CN102040661A - Artificial antigen and specific antibody of veterinary drug penicillin G degradation product benzylpenicilloic thiazole acid - Google Patents
Artificial antigen and specific antibody of veterinary drug penicillin G degradation product benzylpenicilloic thiazole acid Download PDFInfo
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- CN102040661A CN102040661A CN2009100708673A CN200910070867A CN102040661A CN 102040661 A CN102040661 A CN 102040661A CN 2009100708673 A CN2009100708673 A CN 2009100708673A CN 200910070867 A CN200910070867 A CN 200910070867A CN 102040661 A CN102040661 A CN 102040661A
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Abstract
An artificial antigen and an antibody of a veterinary drug penicillin G degradation product benzylpenicilloic thiazole acid and preparation method thereof. The invention relates to the preparation of a hapten, an artificial antigen and an antibody of benzylpenicilloic thiazole acid having a structure of (2S, 5R, 6R)-3,3-dimethyl-6-(2-pheylacetamino)-7-oxo-4-thia-1-azabicyclo[3,2,0]heptane-2-formic acid and their application in the establishment of immunoassay. The invention solves the problem that traditional physical and chemical analysis methods are complicated, high in cost and slow in analysis, and provides a simple, quick, sensitive and accurate immunoassay technique. According to the invention, (2S, 5R, 6R)-3,3-dimethyl-6-(2-pheylacetamino)-7-oxo-4-thia-1-azabicyclo[3,2,0]heptane-2-formic acid is adopted as a hapten, and the haptens are linked with KLH and HRP respectively to synthesize artificial antigens and enzyme-labeled antigens. The antibody is prepared by animal immunization, blood drawing, antiserum separation, and purification of artificial antigen. The antibody is stable and has good specificity and sensitivity; the synthetic method is simple; the invention is applicable to the rapid immunoassay of veterinary drug penicillin G degradation product benzylpenicilloic thiazole acid, and has a good application prospect.
Description
Technical field
The invention belongs to micromolecular compound (molecular weight is less than 1000 dalton) immunochemistry and retention analysis technical field; Relate to organic synthesis, immunochemistry, biological chemistry and materialization measuring technology etc.; Be particularly related to have the penicillins veterinary drug penicillin G degradation product benzyl penicilloic acid micromolecular compound artificial semiantigen that relates to the heterocycle molecular structure that has hydrogenation thiazole ring and beta-lactam nucleus and close, the design of specific antigens is synthetic.
Background technology
Penicillin G (also claiming penicillin G) is a kind of of Penicillin antibiotics, and Penicillin antibiotics is to enter a clinical application class microbiotic the earliest, also is China's turnout maximum, microbiotic that usage quantity is maximum.Penicillin antibiotics has become treatment milk cow and the most frequently used medicine of other edibility Animal diseases, but because medication lack of standardization and that the milk sample is collected is improper, causes in the animal derived food penicillin medicine residual phenomena serious.Penicillin medicine is residual in vivo can to produce severe anaphylactic reaction, and the anaphylaxis rate is in first of the various kinds of drug.Because penicillin easily is degraded to penicilloic acid under the β-Nei Xiananmei effect, make penicillin lose anti-microbial activity, it is residual that this makes conventional detection can't detect penicillin, encouraged the abuse of β-Nei Xiananleikangshengsu in the milk-producing more, quickened the propagation of resistant organism, serious threat the long-run development of Chinese milk industry.For this reason, to the residual restriction of penicillin also so more and more stricter, and, new requirement and higher standard are proposed all to aspects such as assay determination object, kind, quantity, scope, indexs.The animal food herbal medicine maximum residue limit(MRL) of the Ministry of Agriculture's issue, regulation to penicillin G: muscle≤50 μ g/kg, fat≤50 μ g/kg, liver≤50 μ g/kg, kidney≤50 μ g/kg, milk≤4 μ g/kg, though the benzyl penicilloic acid is not made respective specified, its harm that causes can not be ignored.Molecular weight is less than 1000 daltonian small molecules noxious chemicals, and as agricultural chemicals, veterinary drug and meta-bolites thereof, its traditional retention analysis mainly is to rely on analysis means such as gas-chromatography, liquid chromatography or chromatograph-mass spectrometer coupling.These physico-chemical analysis methods, very complicated, cost is higher, analysis speed is slow, is difficult to satisfy the needs of actual analysis, therefore presses for easy, quick, the sensitive analytical technology of exploitation.
But different with macromole, the micromolecular compound immunoassay has own characteristic:
(1) micromolecular compound (MW≤1000dolton) does not generally have immunogenicity, can not produce specific antibody, must synthesize the haptens at outstanding molecule stereo structure specificity position by the direct immunization animal, and connect and compose joiner with macromolecular carrier, could immune animal produce specific antibody at this target micromolecular compound.The binding substances of this haptens and macromolecular carrier is called artificial antigen.The preparation of artificial antigen is not arbitrarily, comprise that difference on binding site, combination, kind of carrier and haptens and the target analytes any structure is as the factors of size, shape, composition, configuration, conformation, polarity, cloud density or the like, all may greatly affect the character of corresponding antibodies, so they are that decision produces its specific antibody and the key of setting up immune analysis method.
(2) though micromolecular compound does not have immunogenicity, have reactionogenicity, promptly have the ability with corresponding antibodies generation immunological response, and can externally quantitatively carry out, follow the law of mass action.
(3) based on the analytical technology of antigen-antibody immune response detection small molecules platform thing, adopt enzyme immunoassays (ELISA) at present more.Utilize the quantitative combination of enzymatic reaction demonstration antigen-antibody, simple to operate, have suitable sensitivity again, development in recent years is very fast.Veterinary drug ELISA that has grown up since the eighties and simple and easy enzyme immunity EIA technology make the residue of veterinary drug analysis obtain bigger vitality on method; Too complicated to using real-time analysis sample matrix, with the residue of veterinary drug that common physico-chemical method is difficult to analyze, have suitable using value.
Immuno analytical method is introduced into residue of veterinary drug and divides the folding field, becomes one of a kind of quantitative analysis tech that development and application potential are arranged most, is subjected to paying attention to widely.The key of this technical study is the preparation of haptenic molecular designing, synthetic and artificial holoantigen and antibody.Therefore, target analytes molecular immunology characteristic, and how outstanding and utilize these characteristics by chemistry or biochemical technology, be the important research contents in this field.This technology has become a brand-new field of trace analysis research at present, can with the traditional analysis method side by side as a new analysis approach.
Micromolecular compound (molecular weight is less than 1000 dalton) relies on immunology, immunochemistry ultimate principle and biotechnology means.The key of this technical study is the preparation of haptenic molecular designing, synthetic and artificial holoantigen and antibody.Therefore, target analytes molecular immunology characteristic, and how outstanding and utilize these characteristics by chemistry or biochemical technology, be the important research contents in this field.This technology has become a brand-new field of trace analysis research at present, can with the traditional analysis method side by side as a new analysis approach.Penicillin G and degradation product benzyl penicilloic acid artificial antigen thereof do not appear in the newspapers as yet at present.
Summary of the invention
The problem in science that needs solution: at above-mentioned situation, a kind of simple and easy method that fast and effeciently detects penicillin G and degradation product benzyl penicilloic acid thereof of current urgent need.The objective of the invention is by designing synthetic haptens and artificial antigen with penicillins veterinary drug penicillin G and degradation product benzyl penicilloic acid thereof of 6-aminocaprolc acid molecular structure and beta-lactam nucleus molecular structure, preparation is at the specific antibody of penicillin G and degradation product benzyl penicilloic acid thereof; Unique distinction is to have given prominence to this class veterinary drug molecular specificity antigenic determinant, has overcome the difficulty of chemosynthesis again, and immune animal is induced and produces the very high specific antibody of affinity.
Technical scheme
The present invention design, synthesized the haptens of small molecules target analytes, and with the carrier protein coupling, prepare effective artificial antigen, the immune animal preparation is at the specific antibody of small molecules analyte.Its selectivity is decided by the specificity of immunological response, can be to set up fast and accurately penicillin G and the residual quantitative analysis method of degradation product benzyl penicilloic acid lays the foundation.The key of this technical study is the preparation of haptenic molecular designing, synthetic and artificial holoantigen.
Benzyl penicilloic acid structure is as shown below:
The molecular structure of benzyl penicilloic acid can be divided into two structural units: a part is a penicilloyl, and a part is the benzyl side chain.The space structure complexity of benzyl side chain and penicilloyl, molecular weight is bigger, can be used as antigenic determinant, and the carboxyl on the hydrogenation thiazole ring can connect by carrier proteins.Therefore when synthesizing haptens, must keep base side chain and penicilloyl structure, utilize the carboxyl on the hydrogenation thiazole ring to be connected therefore with carrier proteins, it is 334 structures (2S as shown below that the present invention selects molecular weight MW, 5R, 6R)-3,3-dimethyl-6-(2-phenylacetylamino)-7-oxo-4-thia-1-azabicyclo [3,2,0] heptane-2-formic acid is haptens
The synthetic molecules formula that is connected with keyhole limpet hemocyanin is
Compound be artificial antigen, connect synthetic enzyme-labelled antigen with horseradish peroxidase.Artificial antigen obtains antibody through immune animal.
Specific practice is:
Get (2S, 5R, 6R)-3,3-dimethyl-6-(2-phenylacetylamino)-7-oxo-4-thia-1-azabicyclo [3,2,0] heptane-2-formic acid sylvite 1.500g, add 4.0ml 1M hydrochloric acid, obtain haptens (2S, 5R, 6R)-3,3-dimethyl-6-(2-phenylacetylamino)-7-oxo-4-thia-1-azabicyclo [3,2,0] heptane-2-formic acid white solid, distilled water washing and drying can obtain haptens.
Getting gained white solid 0.5000g is dissolved in the 2ml tetrahydrofuran (THF), add 0.1500gN-N-Hydroxysuccinimide and 0.5000gN, the N-dicyclohexylcarbodiimide, under 22-25 ℃, stirring reaction spends the night, be put in 4 ℃ of refrigerators then interior 18 hours, the centrifugal precipitation of removing, upper strata Acibenzolar liquid is joined pH 7.0 to be dissolved with in the 2mlPBS solution of 10mg keyhole limpet hemocyanin, after stirring, reacted 5 hours down in 4 ℃, with the reaction solution dialysis tubing of packing into, under 4 ℃, dialysis can obtain artificial antigen in three days in the PBS of pH 7.4.
Get the synthetic haptens 1.9mg of institute and be dissolved in 2ml dimethyl formamide wiring solution-forming A, 0.54mg horseradish peroxidase is dissolved in wiring solution-forming B in the 0.2mol/L phosphoric acid buffer of 2ml pH 7.4, under ice bath, add solution A in the solution B slowly then, reaction is spent the night under 4 ℃ after stirring, at last reaction solution is inserted in the dialysis tubing, 0.2mol/L phosphoric acid buffer dialysis with pH7.4 under 4 ℃ can obtain enzyme-labelled antigen in three days, was used for color reaction.
The preparation method of veterinary drug penicillin G degradation product benzyl penicilloic acid antibody:
Immune animal is selected female new zealand white rabbit for use, immunization method adopts subcutaneous and intramuscular injection, carry out booster immunization after just exempting from four times, booster immunization respectively at initial immunity after 2 weeks, 4 weeks and 6 week back immunity three times, after this interval is one month, carries out the 5th immunity, gets blood by the auricular vein of rabbit after 9 days, the detection of tiring, specific practice is:
Initial immunity: get 1mg and be dissolved in the solution that 0.9% NaCl solution and Freund's complete adjuvant equal-volume prepared, carry out animal immune according to the described method synthetic of claim 3 artificial antigen;
Booster immunization: be dissolved in the solution that 0.9% NaCl solution and Freund's incomplete adjuvant equal-volume are prepared with the above-mentioned artificial antigen of 0.5mg, carry out animal immune;
Antibody purification: the periodic monitor animal's antibody is tired, when antibody reaches suitable tiring to certain envelope antigen, gather blood, and centrifugal acquisition antiserum(antisera), use G-Sepharose albumen affinity column antagonistic Serum to carry out purifying, obtain the specific antibody of anti-veterinary drug penicillin G degradation product benzyl penicilloic acid.
Beneficial effect
Compare characteristics such as that the present invention has is special, sensitive, accurate, quick, convenient, cheapness with class methods with other.This design, synthetic haptens and target determinand similarity degree height, complete to the feature structure reservation of determinand, for the good antibody of preparation specificity is laid a good foundation.
Through verification experimental verification, above-mentioned haptens, its simple synthetic method, and used main raw material (2S, 5R, 6R)-3,3-dimethyl-6-(2-phenylacetylamino)-7-oxo-4-thia-1-azabicyclo [3,2,0] heptane-2-formic acid sylvite, comparatively cheap, the easy acquisition of 6-aminocaprolc acid price all can be bought in general chemical reagents corporation.Because combined coefficient height, reactions steps are few, haptens only needs single step reaction to synthesize, thereby has improved the controllability of reaction, and reaction yield has reached 96% and 86% respectively.In addition, extraction, the purification process of synthetic product are easy, only need carry out acid precipitation to synthetic product, can obtain highly purified purpose product.Therefore, the synthetic haptenic method of the present invention is compared with additive method, is easy to more popularize.
Embodiment
Embodiment 1:
The preparation method of benzyl penicilloic acid artificial antigen
With (2S, 5R, 6R)-3,3-dimethyl-6-(2-phenylacetylamino)-7-oxo-4-thia-1-azabicyclo [3,2,0] heptane-2-formic acid, with amide group CO=NH is bridge, by active ester method connect hemocyanin (keyhole limpet hemocyanin, KLH) on, synthetic artificial antigen; Specific practice is:
Get 1.5mg (2S, 5R, 6R)-3,3-dimethyl-6-(2-phenylacetylamino)-7-oxo-4-thia-1-azabicyclo [3,2,0] heptane-2-formic acid sylvite adds 4.0ml 1M hydrochloric acid, obtains haptens (2S, 5R, 6R)-3,3-dimethyl-6-(2-phenylacetylamino)-7-oxo-4-thia-1-azabicyclo [3,2,0] heptane-2-formic acid white solid, distilled water washing and drying can obtain haptens.
Getting gained white solid 0.5000g is dissolved in the 2ml tetrahydrofuran (THF), add 0.1500gN-N-Hydroxysuccinimide and 0.5000gN, the N-dicyclohexylcarbodiimide, under 22-25 ℃, stirring reaction spends the night, be put in 4 ℃ of refrigerators then interior 18 hours, the centrifugal precipitation of removing, upper strata Acibenzolar liquid is joined pH 7.0 to be dissolved with in the 2mlPBS solution of 10mg keyhole limpet hemocyanin, after stirring, reacted 5 hours down in 4 ℃, with the reaction solution dialysis tubing of packing into, under 4 ℃, dialysis can obtain artificial antigen in three days in the PBS of pH 7.4.
Embodiment 2:
The preparation method of veterinary drug penicillin G degradation product benzyl penicilloic acid antibody
Immune animal is selected female new zealand white rabbit for use, immunization method adopts subcutaneous and intramuscular injection, carry out booster immunization after just exempting from four times, booster immunization respectively at initial immunity after 2 weeks, 4 weeks and 6 week back immunity three times, after this interval is one month, carries out the 5th immunity, gets blood by the auricular vein of rabbit after 9 days, the detection of tiring, specific practice is:
Initial immunity: get 1mg and be dissolved in the solution that 0.9% NaCl solution and Freund's complete adjuvant equal-volume prepared, carry out animal immune according to the described method synthetic of claim 3 artificial antigen;
Booster immunization: be dissolved in the solution that 0.9% NaCl solution and Freund's incomplete adjuvant equal-volume are prepared with the above-mentioned artificial antigen of 0.5mg, carry out animal immune;
Antibody purification: the periodic monitor animal's antibody is tired, when antibody reaches suitable tiring to certain envelope antigen, gather blood, and centrifugal acquisition antiserum(antisera), use G-Sepharose albumen affinity column antagonistic Serum to carry out purifying, obtain the specific antibody of anti-veterinary drug penicillin G degradation product benzyl penicilloic acid.
Claims (5)
1. veterinary drug penicillin G degradation product benzyl penicilloic acid artificial antigen and antibody is characterized in that using molecular formula to be
(2S, 5R, 6R)-3,3-dimethyl-6-(2-phenylacetylamino)-7-oxo-4-thia-1-azabicyclo [3,2,0] heptane-2-formic acid is connected synthetic artificial antigen as haptens with keyhole limpet hemocyanin, be connected synthetic enzyme-labelled antigen with horseradish peroxidase, wherein artificial antigen passes through immune new zealand white rabbit again, gets blood, isolates the antiserum(antisera) purifying and makes antibody;
2. the haptenic preparation method of the described veterinary drug penicillin G of claim 1 degradation product benzyl penicilloic acid, it is characterized in that it being to make: get (2S with following step, 5R, 6R)-3,3-dimethyl-6-(2-phenylacetylamino)-7-oxo-4-thia-1-azabicyclo [3,2,0] heptane-2-formic acid sylvite 1.500g adds 4.0ml 1M hydrochloric acid, obtains haptens (2S, 5R, 6R)-3,3-dimethyl-6-(2-phenylacetylamino)-7-oxo-4-thia-1-azabicyclo [3,2,0] heptane-2-formic acid white solid, distilled water washing and drying can obtain haptens;
3. the preparation method of the described veterinary drug penicillin G of claim 1 degradation product benzyl penicilloic acid artificial antigen, it is characterized in that it being to make with following step: the weighting profit requires 2 gained white solid 0.5000g to be dissolved in the 2ml tetrahydrofuran (THF), add 0.1500gN-N-Hydroxysuccinimide and 0.5000gN, the N-dicyclohexylcarbodiimide, under 22-25 ℃, stirring reaction spends the night, be put in 4 ℃ of refrigerators then interior 18 hours, the centrifugal precipitation of removing, upper strata Acibenzolar liquid is joined pH 7.0 to be dissolved with in the 2mlPBS solution of 10mg keyhole limpet hemocyanin, after stirring, reacted 5 hours down in 4 ℃, with the reaction solution dialysis tubing of packing into, under 4 ℃, dialysis can obtain artificial antigen in three days in the PBS of pH 7.4;
4. the preparation method of the described veterinary drug penicillin G of claim 1 degradation product benzyl penicilloic acid enzyme-labelled antigen, it is characterized in that it being to make with following step: the weighting profit requires 2 synthetic haptens 1.9mg to be dissolved in 2ml dimethyl formamide wiring solution-forming A, 0.54mg horseradish peroxidase is dissolved in wiring solution-forming B in the 0.2mol/L phosphoric acid buffer of 2ml pH 7.4, under ice bath, add solution A in the solution B slowly then, reaction is spent the night under 4 ℃ after stirring, at last reaction solution is inserted in the dialysis tubing, 0.2mol/L phosphoric acid buffer dialysis with pH7.4 under 4 ℃ can obtain enzyme-labelled antigen in three days, was used for color reaction;
5. the preparation method of the described veterinary drug penicillin G of claim 1 degradation product benzyl penicilloic acid antibody is characterized in that it being to make with following step:
Immune animal is selected female new zealand white rabbit for use, immunization method adopts subcutaneous and intramuscular injection, carry out booster immunization after just exempting from four times, booster immunization respectively at initial immunity after 2 weeks, 4 weeks and 6 week back immunity three times, after this interval is one month, carries out the 5th immunity, gets blood by the auricular vein of rabbit after 9 days, the detection of tiring, specific practice is:
Initial immunity: get 1mg and be dissolved in the solution that 0.9% NaCl solution and Freund's complete adjuvant equal-volume prepared, carry out animal immune according to the described method synthetic of claim 3 artificial antigen;
Booster immunization: be dissolved in the solution that 0.9% NaCl solution and Freund's incomplete adjuvant equal-volume are prepared with the above-mentioned artificial antigen of 0.5mg, carry out animal immune;
Antibody purification: the periodic monitor animal's antibody is tired, when antibody reaches suitable tiring to certain envelope antigen, gather blood, and centrifugal acquisition antiserum(antisera), use G-Sepharose albumen affinity column antagonistic Serum to carry out purifying, obtain the specific antibody of anti-veterinary drug penicillin G degradation product benzyl penicilloic acid.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103483445A (en) * | 2013-10-08 | 2014-01-01 | 天津科技大学 | Preparation methods and applications of benzylpenicilloic acid artificial antigen and benzylpenicilloic acid artificial antibody |
| CN104569326A (en) * | 2013-10-23 | 2015-04-29 | 上海捷门保林迈生物工程有限公司 | Method for detecting beta-lactamase in milk and test paper |
| CN104614529A (en) * | 2015-01-14 | 2015-05-13 | 北京农学院 | Ampicillin penicilloic acid detection kit and detection method |
| CN104764878A (en) * | 2015-03-06 | 2015-07-08 | 天津科技大学 | An immunocolloidal gold test strip for detecting penicilloic acid and a preparing method thereof |
| CN107904210A (en) * | 2017-12-27 | 2018-04-13 | 江南大学 | One plant of procaine monoclonal antibody hybridoma cell strain 4G6 and its application |
-
2009
- 2009-10-19 CN CN2009100708673A patent/CN102040661A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103483445A (en) * | 2013-10-08 | 2014-01-01 | 天津科技大学 | Preparation methods and applications of benzylpenicilloic acid artificial antigen and benzylpenicilloic acid artificial antibody |
| CN104569326A (en) * | 2013-10-23 | 2015-04-29 | 上海捷门保林迈生物工程有限公司 | Method for detecting beta-lactamase in milk and test paper |
| CN104614529A (en) * | 2015-01-14 | 2015-05-13 | 北京农学院 | Ampicillin penicilloic acid detection kit and detection method |
| CN104764878A (en) * | 2015-03-06 | 2015-07-08 | 天津科技大学 | An immunocolloidal gold test strip for detecting penicilloic acid and a preparing method thereof |
| CN107904210A (en) * | 2017-12-27 | 2018-04-13 | 江南大学 | One plant of procaine monoclonal antibody hybridoma cell strain 4G6 and its application |
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Application publication date: 20110504 |