title: A Bis(guanidinium)alcohol Attached to a Hairpin Polyamide: Synthesis, DNA Binding, and Plasmid Cleavage.
abstract: Bis(guanidinium)alcohols have been designed to react with phosphodiester substrates in a fast transphosphorylation step, a quasi-intramolecular process taking place in contact ion pairs. Here the attachment of such compounds to Dervan-type hairpin polyamides is described. The resulting conjugate 1 binds to AT-rich DNA duplexes with affinity similar to that of the parent polyamide as shown by UV melting experiments and CD titrations. Conjugate 1 nicks plasmid DNA at concentrations ranging from micromolar to high nanomolar.
authors.affiliation: Institut für Organische Chemie und Chemische Biologie, Johann Wolfgang Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438, Frankfurt am Main, Germany.
authors.forename: Daniela
authors.initials: D
authors.lastname: Wirth-Hamdoune
authors.affiliation: Institut für Organische Chemie und Chemische Biologie, Johann Wolfgang Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438, Frankfurt am Main, Germany.
authors.forename: Stefan
authors.initials: S
authors.lastname: Ullrich
authors.affiliation: Institut für Organische Chemie und Chemische Biologie, Johann Wolfgang Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438, Frankfurt am Main, Germany.
authors.forename: Ute
authors.initials: U
authors.lastname: Scheffer
authors.affiliation: Institut für Organische Chemie und Chemische Biologie, Johann Wolfgang Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438, Frankfurt am Main, Germany.
authors.forename: Toni
authors.initials: T
authors.lastname: Radanović
authors.affiliation: Institut für Organische Chemie und Chemische Biologie, Johann Wolfgang Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438, Frankfurt am Main, Germany.
authors.forename: Gerd
authors.initials: G
authors.lastname: Dürner
authors.affiliation: Institut für Organische Chemie und Chemische Biologie, Johann Wolfgang Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438, Frankfurt am Main, Germany. M.Goebel@chemie.uni-frankfurt.de.
authors.forename: Michael W
authors.initials: MW
authors.lastname: Göbel
mesh_terms: D001665:Binding Sites; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D004247:DNA / Q000737:chemistry*; D019791:Guanidine / Q000138:chemical synthesis / Q000737:chemistry*; D009757:Nylons / Q000737:chemistry*; D010957:Plasmids; D021241:Spectrometry, Mass, Electrospray Ionization; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
chemical_list: D009757:Nylons; D004247:DNA; D019791:Guanidine
keywords: DNA cleavage; enzyme models; guanidine; minor groove binders; nucleic acids