A Multicolor Large Stokes Shift Fluorogen‐Activating RNA Aptamer with Cationic Chromophores
Steinmetzger, Christian Palanisamy, Navaneethan Gore, Kiran R Höbartner, Claudia
Steinmetzger, Christian
Palanisamy, Navaneethan
Gore, Kiran R
Höbartner, Claudia
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2018-11-28
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Abstract
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<sup>+</sup> , which binds to the Chili aptamer with a low-nanomolar K<sub>D</sub> . Because of its highly red-shifted fluorescence emission at 592 nm, the Chili-DMHBO<sup>+</sup> 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.
Citation
Steinmetzger, C., Palanisamy, N., Gore, K. R., & Höbartner, C. (2019). A multicolor large stokes shift fluorogen‐activating RNA aptamer with cationic chromophores. Chemistry–A European Journal, 25(8), 1931-1935. https://doi.org/10.1002/chem.201805882
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Wiley
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Chemistry - A European Journal
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DOI
10.1002/chem.201805882
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Article
Language
en
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This is the peer reviewed version of the following article: [Steinmetzger, C., Palanisamy, N., Gore, K. R., & Höbartner, C. (2019). A multicolor large stokes shift fluorogen‐activating RNA aptamer with cationic chromophores. Chemistry–A European Journal, 25(8), 1931-1935.] which has been published in final form at [https://doi.org/10.1002/chem.201805882]. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibited.
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0947-6539
EISSN
1521-3765
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