Abstract
A naphthalimide-based fluorescent probe was developed for the sensitive and selective detection of biothiols. The fluorescence of the probe was quenched by the electron-withdrawing 3,5-dinitropyridin-2-yl group via the photoinduced electron transfer process, and turned on by biothiol-triggered nucleophilic aromatic substitution. The sensing mechanism was confirmed by HPLC analysis and theoretical calculations. The probe shows a satisfactory response time of 30 min with low detection limits (Cys: 0.32 μM; Hcy: 0.88 μM; GSH: 0.46 μM). Furthermore, the probe was successfully utilized to detect endogenous and exogenous biothiols in HeLa cells.
Highlights
Biological thiols, including cysteine (Cys), homocysteine (Hcy), and glutathione (GSH), are found to be closely associated with many diseases.[1,2] For example, an abnormal level of Cys is relevant to skin lesions, liver damage, brain injury, and Parkinson's disease.[3]
The sensing mechanism was confirmed by HPLC analysis and theoretical calculations
Characterizations are given in the experimental section and the Electronic supplementary information (ESI) (Fig. S1–S3†)
Summary
Biological thiols (biothiols), including cysteine (Cys), homocysteine (Hcy), and glutathione (GSH), are found to be closely associated with many diseases.[1,2] For example, an abnormal level of Cys is relevant to skin lesions, liver damage, brain injury, and Parkinson's disease.[3]. We report a new uorescent probe for the detection of biothiols based on the nucleophilic aromatic substitution. N-Butyl-4-hydroxy-1,8-naphthalimide (NAP-OH) was selected as the uorophore due to its high photostability, and good biocompatibility.[27,28] NAP-DNP exhibits high selectivity and sensitivity for biothiols with low detection limits (0.32 mM, 0.88 mM and 0.46 mM for Cys, Hcy and GSH, respectively) and medium response (30 min). The low cell cytotoxicity indicates that NAP-DNP is suitable for the sensing of biothiols in living cells
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