A kind of carbazole fluorescent thymine drug labeling reagent, synthesis and application

A technology of thymine and labeling reagents, applied in luminescent materials, instruments, organic chemistry, etc., can solve the problems that have not yet been reported on chemical fluorescence derivatization-high performance liquid chromatography fluorescence analysis, poor retention behavior of reversed-phase chromatography, and lack of fluorescence luminescence properties and other issues, to achieve broad application prospects, improve retention behavior, and the effect of simple synthesis steps

Active Publication Date: 2021-06-18
QUFU NORMAL UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This type of drug does not have fluorescence properties, and the detection method based on the mass spectrometry detection platform has more interference, but the polarity of this type of drug is relatively large, the retention behavior of reversed-phase chromatography is poor, and the matrix interference is relatively strong, so it is necessary to improve the detection of this type of drug Sensitivity, improving its retention behavior in reversed-phase chromatographic analysis. Through chemical derivatization technology, introducing fluorophores and hydrophobic structures is an effective way to achieve fluorescence detection of this type of drug and improve its retention behavior in reversed-phase chromatography
However, there is no report on the use of chemiluminescent derivatization-high performance liquid chromatography fluorescence analysis in the detection of this type of drug

Method used

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  • A kind of carbazole fluorescent thymine drug labeling reagent, synthesis and application
  • A kind of carbazole fluorescent thymine drug labeling reagent, synthesis and application
  • A kind of carbazole fluorescent thymine drug labeling reagent, synthesis and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] 1. Preparation of (4-(9H-carbazol-9-yl)phenyl)methanol

[0035] Add 10g of carbazole, 13.3g of 4-bromobenzyl alcohol, 5g of potassium carbonate, 2.5g of cuprous iodide and 3mL of di-tert-valerylmethane into a 250mL three-necked flask, add 150mL of dimethyl sulfoxide as a solvent, and react overnight in an oil bath at 130°C; After the reaction was finished, the reaction solution was cooled to room temperature, suction filtered, then the suction filtrate was mixed with 15wt% NaCl aqueous solution to separate out solids, the solids were reclaimed and dried, and recrystallized 3 times with acetonitrile to obtain the intermediate (4-(9H-carbazole -9-yl)phenyl)methanol, the yield was 82%.

[0036] 2. Preparation of target product 4-(9H-carbazol-9-yl)benzyl chloride

[0037] Add 7.5g (4-(9H-carbazol-9-yl)phenyl)methanol to a 100ml single-necked round bottom flask equipped with electromagnetic stirring, dissolve completely with 20mL dichloromethane, add a small amount of triet...

Embodiment 2

[0042]Realize the fluorescent labeling and detection of thymine drugs. In addition to ensuring that the "C=S" bond in the thymine drug molecule is completely isomerized to "C-SH", the maximum excitation and maximum Emission wavelength is the key to improve detection sensitivity. Utilizing the property of isomerization of the "C=S" bond in the molecule to "C-SH" under the alkaline condition of pH=8.0 in thymine drugs, it can ensure the "C=S" in the thymine drug molecules The bond is completely isomerized to "C-SH". In order to obtain the maximum excitation and emission wavelengths for detection, 2-thiouracil standard solution was labeled with 4-(9H-carbazol-9-yl)benzyl chloride solution at a concentration of 1 μM, and then HPLC-fluorescence analysis was performed , the maximum excitation wavelength of the labeled product is 365nm, and the maximum emission wavelength is 400nm. At the same time, the 4-(9H-carbazol-9-yl)benzyl chloride-labeled product of 2-thiouracil was subject...

Embodiment 3

[0044] (1) Use 4-(9H-carbazol-9-yl) benzyl chloride fluorescent label to detect the content of thymines in milk, prepare a buffer solution of disodium hydrogen phosphate / sodium dihydrogen phosphate with pH=8.0, and use it to prepare 5 The solution of part thymine drug standard substance, concentration is respectively 1 μ M, 10 μ M, 100 μ M, 1 mM, 10 mM; Preparation concentration is the acetonitrile solution of the 4-(9H-carbazol-9-yl) benzyl chloride of 100 mM;

[0045] (2) Add 100 μL thymine standard drug solution and 50 μL acetonitrile solution of 4-(9H-carbazol-9-yl)benzyl chloride to a 2 mL ampoule in sequence, and react in a water bath at 40°C for 15 min After the reaction is completed, add 100 μL of dilute hydrochloric acid (0.1mol / L), take 10 μL for HPLC-fluorescence analysis, take the concentration of thymine drugs as the abscissa, and use the peak area as the ordinate to draw the concentration working curve of thymine drugs ;

[0046] (3) Add acetonitrile to the milk...

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Abstract

The present invention relates to carbazole fluorescent thymine drug labeling reagent, synthesis and application. Carbazole is used as fluorescent mother ring, benzyl chloride is used as reactive group, and its chemical name is: 4-(9H-carbazole-9- base) benzyl chloride. The novel stable carbazole-based fluorescent thymine drug labeling reagent described in the present invention can accurately, sensitively and rapidly label thymine drugs under mild conditions, thereby realizing the separation of micro and trace amounts of thymine drugs in complex systems It can be used in research fields such as environmental analysis and food safety, and has broad application prospects.

Description

technical field [0001] The invention belongs to the technical field of fluorescent labeling of organic small-molecule thymine drugs, and in particular relates to a novel stable carbazole fluorescent thymine drug labeling reagent as well as its synthesis method and application. Background technique [0002] Thymines are a series of thiourea derivatives with different substituents. These drugs can reduce the production of thyroid hormones, inhibit normal metabolism, reduce gastrointestinal motility, increase the water retention capacity of subcutaneous and muscle tissue and gastrointestinal tract, and increase the weight of animals. They are widely used in animal breeding. Therefore food quality becomes poor, and the food that contains this type of drug residue also causes potential harm to human health. Rapid and accurate determination of thymine drug residues is of great significance for environmental chemistry and food safety. This type of drug does not have fluorescence ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/86C09K11/06G01N30/02G01N30/74
CPCC07D209/86C09K11/06C09K2211/1007C09K2211/1029G01N30/02G01N30/74
Inventor 尤进茂于延新宋翠华孙志伟纪仲胤庄建林罗贤柱王旭
Owner QUFU NORMAL UNIV
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