CN101407501A - Preparation of 5-methyl morpholine-3-amino-2-oxazolidinone derivative hapten, antigen and antibody - Google Patents
Preparation of 5-methyl morpholine-3-amino-2-oxazolidinone derivative hapten, antigen and antibody Download PDFInfo
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- CN101407501A CN101407501A CNA200810219298XA CN200810219298A CN101407501A CN 101407501 A CN101407501 A CN 101407501A CN A200810219298X A CNA200810219298X A CN A200810219298XA CN 200810219298 A CN200810219298 A CN 200810219298A CN 101407501 A CN101407501 A CN 101407501A
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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 is prepared 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
The invention belongs to the immunological technique field, be specifically related to the preparation method of 5-methyl morpholine-3-amino-2-oxazolidinone derivative hapten, antigen and antibody, and the application of the 5-methyl morpholine-3-amino-2-oxazolidinone derivative hapten, antigen and antibody and the antibody that prepare.
Background technology
Furaltadone belongs to the itrofurans medicine, is Broad spectrum antibiotics, and gram-positive and negative bacterium are all had certain anti-microbial effect.But relevant studies have shown that, itrofurans medicine and metabolite thereof have sizable toxicity, the side effect of teratogenesis tire is arranged, and can bring out cancer, thereby caused people's great attention.European Union's promulgation in July nineteen ninety 2377/90/EEC regulations are classified itrofurans medicine and meta-bolites thereof as the category-A forbidden drugs, stipulate that its residue detection in animal derived food is limited to 1.0 μ g/kg.European Union provides against comprehensively and uses the furans antimicrobial substance from nineteen ninety-five, and the furans residue detects be limited to and detect in animal derived food.U.S. FDA had been announced 11 kinds of list of substance forbidding using in the import animal derived food in 2004, comprising Nifurazolidone and Furaltadone.Also the detecting be limited to and detect of Furaltadone in the regulation animal derived food sent out in the file agriculture and animal husbandry of China Ministry of Agriculture [2002] No. 1.
Because the former medicine molecule of Furaltadone metabolism soon in vivo, and protein binding attitude meta-bolites can retain the long period in tissue, so the product (AMOZ) after when analyzing this type of medicine residual, must analyzing its metabolism, the 5-methyl morpholine-3-amino-2-oxazolidinone.
Traditional 5-methyl morpholine-3-amino-2-oxazolidinone analytical procedure is to utilize materialization means qualitative, quantitatives such as chromatogram, mass spectrum, but these methods are loaded down with trivial details, instrumentation degree height and analysis speed are slow, can not satisfy in time, detect fast requirement.Advantages such as that immunological detection method has is easy, quick, sensitive, high specific are more and more paid close attention to.The internal authority academic journals are classified it as the first in recent years new analytical technology of first developing.
Most drug, toxin, environmental pollutant molecular mass be less than 1000u, belongs to only respond originality and the haptens of non-immunogenicity.At present the ordinary method of preparation small molecules hapten antibody is: select to have the meta-bolites of toxicology meaning or original shape medicine as determinand, the synthetic haptens that keeps the determinand molecular characterization and have active group of design, make haptens and the coupling of macro-molecular protein carrier by covalent linkage, the preparation artificial immunogen prepares at haptenic specific antibody through the animal immune program.
The small molecules hapten antibody for preparing all original shape medicines in theory can be realized, but also need concrete, specific technical scheme could realize the preparation of the specific antibody of medicine according to target, still the relevant report of not having at present the 5-methyl morpholine-3-amino-2-oxazolidinone haptens, antigen and the antibody that can be used for the ELISA detection makes 5-methyl morpholine-3-amino-2-oxazolidinone ELISA detection method temporarily also set up.
Summary of the invention
The objective of the invention is to overcome the deficiencies in the prior art, the preparation method of a kind of 5-methyl morpholine-3-amino-2-oxazolidinone haptens, antigen and antibody is provided.
Another object of the present invention provides 5-methyl morpholine-3-amino-2-oxazolidinone haptens, antigen and the antibody of described preparation method's preparation.
A further object of the invention provides the application of described antibody in ELISA method detection 5-methyl morpholine-3-amino-2-oxazolidinone.
Purpose of the present invention is achieved by the following technical programs:
A kind of preparation method of 5-methyl morpholine-3-amino-2-oxazolidinone derivative hapten is provided, may further comprise the steps:
(1) 5-methyl morpholine-3-amino-2-oxazolidinone and the benzaldehyde derivative of being with carboxyl are carried out the ammonium aldehyde condensation reaction at ambient temperature in methyl alcohol;
(2) wash the precipitation that obtains and obtain the target haptens.
The benzaldehyde derivative of described band carboxyl is preferably to carboxyl benzaldehyde or 2-(4-formyl radical phenoxy group) acetate.Described washing is to wash twice with water, washes twice with methyl alcohol.
The invention provides two kinds of haptens that adopt method for preparing to obtain, have structure shown in the formula (I) if the benzaldehyde derivative of band carboxyl selects that carboxyl benzaldehyde is obtained haptens (MCPAMOZ):
If selecting 2-(4-formyl radical phenoxy group) acetate to obtain haptens (CEPAMOZ), the benzaldehyde derivative of band carboxyl has structure shown in the formula (II):
By above-mentioned haptens structure as can be seen, it is similar with the corresponding body of 5-methyl morpholine-3-amino-2-oxazolidinone derivative on molecular structure, stereochemistry and electron distributions with the haptens for preparing to the present invention is directed to the design of 5-methyl morpholine-3-amino-2-oxazolidinone derivative, connecting arm in the haptens structure is not easy to induce generation " arm antibody ", and used the saturated carbon chains of certain-length, made body be easier to identification.
The invention provides the preparation method of 5-methyl morpholine-3-amino-2-oxazolidinone derivatives antigens, the coupled carrier proteins of 5-methyl morpholine-3-amino-2-oxazolidinone derivative hapten obtained artificial antigen, specifically may further comprise the steps:
(1) with 5-methyl morpholine-3-amino-2-oxazolidinone derivative hapten and N, N '-dicyclohexylcarbodiimide (DCC) and N-hydroxy thiosuccinimide (NHS) reaction form active ester;
(2) active ester is added dropwise in the protein solution, reaction is spent the night;
(3) albumen of the coupled 5-of having methyl morpholine-3-amino-2-oxazolidinone derivative hapten obtains target antigen through 3 days dialysis purifying.
The antigen that adopts haptens MCPAMOZ to obtain through method for preparing has structure shown in the formula (III):
The antigen that adopts haptens CEPAMOZ to obtain through method for preparing has structure shown in the formula (IV):
The invention provides the preparation method of 5-methyl morpholine-3-amino-2-oxazolidinone derivative antibody, with above-mentioned artificial antigen immunization experiment animal, its body is produced specifically at the antibody of 5-methyl morpholine-3-amino-2-oxazolidinone derivative, described antibody be can with the immunoglobulin G of 5-methyl morpholine-3-amino-2-oxazolidinone derivative generation specific immune response.The preparation method specifically may further comprise the steps:
(1) 5-methyl morpholine-3-amino-2-oxazolidinone derivatives antigens is cooperated good fortune formula adjuvant immunity laboratory animal;
(2) immunity is extracted blood, separation of serum after 4 times;
(3) serum obtains target antibody through the antibody purification step.
The present invention also provides the application in ELISA method detection 5-methyl morpholine-3-amino-2-oxazolidinone of described haptens, antigen and antibody, is specifically related to the preparation of coating antigen.
Compared with prior art, the present invention has following beneficial effect:
(1) the present invention is directed to 5-methyl morpholine-3-amino-2-oxazolidinone derivative designs similar with the corresponding body of 5-methyl morpholine-3-amino-2-oxazolidinone derivative on molecular structure, stereochemistry and electron distributions with the haptens of preparation, connecting arm in the haptens structure is not easy to induce generation " arm antibody ", and used the saturated carbon chains of certain-length, made body be easier to identification.Hapten molecule has to be convenient to and protein carrier link coupled active group, and the existence of active group is to the not influence of electron distributions of determinand molecule.
(2) the present invention adopts design and the coupled carrier proteins of haptens for preparing to obtain antigen, can make behind the immune body body produce the height of tiring, specificity good, at the antibody of 5-methyl morpholine-3-amino-2-oxazolidinone derivative.It is highly sensitive that described antibody is used for the immune analysis of 5-methyl morpholine-3-amino-2-oxazolidinone, and the result is stable.
Embodiment
Further describe the present invention below in conjunction with specific embodiment.
The preparation method of embodiment 1 5-methyl morpholine-3-amino-2-oxazolidinone derivative hapten MCPAMOZ
In the 50ml round-bottomed flask, add, slowly add methyl alcohol, add 0.5g 5-methyl morpholine-3-amino-2-oxazolidinone in the stirring, stirred overnight at room temperature until carboxyl benzaldehyde is dissolved fully to carboxyl benzaldehyde 1.15g.Reaction finishes to filter, washing twice, and methyl alcohol washes twice, and drying gets the 0.80g white powder, and its structural formula is shown in (I).ESI-MS(negative)m/z：332(M-H)
-.
1H?NMR(400MHz，d
5-Pyridine，TMS)：δ8.44(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)
(I)
The preparation method of embodiment 2 5-methyl morpholine-3-amino-2-oxazolidinone derivative hapten CEPAMOZ
Add 2-(4-formyl radical phenoxy group) acetate 1.06g in the round-bottomed flask, slowly add methyl alcohol, add 0.5g 5-methyl morpholine-3-amino-2-oxazolidinone in the stirring, stirred overnight at room temperature until carboxyl benzaldehyde is dissolved fully.Reaction finishes to filter, washing twice, and methyl alcohol washes twice, and drying gets the 0.93g white powder, and its structural formula is suc as formula shown in (II).ESI-MS(negative)m/z：362(M-H)
-.
1H?NMR(600MHz，d
5-Pyridine，TMS)：δ7.89-7.87(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)
The preparation method of embodiment 3 immunogen CEPAMOZ-BSA
Get haptens CEPAMOZ 0.1mmol and be dissolved among the 2ml DMF, stir adding DCC27.5mg and NHS14.4mg, 4 ℃ of lower magnetic force stirring reactions spend the night, and centrifugal back supernatant is an A liquid; Take by weighing BSA140mg and be dissolved among the PBS that 10ml concentration is 0.1mol/L (PH8.0), add DMF1ml, stirring and dissolving prepares B liquid; Under the magnetic agitation, A liquid splashes in the B liquid gradually, and 4 ℃ are reacted 12h down.After centrifugal, get supernatant, use normal saline dialysis 3d, every day to change dialyzate 3 times down for 4 ℃, the holoantigen that obtains is sub-packed in 0.5ml with the concentration of 1mg/ml
In the centrifuge tube, frozen in-20 ℃ of refrigerators, use for immunity.The 5-methyl morpholine-3-amino-2-oxazolidinone derivative immunogen CEPAMOZ-BSA structure of preparation is shown in formula V:
Immunogen is identified: to carrier proteins BSA, haptens CEPAMOZ and immunogen CEPAMOZ-BSA carry out UV scanning and measure (200～400nm), find that immunogen CEPAMOZ-BSA compares with haptens IV with BSA, absorption curve has obvious change, and the coupled success of haptens CEPAMOZ and BSA is described.The coupled ratio that trinitrobenzene yellow acid method (TNBS) records haptens IV and BSA is 15: 1.
The preparation method of embodiment 4 coating antigen CEPAMOZ-OVA
Get haptens CEPAMOZ 0.1mmol and be dissolved among the 2ml DMF, stir adding DCC27.5mg and NHS 14.4mg.4 ℃ of lower magnetic force stirring reactions spend the night, and centrifugal back supernatant is an A liquid, takes by weighing OVA 140mg and is dissolved among the PBS that 10ml concentration is 0.1mol/L (PH8.0).Add DMF 1ml, stirring and dissolving prepares B liquid, and under the magnetic agitation, A liquid splashes in the B liquid gradually, and 4 ℃ are reacted 12h down.After centrifugal, get supernatant, use normal saline dialysis 3d, every day to change dialyzate 3 times down for 4 ℃.The holoantigen that obtains is sub-packed in the 0.5ml centrifuge tube with the concentration of 1mg/ml.Frozen in-20 ℃ of refrigerators, used for bag.
The coating antigen CEPAMOZ-OVA structure of preparation is suc as formula shown in (VI):
Coating antigen is identified: to carrier proteins OVA, haptens CEPAMOZ and coating antigen CEPAMOZ-OVA carry out UV scanning and measure (200～400nm), find that coating antigen CEPAMOZ-OVA compares with carrier proteins OVA and haptens CEPAMOZ, absorption curve has obvious change, and haptens CEPAMOZ and the coupled success of carrier proteins OVA are described.The coupled ratio that the TNBS method records haptens CEPAMOZ and carrier proteins OVA is 12: 1.
Embodiment 5 Polyclonal Antibody Preparation methods and antibody titer are measured
Polyclonal Antibody Preparation: immunogen is slowly thawed, after adding the complete emulsification of adjuvant of equivalent then, adopt that the back is subcutaneous, each position is subcutaneous, leg muscle and 6 healthy new zealand white rabbits that body weight is 2.5～3kg of the multiple injection system immunity of auricular vein, Freund's complete adjuvant is used in the 1st immunity, and later booster immunization is all used Freund's incomplete adjuvant.1 all ear edge vein exploitating bloods behind the 4th booster immunization, and utilize indirect ELISA to measure serum titer.When no longer rising, adopt the auricular vein immune rabbit when tiring.The back heart blood sampling of 1 week, room temperature leaves standstill 0.5～1h, draws the serum that separate out on the upper strata after 4 ℃ of refrigerator overnight.Antiserum(antisera) adopts the ammonium sulfate precipitation method purifying to obtain polyclonal antibody, and dialysis postlyophilization powdered is preserved standby down in-20 ℃.
The detection of antibody titer: indirect competitive ELISA is measured the antibody positive titre and is as the criterion with 2.1 times of measured values to negative serum, and the positive titre that records antibody is 1: 1280000.
Embodiment 6 antibody affinities and specificity test
The derivative NPAMOZ of the Ortho Nitro Benzaldehyde of the 5-methyl morpholine-3-amino-2-oxazolidinone of different concns is carried out the indirect competitive ELISA reaction with antibody, measure its inhibiting rate, to determine the affinity of antibody to NPAMOZ.Its IC
50Be 0.5ng/mL.
NPAMOZ (the nitrobenzoyl aldehyde condensate of AMOZ), Ortho Nitro Benzaldehyde, phenyl aldehyde, oil of mirbane, NPAOZ (the nitrobenzoyl aldehyde condensate of AOZ), NPAHD (the nitrobenzoyl aldehyde condensate of AHD) and NPSEM (the nitrobenzoyl aldehyde condensate of SEM) are made into different concns solution, measure its cross reacting rate, found that and similar medicine no cross reaction, see Table 1.
Advantages such as the antibody that above experimental result explanation immunity produces has highly sensitive, and specificity is good.
Table 1 cross reaction test-results
Claims (8)
1, a kind of preparation method of 5-methyl morpholine-3-amino-2-oxazolidinone derivative hapten is characterized in that may further comprise the steps:
(1) 5-methyl morpholine-3-amino-2-oxazolidinone and the benzaldehyde derivative of being with carboxyl are carried out the ammonium aldehyde condensation reaction at ambient temperature in methyl alcohol;
(2) wash the precipitation that obtains and obtain the target haptens.
2, the 5-methyl morpholine-3-amino-2-oxazolidinone derivative hapten for preparing of the described preparation method of a kind of claim 1, the structure shown in (I) that it is characterized in that having formula:
3, the 5-methyl morpholine-3-amino-2-oxazolidinone derivative hapten for preparing of the described preparation method of a kind of claim 1, the structure shown in (II) that it is characterized in that having formula:
4, a kind of preparation method of 5-methyl morpholine-3-amino-2-oxazolidinone derivatives antigens prepares the coupled carrier proteins of 5-methyl morpholine-3-amino-2-oxazolidinone derivative hapten, it is characterized in that may further comprise the steps:
(1) with 5-methyl morpholine-3-amino-2-oxazolidinone derivative hapten and N, N '-dicyclohexylcarbodiimide and the reaction of N-hydroxy thiosuccinimide form active ester;
(2) active ester is added dropwise in the protein solution, reaction is spent the night;
(3) albumen of the coupled 5-of having methyl morpholine-3-amino-2-oxazolidinone derivative hapten obtains target antigen through 3 days dialysis purifying.
5, the 5-methyl morpholine-3-amino-2-oxazolidinone derivatives antigens for preparing of the described preparation method of a kind of claim 4, the structure shown in (III) that it is characterized in that having formula:
6, the 5-methyl morpholine-3-amino-2-oxazolidinone derivatives antigens for preparing of the described preparation method of a kind of claim 4, the structure shown in (IV) that it is characterized in that having formula:
7, a kind of preparation method of 5-methyl morpholine-3-amino-2-oxazolidinone derivative antibody is characterized in that may further comprise the steps:
(1) 5-methyl morpholine-3-amino-2-oxazolidinone derivatives antigens is cooperated freund's adjuvant immunization experiment animal;
(2) immunity is extracted blood, separation of serum after 4 times;
(3) serum obtains target antibody through antibody purification.
8, the antibody for preparing of the described preparation method of a kind of claim 7 detects application in the 5-methyl morpholine-3-amino-2-oxazolidinone in the ELISA method.
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