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Convenient construction of fluorescent markers for lipid droplets with 1,8-naphthalimide unit
Dyes and Pigments ( IF 4.5 ) Pub Date : 2020-11-13 , DOI: 10.1016/j.dyepig.2020.109003
Jing-Yang Ni , Xiao-Feng Weng , Ru Sun , Yu-Jie Xu , Jian-Feng Ge

1,8-Naphthalimide was widely applied in the construction of probes because it is easy to modify. 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.



中文翻译:

使用1,8-萘二甲酰亚胺单元方便地构建脂质滴的荧光标记

1,8-萘二甲酰亚胺由于易于修饰而被广泛应用于探针的构建中。然而,在细胞器标记特别是脂质滴(LDs)的应用中,很少报道过1,8-萘二甲酰亚胺。在此,选择了三种胺化合物,脂族胺(ab),芳族胺(cd)和杂环胺(ef),以构建具有4-溴-N-的荧光染料(1a - 1f)。丁基萘二甲酰亚胺(1)通过乌尔曼反应。最大发射波长范围为490 nm至550 nm。更重要的是1a-1e在氯仿中显示出较高的荧光量子产率(0.54-0.93),而1e-1f具有出色的光稳定性(> 92%)。此外,细胞成像实验表明,它们可以以极低的毒性标记HeLa癌细胞和L929正常细胞的脂质滴。这项工作实现了经典的荧光团1,8-萘二甲酰亚胺,无需复杂的合成步骤即可合成一系列LDs标记。

更新日期:2020-11-13
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