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

Institute of Multidisciplinary Research for Advanced Materials, Tohoku University, Aoba-ku, Sendai-shi, Miyagi, Japan.

Bioorganic & medicinal chemistry letters 2010 Oct 15

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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. Copyright © 2010 Elsevier Ltd. All rights reserved.

Citation

Shuhei Imoto, Tsuneaki Hori, Shinya Hagihara, Yosuke Taniguchi, Shigeki Sasaki, Fumi Nagatsugi. Alteration of cross-linking selectivity with the 2'-OMe analogue of 2-amino-6-vinylpurine and evaluation of antisense effects. Bioorganic & medicinal chemistry letters. 2010 Oct 15;20(20):6121-4