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

IMRAM - Division of Organic- and Biomaterials Research

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

24 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 - 2010 Oct

Keywords

Antisense
Cross-linking
DNA
Nucleic acids chemistry
Oligonucleotide

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10.1016/j.bmcl.2010.08.027

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

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.",

keywords = "Antisense, Cross-linking, DNA, Nucleic acids chemistry, Oligonucleotide",

author = "Shuhei Imoto and Tsuneaki Hori and Shinya Hagihara and Yosuke Taniguchi and Shigeki Sasaki and Fumi Nagatsugi",

note = "Funding Information: The authors are grateful for the support offered by Grant-in-Aid for Scientific Research (B) from Japan Society for the promotion of Science and CREST from Japan Science and Technology Agency . ",

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T1 - Alteration of cross-linking selectivity with the 2′-OMe analogue of 2-amino-6-vinylpurine and evaluation of antisense effects

AU - Imoto, Shuhei

AU - Hori, Tsuneaki

AU - Hagihara, Shinya

AU - Taniguchi, Yosuke

AU - Sasaki, Shigeki

AU - Nagatsugi, Fumi

N1 - Funding Information: The authors are grateful for the support offered by Grant-in-Aid for Scientific Research (B) from Japan Society for the promotion of Science and CREST from Japan Science and Technology Agency .

PY - 2010/10

Y1 - 2010/10

N2 - 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.

AB - 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.

KW - Antisense

KW - Cross-linking

KW - DNA

KW - Nucleic acids chemistry

KW - Oligonucleotide

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

Abstract

Keywords

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