CN101519367A - Propoxur artificial antigen and method for synthesizing same - Google Patents
Propoxur artificial antigen and method for synthesizing same Download PDFInfo
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- CN101519367A CN101519367A CN 200910029608 CN200910029608A CN101519367A CN 101519367 A CN101519367 A CN 101519367A CN 200910029608 CN200910029608 CN 200910029608 CN 200910029608 A CN200910029608 A CN 200910029608A CN 101519367 A CN101519367 A CN 101519367A
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Abstract
The invention provides a propoxur artificial antigen and a method for synthesizing the same, and belongs to the technical fields of organic chemistry and immunochemistry. The chemical name of the propoxur is 2-(1-isopropoxy) phenyl methyl carbamate, which belongs to a pesticide of carbamate agricultural chemicals. The synthesis method comprises the followings steps that: the propoxur is taken as a raw material, and orderly subjected to nitration reaction, reducing reaction and acidylation reaction to successfully synthesize Hapten 1 and Hapten 2 which have different active groups of -NH2 or -COOH and different connection arm lengths; and the Hapten 1 and Hapten 2 are successfully coupled with bovine serum albumin(BSA) by the diazo method and the mixed anhydride method respectively to obtain the artificial antigen 1(Hapten 1-BSA) and the artificial antigen 2(Hapten 2-BSA) which have different connection arm lengths, thereby creating conditions for further researching the propoxur enzyme coupling immunity retention analysis method. The artificial antigen and the method have the advantages of simple and feasible antigen preparation technique, unnecessary special equipment in the process of preparing the antigen, unnecessary use of an extremely toxic substance, namely carbonyl chloride, mild reaction conditions, low cost and easy mass production.
Description
Technical field
A kind of Propoxur artificial antigen and synthetic method thereof belong to organic chemistry and immunochemical technique field.Synthetic Propoxur artificial antigen of the present invention is used to prepare the antibody of specific recognition chemical pesticide Propoxur and the immune quick testing reagent box of the efficient rapid detection Propoxur content of development.
Background technology
Propoxur (Propoxur) belongs to the amino formate chemical insecticide, is one of four carbamate insecticidess of The World Health Organization (WHO) approval and the domestic hygiene pest control recommended.At first succeed in developing country's " the Seventh Five-Year Plan " introduced variety by Bayer A.G.The Propoxur preparation is mainly used in cash crop pest control (as cotten aphid, vegetable aphid etc.), and the various sanitary insect pests (mosquito, fly, cockroach etc.) of eliminating family and public place, have tag, stomach toxicity and fumigation action, knock down fast, lasting period is long, and characteristics such as insecticidal spectrum is wide, residual effect length, kill ratio height.Domestic existing producer carries out the scale operation of former medicine and preparation and obtains excellent popularization at present.
The Propoxur detection method numerous researchs have been carried out both at home and abroad.Bibliographical information Propoxur effective constituent detection method is had vapor-phase chromatography, high performance liquid chromatography, thin layer chromatography etc., but these traditional detection methods need expensive equipment, special operator, sample preparation complexity, cost height, time long, can not satisfy that requirement is detected at fast and convenient scene and big area is promoted the use of.And enzyme-linked immune analytic method (ELISA) has shown wide application prospect owing to have special, responsive, simple, quick, expense and hang down and reach advantages such as the requirement of sample purifying is low in pesticide residue analysis.
Because most of agricultural chemicals are small-molecule substance (molecular weight is less than 1000), itself do not have immunogenicity (being called haptens), must prepare artificial antigen with the macromolecular carrier coupling, could the inducing specific production of antibodies.For this reason, must manage earlier agricultural chemicals small molecules and carrier protein coupling to be prepared pesticide artificial antigen.Yet the Propoxur molecule can not need to introduce active function group by chemical reaction on pesticide molecule earlier directly by bi-functional cross-linking agent and protein covalent coupling,, makes it and the protein coupling as haptens with this again.Therefore haptenic design, synthetic be the key point of setting up the Propoxur enzyme-linked immune analytic method.
Haptenic synthetic about Propoxur, has only Maria J.Moreno (J.Agric.Food Chem.2001 at present, 49,72-78) wait a kind of synthetic method of people at the calendar year 2001 report, they prepare the neighbour-different third phenoxy formyl chloride with neighbour-isopropoxy phenol and highly toxic product phosgene reaction, and then prepare haptens with γ-butylamine acid-respons, reaction formula is as follows:
Use hypertoxicity material phosgene in this synthesis of semiantigen, and reaction conditions is comparatively harsh, this will become the development of Propoxur test kit and produce the bottleneck that is difficult to break through in enormous quantities.Moreover on the Propoxur phenyl ring N-methyl carbamate key as the feature structure of carbamate chemicals for agriculture, and above-mentioned haptenic synthetic exactly from this feature structure one end introducing active group carboxyl, this certainly will give in the elisa assay in later stage bring certain influence.
Summary of the invention
The purpose of this invention is to provide a kind of new Propoxur artificial antigen and synthetic method thereof, for the enzyme linked immunological retention analysis method of further studying Propoxur provides research technique.
The present invention successfully introduces active group amino (NH not destroying under the Propoxur precursor structure situation on phenyl ring
2), prepare haptens Hapten 1, the hydroxy-acid group that prolongs 4 carbon of connecting arm introducing then on amino (COOH), is prepared haptens Hapten 2.By simple 3 step reactions, prepared have different active groups, two kinds of haptens of different connection brachium, and reaction conditions gentleness, simple to operate.
Secondly, the haptens Hapten 1 with different activities group can prepare artificial antigen with different carrier protein couplings with Hapten 2.In the present invention, select for use bovine serum albumin (BSA) the most commonly used and that physico-chemical property is stable, cheap and easy to get to pass through diazonium method and mixed anhydride method success coupling with haptens Hapten 1 and Hapten 2 respectively, prepare artificial antigen 1 and artificial antigen 2 as carrier proteins.
Technical scheme of the present invention: a kind of Propoxur haptens, with Propoxur 2-(1-isopropoxy) phenol methylcarbamate is raw material, carries out nitration reaction, reduction reaction successively, make Propoxur haptens Hapten 1, then Hapten 1 acidylate is made Propoxur haptens Hapten 2;
Described Propoxur haptens Hapten 1, chemical name are 2-isopropoxy-5-aminophenyl-N-methyl carbamate;
And described Propoxur haptens Hapten 2, chemical name is 4-[4-isopropoxy-3-(N-methyl carbamate base) anilino]-4-carbonyl butyric acid.
A kind of Propoxur artificial antigen, with described Propoxur haptens and bovine serum albumin coupling and product;
Propoxur artificial antigen 1, its chemical name are 2-isopropoxy-5-aminophenyl-N-methyl carbamate-bovine serum albumin, abbreviate antigen Hapten 1-BSA as;
And Propoxur artificial antigen 2, its chemical name is 4-[4-isopropoxy-3-(N-methyl carbamate base) anilino]-4-carbonyl butyric acid-bovine serum albumin, abbreviate antigen Hapten 2-BSA as.
The haptenic preparation method of described Propoxur, preparation Propoxur haptens Hapten 1 and Propoxur haptens Hapten 2:
With the Propoxur is raw material, carries out nitration reaction successively, and reduction reaction makes Propoxur haptens Hapten1, then Hapten 1 acidylate is made Propoxur haptens Hapten 2; Its synthetic route is as follows:
A), 2-isopropoxy-5-nitrophenyl-N-methyl carbamate is synthetic: in the 100mL three-necked flask, add the 20.9g Propoxur, the vitriol oil of 40mL, the concentrated nitric acid of 30mL, 80 ℃ of following insulation reaction 3h, reaction solution is poured in the frozen water, suction filtration, the solid ethyl alcohol recrystallization obtains needle crystal 2-isopropoxy-5-nitrophenyl-N-methyl carbamate;
B), 2-isopropoxy-5-aminophenyl-N-methyl carbamate Hapten's 1 is synthetic: take by weighing 2-isopropoxy-5-nitrophenyl-N-methyl carbamate 5.0g and be dissolved in the 50mL methyl alcohol, stir and add 0.5g Pd/C catalyzer [w (Pd)=10% industrial goods] down, feed hydrogen, room temperature reaction 8h, suction filtration, underpressure distillation, recrystallizing methanol get tabular crystal 2-isopropoxy-5-aminophenyl-N-methyl carbamate Hapten 1;
And c), 4-[4-isopropoxy-3-(N-methyl carbamate base) anilino]-4-carbonyl butyric acid Hapten 2 synthetic: take by weighing 4.48g 2-isopropoxy-5-aminophenyl-N-methyl carbamate Hapten 1,2.1g Succinic anhydried is in reaction flask, anhydrous pyridine 100mL stirring and dissolving, N
2Protection, 50 ℃ are reacted 6h down, and the reaction solution underpressure distillation gets the field gray thick substances;
The dope NaHCO of mass concentration 10%
3The solution dissolving with dilute hydrochloric acid regulator solution pH 2, is separated out cotton-shaped solid, and re-crystallizing in ethyl acetate gets white solid 4-[4-isopropoxy-3-(N-methyl carbamate base) anilino]-4-carbonyl butyric acid Hapten 2.
The preparation method of described Propoxur artificial antigen 1,
Carry out the synthetic of Propoxur artificial antigen 1 by following chemical equation:
Take by weighing 22.4mg Propoxur haptens Hapten 1 in the flask of 50mL, add 4mL DMF dissolving, add 0.5M HCl solution 2mL and 0.1M NaNO again
2Solution 1.2mL, 4 ℃ of following stirring reaction 30min add 3.6mg urea in the flask, continue to stir 5min, get Propoxur haptens Hapten 1 diazotization component;
Taking by weighing the 240mg bovine serum albumin is dissolved in the borate buffer solution of 30mL 0.15M, pH 8.7, under 4 ℃, dropwise join the diazotization component of preparation in the bovine serum albumin solution, stir 12h, afterwards coupling liquid is packed in the dialysis tubing, under 4 ℃, in the PBS buffered soln of 0.01M, pH 7.5, stir dialysis, change dialyzate every day 3 times, dialysed altogether 4-6 days, after dialysis finishes milk sap in the dialysis tubing is sub-packed in the centrifuge tube of 1mL, in-20 ℃ of refrigerators, deposits standbyly, be Propoxur artificial antigen Hapten 1-BSA.
The preparation method of described Propoxur artificial antigen 2, carry out the synthetic of Propoxur artificial antigen 2 by following chemical equation:
Take by weighing 17.5mg Propoxur haptens Hapten 2 and join in the 50mL flask, add 1mL DMF dissolving, then add tri-n-butylamine 15.39 μ L, isobutyl chlorocarbonate 8.4 μ L, stirring reaction 1h under the room temperature gets Propoxur haptens Hapten 2 active liquid;
Taking by weighing the 100mg bovine serum albumin is dissolved in the carbonate buffer solution of 6mL 0.05M, pH 9.6, and above-mentioned active drop is added in the bovine serum albumin solution, stir 2-3h under the room temperature, coupling liquid is packed in the dialysis tubing, in the PBS buffered soln of 0.01M, pH 7.5, stir dialysis under 40 ℃, change dialyzate every day 3 times, dialysed altogether 4-6 days, dialysis is sub-packed in transparent liquid in the dialysis tubing in the centrifuge tube of 1mL after finishing, in-20 ℃ of refrigerators, deposit standbyly, be Propoxur artificial antigen Hapten 2-BSA.
Beneficial effect of the present invention: the present invention compares with existing method, and its advantage and positively effect show:
(1) antigen is practical: the antigen of Propoxur is synthetic to have important use value and practical significance with antibody production techniques.Has an active group (NH with aforesaid method is synthetic
2Or-COOH) Propoxur agricultural chemicals similar structures, effectively prepare and have different two kinds of artificial antigens of Propoxur that connect brachium, for the enzyme linked immunological retention analysis method of further studying Propoxur has been created condition, for the development of Propoxur immunity quick testing reagent box has solved technological difficulties, will promote the appearance of China's Propoxur immunity quick testing reagent box.
(2) has comparability: the artificial antigen of preparing by the two kinds of haptens and the carrier protein couplet of different connection brachiums, thereby produce the antibody of different specific recognition Propoxur agricultural chemicals, can the different influences that connect the artificial antigens of brachium to the generation of Propoxur enzyme-linked immunosorbent assay of qualitatively analyze.
(3) the antigen prepd technology is simple and feasible: antigenic whole process of preparation need not special equipment and has avoided use hypertoxicity material phosgene, and mild condition is with low cost, batch production scale production easily.
Description of drawings
Fig. 1 haptens Hapten1, carrier proteins BSA, artificial antigen 1 ultraviolet spectrogram.
Fig. 2 haptens Hapten2, carrier proteins BSA, artificial antigen 2 ultraviolet spectrograms.
Embodiment
Embodiment 1: Propoxur haptens Hapten 1 is synthetic with haptens Hapten's 2
With the Propoxur is raw material, carries out nitration reaction successively, and reduction reaction makes Propoxur haptens Hapten1, then Hapten 1 acidylate is got Propoxur haptens Hapten 2; Synthesis step is as follows:
A), 2-isopropoxy-5-nitrophenyl-N-methyl carbamate (compound 2) is synthetic: in the 100mL three-necked flask, add Propoxur 20.9g, the vitriol oil of 40mL, the concentrated nitric acid of 30mL, 80 ℃ of following insulation reaction 3h pour reaction solution in the frozen water into, separate out light yellow solid, suction filtration, distilled water wash, the solid ethyl alcohol recrystallization obtains the transparent needle crystal 2-isopropoxy-5-nitrophenyl-N-methyl carbamate 21.8g of white, yield is 86%, m.p.120-121 ℃;
B), 2-isopropoxy-5-aminophenyl-N-methyl carbamate (Hapten1) is synthetic: take by weighing 2-isopropoxy-5-nitrophenyl-N-methyl carbamate 5.0g and be dissolved in the 50mL methyl alcohol, stir and add 0.5g Pd/C catalyzer [w (Pd)=10% industrial goods] down, feed hydrogen, stirring reaction 8h under the room temperature.Suction filtration, underpressure distillation get light brown solid, and recrystallizing methanol gets white diamond platy crystal 2-isopropoxy-5-aminophenyl-N-methyl carbamate (Hapten 1) 4.3g, and yield is 96%, m.p.102-102.8 ℃;
Analytical data: IR (KBr) v:3432,1638,1506,1453,1172cm
-1 1H-NMR (500MHz, DMSO): δ ppm 7.45 (s, 1H), 6.27～6.74 (m, 3H), 4.8 (s, 2H),, 4.15 (m, 1H), 2.63 (d, 3H), 1.15 (d, 6H); MS (m/z): 247 (M+Na
+), 224 (M
+); Ultimate analysis C
11H
16N
2O
3%: measured value (theoretical value) C 58.89 (58.91), H 7.16 (7.19), and N 12.48 (12.49).
C), 4-[4-isopropoxy-3-(N-methyl carbamate base) anilino]-4-carbonyl butyric acid (Hapten 2) synthetic: take by weighing 4.48g 2-isopropoxy-5-aminophenyl-N-methyl carbamate (Hapten 1); 2.1g Succinic anhydried; anhydrous pyridine 100mL stirring and dissolving; nitrogen protection; oil bath, 50 ℃ are reacted 6h down.The reaction solution underpressure distillation gets the field gray thick substances;
Dope is with 10% NaHCO
3The solution dissolving, dilute hydrochloric acid regulator solution pH=2 separates out cotton-shaped solid in the solution, re-crystallizing in ethyl acetate, get white cotton-shaped solid 4-[4-isopropoxy-3-(N-methyl carbamate base) anilino]-4-carbonyl butyric acid (Hapten 2) 5.6g, yield is 87.5%, m.p.218-219 ℃;
Analytical data: IR (KBr) v:3434,1657,1611,1453,1165cm
-1 1H-NMR (500MHz, DMSO): δ ppm 9.87 (s, 1H), 7.63-7.49 (m, 1H), 7.36 (d, J=2.31Hz, 1H), 7.24 (d, J=8.87Hz, 1H), 6.98 (d, J=9.01Hz, 1H), 4.50-4.34 (m, 1H), 2.63 (d, J=4.39Hz, 3H), 2.49 (s, 4H), 1.18 (d, J=5.99Hz, 6H); MS (m/z): 347.6 (M+Na
+), 325.6 (M+1); Ultimate analysis C
15H
20N
2O
6%: measured value (theoretical value) C 55.68 (55.55), H 6.18 (6.22), N8.59 (8.64).
Embodiment 2: artificial antigen 1 (Hapten 1-BSA) synthetic
Concrete steps: take by weighing 22.4mg Propoxur haptens Hapten 1 in the flask of 50mL, add the 4mLDMF dissolving, add 0.5M HCl solution 2mL and 0.1M NaNO again
2Solution 1.2mL, 4 ℃ of following stirring reaction 30min add 3.6mg urea in the flask, continue to stir 5min, get Propoxur haptens Hapten 1 diazotization component;
Taking by weighing 240mg bovine serum albumin (BSA) is dissolved in the borate buffer solution (pH=8.7) of 30mL 0.15M, under 4 ℃, the diazotization component of preparation is dropwise joined in the protein soln, stir 12h, in the dialysis tubing of afterwards coupling liquid being packed into, under 4 ℃, in the PBS of 0.01M buffered soln (pH=7.5), stir dialysis, change dialyzate every day 3 times, dialysed altogether 4-6 days, dialysis is sub-packed in milk sap in the dialysis tubing in the centrifuge tube of 1mL after finishing, and deposits standby in-20 ℃ of refrigerators;
The evaluation of artificial antigen: ultraviolet spectroscopy is adopted in the evaluation of artificial antigen, with haptens Hapten1, and carrier proteins BSA, the ultraviolet spectrogram of the different concns of conjugate Hapten1-BSA correspondence is done contrast (Fig. 1), and the UV spectrum curve after the coupling changes; Analyze conjugate Hapten1-BSA from spectroscopic data and stronger absorption peak occurred, can prove that haptens and carrier protein couplet at 389nm.
Embodiment 3: artificial antigen 2 (Hapten 2-BSA) synthetic
Concrete steps: take by weighing 17.5mg Propoxur haptens Hapten 2 and join in the 50mL flask, add the 1mLDMF dissolving, then add tri-n-butylamine 15.39 μ L, isobutyl chlorocarbonate 8.4 μ L, stirring reaction 1h under the room temperature gets Propoxur haptens Hapten 2 active liquid;
Taking by weighing 100mg bovine serum albumin (BSA) is dissolved in the carbonate buffer solution (pH=9.6) of 6mL 0.05M, and above-mentioned active drop added in the BSA solution, stir 2-3h under the room temperature, coupling liquid is packed in the dialysis tubing, in the PBS of 0.01M buffered soln (pH=7.5), stir dialysis under 4 ℃, change dialyzate every day 3 times, dialysed altogether 4-6 days, dialysis is sub-packed in transparent liquid in the dialysis tubing in the centrifuge tube of 1mL after finishing, and deposits standby in-20 ℃ of refrigerators.
The evaluation of artificial antigen: ultraviolet spectroscopy is adopted in the evaluation of artificial antigen, with haptens Hapten2, carrier proteins BSA, the ultraviolet spectrogram of the different concns of conjugate Hapten2-BSA correspondence is done contrast (Fig. 2), UV spectrum curve after the coupling has obvious variation, can prove that haptens and carrier protein couplet.
Claims (5)
1, a kind of Propoxur haptens, it is characterized in that: with Propoxur 2-(1-isopropoxy) phenol methylcarbamate is raw material, carries out nitration reaction, reduction reaction successively, make Propoxur haptens Hapten1, then Hapten 1 acidylate is made Propoxur haptens Hapten 2;
Described Propoxur haptens Hapten 1, chemical name are 2-isopropoxy-5-aminophenyl-N-methyl carbamate;
And described Propoxur haptens Hapten 2, chemical name is 4-[4-isopropoxy-3-(N-methyl carbamate base) anilino]-4-carbonyl butyric acid.
2, a kind of Propoxur artificial antigen is characterized in that: with the described Propoxur haptens of claim 1 and bovine serum albumin coupling and must product;
Propoxur artificial antigen 1, its chemical name are 2-isopropoxy-5-aminophenyl-N-methyl carbamate-bovine serum albumin, abbreviate antigen Hapten1-BSA as;
And Propoxur artificial antigen 2, its chemical name is 4-[4-isopropoxy-3-(N-methyl carbamate base) anilino]-4-carbonyl butyric acid-bovine serum albumin, abbreviate antigen Hapten2-BSA as.
3, the haptenic preparation method of the described Propoxur of claim 1 is characterized in that preparing Propoxur haptens Hapten 1 and Propoxur haptens Hapten 2:
With the Propoxur is raw material, carries out nitration reaction successively, and reduction reaction makes Propoxur haptens Hapten1, then Hapten 1 acidylate is made Propoxur haptens Hapten 2; Its synthetic route is as follows:
A), 2-isopropoxy-5-nitrophenyl-N-methyl carbamate is synthetic: in the 100mL three-necked flask, add the 20.9g Propoxur, the vitriol oil of 40mL, the concentrated nitric acid of 30mL, 80 ℃ of following insulation reaction 3h, reaction solution is poured in the frozen water, suction filtration, the solid ethyl alcohol recrystallization obtains needle crystal 2-isopropoxy-5-nitrophenyl-N-methyl carbamate;
B), 2-isopropoxy-5-aminophenyl-N-methyl carbamate Hapten's 1 is synthetic: take by weighing 2-isopropoxy-5-nitrophenyl-N-methyl carbamate 5.0g and be dissolved in the 50mL methyl alcohol, stir down the industrial goods Pd/C catalyzer that adds 0.5g, contains Pd quality percentage 10%, feed hydrogen, room temperature reaction 8h, suction filtration, underpressure distillation, recrystallizing methanol get tabular crystal 2-isopropoxy-5-aminophenyl-N-methyl carbamate Hapten 1;
And c), 4-[4-isopropoxy-3-(N-methyl carbamate base) anilino]-4-carbonyl butyric acid Hapten 2 synthetic: take by weighing 4.48g 2-isopropoxy-5-aminophenyl-N-methyl carbamate Hapten 1,2.1g Succinic anhydried is in reaction flask, anhydrous pyridine 100mL stirring and dissolving, N
2Protection, 50 ℃ are reacted 6h down, and the reaction solution underpressure distillation gets the field gray thick substances;
The dope NaHCO of mass concentration 10%
3The solution dissolving with dilute hydrochloric acid regulator solution pH2, is separated out cotton-shaped solid, and re-crystallizing in ethyl acetate gets white solid 4-[4-isopropoxy-3-(N-methyl carbamate base) anilino]-4-carbonyl butyric acid Hapten2.
4, the preparation method of the described Propoxur artificial antigen 1 of claim 2 is characterized in that:
Carry out the synthetic of Propoxur artificial antigen 1 by following chemical equation:
Hapten1 artificial antigen 1
Take by weighing 22.4mg Propoxur haptens Hapten1 in the flask of 50mL, add 4mL DMF dissolving, add 0.5M HCl solution 2mL and 0.1M NaNO again
2Solution 1.2mL, 4 ℃ of following stirring reaction 30min add 3.6mg urea in the flask, continue to stir 5min, get Propoxur haptens Hapten 1 diazotization component;
Taking by weighing the 240mg bovine serum albumin is dissolved in the borate buffer solution of 30mL 0.15M, pH8.7, under 4 ℃, dropwise join the diazotization component of preparation in the bovine serum albumin solution, stir 12h, afterwards coupling liquid is packed in the dialysis tubing, under 4 ℃, in the PBS of 0.01M, pH7.5 buffered soln, stir dialysis, change dialyzate every day 3 times, dialysed altogether 4-6 days, after dialysis finishes milk sap in the dialysis tubing is sub-packed in the centrifuge tube of 1mL, in-20 ℃ of refrigerators, deposits standbyly, be Propoxur artificial antigen Hapten1-BSA.
5, the preparation method of the described Propoxur artificial antigen 2 of claim 2 is characterized in that: carry out the synthetic of Propoxur artificial antigen 2 by following chemical equation:
Hapten2 artificial antigen 2
Take by weighing 17.5mg Propoxur haptens Hapten2 and join in the 50mL flask, add 1mL DMF dissolving, then add tri-n-butylamine 15.39 μ L, isobutyl chlorocarbonate 8.4 μ L, stirring reaction 1h under the room temperature gets Propoxur haptens Hapten 2 active liquid;
Taking by weighing the 100mg bovine serum albumin is dissolved in the carbonate buffer solution of 6mL 0.05M, pH9.6, and above-mentioned active drop is added in the bovine serum albumin solution, stir 2-3h under the room temperature, coupling liquid is packed in the dialysis tubing, in the PBS of 4 ℃ of following 0.01M, pH7.5 buffered soln, stir dialysis, change dialyzate every day 3 times, dialysed altogether 4-6 days, dialysis is sub-packed in transparent liquid in the dialysis tubing in the centrifuge tube of 1mL after finishing, in-20 ℃ of refrigerators, deposit standbyly, be Propoxur artificial antigen Hapten 2-BSA.
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| CN117384061A (en) * | 2023-12-11 | 2024-01-12 | 深圳市通量检测科技有限公司 | Dioxamine hapten, antigen, antibody, detection device and preparation and application thereof |
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| CN117384061A (en) * | 2023-12-11 | 2024-01-12 | 深圳市通量检测科技有限公司 | Dioxamine hapten, antigen, antibody, detection device and preparation and application thereof |
| CN117384061B (en) * | 2023-12-11 | 2024-03-15 | 深圳市通量检测科技有限公司 | Dioxamine hapten, antigen, antibody, detection device and preparation and application thereof |
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