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偶氮蒽核心结构作为 Cu 辅助的 CO 传感探针:表征、性能和生物成像。

Azoanthracene-core structure as Cu-assisted CO sensing probe: Characterization, performance, and bioimaging.

机构信息

Provincial Key Laboratory for Gene Diagnosis of Cardiovascular Disease, Jilin Provincial Engineering Laboratory for Endothelial Function and Genetic Diagnosis, Department of Cardiology, China-Japan Union Hospital of Jilin University, Changchun, China.

Department of Laboratory, China-Japan Union Hospital of Jilin University, Changchun, China.

出版信息

Spectrochim Acta A Mol Biomol Spectrosc. 2024 May 15;313:124122. doi: 10.1016/j.saa.2024.124122. Epub 2024 Mar 5.

DOI:10.1016/j.saa.2024.124122
PMID:38479230
Abstract

Detection of endogenous CO (carbon monoxide) is an interesting topic in biology because it has been discovered as a messenger for signal transduction and therapeutic effects in vital biological activities. Fluorescence imaging has proven a powerful tool for detecting endogenous CO, which drives the development of low-cost and easy-to-use fluorescent probes. In this study, four azobenzene derivatives (A1, A2, A3, and A4) with various substituents were reported, including their geometric structures, photophysical parameters, and spectral responses to Cu and CO. The relationship between substituent structure and performance was discussed along with Cu quenching and CO sensing mechanisms. The optimal probe (A1), which had no substituent, efficiently quenched fluorescence in the presence of Cu, with its PLQY decreased from 0.33 to 0.02, PLQY = photoluminescence quantum yield. Upon CO deoxidization, A1's fluorescence could be recovered (PLQY recovered to 0.32) within 180 s. Its sensing mechanism was static by forming a non-fluorescent complex with Cu (with a stoichiometric ratio of 1:1). The bioimaging performance of A1 for endogenous CO in HeLa cells was reported.

摘要

内源性 CO(一氧化碳)的检测在生物学中是一个有趣的课题,因为它已被发现作为信号转导和重要生物活性治疗效果的信使。荧光成像是检测内源性 CO 的有力工具,这推动了低成本、易于使用的荧光探针的发展。在这项研究中,报道了四个带有不同取代基的偶氮苯衍生物(A1、A2、A3 和 A4),包括它们的几何结构、光物理参数以及对 Cu 和 CO 的光谱响应。讨论了取代基结构与性能之间的关系,以及 Cu 猝灭和 CO 传感机制。最佳探针(A1)没有取代基,在存在 Cu 的情况下能有效地猝灭荧光,其 PLQY 从 0.33 降低到 0.02(PLQY = 荧光量子产率)。CO 脱氧后,A1 的荧光在 180 秒内可恢复(PLQY 恢复到 0.32)。其传感机制是通过与 Cu 形成非荧光复合物(化学计量比为 1:1)实现的静态机制。报道了 A1 用于 HeLa 细胞内源性 CO 的生物成像性能。

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引用本文的文献

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J Org Chem. 2024 Dec 20;89(24):17891-17909. doi: 10.1021/acs.joc.4c02301. Epub 2024 Nov 14.