Far-red/near-infrared emitting, two-photon absorbing, and bio-stable amino-Si-pyronin dyes

Organic fluorophores emitting in the far-red/near-infrared (NIR) wavelength region are in great demand for minimal autofluorescence and reduced light scattering in deep tissue or whole body imaging. Currently, only a few classes of far-red/NIR fluorophores are available including widely used cyanine...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2019-10, Vol.1 (39), p.928-937
Main Authors: Kim, Kyeong Hwan, Singha, Subhankar, Jun, Yong Woong, Reo, Ye Jin, Kim, Hye Rim, Ryu, Hye Gun, Bhunia, Snehasis, Ahn, Kyo Han
Format: Article
Language:English
Subjects:
Biocompatibility
Chemical compounds
Cyanine dyes
Dyes
Fluorescence
Hydrogen peroxide
Light scattering
Medical imaging
Near infrared radiation
Photons
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Summary:Organic fluorophores emitting in the far-red/near-infrared (NIR) wavelength region are in great demand for minimal autofluorescence and reduced light scattering in deep tissue or whole body imaging. Currently, only a few classes of far-red/NIR fluorophores are available including widely used cyanine dyes, which are susceptible to photobleaching and form nonfluorescent aggregates. Even rare are those far-red/NIR emitting dyes that have two-photon imaging capability. Here we report a new class of far-red/NIR-emitting dyes that are photo-stable, very bright, biocompatible, and also two-photon absorbing. The introduction of an electron-withdrawing group such as N -acyl or N -alkoxycarbonyl groups on the C-10-amino substituent of the new julolidine-derived amino-Si-pyronin dyes (ASiP j ), which emit in the far-red region, causes large bathochromic shifts, leading to NIR-emitting amino-Si-pyronin dyes (NIR-ASiP j ) having high cellular stability. Furthermore, the ASiP j -NIR-ASiP j couple offers a novel ratiometric bioimaging platform with a large spectral gap, as demonstrated here with a boronate-containing NIR-ASiP j derivative that is converted to the corresponding ASiP j dye upon reaction with hydrogen peroxide. Far-red/NIR emitting, two-photon absorbing, biostable aminosilapyronin dyes (ASiP j ) and their derivatives (NIR-ASiP j ) offer novel (ratiometric) bioimaging platforms.
ISSN:2041-6520
2041-6539
DOI:10.1039/c9sc02287b