Preparation method and application of benzoquinoline ratio-type near-infrared fluorescent molecular probe capable of being used for fluorine ion detection

A fluorescent molecular probe, benzoquinoline technology, applied in the field of chemical analysis and detection, can solve the problems of large fluorescence detection error, short probe emission wavelength, poor biocompatibility, etc., and achieve low cytotoxicity, low cost, and specificity strong effect

Active Publication Date: 2021-06-22
HUNAN TARGETING DETECTION TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the emission wavelength of this probe is relatively short, and it is in the visible light region, which is easy to cause fluorescence self-quenching and low signal-to-noise ratio, resulting in large errors in fluorescence detection and low sensitivity.
At the same time, the probe has poor water solubility and poor biocompatibility, which limit its further application in vivo

Method used

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  • Preparation method and application of benzoquinoline ratio-type near-infrared fluorescent molecular probe capable of being used for fluorine ion detection
  • Preparation method and application of benzoquinoline ratio-type near-infrared fluorescent molecular probe capable of being used for fluorine ion detection
  • Preparation method and application of benzoquinoline ratio-type near-infrared fluorescent molecular probe capable of being used for fluorine ion detection

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Synthesis of compound 1

[0027] 10-Hydroxybenzo[H]quinoline (585.6 mg, 2.5mmol) and hexamethylimine (1680 mg, 10mmol) were added in a 25mL round bottom flask, then 25mL trifluoroacetic acid was added to the reaction system, and the temperature was raised to 90 o C is heated to reflux. After the reaction is over, remove the reaction, let it cool and pour it into 500mL ice water, adjust the pH to about 6 with 1 N NaOH solution, a large amount of precipitate precipitates, filter, collect and wash the filter cake, and vacuum dry Afterwards, it was purified by column chromatography to obtain 512.4 mg of the product with a yield of 76.5%.

[0028] Synthesis of Compound 2

[0029] Compound 1 (446.4 mg, 2 mmol) was added in 10 mL of ethanol in a 25 mL round-bottomed flask, and after fully dissolving, 2-picoline salt (702 mg, 2.75 mmol) and 1 mmol of piperidine were added to the reaction system, and the temperature was raised to 90 o C heated to reflux. After the reaction, ...

Embodiment 2

[0033] The experiment of the relationship between the fluorescence intensity of fluorescent probe and the concentration of fluoride ion

[0034] Accurately weigh 554.5 mg of the target fluorescent molecular probe with a purity of more than 99% prepared in Example 1 and dissolve it in an acetonitrile solution to prepare a 1 mM probe mother solution. Take the fluorescent probe mother solution, divide it into 8 groups, each group is 10mL, add different concentrations of fluoride ion solution, adjust the concentration of the probe molecule in the solution to 10μM, and the concentration of fluoride ion is 1μM, 2μM, 5μM, 10μM respectively , 20 μM, 30 μM, 40 μM, 50 μM. After incubation at room temperature for 20 min, the fluorescence spectra of different systems were tested in 10 mm cuvettes. The results are attached figure 1 It shows that after adding fluoride ions, the fluorescence intensity at 498 nm of the detection system gradually weakens, and the fluorescence intensity at 63...

Embodiment 3

[0036] Selectivity Experiment of Fluorescent Probes to Fluoride Ions

[0037] Take the fluorescent probe solution and divide it into 10 groups, 10mL in each group, among which 1 group does not add the analyte, and 9 groups add CO 3 2 -, SO 4 2 -, NO 3 -, Cl-, I-, Br-, CH 3 COO-, PO 4 3 -, F-solutions, so that the concentration of probe molecules in each group of solutions is 10 μM, the concentration of F- is 50 μM, and the concentration of other anions is 100 μM. After incubating at room temperature for 20 min, test the fluorescence spectra of different systems in 10 mm cuvettes, record the fluorescence intensities at 637 nm and 498 nm and calculate the I 637 nm / I 498 nm value. The results are attached figure 2 Display: It is found that only when fluoride ion is added, I 637 nm / I 498 nm There was a significant change in the value of , but when other test substances were added, there was only a weak or no change in the fluorescence. It shows that the fluorescent...

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Abstract

The invention discloses a preparation method and application of a benzoquinoline ratio type near-infrared fluorescent molecular probe capable of being used for fluorine ion detection. The chemical structural formula of the benzoquinoline ratio type near-infrared fluorescent molecular probe is formula I shown in the specification. The ratio type fluorescent probe takes a 10-hydroxybenzo[H]quinoline derivative as a parent structure, and the detection of fluorine ions in a pure water system and a biological system is realized based on an ESIPT mechanism. The maximum emission wavelength of the probe molecule in a PBS buffer solution is 498 nm, after fluorine ions are added, the maximum emission wavelength of the probe is subjected to red shift to 637 nm and is in a near-infrared region, and the interference of biological autofluorescence can be effectively avoided. Meanwhile, the fluorescent molecular probe disclosed by the invention is good in water solubility, high in sensitivity and strong in specificity, and has a relatively strong practical application value in the fields of environment and life science.

Description

technical field [0001] The invention relates to the technical field of chemical analysis and detection, in particular to a preparation method of a benzoquinoline-based ratiometric near-infrared fluorescent molecular probe and the application of the fluorescent molecular probe in detecting fluoride ions. Background technique [0002] Fluoride ion is one of the elements necessary for the human body, and it is also the smallest anion, with unique properties such as strong corrosion. An appropriate amount of fluoride can prevent dental caries and treat osteoporosis, so it is widely used in toothpaste, medicine and even drinking water. However, due to the extremely slow metabolism of fluoride ions in the human body, excessive intake of fluorine will cause permanent and irreversible damage to the human body, such as fluorosis, urolithiasis, and even death. The U.S. Environmental Protection Agency (EPA) has set a Maximum Contaminant Level (MCL) for fluoride ions in drinking water ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07F7/18G01N21/64
CPCC09K11/06C07F7/1804C07F7/188G01N21/6428G01N21/643C09K2211/1029
Inventor 不公告发明人
Owner HUNAN TARGETING DETECTION TECH CO LTD
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