Analyte-Triggered Excited-State Intramolecular Proton Transfer-Delayed Fluorescence: A General Approach for Time-Resolved Turn-On Fluorescence Imaging
Analyte-Triggered Excited-State Intramolecular Proton Transfer-Delayed Fluorescence: A General Approach for Time-Resolved Turn-On Fluorescence Imaging
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DOI：
10.1021/acs.analchem.3c00827
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发表时间：
2023-05-01
影响因子：
7.4
通讯作者：
Hu，Hai-Yu
中科院分区：
文献类型：
--
作者：
Han，Xiaowan;Meng，Xiangchuan;Hu，Hai-Yu
延迟荧光的研究一直是生物成像领域的研究热点。然而，分析物触发的小分子DF探针的开发仍然是一个相当大的挑战。本文报道了一种新的激发态分子内质子转移延迟荧光(ESIPT-DF)方法来构建分析物刺激的分子内质子转移延迟荧光探针。这些新型的ESIPT-DF发光体是通过将已知的基于ESIPT的荧光团2-(2‘-羟基苯基)苯并噻唑(HBT)作为受体与一系列经典的给体部分结合在一起而设计和合成的，在每个分子中形成了相应的扭曲的给体-受体对。其中，HBT-PXZ和HBT-PTZ在固体中表现出明显的ESIPT和DF特性，其寿命分别为5.37μ和3.65μS。此外，通过引入亲水性半乳糖基团作为β-半乳糖苷酶(β-GAL)和封闭剂的特异性识别单元，制备了笼式探针HBT-PXZ-GA，并作为一种方便的工具应用于研究金属离子对肺炎链球菌表面β-GAL活性的影响。这种ESIPT-DF“开启”方法很容易适用于许多不同分析物的测量，只需对笼状基团进行可预测的修改，而不需要修改核心结构。
The research of delayed fluorescence (DF) has been a hot topic in biological imaging. However, the development of analyte-triggered small molecule DF probes remains a considerable challenge. Herein a novel excited-state intramolecular proton transfer-delayed fluorescence (ESIPT-DF) approach to construct analyte-stimulated DF probes was reported. These new classes of ESIPT-DF luminophores were strategically designed and synthesized by incorporating 2-(2′-hydroxyphenyl)benzothiazole (HBT), a known ESIPT-based fluorophore, as acceptor with a series of classic donor moieties, which formed a correspondingly twisted donor–acceptor pair within each molecule. Thereinto,HBT-PXZandHBT-PTZexhibited significant ESIPT and DF characters with lifetimes of 5.37 and 3.65 μs in the solid state, respectively. Furthermore, a caged probeHBT-PXZ-Gawas developed by introducing a hydrophilicd-galactose group as the recognition unit specific for β-galactosidase (β-gal) and ESIPT-DF blocking agent and applied to investigate the influence of metal ions on β-gal activity on the surface ofStreptococcus pneumoniaeas a convenient tool. This ESIPT-DF “turn-on” approach is easily adaptable for the measurement of many different analytes using only a predictable modification on the caged group without modification of the core structure.