Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (4): 774-781.DOI: 10.6023/cjoc201510028 Previous Articles     Next Articles

ARTICLE

新型萘酰亚胺-氟硼二吡咯荧光分子的合成、荧光共振能量转移及细胞成像 2017-2018 Awarded

沈宝星, 钱鹰   

  1. 东南大学化学化工学院 南京 211189
  • 收稿日期:2015-10-24 修回日期:2015-12-01 出版日期:2016-04-25 发布日期:2015-12-21
  • 通讯作者: 钱鹰 E-mail:yingqian@seu.edu.cn
  • 基金资助:

    国家自然科学基金(No.61178057)资助项目.

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
  • Received:2015-10-24 Revised:2015-12-01 Online:2016-04-25 Published:2015-12-21
  • Supported by:

    Project supported by the National Natural Science Foundation of China (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/SiO2 nanoparticles exhibit good water solubility, size controllable, low cytotoxicity and good biocompatibility. So NP-BODIPY can be widely used for biomarkers and fluorescence imaging.

Key words: Click reaction, naphthalene imide, BODIPY, fluorescent nanoparticles, cell imaging, fluorescence resonance energy transfer