Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (5): 1246-1250.DOI: 10.6023/cjoc201911022 Previous Articles     Next Articles


王凌锋, 钱鹰   

  1. 东南大学化学化工学院 南京 211100
  • 收稿日期:2019-11-13 修回日期:2019-12-23 发布日期:2020-01-15
  • 通讯作者: 钱鹰

Near-Infrared Quinoline-Fluoroborodipyrrole Dye: Synthesis and Lysosomal Fluorescence Imaging

Wang Lingfeng, Qian Ying   

  1. School of Chemistry and Chemical Engineering, Southeast University, Nanjing 211100
  • Received:2019-11-13 Revised:2019-12-23 Published:2020-01-15

A near-infrared region (NIR) fluoroborodipyrrole fluorescent dye (QBOP-lys) was synthesized through Knoevenagel condensation reaction. The D-A configuration of the QBOP-lys dyes was conjugated by two p-morpholine styrene with one 8-hydroxyquino BODIPY structure. This QBOP-lys dye has been characterized by NMR and high resolution mass spectrometry. In dimethyl sulfoxide (DMSO) solution, the maximum absorption wavelength of QBOP-lys was at 698 nm and its molar extinction coefficient was 5.9×104 L·mol-1·cm-1, the maximum emission wavelength was at 770 nm and its stokes shift was 73 nm. Besides that, QBOP-lys has been prepared as water-soluble nano-silica fluorescent nanoparticles (QBOP-lys/SiO2). The maximum emission wavelength of QBOP-lys/SiO2 was 726 nm in pure aqueous solution and the fluorescence quantum of QBOP-lys/SiO2 was 0.33, which made QBOP-lys have good near-infrared fluorescence emission characteristics in organic solvents or pure water. On the other hand, QBOP-lys was also used for lysosomal imaging in SGC-7901 cells, the colocalization coefficient of dye QBOP-lys with Lyso-Tracker Green, a commercial lysosomal green dye, was up to 0.9. Besides that, after QBOP-lys incubate with cells SGC-7901 for 48 h, it could still maintain good fluorescence imaging performance which could be used for long-term tracking imaging. The spectroscopy experiments and cell experiments both proved that dye QBOP-lys was a very promising NIR dye in future application.

Key words: D-A type quinoline-fluoroboron dipyrrole, fluorescent nanoparticles, Knoevenagel condensation reaction, NIR fluorescence imaging