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Diethylstibestrol hapten and complete antigen and preparation method thereof

A complete antigen and hapten technology, which is applied in the field of immunochemistry and detection, can solve the problems of low product purity, uncontrollable reaction, and long reaction time, and achieve the effects of high product purity, saving reaction substrates, and short synthesis time

Active Publication Date: 2018-02-16
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, because DES, HEX, and DIS contain two phenolic hydroxyl groups, during the activation reaction, both phenolic hydroxyl groups may be activated. Adopt the weaker catalyzer of activity, as potassium carbonate, sodium carbonate or triethylamine etc., but its reaction often needs heating, and the reaction time is longer; And use strong catalyzer to exist again (two phenolic hydroxyl groups are all activated) product purity is not good High, uncontrollable response and other issues

Method used

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  • Diethylstibestrol hapten and complete antigen and preparation method thereof

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Embodiment approach

[0018] The estrogen hapten is an estrogen derivative, and the hapten is the introduction of a carboxyl group on the phenolic hydroxyl side of estrol to form an estrol-monocarboxymethyl ether compound.

[0019] Specifically, the structural formulas of the estrogen haptens prepared in the examples of the present invention are shown in Formula I, Formula II, and Formula III:

[0020]

[0021] As described in the background art, the existing synthesis of estrogen haptens has many shortcomings. The present invention redesigns and optimizes the hapten synthesis process, and finally obtains an efficient synthesis method of high-purity estrogen haptens.

[0022] In a specific embodiment, the present invention discloses a method for preparing estrogen haptens, the method comprising: carrying out estrogen and monochloroacetate in an organic solvent at room temperature and the presence of a catalyst The reaction is terminated by ice water, the organic extractant extracts unreacted estrogens, th...

Embodiment 1

[0036] Example 1: Preparation method of diethylstilbestrol hapten

[0037] Weigh 295 mg of diethylstilbestrol into 6 mL of dry dimethyl sulfoxide, add 1.540 g of potassium hydroxide to the solution, and stir for 5 min. Add 64 mg of sodium monochloroacetate. At room temperature 10°C, after 35 minutes of magnetic stirring, 50 mL of ice water was added to terminate the reaction. Add 24 mL of ethyl acetate and extract three times to remove unreacted diethylstilbestrol. Under stirring, the aqueous phase was acidified with 100 mL 1.5mol / L hydrochloric acid, and a white precipitate appeared. Filter through a funnel, wash the precipitate with distilled water to neutrality, and place it in an oven to dry to obtain the diethylstilbestrol hapten with a yield of about 28% and a purity of about 98%.

Embodiment 2

[0038] Example 2: Preparation method of diethylstilbestrol hapten

[0039] Weigh 293 mg of diethylstilbestrol into 4 mL of dry dioxane, add 0.924 g of potassium hydroxide to the solution, and stir for 5 min. Add 128 mg of sodium monochloroacetate. At room temperature 10°C, after 35 minutes of magnetic stirring, 50 mL of ice water was added to terminate the reaction. Add 24 mL of ethyl acetate and extract twice to remove unreacted diethylstilbestrol. The aqueous phase was acidified with 100mL 2.5mol / L nitric acid while stirring, and a white precipitate appeared. Filter through a funnel, wash the precipitate with distilled water until it is neutral, put it in an oven to dry, and obtain the diethylstilbestrol hapten with a yield of about 29% and a purity of about 97%.

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Abstract

The invention discloses diethylstibestrol hapten and complete antigen and a preparation method thereof. The preparation method comprises the following steps: under conditions of normal temperature andpresence of a catalyst, performing reaction on diethylstilbestrol and monochloroacetate in an organic solvent, terminating the reaction with icy water, treating unreacted diethylstilbestrol with an organic extraction agent, and acidizing a water phase with an acid, so as to obtain white precipitate, namely diethylstibestrol hapten. By adopting the preparation method, the catalyst, the reaction time and the like in synthesis are optimized, a simple and convenient method without heating or pH value control is provided, and hapten can be prepared within a short time; by the virtue of different dissolution properties of a product and a substrate, unreacted diethylstilbestrol substances are removed by using an extraction method, the obtained diethylstilbestrol substances are recycled and continuously used, and the reaction substrate is saved; finally the diethylstilbestrol hapten of high purity is prepared by using a hydrochloric acid acidification crystallization method; complete antigenis prepared from the diethylstibestrol hapten and a carrier protein through connection.

Description

Technical field [0001] The present invention relates to the field of immunochemistry and detection technology, in particular to an estradiol hapten, a complete antigen and a preparation method thereof, in particular to diethylstilbestrol (DES), hexestrol (HEX) and diethylstilbestrol (DIS) Preparation method of hapten. Background technique [0002] Environmental estrogen refers to a class of compounds that have estrogenic effects, can imitate natural estrogen, and interfere with endocrine function. Diethylstilbestrol (DES), Hexestrol (HEX) and Diethylstilbestrol (DIS) are non-steroidal anabolic hormones, which can promote the increase of nitrogen retention in animals, increase protein deposition and reduce fat deposition, because of their simple structure , Easy to synthesize, low cost, etc., and is used to promote the growth of livestock and poultry, increase lean meat rate and so on. Because DES, HEX, DIS, etc. are all environmental estrogens, they can interfere with or block ...

Claims

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Application Information

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IPC IPC(8): C07C51/367C07C59/70C07K14/765C07K14/77C07K14/795G01N33/74G01N33/535
CPCC07C51/367C07C59/70C07K14/765C07K14/77C07K14/795G01N33/535G01N33/74
Inventor 贾敏
Owner SHANDONG NORMAL UNIV
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