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Near-infrared fluorescent molecular probe for detecting hydrogen sulfide and preparation method and application of near-infrared fluorescent molecular probe

A fluorescent molecular probe, near-infrared technology, applied in chemical instruments and methods, fluorescence/phosphorescence, material analysis by optical means, etc., can solve the problems of autofluorescence interference, difficult fluorescence, etc. Strong and responsive effect

Inactive Publication Date: 2020-01-14
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Most of the traditional fluorescent probes for detecting hydrogen sulfide are short-wavelength. The fluorescence generated by this probe after reacting with hydrogen sulfide is difficult to show through the living body, and there is a lot of interference from autofluorescence

Method used

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  • Near-infrared fluorescent molecular probe for detecting hydrogen sulfide and preparation method and application of near-infrared fluorescent molecular probe
  • Near-infrared fluorescent molecular probe for detecting hydrogen sulfide and preparation method and application of near-infrared fluorescent molecular probe
  • Near-infrared fluorescent molecular probe for detecting hydrogen sulfide and preparation method and application of near-infrared fluorescent molecular probe

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Experimental program
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Effect test

Embodiment 1

[0036] Preparation of near-infrared fluorescent probes for detecting hydrogen sulfide:

[0037] Add a certain amount of compound 1 into a round bottom flask, slowly add N,N-dimethylformamide in ice bath and nitrogen protection, after cooling for 10min, start stirring, and slowly add in ice bath and nitrogen protection After tert-butyl nitrite was stirred for 5 minutes, trimethylsilyl azide was slowly added under the conditions of ice bath and oxygen protection. After stirring for 10 minutes, remove the ice bath, put it into an oil bath, stir and heat to 80 degrees Celsius. React for a period of time, wait for the solution to turn blue, cool the system, pour the reaction solution in the bottle into the separatory funnel, add distilled water, after fully mixing, add dichloromethane, continue to shake for 5 minutes, let the separatory funnel stand, wait After the solution was separated in the separatory funnel, the solution in the lower layer was evaporated to dryness by vacuum ...

Embodiment 2

[0042] Near-infrared fluorescent probe and hydrogen sulfide in vitro response to ultraviolet absorption and fluorescence emission measurement experiments:

[0043] Weigh 4.7mg probe and dissolve it in 1mL DMSO to make 10mM probe stock solution. Weigh 5.6mg NaHS and dissolve it in 10mL water to make 10mM NaHS mother solution. Prepare eight 5mL centrifuge tubes, add 3mL of PBS buffer solution (pH=7.4) to each centrifuge tube in turn, and then add 3 μL of probe mother solution. At this time, the probe concentration in each centrifuge tube is 10 μM. After fully mixing, add 0, 6, 12, 18, 24, 30, 36, 42 μL of NaHS mother solution to each centrifuge tube respectively, and after reacting for 20 minutes, add them to the cuvette in order for UV absorption and fluorescence emission. Detection (excitation light wavelength is 690nm), the obtained data are processed by origin software figure 2 , indicating that the probe responds well to hydrogen sulfide in solution.

Embodiment 3

[0045] MTT biocompatibility experiment between near-infrared fluorescent probe and U87 cells:

[0046] PBS solution was added to the periphery of the 96-well plate, and the remaining inner wells were covered with U87 cells, and cultured for 12 hours. Weigh 4.7mg of the probe and dissolve it in 5mL of biological DMSO solution to prepare a 2mM biological probe stock solution. Prepare 5mg / mL MTT solution. Prepare six 5mL centrifuge tubes, add 2mL medium to each, and add 0, 2, 4, 6, 8, 10 μL of biological probe master solution to the centrifuge tubes in sequence. Pipette 190 μL of the solution in the 6 centrifuge tubes and add the same concentration to the 6 rows of wells in sequence and incubate for 24 hours, then add 10 μL of MTT solution to each well. Continue to incubate for 3 hours, discard the medium in the liquid, and add 100 μL DMSO solution to each well. After fully dissolving, carry out ultraviolet absorption detection (detection wavelength is 490nm). Data processing...

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Abstract

The invention discloses a near-infrared fluorescent molecular probe for detecting hydrogen sulfide and a preparation method and application of the near-infrared fluorescent molecular probe. The near-infrared fluorescent molecular probe has a molecular formula of C31H29N4O+, and has a structure formula shown in the description. Compared with the prior art, the near-infrared fluorescent molecular probe disclosed by the invention is good in selectivity and good in response effect on hydrogen sulfide, and in addition, can be well applied to living imaging and the like because of the properties ofnear-infrared absorption and fluorescence emission. In addition, the near-infrared fluorescent molecular probe is simple in synthesis process, low in cost and high in yield.

Description

technical field [0001] The invention relates to a near-infrared fluorescent molecular probe for detecting hydrogen sulfide, a preparation method and application thereof, and belongs to the technical field of fluorescent molecular probes. Background technique [0002] Hydrogen sulfide is an inorganic compound with the smell of rotten eggs, usually in gaseous state. After nitric oxide and carbon monoxide, hydrogen sulfide is the third discovered gas signal molecule with physiological regulation function, which is involved in many physiological processes in organisms, including vasodilation, angiogenesis, oxygen sensing, cell apoptosis, tissue Inflammation, neuromodulatory processes, etc. Changes in the concentration of hydrogen sulfide in organisms are often related to some diseases, including Alzheimer's disease, Down's syndrome, diabetes and coronary heart disease. Although the mechanism of action of hydrogen sulfide in the body is not clear, its accurate detection is very...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D405/06G01N21/64
CPCC07D405/06C09K11/06C09K2211/1029C09K2211/1088G01N21/6428G01N21/643
Inventor 刘熠姚旭烽高玉慧
Owner CHINA PHARM UNIV
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