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首页> 外文期刊>Chemistry: A European journal >New fluorinated rhodamines for optical microscopy and nanoscopy
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New fluorinated rhodamines for optical microscopy and nanoscopy

机译：用于光学显微镜和纳米显微镜检查的新型氟化罗丹明

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摘要

New photostable rhodamine dyes represented by the compounds 1a-r and 3-5 are proposed as efficient fluorescent markers with unique combination of structural features. Unlike rhodamines with monoalkylated nitrogen atoms, N′,N-bis(2,2,2-trifluoroethyl) derivatives 1e, 1i, 1j, 3-H and 5 were found to undergo sulfonation of the xanthene fragment at the positions 4′ and 5′. Two fluorine atoms were introduced into the positions 2′ and 7′ of the 3′,6′-diaminoxanthene fragment in compounds 1a-d, 1i-l and 1m-r. The new rhodamine dyes may be excited with λ= 488 or 514 nm light; most of them emit light at λ = 512-554 nm (compounds 1q and 1r at λ=576 and 589 nm in methanol, respectively) and have high fluorescence quantum yields in solution (up to 98%), relatively long excited-state lifetimes (>3ns) and are resistant against photobleaching, especially at high laser intensities, as is usually applied in confocal microscopy. Sulfonation of the xanthene fragment with 30% SO_3 in H_2SO_4 is compatible with the secondary amide bond (rhodamine-CON(Me)CH_2CH _2COOH) formed with MeNHCH_2CH_2COOCH_3 to providing the sterically unhindered carboxylic group required for further (bio)conjugation reactions. After creating the amino reactive sites, the modified derivatives may be used as fluorescent markers and labels for (bio)molecules in optical microscopy and nanoscopy with very-high light intensities. Further, the new rhodamine dyes are able to pass the plasma membrane of living cells, introducing them as potential labels for recent live-cell-tag approaches. We exemplify the excellent performance of the fluorinated rhodamines in optical microscopy by fluorescence correlation spectroscopy (FCS) and stimulated emission depletion (STED) nanoscopy experiments.
机译：提出了由化合物1a-r和3-5代表的新型光稳定的若丹明染料，作为具有独特结构特征的有效荧光标记。与具有单烷基化氮原子的罗丹明不同，发现N'，N-双（2,2,2-三氟乙基）衍生物1e，1i，1j，3-H和5在位置4'和5发生the吨片段的磺化反应'。将两个氟原子引入化合物1a-d，1i-1和1m-r中3'，6'-二氨基amino吨片段的2'和7'位置。新的若丹明染料可能会被λ= 488或514 nm的光激发。它们中的大多数在λ= 512-554 nm处发光（在甲醇中分别在λ= 576和589 nm处的化合物1q和1r），并且溶液中的荧光量子产率高（高达98％），激发态寿命较长（> 3ns），并且对光漂白具有抵抗力，尤其是在高激光强度下，通常在共聚焦显微镜中应用。在H_2SO_4中用30％SO_3进行的3吨片段的磺化与由MeNHCH_2CH_2COOCH_3形成的仲酰胺键（若丹明-CON（Me）CH_2CH _2COOH）相容，可提供进一步的（生物）共轭反应所需的空间不受阻碍的羧基。在产生氨基反应位点之后，该修饰的衍生物可以用作具有非常高的光强度的光学显微镜和纳米显微镜中的（生物）分子的荧光标记和标记。此外，新的若丹明染料能够通过活细胞的质膜，将它们作为最近的活细胞标记方法的潜在标记。我们通过荧光相关光谱（FCS）和受激发射损耗（STED）纳米显微镜实验，举例说明了氟化罗丹明在光学显微镜中的出色性能。

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