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Leuco malachite green hapten, artificial antigen and preparation method

A leuco malachite green and artificial antigen technology, applied in the field of immunochemistry, can solve the problems of low recovery rate, weak antibody specificity and sensitivity, etc.

Active Publication Date: 2015-08-19
WUXI ZODOLABS BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] However, the above inventions are the same as the prior art, and their antibody specificity and sensitivity are weak, and the recovery rate is too low during detection, which cannot meet the existing needs.

Method used

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  • Leuco malachite green hapten, artificial antigen and preparation method
  • Leuco malachite green hapten, artificial antigen and preparation method
  • Leuco malachite green hapten, artificial antigen and preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0071] Take 2.5g (20mmol) of N,N-dimethylaniline into a 50mL two-necked flask, then slowly add 20mL of 5% Amberlyst15 resin toluene solution, stir magnetically for a few minutes, and add 1.50g p-formylbenzene under stirring Formic acid or m-formylbenzoic acid, stirred overnight at 80~100°C. After the reaction was completed, the catalyst was filtered, and saturated sodium bicarbonate solution was added to the reaction system to adjust the pH to 9.0, and extracted with dichloromethane. The pH of the aqueous phase was adjusted to 2.0 with dilute hydrochloric acid, extracted with ethyl acetate, and the organic phase was spun to dryness to obtain a crude product. Then add 2g of HATU, 0.5g of ethylenediamine, 2ml of DIPEA, dissolve in 20mL of DMF, stir magnetically at 50°C for 2h, add water to quench and extract with ethyl acetate, spin the organic phase to dryness, and finally use vacuum silica gel column chromatography Separation and purification yielded the desired product.

[...

Embodiment 2

[0076] Take 2.5g (20mmol) of N,N-dimethylaniline into a 50mL two-necked flask, slowly add 20mL of 5% Amberlyst15 resin toluene solution, stir magnetically for a few minutes, and add 1.50g of the compound of formula (XI) under stirring (where R 6 for CONH 2 , R 7 for H, or R 6 for H, R 7 for CONH 2 ), and stirred overnight at 80~100°C. After the reaction was completed, the catalyst was filtered, and saturated sodium bicarbonate solution was added to the reaction system to adjust the pH to 9.0, extracted with ethyl acetate, and the organic phase was rotary evaporated and spin-dried to obtain a crude product. Then dissolve in 10mL tetrahydrofuran, add 1.5g lithium aluminum tetrahydrogen, and stir the reaction with magnetic force at 0°C for 2h, quench with ammonium chloride solution, adjust the pH to 9.0, extract with ethyl acetate, spin the organic phase to dryness, and finally The desired compound was separated and purified by silica gel column chromatography. Then dissol...

Embodiment 3

[0081] Take 2.5g (20mmol) of N,N-dimethylaniline into a 50mL two-necked flask, then slowly add 20mL of 5% Amberlyst15 resin toluene solution, stir magnetically for a few minutes, and add 1.50g p-formylbenzene under stirring Formic acid or m-formylbenzoic acid, stirred overnight at 80~100°C. After the reaction was completed, the catalyst was filtered and saturated sodium bicarbonate solution was added to the reaction system to adjust the pH to 9.0, and extracted with dichloromethane. The pH of the aqueous phase was adjusted to 2.0 with dilute hydrochloric acid, extracted with ethyl acetate, and the organic phase was spun to dryness to obtain a crude product. Then add 2g of HATU, 2g of the compound of formula (g), 2mL of DIPEA, dissolve in 20mL of DMF, stir with magnetic force at 50°C for 2h, add water to quench and extract with ethyl acetate, spin the organic phase to dryness, and finally use decompression silica gel The desired product was obtained by separation and purificat...

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Abstract

The invention discloses malachite green hapten, malachite green artificial antigen and preparation methods of the malachite green hapten and artificial antigen. The malachite green hapten retains the feature structure of malachite green, and has active arms which are derived from different microdomains of the structure of malachite green, have different electron cloud densities and different carbon chain lengths, are suitable to be coupled with macromolecule carriers, and are amide linkage with amino or carboxyl tail end. The malachite green artificial antigen prepared with leucomalachite green hapten has very high specificity and sensitivity when applied to detection of the residual quantity of leucomalachite green and malachite green, and is high in accuracy and recovery. Moreover, the methods are simple, the cost is low, and a fast, sensitive, economical and efficient malachite green immunodetection method is established.

Description

technical field [0001] The invention belongs to the technical field of immunochemistry and relates to the preparation of antigens, in particular to a leuco malachite green hapten, an artificial antigen and a preparation method. Background technique [0002] Malachite Green (Malachite Green, MG), also known as China Green, Aniline Green, Alkaline Malachite Green, Magenta Green, Salt-based Block Green, etc., is a toxic triphenylmethane compound that used to be used as a topical insect repellant , fungicides, bactericides, etc. are used to treat parasitic, fungal or bacterial infections in fish or fish eggs. However, malachite green is also a potential carcinogen, mutagen, and mutagen. Many countries in the world have listed malachite green as a banned drug for aquaculture. Leucomalachite Green (Leucomalachite Green, LMG) is the chromophore-free reduction product of malachite green. It is the main metabolite and existing form of malachite green in fish and other organisms. It ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C237/34C07C233/36C07C231/02C07K14/765G01N33/577
CPCC09B11/12
Inventor 卞禹卜叶帮伟高君金晶刘春梅沈智勇杨晓慧李林
Owner WUXI ZODOLABS BIOTECH
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