Novel meso-trifluoromethyl BODIPY-based near-infrared-emitting fluorescent probes for organelle-specific imaging of cellular viscosity
Novel meso-trifluoromethyl BODIPY-based near-infrared-emitting fluorescent probes for organelle-specific imaging of cellular viscosity
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DOI：
10.1016/j.snb.2022.131594
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发表时间：
2022-02
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通讯作者：
Wen-Jing Shi;Yong-Feng Wei;Jinrong Yang;Hui-Zhi Li;Q. Wan;Yuxuan Wang;Huaxiang Leng;Kun Chen;Jin-wu Yan
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文献类型：
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作者：
Wen-Jing Shi;Yong-Feng Wei;Jinrong Yang;Hui-Zhi Li;Q. Wan;Yuxuan Wang;Huaxiang Leng;Kun Chen;Jin-wu Yan
荧光分子转子在理解细胞粘度变化的功能方面起着至关重要的作用，其异常波动与许多疾病密切相关。尽管人们付出了大量的努力，但开发具有近红外荧光、高灵敏度和低背景的粘度探针仍然是一个紧迫而重要的课题。本论文首次报道了两种新型的单苯乙烯基硼二吡咯亚甲基（BODIPYs）化合物，其中间位带有可旋转的三氟甲基（CF 3），并带有三苯基膦（4）或吗啉（6）取代基，可作为高灵敏度的近红外荧光探针用于线粒体或溶酶体的细胞粘度成像。这些探针可以在温和条件下通过Knoevenagel缩合制备，并且在低粘度溶剂中显示出可忽略的排放。而在高粘度甘油中，由于CF 3基团的旋转受到限制，在657 nm处出现了较强的近红外荧光。在1-950 cP范围内，荧光强度（log I）与粘度（log η）呈良好的线性关系。酶靶向探针4的粘度检测限相对低于溶酶体靶向探针6。这些探针均显示无细胞毒性和良好的线粒体或溶酶体定位。有趣的是，靶向LPS或制霉菌素的探针4表现出显着的细胞内荧光增强与粘度增加，这是优于溶酶体靶向探针6。这两个新的基于BODIPY的荧光转子为开发近红外发射和细胞器特异性的细胞粘度荧光探针提供了新的策略，这可能有助于探索粘度在各种疾病中的功能。
Fluorescent molecular rotors play vital roles in understanding the function of cellular viscosity changes and its abnormal fluctuations are closely associated with many diseases. Despite numerous efforts spent, it remains an urgent and important topic to develop improved viscosity probes with near-infrared fluorescence, high sensitivity and low background. In this manuscript, for the first time, we reported two novel monostyryl boron dipyrromethenes (BODIPYs) bearing a rotatable trifluoromethyl group (CF3) at themesoposition and a triphenylphosphonium (4) or morpholine (6) substituent, which could successfully serve as highly sensitive and near-infrared-emitting fluorescent probes for imaging cellular viscosity in mitochondria or lysosome. These probes could be prepared through Knoevenagel condensation under mild conditions and showed negligible emissions in the low viscous solvents. However in high viscous glycerol, strong near-infrared fluorescence at 657 nm appeared, ascribed to the substantially restricted rotation of the CF3group. Their fluorescence intensity (log I) at 657 nm exhibited a good linear relationship with viscosity (log η) in the whole test range of 1–950 cP. Limit of detection for viscosity of mitochondria-targeting probe4was relatively lower than that of lysosome-targeting probe6. These probes both showed no cytotoxicity and good mitochondrial or lysosomal localization. Interestingly, mitochondria-targeting probe4exhibited a remarkable intracellular fluorescence enhancement with viscosity increase induced by LPS or nystatin, which was better than lysosome-targeting probe6. These two novel BODIPY-based fluorescent rotors provide a new strategy for developing near-infrared-emitting and organelle-specific fluorescent probes for cellular viscosity, which might be useful in exploring the functions of viscosity in various diseases.