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

doi:10.6023/cjoc201911022

有机化学 ›› 2020, Vol. 40 ›› Issue (5): 1246-1250.DOI: 10.6023/cjoc201911022 上一篇下一篇

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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

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

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摘要/Abstract

通过克脑文盖尔缩合反应合成了一种近红外I区的氟硼二吡咯荧光染料（QBOP-lys），QBOP-lys染料是由喹啉-氟硼二吡咯与两个对吗啉苯乙烯结构共轭连接而成，是一种D-A构型的染料，该染料的结构通过了核磁共振以及高分辨质谱表征.在DMSO溶液中，QBOP-lys最大吸收波长为698 nm（摩尔消光系数为5.9×10⁴ L·mol^-1·cm^-1），最大发射波长位于770 nm，Stokes位移达到73 nm，荧光量子产率为0.18.此外，QBOP-lys还被制备成水溶性的二氧化硅荧光纳米粒子（QBOP-lys/SiO₂），在纯水溶液中最大发射波长位于726 nm，荧光量子产率达到了0.33，使得QBOP-lys无论是在有机溶剂或者是纯水溶剂中都具有非常好的近红外荧光发射特性.另一方面，QBOP-lys还被用于SGC-7901细胞内的溶酶体成像，染料QBOP-lys与溶酶体商业绿色染料Lyso-Tracker Green的共定位系数高达0.9.此外，染料QBOP-lys在SGC-7901细胞内孵育48 h之后，依然能保持很好的荧光成像效果，可被用于长期的溶酶体追踪成像.染料QBOP-lys的体外实验与细胞实验证明，QBOP-lys是一种非常有应用前景的近红外BODIPY染料.

关键词: D-A型喹啉-氟硼二吡咯, 荧光纳米粒子, 克脑文盖尔缩合反应, 近红外I区荧光成像

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

引用此文

王凌锋, 钱鹰. 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[J]. 有机化学, 2020, 40(5): 1246-1250.

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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