A highly selective ratiometric fluorescent probe for biothiol and imaging in live cells

Abstract

A new N-butyl-4-amino-1,8-naphthalimide-based colorimetric and ratiometric fluorescent probe for the detection of biothiols (cysteine, homocysteine, and glutathione) was designed and synthesized.

A red-emission fluorescence probe based on 1,4-addition reaction mechanism for the detection of biothiols in vitro and in vivo

“…Biothiols, including cysteine (Cys), homocysteine (Hcy) and glutathione (GSH), play important roles in maintaining redox homeostasis in biological systems through equilibrium between the reduced free sulfhydryl group (-SH) and oxidized disulfide forms. [1][2][3] This biothiol species is reported to be involved in many cellular functions, such as maintaining signal transduction and regulating gene expression, etc. 4,5 The abnormal levels of biothiols in bodies were found to be associated with many diseases and the alternation concentrations of endogenous biothiols in cellular and organs have gradually been considered as essential biomarkers of some common clinical diseases, including osteoporosis, liver damages, and even severe cancers.…”

A 3,5-dinitropyridin-2yl substituted naphthalimide-based fluorescent probe for the selective detection of biothiols and its application in cell-imaging

“…Fluorescent probes have attracted wide attention due to their high selectivity and sensitivity, real-time detection, noninvasiveness, and biocompatibility characteristics. [10][11][12][13] In the development of a uorescent probe for biothiol sensing, the design strategies are mainly focused on Michael addition, [14][15][16] nucleophilic cleavage-cyclization, [17][18][19] metal coordination complex-displacement, [20][21][22] and nucleophilic aromatic substitution (SNAr). [23][24][25][26] Giving the strong nucleophilicity of biothiols, especially their corresponding deprotonated thiolate anion, it is desirable to introduce a strong electron-withdrawing group as a biothiol recognition site to a uorophore platform.…”

A Copper (II) Ensemble-Based Fluorescence Chemosensor and Its Application in the ‘Naked–Eye’ Detection of Biothiols in Human Urine

“…Among various conventional methods such as electrochemical approaches [15,16], high-performance liquid chromatography (HPLC) [17,18], gas chromatography [19,20] and mass spectrometry (MS) [21], fluorescence analysis using a responsive molecular probe or chemosensor has been recognized as one of the most promising approaches due to its excellent sensitivity, selectivity, and capability of detecting analytes in live biological specimens [22][23][24][25][26]. To date, a large number of fluorescence chemosensors aiming to distinguish biothiols from other amino acids and bioactive species have been developed based on several sensing mechanisms: (1) Michael addition [27][28][29]; (2) cyclization with aldehyde [30,31]; (3) the cleavage of sulfonamide, sulfonate esters, selenium-nitrogen bonds and disulfide bonds [32][33][34][35][36][37][38]; (4) intramolecular elimination [39,40]. However, most organic reaction-based fluorescence chemodosimeters suffer several problems such as time-consuming synthesis and the synthesis procedure commonly requires strict reaction condition, which somehow limit the practical application in biosystems [41].…”