Quinolinium-Based Fluorescent Probes for the Detection of Thiophenols in Environmental Samples and Living Cells
Quinolinium-Based Fluorescent Probes for the Detection of Thiophenols in Environmental Samples and Living Cells
复制标题
用于检测环境样品和活细胞中苯硫酚的喹啉基荧光探针
DOI：
10.1002/asia.201200594
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发表时间：
2012-11-01
影响因子：
4.1
通讯作者：
Song, Qin-Hua
中科院分区：
文献类型：
--
作者：
Liu, Xiu-Ling;Duan, Xue-You;Song, Qin-Hua
以2，4-二硝基苯氧基（DNP）为亲核识别单元，以6-或7-羟基喹啉为荧光基团，合成了一种新型的硫酚类荧光探针6 HQM-DNP和7 HQM-DNP。作为醚，这些非荧光探针分子可以通过硫醇阴离子从硫酚中的芳族亲核取代（SNAr）释放相应的荧光喹啉（6 HQM和7 HQM）。传感反应是高度敏感的（检测限为8 nM的7 HQM-DNP）和高选择性的硫酚脂肪族硫醇和其他亲核试剂在中性条件下（pH 7.3）。的探针迅速响应硫酚，与二阶速率常数k=45？M-1？s-1的7 HQM-DNP和24？M-1？对于6 HQM-DNP为s-1。此外，通过共聚焦荧光成像证实了7 HQM-DNP对活细胞中硫酚的选择性检测。此外，这些喹啉鎓盐显示出优异的化学和热稳定性。总之，这种类型的探针可能会发现用于检测环境样品和生物系统中的硫酚。
A new type of fluorescent probes for thiophenols, 6HQM-DNP and 7HQM-DNP, containing 6- or 7-hydroxy quinonlinium as fluorophore and 2,4-dinitrophenoxy (DNP) as nucleophilic recognition unit were constructed. As ethers, these non-fluorescent probe molecules can release the corresponding fluorescent quinolinium (6HQM and 7HQM) through aromatic nucleophilic substitution (SNAr) by thiolate anions from thiophenols. The sensing reaction is highly sensitive (detection limit of 8 nM for 7HQM-DNP) and highly selective to thiophenols over aliphatic thiols and other nucleophiles under neutral conditions (pH 7.3). The probes respond rapidly to thiophenols, with second-order rate constants k=45?M-1?s-1 for 7HQM-DNP and 24?M-1?s-1 for 6HQM-DNP. Furthermore, the selective detection of thiophenols in living cells by 7HQM-DNP was demonstrated by confocal fluorescence imaging. In addition, these quinolinium salts show excellent chemical and thermal stability. In conclusion, this type of probes may find use in the detection of thiophenols in environmental samples and biosystems.