2,6-Diaminopurine nucleoside derivative of 9-ethyloxy-2-oxo-1,3- diazaphenoxazine (2-amino-Adap) for recognition of 8-oxo-dG in DNA

Yosuke Taniguchi, Keitaro Fukabori, Yoshiya Kikukawa, Yohei Koga, Shigeki Sasaki

研究成果: ジャーナルへの寄稿記事

10 引用 (Scopus)

抄録

8-Oxo-2′-deoxyguanosine (8-oxo-dG) is a nucleoside resulting from oxidative damage and is known to be mutagenic. 8-Oxo-dG has been related to aging and diseases, including neurological disorders and cancer. Recently, we reported that a fluorescent nucleoside derivative, adenosine-1,3- diazaphenoxazine (Adap), forms a stable base pair with 8-oxo-dG in DNA with accompanying efficient quenching. In this study, a new Adap derivative having an additional 2-amino group on the adenosine moiety (2-amino-Adap) was designed with the anticipation of additional hydrogen bonding with the 8-oxo group of 8-oxo-dG. The properties of the ODN containing 2-amino-Adap were evaluated by measuring thermal stability and fluorescence quenching. In contrast to the previously designed Adap, the base-pairing and fluorescence quenching properties of 2-amino-Adap varied depending on the ODN sequence, and there was no clear indication of an additional hydrogen bond with 8-oxo-dG. Instead, the base pairing of 2-amino-Adap with dG was significantly destabilized compared with that of Adap with dG, resulting in improved selectivity for 8-oxo-dG in the human telomere DNA sequence. Thus, the telomere-targeting ODN probe containing 2-amino-Adap displayed selective, sensitive and quantitative detection of 8-oxo-dG in the human telomere DNA sequence in a light-up detection system using SYBR Green.

元の言語英語
ページ(範囲)1634-1641
ページ数8
ジャーナルBioorganic and Medicinal Chemistry
22
発行部数5
DOI
出版物ステータス出版済み - 3 1 2014

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Nucleosides
Adenosine
Derivatives
DNA
Telomere
Base Pairing
Quenching
DNA sequences
Hydrogen bonds
Fluorescence
8-oxo-7-hydrodeoxyguanosine
1,3-diazaphenoxazine
2,6-diaminopurine
Hydrogen Bonding
Nervous System Diseases
Hydrogen
Thermodynamic stability
Hot Temperature
Aging of materials
Light

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

これを引用

2,6-Diaminopurine nucleoside derivative of 9-ethyloxy-2-oxo-1,3- diazaphenoxazine (2-amino-Adap) for recognition of 8-oxo-dG in DNA. / Taniguchi, Yosuke; Fukabori, Keitaro; Kikukawa, Yoshiya; Koga, Yohei; Sasaki, Shigeki.

:: Bioorganic and Medicinal Chemistry, 巻 22, 番号 5, 01.03.2014, p. 1634-1641.

研究成果: ジャーナルへの寄稿記事

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abstract = "8-Oxo-2′-deoxyguanosine (8-oxo-dG) is a nucleoside resulting from oxidative damage and is known to be mutagenic. 8-Oxo-dG has been related to aging and diseases, including neurological disorders and cancer. Recently, we reported that a fluorescent nucleoside derivative, adenosine-1,3- diazaphenoxazine (Adap), forms a stable base pair with 8-oxo-dG in DNA with accompanying efficient quenching. In this study, a new Adap derivative having an additional 2-amino group on the adenosine moiety (2-amino-Adap) was designed with the anticipation of additional hydrogen bonding with the 8-oxo group of 8-oxo-dG. The properties of the ODN containing 2-amino-Adap were evaluated by measuring thermal stability and fluorescence quenching. In contrast to the previously designed Adap, the base-pairing and fluorescence quenching properties of 2-amino-Adap varied depending on the ODN sequence, and there was no clear indication of an additional hydrogen bond with 8-oxo-dG. Instead, the base pairing of 2-amino-Adap with dG was significantly destabilized compared with that of Adap with dG, resulting in improved selectivity for 8-oxo-dG in the human telomere DNA sequence. Thus, the telomere-targeting ODN probe containing 2-amino-Adap displayed selective, sensitive and quantitative detection of 8-oxo-dG in the human telomere DNA sequence in a light-up detection system using SYBR Green.",
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T1 - 2,6-Diaminopurine nucleoside derivative of 9-ethyloxy-2-oxo-1,3- diazaphenoxazine (2-amino-Adap) for recognition of 8-oxo-dG in DNA

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AU - Sasaki, Shigeki

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AB - 8-Oxo-2′-deoxyguanosine (8-oxo-dG) is a nucleoside resulting from oxidative damage and is known to be mutagenic. 8-Oxo-dG has been related to aging and diseases, including neurological disorders and cancer. Recently, we reported that a fluorescent nucleoside derivative, adenosine-1,3- diazaphenoxazine (Adap), forms a stable base pair with 8-oxo-dG in DNA with accompanying efficient quenching. In this study, a new Adap derivative having an additional 2-amino group on the adenosine moiety (2-amino-Adap) was designed with the anticipation of additional hydrogen bonding with the 8-oxo group of 8-oxo-dG. The properties of the ODN containing 2-amino-Adap were evaluated by measuring thermal stability and fluorescence quenching. In contrast to the previously designed Adap, the base-pairing and fluorescence quenching properties of 2-amino-Adap varied depending on the ODN sequence, and there was no clear indication of an additional hydrogen bond with 8-oxo-dG. Instead, the base pairing of 2-amino-Adap with dG was significantly destabilized compared with that of Adap with dG, resulting in improved selectivity for 8-oxo-dG in the human telomere DNA sequence. Thus, the telomere-targeting ODN probe containing 2-amino-Adap displayed selective, sensitive and quantitative detection of 8-oxo-dG in the human telomere DNA sequence in a light-up detection system using SYBR Green.

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