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Isoluminol derivative and preparation method and application thereof

A technology of isoluminol and derivatives, applied in the field of biological immunology detection, can solve the problems of sensitivity and detection limit, and achieve the effect of reducing impact, improving test sensitivity and detection limit, and ensuring stability

Active Publication Date: 2017-08-08
SHENZHEN NEW INDS BIOMEDICAL ENG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Another object of the present invention is to provide a chemiluminescence base liquid containing the above-mentioned isoluminol derivatives, or a chemiluminescence kit and a chemiluminescence immunoassay system containing the above-mentioned isoluminol derivative-labeled antigens or antibodies, The technical problems of sensitivity and detection limit when using the existing luminol-peroxide system test have been solved

Method used

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  • Isoluminol derivative and preparation method and application thereof
  • Isoluminol derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0169] Preparation of isoluminol derivatives

[0170] 1) Synthesis of ABEI cyclic lactone;

[0171] Take 500mg of ABEI and 200mg of succinic anhydride, dissolve in 30ml of anhydrous DMSO solvent, pass through argon protection, stir in a water bath at 50°C for 30min, transfer to room temperature and avoid light, continue to react for 120min, add 400mg of EDC, stir at room temperature for 24h, and end the reaction . Ethyl acetate was added for extraction, washed with ultrapure water, dried over anhydrous sodium sulfate, spun to dryness, and separated on a silica gel column to obtain ABEI cyclic lactone.

[0172] 2) Preparation of the first intermediate product

[0173] Dissolve 100mg of ABEI cyclic lactone and 34mg of 3-(N,N-diaminopropylamino)propionic acid obtained in step 1) in 5ml of anhydrous DMSO, and react in the dark at 37°C for 4h under the protection of argon, at room temperature Let stand overnight. Add a large amount of ethyl acetate for extraction, wash with dil...

Embodiment 2

[0179] Preparation of isoluminol derivatives

[0180] 1) Synthesis of ABEI cyclic lactone;

[0181] Take 500mg of ABEI and 290mg of adipic anhydride, dissolve in 30ml of anhydrous DMF solvent, pass through argon protection, stir in a water bath at 40°C for 50min, transfer to room temperature to avoid light and continue to react for 3 hours, add 440mg of DCC, stir at room temperature for 24h, end reaction. Ethyl formate was added for extraction, washed with ultrapure water, dried over anhydrous magnesium sulfate, evaporated to dryness, and separated on a silica gel column to obtain ABEI cyclic lactone.

[0182] 2) Preparation of the first intermediate product

[0183] Dissolve 100 mg of ABEI cyclic lactone and 21 mg of 2,4-diaminovaleric acid obtained in step 1) in 5 ml of anhydrous DMF, and react at 37°C in the dark for 3 hours under the protection of argon, and stand at room temperature overnight. Add a large amount of ethyl formate for extraction, wash with dilute hydroch...

Embodiment 3

[0189] Preparation of isoluminol derivatives

[0190] 1) Synthesis of ABEI cyclic lactone;

[0191] Take 500mg of ABEI and 270mg of glutaric anhydride, dissolve in 30ml of anhydrous DMAc solvent, pass through argon protection, stir in a water bath at 60°C for 20min, transfer to room temperature and avoid light, continue to react for 60min, add 450mg of EDC, stir at room temperature for 24h, and end the reaction . Ethyl acetate was added for extraction, washed with ultrapure water, dried over anhydrous sodium sulfate, spun to dryness, and separated on a silica gel column to obtain ABEI cyclic lactone.

[0192] 2) Preparation of the first intermediate product

[0193] Dissolve 100 mg of ABEI cyclic lactone and 25 mg of 3,5-diaminovaleric acid obtained in step 1) in 5 ml of anhydrous DMAc, and react at 37° C. in the dark for 4 h under the protection of argon, and stand at room temperature overnight. Add a large amount of ethyl acetate for extraction, wash with dilute hydrochlo...

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Abstract

The invention discloses an enhanced isoluminol derivative with high luminous intensity and a preparation method thereof, and aims to enhance the luminous intensity of an existing luminol-peroxide system, increase the test sensitivity and detection limit, lower the quantity of antibodies or antigens labelled by a luminescent label, and lower the influence of excessive labelling on the antibody or antigen activity. The invention further discloses a chemiluminescent base solution containing the isoluminol derivative, or a chemiluminescent kit containing the antigens or the antibodies labeled by the isoluminol derivative, and a chemiluminescent immunoassay system, and aims to solve the technical problems of low sensitivity and low detection limit when the existing luminol-peroxide system is used for testing. The invention further provides application of the isoluminol derivate to chemiluminescent immune quantitative analyses.

Description

technical field [0001] The invention relates to the field of biological immunology detection, in particular to an isoluminol derivative and its preparation method and application. Background technique [0002] Luminol, Isoluminol and their derivatives are the first chemiluminescent substances used in chemiluminescence. The chemical name of luminol is 3-aminophthaloylhydrazide, and its luminescent properties were first reported by Albrecht. Such substances produce α-hydroxyperoxide intermediates through oxidation, and the decomposition of the intermediates can release light energy, and the nature of the light is related to the pH value of the reaction system. The oxidation steps of luminol compounds are related to the solvent components. In aprotic solvents, chemiluminescence only needs oxygen and a strong base; in protic solvents, enzymes are needed to catalyze the oxidation of luminol by various oxygen derivatives. . The luminescence efficiency of the luminol system is n...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/14C07D405/14C09K11/06G01N33/533
Inventor 饶微杜凯刘蕾雷斗剑
Owner SHENZHEN NEW INDS BIOMEDICAL ENG
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