Citation: Li Changwei, Yang Dong, Yin Bing, Guo Yuan. Novel Coumarin-Based Fluorescent Probes for Detecting Zn²⁺ in Living Cells[J]. Chinese Journal of Organic Chemistry, ;2016, 36(4): 787-794. doi: 10.6023/cjoc201511016 shu

Novel Coumarin-Based Fluorescent Probes for Detecting Zn²⁺ in Living Cells

1.
College of Chemistry and Materials Science, Northwest University, Xi'an 710127

Corresponding author: Guo Yuan,
Received Date: 10 November 2015
Available Online: 8 December 2015
Fund Project: 国家自然科学基金(Nos.21472148,21072158) (Nos.21472148,21072158)陕西省教育厅专项基金(No.12JK0580) (No.12JK0580)

Zinc ion (Zn²⁺) is one of the most important transition-metal ions in the human body which is involved in many important life activities and many diseases can be displayed by its situation. Thus, monitoring of Zn²⁺ is very meaningful to diagnosis of diseases. Compared to the traditional detection methods, fluorescence probe is safer and more practical. Because coumarin derivatives possess several advantages in optics, we choose them as key structures to prepare new fluorescent probes. Based on the mechaism of photoinduced electron transfer (PET), the water-soluble fluorescent probes 1 and 2that are coumarin-based derivatives were designed, which demonstrated sensitivity for Zn²⁺ and exhibited high selectivity to Zn²⁺ over other metal ions. The receptor unit serves as an electron donor in the absence of Zn²⁺, quenching the fluorophore excited state that makes the probe have no fluorescence. However, when Zn²⁺ binds to the receptor, photoinduced electron transfer is prevented and the quenching is blocked, resulting the fluorescence intensity significantly enhanced. There is a good correlation between fluorescence intensity and Zn²⁺ concentration. With the increase of Zn²⁺ concentration, fluorescence intensity becomes stronger. Furthermore, the two probes were successfully labelled on the MCF-7 cell and B. subtilis. The single crystals of the coumarin-based compounds 1~4 and zinc complex [Zn(2)] were also obtained. The X-ray crystal structure of the zinc complex [Zn(2)] reveals that the hydroxyl group and the 2,2-dipicolylaminomethyl group participate in coordination. Zn²⁺ is five-coordinated with three nitrogen atoms from the pyridine rings, the substituted amino group and two oxygen atoms from the 7-site hydroxyl group, also coordinated with water molecule forming a pentacoordinated bipyramid geometry.
- coumarin,
- Zn²⁺ fluorescent probe,
- cell imaging
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Novel Coumarin-Based Fluorescent Probes for Detecting Zn2+ in Living Cells

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Novel Coumarin-Based Fluorescent Probes for Detecting Zn²⁺ in Living Cells