Triplex formation of oligonucleotides containing 2'-O-methylpseudoisocytidine in substitution for 2'-deoxycytidine

Ono, Akira; Ts’o, Paul O. P.; Kan, Lou Sing

doi:10.1021/ja00010a077

Cited by 165 publications

(119 citation statements)

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“…N-(2-Boc-aminoethyl)-N-(N2-(Benzyloxycarbonyl)isocytosin-5-ylacetyl)glycine (12). Ethyl N-(2-Boc-aminoethyl)-N-(N2-(benzyloxycarbonyl)isocytosin-5-ylacetyl)glycinate ( …”

Section: Ih-nmr (Dmso-dw/msunclassified

Efficient pH-independent sequence-specific DNA binding by pseudoisocytosine-containing bis-PNA

Egholm¹,

Christensen²,

Dueholm³

et al. 1995

Nucl Acids Res

302

277

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The synthesis and DNA binding properties of bis-PNA (peptide nucleic acid) are reported. Two PNA segments each of seven nucleobases in length were connected in a continuous synthesis via a flexible linker composed of three 8-amino-3,6-dioxaoctanoic acid units. The sequence of the first strand was TCTCTTT (C-to N-terminal), while the second strand was TTTCTCT or TTTJTJT, where J is pseudoisocytosine. These bisPNAs form triple-stranded complexes of somewhat higher thermal stability than monomeric PNA with complementary oligonucleotides and the thermal melting transition shows very little hysteresis. When the J base is placed in the strand parallel to the DNA complement ('Hoogsteen strand'), the DNA binding was pH independent. The bis-PNAs were also superior to monomeric PNAs for targeting double-stranded DNA by strand invasion.

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“…N-(2-Boc-aminoethyl)-N-(N2-(Benzyloxycarbonyl)isocytosin-5-ylacetyl)glycine (12). Ethyl N-(2-Boc-aminoethyl)-N-(N2-(benzyloxycarbonyl)isocytosin-5-ylacetyl)glycinate ( …”

Section: Ih-nmr (Dmso-dw/msunclassified

Efficient pH-independent sequence-specific DNA binding by pseudoisocytosine-containing bis-PNA

Egholm¹,

Christensen²,

Dueholm³

et al. 1995

Nucl Acids Res

302

277

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“…Binding results in the formation of hydrogen-bonded T.AT and C+.GC triplets in which pyrimidines in the thirdstrand are Hoogesteen-bound to the purines of the DNA duplex [1][2][3]. Several researclaers have used DNA triplexes including modified bases and phosphate groups on the third strand in order to develop highly selective drugs [4][5][6][7][8][9][10][11][12]. We report the effect of phosphorothioate substitution on the conformation of a triplex of DNA.…”

Section: Introductionmentioning

confidence: 99%

The influence of oligodeoxyribonucleotide phosphorothioate pyrimidine strands on triplex formation

et al. 1992

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Analogues of the homopyrimidine oiigonucleotide dT,s that contained phosphorothioat¢ bonds of a mixture ofdiastereoisomers or one of tile two stereoisomers (either Rp or Sp) were synthesized. The analogues were mixed under eondition~ conducive to the formation of tripl¢.-.atranded assemblies. The mixtures were characterized by their thermal stabilities (7"1,, values), CD spectra, and gel electropltoresis pattern. The 34-met duplexes containing 15 central purines on one strand attd 15 complementary pyrimidines on the other strand gave no detectable triple helix upon combination with dTt~S~. On the other hand, 34-bp duplexes with dT~sS,, having Rp or Sp, formed triple helix~. This suggests that a sterie factor plays an important role in triple helix formation.

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“…However, TFOs containing iCm could not stabilize the triplex structure sufficiently at neutral pH. 10,11 On the other hand, we have recently reported that TFOs containing 2 0 -O-methyl-2-thiouridine (s 2 Um) or 2-thiothymidine (s 2 T) formed quite stable parallel triplex structures. 16 Enhancement of the thermal stability of these parallel triplexes can be explained by means of the strong stacking interaction of the 2-thiocarbonyl group with the 5 0 -upstream or 3 0 -downstream bases.…”

Section: -15mentioning

confidence: 99%

Synthesis of 4-Thiopseudoisocytidine and 4-Thiopseudouridine as Components of Triplex-forming Oligonucleotides

Okamoto¹,

Cao²,

Tanaka³

et al. 2009

Chemistry Letters

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In this paper, we report convenient methods for the synthesis of 4-thiopseudoisocytidine (s 4 iC) and 4-thiopseudouridine (s 4 É). 1 H NMR spectral analysis of these modified nucleosides showed that both s 4 É and s 4 iC prefer C3 0 -endo ribose puckering. These conformational properties are favorable for the stabilization of triplex formation.Using the antigene strategy, a large number of modified nucleosides have been synthesized to enhance the thermal stability of DNA triplexes formed by hybridization of the third DNA strands with DNA duplexes.

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Triplex formation of oligonucleotides containing 2'-O-methylpseudoisocytidine in substitution for 2'-deoxycytidine

Cited by 165 publications

References 1 publication

Efficient pH-independent sequence-specific DNA binding by pseudoisocytosine-containing bis-PNA

Efficient pH-independent sequence-specific DNA binding by pseudoisocytosine-containing bis-PNA

The influence of oligodeoxyribonucleotide phosphorothioate pyrimidine strands on triplex formation

Synthesis of 4-Thiopseudoisocytidine and 4-Thiopseudouridine as Components of Triplex-forming Oligonucleotides

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