title: Modification of the aromatic ring of the WNA analogues for expansion of the triplex recognition codes.
abstract: Triplex-forming oligonucleotides (TFOs) are powerful tools for genomic research. The most stable triplex is formed by the interaction between TFOs and homopurine/homopyrimidine sequences in the target duplex, but the triplex DNA is hampered by one pyrimidine base in the homopurine tract. Previously, we developed novel nucleoside analogues (WNA: W-shaped nucleoside analogues) to recognize pyrimidine/purine inversion sites (TA or CG interrupting sites) and determined two useful WNA analogues, WNA-betaT and WNA-betaC. However, subsequent study showed that the triplex formation using the WNA analogues was dependent on its neighbouring bases of the TFOs. In this study, the new WNA analogues having a different aromatic ring were synthesized to evaluate effects on sequence dependency. It has been found that o-bromo, m-bromo-, and p-cyano-substituted WNA-betaT derivatives are selective to a TA interrupting site to form triplexes with high stability in the sequences where original WNA-betaT could not recognize.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka 812-8582, Japan.
authors.forename: Yosuke
authors.initials: Y
authors.lastname: Taniguchi
authors.forename: Ayako
authors.initials: A
authors.lastname: Nakamura
authors.forename: Eriko
authors.initials: E
authors.lastname: Aoki
authors.forename: Shigeki
authors.initials: S
authors.lastname: Sasaki
mesh_terms: D004247:DNA / Q000737:chemistry*; D024202:Electrophoretic Mobility Shift Assay; D006841:Hydrocarbons, Aromatic / Q000737:chemistry; D009705:Nucleosides / Q000737:chemistry*; D009841:Oligonucleotides / Q000737:chemistry
chemical_list: D006841:Hydrocarbons, Aromatic; D009705:Nucleosides; D009841:Oligonucleotides; C051802:triplex DNA; D004247:DNA