title: Perylene diimide G-quadruplex DNA binding selectivity is mediated by ligand aggregation.
abstract: Two N,N'-disubstituted perylene diimide G-quadruplex DNA ligands, PIPER [N,N'-bis-(2-(1-piperidino)ethyl)-3,4,9,10-perylene tetracarboxylic acid diimide] and Tel01 [N,N'-bis-(3-(4-morpholino)-propyl)-3,4,9,10-perylene tetracarboxylic acid diimide] were studied. Visible absorbance, resonance light scattering, and fluorescence spectroscopy were used to characterize the pH-dependent aggregation of these ligands. The G-quadruplex DNA binding selectivity of these ligands as monitored by absorption spectroscopy is also pH-dependent. The ligands bind to both duplex and G-quadruplex DNA under low pH conditions, where the ligands are not aggregated. At higher pH, where the ligands are extensively aggregated, the apparent G-quadruplex DNA binding selectivity is high.
authors.affiliation: Division of Medicinal Chemistry, College of Pharmacy, The University of Texas at Austin, 78712, Austin, TX 78712, USA. skerwin@mail.utexas.edu
authors.forename: Sean M
authors.initials: SM
authors.lastname: Kerwin
authors.forename: Grace
authors.initials: G
authors.lastname: Chen
authors.forename: Jonathan T
authors.initials: JT
authors.lastname: Kern
authors.forename: Pei Wang
authors.initials: PW
authors.lastname: Thomas
mesh_terms: D000873:Anthracenes / Q000737:chemistry* / Q000378:metabolism; D004247:DNA / Q000378:metabolism*; D005456:Fluorescent Dyes; D006860:Hydrogen Bonding; D006863:Hydrogen-Ion Concentration; D008027:Light; D009682:Magnetic Resonance Spectroscopy; D009690:Nucleic Acid Conformation; D010569:Perylene / Q000031:analogs & derivatives / Q000737:chemistry* / Q000378:metabolism; D010880:Piperidines / Q000737:chemistry* / Q000378:metabolism; D010881:Piperidones / Q000737:chemistry* / Q000378:metabolism; D012542:Scattering, Radiation; D013050:Spectrometry, Fluorescence; D013056:Spectrophotometry, Ultraviolet
chemical_list: D000873:Anthracenes; D005456:Fluorescent Dyes; C116108:N,N'-bis(2-1(piperidino)-ethyl)-3,4,9,10-perylene-tetracarboxylic diimide; C456408:N,N'-bis(3-(4-morpholino)propyl)-3,4,9,10-perylenetetracarboxylic acid diimide; D010880:Piperidines; D010881:Piperidones; D010569:Perylene; D004247:DNA