914675-30-2Relevant academic research and scientific papers
Twisted intercalating nucleic acids - Intercalator influence on parallel triplex stabilities
Filichev, Vyacheslav V.,Gaber, Hatem,Olsen, Thomas R.,Jorgensen, Per T.,Jessen, Carsten H.,Pedersen, Erik B.
, p. 3960 - 3968 (2007/10/03)
Phosphoramidites of several new twisted intercalating nucleic acid (TINA) monomers and the previously discovered (R)-1-O-[4-(1-pyrenylethynyl) phenylmethyl]glycerol (1) were synthesized and used in DNA synthesis. Stabilization of Hoogsteen-type triplexes was observed in cases of insertion of the novel (R)-1-O-[3-(naphthalen-1-ylethynyl)phenylmethyl]glycerol (2) as a bulge into homopyrimidine oligodeoxynucleotides (ONs), whereas phenylethynyl and 4-(biphenylylethynyl) derivatives of TINAs resulted in destabilization of parallel triplexes relative to the wild-type triplex. It was concluded that TINA monomers should possess at least two fused phenyl rings attached through the triple bond at the 4-position of bulged (R)-1-O-(phenylmethyl)glycerol in homopyrimidine ONs in order to stabilize parallel triplexes. Slight destabilization of DNA/DNA Watson-Crick type duplexes (ΔTm = 1.0-4.5°C) was detected for 2 inserted as a bulge, while RNA/DNA duplexes and duplexes with other TINA analogues were considerably destabilized (ΔTm > 6.0°C). In cases of double insertion of 1 opposite to base inversions in dsDNA, the thermal stabilities of the triplexes were higher than that of the wild-type triplex, which is a new solution to overcome the problem of targeting homopurine stretches with single base pair inversions. A DNA three-way junction was considerably stabilized (ΔT m in a range of 10.0-15.5°C) upon insertion of TINA monomers in the junction point as a bulge. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
