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Synthesis of highly selective lysosomal markers by coupling 2-(2′-hydroxyphenyl)benzothiazole (HBT) with benzothiazolium cyanine (Cy): the impact of substituents on selectivity and optical properties

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Abstract

HBT-Cy 1 has been previously reported as a highly selective fluorescent probe for lysosome visualization in live cells. To further investigate the role of the structural components of HBT-Cy in lysosome selectivity, cyanine based fluorescent probe series (2–5) have been synthesized in good yields by connecting benzothiazolium cyanine (Cy) with 2-hydroxyphenylbenzothiazole (HBT) via a meta phenylene ring. Probes 2–5 exhibited exceptional photophysical properties including bright red-emission (λem ≈ 630–650 nm), a large Stokes shift (Δλ > 130 nm) and high fluorescence quantum yields (ϕfl ≈ 0.1–0.5). Probes 2, 3, and 5 exhibited exceptional selectivity towards cellular lysosomes in NHLF and MO3.13 cells. Our further study revealed that the phenyl benzothiazolium cyanine component (6) was the lysosome directing group in the HBT-Cy probe structure. The attachment of the hydroxyphenyl benzothiazole (HBT) component to the HBT-Cy probe structure has significantly improved its photophysical properties. Lysosome probes 2, 3 and 5 exhibited excellent biocompatibility, quick staining, bright red fluorescence, and wash-free application for live cell imaging. These probes further exhibited excellent characteristics for bioimaging experiments including a non-alkalinizing nature, high biocompatibility, high photostability and long-term imaging ability (>4 hours).

Graphical abstract: Synthesis of highly selective lysosomal markers by coupling 2-(2′-hydroxyphenyl)benzothiazole (HBT) with benzothiazolium cyanine (Cy): the impact of substituents on selectivity and optical properties

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Publication details

The article was received on 07 Aug 2019, accepted on 03 Oct 2019 and first published on 28 Oct 2019


Article type: Paper
DOI: 10.1039/C9TB01672D
J. Mater. Chem. B, 2019, Advance Article

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    Synthesis of highly selective lysosomal markers by coupling 2-(2′-hydroxyphenyl)benzothiazole (HBT) with benzothiazolium cyanine (Cy): the impact of substituents on selectivity and optical properties

    C. S. Abeywickrama, K. A. Bertman, L. J. Mcdonald, N. Alexander, D. Dahal, H. J. Baumann, C. R. Salmon, C. Wesdemiotis, M. Konopka, C. A. Tessier and Y. Pang, J. Mater. Chem. B, 2019, Advance Article , DOI: 10.1039/C9TB01672D

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