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一种基于邻位肟功能化苝二酰亚胺的新型比率荧光探针,用于细胞和斑马鱼中超灵敏的HClO/ClO识别及生物成像。

A Novel Ratiometric Fluorescent Probe Based on Ortho-Position Oxime Functionalized Perylene Diimide for Supersensitive HClO/ClO Recognition and Bioimaging in Cells and Zebrafish.

作者信息

Shi Ruida, Sun Chengcheng, Zhang Tieshan, Li Shiyin, Zuo Yujing, Yu Haitao, Qi Yanyu

机构信息

Hebei Key Laboratory of Organic Functional Molecules, Hebei Engineering Research Center of Thin Film Solar Cell Materials and Devices, College of Chemistry and Materials Science, Hebei Normal University, Shijiazhuang 050024, China.

School of Chemistry and Chemical Engineering, School of Materials Science and Engineering, University of Jinan, Jinan, Shandong 250022, China.

出版信息

Anal Chem. 2025 Jul 29;97(29):16079-16088. doi: 10.1021/acs.analchem.5c03768. Epub 2025 Jul 20.

DOI:10.1021/acs.analchem.5c03768
PMID:40685583
Abstract

Hypochlorous acid (HClO) or hypochlorite (ClO) not only is a common weak acid in daily life but also serves as a disinfectant and a key component of bleaching powder. Simultaneously, HClO/ClO can also participate in many pathological processes as a kind of reactive oxygen species. To address the limitations in HClO/ClO detection, we developed , an ultrasensitive, rapid-response, and highly selective fluorescent probe, through rational molecular engineering of a perylene diimide scaffold and oxime as the recognition site. We systematically evaluated the photophysical properties and HClO/ClO response performance of through comprehensive spectral characterization. The probe demonstrates remarkable analytical metrics: (1) dual detection modes by UV-vis and fluorescence; (2) ultrahigh sensitivity with a subnanomolar detection limit (5 pM); (3) exceptional selectivity and anti-interference ability against 16 common interferences, including ions and reactive oxygen/nitrogen analogs; (4) rapid response speed (7.5 s); (5) wide linear range (0-8.0 μΜ); and (6) convenient visual detection toward smartphone-based RGB analysis. Notably, exhibits dual-function bioimaging capabilities: it enables real-time discrimination of live/dead mammalian cells while achieving zebrafish larval imaging of HClO/ClO. This novel ratiometric fluorescent probe establishes a new paradigm for developing precision biosensors to unravel hypochlorite-related pathophysiological cascades.

摘要

次氯酸(HClO)或次氯酸盐(ClO)不仅是日常生活中常见的弱酸,还用作消毒剂和漂白粉的关键成分。同时,HClO/ClO作为一种活性氧,也可参与许多病理过程。为解决HClO/ClO检测方面的局限性,我们通过对苝二酰亚胺支架和肟作为识别位点进行合理的分子工程设计,开发了一种超灵敏、快速响应且高选择性的荧光探针。我们通过全面的光谱表征系统地评估了该探针的光物理性质和HClO/ClO响应性能。该探针展示出卓越的分析指标:(1)紫外可见和荧光双检测模式;(2)具有亚纳摩尔检测限(5 pM)的超高灵敏度;(3)对包括离子和活性氧/氮类似物在内的16种常见干扰物具有出色的选择性和抗干扰能力;(4)快速响应速度(7.5秒);(5)宽线性范围(0 - 8.0 μΜ);(6)基于智能手机RGB分析的便捷可视化检测。值得注意的是,该探针具有双功能生物成像能力:它能够实时区分活/死哺乳动物细胞,同时实现对HClO/ClO的斑马鱼幼体成像。这种新型比率荧光探针为开发精密生物传感器以揭示次氯酸盐相关的病理生理级联反应建立了新的范例。

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