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A xanthene polyurethane hapten, artificial antigen and application thereof

A technology of polyurethane and artificial antigen, which is applied in the field of immunoassay, can solve problems such as unestablished, and achieve the effects of enhanced structural features, strong specificity, and high derivation efficiency

Active Publication Date: 2019-03-26
SOUTH CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are currently no reports on urethane haptens, antigens, and antibodies that can be used for immunoassays, so the urethane ELISA detection method has not yet been established

Method used

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  • A xanthene polyurethane hapten, artificial antigen and application thereof
  • A xanthene polyurethane hapten, artificial antigen and application thereof
  • A xanthene polyurethane hapten, artificial antigen and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Example 1 Urethane Hapten B Ⅰ (n=0) Preparation method

[0047] 178mg of ethyl carbamate was dissolved in 5mL of 1M acetic acid; 626mg of 9-hydroxy-9H-xanthene-3-carboxylic acid was dissolved in 20mL of methanol; the above solution was mixed and stirred at room temperature for 1 hour. Add 10 mL of distilled water to the mixture, remove the methanol in the reaction mixture by rotary evaporation, filter, wash the precipitate with 0.1M dilute hydrochloric acid, wash with distilled water, and dry to obtain 424 mg of gray solid, namely the target hapten XEC-313-3, the structural formula is as follows (Ⅳ) shown.

[0048]

[0049] Formula (Ⅳ).

[0050] ESI-MS analysis (negative)m / z 312[M+H] – ; 1 H NMR (600MHz, DMSO) δ8.21(d, J=8.8Hz, 1H), 7.71(dd, J=8.0, 1.6Hz, 1H), 7.61(d, J=1.6Hz, 1H), 7.51(d ,J=8.0Hz,1H),7.40(d,J=7.3Hz,1H),7.35(td,J=7.9,1.5Hz,1H),7.18(t,J=7.4Hz,3H),5.99(d ,J=8.6Hz,1H),4.06(q,J=7.0Hz,2H),1.18(t,J=7.1Hz,3H).

Embodiment 2

[0051] Example 2 Urethane Hapten B Ⅰ (n=1) preparation method

[0052]178mg of ethyl carbamate was dissolved in 5mL of 1M acetic acid; 654mg of 2-(9-hydroxy-9H-xanthene-4-yl)acetic acid was dissolved in 20mL of methanol; the mixture was mixed and stirred at room temperature for 1 hour. Add 10 mL of distilled water to the mixed solution, remove the methanol in the reaction mixed solution by rotary evaporation, filter, wash the precipitate with 0.1M dilute hydrochloric acid, wash with distilled water, and dry to obtain 402 mg of gray solid, namely the target hapten XEC-327-4, the structural formula is as follows (Ⅴ) shown.

[0053]

[0054] Formula (Ⅴ).

[0055] ESI-MS analysis (positive) m / z 350[M+Na] + ; 1 H NMR (600MHz, DMSO) δ8.09(d, J=9.0Hz, 1H), 7.36(d, J=7.6Hz, 1H), 7.30(t, J=7.2Hz, 1H), 7.21(dd, J =17.5,7.4Hz,2H),7.12(dd,J=13.9,7.1Hz,2H),7.02(t,J=7.5Hz,1H),5.92(d,J=8.9Hz,1H),4.06(q , J=7.1Hz, 2H), 3.52(dd, J=39.5, 15.3Hz, 2H), 1.18(t, J=7.1Hz, 3H).

Embodiment 3

[0056] The preparation method of embodiment 3 immunogen coating original

[0057] The difference between the preparation of the immunogen and the coating source lies in the carrier protein, the immunogen carrier protein uses bovine serum albumin (BSA), and the coating original carrier protein uses chicken ovalbumin (OVA). The preparation method of the immunogen is used as an example in the following.

[0058] Active ester method: take hapten B Ⅰ (n=0) 31.3mg (0.1mmoL) or hapten B Ⅰ (n=1) 32.7mg (0.1mmoL) was dissolved in 0.5mL DMF, stirred and added 25.6mg (0.1mmol) DCC and 11.5mg (0.1mmoL) NHS, magnetically stirred at 4°C overnight, the supernatant after centrifugation was A liquid. Weigh 20 mg of BSA or OVA and dissolve in 2 mL of PBS (pH 8.0) with a concentration of 0.1 mol / L, stir and dissolve to prepare liquid B. Under magnetic stirring, solution A was gradually dropped into solution B, and reacted at 4°C for 12 hours. After centrifugation, the supernatant was taken,...

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Abstract

The invention belongs to the technical field of immunodetection, and particularly discloses xanthene polyurethane hapten and artificial antigen and application thereof. The xanthene polyurethane hapten has a structure as shown in the formula (I) (please see the formula in the description), xanthene polyurethane artificial antigen can be obtained by coupling the xanthene polyurethane hapten with carrier protein, an experimental animal is immunized with the artificial antigen, and organism of the experimental animal generates an antibody specifically targeting xanthene polyurethane; the antibody can specifically identify a polyurethane xanthydrol derivative, namely, xanthene polyurethane which is used for indirectly detecting the content of polyurethane in food.

Description

technical field [0001] The invention relates to the technical field of immunoassay, in particular to a xanthene polyurethane hapten, an artificial antigen and applications thereof. Background technique [0002] Ethyl carbamate (EC for short), also known as urethane or urethane, the molecular formula is C 3 h 7 NO 2 , is a colorless, odorless powdery crystal, not volatile (boiling point 182-184 ° C), soluble in water and ethanol, is a chemical pollutant naturally formed in fermented food, especially alcoholic beverages, harmful to human health Potential threat of carcinogenesis; since Nettleship et al. discovered in 1943 that EC can lead to canceration of mouse cells and tumor formation, the carcinogenicity of EC has been proved in many model animals (rats, mice, hamsters and monkeys, etc.) . Based on these experimental results, it was classified as a 2B carcinogenic compound by the International Agency for Research on Cancer (IARC) in 1974. Since then, researchers have ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/86C07D311/88C07K14/765C07K16/44C07K16/06G01N33/52
CPCC07D311/86C07D311/88C07K14/765C07K16/065C07K16/44C07K19/00G01N33/52
Inventor 徐振林罗林孙远明杨金易雷红涛王弘沈玉栋刘功良
Owner SOUTH CHINA AGRI UNIV
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