Camphor-based ketoxime fluorescent probe for detecting hypochlorous acid as well as preparation method and application of camphor-based ketoxime fluorescent probe

A technology for detecting hypochlorous acid and camphor-based ketoxime, which is applied in oxime preparation, fluorescence/phosphorescence, chemical instruments and methods, etc., to achieve simple synthesis, good application value, and high sensitivity

Pending Publication Date: 2022-05-13
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Using 3-(9-anthracenemethylene)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one as a raw materia

Method used

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  • Camphor-based ketoxime fluorescent probe for detecting hypochlorous acid as well as preparation method and application of camphor-based ketoxime fluorescent probe
  • Camphor-based ketoxime fluorescent probe for detecting hypochlorous acid as well as preparation method and application of camphor-based ketoxime fluorescent probe
  • Camphor-based ketoxime fluorescent probe for detecting hypochlorous acid as well as preparation method and application of camphor-based ketoxime fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] The preparation of 3-(9-anthracene methylene)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one oxime, the reaction formula is as follows:

[0019]

[0020] Specific steps are as follows:

[0021] Preparation of 3-(9-anthracenemethylene)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one oxime:

[0022] 1.5mmol 3-(9-anthracene methylene)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one, 6.0mmol hydroxylamine hydrochloride, 7.5mmol sodium hydroxide, 30mL absolute ethanol In a three-necked flask equipped with a stirrer, the reaction was refluxed at 80°C for 48h. After the solvent was recovered from the reaction solution by distillation, the crude product of 3-(9-anthracene methylene)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one oxime was obtained, and then passed through a silica gel chromatography column ( Petroleum ether: ethyl acetate = 4:1) chromatography and methanol recrystallization to obtain yellow powder 3-(9-anthracene methylene)-1,7,7-trimethylbicyclo[2.2.1]hept-2- Ketoxime, the yi...

Embodiment 2

[0024] Prepare 3-(9-anthracene methylene)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one oxime to 1.5×10 -6 M's PBS buffer solution, dissolve cysteine ​​in PBS buffer solution to make the concentration 0, 1.0×10 -5 , 2.0×10 -5 , 4.0×10 -5 , 6.0×10 -5 , 8.0×10 -5 , 10.0×10 -5 , 12.0×10 -5 , 14.0×10 -5 , 16.0×10 -5 , 18.0×10 -5 M's solution. Adopt fluorescence spectrometric titration to measure on the fluorescence spectrophotometer under the hypochlorous acid action of different concentrations 3-(9-anthracene methylene)-1,7,7-trimethylbicyclo[2.2.1]heptane Fluorescence emission spectra of 2-ketoximes, such as figure 1 shown. The results show that with the gradual increase of the concentration of hypochlorous acid in the solution, the fluorescence emission intensity of the probe at 453nm is gradually enhanced, thus indicating that the compound can be used as a fluorescent probe for sensitively detecting the content of hypochlorous acid in the solution.

Embodiment 3

[0026] Prepare 3-(9-anthracene methylene)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one oxime to 1.5×10 -6 M's PBS buffer solution, and different metal ions, anions and active oxygen were dissolved in PBS buffer to prepare a concentration of 1.8×10 - 4 M's solution. Fluorescence spectrometry was used to measure the concentration of 3-(9-anthracene methylene)-1,7,7-trimethylbicyclo[2.2.1]heptane under the action of different metal ions, anions and active oxygen on a fluorescence spectrophotometer. - Fluorescence emission spectra of 2-ketoximes, such as figure 2 shown. The results show that the addition of hypochlorous acid will significantly increase the fluorescence emission intensity of the probe at 453nm, while the addition of other metal ions (Na + , Cu 2+ , Zn 2+ , Mg 2+ , Al 3+ , Cd 2+ ), anion (F - , SO 3 2- , CO 3 2- , AcO - , NO 2 - ) and reactive oxygen species ( 1 o 2 , H 2 o 2 , ONOO - ) and other reference comparison observations, the fluorescenc...

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PUM

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Abstract

The invention discloses a camphor-based ketoxime fluorescent probe for detecting hypochlorous acid as well as a preparation method and application of the camphor-based ketoxime fluorescent probe. The fluorescent probe is 3-(9-anthracene methylene)-1, 7, 7-trimethyl bicyclo [2.2. 1] heptyl-2-ketoxime, and the structural formula of the fluorescent probe is shown in the description. According to the invention, 3-(9-anthracene methylene)-1, 7, 7-trimethyl bicyclo [2.2. 1] heptyl-2-ketone is used as a raw material, and the 3-(9-anthracene methylene)-1, 7, 7-trimethyl bicyclo [2.2. 1] heptyl-2-ketoxime is obtained by carrying out condensation reaction on the 3-(9-anthracene methylene)-1, 7, 7-trimethyl bicyclo [2.2. 1] heptyl-2-ketone and hydroxylamine hydrochloride. The compound can selectively react with hypochlorous acid, and the fluorescence color of a probe solution is changed from colorless to bright blue under the irradiation of 365nm ultraviolet light, so that the compound can be used as a fluorescent probe for selectively detecting hypochlorous acid, the probe can quickly and sensitively detect the content of hypochlorous acid in the solution, the detection range is 0-180 mu M, and the application prospect is broad. The detection limit is as low as 1.18 * 10 <-7 > M, the detection time is less than 5 s, and the method has a good application prospect.

Description

technical field [0001] The invention belongs to the technical field of fine organic synthesis, and relates to a camphor-based ketoxime fluorescent probe for detecting hypochlorous acid and a preparation method and application thereof. Background technique [0002] Hypochlorous acid is one of the important reactive oxygen species in living organisms, and plays a vital role in maintaining intracellular redox balance. In addition, hypochlorous acid also plays a role in resisting the invasion of bacteria, viruses, and pathogenic microorganisms in the immune system of organisms. However, excess hypochlorous acid can cause oxidative stress, leading to various diseases such as rheumatoid arthritis, atherosclerosis, cardiovascular disease, kidney disease, acute lung injury, and cancer. Therefore, it is of great significance to develop an analytical method that can identify and accurately detect hypochlorous acid. [0003] At present, the methods for detecting hypochlorous acid mai...

Claims

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Application Information

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IPC IPC(8): C07C249/08C07C251/44C09K11/06G01N21/64
CPCC07C251/44C09K11/06G01N21/6428C09K2211/1011C07C2602/42
Inventor 王石发王忠龙张燕徐徐杨益琴李明新巩帅孟志远梁越寅
Owner NANJING FORESTRY UNIV
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