4.7 Article

Convenient construction of fluorescent markers for lipid droplets with 1,8-naphthalimide unit

期刊

DYES AND PIGMENTS
卷 186, 期 -, 页码 -

出版社

ELSEVIER SCI LTD
DOI: 10.1016/j.dyepig.2020.109003

关键词

1,8-Naphthalimide; Lipid droplets; Fluorescent bioimaging; Amine; Ullmann reaction

资金

  1. National Natural Science Foundation of China [21977078]
  2. Natural Science Foundation of Jiangsu Province [BK20181429]
  3. Collaborative Innovation Center of Radiological Medicine of Jiangsu Higher Education Institutions

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This study successfully synthesized fluorescent dyes with high fluorescence quantum yields and excellent photostability by modifying 1,8-naphthalimide, which can effectively label lipid droplets with low toxicity.
1,8-Naphthalimide is widely applied in the construction of probes because it is easy to be modified. However, 1,8-naphthalimide has been reported rarely in the application of organelle labelling especially lipid droplets (LDs). Herein, three types of amine compounds, aliphatic amine (a, b), aromatic amine (c, d) and heterocyclic amine (e, f), were chosen to construct fluorescent dyes (1a-1f) with 4-bromo-N-butylnaphthalimide (1) by Ullmann reaction. The maximum emission wavelength ranged from 490 nm to 550 nm. What's more, 1a-1e showed high fluorescence quantum yields (0.54-0.93) in chloroform and 1e-1f had excellent photostability (>92%). In addition, the cell imaging experiment showed that they could label lipid droplets for HeLa cancer cells and L929 normal cells with extremely low toxicity. This work realizes the classical fluorophore 1,8-naphthalimide to synthesize a series of LDs markers without complex synthesis steps.

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