An indole-fused quinacridone-based fluorescent probe with high photostability and specificity for cellular lipid droplets

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments Pub Date : 2025-04-14 DOI:10.1016/j.dyepig.2025.112835

Yutong Ouyang , Haonan Xiong , Huanlong Zheng , Chenguang Wang , Chuandong Dou , Yufei Gao

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Abstract

Lipid droplets (LDs) are critical organelles that participate in numerous biological processes in eukaryotic cells. However, the unsatisfying specificity to LDs and poor photostability of previous fluorescent probes (e.g. BODIPY 493/503, Nile Red) have substantially limited the in-depth investigations into LDs, particularly for the small and nascent LDs. Herein, inspired by the outstanding photophysical properties of the classical pigment quinacridone (QA), QA was chosen as an excellent π-skeleton to constitute superior fluorescent probe. The indole cores and ether chains were successfully incorporated into its π-skeleton to construct a novel fluorescent probe IQA1. Compared to conventional fluorescent probes, IQA1 not only demonstrates innate superb photostability, but also exhibits superior specificity to LDs. The long ether chains effectively reversed the insolubility of QA in lipids, endowing IQA1 with appropriate lipophilicity to traverse the cell membrane and target LDs. These advantages are conductive to the application of IQA1 in various LDs fluorescence imaging, e.g. 3D confocal imaging of the quantification and dimensions of LDs in the ferroptosis HeLa cells and the oleic acid stimulated HeLa cells, time-lapse structured illumination microscopy (SIM) imaging to observe the dynamics of LDs at nanoscale (178 nm). This study thus not only provides a fascinating fluorescent probe IQA1 for LDs advanced imaging, but also explores a new area for quinacridone pigment application.

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一种基于吲哚融合喹吖啶酮的荧光探针，具有高光稳定性和细胞脂滴特异性

脂滴是真核细胞中参与许多生物过程的重要细胞器。然而，以往荧光探针（如BODIPY 493/503， Nile Red）对ld的特异性不理想，光稳定性差，极大地限制了对ld的深入研究，特别是对小型和新生ld的深入研究。本文受经典色素喹吖啶酮（QA）优异的光物理性质的启发，选择QA作为优良的π-骨架来构成优越的荧光探针。将吲哚核和醚链成功地结合到其π-骨架中，构建了新型荧光探针IQA1。与传统荧光探针相比，IQA1不仅具有良好的光稳定性，而且对ld具有优越的特异性。长醚链有效地逆转了QA在脂质中的不溶性，使IQA1具有适当的亲脂性，可以穿过细胞膜和靶ld。这些优点有助于IQA1在各种ld荧光成像中的应用，例如，对铁下垂HeLa细胞和油酸刺激HeLa细胞ld的定量和尺寸的三维共聚焦成像，以及在纳米（178 nm）尺度上观察ld动态的延时结构照明显微镜（SIM）成像。因此，本研究不仅为ld的高级成像提供了一个有吸引力的荧光探针IQA1，而且为喹吖酮色素的应用开辟了新的领域。

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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.