Citation: Shen Baoxing, Qian Ying. A Novel Fluorescent Dye Naphthalene Imide-Fluorine Boron Two Pyrrole: Synthesis, Fluorescence Resonance Energy Transfer and Cell Imaging[J]. Chinese Journal of Organic Chemistry, ;2016, 36(4): 774-781. doi: 10.6023/cjoc201510028 shu

A Novel Fluorescent Dye Naphthalene Imide-Fluorine Boron Two Pyrrole: Synthesis, Fluorescence Resonance Energy Transfer and Cell Imaging

Shen Baoxing ,
Qian Ying ^,

1.
School of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189

Corresponding author: Qian Ying,
Received Date: 24 October 2015
Available Online: 1 December 2015
Fund Project: 国家自然科学基金(No.61178057)资助项目. (No.61178057)

A novel fluorescent dye naphthalene imide-fluorine boron two pyrrole 1-(2-(4-(1,3,5,7-tetramethyl fluorine boron pyrrole)phenoxy)ethyl)-4-(4-N-butyl-1,8-naphthalene imide)-1,2,3-triazole (NP-BODIPY) has been synthesized by Click reaction and characterized by ¹H NMR, ¹³C NMR and HRMS techniques. NP-BODIPY has the property of intermolecule fluorescence resonance energy transfer from the naphthalene imide to BODIPY, the NP-BODIPY/SiO₂nanoparticles was prepared by positive phase microemulsion. In the test of the UV-vis absorption and fluorescence spectrum of NP-BODIP, purple fluorescence could be observed under ultraviolet lamp when NP-BODIPY was in solid state, green fluorescence could be observed when NP-BODIPY was in THF solution, fluorescence spectrum exhibited bimodal structure in 430 and 510 nm, the fluorescence quantum efficiency of NP-BODIPY was 67% and the ultraviolet absorption peaks were at 366 and 500 nm. The fluorescence quantum efficiency of NP-BODIPY in H₂O/THF mixture solution is 39%. It has strong fluorescence when water fraction is 80%, and the maximum fluorescence peaks are at 510 nm. When NP-BODIPY was co-incubated with michigan cancer foundation-7 cells (MCF-7) cells, the fluorescent dye penetrated into the MCF-7 cells and could be clearly observed. NP-BODIPY/SiO₂nanoparticles exhibit good water solubility, size controllable, low cytotoxicity and good biocompatibility. So NP-BODIPY can be widely used for biomarkers and fluorescence imaging.
- Click reaction,
- naphthalene imide,
- BODIPY,
- fluorescent nanoparticles,
- cell imaging,
- fluorescence resonance energy transfer
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