Photoelectrocyclization as an Activation Mechanism for Organelle-Specific Live-Cell Imaging Probes

Photoactivatable fluorophores are useful tools in live‐cell imaging owing to their potential for precise spatial and temporal control. In this report, a new photoactivatable organelle‐specific live‐cell imaging probe based on a 6π electrocyclization/oxidation mechanism is described. It is shown that...

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Bibliographic Details
Published in:Angewandte Chemie 2015-05, Vol.127 (22), p.6542-6546
Main Authors: Tran, Mai N., Chenoweth, David M.
Format: Article
Language:eng ; ger
Subjects:
Activation
Chemical compounds
Chemistry
Displays
Dyes
Elektrocyclisierungen
Fluid flow
Fluorescence
Fluoreszenzsonden
Imaging
Kontrastmittel
Photochemie
Temporal logic
Utilities
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Summary:Photoactivatable fluorophores are useful tools in live‐cell imaging owing to their potential for precise spatial and temporal control. In this report, a new photoactivatable organelle‐specific live‐cell imaging probe based on a 6π electrocyclization/oxidation mechanism is described. It is shown that this new probe is water‐soluble, non‐cytotoxic, cell‐permeable, and useful for mitochondrial imaging. The probe displays large Stokes shifts in both pre‐activated and activated forms, allowing simultaneous use with common dyes and fluorescent proteins. Sequential single‐cell activation experiments in dense cellular environments demonstrate high spatial precision and utility in single‐ or multi‐cell labeling experiments. Eine photoaktivierbare organellspezifische Fluoreszenzsonde zur Abbildung lebender Zellen wird beschrieben, deren Funktion auf einer 6π‐Elektrocyclisierung und Oxidation beruht. Die Verbindung ist wasserlöslich, nicht zytotoxisch und zellpermeabel und wurde zur Bildgebung von Mitochondrien genutzt.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201502403