Development of artificial aromatic nucleic acid with cell membrane permeability

具有细胞膜渗透性的人工芳香核酸的研制

• 批准号: 24659045
• 负责人: UENO Yoshihito
• 金额: $ 2.5万
• 依托单位: Gifu University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Challenging Exploratory Research
• 财政年份: 2012
• 资助国家: 日本
• 起止时间: 2012-04-01 至 2014-03-31
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/en/grant/KAKENHI-PROJECT-24659045/
• 关键词: アンチセンス核酸; 細胞膜透過性; ヌクレアーゼ耐性; RNA親和性; DNA二重鎖; RNA二重鎖; 熱力的安定性; 熱力学的安定性; ベンゼン; 二重鎖形成; 熱的安定性; 塩基識別能; 人工核酸; DNA; RNA; 核酸医薬; 遺伝子

The purpose of this study is development of artificial aromatic nucleic acid with cell membrane permeability which involves a benzene ring instead of a ribose ring. (S)-mandelic acid was used as a starting material. After esterification, iodization, reduction, and silylation, it was converted to a boronic acid derivative. Coupling reaction of it with an adenine or cytosine in the presence of cupper (II) produced adenine and cytosine analogs in good yields. It was found that the analogs reduced thermal stabilities of DNA/DNA and DNA/RNA duplexes, but the analogs possessed high base discrimination abilities.

本研究的目的是开发具有细胞膜渗透性的人工芳香核酸，其涉及苯环而不是核糖环。（S）-扁桃酸用作起始材料。经过酯化、碘化、还原和甲硅烷基化，它被转化为硼酸衍生物。它与腺嘌呤或胞嘧啶在铜（II）的存在下偶联反应产生腺嘌呤和胞嘧啶类似物在良好的产量。结果表明，这些类似物降低了DNA/DNA和DNA/RNA双链体的热稳定性，但具有较高的碱基识别能力。

项目成果

Synthesis, thermal stability and photochemical properties of DNA containing fluorescent biary-type nucleoside surrogates

含有荧光二元型核苷替代物的DNA的合成、热稳定性和光化学性质

• 发表时间: 2013
• 期刊: J. Chem. Chem. Eng.
• 作者: Iwata;M.;Ogata;A.;Ito;Y. and Ueno;Y.
• 通讯作者: Y.