A Bis(guanidinium)alcohol Attached to a Hairpin Polyamide: Synthesis, DNA Binding, and Plasmid Cleavage. (16th February 2016)

• Record Type: Journal Article
• Authors: Wirth‐Hamdoune, Daniela; Ullrich, Stefan; Scheffer, Ute; Radanović, Toni; Dürner, Gerd; Göbel, Michael W.
• Is Part Of: Chembiochem. Volume 17:Number 6(2016)
• Page Start: 506
• Page End: 514
• Publication Date: 2016-02-16
• Subjects: DNA cleavage -- enzyme models -- guanidine -- minor groove binders -- nucleic acids; Biochemistry -- Periodicals; Molecular biology -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1002/cbic.201500566
• Languages: English
• ISSNs: 1439-4227

Abstract

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. Abstract : Nicked ! A cationic alcohol designed to form ion‐pair complexes with phosphate diesters and to react by nucleophilic displacement has been attached to a DNA‐binding Dervan‐type hairpin polyamide. The resulting conjugate nicks plasmid DNA at concentrations ranging from micromolar to high nanomolar.