A series of cyanine based bright fluorescent dyes were designed and synthesized by varying substituents in structure. These fluorescent probes exhibited significantly larger Stokes shifts (60 – 200 nm) and higher fluorescence quantum yields. Fluorescence microscopy imaging showed exceptional selectivity of cyanine dyes towards mitochondria (1 – 10) and lysosome (11 – 20) localization in live cells. Linkage of para-N-di-substituted benzaldehyde compounds in to vinylbenzothiazolium moiety permitted mitochondrial selectivity to cyanine probes. Series of mitochondria probes (1 – 10) accommodate red to near-infrared (NIR) emitters with facile “wash-free” application in to live cells with no cytotoxicity effect under working concentrations. Low energy excitation feature (λ &gt; 550 nm) provides a secure working environment in fluorescent microscopy to minimize cell damage and cellular auto fluorescence. Lysosome selectivity feature was attained in the absence of N-substituted amino groups in cyanine structure. Attachment of benzothiazlole substituents and hydroxyl groups in to center aromatic moiety (11 – 20) enhanced lysosome selectivity of the probes notably. The degree of lysosome selectivity of the probes found to be dependent on relative positions of the substituents in structure with respect to the cyanine group attached. The “non-alkalyzing” nature of new lysosome probe series significantly minimizes cytotoxicity compared to commercial lysosome probes and provides ability to perform long-duration imaging experiments in live cells. Extended Stokes shift feature minimizes possible self-absorption effect to provide high probe efficiency. These cyanine probe series could be a potential successor for existing commercial dyes.

Structural tuning of cyanine fluorophores for mitochondria and lysosome targeting: Highly selective series of fluorescent probes

254th National Meeting (2017)

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