title: Enhancement of fluorescence quenching and exciplex formation in DNA major groove by double incorporation of modified fluorescent deoxyuridines.
abstract: 5-(1-Naphthalenylethynyl)-2'-deoxyuridine ((N)U) and 5-[(4-cyano-1-naphthalenyl)ethynyl]-2'-deoxyuridine ((CN)U) were synthesized and incorporated into oligodeoxynucleotides. Fluorescence emissions of modified duplexes containing double (N)U were efficiently quenched depending upon the sequence pattern of the naphthalenes in DNA major groove, as compared to the duplex possessing single (N)U. When one of the naphthalene moieties has a cyano substituent, the exciplex emission from the chromophores in DNA major groove was observed at longer wavelength.
authors.affiliation: Department of Chemical Biology and Applied Chemistry, School of Engineering, Nihon University, Koriyama, Fukushima 963-8642, Japan.
authors.forename: Makiko
authors.initials: M
authors.lastname: Tanaka
authors.forename: Kazuhiro
authors.initials: K
authors.lastname: Oguma
authors.forename: Yoshio
authors.initials: Y
authors.lastname: Saito
authors.forename: Isao
authors.initials: I
authors.lastname: Saito
mesh_terms: D004247:DNA / Q000737:chemistry*; D003857:Deoxyuridine / Q000031:analogs & derivatives* / Q000737:chemistry*; D005453:Fluorescence; D009281:Naphthalenes / Q000737:chemistry*; D009690:Nucleic Acid Conformation; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis*; D013050:Spectrometry, Fluorescence
chemical_list: D009281:Naphthalenes; D009838:Oligodeoxyribonucleotides; D004247:DNA; D003857:Deoxyuridine