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A kind of fluorescent probe molecule and its preparation method and application

A technology of fluorescent probes and molecules, which is applied in the field of fluorescent probe molecules and their preparation, can solve the problems of lack of detection and achieve the effects of simple steps, high sensitivity and good selectivity

Active Publication Date: 2022-06-07
YUNNAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] However, the above only discloses that the fluorescent probe can detect hypochlorous acid and hydrogen sulfide at the same time, but the detection of other important related substances is still relatively lacking, such as hypochlorous acid and pH

Method used

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  • A kind of fluorescent probe molecule and its preparation method and application
  • A kind of fluorescent probe molecule and its preparation method and application
  • A kind of fluorescent probe molecule and its preparation method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0049] Synthesis of Fluorescent Probe Molecules Based on Methylene Blue-4-aminonaphthalimide Derivatives figure 1 )

[0050] (1) Preparation of compound 4: methylene blue (5.0 g, 15.66 mmol) and sodium carbonate (6.64 g, 62.52 mmol) were dissolved in distilled water (30 mL) and dichloromethane (20 mL), stirred at room temperature for 35 minutes, and then added thereto Slowly add sodium thiosulfate (10.98g, 62.52mmol) water (40mL) solution, continue to stir until the solution turns yellow, after cooling the above solution with an ice-water bath, slowly add bis(trichloromethyl)carbonate dropwise to it (2.78 g, 9.38 mmol) in dichloromethane (13 mL), continue stirring for 1 hour, then pour into ice water, extract with dichloromethane, dry the organic phase, filter, distill under reduced pressure, and collect the obtained crude product through Silica gel chromatography column, eluted with n-hexane:dichloromethane=3:1, to obtain 2.7 g of white solid compound 4 in a yield of 50%. ...

Embodiment 2

[0055] This example investigates the selectivity of the fluorescence detection of hypochlorous acid recognition sites based on methylene blue-4-aminonaphthalimide derivatives.

[0056] DMF:PBS (0.01mol / L, pH=7.4)=9:1 (v:v) solution was used to control the experimental conditions.

[0057] The methylene blue-4-aminonaphthalimide derivative was added to DMF solvent to prepare a solution with a concentration of 20 μmol / L of fluorescent probe molecules.

[0058] Divide the sample bottles into 14 groups, and add 20 μmol / L fluorescent probe molecule solution based on methylene blue-4-aminonaphthalimide derivatives to each sample bottle respectively. The first bottle solution is used as a blank group, and the other 13 groups are added respectively 1200μmol / L HClO, NO, HSO 3 - , SO 3 2- , H 2 S, H 2 O 2 , NO 3 - , ONOO - , OH, 1 O 2 , Cys, GSH, Hcy solution. After preparing the liquid to be tested at room temperature, transfer each test working liquid to a standard quartz...

Embodiment 3

[0060] This example investigates the quantitative fluorescence detection of hypochlorous acid based on methylene blue-4-aminonaphthalimide derivative fluorescent probe molecules.

[0061] The experimental conditions were controlled by using ethanol:PBS (0.01mol / L, pH=7.4)=9:1 (v:v) solution.

[0062] The fluorescent probe molecules based on methylene blue-4-aminonaphthalimide derivatives were prepared into a solution with a concentration of 20 μmol / L. HClO solutions of different solubility were added to it. After preparing the liquid to be tested at room temperature, transfer each test working liquid to a standard quartz cuvette of 1 cm × 1 cm, and measure its fluorescence spectrum. The slit size of the fluorescence test grating is 5nm×5nm. Image 6 The fluorescence spectrum of the fluorescent probe molecule based on the methylene blue-4-aminonaphthalimide derivative involved in the present invention changes with the concentration of hypochlorous acid in an aqueous solution ...

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Abstract

The invention provides a fluorescent probe molecule, relates to the technical field of organic functional materials, and is used for simultaneously monitoring hypochlorous acid and pH; a fluorescent probe molecule is a methylene blue-4-aminonaphthalimide derivative, which has the The amide group that reacts with acid, and the o-phenylenediamine group that responds to the pH value; HClO has a strong oxidizing property, which can break the amide bond in the fluorescent probe molecule, generate an unstable intermediate, and finally release A positively charged methylene blue fluorophore is produced, and fluorescence (690nm) appears in the near-infrared region; when the proton is combined with the 4-position o-phenylenediamine, the PET effect is suppressed, resulting in yellow-green fluorescence (525nm), thereby achieving double recognition Site selective recognition and simultaneous detection of hypochlorous acid and pH value; the invention also provides a preparation method and application of a fluorescent probe molecule; the fluorescent probe molecule is used for detecting hypochlorous acid and pH in multiple cells.

Description

technical field [0001] The invention relates to the technical field of organic functional materials, and more particularly, to a fluorescent probe molecule and a preparation method and application thereof. Background technique [0002] Optical probe molecular imaging technology has good application prospects in the field of surgery and biomedicine. In recent years, fluorescence imaging technology has achieved rapid development. Due to its convenient, non-invasive, real-time in-situ dynamic visual monitoring of biological samples, high sensitivity and high temporal and spatial resolution, it has gradually become an important research field of biological fluorescent probes. tool. [0003] Fluorescent probes for the detection of biologically active small molecules (reactive oxygen species (ROS), reactive nitrogen species (RNS), reactive sulfur (RSS), etc.) and biological in vivo fluorescence imaging research are current research hotspots. Compared with single detection fluore...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/12C09K11/06G01N21/64
CPCC07D417/12C09K11/06G01N21/643G01N21/6458C09K2211/1037C09K2211/1029C09K2211/1007
Inventor 吴相华张俊峰刘波王玉敏
Owner YUNNAN NORMAL UNIV
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