Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 26, Issue 50, Pages 11549-11557Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202001163
Keywords
benzorhodamines; dyes; pigments; fluorescence; imaging agents; photothermal therapy
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Funding
- Global Research Laboratory Program through the National Research Foundation (NRF) - Ministry of Science, ICT & Future Planning [2014K1A1A2064569]
- Basic Science Research Program through the National Research Foundation of Korea (NRF) - Ministry of Education [NRF-2019R1A2C2085438]
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Photostable and near-infrared (NIR)-emitting organic fluorophores with large Stokes shifts are in great demand for long-term bioimaging at deeper depths with minimal autofluorescence and self-quenching. Herein, a new class of benzorhodamines and their analogues that are photostable and emit in the NIR region (up to 785 nm) with large Stokes shifts (>120 nm) is reported. The synthesis involves condensation of 7-alkylamino-2-naphthols with 2-[4-(dimethylamino)-2-hydroxybenzoyl]benzoic acid, which leads to bent-shaped benzorhodamines that emit orange fluorescence (approximate to 600 nm); however, introduction of steric hindrance near the condensation site switched the regioselectivity, to provide a linear benzorhodamine system for the first time. The linear benzorhodamine derivatives provide bright fluorescence images in cells and in tissue. A carboxy-benzorhodamine was applied for photothermal therapy of cancer cells and xenograft cancer mice.
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