Citation: Zhifeng Li, Qinglong Qiao, Ning Xu, Kai An, Wenchao Jiang, Yi Tao, Pengjun Bao, Yinchan Zhang, Zhaochao Xu. The remarkable effect of amino hydrogen on membrane permeability and organelle staining of 1,8-naphthalimide dyes[J]. Chinese Chemical Letters, ;2024, 35(2): 108824. doi: 10.1016/j.cclet.2023.108824 shu

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

Zhifeng Li ^{a, b} ,
Qinglong Qiao ^{b, *,} ,
Ning Xu ^{a, b} ,
Kai An ^{b, c} ,
Wenchao Jiang ^{b, c} ,
Yi Tao ^{b, c} ,
Pengjun Bao ^{b, c} ,
Yinchan Zhang ^{b, c} ,
Zhaochao Xu ^{a, b, *,}

a.
School of Chemistry, Dalian University of Technology, Dalian 116024, China
b.
CAS Key Laboratory of Separation Science for Analytical Chemistry, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China
c.
University of Chinese Academy of Sciences, Beijing 100049, China

qqlqiao@dicp.ac.cn

zcxu@dicp.ac.cn

Received Date: 14 June 2023
Revised Date: 17 July 2023
Accepted Date: 18 July 2023
Available Online: 20 July 2023

Figures(4)

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