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Turn-on Fluorene Push–Pull Probes with High Brightness and Photostability for Visualizing Lipid Order in Biomembranes
ACS Chemical Biology ( IF 4 ) Pub Date : 2017-11-08 00:00:00 , DOI: 10.1021/acschembio.7b00658
Janah Shaya 1 , Mayeul Collot 2 , Frédéric Bénailly 1 , Najiba Mahmoud 1 , Yves Mély 2 , Benoît Y. Michel 1 , Andrey S. Klymchenko 2 , Alain Burger 1
Affiliation  

The rational design of environmentally sensitive dyes with superior properties is critical for elucidating the fundamental biological processes and understanding the biophysical behavior of cell membranes. In this study, a novel group of fluorene-based push–pull probes was developed for imaging membrane lipids. The design of these fluorogenic conjugates is based on a propioloyl linker to preserve the required spectroscopic features of the core dye. This versatile linker allowed the introduction of a polar deoxyribosyl head, a lipophilic chain, and an amphiphilic/anchoring group to tune the cell membrane binding and internalization. It was found that the deoxyribosyl head favored cell internalization and staining of intracellular membranes, whereas an amphiphilic anchor group ensured specific plasma membrane staining. The optimized fluorene probes presented a set of improvements as compared to commonly used environmentally sensitive membrane probe Laurdan such as red-shifted absorption matching the 405 nm diode laser excitation, a blue-green emission range complementary to the red fluorescent proteins, enhanced brightness and photostability, as well as preserved sensitivity to lipid order, as shown in model membranes and living cells.

中文翻译:

具有高亮度和光稳定性的开启式芴推挽式探针,可用于可视化生物膜中的脂质顺序

具有优良性能的对环境敏感的染料的合理设计对于阐明基本的生物学过程和理解细胞膜的生物物理行为至关重要。在这项研究中,开发了一组新的基于芴的推挽式探针,用于对膜脂质进行成像。这些荧光共轭物的设计基于丙腈基接头,以保留核心染料所需的光谱特征。这种通用的接头允许引入极性的脱氧核糖基团头部,亲脂性链和两亲性/锚定基团,以调节细胞膜的结合和内在化。发现脱氧核糖基团的头部有利于细胞内化和细胞内膜的染色,而两亲性锚基团确保特定的质膜染色。
更新日期:2017-11-09
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