Systematic Tuning of Rhodamine Spirocyclization for Super-resolution Microscopy,Journal of the American Chemical Society

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Systematic Tuning of Rhodamine Spirocyclization for Super-resolution Microscopy
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2021-08-30 , DOI: 10.1021/jacs.1c05004
Nicolas Lardon _{1,

2} , Lu Wang _{1,

3} , Aline Tschanz _{4,

5} , Philipp Hoess _{4,

5} , Mai Tran ₁ , Elisa D'Este ₆ , Jonas Ries ₄ , Kai Johnsson _{1,

7}

Affiliation

Rhodamines are the most important class of fluorophores for applications in live-cell fluorescence microscopy. This is mainly because rhodamines exist in a dynamic equilibrium between a fluorescent zwitterion and a nonfluorescent but cell-permeable spirocyclic form. Different imaging applications require different positions of this dynamic equilibrium, and an adjustment of the equilibrium poses a challenge for the design of suitable probes. We describe here how the conversion of the ortho-carboxy moiety of a given rhodamine into substituted acyl benzenesulfonamides and alkylamides permits the systematic tuning of the equilibrium of spirocyclization with unprecedented accuracy and over a large range. This allows one to transform the same rhodamine into either a highly fluorogenic and cell-permeable probe for live-cell-stimulated emission depletion (STED) microscopy or a spontaneously blinking dye for single-molecule localization microscopy (SMLM). We used this approach to generate differently colored probes optimized for different labeling systems and imaging applications.

中文翻译：

用于超分辨率显微镜的罗丹明螺环化的系统调谐

罗丹明是活细胞荧光显微镜应用中最重要的一类荧光团。这主要是因为罗丹明存在于荧光两性离子和非荧光但细胞可渗透的螺环形式之间的动态平衡中。不同的成像应用需要这种动态平衡的不同位置，平衡的调整对设计合适的探头提出了挑战。我们在这里描述了正交的转换将给定罗丹明的羧基部分转化为取代的酰基苯磺酰胺和烷基酰胺，可以以前所未有的精度和大范围系统地调整螺环化平衡。这允许将相同的罗丹明转化为用于活细胞刺激发射损耗 (STED) 显微镜的高荧光和细胞渗透性探针或用于单分子定位显微镜 (SMLM) 的自发闪烁染料。我们使用这种方法来生成针对不同标记系统和成像应用优化的不同颜色的探针。

更新日期：2021-09-15

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