Development of N,O-benzamide borondifluoride-based lipid droplets-targeting fluorescent probes for fatty liver identification

IF 4.2 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments Pub Date : 2025-06-17 DOI:10.1016/j.dyepig.2025.112967

Yang Liu , Yixin Zhang , Shuo He , Yufo Chen , Shanshan Zhang , Meng Wang , Rui Wang , Wuyu Mao , Zishu Wang

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引用次数: 0

Abstract

The abnormal accumulation of lipid droplets in hepatocytes under stress is closely associated with nonalcoholic fatty liver disease (NAFLD). To evaluate lipid droplets (LDs) in pathological conditions, we developed four far-red/near-infrared boron difluoride (BF₂) probes with large Stokes shifts. These probes can be modularly synthesized from N,O-benzamide BF₂-bridged electron acceptors. The fluorescence properties of these molecules display distinct solvatochromic behavior. Notably, BAF-1 and BAF-2 show notable sensitivity to variations in solvent polarity, and the high fluorescence intensity in the low-polarity solvents such as 1,4-dioxane. In particular, BAF-1 demonstrates optimal Clog P, specific targeting of LDs and excellent photostability in living cells. Through confocal imaging, we identified the BAF-1 is able to detect the polarity changes and dynamically monitor the interaction of LDs. BAF-1 has been utilized to detect the changes of LDs between normal and fatty liver conditions. Confocal images of frozen tissue sections revealed an ultrahigh contrast (up to 160-fold) in LDs accumulation within the liver microenvironment of NAFLD mice. Consequently, the BF₂-based probe BAF-1 demonstrates potential as a tool for investigating the biological functions of LDs and for facilitating precise diagnosis of fatty liver disease.

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基于N， o -苯甲酰胺二氟硼的脂滴靶向荧光探针用于脂肪肝鉴定

应激状态下肝细胞脂滴的异常积聚与非酒精性脂肪性肝病（NAFLD）密切相关。为了评估病理条件下的脂滴（ld），我们开发了四种远红/近红外二氟化硼（BF2）探针，具有较大的Stokes位移。这些探针可以由N， o -苯甲酰胺bf2桥接电子受体模块化合成。这些分子的荧光性质表现出明显的溶剂致变色行为。值得注意的是，BAF-1和BAF-2对溶剂极性变化表现出显著的敏感性，并且在低极性溶剂（如1,4-二恶烷）中具有较高的荧光强度。特别是，BAF-1在活细胞中表现出最佳的Clog P，特异性靶向ld和出色的光稳定性。通过共聚焦成像，我们发现BAF-1能够检测极性变化并动态监测ld的相互作用。BAF-1已被用于检测正常和脂肪肝之间ld的变化。冷冻组织切片的共聚焦图像显示NAFLD小鼠肝脏微环境内ld积累的超高对比度（高达160倍）。因此，基于bf2的探针BAF-1显示了作为研究ld生物学功能和促进脂肪肝疾病精确诊断工具的潜力。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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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.