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NIR-emitting benzothiazolium cyanines with an enhanced stokes shift for mitochondria imaging in live cells

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Abstract

A series of benzothiazolium-based hemicyanines (3a–3f) have been synthesized. Evaluation of their photophysical properties shows that they exhibit improved photophysical characteristics. In comparison with the available commercial MitoTrackers, the new probes revealed an enhanced Stokes shift (Δλ ∼ 80 nm) and minimized aggregation for increased sensitivity. The synthesized probes are found to exhibit excellent selectivity for mitochondrial staining in an oligodendrocyte cell line. Probes show almost no fluorescence in aqueous environments, while the fluorescence is increased by ∼10-fold in organic solvents, making it possible for mitochondrial imaging without the need for post-staining washing. Since the absorption peaks of probes are close to the laser wavelengths of 561 and 640 nm on a commercial confocal microscope, e.g. 3a exhibits λabs ∼ 620 nm and λem ∼ 702 nm, they could be useful probes for mitochondrial tracking in live cells.

Graphical abstract: NIR-emitting benzothiazolium cyanines with an enhanced stokes shift for mitochondria imaging in live cells

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Publication details

The article was received on 08 Feb 2018, accepted on 11 Apr 2018 and first published on 11 Apr 2018


Article type: Paper
DOI: 10.1039/C8OB00327K
Citation: Org. Biomol. Chem., 2018, Advance Article
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    NIR-emitting benzothiazolium cyanines with an enhanced stokes shift for mitochondria imaging in live cells

    C. S. Abeywickrama, H. J. Baumann, N. Alexander, L. P. Shriver, M. Konopka and Y. Pang, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB00327K

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