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Synthesis and application of fluorescence-enhanced fluorescent molecule probe for rapidly detecting hydrogen sulfite ions or sulfite ions

A fluorescent molecular probe and bisulfite technology, applied in the field of biochemistry, can solve problems such as human toxicity and environmental problems, and achieve the effects of low detection limit, fast detection speed and high yield

Inactive Publication Date: 2017-03-15
HUNAN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, a large amount of sulfur dioxide gas is released in modern industrial processes, which leads to serious environmental problems; and sulfur dioxide is soluble in water to form sulfite and bisulfite, which are toxic to the human body

Method used

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  • Synthesis and application of fluorescence-enhanced fluorescent molecule probe for rapidly detecting hydrogen sulfite ions or sulfite ions
  • Synthesis and application of fluorescence-enhanced fluorescent molecule probe for rapidly detecting hydrogen sulfite ions or sulfite ions
  • Synthesis and application of fluorescence-enhanced fluorescent molecule probe for rapidly detecting hydrogen sulfite ions or sulfite ions

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Embodiment 1: Preparation of Molecular Fluorescent Probe 1

[0026] 3-Ethyl-1,1,2-trimethyl-1H-benzo[e]indol-3-ium iodide 357 mg (0.97 mmol) and 2-(4-formylphenyl)phenanthroimidazole 300 mg (0.93 mmol) was dissolved in 10 ml of absolute ethanol, 2-3 drops of piperidine were added dropwise, and the reaction was stirred at room temperature for 8 hours. Then the reaction liquid was filtered, and the obtained solid was washed with absolute ethanol, and vacuum-dried to obtain 260 mg (42%) of the fluorescent molecular probe.

[0027] The proton nuclear magnetic spectrum data of above-mentioned gained probe: 1 H NMR (500 MHz, DMSO- d 6 ) δ 8.89 (s, 2H),8.62-8.65 (d, J = 16.4 Hz, 3H), 8.54 – 8.46 (m, 5H), 8.32-8.34 (d, J = 9.0Hz, 1H), 8.24-8.25 (d, J = 8.2 Hz, 1H), 8.16-8.18 (d, J = 8.9 Hz, 1H), 7.87 –7.60(m, 8H), 4.90-4.95 (q, J = 7.3 Hz, 2H), 2.09 (s, 6H), 1.58 (t, J = 7.3Hz, 3H).

Embodiment 2

[0028] Example 2: Preparation of Molecular Fluorescent Probe 1

[0029] 3-Ethyl-1,1,2-trimethyl-1H-benzo[e]indol-3-ium iodide 357 mg (0.97 mmol) and 2-(4-formylphenyl)phenanthroimidazole 300 mg (0.93 mmol) was dissolved in 10 ml of absolute ethanol, 2-3 drops of pyrrolidine were added dropwise, and the reaction was stirred at room temperature for 8 hours. Then the reaction solution was filtered, and the obtained solid was washed with absolute ethanol, and vacuum-dried to obtain 250 mg (40%) of the fluorescent molecular probe.

[0030] The proton nuclear magnetic spectrum data of above-mentioned gained probe: 1 H NMR (500 MHz, DMSO- d 6 ) δ 8.89 (s, 2H),8.62-8.65 (d, J = 16.4 Hz, 3H), 8.54 – 8.46 (m, 5H), 8.32-8.34 (d, J = 9.0Hz, 1H), 8.24-8.25 (d, J = 8.2 Hz, 1H), 8.16-8.18 (d, J = 8.9 Hz, 1H), 7.87 –7.60(m, 8H), 4.90-4.95 (q, J = 7.3 Hz, 2H), 2.09 (s, 6H), 1.58 (t, J = 7.3Hz, 3H).

Embodiment 3

[0031]Example 3: Application of fluorescence-enhanced fluorescent molecular probes for rapid detection of bisulfite ions or sulfite ions.

[0032] Dissolve the molecular fluorescent probe in dimethyl sulfoxide (DMSO) to make a 1 mmol / L probe solution; add the corresponding ethanol and PBS (pH=7.4) buffer to the probe solution to make a 10 µM (organic phase: PBS aqueous phase = 4:6, v / v) solution, test its ultraviolet absorption spectrum and fluorescence emission spectrum changes. In the ultraviolet absorption spectrum and fluorescence emission spectrum, the probe has high selectivity to bisulfite ion or sulfite ion. With the increase of the concentration of bisulfite ion or sulfite ion, its ultraviolet absorption The spectrum changes obviously, the absorption peak at the wavelength of 493 nm gradually decreases, and the absorption peak at the wavelength of 319 nm gradually increases, and the obvious color change from red to colorless is also suitable for naked eye detection, a...

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Abstract

The invention discloses synthesis and application of a fluorescence-enhanced fluorescent molecular probe for rapidly detecting hydrogen sulfite ions or sulfite ions. The structural formula of the fluorescent molecular probe is shown as FORMULA (1). The fluorescent molecular probe for rapidly detecting the hydrogen sulfite ions or the sulfite ions, provided by the invention, has the advantages of high response (15 s), low detection limit (48 nM), high selectivity, high sensitivity, suitability for naked eye detection, wide pH application range and the like, and can be applied to detection of the hydrogen sulfite ions or the sulfite ions in living cells; the fluorescent molecular probe is not interfered by negative ions such as AcO-, CO32-, F-, Cl-, Br-, HCO3-, NO3-, S2O32-, HS-, SO42-, HPO42-, H2PO4-, PO43-, SCN- and the like; even in the presence of interfering ions, the fluorescent molecular probe also has good response to the hydrogen sulfite ions or the sulfite ions and has the detection limit as low as 48 nM, so that the fluorescent molecular probe is a very sensitive detection system; the fluorescent molecular probe can be applied to analysis and imaging of the living cells, so that the fluorescent molecular probe has a potential practical application value in the fields of biochemistry, environmental science and the like.

Description

technical field [0001] The invention belongs to the technical field of biochemistry, and in particular relates to the synthesis and application of a fluorescence-enhanced fluorescent molecular probe for rapidly detecting bisulfite ions or sulfite ions. Background technique [0002] The use of fluorescent probes as an excellent detection technique has attracted increasing attention due to their high selectivity and sensitivity and real-time imaging, and the advantages of simple operation, high sensitivity, non-toxicity and visualization, fluorescent molecules Probes have emerged as powerful tools for visualizing anions in living systems and have been widely used in analytical detection in recent years. [0003] Sulfites have been widely used in food and beverage processing as preservatives because of their ability to inhibit microbial growth and prevent discoloration. However, excess sulfites can induce conditions such as diarrhea, hypotension, allergic reactions, and asthma...

Claims

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Application Information

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IPC IPC(8): C07D403/10C09K11/06G01N21/64
CPCC07D403/10C09K11/06C09K2211/1029C09K2211/1044G01N21/643
Inventor 尹鹏喻婷尹国兴李海涛张友玉
Owner HUNAN NORMAL UNIVERSITY
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