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J Phys Chem B. 2010 Nov 18;114(45):14157-67. doi: 10.1021/jp907080r. Epub 2009 Oct 27.

Azido push-pull fluorogens photoactivate to produce bright fluorescent labels.

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1
Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA.

Abstract

Dark azido push-pull chromophores have the ability to be photoactivated to produce bright fluorescent labels suitable for single-molecule imaging. Upon illumination, the aryl azide functionality in the fluorogens participates in a photochemical conversion to an aryl amine, thus restoring charge-transfer absorption and fluorescence. Previously, we reported that one compound, DCDHF-V-P-azide, was photoactivatable. Here, we demonstrate that the azide-to-amine photoactivation process is generally applicable to a variety of push-pull chromophores, and we characterize the photophysical parameters including photoconversion quantum yield, photostability, and turn-on ratio. Azido push-pull fluorogens provide a new class of photoactivatable single-molecule probes for fluorescent labeling and super-resolution microscopy. Lastly, we demonstrate that photoactivated push-pull dyes can insert into bonds of nearby biomolecules, simultaneously forming a covalent bond and becoming fluorescent (fluorogenic photoaffinity labeling).

PMID:
19860443
PMCID:
PMC2891317
DOI:
10.1021/jp907080r
[Indexed for MEDLINE]
Free PMC Article
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