Viscosity Fluorescent Probes Based on Quinoline Group and Its Applications

doi:10.6023/A23040138

Acta Chimica Sinica ›› 2023, Vol. 81 ›› Issue (8): 905-911.DOI: 10.6023/A23040138 Previous Articles Next Articles

Article

喹啉基粘度荧光探针的合成及其检测应用

武虹乐, 郭锐, 迟涵文, 唐永和, 宋思睿, 葛恩香, 林伟英^*()

广西大学光功能材料与化学生物学研究院广西电化学能源材料重点实验室广西大学化学化工学院省部共建特色金属材料与组合结构全寿命安全国家重点实验室广西南宁 530004

投稿日期:2023-04-20 发布日期:2023-09-14
基金资助:
国家自然科学基金(21877048); 国家自然科学基金(22077048); 国家自然科学基金(22277014); 国家自然科学基金(22104019); 广西壮族自治区自然科学基金(2019GXNSFBA245068); 广西壮族自治区自然科学基金(2021GXNSFDA075003); 广西壮族自治区自然科学基金(AD21220061); 广西大学启动基金(A3040051003)

Viscosity Fluorescent Probes Based on Quinoline Group and Its Applications

Hongyue Wu, Rui Guo, Hanwen Chi, Yonghe Tang, Sirui Song, Enxiang Ge, Weiying Lin()

Institute of Optical Materials and Chemical Biology, Guangxi Key Laboratory of Electrochemical Energy Materials, School of Chemistry and Chemical Engineering, State Key Laboratory of Featured Metal Materials and Life-cycle Safety for Composite Structures, Guangxi University, Nanning, Guangxi 530004

Received:2023-04-20 Published:2023-09-14
Contact: *E-mail: weiyinglin2013@163.com
Supported by:
National Natural Science Foundation of China(21877048); National Natural Science Foundation of China(22077048); National Natural Science Foundation of China(22277014); National Natural Science Foundation of China(22104019); Natural Science Foundation of Guangxi Province(2019GXNSFBA245068); Natural Science Foundation of Guangxi Province(2021GXNSFDA075003); Natural Science Foundation of Guangxi Province(AD21220061); Startup Fund of Guangxi University(A3040051003)

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Abstract

As one of the important parameters of biological microenvironment, viscosity is closely related to many life activities, when diseases appear in the organism, such as pneumonia, diabetes, Alzheimer's disease, atherosclerosis, malignant tumors, etc., the cytoplasmic viscosity in the organelle also changes, the new crown pneumonia is becoming more and more serious, and it is urgent to detect the viscosity in the organism. Based on the fluorescence mechanism of twisted intramolecular charge transfer (TICT), a viscosity-mediated fluorescent probe QUI-VI is rationally designed and constructed, and its related properties are explored and applied to detect physiological viscosity changes in vivo to achieve the purpose of disease monitoring. The two conjugates were connected by the carbon-carbon double bond formed by the condensation of aminotrinitrobenzene and benzopyridine quaternary ammonium salts by methyl and aldehyde groups, forming a large conjugated system. This not only increases the free transfer of electrons in the conjugated system, so that the constructed probe molecules have a long emission wavelength, but also regulates the fluorescence signal of the probe molecules because the freely rotatable carbon-carbon double bond can respond to the change of viscosity. The regulation process is: when QUI-VI is in a high-viscosity environment, the free rotation of the carbon-carbon double bond is greatly limited, so that the two conjugated systems on the molecule are in the same plane, at this time, the probe molecule is the lowest energy state, when irradiated by 450 nm light, absorb one photon energy. The molecule is excited in the excited state, and can emit long-wavelength fluorescence when transitioning back to the ground state. On the contrary, when it is in a medium with low viscosity, the free rotation of the carbon-carbon double bond is no longer hindered, and when the two conjugated systems rotate to the same plane perpendicularly, they are in the highest energy state, and the molecules emit shorter wavelengths of fluorescence when absorbing the energy of a photon and transitioning back to the ground state, that is, it is blue-shifted by 10 nm on the fluorescence spectrum. All in all, the fluorescence change of the probe QUI-VI constructed based on the TICT mechanism is controllable.

Key words: viscosity, fluorescent probes, fluorescence imaging, pneumonia, quinolone

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Hongyue Wu, Rui Guo, Hanwen Chi, Yonghe Tang, Sirui Song, Enxiang Ge, Weiying Lin. Viscosity Fluorescent Probes Based on Quinoline Group and Its Applications[J]. Acta Chimica Sinica, 2023, 81(8): 905-911.

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Fig. & Tab. 11

Scheme 1. The mechanism of QUI-VI

Scheme 2. Synthetic route of QUI-VI Reagents and conditions: (i) Compound 1, tetrahydrofuran, aqueous ammonia, 25 ℃, 1 h. (ii) Compound 3, iodoethane, acetonitrile, 85 ℃, 12 h. (iii) Compound 2, compound 4, methanol, 65 ℃, 1 h

Figure 1. (A) UV absorption spectra of QUI-VI (10 μmol/L) in different polar solvents. (B) Fluorescence emission spectra of QUI-VI (10 μmol/L) in different polar solvents (λem=450 nm)

Figure 2. Fluorescence emission spectra of QUI-VI (10 μmol/L) in glycerol-water mixed solvent system (λem=450 nm)

Figure 3. Fluorescence emission histograms of QUI-VI (10 μmol/L) in solution systems of different inorganic ions and amino acids The numbers represent: 1. NaClO; 2. L-Cys; 3. NaF; 4. GSH; 5. H2O2; 6. DL-Hcy; 7. KI; 8. MgCl2; 9. MnCl2; 10. Na2S; 11. Na2SO4; 12. ZnCl2; 13. L-Met; 14. TBHP; 15. L-Arg; 16. L-Lys; 17. Na2SO3 (λem=450 nm)

Figure 4. (A) Confocal imaging of four different cell lines treated with QUI-VI (10 μmol/L) and OA (400 μmol/L) (λex=580 nm, λem=610~750 nm), scale bar=30 μm; (B) the relative fluorescence intensities of the red channels of (A) (*p<0.05)

Figure 5. (a~c) 3T3 cell imaging after treatment with probe QUI-VI (10 μmol/L) and Nys (20 μmol/L); (d~f) 3T3 cell imaging after treatment with probe QUI-VI (10 μmol/L) and Mon (20 μmol/L); (g~i) 3T3 cell imaging after treatment with probe QUI-VI (10 μmol/L); (j) fluorescence intensity comparison chart of three groups of cell imaging

Figure 6. (a~c) 4T1 cell imaging after treatment with probe QUI-VI (10 μmol/L) and Nys (20 μmol/L); (d~f) 4T1 cell imaging after treatment with probe QUI-VI (10 μmol/L) and Mon (20 μmol/L); (g~i) 4T1 cell imaging after treatment with probe QUI-VI (10 μmol/L); (j) fluorescence intensity comparison chart of three groups of cell imaging

Figure 7. (a~c) HL-7702 cell imaging after treatment with probe QUI-VI (10 μmol/L) and Nys (20 μmol/L); (d~f) HL-7702 cell imaging after treatment with probe QUI-VI (10 μmol/L) and Mon (20 μmol/L); (g~i) HL-7702 cell imaging after treatment with probe QUI-VI (10 μmol/L); (j) fluorescence intensity comparison chart of three groups of cell imaging

Figure 8. (a~c) HepG-2 cell imaging after treatment with probe QUI-VI (10 μmol/L) and Nys (20 μmol/L); (d~f) HepG-2 cell imaging after treatment with probe QUI-VI (10 μmol/L) and Mon (20 μmol/L); (g~i) HepG-2 cell imaging after treatment with probe QUI-VI (10 μmol/L); (j) fluorescence intensity comparison chart of three groups of cell imaging

Figure 9. Different fluorescence intensities of probe QUI-VI in (A) normal lung and (B) pneumonia; (C) comparative diagram of the fluorescence intensity of probe QUI-VI in different lungs

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喹啉基粘度荧光探针的合成及其检测应用

Viscosity Fluorescent Probes Based on Quinoline Group and Its Applications

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