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Issue 30, 2018
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Regulating glutathione-responsiveness of naphthalimide-based fluorescent probes by an oxidation strategy

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Abstract

Two naphthalimide-based fluorescent probes containing a thiomorpholine (Np-NS) or a sulfoxide-morpholine (Np-NSO) component are reported. The morpholine unit of non-fluorescent Np-NS and Np-NSO can transform into sulphone-morpholine and be accompanied by blue fluorescence upon oxidative stress, ascribed to the formation of sulphone-morpholine on probes. This sensing behavior displays that they can selectively respond to glutathione to generate a green emission by a sulfonamide-based detection moiety both in vitro and in living cells. Interestingly, the different oxidation states of a sulphur atom on a thiomorpholine ring can be utilized to regulate responsiveness of these probes towards glutathione. Such an oxidation strategy would provide a possibility for enhancing the response rate.

Graphical abstract: Regulating glutathione-responsiveness of naphthalimide-based fluorescent probes by an oxidation strategy

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Publication details

The article was received on 29 May 2018, accepted on 12 Jul 2018 and first published on 13 Jul 2018


Article type: Paper
DOI: 10.1039/C8OB01258J
Citation: Org. Biomol. Chem., 2018,16, 5517-5523
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    Regulating glutathione-responsiveness of naphthalimide-based fluorescent probes by an oxidation strategy

    G. Liu, W. Chen, Z. Xu, F. Ye, Y. Pan, X. Chen, S. H. Liu, L. Zeng and J. Yin, Org. Biomol. Chem., 2018, 16, 5517
    DOI: 10.1039/C8OB01258J

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