Citation: BI Jing-Jing, LI Lin-Lin, MA Na-Na, XIA Ding-Ding, ZHANG Hua, ZHANG Zhi-Guo, LIU Tong-Xin, ZHANG Gui-Sheng. Novel Anthraquinone-based Fluorescent Probes for Detection of Silver Ion, Density Functional Theory and Living Cells Imaging[J]. Chinese Journal of Analytical Chemistry, ;2019, 47(2): 198-206. doi: 10.19756/j.issn.0253-3820.181563 shu

Novel Anthraquinone-based Fluorescent Probes for Detection of Silver Ion, Density Functional Theory and Living Cells Imaging

School of Chemistry and Chemical Engineering, Henan Key Laboratory of Organic Functional Molecule and Drug Innovation, Henan Normal University, Xinxiang 453007, China

Received Date: 28 August 2018
Revised Date: 2 December 2018

Fund Project: This work was supported by the National Natural Science Foundation of China (No. 21702051), the Key Project of Henan Educational Committee (No. 17A350006), State key Laboratory of Enrironmental Chemistry and Ecotoxicology, Research Center for ECO-Environmental Sciences, Chinese Academy of Sciences (No. KF2016-01) and the Henan Normal University Science Foundation for Young Scholars (No. 2016QK10).

Fluorescent sensing methods, because of their simple, cheap, fast, high selectivity and sensitivity, are widely used in the detection of cationic, anionic and other chemicals. Anthraquinone derivatives have many pharmacological activities, rigid planar structure and large ring conjugate system. They have moderate fluorescence emission wavelengths, good optical stabilities and high luminous efficiencies. In this work, anthraquinone derivatives were employed as fluorophore to prepare new fluorescent probes. Based on the mechanism of intramolecular charge transfer (ICT), a series of symmetric bis-1,2,3-triazole hydrazine derivatives K1 and K2, which were confirmed by ¹H NMR and ¹³C NMR, were designed and synthesized. The spectral properties were also investigated. The structure and theoretical spectrum of K1 were calculated using GaussView 9.0 quantization program and time-dependent density functional theory. The results showed that exhibited good selectivity to Ag⁺ in a mixed solution of DMSO/HEPES (1:7, V/V). Binding analysis using the method of continuous variations (Job's plot) established that the stoichiometry of K1-Ag⁺ complex was estimated to be 1:1. The detection limit of K2 for Ag⁺ was 21.2 μmol/L (S/N=3). A complexation mechanism of K1-Ag⁺ was proposed, which was consistent with the calculated results. The fluorescence of K1 was increased dramatically in the presence of Ag⁺, and it remained nearly constant in the range of pH 6.0-8.0. Other metal ions, such as Al³⁺, Ba²⁺, Ca²⁺, Cd²⁺, Co²⁺, Cr³⁺, Cu²⁺, Hg²⁺, Fe³⁺, K⁺, Mn²⁺, Na⁺, NH₄⁺, Ni²⁺, Pb²⁺and Zn²⁺, induced negligible fluorescence increasing for under the same conditions. The synthesized fluorescent probe K1 could be applied to image intracelluar Ag⁺ in living HepG2 cells, indicating that it was a useful tool in bioanalytical applications.
- Anthraquinone,
- Triazole,
- Fluorescence probe,
- Silver ion,
- Fluorescence imaging
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