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Preparation method and application of 2,4,4'-tribromobiphenyl ether immunogen

A technology of tribrominated diphenyl ether and dibrominated diphenyl ether, applied in the field of biochemistry, can solve problems such as less research, and achieve the effects of simple synthesis method and high yield

Inactive Publication Date: 2018-11-06
SHANGHAI JIAO TONG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] At present, there are few reports on the immunoassay method of polybrominated diphenyl ether pollutants at home and abroad, and most studies focus on the tetrabromodiphenyl ether BDE-47 with a high detection rate, while the immunoassay on tribromodiphenyl ether BDE-28 There is very little research on the method. BDE-28 immunogen is the basis for establishing an immunoassay method for the determination of BDE-28. The preparation of BDE-28 immunogen has important application value and theoretical value

Method used

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  • Preparation method and application of 2,4,4'-tribromobiphenyl ether immunogen
  • Preparation method and application of 2,4,4'-tribromobiphenyl ether immunogen
  • Preparation method and application of 2,4,4'-tribromobiphenyl ether immunogen

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Experimental program
Comparison scheme
Effect test

Embodiment 1BD

[0032] The preparation of embodiment 1BDE-28 immunogen

[0033] Step 1: Dissolve 1.04g of 2,4-dibromophenol (4.13mmol) in 8mL of dry DMF, cool to 0°C in an ice bath; add 0.199g of sodium hydride (8.28mmol) in batches, and stir in an ice bath After 20 minutes, the reaction mixture was left at room temperature for 10 minutes; then 0.583 g of p-fluoronitrobenzene (4.13 mmol) was slowly added, heated and stirred at 90°C for 2 hours; 10 mL of ultrapure water (ddH 2 O), after slightly shaking several times, use CH 2 Cl 2 Extraction (25mL × 3), combined organic extracts, with anhydrous MgSO 4 After drying and concentrating by rotary evaporation, 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 (1.018 g).

[0034] In the second step, 0.485g of the above-mentioned 4-nitro-2', 4'-dibromodiphenyl ether (1.30mmol) was dissolved in 8mL of n-butyl...

Embodiment 2BD

[0043] The preparation of embodiment 2BDE-28 polyclonal antibody

[0044] Healthy New Zealand white rabbits were immunized with the immunogen BSA-BDE-28 prepared in Example 1 to prepare BDE-28 polyclonal antibody. For the initial immunization of rabbits, an equal proportion of Freund's complete adjuvant (CFA) and the immunogen was used (the protein concentration was 1 mg / mL), and for subsequent booster immunizations, an equal proportion of Freund's incomplete adjuvant (IFA) and the immunogen was used Mixed (protein concentration is 1mg / mL), the specific immunization scheme of white rabbit is shown in Table 2, adopts indirect competitive ELISA method to measure antiserum titer, the change of BDE-28 antibody titer is shown in the appendix Figure 5 As shown, the change of antiserum titer is the process of immune response again in purebred male New Zealand white rabbits. Both rabbits No. 1 and No. 2 used BSA-BDE-28 as the immunogen. With the increase of immunization times, rabbit...

Embodiment 3BD

[0047] The specificity of embodiment 3BDE-28 polyclonal antibody

[0048] 2,2',4,4'-tetrabromodiphenyl ether (CAS: 5436-43-1), 2,3',4,4'-tetrabromodiphenyl ether (CAS: 189084-61-5 ), 2,3,3',4,4'-pentabromodiphenyl ether (CAS: 373594-78-6), 2,2',4,4',5-pentabromodiphenyl ether (CAS: 60348 -60-9), 2,2',4,4',6-pentabromodiphenyl ether (CAS: 189084-64-8), 2,2',4,4',5,5'-hexabromodiphenyl ether Diphenyl ether (CAS: 67774-32-7), 2,2',3,4,4',5',6-heptabromodiphenyl ether (CAS: 68928-80-3), decabromodiphenyl ether (CAS: 1163-19-5) As a structural analogue of BDE-28, the specificity of the BDE-28 polyclonal antibody was determined by indirect competition ELISA, and the cross-reaction between pAb-BDE-28 and BDE-28 analogues was calculated ( CR) to evaluate the specificity of pAb-BDE-28, wherein, the chemical structure and cross-reactivity results of BDE-28 analogues are shown in Table 3. It can be concluded that the cross-reactivity rates between pAb-BDE-28 and compounds similar to B...

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Abstract

The invention discloses a preparation method and an application of a 2,4,4'-tribromobiphenyl ether immunogen. 4-nitro-2',4'-dibromodiphenyl ether is synthesized from 2,4-dibromophenol and 4-fluoronitrobenzene as raw materials through electrophilic substitution reaction; then, a 2,4,4'-tribromodiphenyl ether hapten containing an amino active group is prepared through hydrogenation reduction reaction, and the 2,4,4'-tribromobiphenyl ether immunogen is prepared from the 2,4,4'-tribromodiphenyl ether hapten and bovine serum albumin by coupling with a diazotization method. The preparation method ofthe 2,4,4'-tribromobiphenyl ether immunogen is rapid and simple, can be used for preparing 2,4,4'-tribromobiphenyl ether artificial polyclonal antibodies and has a significant effect on establishmentof immunoassay methods associated with 2,4,4'-tribromobiphenyl ether.

Description

technical field [0001] The invention belongs to the field of biochemistry, and specifically relates to a preparation method and application of a 2,4,4'-tribromodiphenyl ether immunogen. Background technique [0002] 2,4,4'-Tribromodiphenyl ether (BDE-28) is one of the most widely distributed and most toxic PBDEs congeners in environmental media. Different from commercial polybrominated diphenyl ethers, BDE-28 is a low-bromine substituted diphenyl ether, and there is no commercial product. BDE-28 is hydrophobic, persistent and bioaccumulative. Studies have shown that BDE-28 is prone to damage to animal livers and kidneys. , the endocrine of the thyroid gland and the development of the nervous system cause harm, and will induce mutations in the organism. Even if a small amount of BDE-28 enters the environmental medium, it will enter the organism through respiration or skin contact, and cause the organism to be poisoned through biomagnification; In complex environmental media,...

Claims

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Application Information

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IPC IPC(8): C07K14/765C07K1/107C07K16/44G01N33/531
CPCC07K14/765C07K16/44C07K19/00G01N33/531G01N33/68
Inventor 庄惠生马振
Owner SHANGHAI JIAO TONG UNIV
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