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Acridinium ester derivative, synthesis method and application thereof

A technology of derivatives and acridinium esters, applied in the field of chemiluminescent acridinium ester derivatives and their synthesis, to achieve the effects of constant intensity, long luminescence duration and high sensitivity

Inactive Publication Date: 2015-07-08
BEIJING LEADMAN BIOCHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, in the chemiluminescence immunoassay reagent system using alkaline phosphatase (ALP) as the labeled enzyme, there is still a lack of a chemiluminescence immunoassay tracer with high sensitivity, long luminescence duration, easy to use, and constant intensity at room temperature. thing

Method used

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  • Acridinium ester derivative, synthesis method and application thereof
  • Acridinium ester derivative, synthesis method and application thereof
  • Acridinium ester derivative, synthesis method and application thereof

Examples

Experimental program
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Embodiment 1

[0038] Example 1 Synthesis of 9-[(p-trifluoromethylphenylthio)-phosphoryloxymethylene]-10-methyl-9,10-dihydroacridine, disodium salt

[0039] 1. Synthesis of acridine-9-thiocarboxylic acid p-trifluoromethylphenyl ester

[0040] In a 250ml three-necked reaction flask, add 80ml of DCM (dichloromethane) as a solvent, add 1.78g of p-trifluoromethylthiophenol and 2.40g of acridinium-9-acid chloride, and add 2ml of triethylamine under stirring , and soon the reaction mixture turned orange, heated to reflux, stirred and reacted for about 2 hours. After the reaction was complete, the solvent was removed, and the obtained solid was washed with 5% aqueous sodium bicarbonate and deionized water, filtered, and the filter cake was dried to obtain 3.0 g of a brownish-yellow solid product with a yield of 78.3%.

[0041] 1 H NMR (CDCl 3 ) δ7.47~7.50(m, 2H), 7.60~7.65(m, 4H), 7.82~7.85(m, 2H), 8.12(d, 2H), 8.30(d, 2H).

[0042] 2. Synthesis of 10-methyl-acridine-9-thiocarboxylic acid p-tri...

experiment example 1

[0051] Experimental example 1 9-[(p-trifluoromethylphenylthio)-phosphoroxymethylene]-10-methyl-9,10-dihydroacridine, application experiment of disodium salt

[0052] 1. 9-[(p-trifluoromethylphenylthio)-phosphoryloxymethylene]-10-methyl-9,10-dihydroacridine, the chemiluminescent substrate working solution of disodium salt prepare

[0053] experiment material:

[0054]

[0055] Preparation method:

[0056] Add 700ml of deionized water into the light-proof container, add 24.0g of TRIS, 0.03g of cetyltrimethylammonium chloride, 9.0g of sodium chloride, and 5.0mg of lucigenin in sequence. Hydrochloric acid to adjust the pH to 9.35±0.1. Add 9-[(p-trifluoromethylphenylthio)-phosphoryloxymethylene]-10-methyl-9,10-dihydroacridine, 0.2g of disodium salt, stir to dissolve and use deionized Make up to 1 liter of water. Verify that the pH is within the range of 9.35±0.1, filter through a 0.22 micron pore size filter, and store at 2-8°C.

[0057] 2. Performance detection of lumines...

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Abstract

The invention discloses an acridinium ester derivative, a synthesis method and application thereof. The chemiluminescent acridinium ester derivative provided by the invention has a structural formula shown as formula I. The invention further discloses a synthesis method for the compound shown as formula I, and the method includes: (1) synthesizing acridine-9-thiocarboxylic acid p-trifluoromethylbenzene ester; (2) synthesizing 10-methyl-acridine-9-thiocarboxylic acid p-trifluoromethylbenzene ester; (3) synthesizing 10-methyl-9, 10-dihydroacridine-9-thiocarboxylic acid p-trifluoromethylbenzene ester; and (4) synthesizing TfS-APS. The acridinium ester derivative provided by the invention can be used as an immunoassay tracer to a chemiluminescence immunoassay reagent system with alkaline phosphatase (ALP) as the marker enzyme. The application effect in a kit proves that the acridinium ester derivative involved in the invention can detect 1*10<-19>mol ALP molecules, and has the advantages of high sensitivity, long luminescence duration, simple use, constant intensity under room temperature condition, and no need for precise temperature control, etc.

Description

technical field [0001] The present invention relates to acridinium ester derivatives, in particular to a chemiluminescent acridinium ester derivative and a synthesis method thereof. The present invention also relates to the application of the acridinium ester derivative as a chemiluminescent substance in immunoassay, which belongs to the chemiluminescent substrate The field of acridinium ester derivatives. Background technique [0002] Chemiluminescence Immunoassay (CLIA) is a new type of labeled immunoassay technology that combines chemiluminescence or bioluminescence system with immune reaction to detect trace antigen or antibody. The principle of detecting the immune reaction is the same as that of radioimmunoassay (RIA) and enzyme immunoassay (EIA). The difference is that luminescent substances are used instead of chromogenic substances, etc., and the relative luminous intensity (RLU) is detected by the sample, and the content of the analyte is deduced quantitatively or ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/64C09K11/06G01N33/535
Inventor 叶建峰
Owner BEIJING LEADMAN BIOCHEM
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