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2,4,4'-tribromodiphenyl ether hapten preparation method and application thereof

A technology of tribrominated diphenyl ether and dibrominated diphenyl ether, applied in the field of biochemistry, can solve problems such as interference, rareness, low concentration, etc., and achieve the effects of fast speed, high yield and simple synthesis method

Inactive Publication Date: 2018-11-02
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, since there are many homologues of PBDEs, the concentration in environmental samples is extremely low, and they will be interfered by other organic compounds, a more accurate immunoassay method is needed to detect PBDEs in environmental samples. -28 immunoassay methods are relatively rare, and there are few research and application reports on the preparation of BDE-28 haptens and artificial whole antigens

Method used

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  • 2,4,4'-tribromodiphenyl ether hapten preparation method and application thereof
  • 2,4,4'-tribromodiphenyl ether hapten preparation method and application thereof
  • 2,4,4'-tribromodiphenyl ether hapten preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1 Preparation of BDE-28 Hapten

[0032] Dissolve 1.04g of 2,4-dibromophenol (4.13mmol) in 8mL of dry DMF, place in an ice bath and cool down to 0°C, add 0.199g of sodium hydride (8.28mmol) in batches, and stir in the ice bath for 20min , placed at room temperature for 10min; then slowly added 0.583g p-fluoronitrobenzene (4.13mmol), and stirred at 90°C for 2h; 2 Cl 2 After extraction (25mL×3), the organic extracts were combined and washed with anhydrous MgSO 4 Drying, rotary evaporation and concentration, and after separation and purification by silica gel column chromatography (eluent: n-hexane: ether = 2:3 (v / v)), the orange-yellow oily product 4-nitro-2',4' was obtained -Dibromodiphenyl ether, the yield is 66.1%.

[0033]The above 4-nitro-2′,4′-dibromodiphenyl ether (1.30mmol, 0.485g) was dissolved in 8mL of n-butylamine, formic acid (10.4mmol, 0.4mL) and platinum carbon (0.770g, 5% carbon loading) as a catalyst, the mixture was heated and stirred at 90°C ...

Embodiment 2

[0035] The preparation of embodiment 2 BDE-28 coating former

[0036] The BDE-28 hapten prepared in Example 1 is used to establish a variety of immunoassay methods and complete the detection of BDE-28 in environmental samples. One of the key uses is exactly to be used with carrier proteins such as bovine serum albumin (BSA), ovalbumin ( OVA), keyhole limpet hemocyanin (KLH) and other macromolecular protein carriers are coupled to prepare the BDE-28 artificial whole antigen. Dialdehyde method, diazotization method. Through the above-mentioned BDE-28 hapten (BDE-28-NH 2 ) is coupled with OVA to prepare the preparation route of BDE-28 coating agent as shown in formula (Ⅲ),

[0037]

[0038] The specific operation steps are as follows: take 0.0343gBDE-28-NH 2 (0.1mmol) into a 25mL Erlenmeyer flask, add 1mL N,N-dimethylformamide (DMF) dropwise, stir well and add dropwise to 10mL, 0.08mmol OVA solution (0.01M, pH7.40 phosphoric acid salt buffer solution), then slowly add 0.03...

Embodiment 3

[0040] Example 3 Immunoassay detection

[0041] Utilize the BDE-28 coated original prepared in embodiment 2 and polyclonal antibody (the polyclonal antibody used is obtained by BDE-28 artificial antigen successively immunizing New Zealand white rabbit several times) to establish the immune PCR method based on gold nanobiological probe (GNPs -iPCR), the specific operation steps of the GNPs-iPCR method are as follows:

[0042] a. Treat the PCR tube with 0.8% glutaraldehyde solution to enhance its surface adsorption, 20μL / well, incubate at 37°C for 6h, and use ddH 2 O Repeatedly wash the tube 3 times, 200μL / well, dry it and set aside; b. Dilute the original BDE-28 coating solution with 0.05M, pH9.60 carbonate buffer, add it to the PCR tube for coating, 20μL / well , overnight at 4°C; c. Pour off the original dilution of BDE-28 coating, wash the tube 3 times with PBST (0.01M, pH7.40 phosphate buffer + 0.05% Tween 20), 200μL / well, add 3% OVA (dissolved in 0.01M, pH 7.40 phosphate b...

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Abstract

The invention discloses a 2,4,4'-tribromodiphenyl ether hapten preparation method and application thereof. 2,4-dibromophenol and 4-fluoronitrobenzene are used as raw materials for electrophilic substitution reaction to synthesize 4-nitro-2',4'-dibromodiphenyl ether, and then through hydrogenation reduction reaction, a 2,4,4'-tribromodiphenyl ether hapten is prepared. By means of the method, the problem is solved that the 2,4,4'-tribromodiphenyl ether does not have an active group coupled to carrier protein, the method is simple, the speed is high, the yield is higher, the synthesized 2,4,4'-tribromodiphenyl ether hapten can be used for preparing a 2,4,4'-tribromodiphenyl ether artificial coating antigen and building a 2,4,4'-tribromodiphenyl ether Immunoassay method.

Description

technical field [0001] The invention belongs to the field of biochemistry, and relates to a preparation method and application of a tribromodiphenyl ether hapten, in particular to a preparation method and application of a 2,4,4'-tribromodiphenyl ether hapten. Background technique [0002] Polybrominated diphenyl ethers (PBDEs) are a kind of brominated flame retardants. Because of their high flame retardant efficiency, good thermal stability, small amount of addition, little effect on material properties, and low price, they are mass-produced and used as flame retardants. In polymers, especially in electrical manufacturing (television, computer circuit boards and casings, etc.), building materials, upholstery furniture, automotive interiors, decorative fabrics, foams, fibers, etc. 2,4,4′-Tribromodiphenyl ether (BDE-28) is one of polybrominated diphenyl ether homologues, which widely exists in environmental media such as air, water and soil, and BDE-28 is also commonly used in...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C217/90C07C213/02C07C201/12C07C205/38C07K14/765C07K14/77C07K14/795C07K16/44
CPCC07C201/12C07C213/02C07C217/90C07K14/765C07K14/77C07K14/795C07K16/44C07C205/38
Inventor 庄惠生马振
Owner SHANGHAI JIAO TONG UNIV
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