C2-substituted 8-aza-7-deaza-2′-deoxyadenosines as environmentally sensitive fluorescent nucleosides for discriminating apurinic/apyrimidinic sites in DNA duplex. Issue 2 (11th January 2017)

• Record Type: Journal Article
• Authors: Yamauchi, Takumi; Takeda, Takuya; Yanagi, Masaki; Takahashi, Noriki; Suzuki, Azusa; Saito, Yoshio
• Is Part Of: Tetrahedron letters. Volume 58:Issue 2(2017)
• Page Start: 117
• Page End: 120
• Publication Date: 2017-01-11
• Subjects: Nucleoside -- DNA -- Fluorescent probe -- AP site; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.11.029
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Various environmentally sensitive fluorescent (ESF) nucleosides were synthesized. These are first ESF nucleosides possessing a C2-substituted azadeazaadenine skeleton. Compound1c exhibited a remarkably high solvatochromicity (Δλ = 111 nm). 1c -containing DNA probes clearly discriminated an AP site in target DNA. Abstract: We synthesized various C2-naphthylethynylated 8-aza-7-deaza-2′-deoxyadenosines1a –1c as novel environmentally sensitive fluorescent (ESF) purine nucleosides. In particular, the N, N -dimethylamino-substituted derivative1c exhibits a remarkably high solvatochromicity (Δ λ = 111 nm).1c -containing oligodeoxynucleotide (ODN) probes clearly discriminated an apurinic/apyrimidinic site (AP site) in the complementary strand via a change in emission wavelength and intensity when hybridized with a target ODN.