Pyrimidine-based single-molecule fluorescent probe for sensing of pH, trivalent ions (Cr3+/Al3+/Fe3+), homocysteine, and hydroxyl radicals

IF 4.2 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments Pub Date : 2025-06-18 DOI:10.1016/j.dyepig.2025.112964

Hongbing Lu , Rui Tian , Lili Chen , Huanhuan Fan , Renjie Wang , Shouzhi Pu

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引用次数: 0

Abstract

Two novel arylvinylpyrimidine scaffold fluorescent probes, BTPAT-PA (4,4'-(5,5'-(2-aminopyrimidine-4,6-diyl)bis(ethene-2,1-diyl))bis(thiophene-5,2-diyl))bis(N, N-diphenylaniline) and BAT-PA (4,6-bis(2-(5-(anthracene-9-yl)thiophene-2-yl)vinyl)pyrimidine-2-amine), were rationally designed and synthesized using triphenylamine/anthracene as electron donors, and 2-aminopyrimidine acted as the electron acceptor. Both probes exhibit remarkable acid-responsive chromic switching with fully reversible behavior. Their initially colored solutions and intense fluorescence undergo quenching upon exposure to acidic conditions, which can be restored by subsequent base treatment, demonstrating robust stimulus-responsive cyclability. Additionally, BTPAT-PA achieves dual-mode discrimination of homocysteine (Hcy) and hydroxyl radical (•OH) via distinct covalent binding pathways, inducing naked-eye-detectable color transitions between orange and purple. In contrast, BAT-PA selectively responds to •OH through a fluorescence “turn-off” mechanism (bright green fluorescence to quenched), while remaining inert toward Hcy. Moreover, both probes enable Cr³⁺ quantification through a 1:1 binding stoichiometry, resulting in emission attenuation and yellow-to-orange color shifts with ultrahigh sensitivity (LOD: 1.31 × 10⁻⁷ mol L⁻¹ for BTPAT-PA and 3.67 × 10⁻⁷ mol L⁻¹ for BAT-PA). Finally, the multi-stimulus responsiveness of these probes was utilized to develop portable test strips for on-site visual detection of acid, Hcy, •OH, and Cr³⁺. Fluorescence imaging experiments confirmed their excellent cell-membrane permeability and low cytotoxicity, which facilitated effective cell imaging. Therefore, the multi-stimulus responsiveness and facile preparation of these probes make them promising for developing multi-signal fluorescent systems to rapidly detect acids, metal ions, and bioactive small molecules.

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基于嘧啶的单分子荧光探针，用于检测pH、三价离子（Cr3+/Al3+/Fe3+）、同型半胱氨酸和羟基自由基

以三苯胺/蒽为电子给体，2-氨基嘧啶为电子受体，合理设计合成了两种新型芳基乙烯基嘧啶支架荧光探针BTPAT-PA(4,4′-(5,5′-（2-氨基嘧啶-4,6-二基）双（乙烯-2,1-二基）双（噻吩-5,2-二基）双（N， N-二苯基）和BAT-PA（4,6-双（2-（5-（蒽-9-基）噻吩-2-基）乙烯基）嘧啶-2-胺）。这两种探针都表现出明显的酸响应色开关，具有完全可逆的行为。它们最初的有色溶液和强烈的荧光在暴露于酸性条件下会猝灭，这可以通过随后的碱处理恢复，显示出强大的刺激响应循环性。此外，BTPAT-PA通过不同的共价结合途径实现同型半胱氨酸（Hcy）和羟基自由基（•OH）的双模式识别，诱导肉眼可检测的橙色和紫色之间的颜色转换。相反，BAT-PA通过荧光“关闭”机制（亮绿色荧光熄灭）选择性地响应•OH，同时对Hcy保持惰性。此外，两种探针都可以通过1:1的结合化学计量来定量Cr3+，从而产生发射衰减和黄到橙色的偏移，具有超高灵敏度（LOD: BTPAT-PA为1.31 × 10−7 mol L−1，BAT-PA为3.67 × 10−7 mol L−1）。最后，利用这些探针的多刺激响应性开发便携式试纸条，用于现场视觉检测酸、Hcy、•OH和Cr3+。荧光成像实验证实了其优良的细胞膜通透性和低细胞毒性，有利于有效的细胞成像。因此，这些探针的多刺激响应性和易于制备使它们有望开发多信号荧光系统，以快速检测酸、金属离子和生物活性小分子。

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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.