Synthesis of ethynylpyrene-modified 3-deaza-2′-deoxyguanosines as environmentally sensitive fluorescent nucleosides: Target DNA-sequence detection via changes in the fluorescence wavelength. Issue 12 (21st March 2019)

• Record Type: Journal Article
• Authors: Takeda, Takuya; Yanagi, Masaki; Suzuki, Azusa; Katoh, Ryuzi; Saito, Yoshio
• Is Part Of: Tetrahedron letters. Volume 60:Issue 12(2019)
• Page Start: 825
• Page End: 830
• Publication Date: 2019-03-21
• Subjects: Nucleoside -- DNA -- Fluorescent probe -- 3-Deazaguanine; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2019.02.002
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlight: Pyrene-labeled ESF nucleosides possessing the 3-deazaG skeleton were synthesized. 1p3z G showed remarkable solvent-polarity-sensitive fluorescence properties. ODN probes containing 1p3z G clearly discriminated target DNAs. Abstract: Novel pyrene-labeled environmentally sensitive fluorescent (ESF) nucleosides [ 1p3z G (1a ) and 2p3z G (1b )] possessing the 3-deazaguanine skeleton were synthesized. Among them, 1p3z G (1a) exhibited longer fluorescence emission wavelengths compared with the previously reported naphthalene-modified ESF nucleoside 3nz G (48–71 nm longer in polar solvents) and showed remarkable solvent-polarity-sensitive fluorescence properties. Oligodeoxynucleotide (ODN) probes containing 1p3z G (1a) clearly discriminated target DNAs by the change in the emission wavelength and intensity through monitoring the microenvironmental change around the DNA minor groove. Thus, these pyrene-labeled ESF nucleosides can be applied in gene detection and molecular diagnostics, as well as in the structural analysis of nucleic acids.