Selective synthesis of substituted amino-quinoline derivatives by C-H activation and fluorescence evaluation of their lipophilicity-responsive properties
| Autor: | Masaomi Sakuma, Minaki Kohno, Satoru Karasawa, Koichi Hamada, Kohei Ohyama, Akihiro Mizutani, Yasufumi Fuchi, Ryusuke Hagihara |
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| Rok vydání: | 2019 |
| Předmět: |
Fluorescence-lifetime imaging microscopy
Reaction mechanisms lcsh:Medicine Quantum yield 02 engineering and technology 010402 general chemistry Photochemistry 01 natural sciences Article chemistry.chemical_compound lcsh:Science Multidisciplinary lcsh:R Quinoline Solvatochromism Single-molecule fluorescence 021001 nanoscience & nanotechnology Fluorescence Lipids 0104 chemical sciences X-ray diffraction Solvent chemistry Yield (chemistry) Lipophilicity Fluorescent probes lcsh:Q 0210 nano-technology |
| Zdroj: | Scientific Reports Scientific Reports, Vol 9, Iss 1, Pp 1-9 (2019) |
| ISSN: | 2045-2322 |
| Popis: | Push-pull type fluorescent amino-quinoline derivatives (TFMAQ) bearing phenyl aromatic groups in the 8-position (TFMAQ-8Ar series) were synthesized via palladium-catalyzed C-H activation reaction in short steps. The N-arylation or C-H activation reactions were selectively controlled with high yield by combinations of palladium and phosphine ligands. The TFMAQ-8Ar analogues exhibited fluorescent solvatochromism in non-polar and polar solvents. In non-polar solvent, the absolute fluorescence quantum yield was high, wheareas the fluorescence was almost quenched in polar solvent. The TFMAQ-8Ar derivatives also showed high fluorescence emission at solid state owing to the planar structure between the quinoline ring and phenyl ring at the 7-amino group, as demonstrated by X-ray crystal structure analysis. The fluorescence imaging of 3T3-L1 cell using TFMAQ-8Ar derivatives was performed by confocal laser microscopy. Strong and specific emissions at lipid droplets were observed owing to the accumulation of TFMAQ-8Ar derivatives. Therefore, we propose that the TFMAQ-8Ar derivatives should become a versatile fluorescence probe for the live imaging of lipid droplets. |
| Databáze: | OpenAIRE |
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