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ExTzBox: A Glowing Cyclophane for Live-Cell Imaging
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2018-05-17 , DOI: 10.1021/jacs.8b03066 Indranil Roy , Sharan Bobbala , Jiawang Zhou , Minh T. Nguyen , Siva Krishna Mohan Nalluri , Yilei Wu , Daniel P. Ferris , Evan Alexander Scott , Michael R. Wasielewski , J. Fraser Stoddart 1
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2018-05-17 , DOI: 10.1021/jacs.8b03066 Indranil Roy , Sharan Bobbala , Jiawang Zhou , Minh T. Nguyen , Siva Krishna Mohan Nalluri , Yilei Wu , Daniel P. Ferris , Evan Alexander Scott , Michael R. Wasielewski , J. Fraser Stoddart 1
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The ideal fluorescent probe for live-cell imaging is bright and non-cytotoxic and can be delivered easily into the living cells in an efficient manner. The design of synthetic fluorophores having all three of these properties, however, has proved to be challenging. Here, we introduce a simple, yet effective, strategy based on well-established chemistry for designing a new class of fluorescent probes for live-cell imaging. A box-like hybrid cyclophane, namely ExTzBox·4X (6·4X, X = PF6-, Cl-), has been synthesized by connecting an extended viologen (ExBIPY) and a dipyridyl thiazolothiazole (TzBIPY) unit in an end-to-end fashion with two p-xylylene linkers. Photophysical studies show that 6·4Cl has a quantum yield ΦF = 1.00. Furthermore, unlike its ExBIPY2+ and TzBIPY2+ building units, 6·4Cl is non-cytotoxic to RAW 264.7 macrophages, even with a loading concentration as high as 100 μM, presumably on account of its rigid box-like structure which prevents its intercalation into DNA and may inhibit other interactions with it. After gaining an understanding of the toxicity profile of 6·4Cl, we employed it in live-cell imaging. Confocal microscopy has demonstrated that 64+ is taken up by the RAW 264.7 macrophages, allowing the cells to glow brightly with blue laser excitation, without any hint of photobleaching or disruption of normal cell behavior under the imaging conditions. By contrast, the acyclic reference compound Me2TzBIPY·2Cl (4·2Cl) shows very little fluorescence inside the cells, which is quenched completely under the same imaging conditions. In vitro cell investigations underscore the significance of using highly fluorescent box-like rigid cyclophanes for live-cell imaging.
中文翻译：
ExTzBox：用于活细胞成像的发光回旋管
用于活细胞成像的理想荧光探针是明亮且无细胞毒性的，并且可以以有效的方式轻松传递到活细胞中。然而，具有所有这三种特性的合成荧光团的设计已被证明具有挑战性。在这里，我们介绍了一种基于成熟化学的简单而有效的策略，用于设计一类用于活细胞成像的新型荧光探针。盒状杂环芳烃，即 ExTzBox·4X (6·4X, X = PF6-, Cl-)，已通过将扩展紫精 (ExBIPY) 和二吡啶基噻唑并噻唑 (TzBIPY) 单元连接到端对 -带有两个对二甲苯连接体的末端时尚。光物理研究表明6·4Cl 的量子产额ΦF = 1.00。此外，与 ExBIPY2+ 和 TzBIPY2+ 构建单元不同，6·4Cl 对 RAW 264.7 巨噬细胞无细胞毒性，即使负载浓度高达 100 μM，大概是因为其刚性盒状结构可防止其嵌入 DNA 并可能抑制与其的其他相互作用。在了解了 6·4Cl 的毒性特征后，我们将其用于活细胞成像。共聚焦显微镜已经证明 64+ 被 RAW 264.7 巨噬细胞吸收，使细胞在蓝色激光激发下发出明亮的光，在成像条件下没有任何光漂白或正常细胞行为中断的迹象。相比之下，无环参考化合物 Me2TzBIPY·2Cl (4·2Cl) 在细胞内显示出非常少的荧光，在相同的成像条件下完全淬灭。
更新日期：2018-05-17
中文翻译：
ExTzBox：用于活细胞成像的发光回旋管
用于活细胞成像的理想荧光探针是明亮且无细胞毒性的，并且可以以有效的方式轻松传递到活细胞中。然而，具有所有这三种特性的合成荧光团的设计已被证明具有挑战性。在这里，我们介绍了一种基于成熟化学的简单而有效的策略，用于设计一类用于活细胞成像的新型荧光探针。盒状杂环芳烃，即 ExTzBox·4X (6·4X, X = PF6-, Cl-)，已通过将扩展紫精 (ExBIPY) 和二吡啶基噻唑并噻唑 (TzBIPY) 单元连接到端对 -带有两个对二甲苯连接体的末端时尚。光物理研究表明6·4Cl 的量子产额ΦF = 1.00。此外，与 ExBIPY2+ 和 TzBIPY2+ 构建单元不同，6·4Cl 对 RAW 264.7 巨噬细胞无细胞毒性，即使负载浓度高达 100 μM，大概是因为其刚性盒状结构可防止其嵌入 DNA 并可能抑制与其的其他相互作用。在了解了 6·4Cl 的毒性特征后，我们将其用于活细胞成像。共聚焦显微镜已经证明 64+ 被 RAW 264.7 巨噬细胞吸收，使细胞在蓝色激光激发下发出明亮的光，在成像条件下没有任何光漂白或正常细胞行为中断的迹象。相比之下，无环参考化合物 Me2TzBIPY·2Cl (4·2Cl) 在细胞内显示出非常少的荧光，在相同的成像条件下完全淬灭。
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