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  • Title: Molecular design strategies for near-infrared ratiometric fluorescent probes based on the unique spectral properties of aminocyanines.
    Author: Kiyose K, Aizawa S, Sasaki E, Kojima H, Hanaoka K, Terai T, Urano Y, Nagano T.
    Journal: Chemistry; 2009 Sep 14; 15(36):9191-200. PubMed ID: 19650089.
    Abstract:
    In spite of the wide availability of various near-infrared (NIR) fluorophores as labeling reagents, there are few functional NIR fluorescent probes for which change in the absorption and/or fluorescence spectra upon specific reaction with biomolecules is seen. The widely used photoinduced electron-transfer mechanism is unsuitable for NIR fluorophores, such as tricarbocyanines, because their long excitation wavelength results in a small singlet excitation energy. We have reported the unique spectral properties of amine-substituted tricarbocyanines, which were utilized to develop two design strategies. One approach was based on control of the absorption wavelength by using the difference in electron-donating ability before and after a specific reaction with a biomolecule, and the other approach was based on control of the fluorescence intensity by modulating the Förster resonance energy-transfer efficiency through a change in the overlap integral that arises from the change in absorption under acidic conditions. These strategies were validated by obtaining tricarbocyanine-based ratiometric NIR fluorescent probes for esterase and for pH level.
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