Modified α–β chimeric oligoDNA bearing a multi-conjugate of 2,2-bis(hydroxymethyl)propionic acid–anthraquinone–polyamine exhibited improved and stereo-nonspecific triplex-forming ability

Azam, A.T.M. Zafrul; Moriguchi, Tomohisa; Shinozuka, Kazuo

doi:10.1039/b514325j

Cited by 7 publications

(2 citation statements)

References 23 publications

(6 reference statements)

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“…One approach is the conjugation of the intercalation moiety to TFO. − In this study, we found that the substitution of a normal nucleoside unit in the linker region of the original chimeric TFO with a multiconjugate of the non-nucleosidic unit, 2,2-bis(hydroxymethyl)propionic acid, and an intercalator-polyamine complex substantially improves the thermal stability of the resulting alternate-strand triplex. This may be due to the intercalation of the complex to the target dsDNA. , In this paper, we will describe the results of our detailed study on the triplex-forming ability of the modified complex including the triplex-stabilizing effect of the polyamine moiety connected to the intercalator and the length of the alkyl chain linking the non-nucleosidic unit and the complex, as well as the sequence-discriminating ability of the modified chimeric TFO.…”

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confidence: 99%

Stabilizing Effect of Propionic Acid Derivative of Anthraquinone–Polyamine Conjugate Incorporated into α–β Chimeric Oligonucleotides on the Alternate-Stranded Triple Helix

2011

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Two types of anthraquinone conjugates were synthesized as non-nucleosidic oligonucleotide components. These include an anthraquinone derivative conjugated with 2,2-bis(hydroxymethyl)propionic acid and an anthraquinone--polyamine derivative conjugated with 2,2-bis(hydroxymethyl)propionic acid. The conjugates were successfully incorporated into the "linking-region" of the α-β chimeric oligonucleotides via phosphoramidite method as non-nucleosidic backbone units. The resultant novel α-β chimeric oligonucleotides possessed two diastereomers that were generated by the introduction of the anthraquinone conjugate with a stereogenic carbon atom. The isomers were successfully separated by a reversed-phase HPLC. UV-melting experiments revealed that both stereoisomers formed a substantially stable alternate-strand triple helix, irrespective of the stereochemistry of the incorporated non-nucleosidic backbone unit. However, the enhancing effect on thermal stability depended on the length of the alkyl linker connecting anthraquinone moiety and the propionic acid moiety. The sequence discrimination ability of the chimeric oligonucleotides toward mismatch target duplex was also examined. The T(m) values of the triplexes containing the mismatch target were substantially lower than the T(m) values of those containing the full-match target. The thermodynamic parameters (ΔH°, ΔS°, and ΔG°) required for the dissociation of the triplexes into the third strand and target duplex were also measured.

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Section: Introductionmentioning

confidence: 99%

Stabilizing Effect of Propionic Acid Derivative of Anthraquinone–Polyamine Conjugate Incorporated into α–β Chimeric Oligonucleotides on the Alternate-Stranded Triple Helix

2011

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“…To further increase the stability of the alternating triplex, Shinozuka and co-workers developed a,b-chimeras in which the linker between the a-and the b-tracts were connected to a linker able to interfere with the unrecognized sequence of the dsDNA target. For this purpose, the intercalating agent anthraquinone was introduced into the linker at the internucleoside linkage [90], or as a conjugated nucleobase [91] or as a non-nucleosidic unit derived from 2,2-bis(hydroxymethyl)propanoic acid [92] (Fig. 9).…”

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ChemInform Abstract: From Anionic to Cationic α‐Anomeric Oligodeoxynucleotides

Morvan

Debart

2010

ChemInform

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Introduction: From b-to a-Anomery. -To obtain nuclease-resistant oligonucleotides that could be used as antisense for gene control, many modified oligonucleotides have been reported. Among them, in mid 80s oligodeoxynucleotides with an aanomeric configuration (a-ODNs) were synthesized, and their properties were evaluated (i.e., hybridization, nuclease resistance, and antisense activity). a-Anomeric nucleosides diverge from b-ones by an inversion of the configuration at C(1') anomeric position of the deoxyribofuranose ring. It was suggested on the basis of the Dreiding model study undertaken by Sequin as early as 1973 that a-ODNs could hybridize complementary b-DNA sequence but with a parallel orientation [1]. As shown in Fig. 1, b-thymidine 5'-monophosphate and a-thymidine 3'-monophosphate display the thymine base at the same place when the orientation is reversed. In this first publication, it was shown that TT dimers which exhibit one or two a-thymidines are resistant to phosphodiesterases.

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From Anionic to Cationic α‐Anomeric Oligodeoxynucleotides

Morvan

Debart

2010

Chemistry & Biodiversity

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Modified α–β chimeric oligoDNA bearing a multi-conjugate of 2,2-bis(hydroxymethyl)propionic acid–anthraquinone–polyamine exhibited improved and stereo-nonspecific triplex-forming ability

Cited by 7 publications

References 23 publications

Stabilizing Effect of Propionic Acid Derivative of Anthraquinone–Polyamine Conjugate Incorporated into α–β Chimeric Oligonucleotides on the Alternate-Stranded Triple Helix

Stabilizing Effect of Propionic Acid Derivative of Anthraquinone–Polyamine Conjugate Incorporated into α–β Chimeric Oligonucleotides on the Alternate-Stranded Triple Helix

ChemInform Abstract: From Anionic to Cationic α‐Anomeric Oligodeoxynucleotides

From Anionic to Cationic α‐Anomeric Oligodeoxynucleotides

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