| Double-stranded DNA-templated cleavage of oligonucleotides containing a P3'->N5' linkage triggered by triplex formation: the effects of chemical modifications and remarkable enhancement in reactivity. | |
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MedLine Citation:
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PMID: 20615902 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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We recently reported double-stranded DNA-templated cleavage of oligonucleotides as a sequence-specific DNA-detecting method. In this method, triplex-forming oligonucleotides (TFOs) modified with 5'-amino-2',4'-BNA were used as a DNA-detecting probe. This modification introduced a P3'→N5' linkage (P-N linkage) in the backbone of the TFO, which was quickly cleaved under acidic conditions when it formed a triplex. The prompt fission of the P-N linkage was assumed to be driven by a conformational strain placed on the linkage upon triplex formation. Therefore, chemical modifications around the P-N linkage should change the reactivity by altering the microenvironment. We synthesized 5'-aminomethyl type nucleic acids, and incorporated them into TFOs instead of 5'-amino-2',4'-BNA to investigate the effect of 5'-elongation. In addition, 2',4'-BNA/LNA or 2',5'-linked DNA were introduced at the 3'- and/or 5'-neighboring residues of 5'-amino-2',4'-BNA to reveal neighboring residual effects. We evaluated the triplex stability and reaction properties of these TFOs, and found out that chemical modifications around the P-N linkage greatly affected their reaction properties. Notably, 2',5'-linked DNA at the 3' position flanking 5'-amino-2',4'-BNA brought significantly higher reactivity, and we succeeded in indicating that a TFO with this modification is promising as a DNA analysis tool. |
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Authors:
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Kosuke Ramon Ito; Tetsuya Kodama; Masaharu Tomizu; Yoshinori Negoro; Ayako Orita; Tomohisa Osaki; Noritsugu Hosoki; Takaya Tanaka; Takeshi Imanishi; Satoshi Obika |
Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't Date: 2010-07-08 |
Journal Detail:
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Title: Nucleic acids research Volume: 38 ISSN: 1362-4962 ISO Abbreviation: Nucleic Acids Res. Publication Date: 2010 Nov |
Date Detail:
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Created Date: 2010-11-12 Completed Date: 2011-01-04 Revised Date: 2013-05-29 |
Medline Journal Info:
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Nlm Unique ID: 0411011 Medline TA: Nucleic Acids Res Country: England |
Other Details:
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Languages: eng Pagination: 7332-42 Citation Subset: IM |
Affiliation:
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Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Base Pair Mismatch Bridged Compounds / chemistry DNA / chemical synthesis, chemistry* Hydrogen-Ion Concentration Nitrogen / chemistry Nucleic Acids / chemical synthesis, chemistry Phosphates / chemistry Sequence Analysis, DNA* |
| Chemical | |
Reg. No./Substance:
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0/Bridged Compounds; 0/Nucleic Acids; 0/Phosphates; 0/triplex DNA; 7727-37-9/Nitrogen; 9007-49-2/DNA |
| Comments/Corrections | |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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