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Angew Chem Int Ed Engl. 2015 May 26;54(22):6442-6. doi: 10.1002/anie.201502403. Epub 2015 May 7.

Photoelectrocyclization as an activation mechanism for organelle-specific live-cell imaging probes.

Author information

1
Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, PA 19104 (USA).
2
Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, PA 19104 (USA). dcheno@sas.upenn.edu.

Abstract

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.

KEYWORDS:

electrocyclization; fluorescent probes; imaging agents; photochemistry

PMID:
25950154
PMCID:
PMC4485560
DOI:
10.1002/anie.201502403
[Indexed for MEDLINE]
Free PMC Article

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