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Merocyanine-based turn-on fluorescent probe for the sensitive and selective determination of thiophenols via a pKa shift mechanism.
Talanta ( IF 5.6 ) Pub Date : 2020-04-03 , DOI: 10.1016/j.talanta.2020.120965
Shengrui Zhang 1 , Qin Wang 1 , Fangfang Wu 2 , Jiajun Yang 3 , Tianyi Cheng 2 , Xiao-Feng Yang 2 , Zheng Li 3 , Hua Li 4
Affiliation  

The development of fluorescent probes for the sensitive and selective determination of highly toxic thiophenols is considerably important in the fields of biological and environmental sciences. Herein, a turn-on fluorescent probe for thiophenol, named MCSH, was constructed based on a pKa shift mechanism, employing merocyanine dye as the fluorophore and 2,-4-dinitrobenzenesulfonamide (DNBS) group as the recognition unit. The imine nitrogen of MCSH has a pKa value of 4.12, which renders its non-fluorescent Schiff base form exclusively under neutral conditions. However, after reacting with thiophenols, its DNBS group was removed to afford a merocyanine dye as the final product, whose pKa value upshifts to 8.11, and was present mainly as the fluorescent protonated Schiff base form under neutral media. Such drastic change in pKa values leads to a significant fluorescence enhancement and can be utilized for the detection of thiophenols. The fluorescence intensity at 627 nm increases linearly with thiophenol concentration in the range of 0.2–3 μM with a detection limit of 15 nM (S/N = 3). MCSH displays high selectivity for the detection of thiophenols over a wide range of other analytes, including aliphatic thiols. Furthermore, the preliminary applications of MCSH for monitoring thiophenols in living cells and environmental have been carried out.



中文翻译:

基于花青的开启式荧光探针,用于通过pKa移位机制灵敏和选择性地测定苯硫酚。

在生物和环境科学领域,开发用于灵敏和选择性测定高毒性硫酚的荧光探针非常重要。在此,导通为苯硫酚荧光探针,命名MCSH,基于AP构建ķ一个换档机构,采用部花青染料作为荧光团和2,-4-dinitrobenzenesulfonamide(DNBS)基团作为所述识别单元。的亚胺氮MCSH具有p ķ一个的4.12值,这仅仅使中性条件下其非荧光希夫碱形式。但是,与硫酚反应后,其DNBS基团被除去,得到了花青染料作为最终产物,其p K一个值升挡至8.11,并且是目前主要作为荧光在中性介质质子化的席夫碱形式。p K a值的这种急剧变化导致荧光显着增强,可用于检测硫酚。627 nm处的荧光强度随苯硫酚浓度在0.2–3μM范围内线性增加,检出限为15 nM(S / N = 3)。MCSH对多种其他分析物(包括脂肪族硫醇)中的硫酚检测具有高选择性。此外,已经进行了MCSH在活细胞和环境中监测苯酚的初步应用。

更新日期:2020-04-03
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