中国化学快报(英文版)2024,Vol.35Issue(2) :347-351.DOI:10.1016/j.cclet.2023.108824

The remarkable effect of amino hydrogen on membrane permeability and organelle staining of 1,8-naphthalimide dyes

Zhifeng Li Qinglong Qiao Ning Xu Kai An Wenchao Jiang Yi Tao Pengjun Bao Yinchan Zhang Zhaochao Xu
中国化学快报(英文版)2024,Vol.35Issue(2) :347-351.DOI:10.1016/j.cclet.2023.108824

The remarkable effect of amino hydrogen on membrane permeability and organelle staining of 1,8-naphthalimide dyes

Zhifeng Li 1Qinglong Qiao 2Ning Xu 1Kai An 3Wenchao Jiang 3Yi Tao 3Pengjun Bao 3Yinchan Zhang 3Zhaochao Xu1
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作者信息

  • 1. School of Chemistry,Dalian University of Technology,Dalian 116024,China;CAS Key Laboratory of Separation Science for Analytical Chemistry,Dalian Institute of Chemical Physics,Chinese Academy of Sciences,Dalian 116023,China
  • 2. CAS Key Laboratory of Separation Science for Analytical Chemistry,Dalian Institute of Chemical Physics,Chinese Academy of Sciences,Dalian 116023,China
  • 3. CAS Key Laboratory of Separation Science for Analytical Chemistry,Dalian Institute of Chemical Physics,Chinese Academy of Sciences,Dalian 116023,China;University of Chinese Academy of Sciences,Beijing 100049,China
  • 折叠

Abstract

Membrane permeability and intracellular diffusion of fluorescent probes determine staining selectivity of intracellular substructures.However,the relationship between the molecular structure of fluorescent probes and their membrane permeability and intracellular distribution is poorly understood.In this paper,we reported a series of 1,8-naphthalimide dyes and carried out cell imaging experiments,and found that the presence of amino hydrogen in these dyes played a crucial role in their cell membrane permeabil-ity and intracellular distribution.The secondary amino group containing compounds 1-4 show excellent membrane permeability and strong fluorescence in living cells.While the tertiary amine containing dyes 5 and 6 can hardly permeate the cell membrane though they show extremely similar structure with com-pounds 2-4.Compound 1 can selectively image lipid droplets by selecting the wavelength of excitation light.With the specificity for lysosomes,2 and 4 have been used in long-term time-lapses imaging of lysosomal dynamics and tracking the process of lysosome-lysosome interaction,fusion and movement.The effect of hydrogen-containing amino substituent on the cell membrane permeability of fluorescent molecules is promising for the development of better biocompatible probes.

Key words

Amino hydrogen/1,8-Naphthalimide/Cell permeability/Lipid droplet/Lysosome

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基金项目

国家自然科学基金(22278394)

国家自然科学基金(22078314)

国家自然科学基金(21908216)

Dalian Institute of Chemical Physics(DICPI202227)

Dalian Institute of Chemical Physics(DICPI202142)

出版年

2024
中国化学快报(英文版)
中国化学会

中国化学快报(英文版)

CSTPCDCSCD
影响因子:0.771
ISSN:1001-8417
参考文献量39
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