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Near-infrared fluorescent probe for rapid detection of ONOO- and preparation method and application of near-infrared fluorescent probe for rapid detection of ONOO-

A fluorescent probe, near-infrared technology, used in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of limited application, short emission wavelength, can not well avoid biological matrix background interference, etc., to achieve economical Environmentally friendly reagents, highly specific effects

Inactive Publication Date: 2019-06-18
SHANXI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Someone synthesized a rapid detection of ONOO - fluorescent probe (CN106905235A), but its emission wavelength is relatively short, which cannot well avoid the background interference of biological matrices, which greatly limits its application in biomedicine

Method used

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  • Near-infrared fluorescent probe for rapid detection of ONOO- and preparation method and application of near-infrared fluorescent probe for rapid detection of ONOO-
  • Near-infrared fluorescent probe for rapid detection of ONOO- and preparation method and application of near-infrared fluorescent probe for rapid detection of ONOO-
  • Near-infrared fluorescent probe for rapid detection of ONOO- and preparation method and application of near-infrared fluorescent probe for rapid detection of ONOO-

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Synthesis and characterization of embodiment 1 fluorescent probe

[0032] (1) Take by weighing 0.32g 6-hydroxyl-1-tetralone and 0.4g 4-(diethylamino) salicylaldehyde and dissolve in the mixed solution of glacial acetic acid and the vitriol oil that the volume ratio is 4:1, ultrasonic A homogeneous mixed solution was obtained, which was then stirred overnight at room temperature. After the reaction was completed, the product was quickly added to ethyl acetate, and the red precipitate was gradually precipitated out, then filtered and washed with ether for 3 times, and the obtained solid was vacuum-dried to obtain the product; 1 H NMR (600MHz, DMSO) δ8.63(s, 1H), 8.16(d, J=8.7Hz, 1H), 7.93(t, J=14.5Hz, 1H), 7.41(dd, J=9.3, 2.4Hz ,1H),7.26(t,J=10.0Hz,1H),6.95(dd,J=8.7,2.4Hz,1H),6.87(d,J=2.3Hz,1H),3.74–3.63(m,4H) ,3.08–2.96(m,4H),1.24(t,J=7.1Hz,6H). 13 C NMR (151MHz, DMSO) δ164.76, 164.32, 158.25, 155.24, 148.39, 146.22, 132.06, 129.43, 120.71, 117.67, 116.18, 96.14, 45.7...

Embodiment 2

[0034] Embodiment 2 fluorescent probe detects ONOO by fluorescence spectroscopy -

[0035] Take 2 μL of the fluorescent probe storage solution in a clean colorimetric tube, dilute it to 2 mL with pH=7.4 phosphate buffer solution, and detect it on a fluorescence photometer. - As the concentration of the solution increases, the fluorescence intensity at 625nm is gradually enhanced on the fluorescence photometer. figure 1 .

Embodiment 3

[0036] Embodiment 3 fluorescent probe measures ONOO by fluorescence spectrometry - linear relationship

[0037] Take 2 μL of the fluorescent probe storage solution in a clean colorimetric tube, dilute it to 2 mL with pH=7.4 phosphate buffer solution, detect it on a fluorescence photometer, and gradually add ONOO - The volume of the solution is 0, 1, 2, 3, 4, 5, 6, 7, 8, and the fluorescence intensity at 625nm is gradually increased on the fluorescence photometer, and the fluorescence intensity of the system at 625nm is the same as that of ONOO - The solution concentration is 0-8×10 -6 The range of M exhibits a good linear relationship to [ONOO - ] is the abscissa, and the fluorescence intensity is used as the ordinate to draw the graph, and [ONOO - ] and the linear equation of fluorescence intensity F=98.26+72.15ONOO - (R 2 =0.9967), see figure 2 .

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Abstract

The invention provides a near-infrared fluorescent probe for rapid detection of peroxynitrite ions (ONOO-) and a preparation method and application of the near-infrared fluorescent probe for rapid detection of ONOO-. The preparation method includes steps: (1) weighing a certain mass of 6-hydroxy-1-tetralone and 4-(diethylamino)salicylaldehyde, dissolving in mixed solution of glacial acetic acid and concentrated sulfuric acid, ultrasonically well mixing, stirring overnight at the room temperature, quickly adding a product into ethyl acetate after reaction is completed, gradually separating outa red precipitate, filtering, washing with diethyl ether for three times, and performing vacuum drying to obtain a solid; (2) adding the obtained solid, potassium carbonate and 4-(bromomethyl)benzeneboronic acid pinacol ester into DMF solution, performing reaction at 60-80 DEG C for 5 hours, adding mixed solution into ice water after reaction is finished, extracting with chloroform, performing spin drying through a rotary evaporator, and carrying out column chromatography separation and purification to obtain a target product. The obtained probe is high in solubility and dispersity in aqueoussolution and can be used for rapid detection of ONOO- and cell imaging.

Description

technical field [0001] The present invention relates to peroxynitrite ion (ONOO - ) preparation method and application, specifically belong to a kind of rapid detection ONOO - preparation methods and applications. Background technique [0002] ONOO - It is a highly active oxidizing agent and efficient nitrating agent, through NO and O 2 ·- generated by the reaction. ONOO - And its secondary products HO.,CO3 ·- and NO 2 - It can react with a variety of biomolecules such as proteins, lipids and nucleic acids, leading to mitochondrial dysfunction and apoptosis. Someone synthesized a rapid detection of ONOO - A fluorescent probe (CN106905235A), but its emission wavelength is relatively short, which cannot well avoid the background interference of the biological matrix, which greatly limits its application in biomedicine. Therefore, it is extremely urgent to synthesize a fluorescent probe with simple operation, good selectivity, high sensitivity, fast detection speed a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07F5/02G01N21/64
Inventor 李明璐宋胜梅梁帆李甘董川双少敏
Owner SHANXI UNIV
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