A Multicolor Large Stokes Shift Fluorogen‐Activating RNA Aptamer with Cationic Chromophores,Chemistry - A European Journal

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A Multicolor Large Stokes Shift Fluorogen‐Activating RNA Aptamer with Cationic Chromophores
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2019-01-11 , DOI: 10.1002/chem.201805882
Christian Steinmetzger ₁ , Navaneethan Palanisamy _{2,

3} , Kiran R. Gore _{4,

5} , Claudia Höbartner _{1,

2,

4}

Affiliation

Large Stokes shift (LSS) fluorescent proteins (FPs) exploit excited state proton transfer pathways to enable fluorescence emission from the phenolate intermediate of their internal 4‐hydroxybenzylidene imidazolone (HBI) chromophore. An RNA aptamer named Chili mimics LSS FPs by inducing highly Stokes‐shifted emission from several new green and red HBI analogues that are non‐fluorescent when free in solution. The ligands are bound by the RNA in their protonated phenol form and feature a cationic aromatic side chain for increased RNA affinity and reduced magnesium dependence. In combination with oxidative functionalization at the C2 position of the imidazolone, this strategy yielded DMHBO⁺, which binds to the Chili aptamer with a low‐nanomolar K_D. Because of its highly red‐shifted fluorescence emission at 592 nm, the Chili–DMHBO⁺ complex is an ideal fluorescence donor for Förster resonance energy transfer (FRET) to the rhodamine dye Atto 590 and will therefore find applications in FRET‐based analytical RNA systems.

中文翻译：

阳离子发色团的多色大斯托克斯移位氟激活RNA适体。

大型斯托克斯位移（LSS）荧光蛋白（FPs）利用激发态质子转移途径使内部4-羟基亚苄基咪唑酮（HBI）发色团的酚盐中间体发出荧光。一种名为Chili的RNA适体通过诱导几种新的绿色和红色HBI类似物（在溶液中自由时不发荧光）产生的高斯托克斯位移发射来模拟LSS FP。配体以质子化苯酚的形式与RNA结合，并具有阳离子芳族侧链，可增加RNA亲和力并降低镁依赖性。结合咪唑酮C2位置的氧化功能化，该策略产生DMHBO ⁺，该DMHBO ⁺与低纳摩尔K _D的辣椒适体结合。由于其在592 nm处的高红移荧光发射，Chili–DMHBO ⁺复合物是将Förster共振能量转移（FRET）转移至若丹明染料Atto 590的理想荧光供体，因此将在基于FRET的分析RNA系统中找到应用。

更新日期：2019-01-11

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