Isoxazole-based styryl dyes with macrocyclic receptors: synthesis, ion sensing properties and applications in bioimaging

IF 4.1 3区化学 Q2 CHEMISTRY, PHYSICAL

Journal of Photochemistry and Photobiology A-chemistry Pub Date : 2025-05-14 DOI:10.1016/j.jphotochem.2025.116497

Nadezhda E. Astakhova , Kirill S. Sadovnikov , Dmitry A. Vasilenko , Alina A. Markova , Minh Tuan Nguyen , Ivan D. Burtsev , Alexei A. Yakushev , Yuri K. Grishin , Yulia A. Gracheva , Yulia L. Volodina , Alina R. Lukmanova , Vasily V. Spiridonov , Alexander A. Yaroslavov , Alexei D. Averin , Vladimir A. Kuzmin , Elena R. Milaeva , Elena B. Averina

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Abstract

Two series of novel 4-nitro-5-styrylisoxazoles (11 compounds) containing various macrocyclic substituents at positions 3 and 5 of the isoxazole cycle were obtained. Isoxazoles with macrocyclic signal unit in the styryl moiety demonstrated sensor properties in organic solvents to a number of metal cations (Mg(II), Ca(II), Zn(II), La(III), Al(III), Pb(II)). Aggregation-induced emission for the obtained dyes was found in the mixture of DMSO/H₂O. In the presence of serum albumin, aggregates of macrocyclic styrylisoxazoles in an aqueous medium dissociated into monomers and formed complex with macromolecule. The compounds demonstrated cytoplasmic distribution in cells in two different forms as aggregates with ‘red’ fluorescence and dyes complexes with cellular proteins with ‘green’ fluorescence, which is promising for studying metabolic processes in the cell.

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具有大环受体的异恶唑基苯乙烯染料：合成、离子传感特性及其在生物成像中的应用

得到了两个新的4-硝基-5-苯乙烯基异恶唑系列（11个化合物），它们在异恶唑环的3位和5位上含有不同的大环取代基。苯乙烯基部分具有大环信号单元的异恶唑在有机溶剂中对多种金属阳离子（Mg（II）、Ca（II）、Zn（II）、La（III）、Al（III）、Pb(II)）表现出传感器性质。所得染料在DMSO/H2O混合物中有聚集致发光现象。在血清白蛋白存在的情况下，大环苯基异恶唑的聚集体在水介质中解离成单体并与大分子形成复合物。这些化合物在细胞质中以两种不同的形式分布，即具有“红色”荧光的聚集体和具有“绿色”荧光的细胞蛋白染料复合物，这为研究细胞中的代谢过程提供了希望。

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来源期刊

Journal of Photochemistry and Photobiology A-chemistry 化学-物理化学

CiteScore

7.90

自引率

7.00%

发文量

580

审稿时长

48 days

期刊介绍： JPPA publishes the results of fundamental studies on all aspects of chemical phenomena induced by interactions between light and molecules/matter of all kinds. All systems capable of being described at the molecular or integrated multimolecular level are appropriate for the journal. This includes all molecular chemical species as well as biomolecular, supramolecular, polymer and other macromolecular systems, as well as solid state photochemistry. In addition, the journal publishes studies of semiconductor and other photoactive organic and inorganic materials, photocatalysis (organic, inorganic, supramolecular and superconductor). The scope includes condensed and gas phase photochemistry, as well as synchrotron radiation chemistry. A broad range of processes and techniques in photochemistry are covered such as light induced energy, electron and proton transfer; nonlinear photochemical behavior; mechanistic investigation of photochemical reactions and identification of the products of photochemical reactions; quantum yield determinations and measurements of rate constants for primary and secondary photochemical processes; steady-state and time-resolved emission, ultrafast spectroscopic methods, single molecule spectroscopy, time resolved X-ray diffraction, luminescence microscopy, and scattering spectroscopy applied to photochemistry. Papers in emerging and applied areas such as luminescent sensors, electroluminescence, solar energy conversion, atmospheric photochemistry, environmental remediation, and related photocatalytic chemistry are also welcome.