National Nanotechnology Center, National Science and Technology Development Agency, Thailand Science Park, Pathum Thani 12120, Thailand.
School of Chemistry, Institute of Science, Suranaree University of Technology, Nakhon Ratchasima 30000, Thailand.
Biosensors (Basel). 2022 Oct 25;12(11):923. doi: 10.3390/bios12110923.
In this work, the two pyridylhydrazone-tethered BODIPY compounds ( and ) were synthesized. These compounds aimed to detect hypochlorous acid (HOCl) species via cyclic triazolopyridine formation. The open forms and the resulting cyclic forms of BODIPYs (, , , and ) were fully characterized by nuclear magnetic resonance, mass spectrometry, infrared spectroscopy, and single-crystal X-ray diffraction. These two probes can selectively detect HOCl through a fluorescence turn-on mechanism with the limit of detections of 0.21 µM and 0.77 µM for compounds and , respectively. This fluorescence enhancement phenomenon could be the effect from C = N isomerization inhibition due to HOCl-triggered triazolopyridine formation. In cell imaging experiments, these compounds showed excellent biocompatibility toward RAW 264.7 murine live macrophage cells and greatly visualized endogenous HOCl in living cells stimulated with lipopolysaccharide.
在这项工作中，合成了两个吡啶基腙键合的 BODIPY 化合物（和）。这些化合物旨在通过环三唑并吡啶形成来检测次氯酸（HOCl）物种。BODIPY 的开环形式和所得的环状形式（、、、和）通过核磁共振、质谱、红外光谱和单晶 X 射线衍射得到了充分的表征。这两种探针可以通过荧光开启机制选择性地检测 HOCl，化合物和的检测限分别为 0.21 µM 和 0.77 µM。这种荧光增强现象可能是由于 HOCl 触发三唑并吡啶形成导致 C=N 异构化抑制的结果。在细胞成像实验中，这些化合物对 RAW 264.7 鼠原代巨噬细胞表现出良好的生物相容性，并在用脂多糖刺激的活细胞中很好地可视化了内源性 HOCl。
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