title: Detection of CAG repeat DNA sequences by pyrene-functionalized pyrrole-imidazole polyamides.
abstract: Five N-methylpyrrole-N-methylimidazole (Py-Im) polyamides possessing a fluorescent pyrene were synthesized by Fmoc solid-phase synthesis using Py/Im monomers and pyrenylbutyl-pyrrole monomer compound 9. The steady state fluorescence of conjugates 1-5 was examined in the presence and absence of (CAG)(12)-containing oligodeoxynucleotides (ODNs) 1 and 2. Of the conjugates, conjugate 1 showed no background emission around 470 nm in the absence of ODNs, and a clear increase of emission at 475 nm was observed upon addition of ODNs 1 and 2. The emission of conjugate 1 at 475 nm increased linearly with the concentration of ODN and the number of CAG repeats. The results indicate that conjugate 1 efficiently forms a pyrene excimer upon binding in the minor groove of DNA.
authors.affiliation: Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan.
authors.forename: Toshikazu
authors.initials: T
authors.lastname: Bando
authors.forename: Jun
authors.initials: J
authors.lastname: Fujimoto
authors.forename: Masafumi
authors.initials: M
authors.lastname: Minoshima
authors.forename: Ken-Ichi
authors.initials: K
authors.lastname: Shinohara
authors.forename: Shunta
authors.initials: S
authors.lastname: Sasaki
authors.forename: Gengo
authors.initials: G
authors.lastname: Kashiwazaki
authors.forename: Masatoshi
authors.initials: M
authors.lastname: Mizumura
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Sugiyama
mesh_terms: D001483:Base Sequence; D004247:DNA / Q000032:analysis*; D005453:Fluorescence; D007093:Imidazoles / Q000737:chemistry*; D009757:Nylons / Q000138:chemical synthesis / Q000737:chemistry*; D009838:Oligodeoxyribonucleotides / Q000737:chemistry; D011721:Pyrenes / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry*; D017422:Sequence Analysis, DNA / Q000379:methods; D013050:Spectrometry, Fluorescence / Q000379:methods; D018911:Trinucleotide Repeats