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Bioorg Med Chem. 2013 Jun 15;21(12):3602-8. doi: 10.1016/j.bmc.2013.02.049. Epub 2013 Mar 14.

New repertoire of 'donor-two-acceptor' NIR fluorogenic dyes.

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Department of Organic Chemistry, School of Chemistry, Raymond and Beverly Sackler Faculty of Exact Sciences, Tel Aviv University, Tel Aviv 69978, Israel.


Dye molecules with various fluorescent wavelengths are widely used for diagnostic and optical imaging applications. Accordingly, there is a constant demand for fluorogenic dyes with new properties. We have recently developed a novel strategy for the design of long-wavelength fluorescent dyes with a turn-ON option. The design is based on a donor-two-acceptor π-electron system that can undergo an internal charge transfer to form a new fluorochrome with an extended π-conjugated system. Here, we describe a series of such dyes based on two novel latent donors, naphthol and hydroxycoumarin. One of the dyes has showed excellent near-infrared fluorescent characteristics and specifically was demonstrated as a mitochondrial imaging reagent in live cells. This unique strategy for fluorogenic dye design has opened new doors for further near-infrared fluorescence probe discovery.

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