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首页> 外文期刊>Chemistry: A European journal >Phosphorylated 3-heteroarylcoumarins and their use in fluorescence microscopy and nanoscopy
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Phosphorylated 3-heteroarylcoumarins and their use in fluorescence microscopy and nanoscopy

机译：磷酸化的3-杂芳基香豆素及其在荧光显微镜和纳米显微镜中的应用

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Photostable and bright fluorescent dyes with large Stokes shifts are widely used as markers in far-field optical microscopy, but the variety of useful dyes is limited. The present study introduces new 3-heteroaryl coumarins decorated with a primary phosphate group (OP(O)(OH)_2) attached to C-4 in 2,2,4-trimethyl-1,2-dihydroquinoline fragment fused with the coumarin fluorophore. The general synthetic route is based on the Suzuki reaction of 3-bromocoumarines with hetarylboronic acids followed by oxidation of the methyl group at the C?￡C bond with SeO_2 (to an aldehyde), reduction with NaBH_4 (to an alcohol), and conversion into a primary phosphate. The 4 position in the coumarin system may be unsubstituted or bear a methyl group. Phosphorylated coumarins were found to have high fluorescence quantum yields in the free state and after conjugation with proteins (in aqueous buffers). In super-resolution light microscopy with stimulated emission depletion (STED), the new coumarin dyes provide an optical resolution of 40-60nm with a low background signal. Due to their large Stokes shifts and high photostability, phosphorylated coumarins enable to combine multilabel imaging (using one detector and several excitation sources) with diffraction unlimited optical resolution. A green light for bright ideas! 3-Heteroarylcoumarins with a CH_2OP(O)(OH)_2 group attached to the 2,2,4-trimethyl-1,2- dihydroquinoline residue absorb at 410-440nm and emit at 500-515nm (see figure). Large fluorescence quantum yields and low cross-talk in two-color imaging (with xanthene dyes) were observed. In stimulated emission depletion (STED) nanoscopy, these phosphorylated dyes with large Stokes shifts allow an optical resolution of 40-60nm.
机译：具有大斯托克斯位移的光稳定和明亮的荧光染料被广泛用作远场光学显微镜的标记，但是有用染料的种类受到限制。本研究介绍了新的3-杂芳基香豆素，其装饰有与香豆素荧光团融合的2,2,4-三甲基-1,2-二氢喹啉片段中与C-4相连的伯磷酸基（OP（O）（OH）_2） 。一般的合成路线是基于3-溴香豆素与杂芳基硼酸的Suzuki反应，然后用SeO_2将C？C键上的甲基氧化（成醛），用NaBH_4还原（成醇），然后转化变成初级磷酸盐。香豆素体系中的4位可以是未取代的或带有甲基。发现磷酸化的香豆素在游离态和与蛋白质结合后（在水性缓冲液中）具有高荧光量子产率。在具有激发发射损耗（STED）的超高分辨率光学显微镜中，新型香豆素染料具有40-60nm的光学分辨率，且背景信号低。由于其大的斯托克斯位移和高光稳定性，磷酸化香豆素能够将多标签成像（使用一个检测器和多个激发源）与无限衍射的光学分辨率结合起来。绿灯亮点！连接到2,2,4-三甲基-1,2-二氢喹啉残基的CH_2OP（O）（OH）_2基团的3-杂芳基香豆素在410-440nm处吸收并在500-515nm处发射（见图）。在双色成像（使用x吨染料）中观察到大的荧光量子产率和低串扰。在激发发射耗尽（STED）显微镜下，这些具有大斯托克斯位移的磷酸化染料可实现40-60nm的光学分辨率。

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