Alteration of cross-linking selectivity with the 2′-OMe analogue of 2-amino-6-vinylpurine and evaluation of antisense effects

Shuhei Imoto; Tsuneaki Hori; Shinya Hagihara; Yosuke Taniguchi; Shigeki Sasaki; Fumi Nagatsugi

doi:10.1016/j.bmcl.2010.08.027

Alteration of cross-linking selectivity with the 2′-OMe analogue of 2-amino-6-vinylpurine and evaluation of antisense effects

Shuhei Imoto, Tsuneaki Hori, Shinya Hagihara, Yosuke Taniguchi, Shigeki Sasaki, Fumi Nagatsugi

Chemo-Pharmaceutical Sciences

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

21 Citations (Scopus)

Abstract

We previously reported that oligodeoxynucleotides containing 2-amino-6-vinylpurine (2-AVP: 1) exhibit efficient selective cross-linking to cytosine. In this study, the 2′-OMe nucleoside analogue (2) of 2-AVP was designed in order to increase its affinity to RNA and enhance metabolic stability. It has been demonstrated that 2′-OMe oligonucleotides bearing 2 achieve highly selective cross-linking to the thymine base in DNA and show higher antisense effect on luciferase production in cell lysate.

Original language	English
Pages (from-to)	6121-6124
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	20
Issue number	20
DOIs	https://doi.org/10.1016/j.bmcl.2010.08.027
Publication status	Published - Oct 1 2010

All Science Journal Classification (ASJC) codes

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

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Alteration of cross-linking selectivity with the 2′-OMe analogue of 2-amino-6-vinylpurine and evaluation of antisense effects. / Imoto, Shuhei; Hori, Tsuneaki; Hagihara, Shinya; Taniguchi, Yosuke; Sasaki, Shigeki; Nagatsugi, Fumi.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 20, No. 20, 01.10.2010, p. 6121-6124.

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

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