Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 11, Issue 47, Pages 8214-8220Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c3ob41741g
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Funding
- National Natural Science Foundation of China [21202063, 50925207, 51172100, 21103073]
- Ministry of Science and Technology of China for the International Science Linkages Program [2009DFA50620, 2011DFG52970]
- Ministry of Education of China for Changjiang Innovation Research Team [IRT1064]
- Natural Science Foundation of Jiangsu Province [BK2012281]
- Jiangsu Innovation Research Team
- China Postdoctoral Science Foundation [2012M511200]
- Research Foundation of Jiangsu University [11JDG078]
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In this work, compound 1 has been rationally designed and synthesized as a new fluorescent probe for biological thiols. Notably, probe 1 has almost no background fluorescence (Phi(f) < 0.0001) in aqueous solutions; however, it exhibited fluorescence turn-on response to thiols with high sensitivity (a 246-fold fluorescence enhancement and a low detection limit of 0.22 mu M for Cys). Moreover, probe 1 showed excellent thiol specificity over other biologically relevant species. The kinetic studies indicated that the probe responded to thiols rapidly, and the pseudo-first-order rate constants of probe 1 reaction with Cys, Hcy, and GSH were determined to be 1.85842, 0.67656, and 0.51519 min(-1), respectively. A possible detection mechanism was proposed to involve the Michael addition of the thiol to the alpha,beta-unsaturated ketone, followed by a cleavage of the hemiketal group, thereby leading to the formation of a fluorescent 7-hydroxyl coumarin derivative. Furthermore, the optical responses of probe 1 to thiols were studied by TD-DFT calculations. Finally, probe 1 has been successfully applied to the detection of biological thiols in human blood serum. And the intracellular imaging applications established that probe 1 can be used to detect different concentrations of intracellular thiols in living cells.
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