Excimers Beyond Pyrene: A Far-Red Optical Proximity Reporter and its Application to the Label-Free Detection of DNA

A family of organic chromophores that, like pyrene, forms emissive excimers is reported. Their chemical and photophysical properties are superior to pyrene for the design of chemo‐ and biosensors. Unlike hydrophobic pyrene, which requires excitation by cell‐damaging UV irradiation, these polar dyes...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2015-03, Vol.54 (13), p.3912-3916
Main Authors: Han, Garam, Kim, Dongwook, Park, Younbong, Bouffard, Jean, Kim, Youngmi
Format: Article
Language:English
Subjects:
aggregation
Biosensors
chromophores
Coloring Agents - chemistry
Deoxyribonucleic acid
Derivatives
Dimerization
DNA
DNA - analysis
DNA detection
Dyes
Electrophoresis
Electrophoresis, Polyacrylamide Gel
Excimers
Fluorescence
Fluorescent Dyes
Indicators and Reagents
Models, Molecular
Proximity
Pyrenes
Pyrenes - chemistry
Solvents
Spectrometry, Fluorescence
Spectrophotometry, Ultraviolet
Stilbenes - chemistry
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Summary:A family of organic chromophores that, like pyrene, forms emissive excimers is reported. Their chemical and photophysical properties are superior to pyrene for the design of chemo‐ and biosensors. Unlike hydrophobic pyrene, which requires excitation by cell‐damaging UV irradiation, these polar dyes absorb strongly in the visible range, and their excimers emit brightly in the red to far‐red region of the electromagnetic spectrum. The intensity of the emission signal is greatly increased upon formation of a preassociated dimer that is triggered upon aggregation or crystallization. In demonstration of the potential of this new family of excimer‐forming dyes, a probe that is capable of detecting label‐free DNA in water down to 10 pM and also doubles as a visualization agent for DNA in gel electrophoresis is reported. Let there be light: Cyanovinylene‐based dyes form red‐emitting excimers that surpass pyrene excimers as optical reporters of proximity. The application of a cationic derivative to the label‐free detection of DNA and as a staining agent for DNA in gel electrophoresis is demonstrated.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201410548