Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University in Bratislava, Ilkovičova 6, 842 15, Bratislava, Slovakia.
Department of Chemistry, University of Zurich, Wintherthurerstrasse 190, 8057, Zurich, Switzerland.
Chemistry. 2024 May 17;30(28):e202400111. doi: 10.1002/chem.202400111. Epub 2024 Apr 2.
Regulation of pH plays an essential role in orchestrating the delicate cellular machinery responsible for life as we know it. Its abnormal values are indicative of aberrant cellular behavior and associated with pathologies including cancer progression or solid tumors. Here, we report a series of bent and linear aminobenzocoumarins decorated with different substituents. We investigate their photophysical properties and demonstrate that the probes display strong pH-responsive fluorescence "turn on" behavior in highly acidic environments, with enhancement up to 300-fold. In combination with their low cytotoxicity, this behavior enabled their application in bioimaging of acidic lysosomes in live human cells. We believe that these molecules serve as attractive lead structures for future rational design of novel biocompatible fluorescent pH probes.
pH 值的调节在协调负责我们所熟知的生命的精细细胞机制方面起着至关重要的作用。其异常值表明细胞行为异常，并与包括癌症进展或实体瘤在内的病理学相关。在这里，我们报告了一系列带有不同取代基的弯曲和线性氨基苯并香豆素。我们研究了它们的光物理性质，并证明这些探针在高度酸性环境中表现出强烈的 pH 响应荧光“开启”行为，增强高达 300 倍。结合其低细胞毒性，这种行为使它们能够应用于活人类细胞中酸性溶酶体的生物成像。我们相信这些分子可以作为未来设计新型生物相容性荧光 pH 探针的有吸引力的先导结构。
