title: Cell-penetrating peptoids: introduction of novel cationic side chains.
abstract: During the last decade peptoid-based molecular transporters have been broadly applied. They are highly valued for their easy synthesis and their superior stability against enzymatic degradation. The special structure of peptoids generally allows introducing a variety of different side chains. Yet, the cationic side chains of cell-penetrating peptoids displayed solely lysine- or arginine-like structures. Thus this report is intended to extend the spectrum of cationic peptoid side chains. Herein, we present novel functional groups, like polyamines, aza-crown ethers, or triphenylphosphonium ions that are introduced into peptoids for the first time. In addition, the obtained peptoids were tested for their cell-penetrating properties.
authors.affiliation: Karlsruhe Institute of Technology (KIT), Institute of Organic Chemistry, Fritz-Haber-Weg 6, D-76131 Karlsruhe, Germany.
authors.forename: Dominik K
authors.initials: DK
authors.lastname: Kölmel
authors.affiliation: Karlsruhe Institute of Technology (KIT), Institute of Organic Chemistry, Fritz-Haber-Weg 6, D-76131 Karlsruhe, Germany; Karlsruhe Institute of Technology (KIT), Light Technology Institute, Engesserstraße 13, D-76131 Karlsruhe, Germany.
authors.forename: Anna
authors.initials: A
authors.lastname: Hörner
authors.affiliation: Karlsruhe Institute of Technology (KIT), Institute of Toxicology and Genetics, Hermann-von-Helmholtz-Platz 1, D-76344 Eggenstein-Leopoldshafen, Germany.
authors.forename: Franziska
authors.initials: F
authors.lastname: Rönicke
authors.affiliation: University of Helsinki, Laboratory of Inorganic Chemistry, PO Box 55, FIN-00014, Finland.
authors.forename: Martin
authors.initials: M
authors.lastname: Nieger
authors.affiliation: Karlsruhe Institute of Technology (KIT), Institute of Toxicology and Genetics, Hermann-von-Helmholtz-Platz 1, D-76344 Eggenstein-Leopoldshafen, Germany.
authors.forename: Ute
authors.initials: U
authors.lastname: Schepers
authors.affiliation: Karlsruhe Institute of Technology (KIT), Institute of Organic Chemistry, Fritz-Haber-Weg 6, D-76131 Karlsruhe, Germany; Karlsruhe Institute of Technology (KIT), Institute of Toxicology and Genetics, Hermann-von-Helmholtz-Platz 1, D-76344 Eggenstein-Leopoldshafen, Germany. Electronic address: braese@kit.edu.
authors.forename: Stefan
authors.initials: S
authors.lastname: Bräse
mesh_terms: D001372:Aza Compounds / Q000737:chemistry*; D002412:Cations / Q000737:chemistry; D057846:Cell-Penetrating Peptides / Q000138:chemical synthesis / Q000737:chemistry*; D043844:Crown Ethers / Q000737:chemistry*; D018360:Crystallography, X-Ray; D006367:HeLa Cells; D006801:Humans; D008958:Models, Molecular; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000737:chemistry*; D011073:Polyamines / Q000737:chemistry*; D014407:Tumor Cells, Cultured
chemical_list: D001372:Aza Compounds; D002412:Cations; D057846:Cell-Penetrating Peptides; D043844:Crown Ethers; D009943:Organophosphorus Compounds; D011073:Polyamines
keywords: Cellular uptake; HeLa cell; Molecular transporter; Peptoid; Spermine