Synthesis of fluorescent dyes based on the electron-withdrawing core of malononitrile and construction of viscosity-sensitive AIE probe with large Stokes shift for lipid droplets imaging

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED Dyes and Pigments Pub Date : 2024-11-07 DOI:10.1016/j.dyepig.2024.112528

Yun-Hao Yang , Wei-Long Cui , Mao-Hua Wang, Jian-Yong Wang

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Abstract

Viscosity is an important parameter of the cell microenvironment and is closely related to the occurrence of many diseases in vivo. Lipid droplets, as organelles that store and metabolize lipids, play a crucial role in various physiological processes related to cell metabolism. Monitoring cell viscosity and lipid droplets status is of great significance in studying cell function and disease pathogenesis. In this study, a series of novel fluorescent dyes were successfully synthesized by using malononitrile derivatives as fluorophores and modified by different substituents. The photophysical data of these dyes were summarized and the effects of different substituents on the optical properties of the dyes were studied. In addition, these dyes showed significant fluorescence enhancement effects in high-viscosity environments. Based on this, we further developed a novel viscosity-sensitive fluorescent probe DCN-LD that can be used for lipid droplets imaging. DCN-LD not only showed high viscosity sensitivity and good fluorescence stability but also exhibited AIE properties, large Stokes shifts (151 nm), and was capable of labeling intracellular lipid droplets. Finally, DCN-LD was successfully applied to monitor the changes in intracellular lipid droplets and changes in intracellular viscosity.

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基于丙二腈缩电子核的荧光染料的合成以及用于脂滴成像的具有大斯托克斯位移的粘度敏感型 AIE 探针的构建

粘度是细胞微环境的一个重要参数，与体内许多疾病的发生密切相关。脂滴作为储存和代谢脂质的细胞器，在与细胞代谢有关的各种生理过程中发挥着至关重要的作用。监测细胞粘度和脂滴状态对研究细胞功能和疾病发病机制具有重要意义。本研究以丙二腈衍生物为荧光团，通过不同的取代基修饰，成功合成了一系列新型荧光染料。研究总结了这些染料的光物理数据，并研究了不同取代基对染料光学性质的影响。此外，这些染料在高粘度环境中显示出显著的荧光增强效应。在此基础上，我们进一步开发了可用于脂滴成像的新型粘度敏感荧光探针 DCN-LD。DCN-LD 不仅具有高粘度敏感性和良好的荧光稳定性，还具有 AIE 特性和较大的斯托克斯位移（151 nm），能够标记细胞内的脂滴。最后，DCN-LD 被成功应用于监测细胞内脂滴的变化和细胞内粘度的变化。

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来源期刊

Dyes and Pigments 工程技术-材料科学：纺织

CiteScore

8.20

自引率

13.30%

发文量

933

审稿时长

33 days

期刊介绍： Dyes and Pigments covers the scientific and technical aspects of the chemistry and physics of dyes, pigments and their intermediates. Emphasis is placed on the properties of the colouring matters themselves rather than on their applications or the system in which they may be applied. Thus the journal accepts research and review papers on the synthesis of dyes, pigments and intermediates, their physical or chemical properties, e.g. spectroscopic, surface, solution or solid state characteristics, the physical aspects of their preparation, e.g. precipitation, nucleation and growth, crystal formation, liquid crystalline characteristics, their photochemical, ecological or biological properties and the relationship between colour and chemical constitution. However, papers are considered which deal with the more fundamental aspects of colourant application and of the interactions of colourants with substrates or media. The journal will interest a wide variety of workers in a range of disciplines whose work involves dyes, pigments and their intermediates, and provides a platform for investigators with common interests but diverse fields of activity such as cosmetics, reprographics, dye and pigment synthesis, medical research, polymers, etc.