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基于二氰异佛尔酮的近红外荧光探针,具有大斯托克斯位移,用于次氯酸盐的监测和生物成像。

Dicyanoisophorone-based near-infrared fluorescent probe with large Stokes shift for the monitoring and bioimaging of hypochlorite.

机构信息

Key Laboratory of Optic-electric Sensing and Analytical Chemistry for Life Science, MOE, Shandong Provincial Key Laboratory of Biochemical Engineering, Qingdao Nucleic Acid Rapid Detection Engineering Research Center, College of Marine Science and Biological Engineering, Qingdao University of Science and Technology, Qingdao, 266042, China.

Key Laboratory of Optic-electric Sensing and Analytical Chemistry for Life Science, MOE, Shandong Provincial Key Laboratory of Biochemical Engineering, Qingdao Nucleic Acid Rapid Detection Engineering Research Center, College of Marine Science and Biological Engineering, Qingdao University of Science and Technology, Qingdao, 266042, China; School of Chemistry and Life Science, Anshan Normal University, Liaoning Key Laboratory of Development and Utilization for Natural Products Active Molecules, Anshan, 114007, China.

出版信息

Talanta. 2024 Jul 1;274:126063. doi: 10.1016/j.talanta.2024.126063. Epub 2024 Apr 5.

Abstract

Hypochlorite (ClO), as one of reactive oxygen species (ROS), is closely linked to various illnesses and is essential for the proper functioning of immune system. Hence, monitoring and assessing ClO levels in organisms are extremely important for the clinical diagnosis of ClO-related disorders. In this study, a novel ClO-selective fluorescent probe, DCP-ClO, was synthesized with dicyanoisophorone-xanthene unit as parent fluorophore, which displayed excellent selectivity towards ClO, near-infrared emission (755 nm), large Stokes shift (100 nm), real-time response to ClO, high sensitivity (LOD = 3.95 × 10 M), and low cytotoxicity. The recognition mechanism of DCP-ClO towards ClO was confirmed to be a typical ICT process by HPLC-MS, HR-MS, H NMR and theoretical calculations. Meanwhile, DCP-ClO demonstrated remarkable efficacy in monitoring ClO levels in water samples and eye-catching ability in imaging endogenous/exogenous ClO in living organisms, which verified its potential as a powerful tool for the recognition of ClO in complex biological systems.

摘要

次氯酸根(ClO)作为活性氧(ROS)的一种,与各种疾病密切相关,是免疫系统正常运作所必需的。因此,监测和评估生物体中的 ClO 水平对于 ClO 相关疾病的临床诊断至关重要。在这项研究中,我们合成了一种新型的 ClO 选择性荧光探针 DCP-ClO,其母体荧光团为二氰异佛尔酮-呫吨单元,对 ClO 具有优异的选择性、近红外发射(755nm)、大斯托克斯位移(100nm)、对 ClO 的实时响应、高灵敏度(LOD=3.95×10-7M)和低细胞毒性。通过 HPLC-MS、HR-MS、1H NMR 和理论计算证实了 DCP-ClO 对 ClO 的识别机制是一种典型的 ICT 过程。同时,DCP-ClO 在水样中监测 ClO 水平方面表现出显著的效果,在成像活体内源性/外源性 ClO 方面具有引人注目的能力,验证了其作为一种在复杂生物系统中识别 ClO 的有力工具的潜力。

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