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Application of near infrared-emission fluorescent probe in quick pesticide residue detection

A technology for fluorescent probes and pesticide residues, applied in fluorescence/phosphorescence, measurement devices, material excitation analysis, etc., can solve the problems of being easily affected by biomass fluorescence, short fluorescence wavelength, etc., and achieve a simple and easy synthesis process and fast metabolism. , responsive effect

Active Publication Date: 2018-07-24
王铮
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Recently, Chemical Communications (2017, 53, 3952-3955) reported a case of fluorescein-based fluorescent probes, which can directly detect the activity of AChE enzymes, but have short fluorescence wavelengths and are easily affected by biomass fluorescence.

Method used

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  • Application of near infrared-emission fluorescent probe in quick pesticide residue detection
  • Application of near infrared-emission fluorescent probe in quick pesticide residue detection
  • Application of near infrared-emission fluorescent probe in quick pesticide residue detection

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] The chemical synthesis of embodiment 1 compound 2-(4-(diethylamino)-2-hydroxybenzoyl) benzoic acid DHBA

[0026] (1) Dissolve 22mmol 3-hydroxy-N,N-diethylaniline (DAHO) and 20mmol phthalic anhydride in 100mL toluene solution, N 2 Protection, heated to reflux for 15h.

[0027] (2) The solvent of the reaction solution was distilled off under reduced pressure, and the solid mixture was separated by column chromatography (developing solvent: dichloromethane:methanol=20:1, v:v).

[0028] (3) Add 10% NaOH solution to the separated solution for washing, and ultrasonically so that the product is fully dissolved in the water phase. Let the mixture stand and take the aqueous phase. 20% HCl was added to the water phase to adjust the pH of the system to 4-5, a large amount of white solids were precipitated, and finally about 2.8 g of the white solid compound DNBA was obtained. 1 H NMR (500MHz, DMSO) δ13.06(s,1H),12.57(s,1H),8.00–7.93(m,1H),7.69(td,J=7.5,1.1Hz,1H),7.61(td, J=7.7...

Embodiment 2

[0029] Example 2 Chemical synthesis of 10-(diethylamino)-3-hydroxyl-3'H-spiro[benzo[c]xanthene-7,1'-isobenzofuran]-3'-one NDRO

[0030] (1) Dissolve 8 mmol of DHBA and 8.5 mmol of 1,6-dihydroxynaphthalene in 30 mL of trifluoroacetic acid (TFA). Stir and reflux, and control the reaction temperature to 90°C.

[0031] (2) Stir the reaction for 12h, stop the reaction, and the solution returns to room temperature;

[0032] (3) The solvent trifluoroacetic acid was rotary evaporated to dryness. The reaction mixture was separated by column chromatography (developing solvent: dichloromethane:methanol=15:1, v:v) to finally obtain 1.4 g of red solid compound NDRO. 1 H NMR (500MHz,DMSO)δ10.50(s,1H),8.60(s,1H),8.13(s,1H),7.92–7.71(m,2H),7.50(s,1H),7.35(dd, J = 18.2, 7.1 Hz, 2H), 7.23 (s, 1H), 6.76 (s, 4H), 3.54 (s, 4H), 1.19 (s, 6H).

Embodiment 3

[0033] Example 3 10-(Diethylamino)-3'-oxo-3'H-spiro[benzo[c]xanthene-7,1'-isobenzofuran]-3-yl acetate Chemical Synthesis of NDRO-1

[0034] (1) Dissolve 120mg of the intermediate product NDRO in 26mL of dichloromethane, add about 70mg of acetyl chloride, then dropwise add 4-5 drops of triethylamine, and stir at room temperature for 25min;

[0035] (2) Add 35 mg of acetyl chloride, continue stirring for 40 min, and add water to quench the reaction.

[0036] (3) The organic layer was washed with water for 3 times, and then the dichloromethane was rotary evaporated to dryness. The reaction mixture was separated by column chromatography (developing solvent: dichloromethane:methanol=80:1, v:v) to obtain NDRO-153 mg as a red solid compound. 1 H NMR (500MHz, CDCl3) δ8.63 (d, J = 8.9Hz, 1H), 8.05 (d, J = 7.3Hz, 1H), 7.62 (dd, J = 16.5, 7.7Hz, 2H), 7.53 (s ,1H),7.38(d,J=8.6Hz,2H),7.15(d,J=7.2Hz,1H),6.78(d,J=8.7Hz,1H),6.66(s,2H),6.45(s , 1H), 3.41 (d, J = 6.4Hz, 4H), 2.37 (s, 3H), 1...

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Abstract

The invention discloses application of a near infrared-emission fluorescent probe in quick pesticide residue detection and belongs to the technical field of quick pesticide detection. The probe is based on rhoda-fluor fluorescence matrix and has specific activity on acetylcholine esterase AChE; by means of an enzyme inhibition detection principle, the probe can be applied to quick detection of organophosphorus pesticide and carbamate pesticide residues in food. The acetylcholine esterase AChE is extracted from duck blood; in an appropriate probe substrate range, enzyme activity and an inhibition rate can be represented by quantitatively detecting fluorescence intensity change of the probe. Four pesticide detection standard curves have small error, and R<2> is larger than 0.98; vegetable pesticide adding standard recovery most reaches 80 to 110%, so that the near infrared-emission fluorescent probe disclosed by the invention can be applied to quantitative, ppb-grade and quick detectionof organophosphorus and carbamate pesticide residues in the food.

Description

technical field [0001] The invention belongs to the field of rapid detection of pesticide residues, and in particular relates to a fluorescent bottom probe substrate of AChE enzyme and an application thereof. Background technique [0002] Organophosphorus and carbamate pesticides are two major categories of pesticides currently used in my country. Pesticide residues will have a very serious impact on the environment and organisms, so the detection technology of pesticide residues is very important. At present, pesticide detection technologies are mainly divided into traditional detection and rapid detection. Traditional detection mainly involves gas chromatography, liquid chromatography and its combination with mass spectrometry. The detection cost is high and time-consuming, which is not conducive to large-scale deployment. The rapid detection technology is mainly based on the ultraviolet-visible absorption method, which has problems such as low sensitivity and high detec...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): G01N21/64
CPCG01N21/6402G01N21/6486
Inventor 王铮崔京南冯磊张淑芳高漫田镇豪刘涛何鑫张晓静赵鑫
Owner 王铮
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