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基于 4-苯乙炔-1,8-萘酰亚胺的一系列荧光染料:合成、理论计算、光物理性质及其在脂质体和溶酶体双色成像及动态行为监测中的应用。

A series of fluorescent dyes based on 4-phenylacetylene-1,8-naphthalimide: Synthesis, theoretical calculations, photophysical properties and application in two-color imaging and dynamic behavior monitoring of lipid droplets and lysosomes.

机构信息

Faculty of Light Industry, State Key Laboratory of Biobased Material and Green Papermaking, Key Laboratory of Pulp and Paper Science & Technology of Ministry of Education, Qi Lu University of Technology (Shandong Academy of Sciences), No. 3501, Daxue Road, Changqing District, Jinan 250353, Shandong Province, PR China.

Faculty of Light Industry, State Key Laboratory of Biobased Material and Green Papermaking, Key Laboratory of Pulp and Paper Science & Technology of Ministry of Education, Qi Lu University of Technology (Shandong Academy of Sciences), No. 3501, Daxue Road, Changqing District, Jinan 250353, Shandong Province, PR China.

出版信息

Spectrochim Acta A Mol Biomol Spectrosc. 2023 Dec 15;303:123207. doi: 10.1016/j.saa.2023.123207. Epub 2023 Jul 26.

DOI:10.1016/j.saa.2023.123207
PMID:37542875
Abstract

A series of fluorescent dyes (NapPAs) based on 4-phenylacetylene-1,8-naphthalimide were synthesized and characterized, whose conjugated structures were extended by the introduction of phenylethynyl. Furthermore, changes in the photophysical properties of the dyes when substituents with varying electron richness were introduced at the p-position of phenylacetylene were studied. The theoretical calculation of the dye molecules was carried out by B3LYP functional and 6-31G(d,p) basis set, and the effects of different substituents at the p-position of phenylacetylene on the electronic structure and photophysical properties of the dyes were studied by theoretical calculation results. Theoretical calculations provided a reliable means of predicting the properties of dyes, which could help in the design of more efficient and novel dyes. To verify the practicability of the dyes, two dyes with excellent photophysical properties (large Stokes shift, high polarity-viscosity sensitivity, good biocompatibility) were selected as fluorescent probes for visualization of LDs and two-color imaging of LDs and lysosomes. Cell imaging showed that NapPA-LDs and NapPA-LDs-Lyso serve as excellent imaging tools to monitor the dynamic changes, movements, and behaviors of LDs and lysosomes in real time. Notably, NapPA-LDs-Lyso held promise as a potential tool to study the interaction between LDs and lysosomes.

摘要

一系列基于 4-苯乙炔-1,8-萘酰亚胺的荧光染料(NapPAs)被合成并进行了表征,其共轭结构通过引入苯乙炔得到了扩展。此外,还研究了在苯乙炔的 p 位引入具有不同电子富度的取代基时,染料的光物理性质的变化。通过 B3LYP 函数和 6-31G(d,p)基组对染料分子进行了理论计算,并通过理论计算结果研究了苯乙炔的 p 位不同取代基对染料电子结构和光物理性质的影响。理论计算为预测染料性质提供了可靠的手段,有助于设计更高效、新颖的染料。为了验证染料的实用性,选择了两种具有优异光物理性质的染料(大斯托克斯位移、高极性-粘度灵敏度、良好的生物相容性)作为荧光探针,用于可视化 LD 和 LD 和溶酶体的双色成像。细胞成像表明,NapPA-LD 和 NapPA-LD-Lyso 可以作为监测 LD 和溶酶体的动态变化、运动和行为的优异成像工具,实时进行监测。值得注意的是,NapPA-LD-Lyso 有望成为研究 LD 和溶酶体之间相互作用的潜在工具。

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