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

Yosuke Taniguchi; Ryota Kawaguchi; Shigeki Sasaki

doi:10.1021/ja200327u

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

Yosuke Taniguchi, Ryota Kawaguchi, Shigeki Sasaki

Chemo-Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

40 Citations (Scopus)

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 language	English
Pages (from-to)	7272-7275
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	133
Issue number	19
DOIs	https://doi.org/10.1021/ja200327u
Publication status	Published - May 18 2011

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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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.",

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

Abstract

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