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一种基于二芳基乙烯且具有由HSO激活的荧光至光致变色特性的探针:其在活细胞和斑马鱼中的成像应用。

A diarylethene-based probe with HSO-activated fluorescence to photochromism: Its imaging application in living cells and zebrafish.

作者信息

Wu Yinjie, Gong Zhihong, Wu Xiaoqian, Huang Yiyan, Sun Leilei, Ding Haichang, Zeng Yu-Ling, Fan Congbin, Liu Gang, Pu Shouzhi

机构信息

Jiangxi Provincial Key Laboratory of Organic Functional Molecules, Institute of Organic Chemistry, Jiangxi Science and Technology Normal University, Nanchang 330013, PR China.

Jiangxi Provincial Key Laboratory of Organic Functional Molecules, Institute of Organic Chemistry, Jiangxi Science and Technology Normal University, Nanchang 330013, PR China.

出版信息

Anal Chim Acta. 2025 Jul 15;1359:344114. doi: 10.1016/j.aca.2025.344114. Epub 2025 Apr 25.

DOI:10.1016/j.aca.2025.344114
PMID:40382103
Abstract

Sulfur dioxide (SO) and its derivatives (sulfite SO and bisulfite HSO) have important applications in industrial production and food preservation, but excessive intake can be hazardous to human health. Therefore, the development of highly sensitive and selective HSO detection methods is essential to safeguard food safety and public health. Conventional HSO probes mainly rely on colorimetric or fluorescence detection, but these methods have obvious limitations in that the fluorescence signal disappears as soon as the UV irradiation is stopped, and they cannot provide long-lasting and readable detection results. Herein, a fluorescent probe (DP-1) constructed from diarylethene, fluorophores and ion recognition sites were designed and developed. DP-1 emits yellow fluorescence emission maximum at 600 nm in initial state, which is significantly quenched upon specific recognition of HSO. This recognition process demonstrates DP-1's good ion selectivity, interference resistance, and low detection limit of 16 nM. Notably, unlike conventional probes, DP-1 exhibits superior fluorescence properties before recognizing HSO, with no detectable photochromism. After ion recognition, its photochromic function is activated, while fluorescence completely disappears, demonstrating a switch from fluorescence to photochromism triggered by HSO. The mechanism of this recognition process was confirmed by nuclear magnetic titration, high-resolution mass spectrometry, and theoretical calculations. Additionally, DP-1 has been successfully applied for HSO detection in both live cellular and zebrafish imaging, with its excellent biocompatibility providing a reliable tool for in vivo imaging.

摘要

二氧化硫(SO₂)及其衍生物(亚硫酸盐SO₃²⁻和亚硫酸氢盐HSO₃⁻)在工业生产和食品保鲜中具有重要应用,但过量摄入会对人体健康造成危害。因此,开发高灵敏度和选择性的HSO₃⁻检测方法对于保障食品安全和公众健康至关重要。传统的HSO₃⁻探针主要依赖比色或荧光检测,但这些方法存在明显局限性,即紫外线照射停止后荧光信号立即消失,且无法提供持久且可读的检测结果。在此,设计并开发了一种由二芳基乙烯、荧光团和离子识别位点构建的荧光探针(DP-1)。DP-1在初始状态下于600 nm处发射最大黄色荧光,在特异性识别HSO₃⁻后显著猝灭。这一识别过程表明DP-1具有良好的离子选择性、抗干扰性以及16 nM的低检测限。值得注意的是,与传统探针不同,DP-1在识别HSO₃⁻之前表现出优异的荧光特性,无明显的光致变色现象。离子识别后,其光致变色功能被激活,而荧光完全消失,表明由HSO₃⁻触发了从荧光到光致变色的转变。通过核磁共振滴定、高分辨率质谱和理论计算证实了这一识别过程的机制。此外,DP-1已成功应用于活细胞和斑马鱼成像中的HSO₃⁻检测,其优异的生物相容性为体内成像提供了可靠工具。

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