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Preparation method of 1,8-naphthalimide derivative fluorescent probe and method for detecting casein by using biological probe

A technology of fluorescent probe and naphthalimide, which is applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of expensive detection instruments, complicated operation process, poor sensitivity and selectivity, etc., and achieve a good choice performance, high sensitivity, and improved sensitivity

Inactive Publication Date: 2014-06-11
HUBEI UNIV OF ARTS & SCI
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  • Abstract
  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

However, these methods have limitations to varying degrees, such as poor sensitivity and selectivity, expensive detection instruments, and complicated operating procedures.

Method used

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  • Preparation method of 1,8-naphthalimide derivative fluorescent probe and method for detecting casein by using biological probe
  • Preparation method of 1,8-naphthalimide derivative fluorescent probe and method for detecting casein by using biological probe
  • Preparation method of 1,8-naphthalimide derivative fluorescent probe and method for detecting casein by using biological probe

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Add 2.77g, 10.0mmol / L 4-bromo-1,8 naphthalene anhydride and 100mL ethylenediamine into a round bottom flask, heat and stir at 60°C for 6 hours, then cool, and vacuum dry to remove ethylenediamine to obtain an intermediate product. Dissolve the intermediate product and 11.9mL, 140mmol / L methyl chloroacetate in 15mL acetonitrile, add NaH 2 PO 4 , 0.5g each of KI, heated and stirred at 40°C for 3 days, the solution was clear, added 0.25mL, 3mol / L NaOH was added and continued to stir for 12 hours, after cooling, the pH value of the system was adjusted to 2-3 with 1M HCl, anhydrous Ethanol recrystallized twice to obtain a yellow solid probe.

[0026] Yield: (79%).IR(cm -1 ):3376(vNH);2830(νCH);1732(νC=O);1693(ν as Naphthalimide N-C=O); 1656(ν a Naphthalimide N-C=O). 1 H NMR (400MHz, CDCl 3 )δ:8.03-7.92(d,J=8.4Hz,3H),7.56(t,J=7.8Hz,1H),6.66(d,J=7.1Hz,1H),5.83(t,J=7.3Hz, 1H),4.9(m,1H),4.05(s,4H),3.75-3.86(t,J=9.2Hz,4H),3.17(s,8H),2.66-2.70(t,J=8.0Hz,4H ).Elemental Anal...

Embodiment 2

[0028] Add 2.77g, 10.0mmol / L 4-bromo-1,8 naphthalene anhydride and 100mL ethylenediamine into a round bottom flask, heat and stir at 70°C for 4 hours, then cool, and vacuum dry to remove ethylenediamine to obtain an intermediate product. Dissolve the intermediate product and 11.9mL, 140mmol / L methyl chloroacetate in 15mL methanol, add NaH 2 PO 4 , 0.5 g each of KI, heated and stirred at 45°C for 2 days, and the solution was clarified. Add 0.25 mL, add 3mol / L NaOH and continue to stir for 10 hours. After cooling, adjust the pH value of the system to 2 with 1M HCl. Crystallization three times gave a yellow solid probe.

[0029] Yield: (79%).IR(cm -1 ):3376(vNH);2830(νCH);1732(νC=O);1693(ν as Naphthalimide N-C=O); 1656(ν a Naphthalimide N-C=O). 1 H NMR (400MHz, CDCl 3 )δ:8.03-7.92(d,J=8.4Hz,3H),7.56(t,J=7.8Hz,1H),6.66(d,J=7.1Hz,1H),5.83(t,J=7.3Hz, 1H),4.9(m,1H),4.05(s,4H),3.75-3.86(t,J=9.2Hz,4H),3.17(s,8H),2.66-2.70(t,J=8.0Hz,4H ).Elemental Analysis: Calculation: C 24 h ...

Embodiment 3

[0031] Dissolve 500 mg of casein in 100 mL of PBS (pH 7.4) buffer solution to obtain a 5 mg / mL casein solution, and dissolve 0.5 μmol of fluorescent probe in 100 mL of PBS (pH 7.4) buffer solution to obtain a 5 μmol / L fluorescence probe Probe solution.

[0032] Dissolve 500 mg of casein in 50 mL of PBS (pH 7.4) buffer solution to prepare a 10 mg / mL casein solution, add 4 drops of 0.1 mol / L NaOH solution and sonicate for 1 min until the solid dissolves, then add 0.1 M HCl to adjust the pH to 7.4. Dissolve 0.5 μmol fluorescent probe mol / L in 100 mL PBS (pH 7.4) buffer solution to prepare 5 μmol / L fluorescent probe mol / L solution.

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Abstract

The invention discloses a preparation method of a 1,8-naphthalimide derivative fluorescent probe and a method for detecting casein by using the biological probe. A method for detecting casein based on aggregation-induced emission is established by using the characteristic of casein micelles. The detection of casein based on aggregation-induced synchronous emission has the technical effects that 1, the aggregation-induced emission phenomenon of a 1,8-naphthalimideprobe on casein micelles is brought up for the first time, and a casein detection technology is established; 2, a high-performance aggregation-induced emission probe is designed on the basis of a novel thought for providing aggregation emission efficiency by taking double carboxyl as a precursor embedded group and aggregating fluorescent elements on the surface of casein; 3, high selectivity to the detection of exogenous illegal additives is realized; 4, the casein aggregation-induced synchronous emission has the characteristics of high sensitivity, easiness, convenience, rapidness and accuracy, and the sensitivity can be raised by three orders of magnitudes compared with those of the conventional biuret method and colorimetric ELISA (Enzyme Linked Immunosorbent Assay) method.

Description

technical field [0001] The invention relates to the field of detection of luminescent materials, in particular to a method for preparing a fluorescent probe of 1,8-naphthalimide derivatives and a method for detecting casein by using the biological probe, which is used to detect the content of true protein in dairy products . Background technique [0002] Casein is the most important protein in the true milk protein, accounting for about 80% of the total protein content, and mainly exists in milk in the form of micelles. Due to the flaws in the dairy protein detection method in China’s national standards, illegal operations such as adding organic substances with high nitrogen content such as urea, ammonium fertilizer, and melamine to increase the “protein content” have occurred, which has seriously restricted the quality improvement of dairy products in my country and affected consumption. the health of the patient. Although on October 20, 2008, the Ministry of Agriculture i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/14C09K11/06G01N21/64
CPCC07D221/14C09K11/06C09K2211/1029G01N21/6428
Inventor 孙洋杨晓慧韩权李岩翟云会李靖焦宝娟
Owner HUBEI UNIV OF ARTS & SCI
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