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Ratio type fluorescent probe for detecting magnesium ions, preparation method and application thereof

A technology of fluorescent probes and detection methods, which is applied in the directions of fluorescence/phosphorescence, chemical instruments and methods, and luminescent materials, and can solve problems such as interference and the influence of accuracy of test results

Active Publication Date: 2020-10-30
QINGHAI INST OF SALT LAKES OF CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, in the design of the above-mentioned molecules, the signal of fluorescent single-peak response is basically used, which has certain limitations in practical application. The impact of objective factors such as efficiency
[0005]In addition, due to the chemical similarity of the same main group Ca2+ and Mg2+, the identification of Mg 2+ is easily interfered by Ca2+, therefore, it is still a big challenge to develop highly selective Mg2+ fluorescent probes challenge

Method used

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  • Ratio type fluorescent probe for detecting magnesium ions, preparation method and application thereof
  • Ratio type fluorescent probe for detecting magnesium ions, preparation method and application thereof
  • Ratio type fluorescent probe for detecting magnesium ions, preparation method and application thereof

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preparation example Construction

[0044] Another aspect of the embodiments of the present invention also provides the aforementioned method for preparing the ratiometric fluorescent probe for detecting magnesium ions, which includes:

[0045] Dissolve aldylated 8-hydroxyquinoline and 2-aminothiophenol in an organic solvent, then add concentrated hydrochloric acid and hydrogen peroxide, and stir at 25-35°C for 60-120 minutes to obtain ratiometric fluorescence for detecting magnesium ions probe.

[0046] In some embodiments, the formylated 8-hydroxyquinoline includes a structure shown in any one of the following formulas:

[0047]

[0048] In some embodiments, the organic solvent includes ethanol, methanol, etc., but is not limited thereto.

[0049] In some embodiments, the molar ratio of the aldylated 8-hydroxyquinoline to 2-aminothiophenol is 1:1˜1:2.

[0050] In some embodiments, the preparation method further includes: after the reaction is completed, adding water to the reaction system, stirring, filte...

Embodiment 1

[0064] Embodiment 1 The synthesis of fluorescent probe molecule L of the present invention

[0065] Dissolve 8-hydroxyquinoline-5 aldehyde (346.5mg, 2.0mmol) and 2-aminothiophenol (0.32mL, 3.0mmol) in ethanol (20mL), then add 0.5mL concentrated hydrochloric acid and 1.2mL hydrogen peroxide, 25 After stirring at ℃ for 90 minutes, 200 mL of deionized water was added, and after stirring for 5 minutes, the precipitate was filtered out, dried and recrystallized with a mixed solution of dichloromethane and ethanol to obtain the fluorescent probe L with the structure shown in the following formula: 310 mg, yield 56 %. m.p.: 180.9-182.0°C. 1 HNMR (DMSO-d 6 , 400MHz) δ=10.68(s, 1H), 9.72(d, J=8.8Hz, 1H), 8.98(d, J=4.0Hz, 1H), 8.08-8.17(m, 3H), 7.77(dd, J =8.8, 4.4Hz, 1H), 7.57(t, J=8.0Hz, 1H), 7.48(t, J=8.0Hz, 1H), 7.24(d, J=8.0Hz, 1H)ppm. 13 C NMR (DMSO-d 6 , 100MHz) δ=166.9, 156.3, 153.8, 148.7, 138.5, 134.6, 133.9, 132.0, 126.5, 126.2, 125.4, 123.4, 122.8, 121.9, 119.8, 111.2pp...

Embodiment 2

[0067] Embodiment 2 The synthesis of fluorescent probe molecule L of the present invention

[0068] Dissolve 8-hydroxyquinoline-5 aldehyde (346.5mg, 2.0mmol) and 2-aminothiophenol (0.21mL, 2.0mmol) in ethanol (20mL), then add 0.5mL concentrated hydrochloric acid and 1.2mL hydrogen peroxide, 30 After stirring at ℃ for 90 minutes, add 200 mL of deionized water, and after stirring for 5 minutes, filter out the precipitate. After drying, recrystallize with a mixed solution of dichloromethane and ethanol to obtain the fluorescent probe L with the structure shown in the following formula: 297 mg, yield 53.6 %. m.p.: 180.9-182.0°C. 1 H NMR (DMSO-d 6 , 400MHz) δ=10.68(s, 1H), 9.72(d, J=8.8Hz, 1H), 8.98(d, J=4.0Hz, 1H), 8.08-8.17(m, 3H), 7.77(dd, J =8.8, 4.4Hz, 1H), 7.57(t, J=8.0Hz, 1H), 7.48(t, J=8.0Hz, 1H), 7.24(d, J=8.0Hz, 1H)ppm. 13 C NMR (DMSO-d 6 , 100MHz) δ=166.9, 156.3, 153.8, 148.7, 138.5, 134.6, 133.9, 132.0, 126.5, 126.2, 125.4, 123.4, 122.8, 121.9, 119.8, 111.2ppm. ESI...

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Abstract

The invention discloses a ratio type fluorescent probe for detecting magnesium ions, a preparation method and application thereof. The ratio type fluorescent probe has a structure shown as the following formula in the specification, wherein R1, R2, R3 and R4 are shown in the specification, and when any one of R1, R2, R3 and R4 is shown as the specification, the rest is H. Quinoline in the ratio type fluorescent probe is used as a fluorophore and an identification group at the same time, the structure is simple, feasible and easy to synthesize, fluorescence detection of Mg<2+> can be realized through a bimodal fluorescence ratio type signal, the invention aims to solve the technical problem of fluorescence detection of magnesium ions, avoids the problems of single emission wavelength detection, interference of calcium ions and the like, can perform rapid and high-selectivity detection on Mg<2+> in a water-containing system, and has an application prospect of performing high-selectivityfluorescence detection on the magnesium ions in a multi-ion complex system.

Description

technical field [0001] The invention relates to a ratio-type fluorescent probe, in particular to a ratio-type fluorescent probe for detecting and identifying magnesium ions, a preparation method and application thereof, and belongs to the technical field of metal ion probes. Background technique [0002] Mg 2+ It is the most abundant divalent metal cation in human cells and plays an important role in physiological activities. It can participate in many physiological processes such as the synthesis of nucleic acids and proteins. From a health point of view, excessive or insufficient intake of magnesium ions can lead to many diseases, such as: heart disease, neuropathy, diabetes, cardiovascular and cerebrovascular diseases, and Parkinson's syndrome. At present, there are many detection methods for it, but there are still some problems to be solved. Therefore, there is an urgent need for Mg 2+ Develop novel detection methods. [0003] In recent years, due to its simple synt...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/04C09K11/06G01N21/64
CPCC07D417/04C09K11/06G01N21/6428C09K2211/1029C09K2211/1037
Inventor 付振海张志宏李志伟张永明赵冬梅苏彤
Owner QINGHAI INST OF SALT LAKES OF CHINESE ACAD OF SCI