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Compound, preparation and application thereof in detecting divalent copper ions and pH of strong acid

A compound, ethylenediamine technology, applied in chemical instruments and methods, organic chemistry, measuring devices, etc.

Active Publication Date: 2019-10-22
SHANXI DATONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it was found that it has good fluorescence properties (such as high quantum yield, long wavelength and stable properties), and can detect Cu in real time. 2+ Fluorescence sensors for pH and strong acid still face certain challenges

Method used

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  • Compound, preparation and application thereof in detecting divalent copper ions and pH of strong acid
  • Compound, preparation and application thereof in detecting divalent copper ions and pH of strong acid
  • Compound, preparation and application thereof in detecting divalent copper ions and pH of strong acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070] Example 1: Preparation of fluorescent sensor RCy7

[0071] Step 1: Synthesis of Compound IV

[0072]

[0073] Dissolve 10 g of 2,3,3-trimethyl-3H-indoline in acetonitrile, add 1.5 equivalents (moles) of 6-bromohexanoic acid dropwise at room temperature, reflux and stir for 20 hours under nitrogen protection, cool, and add diethyl ether Extract, evaporate the solvent, dissolve in a small amount of ethanol, add ether to precipitate, filter, and dry in vacuo. Compound IV (1-(5-carboxypentyl)-2,3,3-trimethyl-3H-indole) was obtained as a white solid.

[0074] Step 2: Synthesis of Compound III

[0075]

[0076] Take 1g of condensing agent 2-chloro-1-formyl-3-hydroxymethylcyclohexene, 2.5 equivalents (moles) of compound IV, 50mL of n-butanol, and 5mL of toluene into a flask equipped with a water separator. The mixture was stirred under reflux for 15 hours under the protection of nitrogen to obtain a dark green solution, and the solvent was evaporated by rotary evaporati...

Embodiment 2

[0091] Embodiment 2: The influence of the concentration of divalent copper ions on the ultraviolet-visible absorption spectrum of sensor RCy7 of the present invention

[0092] At a concentration of 10 μmol / Lol / L sensor RCy7 in acetonitrile / Tris-HCl (v / v, 1:1, pH=7.2) buffer solution, add 0,0.1,0.3,0.5,0.7,1,1.5,2.0, 3.0, 5.0, 5.0, 7.0, 10, 13, 15, 18, 20, 25, 30 times the equivalent concentration of divalent copper ion solution and measure the ultraviolet-visible absorption spectrum of the system, the results show that the maximum absorption value of the sensor RCy7 is at 633nm About, after adding divalent copper ions, the absorption at 633nm decreases significantly, and at the same time the absorption peak at 511nm continues to increase, but when the concentration of divalent copper ions is greater than 2 equivalents, the absorption peak at 511nm begins to decrease gradually . See attached Figure 7 .

Embodiment 3

[0093] Embodiment 3: The fluorescent sensor RCy7 of the present invention can be used to detect divalent copper ions, and the specific application method is as follows:

[0094] Determination of divalent copper ion content: First, mix acetonitrile and Tris-HCl (pH=7.2) buffer evenly according to the volume ratio of 1:1, then add the sensor RCy7 of the present invention to make the concentration 10 μmol / L to make a standard solvent, Then use the prepared standard solvent to prepare divalent copper ion concentrations of 0, 1, 3, 5, 7, 10, 12, 13, 14, 15, 20, 30, 35, 40, 45, 50, 70, 100, 130, 150, 180, 200, 250, 300 μmol The copper ion standard solution of / L adopts HITACHI F2500 fluorescence spectrophotometer, and at excitation wavelength is 550nm, the emission wavelength when measuring different copper ion concentrations respectively is fluorescence intensity when 577nm and 722nm, fluorescence intensity ratio (F 577 / F 722 ) and the concentration of copper ions to make a stand...

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Abstract

The invention relates to a fluorescent sensor in the field of fine chemical industry, a preparation method and application thereof, and in particular relates to a bifunctional identification sensor based on a rhodamine dye and a long-wavelength Cy7 cyanine dye and a preparation method thereof, and application thereof in near infrared ratio detection of divalent copper ions and pH and fluorescencemicroscopic imaging detection of divalent copper ions in cells. The copper ion fluorescence sensor based on ethylenediamine bridging rhodamine B and the Cy7 cyanine dye has the following remarkable characteristics: (1) in an acetonitrile / Tris-HCl (V / V, 1: 1, pH = 7.2) buffer solution, near infrared ratio detection can be performed on the divalent copper ions; (2) the copper ion fluorescence sensorhas good selectivity and almost no response to other metal ions; (3) detecting of the divalent copper ions is not sensitive to pH; (4) the pH value of a strong acid system can be detected by a near infrared ratio amnner; and (5) the selectivity of pH detection is good.

Description

technical field [0001] The present invention relates to a class of fluorescent sensors in the field of fine chemicals, and their preparation methods and uses, in particular to a class of dual-function recognition sensors based on rhodamine dyes and long-wavelength Cy7 Qing dyes and their preparation methods, which can detect divalent copper ions by near-infrared ratios. And strong acid pH and the application of fluorescence microscopy imaging of divalent copper ions in cells and bacteria under strong acid pH. Background technique [0002] Copper exists in all living organisms and is an important trace element in redox, growth and development processes. The content of copper in cells ranks only after iron and zinc. Copper plays an important role as a catalytic cofactor in different cellular physiological processes, such as mitochondrial respiration, iron uptake, and redox processes of a large number of enzymes, including Cytochrome oxidase, superoxide dismutase, ascorbate ox...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/107C09K11/06G01N21/31G01N21/64
CPCC07D491/107C09K11/06C09K2211/1007C09K2211/1033C09K2211/1088G01N21/314G01N21/6428G01N21/6458G01N2021/6439
Inventor 袁跃华田茂忠白云峰冯锋张振国王艳艳刘玉婕
Owner SHANXI DATONG UNIV
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