Synthesis and thermal stabilities of oligonucleotides containing 2′-O,4′-C-methylene bridged nucleic acid with a phenoxazine base

Yuki Kishimoto; Akane Fujii; Osamu Nakagawa; Tetsuya Nagata; Takanori Yokota; Yoshiyuki Hari; Satoshi Obika

doi:10.1039/C7OB01874F

Synthesis and thermal stabilities of oligonucleotides containing 2′-O,4′-C-methylene bridged nucleic acid with a phenoxazine base†

Yuki Kishimoto,

^ab Akane Fujii,

^ab Osamu Nakagawa,

*^ab Tetsuya Nagata,

^bc Takanori Yokota,

^bc Yoshiyuki Hari

^d and Satoshi Obika

*^ab

Author affiliations

* Corresponding authors

^a Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan
E-mail: obika@phs.osaka-u.ac.jp, osamu_nakagawa@phs.osaka-u.ac.jp

^b Core Research for Evolutional Science and Technology (CREST), Japan Sciences and Technology Agency (JST), 7 Gobancho, Chiyoda-ku, Tokyo 102-0076, Japan

^c Department of Neurology and Neurological Science, Graduate School of Medical and Dental Sciences, Tokyo Medical and Dental University, 1-5-45 Yushima, Bunkyo-ku, Tokyo 113-8519, Japan

^d Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Nishihama, Yamashiro-cho, Tokushima 770-8514, Japan

Abstract

We designed and synthesized a novel artificial 2′-O,4′-C-methylene bridged nucleic acid (2′,4′-BNA/LNA) with a phenoxazine nucleobase and named this compound BNAP. Oligodeoxynucleotide (ODN) containing BNAP showed higher binding affinities toward complementary DNA and RNA as compared to ODNs bearing 2′,4′-BNA/LNA with 5-methylcytosine or 2′-deoxyribonucleoside with phenoxazine. Thermodynamic analysis revealed that BNAP exhibits properties associated with the phenoxazine moiety in DNA/DNA duplexes and characteristics associated with the 2′,4′-BNA/LNA moiety in DNA/RNA duplexes.

This article is part of the themed collection: Nucleic Acid Modifications

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Article information

https://doi.org/10.1039/C7OB01874F

Submitted

28 Jul 2017

Accepted

06 Sep 2017

First published

14 Sep 2017

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Org. Biomol. Chem., 2017,15, 8145-8152

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Synthesis and thermal stabilities of oligonucleotides containing 2′-O,4′-C-methylene bridged nucleic acid with a phenoxazine base

Y. Kishimoto, A. Fujii, O. Nakagawa, T. Nagata, T. Yokota, Y. Hari and S. Obika, Org. Biomol. Chem., 2017, 15, 8145

DOI: 10.1039/C7OB01874F

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Organic & Biomolecular Chemistry

Synthesis and thermal stabilities of oligonucleotides containing 2′-O,4′-C-methylene bridged nucleic acid with a phenoxazine base†

Abstract

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Synthesis and thermal stabilities of oligonucleotides containing 2′-O,4′-C-methylene bridged nucleic acid with a phenoxazine base

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