title: Naphthalene-based environmentally sensitive fluorescent 8-substituted 2'-deoxyadenosines: application to DNA detection.
abstract: We synthesized various C8-naphthylethynylated 2'-deoxyadenosine derivatives and investigated their photophysical properties. Among them, cyano- and N,N-dimethylamino-substituted 8-naphthylethynylated 2'-deoxyadenosine derivatives ((cn)A and (dn)A) showed strong fluorescence with high quantum yields and a remarkable solvatofuorochromicity. In particular, fluorescence of N,N-dimethylamino-substituted (2,6dn)A was not quenched by neighboring guanines (Gs) when incorporated in DNA duplexes, in contrast to (cn)A. We developed a new fluorescent probe containing (2,6dn)A that can be used for the detection of target DNA via a bulge formation regardless of the neighboring sequences.
authors.affiliation: Department of Chemical Biology and Applied Chemistry, School of Engineering, Nihon University, Koriyama, Fukushima 963-8642, Japan.
authors.forename: Azusa
authors.initials: A
authors.lastname: Suzuki
authors.forename: Naoya
authors.initials: N
authors.lastname: Takahashi
authors.forename: Yuji
authors.initials: Y
authors.lastname: Okada
authors.forename: Isao
authors.initials: I
authors.lastname: Saito
authors.forename: Nobukatsu
authors.initials: N
authors.lastname: Nemoto
authors.forename: Yoshio
authors.initials: Y
authors.lastname: Saito
mesh_terms: D004247:DNA / Q000032:analysis* / Q000737:chemistry; D003839:Deoxyadenosines / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry*; D057230:Limit of Detection; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*
chemical_list: D003839:Deoxyadenosines; D005456:Fluorescent Dyes; D009281:Naphthalenes; C031721:naphthalene; D004247:DNA; C058118:2'-deoxyadenosine