A dual-modality fluorescent probe for peroxynitrite based on TICT-AIE synergy: Environmental responsiveness and biological imaging

IF 4.2 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments Pub Date : 2025-09-16 DOI:10.1016/j.dyepig.2025.113249

Weiwei Yu , Peng Ji , Guangnan Xing , Lingxiao Xiong , Zhiguang Song , Guodong Feng

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Abstract

Peroxynitrite (ONOO⁻) is a highly reactive nitrogen species implicated in diverse physiological and pathological processes, yet its transient nature poses significant challenges for real-time monitoring. Herein, we report a novel environment-adaptive fluorescent probe, TBN-BPE, that exhibits dual-mode fluorescence response to ONOO⁻ based on the interplay between twisted intramolecular charge transfer (TICT) and aggregation-induced emission (AIE) mechanisms. Structurally, TBN-BPE integrates a triphenylamine donor, a benzothiazole acceptor, and a boronate ester recognition unit, enabling selective cyclization upon ONOO⁻ exposure. In DMSO-rich media, ONOO⁻ treatment induces a “turn-on” fluorescence response via TICT suppression and enhanced radiative decay. In contrast, under water-rich conditions, ONOO⁻ promotes aggregation and π–π stacking, resulting in fluorescence quenching and a hypsochromic shift. The probe exhibits high selectivity for ONOO⁻ over competing reactive species, with detection limits of 71 nM and 77 nM under water-poor and water-rich conditions, respectively. Practical utility is demonstrated through quantitative detection in spiked human saliva samples and dual-channel fluorescence imaging of exogenous and endogenous ONOO⁻ in A549 cells. This work introduces a versatile probe design strategy for responsive and context-aware imaging of reactive nitrogen species in complex biological environments.

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基于TICT-AIE协同作用的过氧亚硝酸盐双模荧光探针：环境响应性和生物成像

过氧亚硝酸盐（ONOO−）是一种高活性氮，参与多种生理和病理过程，但其瞬态性质给实时监测带来了重大挑战。在此，我们报道了一种新的环境自适应荧光探针TBN-BPE，它基于扭曲分子内电荷转移（TICT）和聚集诱导发射（AIE）机制之间的相互作用，对ONOO−表现出双模式荧光响应。在结构上，TBN-BPE集成了一个三苯胺供体，一个苯并噻唑受体和一个硼酸酯识别单元，在ONOO -暴露时实现选择性环化。在富含dmso的介质中，ONOO−处理通过抑制TICT和增强辐射衰减诱导“开启”荧光响应。相反，在富水条件下，ONOO−促进聚集和π -π堆积，导致荧光猝灭和次色移。该探针对ONOO−具有较高的选择性，在贫水和富水条件下的检测限分别为71 nM和77 nM。通过在人类唾液样本中进行定量检测，以及在A549细胞中对外源性和内源性ONOO−进行双通道荧光成像，证明了其实用性。这项工作介绍了一种多功能探针设计策略，用于在复杂的生物环境中对活性氮物种进行响应性和上下文感知成像。

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来源期刊

Dyes and Pigments 工程技术-材料科学：纺织

CiteScore

8.20

自引率

13.30%

发文量

933

审稿时长

33 days

期刊介绍： Dyes and Pigments covers the scientific and technical aspects of the chemistry and physics of dyes, pigments and their intermediates. Emphasis is placed on the properties of the colouring matters themselves rather than on their applications or the system in which they may be applied. Thus the journal accepts research and review papers on the synthesis of dyes, pigments and intermediates, their physical or chemical properties, e.g. spectroscopic, surface, solution or solid state characteristics, the physical aspects of their preparation, e.g. precipitation, nucleation and growth, crystal formation, liquid crystalline characteristics, their photochemical, ecological or biological properties and the relationship between colour and chemical constitution. However, papers are considered which deal with the more fundamental aspects of colourant application and of the interactions of colourants with substrates or media. The journal will interest a wide variety of workers in a range of disciplines whose work involves dyes, pigments and their intermediates, and provides a platform for investigators with common interests but diverse fields of activity such as cosmetics, reprographics, dye and pigment synthesis, medical research, polymers, etc.