Citation: GUO Jing, LIU Qing-Wen, DU Jian-Shi, KONG Xiang-Yi, SONG Yan, YANG Qing-Biao, ZHAO Qing, LI Yao-Xian. Synthesis of Naphthalimide-based Biothiols Probe and Detection of Amino Acids Containing Sulfhydryl Groups[J]. Chinese Journal of Analytical Chemistry, ;2017, 45(9): 1330-1338. doi: 10.11895/j.issn.0253-3820.170319 shu

Synthesis of Naphthalimide-based Biothiols Probe and Detection of Amino Acids Containing Sulfhydryl Groups

1.
Department of Neurology, China-Japan Union Hospital of Jilin University, Changchun 130033, China;2 College of Chemistry, Jilin University, Changchun 130021, China

Received Date: 19 May 2017
Revised Date: 20 July 2017

A novel probe (DNSBN) towards biothiols on the basis of 4-hydroxynaphthalimide as fluorophores and 2, 4-dinitrobenzenesulfonyloxy group as specific recognition site was designed and synthesized. The result of absorption and fluorescence spectral analyses indicated that the probe had high sensitivity and selectivity towards cysteine (Cys), homocysteine (Hcy) and glutathione (GSH), and the detection was not affected by other 17 kinds of natural amino acids. Meanwhile, it was confirmed that DNSBN was a ratiometric probe through the fluorescence titration experiment, and the fluorescent intensity at 555 nm had a high linear relationship with biothiols concentration in the range of 0-20 μmol/L. The detection limits (3σ) of Cys, Hcy and GSH were 25.9, 92.0 and 77.9 nmol/L, respectively. The absorption, emission and mass spectra indicated that biothiols could be engaged in nucleophilic substitution reaction with 2,4-dinitrobenzenesulfonate, which induced the sulfonic esters decomposed. With the departure of receptor unit, the d-PeT progress (donor-excited photoinduced electron transfer) was blocked with an obvious colorimetric and fluorescence change. Finally, HeLa cell imaging experiments verified that DNSBN had good biocompatibility and could be used to detect exogenous biothiols.
- Fluorescent probe,
- Naphthalimide,
- Cysteine,
- Homocysteine,
- Glutathione
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沈阳化工大学材料科学与工程学院沈阳 110142