title: Development of a new dumbbell-shaped decoy DNA using a combination of the unnatural base pair ImO(N):NaN(O) and a CuAAC reaction.
abstract: We describe the synthesis and potential application of a new dumbbell-shaped decoy DNA prepared using a combination of the base pair ImO(N):NaN(O) and a copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction. The CuAAC reaction between the azido group on the 5'-end of oligodeoxynucleotide (ODN) and the ethynyl group on the NaN(O) base of the opposite strand did not proceed, whereas that between the azido group and the flexible hexynyl group on the NaN(O) base of the opposite strand proceeded smoothly to give a new dumbbell-shaped double-stranded ODN (dsODN). The resulting dsODN had extremely high thermal stability and exhibited exonuclease resistance. In addition, the terminal modification did not affect its helical structure, and thus, the dumbbell-shaped dsODN displayed promising in vitro activity in a competition assay with the NF-kB p50 transcription factor homodimer.
authors: Graduate School of Pharmaceutical Sciences, The University of Tokushima , Shomachi 1-78-1, Tokushima 770-8505, Japan.
authors: Yosuke
authors: Y
authors: Higuchi
authors: Kazuhiro
authors: K
authors: Furukawa
authors: Tadashi
authors: T
authors: Miyazawa
authors: Noriaki
authors: N
authors: Minakawa
mesh_terms: D000480:Alkynes / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D020029:Base Pairing; D001667:Binding, Competitive; D003300:Copper / Q000378:metabolism; D004247:DNA / Q000737:chemistry* / Q000378:metabolism*; D003851:Deoxyribonucleases / Q000378:metabolism; D006801:Humans; D016328:NF-kappa B / Q000037:antagonists & inhibitors* / Q000378:metabolism*; D009838:Oligodeoxyribonucleotides / Q000737:chemistry* / Q000378:metabolism
chemical_list: D000480:Alkynes; D001386:Azides; D016328:NF-kappa B; C468119:NF-kappaB decoy; D009838:Oligodeoxyribonucleotides; D003300:Copper; D004247:DNA; D003851:Deoxyribonucleases