Adenosine-1,3-diazaphenoxazine derivative for selective base pair formation with 8-oxo-2′-deoxyguanosine in DNA

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Abstract

The selective detection of 8-oxo-2′-deoxyguanosine (8-oxo-dG) in DNA without chemical or enzymatic treatment is an attractive tool for genomic research. We designed and synthesized the non-natural nucleoside analogue, the adenosine-1,3-diazaphenoxazine (Adap) derivative, for selective recognition of 8-oxo-dG in DNA. This study clearly showed that Adap has a highly selective stabilizing effect on the duplex containing the Adap-8-oxo-dG base pair. Furthermore, the fluorescent property of Adap was shown to be useful for the selective detection of 8-oxo-dG in the duplex DNA. To the best of our knowledge, this is the first successful demonstration of a non-natural nucleoside with a high selectivity for 8-oxo-dG in DNA.

Original languageEnglish
Pages (from-to)7272-7275
Number of pages4
JournalJournal of the American Chemical Society
Volume133
Issue number19
DOIs
Publication statusPublished - May 18 2011

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Base Pairing
Adenosine
DNA
Derivatives
Nucleosides
Demonstrations
8-oxo-7-hydrodeoxyguanosine
1,3-diazaphenoxazine
Research

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

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title = "Adenosine-1,3-diazaphenoxazine derivative for selective base pair formation with 8-oxo-2′-deoxyguanosine in DNA",
abstract = "The selective detection of 8-oxo-2′-deoxyguanosine (8-oxo-dG) in DNA without chemical or enzymatic treatment is an attractive tool for genomic research. We designed and synthesized the non-natural nucleoside analogue, the adenosine-1,3-diazaphenoxazine (Adap) derivative, for selective recognition of 8-oxo-dG in DNA. This study clearly showed that Adap has a highly selective stabilizing effect on the duplex containing the Adap-8-oxo-dG base pair. Furthermore, the fluorescent property of Adap was shown to be useful for the selective detection of 8-oxo-dG in the duplex DNA. To the best of our knowledge, this is the first successful demonstration of a non-natural nucleoside with a high selectivity for 8-oxo-dG in DNA.",
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T1 - Adenosine-1,3-diazaphenoxazine derivative for selective base pair formation with 8-oxo-2′-deoxyguanosine in DNA

AU - Taniguchi, Yosuke

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AU - Sasaki, Shigeki

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AB - The selective detection of 8-oxo-2′-deoxyguanosine (8-oxo-dG) in DNA without chemical or enzymatic treatment is an attractive tool for genomic research. We designed and synthesized the non-natural nucleoside analogue, the adenosine-1,3-diazaphenoxazine (Adap) derivative, for selective recognition of 8-oxo-dG in DNA. This study clearly showed that Adap has a highly selective stabilizing effect on the duplex containing the Adap-8-oxo-dG base pair. Furthermore, the fluorescent property of Adap was shown to be useful for the selective detection of 8-oxo-dG in the duplex DNA. To the best of our knowledge, this is the first successful demonstration of a non-natural nucleoside with a high selectivity for 8-oxo-dG in DNA.

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