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A multicolor large Stokes shift fluorogen-activating RNA aptamer with cationic chromophores
Please always quote using this URN: urn:nbn:de:bvb:20-opus-174197
- 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 analogs 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 andLarge 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 analogs 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 functional-ization 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.…
Author: | Claudia HöbartnerORCiD, Christian Steinmetzger, Navaneethan Palanisamy, Kiran R. Gore |
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URN: | urn:nbn:de:bvb:20-opus-174197 |
Document Type: | Preprint |
Faculties: | Fakultät für Chemie und Pharmazie / Institut für Organische Chemie |
Language: | English |
Parent Title (English): | Chemistry - A European Journal |
Year of Completion: | 2018 |
Source: | Chemistry - A European Journal. doi:10.1002/chem.201805882 |
DOI: | https://doi.org/https://doi.org/10.1002/chem.201805882 |
Sonstige beteiligte Institutionen: | International Max Planck Research School Molecular Biology, University of Göttingen, Germany |
Sonstige beteiligte Institutionen: | Center for Nanoscale Microscopy and Molecular Physiology of the Brain (CNMPB), Göttingen, Germany |
Dewey Decimal Classification: | 5 Naturwissenschaften und Mathematik / 54 Chemie / 547 Organische Chemie |
Tag: | RNA Aptamer; fluorescence; fluorescent protein; fluorescent resonance energy transfer; large Stokes shift |
Release Date: | 2018/12/20 |
EU-Project number / Contract (GA) number: | 682586 |
OpenAIRE: | OpenAIRE |
Note: | This is the pre-peer reviewed version of the following article: Steinmetzger, C. , Palanisamy, N. , Gore, K. . and Höbartner, C. (2018), A multicolor large Stokes shift fluorogen‐activating RNA aptamer with cationic chromophores. Chem. Eur. J. doi:10.1002/chem.201805882, 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. |
Licence (German): | Deutsches Urheberrecht |