BODIPY-Based Ratiometric Fluorescent Sensor for Highly Selective Detection of Glutathione over Cysteine and Homocysteine

Abstract

We report a ratiometric fluorescent sensor based on monochlorinated BODIPY for highly selective detection of glutathione (GSH) over cysteine (Cys)/homocysteine (Hcy). The chlorine of the monochlorinated BODIPY can be rapidly replaced by thiolates of biothiols through thiol-halogen nucleophilic substitution. The amino groups of Cys/Hcy but not GSH further replace the thiolate to form amino-substituted BODIPY. The significantly different photophysical properties of sulfur- and amino-substituted BODIPY enable the discrimination of GSH over Cys and Hcy. The sensor was applied for detection of GSH in living cells.

Thiocyanation of BODIPY dyes and their conversion to thioalkylated derivatives

“…5 To the best of our knowledge, thiocyanatosubstituted boron dipyrrins have not been previously reported, although they can be considered starting materials for BODIPY sulfides. [6][7][8][9][10] For this study, ten BODIPYs (Table 1) were synthesized using established procedures [11][12][13][14][15][16][17][18] and were used as starting materials for further reactions. …”

FITC functionalized magnetic core–shell Fe3O4/Ag hybrid nanoparticle for selective determination of molecular biothiols

“…In recent years, a great amount of interesting studies have focused on the determination and sensing of biothiols. Various analytical methods including high-performance liquid chromatography [10,11], capillary electrophoresis [12,13], mass spectrometry [14], chemiluminescence [15,16], electrochemistry assay [17,18], fluorimetry [19][20][21], and nanoparticles-based colorimetric sensing strategy [22][23][24][25][26][27] for biothiols have been developed. Among these methods, fluorescent probes and gold-nanoparticle-based colorimetric sensing gradually stand out in the rapid, sensitive, and selective determination of biothiols.…”

“…Our team has developed a series of fluorescent probes that can be used for rapid detection of thiols under physiological conditions, with emission in the near infrared (NIR) region [28,29]. Yet, in most of the reported fluorescent methods, organic solvents are required to be introduced into the system to increase the solubility of fluorescent dyes [19][20][21]. As a type of recently developed biothiol sensor, gold-nanoparticlebased colorimetric sensing in general involves the aggregation, coupling, or assembly of gold nanospheres [22,23] and nanorods [24,25].…”

BODIPY-based fluorometric sensor array for the highly sensitive identification of heavy-metal ions

“…The variety of synthetic pathways to BODIPYbased fluorophores allows efficient preparation. The fluorescence properties of BODIPY are tunable by simple substitution at various positions of the difluoroboron dipyrromethene core [25][26][27][28][29][30][31]. Multi-pyridyl ligands, including DPA and its derivatives N,N-di(pyridin-2-ylmethyl)-ethane-1,2-diamine (DPEA) and N,N,N -tri(pyridin-2-ylmethyl)-ethane-1,2-diamine (TPEA), are well-known receptors for heavy-metal ions, such as Zn 2+ , Cd 2+ , Hg 2+ , Cu 2+ etc [32][33][34][35][36][37][38][39][40].…”