title: Design and synthesis of highly solvatochromic fluorescent 2'-deoxyguanosine and 2'-deoxyadenosine analogs.
abstract: We synthesized various substituted 8-styryl-2'-deoxyguanosine and 8-styryl-2'-deoxyadenosine derivatives. Among them only acetyl substituted 8-styryl-2'-deoxyguanosine analog 5b showed a remarkable solvatochromicity (Δλ(max)(em)=91 nm),that is, strong fluorescence at 477 nm in 1,4-dioxane, but in methanol the fluorescence was red shifted to 558 nm with very low intensity. Such environmentally sensitive solvatochromic fluorescent guanosine analogs may be useful as a sensor for investigating interactions of DNA with DNA binding proteins.
authors.affiliation: Institute of Advanced Energy, Kyoto University, Uji, Kyoto 611-0011, Japan.
authors.forename: Katsuhiko
authors.initials: K
authors.lastname: Matsumoto
authors.forename: Naoya
authors.initials: N
authors.lastname: Takahashi
authors.forename: Azusa
authors.initials: A
authors.lastname: Suzuki
authors.forename: Takashi
authors.initials: T
authors.lastname: Morii
authors.forename: Yoshio
authors.initials: Y
authors.lastname: Saito
authors.forename: Isao
authors.initials: I
authors.lastname: Saito
mesh_terms: D004247:DNA / Q000737:chemistry / Q000378:metabolism; D004268:DNA-Binding Proteins / Q000737:chemistry / Q000378:metabolism; D003839:Deoxyadenosines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D003849:Deoxyguanosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D015195:Drug Design; D012997:Solvents / Q000737:chemistry*; D013050:Spectrometry, Fluorescence; D013343:Styrenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
chemical_list: C558294:8-(4-acetylstyryl)-2'-deoxyguanosine; D004268:DNA-Binding Proteins; D003839:Deoxyadenosines; D012997:Solvents; D013343:Styrenes; D004247:DNA; D003849:Deoxyguanosine; C058118:2'-deoxyadenosine