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  • Title: A turn-on fluorescence probe for cysteine/homocysteine based on the nucleophilic-induced rearrangement of benzothiazole thioether.
    Author: Li M, Kang N, Zhang C, Liang W, Zhang G, Jia J, Yao Q, Shuang S, Dong C.
    Journal: Spectrochim Acta A Mol Biomol Spectrosc; 2019 Nov 05; 222():117262. PubMed ID: 31212195.
    Abstract:
    A fluorescent probe, 4-(benzothiazole-2-ylthio)-7-nitro-2,1,3-benzoxadiazole (TBT-NBD) was developed for cysteine (Cys) and homocysteine (Hcy). The reaction mechanism was based on the Cys/Hcy-induced nucleophilic substitution of benzothiazole thioether then Smiles rearrangement reaction to form corresponding amino-nitrobenzoxadiazole, which emitted yellow-green fluorescence and guaranteed the high selectivity for Cys/Hcy over glutathione (GSH). TBT-NBD could detect Cys/Hcy within 5 min in the presence of high concentration of GSH and other amino acids. Moreover, TBT-NBD had been exploited to identify intracellular Cys/Hcy in living cells in light of its low toxicity.
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