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Enhancing the biocompatibility of rhodamine fluorescent probes by a neighbouring group effect
Chemical Science ( IF 7.6 ) Pub Date : 2020-06-22 , DOI: 10.1039/d0sc02154g Jonas Bucevičius 1 , Georgij Kostiuk 1 , Rūta Gerasimaitė 1 , Tanja Gilat 2 , Gražvydas Lukinavičius 1
Chemical Science ( IF 7.6 ) Pub Date : 2020-06-22 , DOI: 10.1039/d0sc02154g Jonas Bucevičius 1 , Georgij Kostiuk 1 , Rūta Gerasimaitė 1 , Tanja Gilat 2 , Gražvydas Lukinavičius 1
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Fluorescence microscopy is an essential tool for understanding dynamic processes in living cells and organisms. However, many fluorescent probes for labelling cellular structures suffer from unspecific interactions and low cell permeability. Herein, we demonstrate that the neighbouring group effect which results from positioning an amide group next to a carboxyl group in the benzene ring of rhodamines dramatically increases cell permeability of the rhodamine-based probes through stabilizing a fluorophore in a hydrophobic spirolactone state. Based on this principle, we create probes targeting tubulin, actin and DNA. Their superb staining intensity, tuned toxicity and specificity allows long-term 3D confocal and STED nanoscopy with sub-30 nm resolution. Due to their unrestricted cell permeability and efficient accumulation on the target, the new probes produce high contrast images at low nanomolar concentrations. Superior performance is exemplified by resolving the real microtubule diameter of 23 nm and selective staining of the centrosome inside living cells for the first time.
中文翻译：
通过邻基效应增强罗丹明荧光探针的生物相容性
荧光显微镜是了解活细胞和生物体动态过程的重要工具。然而，许多用于标记细胞结构的荧光探针存在非特异性相互作用和低细胞渗透性。在此，我们证明，将酰胺基置于罗丹明苯环中羧基旁边所产生的邻基效应，通过稳定疏水性螺内酯状态的荧光团，显着增加了基于罗丹明的探针的细胞渗透性。基于这一原理，我们创建了针对微管蛋白、肌动蛋白和 DNA 的探针。其卓越的染色强度、经过调节的毒性和特异性可实现分辨率低于 30 nm 的长期 3D 共聚焦和 STED 纳米镜检查。由于其不受限制的细胞渗透性和在目标上的有效积累，新探针可以在低纳摩尔浓度下产生高对比度图像。首次解析了 23 nm 的真实微管直径，并首次对活细胞内的中心体进行选择性染色，体现了卓越的性能。
更新日期：2020-07-22
中文翻译：
通过邻基效应增强罗丹明荧光探针的生物相容性
荧光显微镜是了解活细胞和生物体动态过程的重要工具。然而，许多用于标记细胞结构的荧光探针存在非特异性相互作用和低细胞渗透性。在此，我们证明，将酰胺基置于罗丹明苯环中羧基旁边所产生的邻基效应，通过稳定疏水性螺内酯状态的荧光团，显着增加了基于罗丹明的探针的细胞渗透性。基于这一原理，我们创建了针对微管蛋白、肌动蛋白和 DNA 的探针。其卓越的染色强度、经过调节的毒性和特异性可实现分辨率低于 30 nm 的长期 3D 共聚焦和 STED 纳米镜检查。由于其不受限制的细胞渗透性和在目标上的有效积累，新探针可以在低纳摩尔浓度下产生高对比度图像。首次解析了 23 nm 的真实微管直径，并首次对活细胞内的中心体进行选择性染色，体现了卓越的性能。
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