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A kind of sulfur dioxide derivative fluorescent probe and its preparation method and application

A technology for fluorescent probes and sulfur dioxide, applied in chemical instruments and methods, fluorescence/phosphorescence, organic chemistry, etc., can solve problems such as impact, poor selectivity of probes, hindering the development of sulfur dioxide derivatives detection, etc., to reduce interference and damage , the effect of high yield

Active Publication Date: 2021-07-13
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, optical probes of sulfur dioxide derivatives have developed rapidly in recent years. Such fluorescent probes include addition of acetylacetonate, addition of aldehyde groups, Michael addition of other double bonds, and isomerization of C=N bonds. The poor selectivity of the probes of these compounds is easily affected by other affinity substances in the organism, which has become a key problem hindering the development of sulfur dioxide derivatives detection.

Method used

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  • A kind of sulfur dioxide derivative fluorescent probe and its preparation method and application
  • A kind of sulfur dioxide derivative fluorescent probe and its preparation method and application
  • A kind of sulfur dioxide derivative fluorescent probe and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] A kind of synthetic method of fluorescent probe, concrete steps are as follows:

[0041] (1) Synthesis of compound 1:

[0042]

[0043] Get 960mg 4-(diethylamino) salicylaldehyde (molecular formula is: C 11 h 15 NO 2 ) (5mmol) and 700mg 3-bromopropyne (molecular formula is: C 3 h 3 Br) (5.8mmol) in the round bottom flask, add DMF to make it dissolve completely, then add 750mg potassium carbonate (molecular formula is: KCO 3 ), stirred under nitrogen protection and normal temperature for 10 hours, the reaction was completed, the reaction solution was washed three times with 50mL brine, and extracted with dichloromethane, and the solvent (dichloromethane) was removed by rotary evaporator vacuum distillation to obtain a crude product. Using dichloromethane and petroleum ether as the eluent, gradient elution was carried out at a volume ratio of 1:10 to 1:2, and purification was performed on a silica gel (200-300 mesh) chromatography column to obtain 806 mg of a whit...

Embodiment 2

[0051] Fluorescent probe Probe-SO 2 Applications:

[0052] Dissolve the probe prepared in Example 1 in ethanol to make a probe mother liquor with a concentration of 1mmol / L, and dissolve 10.4mg (0.1mmol) of sodium bisulfite solid in 10mL of deionized water to obtain a concentration of 10mmol / L. Mother liquor of sulfur dioxide derivatives of L. Take 30 μ L from the probe mother liquor and add it to a 5mL centrifuge tube, add different equivalents (0-100eq) of sulfur dioxide derivative mother liquor (the equivalent refers to the molar number of sulfur dioxide derivatives in the sulfur dioxide derivative mother liquor relative to the probe mother liquor Multiples of the number of moles of the probe in the medium), diluted to 3 mL with different volumes of PBS aqueous solution (concentration 25 mmol / L, pH 7.4), and configured as a test solution with a probe concentration of 10 μmol / L containing 1% ethanol. Test the fluorescence spectrum change (excitation wavelength is 415nm) of...

Embodiment 3

[0055] Fluorescent probe Probe-SO 2 Applications:

[0056] Take 30 μL from the fluorescent probe mother solution in Example 2 and add it to a 5mL centrifuge tube, add 30 μL of sulfur dioxide derivative mother solution with a concentration of 100mmol / L, and then dilute to 3mL with 3ml PBS aqueous solution (concentration 25mmol / L, pH 7.4) , prepared as a test solution with a probe concentration of 10 μmol / L and containing 1% ethanol. Using the excitation wavelength of 525nm, test its fluorescence spectrum changing with time. Depend on Figure 8 It can be seen that as time increases, the fluorescence intensity at 525 nm gradually increases and reaches the maximum within 5 seconds.

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Abstract

The invention discloses a fluorescent probe for fast and highly selective detection of sulfur dioxide derivatives. Its structural formula is as formula (I). The highly selective real-time detection of sulfur dioxide derivatives at the cellular level can avoid the interference of impurity ions; it is of great significance to the study of the physiological and pathological effects of sulfur dioxide derivatives.

Description

technical field [0001] The invention belongs to the technical field of preparation of organic small molecule fluorescent probes, and in particular relates to a sulfur dioxide derivative fluorescent probe and its preparation method and application. Background technique [0002] Sulfur dioxide is one of the air pollution gases, and it is also the fourth biological signal molecule after carbon monoxide, nitrogen monoxide, and hydrogen sulfide. It is easy to form sulfite and bisulfite when dissolved in water. This type of sulfite can resist oxidation. , Inhibit bacterial growth, prevent enzymatic browning, and are often used as bleaching agents, preservatives and antioxidants in food processing. But ingesting high doses of sulfites can cause diarrhea, hypotension, allergies, asthma and other adverse reactions in humans, and it is even related to lung cancer, cardiovascular diseases and neurological diseases. This may be related to the nucleophilic reaction of sulfite or bisulfi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/052C09K11/06G01N21/64
CPCC07D491/052C09K11/06C09K2211/1029C09K2211/1088G01N21/6428G01N21/643G01N2021/6432
Inventor 陈华蔡方圆侯波沈星灿
Owner GUANGXI NORMAL UNIV
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