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基于一系列合成的芳基萘衍生物的用于监测脂滴极性的 AIE 荧光探针的修饰。

Modification of an AIE Fluorescent Probe for Monitoring the Polarity of Lipid Droplets Based on a Series of Synthesized Aryl Naphthalizes.

机构信息

Faculty of Light Industry, State Key Laboratory of Biobased Material and Green Papermaking, Key Laboratory of Paper Science and Technology of Ministry of Education, Qi Lu University of Technology (Shandong Academy of Sciences), Jinan, 250353, P. R. China.

出版信息

Chemistry. 2024 Oct 17;30(58):e202401763. doi: 10.1002/chem.202401763. Epub 2024 Oct 2.

Abstract

Lipid droplets (LDs) are subcellular organelles that are dynamic and play a central role in energy homeostasis and lipid metabolism. They also contribute to the transport and maturation of cellular proteins and are closely associated with several diseases. The important role of the cellular microenvironment in maintaining cellular homeostasis. Changes in cell polarity, particularly in organelles, have been found to be strongly linked to inflammation, Alzheimer's disease, cancer, and other illnesses. It is essential to check the polarity of the LDs. A series of arylated naphthalimide derivatives were synthesized using the Suzuki reaction. Modification of synthesized aryl naphthalimides using oligomeric PEG based on intramolecular charge transfer (ICT) mechanism. A series of fluorescent probes were designed to target LDs and detect their polarity. Nap-TPA-PEG probe exhibited high sensitivity to polarity. The addition of oligomeric polyethylene glycol (PEG) to the probe not only significantly improved its solubility in water, but also effectively reduced its cytotoxicity. In addition, the probe exhibited excellent aggregation-induced luminescence (AIE) properties and solvent discolouration effects. Nap-TPA-PEG probe exhibited high Pearson correlation coefficient (0.957163) in lipid droplet co-localization in cells. Nap-TPA-PEG could be used as an effective hand tool to monitor cell polarity.

摘要

脂滴(LDs)是动态的亚细胞细胞器,在能量平衡和脂质代谢中起着核心作用。它们还促进细胞蛋白质的运输和成熟,并与多种疾病密切相关。细胞微环境在维持细胞内稳态方面起着重要作用。细胞极性的变化,特别是细胞器的极性变化,与炎症、阿尔茨海默病、癌症等疾病密切相关。检查 LD 的极性非常重要。我们使用 Suzuki 反应合成了一系列芳基化萘酰亚胺衍生物。通过基于分子内电荷转移(ICT)机制的寡聚 PEG 对合成的芳基萘酰亚胺进行修饰。设计了一系列荧光探针来靶向 LD 并检测其极性。Nap-TPA-PEG 探针对极性具有高灵敏度。在探针中加入寡聚聚乙二醇(PEG)不仅显著提高了其在水中的溶解度,而且有效降低了其细胞毒性。此外,该探针表现出优异的聚集诱导发光(AIE)性质和溶剂变色效应。Nap-TPA-PEG 探针在细胞中脂滴共定位方面表现出高的皮尔逊相关系数(0.957163)。Nap-TPA-PEG 可作为监测细胞极性的有效工具。

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