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2-氮杂芳基-2-(氧化吲哚-2-亚基)乙腈作为锌的比色探针:合成与光学性质

2-Azahetaryl-2-(oxoindolin-2-ylidene)acetonitriles as Colorimetric Probes for Zn: Synthesis and Optical Properties.

作者信息

Shcherban Vladyslav V, Kuleshova Olena O, Keda Tetiana Ye, Khilya Olga V, Gras Emmanuel, Volovenko Yulian M

机构信息

Faculty of Chemistry, Taras Shevchenko National University of Kyiv, Lva Tolstoho Street 12, Kyiv01033, Ukraine.

Laboratoire de Chimie de Coordination, Centre National de la Recherche Scientifique, UPR 8241, Université Fed́eŕale Toulouse Midi-Pyreńeés, 205, Route de Narbonne, ToulouseF-31077, France.

出版信息

ACS Omega. 2022 Nov 16;7(47):42819-42827. doi: 10.1021/acsomega.2c04747. eCollection 2022 Nov 29.

DOI:10.1021/acsomega.2c04747
PMID:36467962
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9713784/
Abstract

A new one-pot approach for the synthesis of the Zn-sensitive probes 2-azahetaryl-2-(oxoindolin-2-ylidene)acetonitriles and is described. The method includes the formation of imidoylchloride and its further condensation with azahetarylacetonitrile . The structure of the obtained compounds is studied using H nuclear magnetic resonance (NMR), C NMR, infrared (IR), high-resolution mass spectrometry (HRMS), and UV-Vis spectroscopy techniques. Two model ligands both exhibiting the highest extinction coefficient and the best solubility in a Tris buffer pH 7.2/dimethyl sulfoxide (DMSO) solution, namely 5-methyl-benzothiazole derivative and benzoxazole derivative , are thoroughly studied as colorimetric probes for Zn. The probe has the highest sensitivity to Zn, showing a limit of ion detection (LOD) calculated by the 3S criterion of 0.43 μM and selectivity upon masking Cu ions with NaSO. The composition of the complexes in the solution was determined by the limited logarithm method. The stability constant (lg ) values of of 10.27 ± 0.02 and of 12.5 ± 0.2 indicate the formation of complexes of average stability.

摘要

描述了一种合成锌敏感探针2-氮杂芳基-2-(氧代吲哚啉-2-亚基)乙腈的新型一锅法。该方法包括亚胺酰氯的形成及其与氮杂芳基乙腈的进一步缩合。使用氢核磁共振(NMR)、碳核磁共振、红外(IR)、高分辨率质谱(HRMS)和紫外可见光谱技术研究了所得化合物的结构。对两种在pH 7.2的Tris缓冲液/二甲基亚砜(DMSO)溶液中均表现出最高消光系数和最佳溶解性的模型配体,即5-甲基苯并噻唑衍生物和苯并恶唑衍生物,作为锌的比色探针进行了深入研究。探针 对锌具有最高的灵敏度,通过3S标准计算的离子检测限(LOD)为0.43 μM,在用NaSO掩蔽铜离子时具有选择性。通过有限对数法确定了溶液中配合物的组成。 的稳定性常数(lg )值为10.27±0.02, 的稳定性常数(lg )值为12.5±0.2,表明形成了平均稳定性的配合物。

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