title: Molecular design of an environmentally sensitive fluorescent nucleoside, 3-deaza-2'-deoxyadenosine derivative: distinguishing thymine by probing the DNA minor groove.
abstract: An environmentally sensitive fluorescent nucleoside containing a 3-deazaadenine skeleton has been developed, and its photophysical properties were investigated. Newly developed C3-naphthylethynylated 3-deaza-2'-deoxyadenosine ((3nz) A, 1) exhibited dual fluorescence emission from an intramolecular charge-transfer state and a locally excited state, depending upon molecular coplanarity. DNA probes containing 1 clearly discriminated a perfectly matched thymine base on the complementary strand by a distinct change in emission wavelength.
authors.affiliation: Department of Chemical Biology and Applied Chemistry, College of Engineering, Nihon University, Koriyama, Fukushima 963-8642 (Japan).
authors.forename: Azusa
authors.initials: A
authors.lastname: Suzuki
authors.forename: Takumi
authors.initials: T
authors.lastname: Yanaba
authors.forename: Isao
authors.initials: I
authors.lastname: Saito
authors.forename: Yoshio
authors.initials: Y
authors.lastname: Saito
mesh_terms: D004247:DNA / Q000737:chemistry*; D015342:DNA Probes / Q000138:chemical synthesis / Q000737:chemistry*; D005453:Fluorescence; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry*; D008958:Models, Molecular; D013696:Temperature; D013941:Thymine / Q000032:analysis / Q000737:chemistry*; D014372:Tubercidin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D015342:DNA Probes; D005456:Fluorescent Dyes; C065642:3-deaza-2'-deoxyadenosine; D004247:DNA; D014372:Tubercidin; D013941:Thymine
keywords: DNA; bioorganic chemistry; deazaadenine; fluorescent nucleosides; naphthalene