Synthesis of Near‐Infrared‐Emitting Benzorhodamines and Their Applications to Bioimaging and Photothermal Therapy
| Autor: | Mithun Santra, Hyori Lee, Yun Jae Yang, Chang Wook Song, Yong Woong Jun, Kyo Han Ahn, Won Jong Kim, Mingchong Dai, Ye Jin Reo |
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| Rok vydání: | 2020 |
| Předmět: |
Steric effects
Photothermal Therapy Rhodamines 010405 organic chemistry Optical Imaging Organic Chemistry Near-infrared spectroscopy Regioselectivity General Chemistry Photothermal therapy 010402 general chemistry Photochemistry 01 natural sciences Fluorescence Catalysis 0104 chemical sciences Mice Autofluorescence chemistry.chemical_compound chemistry Neoplasms Benzyl Compounds Animals Fluorescent Dyes Benzoic acid |
| Zdroj: | Chemistry – A European Journal. 26:11549-11557 |
| ISSN: | 1521-3765 0947-6539 |
| Popis: | 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 (≈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. |
| Databáze: | OpenAIRE |
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