lastname: Li
authors.affiliation: Institute for Organic Chemistry, University of Duisburg-Essen, 45117 Essen (Germany).
authors.forename: Martin
authors.initials: M
authors.lastname: Ehlers
authors.affiliation: Institute for Biology, University of Duisburg-Essen, 45117 Essen (Germany).
authors.forename: Stefanie
authors.initials: S
authors.lastname: Schlesiger
authors.affiliation: Institute for Organic Chemistry, University of Duisburg-Essen, 45117 Essen (Germany).
authors.forename: Elio
authors.initials: E
authors.lastname: Zellermann
authors.affiliation: Institute for Biology, University of Duisburg-Essen, 45117 Essen (Germany).
authors.forename: Shirley K
authors.initials: SK
authors.lastname: Knauer
authors.affiliation: Institute for Organic Chemistry, University of Duisburg-Essen, 45117 Essen (Germany). carsten.schmuck@uni-due.de.
authors.forename: Carsten
authors.initials: C
authors.lastname: Schmuck
mesh_terms: D001120:Arginine / Q000031:analogs & derivatives*; D004247:DNA / Q000737:chemistry; D018625:Microscopy, Atomic Force; D046529:Microscopy, Electron, Transmission; D057139:Nanofibers; D010456:Peptides, Cyclic / Q000737:chemistry*; D014162:Transfection
chemical_list: D010456:Peptides, Cyclic; D004247:DNA; D001120:Arginine
keywords: cellular uptake; cyclic peptides; gene delivery; nanostructures; self-assembly