Amphiphilic pyrene-functionalized triazoliums for ATP recognition

IF 4 2区化学 Q2 CHEMISTRY, PHYSICAL

Journal of Molecular Structure Pub Date : 2024-11-04 DOI:10.1016/j.molstruc.2024.140598

Hong-Wei Huang , Yue-Bo He , Zhao-Hui Xin , Qian-Yong Cao

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引用次数: 0

Abstract

Four pyrene functionalized triazolium salts with different lengths of alkyl tail from C4 to C16, i.e., PYTAZ-C4, PYTAZ-C8, PYTAZ-C12 and PYTAZ-C16, have been designed and synthesized for ATP recognition. It was revealed that the longer alkyl tail anchored receptors PYTAZ-C12 and PYTAZ-C16 exhibit low CMC values, and self-assemble nanoaggregation at low concentration in aqueous solution, which show a pyrene-based excimer emission at 496 nm. However, the shorter alkyl anchored receptors PYTAZ-C4 and PYTAZ-C8 give only the pyrene-based monomer emission at 380 nm at the test concentration of 10 μM in aqueous solution. Importantly, PYTAZ-C12 and PYTAZ-C16 exhibit a good fluorescence turn-on response toward polyphosphate anions, especially ATP, with the detection limits of 2.5 μM and 0.77 μM, respectively. Furthermore, probe PYTAZ-C16 was successfully used for fluorescence imaging of intracellular ATP in living cells.

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用于识别 ATP 的两亲性芘功能化三唑鎓

设计并合成了四种芘官能化的三唑鎓盐，其烷基尾长度从 C4 到 C16 不等，即 PYTAZ-C4、PYTAZ-C8、PYTAZ-C12 和 PYTAZ-C16，用于识别 ATP。研究发现，PYTAZ-C12 和PYTAZ-C16 具有较长的烷基尾锚定受体，其 CMC 值较低，在水溶液中浓度较低时就会自组装成纳米聚集体，并在 496 纳米波长处显示出基于芘的准分子发射。然而，PYTAZ-C4 和PYTAZ-C8 这两种较短的烷基锚定受体在水溶液中的测试浓度为 10 μM 时，只能在 380 纳米波长处发出芘基单体辐射。重要的是，PYTAZ-C12 和 PYTAZ-C16 对多磷酸盐阴离子（尤其是 ATP）具有良好的荧光开启响应，检测限分别为 2.5 μM 和 0.77 μM。此外，探针PYTAZ-C16 还成功地用于活细胞内 ATP 的荧光成像。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Journal of Molecular Structure 化学-物理化学

CiteScore

7.10

自引率

15.80%

发文量

2384

审稿时长

45 days

期刊介绍： The Journal of Molecular Structure is dedicated to the publication of full-length articles and review papers, providing important new structural information on all types of chemical species including: • Stable and unstable molecules in all types of environments (vapour, molecular beam, liquid, solution, liquid crystal, solid state, matrix-isolated, surface-absorbed etc.) • Chemical intermediates • Molecules in excited states • Biological molecules • Polymers. The methods used may include any combination of spectroscopic and non-spectroscopic techniques, for example: • Infrared spectroscopy (mid, far, near) • Raman spectroscopy and non-linear Raman methods (CARS, etc.) • Electronic absorption spectroscopy • Optical rotatory dispersion and circular dichroism • Fluorescence and phosphorescence techniques • Electron spectroscopies (PES, XPS), EXAFS, etc. • Microwave spectroscopy • Electron diffraction • NMR and ESR spectroscopies • Mössbauer spectroscopy • X-ray crystallography • Charge Density Analyses • Computational Studies (supplementing experimental methods) We encourage publications combining theoretical and experimental approaches. The structural insights gained by the studies should be correlated with the properties, activity and/ or reactivity of the molecule under investigation and the relevance of this molecule and its implications should be discussed.