OFF-to-ON type fluorescent probe for the detection of 8-oxo-dG in DNA by the Adap-masked ODN probe

Yosuke Taniguchi, Yohei Koga, Keitaro Fukabori, Ryota Kawaguchi, Shigeki Sasaki

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

We have recently reported that Adap (adenosine-1,3-diazaphenoxazine) is an artificial nucleoside analogue for the specific recognition by multiple hydrogen bonding and that its fluorescence is selectively quenched with 8-oxo-2′-deoxyguanosine (8-oxo-dG) in DNA. We now report the development of a new OFF-to-ON type FRET probe, in which one strand contains Adap and another contains natural nucleotides for the formation of a less stable double strand. Each strand was labeled with Cy3 or BHQ2 at the 5′-end or 3′-end, respectively. It was expected in this system that fluorescence of the duplex probe is first quenched by FRET, but the target DNA strand containing 8-oxo-dG at the complementary site of Adap would enhance the displacement reaction of the less stable duplex probe that results in the fluorescence recovery. The results showed that the duplex probe containing the Adap-T base pair exhibited a complete discrimination between 8-oxo-dG and dG in DNA by fluorescence enhancement.

Original languageEnglish
Pages (from-to)543-546
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume22
Issue number1
DOIs
Publication statusPublished - Jan 1 2012

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Fluorescent Dyes
Adenosine
Fluorescence
DNA
Hydrogen Bonding
Nucleosides
Base Pairing
Hydrogen bonds
Nucleotides
Recovery
8-oxo-7-hydrodeoxyguanosine
1,3-diazaphenoxazine

All Science Journal Classification (ASJC) codes

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

Cite this

OFF-to-ON type fluorescent probe for the detection of 8-oxo-dG in DNA by the Adap-masked ODN probe. / Taniguchi, Yosuke; Koga, Yohei; Fukabori, Keitaro; Kawaguchi, Ryota; Sasaki, Shigeki.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 22, No. 1, 01.01.2012, p. 543-546.

Research output: Contribution to journalArticle

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