Enhanced duplex- and triplex-forming ability and enzymatic resistance of oligodeoxynucleotides modified by a tricyclic thymine derivative,Organic & Biomolecular Chemistry

当前位置： X-MOL 学术 › Org. Biomol. Chem. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Enhanced duplex- and triplex-forming ability and enzymatic resistance of oligodeoxynucleotides modified by a tricyclic thymine derivative
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2021-08-31 , DOI: 10.1039/d1ob01462e
Yuki Kishimoto _{1,

2} , Akane Fujii _{1,

2} , Osamu Nakagawa _{1,

2,

3} , Satoshi Obika _{1,

2}

Affiliation

We designed and synthesized an artificial nucleic acid, [3-(1,2-dihydro-2-oxobenzo[b][1,8]naphthyridine)]-2′-deoxy-D-ribofuranose (OBN), with a tricyclic structure in a nucleobase as a thymidine analog. Oligodeoxynucleotides (ODNs) containing consecutive OBN displayed improved duplex-forming ability with complementary single-stranded (ss) RNA and triplex-forming ability with double-stranded DNA in comparison with ODNs composed of natural thymidine. OBN-modified ODNs also displayed enhanced enzymatic resistance compared with ODNs with natural thymidine and phosphorothioate modification, respectively, due to the structural steric hindrance of the nucleobase. The fluorescence spectra of OBN-modified ODNs showed sufficient fluorescence intensity with ssDNA and ssRNA, which is an advantageous feature for fluorescence imaging techniques of nucleic acids with longer emission wavelengths than bicyclic thymine (bT).

中文翻译：

三环胸腺嘧啶衍生物修饰的寡脱氧核苷酸增强双链体和三链体形成能力和酶抗性

我们设计并合成了具有三环结构的人工核酸[3-(1,2-二氢-2-氧代苯并[ b ][1,8]萘啶)]-2′-脱氧-D-呋喃核糖(OBN)在核碱基中作为胸苷类似物。与由天然胸苷组成的 ODN 相比，含有连续 OBN 的寡脱氧核苷酸 (ODN) 显示出改善的与互补单链 (ss) RNA 的双链体形成能力和与双链 DNA 的三链体形成能力。由于核碱基的结构空间位阻，与分别具有天然胸苷和硫代磷酸酯修饰的 ODN 相比，OBN 修饰的 ODN 还表现出增强的酶抗性。 OBN 修饰的 ODN 的荧光光谱显示出足够的 ssDNA 和 ssRNA 荧光强度，这对于发射波长比双环胸腺嘧啶 (bT) 更长的核酸荧光成像技术来说是一个有利的特征。

更新日期：2021-09-08

点击分享查看原文

点击收藏

阅读更多本刊最新论文本刊介绍/投稿指南11