A Rhodamine-Based Fluorescent Probe Containing a Se−N Bond for Detecting Thiols and Its Application in Living Cells

Abstract

Here we report a new rhodamine-based fluorescent probe containing a selenium−nitrogen bond for detecting thiols based on the nucleophilic substitution of sulfhydryl. The probe was successfully applied to the imaging of thiols in both HL-7702 cells and HepG2 cells with high sensitivity and selectivity.

Determination of glutathione and glutathione disulfide in biological samples: An in-depth review

“…Other fluorophores include cell-permeable latent ("turn-on") probes. Aniline-based compounds have been designed with a sulfonamide linkage [88], and rhodamine-based ones with either a Se-N bond [89], two disulfide bonds [90] or a sulfonamide linkage [91]. Cleavage of the respective functionally important bonds by thiols in vivo or in cyto results in the liberation of the fluorescent aniline [88], rhodamine-6G [89] or rhodamine-110 [90,91], with a subsequent increase in the fluorescence.…”

Styryl-BODIPY based red-emitting fluorescent OFF–ON molecular probe for specific detection of cysteine

“…Selective detection of biological thiols, such as cysteine, homocysteine and glutathione, have attracted much attention due to the pivotal role of these -SH containing molecules in physiological pathways (Chen et al, 2010a;Weh et al, 2007;Tang et al, 2007;Refsum et al, 2004;Hong et al, 2009;Lee et al, 2010;Huo et al, 2010;Shang and Dong, 2009;Yu et al, 2007;Huang et al, 2010;Yi et al, 2009;Wang et al, 2009). For example, increased white cell cysteine concentrations are only observed in individuals with cystinosis.…”

“…Alternatively dyads of fluorophore/maleimides were used as thiol probes (Matsumoto et al, 2007;Weh et al, 2007;Maeda et al, 2006). Fluorophores containing formyl (-CHO) group were also used as thiol probes, which are based on tuning the intramolecular charge transfer (ICT) effect by addition with thiols (Tang et al, 2007;Tanaka et al, 2004;Zhang et al, 2006;Lee et al, 2008;Chen et al, 2010b).…”

Use of Selenium to Detect Mercury in Water and Cells: An Enhancement of the Sensitivity and Specificity of a Seleno Fluorescent Probe

“…[15] In a previous study, this inspired us to design a fluorescent probe that contained a Se À N bond for detecting thiols in living cells. [16] In addition, the antitoxic action of selenium toward toxic heavy-metal ions should also be paid much attention. As early as 1967, Pǎ ízek and Oštµdalovµ described how selenite shows a protecting property against the toxicity of inorganic mercury.…”