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5-methyl morpholine-3-amino-2-oxazolidinone derivative hapten, antigen and antibody, and application thereof

A technology of methylmorpholine and oxazolidinone, applied in the field of immunology, to achieve high titer, high sensitivity and stable results

Inactive Publication Date: 2012-05-09
SOUTH CHINA AGRI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006]Theoretically, it is possible to prepare small molecule hapten antibodies of all prototype drugs, but it also requires specific and specific technical solutions to achieve specific antibodies according to target drugs Preparation of 5-methylmorpholine-3-amino-2-oxazolidinone haptens, antigens and antibodies available for ELISA detection, making 5-methylmorpholine-3-amino- 2-oxazolidinone ELISA detection method has not yet been established

Method used

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  • 5-methyl morpholine-3-amino-2-oxazolidinone derivative hapten, antigen and antibody, and application thereof
  • 5-methyl morpholine-3-amino-2-oxazolidinone derivative hapten, antigen and antibody, and application thereof
  • 5-methyl morpholine-3-amino-2-oxazolidinone derivative hapten, antigen and antibody, and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1 Preparation method of 5-methylmorpholine-3-amino-2-oxazolidinone derivative hapten MCPAMOZ

[0039] Add 1.15g of p-carboxybenzaldehyde into a 50ml round bottom flask, slowly add methanol until the p-carboxybenzaldehyde is completely dissolved, add 0.5g of 5-methylmorpholine-3-amino-2-oxazolidinone while stirring, and stir at room temperature overnight. Reaction finishes filtering, washes twice with water, washes twice with methanol, is dried, and obtains 0.80g white powder, and its structural formula is as shown in (I). ESI-MS (negative) m / z: 332 (M—H) - . 1 H NMR (400MHz, d 5 -Pyridine, TMS): δ 8.44 (d, J=8.3, 2H); 7.99 (d, J=8.3, 2H) 7.94 (s, 1H); 4.96 (qd, J 1 =6.2,J 2 =6.2,J 3 =6.3,J 4 = 8.4, 1H); 4.09 (t, J = 8.9Hz, 1H); 3.78 (dd, J1 = 6.7, J2 = 8.8, 1H); 3.69-3.64 (m, 4H); 2.67 (dd, J 1 =6.2,J 2 = 13.3, 1H); 2.61 (dd, J 1 =5.7,J 2 =13.4); 2.51-2.46 (m, 4H)

[0040]

[0041]

Embodiment 2

[0042] Example 2 Preparation method of 5-methylmorpholine-3-amino-2-oxazolidinone derivative hapten CEPAMOZ

[0043]Add 1.06g of 2-(4-formylphenoxy)acetic acid into the round bottom flask, slowly add methanol until p-carboxybenzaldehyde is completely dissolved, add 0.5g of 5-methylmorpholine-3-amino-2-oxazole while stirring Alkanone, stirred overnight at room temperature. After the reaction was completed, filtered, washed twice with water and twice with methanol, and dried to obtain 0.93 g of white powder, the structural formula of which was shown in formula (II). ESI-MS (negative) m / z: 362 (M-H) - . 1 H NMR (600MHz, d 5 -Pyridine, TMS): δ 7.89-7.87 (m.3H); 7.22 (d, J=8.8, 2H); 5.02 (s, 2H); 4.88 (qd, J 1 =6.31, J2=6.31, J3=6.35, J4=8.5, 1H); 4.01(t, J=8.8Hz, 1H); 3.70(dd, J1=6.8, J2=8.7, 1H); 3.67-3.65(m , 4H); 2.63(dd, J1=6.2, J2=13.3, 1H); 2.56(dd, J1=5.6, J2=13.4); 2.51-2.44(m, 4H)

[0044]

Embodiment 3

[0045] Example 3 Preparation method of immunogen CEPAMOZ-BSA

[0046] Dissolve 0.1mmol of the hapten CEPAMOZ in 2ml of DMF, stir and add 27.5mg of DCC and 14.4mg of NHS, and react overnight with magnetic stirring at 4°C. After centrifugation, the supernatant is liquid A; weigh 140mg of BSA and dissolve in 10ml with a concentration of 0.1mol / L Add 1ml of DMF to the PBS (pH8.0), stir and dissolve to prepare liquid B; under magnetic stirring, liquid A is gradually dropped into liquid B, and react at 4°C for 12 hours. After centrifugation, take the supernatant, dialyze with normal saline at 4°C for 3 days, change the dialysate 3 times a day, and distribute the whole antigen in 0.5ml at a concentration of 1mg / ml

[0047] Store in a centrifuge tube and freeze at -20°C for immunization. The structure of the prepared 5-methylmorpholine-3-amino-2-oxazolidinone derivative immunogen CEPAMOZ-BSA is shown in formula (V):

[0048]

[0049] Immunogen identification: The carrier protein ...

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Abstract

The invention discloses a method for preparing hapten, antigen and antibody of 5-methylmorpholine-3-amino-2-oxazolidone derivatives. The hapten obtained by designing and preparing the 5-methylmorpholine-3-amino-2-oxazolidone derivatives is similar to counterparts of the 5-methylmorpholine-3-amino-2-oxazolidone derivatives in molecular structure, spatial chemistry and electron distribution. The linking arm in the hapten structure is not easy to induce and generate 'arm antibody', and the organism is easier to identify as a saturate carbon chain of a certain length is used; the antigen which isprepared by hapten cross coupling carrier protein ensures the organism to produce the antibody of high tilter and good specificity in accordance with the 5-methylmorpholine-3-amino-2-oxazolidone derivatives; and the antibody is used for detecting the residue of 5-methylmorpholine-3-amino-2-oxazolidone in animal source food with quick response and stable result.

Description

technical field [0001] The invention belongs to the technical field of immunology, and in particular relates to 5-methylmorpholine-3-amino-2-oxazolidinone derivative hapten, antigen, antibody and preparation method thereof, and prepared 5-methylmorpholine -3-amino-2-oxazolidinone derivative hapten, antigen and antibody and application of antibody. Background technique [0002] Furaltadone, a nitrofuran drug, is a broad-spectrum antibiotic that has certain antibacterial effects on both Gram-positive and Gram-negative bacteria. However, relevant studies have proved that nitrofuran drugs and their metabolites have considerable toxicity, teratogenic side effects, and can induce cancer, which has attracted people's attention. In July 1990, the European Union promulgated Regulation 2377 / 90 / EEC, which listed nitrofuran drugs and their metabolites as Class A prohibited drugs, and stipulated that the detection limit of their residues in food of animal origin was 1.0 μg / kg. Since 1...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D263/26C07K16/06G01N33/536
Inventor 沈玉栋张世伟孙远明王弘雷红涛肖治理杨金易
Owner SOUTH CHINA AGRI UNIV
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