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Twisted intercalating nucleic acid
Twisted intercalating nucleic acid (TINA) is a nucleic acid molecule that, when added to triplex-forming oligonucleotides (TFOs), stabilize Hoogsteen triplex DNA formation from double-stranded DNA (dsDNA) and TFOs.〔Geci, I, VV Filichev, and EB Pedersen. “Stabilization of parallel triplexes by twisted intercalating nucleic acids (TINAs) incorporating 1,2,3-triazole units and prepared by microwave-accelerated click chemistry.” Chemistry. 13. no. 22 (2007): 6379-386.〕 Its ability to twist around a triple bond increases ease of intercalation within double stranded DNA in order to form triplex DNA. Certain configurations have been shown to stabilize Watson-Crick antiparallel duplex DNA. TINA-DNA primers have been shown to increase the specificity of binding in PCR. The use of TINA insertions in G-quadruplexes has also been shown to enhance anti-HIV-1 activity. TINA stabilized PT demonstrates improved sensitivity and specificity of DNA based clinical diagnostic assays.
== Triplex DNA ==
Triple helixes are formed when a single-stranded triplex-forming oligonucleotide (TFO) binds to a purine-containing strand of dsDNA through specific major groove interactions.〔Geci, VV Filichev, and EB Pedersen. “Synthesis of Twisted Intercalating Nucleic Acids Possessing Acridine Derivatives. Thermal Stability Studies.” Bioconjugate Chem. 17. no. 4 (2006): 950-957.〕 Generally, the third-strand affinity of a TFO is low, due to the requirement for the formation of pH-sensitive C+–G–C Hoogsteen base triplexes under physiological conditions in the parallel (pyrimidine) binding motif. Modification of TFOs has been attempted in order to improve their binding affinities to their targets and to lessen restrictions in the dsDNA sequence with the design of new triplex nucleobases. Recently, it has been found that bulge insertions of (R)-1-O-()glycerol (TINA) into the middle of homopyrimidine oligodeoxynucleotides can give rise to thermal stability in Hoogsteen-type triplexes and duplexes, whereas Watson–Crick-type duplexes of the same nucleotide content were destabilized.〔Filichev VV, Pedersen EB. Stable and selective formation of hoogsteen-type triplexes and duplexes using twisted intercalating nucleic acids (TINA) prepared via postsynthetic Sonogashira solid-phase coupling reactions. J Am Chem Soc.127. no. 42 (2005):148-58.〕 To increase ∆Tm, base mismatches should be placed in the center of the TFO and when feasible, A, C or T to G base mismatches should be avoided. Base mismatches can be neutralized by intercalation of a TINA on each side of the base mismatch and masked by a TINA intercalating direct 3'or 5' of it.
抄文引用元・出典: フリー百科事典『 ウィキペディア（Wikipedia）』
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