Ratiometric fluorescent strategy for malononitrile determination in organic and aqueous medium and biological imaging

Ratiometric fluorescent strategy for malononitrile determination in organic and aqueous medium and biological imaging
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有机和水介质中丙二腈测定及生物成像的比率荧光策略

DOI:
10.1016/j.dyepig.2020.108859
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发表时间:
2021
期刊:
影响因子:
4.5
通讯作者:
Ding Caifeng
Ding Caifeng
中科院分区:
材料科学2区
文献类型:
--
作者:
Gong Yan;Guo Xinjie;Teng Baohui;Zhang Qian;Zhang Peng;Ding Caifeng

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丙二腈是一种用途广泛、反应活性高的二腈化合物,在多合成有机医药化学和工业生产中具有广阔的应用前景。考虑到动物组织代谢过程中向HCN的转化,丙二腈具有潜在的环境污染和健康风险。首次建立了基于反应触发荧光团的比率荧光探针4-(苯并噻唑-2-基)-2-羟基苯甲醛(HBTA),用于检测有机相和水相中的丙二腈。通过HR-MS分析和核磁共振滴定光谱证实了丙二腈响应荧光信号的比值分析是由Knovenagel缩合和分子内环合贡献的。此外,该比率探针提供了一种快速响应、高灵敏度和高选择性的检测丙二腈的奇妙策略,表明该探针具有良好的成像性能,不能半定量检测丙二腈水平。
Malononitrile is a versatile dinitrile compound with high reactivity, which has wide prospect in application for multisynthetic organic medical chemistry and industrial manufacture. Considering of the transformation to HCN in animal tissue metabolism, malononitrile has potential environmental pollution and health risks. Here, a ratiometric fluorescent probe 4-(benzothiazol-2-yl)-2-hydroxy benzaldehyde (HBTA) for detection of malononitrile in organic and aqueous phase is developed on the basis of reaction-triggered fluorophore for the first time. The ratiometric assay with malononitrile-responsive fluorescence signal was contributed by Knoevenagel condensation and intramolecular cyclization, which was confirmed by HR-MS analysis and NMR titration spectra. In addition, this ratiometric probe provided a fancy strategy for detection of malononitrile with fast response, high sensitivity and selectivity, declaring excellent imaging performance invivocapable of semi-quantification for malononitrile level.
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