The Education Ministry Key Laboratory of Resource Chemistry, Shanghai Key Laboratory of Rare Earth Functional Materials, and Shanghai Municipal Education Committee Key Laboratory of Molecular Imaging Probes and Sensors, Department of Chemistry, Shanghai Normal University, 100 Guilin Road, Shanghai 200234, China.
J Mater Chem B. 2019 Oct 7;7(37):5633-5639. doi: 10.1039/c9tb01671f. Epub 2019 Sep 4.
2,4-Dinitrobenzenesulfonyl (DNBS) has been widely used for the design of small fluorescent probes for biothiols due to its high reactivity. However, most DNBS-based fluorescent probes exhibit "off-on" fluorescence response towards biothiols due to the strong quenching effects of DBNS on the fluorophores. Herein, we present an alternative design of a ratiometric fluorescent probe based on DNBS for biothiols. A new fluorophore bearing two isophorone malononitrile structures was conjugated with DNBS to provide a target probe (CHT), which exhibited a ratiometric sensing behavior towards biothiols. The sensing process is rapid and highly selective. Most importantly, CHT has high stability in the quantitative detection of Cys compared to the control probe CHM, which performed an "off-on" sensing for biothiols. Endogenous biothiols were successfully monitored with CHT in live cells through the ratiometric fluorescence signal. This new fluorophore bearing two isophorone malononitrile moieties will pave a new avenue to design ratiometric fluorescent probes for imaging and quantitative detection.
2,4-二硝基苯磺酰基 (DNBS) 由于其高反应性而被广泛用于设计用于生物硫醇的小型荧光探针。然而，由于 DBNS 对荧光团的强烈猝灭作用，大多数基于 DNBS 的荧光探针对生物硫醇表现出“关-开”荧光响应。在此，我们提出了一种基于 DNBS 的比率型荧光探针的替代设计，用于生物硫醇。带有两个异佛尔酮丙二腈结构的新荧光团与 DNBS 缀合，提供了目标探针 (CHT)，其对生物硫醇表现出比率型传感行为。传感过程快速且高度选择性。最重要的是，与表现出“关-开”传感的对照探针 CHM 相比，CHT 在 Cys 的定量检测中具有更高的稳定性。通过比率荧光信号，CHT 成功地在活细胞中监测到内源性生物硫醇。带有两个异佛尔酮丙二腈部分的这种新荧光团将为设计用于成像和定量检测的比率型荧光探针开辟新途径。
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