title: Fluorescent nucleosides with 'on-off' switching function, pH-responsive fluorescent uridine derivatives.
abstract: We synthesized various pH-responsive fluorescent deoxyuridine derivatives (1a-g). These fluorescent nucleosides exhibited distinctive fluorescence at 470-600 nm in aqueous solvents containing methanol only at acidic to neutral pH values. In particular, 1f exhibited strong fluorescence only at pH range of 3.1-7.2 with a pK(a) of 6.1. Such pH-sensitive fluorescent nucleosides can be used as 'on-off' fluorescence switch for monitoring pH change in biological systems, particularly for cancer cell detection.
authors.affiliation: Department of Chemical Biology and Applied Chemistry, School of Engineering, Nihon University, Koriyama, Fukushima, Japan. saitoy@chem.ce.nihon-u.ac.jp
authors.forename: Yoshio
authors.initials: Y
authors.lastname: Saito
authors.forename: Shigenori
authors.initials: S
authors.lastname: Miyamoto
authors.forename: Azusa
authors.initials: A
authors.lastname: Suzuki
authors.forename: Katsuhiko
authors.initials: K
authors.lastname: Matsumoto
authors.forename: Tsutomu
authors.initials: T
authors.lastname: Ishihara
authors.forename: Isao
authors.initials: I
authors.lastname: Saito
mesh_terms: D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry; D005812:Genes, Switch; D006863:Hydrogen-Ion Concentration; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis / Q000737:chemistry; D014529:Uridine / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D005456:Fluorescent Dyes; D009705:Nucleosides; D014529:Uridine