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

doi:10.6023/cjoc201911022

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

近红外I区喹啉-氟硼二吡咯荧光染料的合成及其在溶酶体内的荧光成像

王凌锋, 钱鹰

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 E-mail:yingqian@seu.edu.cn

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

Wang Lingfeng, Qian Ying

School of Chemistry and Chemical Engineering, Southeast University, Nanjing 211100

Received:2019-11-13 Revised:2019-12-23 Published:2020-01-15

1. 201246S.pdf(792KB)

Abstract

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

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Wang Lingfeng, Qian Ying. Near-Infrared Quinoline-Fluoroborodipyrrole Dye: Synthesis and Lysosomal Fluorescence Imaging[J]. Chinese Journal of Organic Chemistry, 2020, 40(5): 1246-1250.

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近红外I区喹啉-氟硼二吡咯荧光染料的合成及其在溶酶体内的荧光成像

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

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