A near-infrared fluorescent sensor with large Stokes shift for rapid and highly selective detection of thiophenols in water samples and living cells

Abstract

The development of simple methods with high sensitivity and selectivity to differentiate toxic aromatic thiols (thiophenols) from aliphatic thiols (cysteine, homocysteine, and glutathione) and hydrogen sulfide (HS) is of great significance. Herein, we report on the fabrication of a novel near-infrared (NIR) fluorescent sensor for rapid and highly selective detection of thiophenols through the photoinduced electron transfer (PET) mechanism. In the presence of the thiophenols, an obvious enhancement of NIR fluorescence at 658 nm could be visualized with the aid of nucleophilic aromatic substitution (SAr) reaction. The sensor displays large Stokes shift (~ 227 nm), fast response time (< 30 s), high sensitivity (~ 8.3 nM), and good biocompatibility. Moreover, the as-prepared sensor possesses an excellent anti-interference feature even when other possible interferents exist (aliphatic thiols and HS) and has been successfully utilized for thiophenol detection in both water samples and living cells. Graphical abstract Illustration of the sensor for thiophenol imaging in living cells.

A fluorescent probe for the dual detection of mercury ions and thiols based on a simple coumarin derivative

“…8,9 Therefore, a vast number of fluorescent probes for the detection of thiophenols have been developed. [10][11][12][13][14][15][16] On the other hand, pollution by mercury ions (Hg(ii)) triggers severe environmental and human health problems. Therefore, rapid and sensitive detection of Hg(ii) is of major significance.…”

“…However, thiophenols are a highly toxic and pollutant species . Therefore, a vast number of fluorescent probes for the detection of thiophenols have been developed . On the other hand, pollution by mercury ions (Hg( ii )) triggers severe environmental and human health problems.…”

Fluorescence-Guided Cancer Diagnosis and Surgery by a Zero Cross-Talk Ratiometric Near-Infrared γ-Glutamyltranspeptidase Fluorescent Probe

“…However, colorimetric assays and HPLC techniques are not suitable for real-time biological imaging applications. In contrast, fluorescent probe-based imaging techniques with remarkable characteristics including high sensitivity, noninvasiveness, and facile visualization can offer an accurate and specific detection of GGT activity in clinic blood samples and pathological tissues, which will help in being used for early cancer diagnosis; − and the fluorescence imaging-guided GGT-activable probe is helpful for surgeons by visualizing accurate borders between cancer and normal tissue during surgery.…”

Recent Progress in the Development of Fluorescent Probes for Thiophenol

“…Furthermore, probe 13 was demonstrated to be capable of imaging PhSH in living Hela cells (Figure 6b–e). Subsequently, three other NIR fluorescent PhSH probes ( 14 [77], 15 [78,79], and 16 [79]) emerged by adopting different fluorophores, including porphyrin, dicyanoisophorone, and Nile blue (Figure 7). By incorporating 2,4-dinitrobenzenesulfonic amide into other fluorophores, a number of fluorescent PhSH probes ( 17 [80], 18 [80], 19 [81], 20 [82], and 21 [83]) were also constructed (Figure 8).…”