ArticleJournal of the American Chemical Society2013
Twisted cyanines: a non-planar fluorogenic dye with superior photostability and its use in a protein-based fluoromodule.
Article in Journal of the American Chemical Society, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed, 99 citations in OpenAlex.
- Plate-Based High-Throughput Fluorescence Assay for Assessing Enveloped Virus Integrity.Biomacromolecules · 2024Article
- Optimization of the fluorogen-activating protein tag for quantitative protein trafficking and colocalization studies inMolecular biology of the cell · 2024Article
- Development of Highly Fluorogenic Styrene Probes for Visualizing RNA in Live Cells.ACS chemical biology · 2023Article
- Tracking RNA with light: selection, structure, and design of fluorescence turn-on RNA aptamers.Quarterly reviews of biophysics · 2019Review
- A 5'-BODIPY End-label for Monitoring DNA Duplex-Quadruplex Exchange.Scientific reports · 2018Article
- A homodimer interface without base pairs in an RNA mimic of red fluorescent protein.Nature chemical biology · 2017Article
- Breaking the color barrier - a multi-selective antibody reporter offers innovative strategies of fluorescence detection.Journal of cell science · 2017Article
- Multiexcitation Fluorogenic Labeling of Surface, Intracellular, and Total Protein Pools in Living Cells.Bioconjugate chemistry · 2016Article
- Genetically targeted fluorogenic macromolecules for subcellular imaging and cellular perturbation.Biomaterials · 2015Article
- Engineering tandem single-chain Fv as cell surface reporters with enhanced properties of fluorescence detection.Protein engineering, design & selection : PEDS · 2015Article
- Spectral fine tuning of cyanine dyes: electron donor-acceptor substituted analogues of thiazole orange.Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology · 2015Article
- Trichocyanines: a Red-Hair-Inspired Modular Platform for Dye-Based One-Time-Pad Molecular Cryptography.ChemistryOpen · 2015Article
- Rapid, specific, no-wash, far-red fluorogen activation in subcellular compartments by targeted fluorogen activating proteins.ACS chemical biology · 2015Article
- Photoinduced dynamics of a cyanine dye: parallel pathways of non-radiative deactivation involving multiple excited-state twisted transients.Chemical science · 2015Article
- Bichromophoric dyes for wavelength shifting of dye-protein fluoromodules.Organic & biomolecular chemistry · 2015Article
- Monoalkoxy BODIPYs--a fluorophore class for bioimaging.Bioconjugate chemistry · 2014Article
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Authors and funding
4 authors at 2 institutions in 1 country.
Funding
Abstract
The cyanine dye thiazole orange (TO) is a well-known fluorogenic stain for DNA and RNA, but this property precludes its use as an intracellular fluorescent probe for non-nucleic acid biomolecules. Further, as is the case with many cyanines, the dye suffers from low photostability. Here, we report the synthesis of a bridge-substituted version of TO named α-CN-TO, where the central methine hydrogen of TO is replaced by an electron withdrawing cyano group, which was expected to decrease the susceptibility of the dye toward singlet oxygen-mediated degradation. An X-ray crystal structure shows that α-CN-TO is twisted drastically out of plane, in contrast to TO, which crystallizes in the planar conformation. α-CN-TO retains the fluorogenic behavior of the parent dye TO in viscous glycerol/water solvent, but direct irradiation and indirect bleaching studies showed that α-CN-TO is essentially inert to visible light and singlet oxygen. In addition, the twisted conformation of α-CN-TO mitigates nonspecific binding and fluorescence activation by DNA and a previously selected TO-binding protein and exhibits low background fluorescence in HeLa cell culture. α-CN-TO was then used to select a new protein that binds and activates fluorescence from the dye. The new α-CN-TO/protein fluoromodule exhibits superior photostability to an analogous TO/protein fluoromodule. These properties indicate that α-CN-TO will be a useful fluorogenic dye in combination with specific RNA and protein binding partners for both in vitro and cell-based applications. More broadly, structural features that promote nonplanar conformations can provide an effective method for reducing nonspecific binding of cationic dyes to nucleic acids and other biomolecules.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.