一种基于异佛尔酮的生物硫醇荧光探针

doi:10.3969/j.issn.1000-1565.2025.02.006

摘要/Abstract

摘要： 小分子生物硫醇在生物体内扮演着至关重要的角色,当其浓度异常时会引发各种疾病.因此,开发用于检测生物体内硫醇水平变化的新方法对于人类生命健康具有重要意义.由于荧光探针法具有操作简单、选择性高、灵敏度高、响应快速等特点,本文以2,4-二硝基苯磺酰基作为识别基团,异佛尔酮衍生物为荧光团,设计合成了一种近红外硫醇荧光探针DCI-AC-NBS.该探针与硫醇发生“亲核取代-环化”反应后生成荧光性能优良的香豆素类物质DCI-COU.该探针对硫醇具有选择性高、检出限低和斯托克斯位移大等优点,并可用于实时监测细胞内硫醇水平的变化,为生物体内硫醇检测提供新思路.

关键词: 荧光探针, 生物硫醇, 生物成像

Abstract: Small molecule biothiols play vital roles in living organisms, and abnormal concentrations can lead to various diseases. Therefore, developing new methods to detect biothiol levels is very important for human health. Fluorescent probes, known for their simple operation, high selectivity, high sensitivity, and fast response, are particularly useful for this purpose. In this study, a near-infrared fluorescent probe, DCI-AC-NBS, was designed and synthesized for biothiols detection, incorporating a 2,4-dinitrobenzenesulfonyl group as the recognition moiety and an isophorone derivative as the fluorophore. Through a nucleophilic substitution-cyclization reaction between DCI-AC-NBS and biothiols, a coumarin derivative, DCI-COU, was produced, exhibiting excellent fluorescence properties. The DCI-AC-NBS has the advantages of high selectivity, a low detection limit, and a large Stokes shift for biothiols, making it suitable for real-time monitoring of intracellular biothiol level changes, thereby providing a new approach for in vivo biothiol detection.

Key words: fluorescent probe, biothiols, bioimaging

中图分类号:

O316

江宁宁,周柯岩,刘红梅,李晓幸,杨瑜涛. 一种基于异佛尔酮的生物硫醇荧光探针[J]. 河北大学学报(自然科学版), 2025, 45(2): 157-164.

JIANG Ningning, ZHOU Keyan, LIU Hongmei, LI Xiaoxing, YANG Yutao. A fluorescent probe for biothiols based on isophorone[J]. Journal of Hebei University(Natural Science Edition), 2025, 45(2): 157-164.

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