title: Arginine clustering on calix[4]arene macrocycles for improved cell penetration and DNA delivery.
abstract: Cell-penetrating peptides are widely used as molecular transporters for the internalization inside cells of various cargo, including proteins and nucleic acids. A special role is played by arginine-rich peptides and oligoarginines covalently linked or simply mixed with the cargo. Here we report cell-penetrating agents in which arginine units are clustered on a macrocyclic scaffold. Instead of using long peptides, four single arginine units were covalently attached to either the upper or lower rim of a calix[4]arene, kept in the cone conformation building a 'parallel' cyclic array. These new macrocyclic carriers show high efficiency in DNA delivery and transfection in a variety of cell lines.
authors.affiliation: Dipartimento di Chimica, Università degli Studi di Parma, Parma, Italy.
authors.forename: Valentina
authors.initials: V
authors.lastname: Bagnacani
authors.forename: Valentina
authors.initials: V
authors.lastname: Franceschi
authors.forename: Michele
authors.initials: M
authors.lastname: Bassi
authors.forename: Michela
authors.initials: M
authors.lastname: Lomazzi
authors.forename: Gaetano
authors.initials: G
authors.lastname: Donofrio
authors.forename: Francesco
authors.initials: F
authors.lastname: Sansone
authors.forename: Alessandro
authors.initials: A
authors.lastname: Casnati
authors.forename: Rocco
authors.initials: R
authors.lastname: Ungaro
mesh_terms: D000818:Animals; D001120:Arginine / Q000378:metabolism*; D047250:Calixarenes / Q000378:metabolism* / Q000493:pharmacokinetics; D004247:DNA / Q000008:administration & dosage*; D006801:Humans; D047028:Macrocyclic Compounds / Q000378:metabolism* / Q000493:pharmacokinetics; D010636:Phenols / Q000378:metabolism* / Q000493:pharmacokinetics; D014162:Transfection
chemical_list: D047028:Macrocyclic Compounds; D010636:Phenols; C121325:calix(4)arene; D047250:Calixarenes; D004247:DNA; D001120:Arginine