title: DNA binding of an organic dppz-based intercalator.
abstract: An improved synthesis of a water-soluble derivative of dipyrido[3,2-a:2',3'-c]phenazine (dppz) is reported. The structures of both dppz and the cation ethylene-bipyridyldiylium-phenazine dinitrate [[1][(PF(6))(2)]] have been obtained via X-ray crystallography. Metal complex derivatives of dppz are very well studied. However, using the water soluble [1][(NO(3))(2)], the nature of the interaction of a simple dppz unit with duplex DNA has been investigated for the first time. In both organic solvents and water, 1 displays unstructured luminescence, assigned to an intramolecular charge transfer. The emission is quenched on binding to natural and synthetic duplex DNA, including poly(dA).poly(dT). A variety of techniques reveal that the cation binds to DNA with an affinity comparable to those of many metal dppz complexes, via an intercalative binding mode.
authors.affiliation: Department of Chemistry, University of Sheffield, Sheffield S3 7HF, UK.
authors.forename: Tim
authors.initials: T
authors.lastname: Phillips
authors.forename: Ihtshamul
authors.initials: I
authors.lastname: Haq
authors.forename: Anthony J H M
authors.initials: AJ
authors.lastname: Meijer
authors.forename: Harry
authors.initials: H
authors.lastname: Adams
authors.forename: Ian
authors.initials: I
authors.lastname: Soutar
authors.forename: Linda
authors.initials: L
authors.lastname: Swanson
authors.forename: Matthew J
authors.initials: MJ
authors.lastname: Sykes
authors.forename: Jim A
authors.initials: JA
authors.lastname: Thomas
mesh_terms: D001665:Binding Sites; D002151:Calorimetry; D018360:Crystallography, X-Ray; D004247:DNA / Q000737:chemistry*; D005454:Fluorescence Polarization; D007364:Intercalating Agents / Q000737:chemistry*; D008163:Luminescent Measurements; D019906:Nuclear Magnetic Resonance, Biomolecular; D010619:Phenazines / Q000737:chemistry*; D011131:Polyribonucleotides / Q000737:chemistry; D013050:Spectrometry, Fluorescence; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013329:Structure-Activity Relationship; D013816:Thermodynamics; D014783:Viscosity
chemical_list: D007364:Intercalating Agents; D010619:Phenazines; D011131:Polyribonucleotides; C443808:dipyrido(3,2-a-2',3'-c)phenazine; D004247:DNA; C427203:calf thymus DNA