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 International Edition 2015-05, Vol.54 (22), p.6442-6446
Main Authors: Tran, Mai N., Chenoweth, David M.
Format: Article
Language:English
Subjects:
Cyclization
electrocyclization
Fluorescent Dyes - chemistry
Fluorescent Dyes - metabolism
fluorescent probes
HeLa Cells
Humans
imaging agents
Luminescent Proteins - chemistry
Luminescent Proteins - metabolism
Microscopy, Fluorescence
Mitochondria - metabolism
Mitochondria - pathology
Oxidation-Reduction
photochemistry
Stereoisomerism
X-Rays
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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. A photoactivatable organelle‐specific live‐cell imaging probe based on a 6π electrocyclization/oxidation mechanism is described. This probe is water‐soluble, non‐cytotoxic, cell‐permeable, and can be used for mitochondrial imaging.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201502403