含 vinylnaphthalene 的六噁唑作为荧光开启型 G-四链体配体。

Vinylnaphthalene-bearing hexaoxazole as a fluorescence turn-on type G-quadruplex ligand.

机构信息

Institute of Global Innovation Research, Tokyo University of Agriculture and Technology, 2-24-16 Naka-cho, Koganei, To-kyo 184-8588, Japan.

Department of Biotechnology and Life Science, Tokyo University of Agriculture and Technology, 2-24-16 Naka-cho, Ko-ganei, Tokyo 184-8588, Japan.

出版信息

Org Biomol Chem. 2021 Sep 29;19(37):8035-8040. doi: 10.1039/d1ob01500a.

Abstract

Oxazole-type fluorophores show an increase of fluorescence intensity upon interaction with nucleic acids, and therefore can be used as tools for nucleic acid-sensing and fluorescence imaging. Here, we developed a novel stilbene-type fluorophore, MO-VN (1), consisting of a mono oxazole bearing a vinyl naphthalene moiety. This compound (1) was embedded in a trioxazole 2 and a cyclic hexaoxazole 3a. The fluorescence properties of 1, 2, and 3a were evaluated in the presence of various nucleic acid sequences. Compound 3 showed significant fluorescent enhancement upon interacting with G-quadruplex (G4) structure, which plays critical roles in various biological phenomena. Further structural development focusing on the vinyl naphthalene moiety of 3a afforded a turn-on type G4 ligand 3e that shows G4-specific fluorescence. Measurement of the fluorescence of 3e during titration of a telomeric DNA, telo24, with its C-rich complementary sequence, which unwinds the G4 structure, allowed us to monitor the dynamics of G4.

摘要

恶唑型荧光团与核酸相互作用时荧光强度增加,因此可用作核酸传感和荧光成像的工具。在这里,我们开发了一种新型的二苯乙烯型荧光团 MO-VN(1),由一个带有乙烯基萘部分的单恶唑组成。该化合物(1)被嵌入三唑 2 和环六氧杂环 3a 中。在存在各种核酸序列的情况下,评估了 1、2 和 3a 的荧光性质。化合物 3 与 G-四链体(G4)结构相互作用时表现出显著的荧光增强,G4 在各种生物现象中起着关键作用。进一步集中研究 3a 中乙烯基萘部分的结构开发得到了一种开启型 G4 配体 3e,它显示出 G4 特异性荧光。在与富含 C 的互补序列 telo24 滴定端粒 DNA 期间测量 3e 的荧光,该序列解开 G4 结构,使我们能够监测 G4 的动态。

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