CN101328204A - Preparation of dioctyl phthalate artificial antigen - Google Patents
Preparation of dioctyl phthalate artificial antigen Download PDFInfo
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- CN101328204A CN101328204A CNA2008100222444A CN200810022244A CN101328204A CN 101328204 A CN101328204 A CN 101328204A CN A2008100222444 A CNA2008100222444 A CN A2008100222444A CN 200810022244 A CN200810022244 A CN 200810022244A CN 101328204 A CN101328204 A CN 101328204A
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Abstract
The invention relates to a method for preparing a dioctylphthalate artificial antigen, belonging to the biochemical technical field. The method comprises the following steps that: 4-nitroisophthalic acid is taken as a raw material and generates esterification reaction with n-octanol under the catalysis of concentrated sulfuric acid, and then a hapten is prepared by utilization of the ferrous powder reaction method to reduce nitryl on a benzene ring of dioctylphthalate into amido; and the artificial antigen of the dioctylphthalate, namely dioctylphthalate-bovine serum albumin, is prepared by utilization of the diazotization method to perform diazotization on the amido on the hapten and make the hapten combined with bovine serum albumin. The method synthesizes the artificial antigen of the dioctylphthalate, has concise and effective synthetic procedures, can be completely used for immunoassay, provides convenience for the future research, and can meet the demand of domestic research of the dioctylphthalate artificial antigen.
Description
Technical field
A kind of preparation method of dioctyl phthalate artificial antigen belongs to technical field of biochemical industry.
Background technology
(Dioctylphthalate DOP) is a kind of of phthalate to dioctyl phthalate (DOP).Phthalate is especially used in the processing of polyvinyl chloride (PVC) in processing of plastic is produced widely as softening agent.Owing to do not form covalent linkage between phthalate softening agent and the plastics substrate, but be connected with Van der Waals force with hydrogen bond, maintenance chemical property independently separately each other, thereby in touching wrap food when contained water, grease, just can stripping.Through discovering, phthalate is a kind of environmental hormone material, it disturbs biological is generation, release, transfer, metabolism, reaction and the elimination that keeps the normal hormone of homeostasis and modulated growth processes, or causes the bad healthy effect and the change of endocrine function in int biological offspring.EPA is listed six kinds of phthalates in the pollutent list of emphasis control in, comprises dioctyl phthalate (DOP) in China's priority pollutant Black List.At present, high performance liquid chromatography (HPLC), vapor-phase chromatography (GC), gas-matter coupling method (GC-MS), liquid-matter coupling method (LC-MS) etc. are mainly adopted in the detection of relevant dioctyl phthalate (DOP) both at home and abroad, it needs expensive plant and instrument though these methods are sensitive, the operator of specialty, to the requirement of sample also than higher, and need further sample pre-treatment just can carry out, this can not reach modern and detect quick, convenient, requirement accurately.In recent years, carried out the research of terephthalic acid ester para-immunity analytical procedure both at home and abroad, but still do not have report both at home and abroad,, be necessary to prepare dioctyl phthalate artificial antigen in order to remedy this blank at the enzyme linked immunosorbent detection of dioctyl phthalate (DOP).
Summary of the invention
The preparation method who the purpose of this invention is to provide a kind of dioctyl phthalate artificial antigen, prepared product can be used for the research of dioctyl phthalate (DOP) immune analysis method, for people's research from now on provides approach easily.
Technical scheme of the present invention: the first step is haptenic preparation and detection, with the 4-nitrophthalic acid is raw material, under the catalysis of the vitriol oil,, utilize the iron powder reducing method to make the nitroreduction on the 4-nitrophthalic acid dioctyl ester phenyl ring be amido then with n-Octanol generation esterification; Second step utilized the diazotization method amido to be carried out diazotization and make it combining with bovine serum albumin (BSA) for artificial antigenic preparation and detection, the artificial antigen of preparation dioctyl phthalate (DOP).Its reaction equation is:
Processing step is:
(1) preparation of artificial semiantigen:
1. 4-nitrophthalic acid dioctyl ester is synthetic
The 4-nitrophthalic acid that takes by weighing 0.12mol is in the three-necked flask of 100mL, adding 0.1mol is the n-Octanol of 15.74mL, add a certain amount of benzene hydrotropy, under stirring condition, the vitriol oil that slowly adds 1.6mL, heat temperature raising react 7-24h to 110-130 ℃, the pressure reducing and steaming organic solvent, the residual Na that uses mass concentration 10% in the cold water that joins of oily
2CO
3It is colourless that solution is washed till lower aqueous layer, gets the upper strata and obtain bolarious oily crude product, carries out recrystallization with dehydrated alcohol, obtains the 4-nitrophthalic acid dioctyl ester of 45mmol;
Thin layer chromatography detects: 1cm place, silica gel thin sheet lower end makes a sea line, draws reaction solution 1 μ L point on line, and point sample dries up after finishing, thin plate is put into chromatography cylinder, and chromatographic solution is an acetate: the normal hexane volume ratio is 1: 15, is expanded to thin plate 3/4 place, get plate, dry up solvent; Thin plate being placed uv analyzer, observe at the 254nm wavelength, is that 0.74 place observes the colour developing point as reaction end at Rf;
2. 4-aminophthalic acid dioctyl ester is synthetic
Take by weighing the 9mmol reduced iron powder in the 50mL round-bottomed flask, add 10mL water, 3mmol ammonium chloride, heat 15min in the water-bath; Other takes by weighing 4-nitrophthalic acid dioctyl ester 3mmol, behind a certain amount of dissolve with methanol, divides to add in the middle of the above-mentioned reaction solution back flow reaction 4-6h for 3 times; The filtered while hot iron powder carries out underpressure distillation with filtrate, and it is standby as haptens that the orange red residual small amount of thermal dissolve with methanol solution of using that obtains, low temperature are separated out the 4-aminophthalic acid dioctyl ester of 1.17mmol orange oily liquids;
Thin layer chromatography detects: 1cm place, silica gel thin sheet lower end makes a sea line, draws reaction solution 1 μ L point on line, and point sample dries up after finishing, thin plate is put into chromatography cylinder, and chromatographic solution is an acetate: the normal hexane volume ratio is 1: 15, is expanded to thin plate 3/4 place, get plate, dry up solvent; Thin plate being placed uv analyzer, observe at the 254nm wavelength, is that 0.52 place observes the colour developing point as reaction end at Rf;
(2) preparation of artificial antigen:
1. prepare A liquid: get the 0.023mmol haptens in the 25mL beaker, the 1mol/L hydrochloric acid that adds 2mL dimethyl formamide, 0.2mL water and 0.2mL, form yellow solution, be cooled to 0-5 ℃, progressively drip the 1mol/L sodium nitrite solution then,, become pewter up to test paper and stop to drip with the starch potassium iodide paper monitoring, 4 ℃ are stirred 1h down, and this liquid is A liquid;
2. prepare B liquid: the bovine serum albumin that takes by weighing 150mg is dissolved in pH 9.0 borate buffer solutions of 6mL, 4 ℃ of preservations, and this liquid is B liquid;
3. under 4 ℃ of stirrings, A liquid dropwise is added drop-wise in the B liquid, and regulates pH with the sodium hydroxide solution of 1mol/L, pH is remained under 9,4 ℃, stirring is spent the night, and promptly obtains the artificial antigen mixed solution;
4. the artificial antigen mixed solution is moved in the dialysis tubing, dialysed 4-6 days with the deionized water of 6 * 1L; Use lyophilization that the liquid in the dialysis tubing is made powder at last, promptly obtain artificial antigen: dioctyl phthalate (DOP)-bovine serum albumin.
Dialysis tubing pre-treatment: get the dialysis tubing of 10cm, boil 5min, use 60 ℃ deionized water rinsing 3min again, be kept in 4 ℃ of deionized waters standby.
(3) evaluation of dioctyl phthalate artificial antigen: protein concentration and the coupling ratio of measuring conjugate.
The conjugate determination of protein concentration: compound concentration is 0,40,60,80,100,120,160,200 μ gmL
-1Each 1.5mL of bovine serum albumen solution, add 5mL coomassie brilliant blue staining liquid, mixing immediately, warm 5 minutes of 30 ℃ of water-baths, each concentration is made parallel sample. survey light absorption value, the relation curve of drafting protein concentration and light absorption value at 595nm place.Antigenic solution is diluted by a certain percentage, measure the light absorption value of antigenic solution at the 595nm place, obtain the corresponding proteins concentration of antigenic solution from curve.It is 7.67mgmL that this experimental calculation gets the conjugate protein concentration
-1
Coupling ratio is measured: adopt the spectrophotometry coupling ratio.Spectrophotometry is to utilize material that the principle that absorption and its concentration of light is proportionlity is measured respectively by two kinds of molecular conecentrations of link coupled, in macromole and small molecules conjugate, two kinds of molecules have different separately ultraviolet scanning spectrums, and show the character of spectrogram superposition.
Molar absorption coefficient ε: preparation 4-aminophthalic acid dioctyl ester concentration is 0,10,20,30 μ gmL
-120% ethanolic soln, by UV scanning as can be known the maximum absorption wavelength of 4-aminophthalic acid dioctyl ester be 288nm, survey light absorption value at the 288nm place, each concentration is made parallel sample. molar absorptivity is calculated as: ε=light absorption value/volumetric molar concentration.This experimental calculation gets ε=16048.56Lmol
-1
Coupling ratio is measured: prepare 150 μ gmL
-120% ethanolic soln of bovine serum albumin, with coupled product with 20% alcohol dilution to 150 μ gmL
-1, survey light absorption value at the 288nm place, be blank with 20% ethanol, the light absorption value of measuring is respectively A
1, A
2, then coupling ratio r is: r=[(A
1-A
2)/ε]/(150 * 10
-3/ 66200), this experimental calculation gets r ≈ 18.
Wherein ε is molar absorptivity (Lmol
-1), 66200 is the molecular weight of bovine serum albumin, 150 * 10
-3Be bovine serum albumin concentration (μ gmL
-1).
Beneficial effect of the present invention: the present invention has synthesized the artificial antigen of dioctyl phthalate (DOP), and synthesis step is succinct, effectively, can be used for immunoassay fully, for later research provides convenience, can satisfy domestic needs to its research.
Description of drawings
The liquid chromatogram of Fig. 1 4-nitrophthalic acid dioctyl ester.
The mass spectrum of Fig. 2 4-nitrophthalic acid dioctyl ester.
The ultraviolet figure of Fig. 3 4-nitrophthalic acid dioctyl ester.
The liquid chromatogram of Fig. 4 4-aminophthalic acid dioctyl ester.
The mass spectrum of Fig. 5 4-aminophthalic acid dioctyl ester.
The ultraviolet figure of Fig. 6 4-aminophthalic acid dioctyl ester.
Embodiment
(1) preparation of artificial semiantigen:
1. 4-nitrophthalic acid dioctyl ester is synthetic
The 4-nitrophthalic acid that takes by weighing 0.12mol is in the three-necked flask of 100mL, the n-Octanol that adds 0.1mol (15.74ml), add a certain amount of benzene hydrotropy, under stirring condition, the vitriol oil that slowly adds 1.6mL, heat temperature raising react 7-24h to 110-130 ℃, the pressure reducing and steaming organic solvent, the residual Na that uses mass concentration 10% in the cold water that joins of oily
2CO
3It is colourless that solution is washed till lower aqueous layer, obtains bolarious oily crude product, carries out recrystallization with dehydrated alcohol, obtains the 4-nitrophthalic acid dioctyl ester of 45mmol.
The making of silica gel thin-layer plate: take by weighing silica gel 12g, be dissolved in the sodium cellulose glycolate solution of 40mL 0.5% mass concentration, fully stir into pasty state with glass stick, ultra-sonic oscillation 1 minute, be uniformly coated on the sheet glass, after the In Shade seasoning, the baking oven of putting into 105 ℃ activates 1h, and it is standby to put into loft drier at last.
Thin layer chromatography detects: 1cm place, silica gel thin sheet lower end makes a sea line, draws reaction solution 1 μ L point on line, and point sample dries up after finishing, thin plate is put into chromatography cylinder, chromatographic solution is an acetate: the normal hexane volume ratio is 1: 15, is expanded to thin plate 3/4 place, gets plate and dries up solvent.Thin plate is placed uv analyzer, and the 254nm wavelength is observed, and is that 0.74 place observes the colour developing point and the initial point place does not have the colour developing point as reaction end at Rf.
2. 4-aminophthalic acid dioctyl ester is synthetic
Take by weighing the 7mmol reduced iron powder in the 50mL round-bottomed flask, add 2mL water, 1mmol ammonium chloride, heat 15min in the water-bath.Other gets 4-nitrophthalic acid dioctyl ester 1.4mmol, behind a certain amount of dissolve with methanol, divides to add in the middle of the above-mentioned reaction solution back flow reaction 4-6h for 3 times.The filtered while hot iron powder carries out underpressure distillation with filtrate, and it is standby as haptens that the orange red residual small amount of thermal dissolve with methanol solution of using that obtains, low temperature are separated out the 4-aminophthalic acid dioctyl ester of 1.17mmol (0.47g) orange oily liquids.
Thin layer chromatography detects: 1cm place, silica gel thin sheet lower end makes a sea line, draws reaction solution 1 μ L point on line, and point sample dries up after finishing, thin plate is put into chromatography cylinder, and chromatographic solution is an acetate: the normal hexane volume ratio is 1: 15, is expanded to thin plate 3/4 place, get plate, dry up solvent.Thin plate being placed uv analyzer, observe at the 254nm wavelength, is that 0.52 place observes the colour developing point as reaction end at Rf.
(2) preparation of artificial antigen:
1. prepare A liquid: get the 0.023mmol haptens in the 25mL beaker, add the 1mol/L hydrochloric acid of 2mL dimethyl formamide, 0.2mL water and 0.2mL, form yellow solution, be cooled to 0-5 ℃.Progressively drip the 1mol/L sodium nitrite solution then, with the starch potassium iodide paper monitoring, become pewter up to test paper and stop to drip, 4 ℃ are stirred 1h down, and this liquid is A liquid.
2. prepare B liquid: the bovine serum albumin that takes by weighing 150mg is dissolved in pH 9.0 borate buffer solutions of 6mL, 4 ℃ of preservations.This liquid is B liquid.
Borate buffer solution: 0.2mol/L boric acid: boric acid 12.37g adds water to 1000mL, the 0.05mol/L borax: borax 19.07g adds water to 1000mL, above-mentioned two solution is the borate buffer solution of pH 9.0 with 2: 8 mixed of volume ratio.
3. under 4 ℃ of stirrings, A liquid dropwise is added drop-wise to B liquid, and regulates pH, pH is remained on stir under 9,4 ℃ of conditions and spend the night, promptly obtain the artificial antigen mixed solution with the sodium hydroxide solution of 1mol/L.
4. the artificial antigen mixed solution is moved in the dialysis tubing, dialysed 4-6 days with the deionized water of 6 * 1L.Use lyophilization that the liquid in the dialysis tubing is made powder at last, promptly obtain artificial antigen: dioctyl phthalate (DOP)-bovine serum albumin.
Dialysis tubing pre-treatment: get the dialysis tubing of 10cm, boil 5min, use 60 ℃ deionized water rinsing 3min again, be kept in 4 ℃ of deionized waters standby.
(3) evaluation of dioctyl phthalate artificial antigen: protein concentration and the coupling ratio of measuring conjugate.
The conjugate determination of protein concentration: compound concentration is 0,40,60,80,100,120,160,200 μ gml
-1Bovine serum albumen solution 1.5ml, add 5ml coomassie brilliant blue staining liquid, mixing immediately, warm 5 minutes of 30 ℃ of water-baths, each concentration is made parallel sample. survey light absorption value, the relation curve of drafting protein concentration and light absorption value at 595nm place.Antigenic solution is diluted by a certain percentage, measure the light absorption value of antigenic solution at the 595nm place, obtain the corresponding proteins concentration of antigenic solution from curve.The protein concentration that this experimental calculation gets antigenic solution is 7.67mgml
-1
Coupling ratio is measured: use the spectrophotometry coupling ratio.Spectrophotometry is measured respectively by two kinds of molecular conecentrations of link coupled the principle that absorption and its concentration of light is proportionlity with material, in macromole and small molecules conjugate, two kinds of molecules have different separately ultraviolet scanning spectrums, and show the character of spectrogram superposition.
Molar absorption coefficient ε: preparation 4-aminophthalic acid dioctyl ester concentration is 0,10,20,30 μ gml
-120% ethanolic soln, by UV scanning as can be known the maximum absorption wavelength of 4-aminophthalic acid dioctyl ester be 288nm, survey light absorption value at the 288nm place, each concentration is made parallel sample. molar absorptivity is calculated as: ε=light absorption value/volumetric molar concentration.This experimental calculation gets ε=16048.56Lmol
-1
Coupling ratio is measured: prepare 150 μ gml
-120% ethanolic soln of bovine serum albumin, with coupled product with 20% alcohol dilution to 150 μ gml
-1, survey light absorption value at the 288nm place, be blank with 20% ethanol, the light absorption value of measuring is A1, A2, then coupling ratio r is: r=[(A
1-A
2)/ε]/(150 * 10
-3/ 66200), this experimental calculation gets r ≈ 18.Wherein ε is molar absorptivity (Lmol
-1), 66200 is the molecular weight of bovine serum albumin, 150 * 10
-3Be bovine serum albumin concentration (μ gml
-1).
Claims (1)
1. the preparation method of a dioctyl phthalate artificial antigen, it is characterized in that with the 4-nitrophthalic acid be raw material, under the catalysis of the vitriol oil with n-Octanol generation esterification, utilize the iron powder reducing method to make the nitroreduction on the 4-nitrophthalic acid dioctyl ester phenyl ring be amido then, the preparation haptens; Utilize the diazotization method that the amido on the haptens is carried out diazotization and make it combining with bovine serum albumin, the artificial antigen of preparation dioctyl phthalate (DOP), i.e. dioctyl phthalate (DOP)-bovine serum albumin; Step is:
(1) preparation of artificial semiantigen:
1. 4-nitrophthalic acid dioctyl ester is synthetic
The 4-nitrophthalic acid that takes by weighing 0.12mol is in the three-necked flask of 100mL, adding 0.1mol is the n-Octanol of 15.74mL, add a certain amount of benzene hydrotropy, under stirring condition, the vitriol oil that slowly adds 1.6mL, heat temperature raising react 7-24h to 110-130 ℃, the pressure reducing and steaming organic solvent, the residual Na that uses mass concentration 10% in the cold water that joins of oily
2CO
3It is colourless that solution is washed till lower aqueous layer, gets the upper strata and obtain bolarious oily crude product, carries out recrystallization with dehydrated alcohol, obtains the 4-nitrophthalic acid dioctyl ester of 45mmol;
Thin layer chromatography detects: 1cm place, silica gel thin sheet lower end makes a sea line, draws reaction solution 1 μ L point on line, and point sample dries up after finishing, thin plate is put into chromatography cylinder, and chromatographic solution is an acetate: the normal hexane volume ratio is 1: 15, is expanded to thin plate 3/4 place, get plate, dry up solvent; Thin plate being placed uv analyzer, observe at the 254nm wavelength, is that 0.74 place observes the colour developing point as reaction end at Rf;
2. 4-aminophthalic acid dioctyl ester is synthetic
Take by weighing the 9mmol reduced iron powder in the 50mL round-bottomed flask, add 10mL water, 3mmol ammonium chloride, heat 15min in the water-bath; Other takes by weighing 4-nitrophthalic acid dioctyl ester 3mmol, behind a certain amount of dissolve with methanol, divides to add in the middle of the above-mentioned reaction solution back flow reaction 4-6h for 3 times; The filtered while hot iron powder carries out underpressure distillation with filtrate, and it is standby as haptens that the orange red residual small amount of thermal dissolve with methanol solution of using that obtains, low temperature are separated out the 4-aminophthalic acid dioctyl ester of 1.17mmol orange oily liquids;
Thin layer chromatography detects: 1cm place, silica gel thin sheet lower end makes a sea line, draws reaction solution 1 μ L point on line, and point sample dries up after finishing, thin plate is put into chromatography cylinder, and chromatographic solution is an acetate: the normal hexane volume ratio is 1: 15, is expanded to thin plate 3/4 place, get plate, dry up solvent; Thin plate being placed uv analyzer, observe at the 254nm wavelength, is that 0.52 place observes the colour developing point as reaction end at Rf;
(2) preparation of artificial antigen:
1. prepare A liquid: get the 0.023mmol haptens in the 25mL beaker, the 1mol/L hydrochloric acid that adds 2mL dimethyl formamide, 0.2mL water and 0.2mL, form yellow solution, be cooled to 0-5 ℃, progressively drip the 1mol/L sodium nitrite solution then,, become pewter up to test paper and stop to drip with the starch potassium iodide paper monitoring, 4 ℃ are stirred 1h down, and this liquid is A liquid;
2. prepare B liquid: the bovine serum albumin that takes by weighing 150mg is dissolved in pH 9.0 borate buffer solutions of 6mL, 4 ℃ of preservations, and this liquid is B liquid;
3. under 4 ℃ of stirrings, A liquid dropwise is added drop-wise in the B liquid, and regulates pH with the sodium hydroxide solution of 1mol/L, pH is remained under 9,4 ℃, stirring is spent the night, and promptly obtains the artificial antigen mixed solution;
4. the artificial antigen mixed solution is moved in the dialysis tubing, dialysed 4-6 days with the deionized water of 6 * 1L; Use lyophilization that the liquid in the dialysis tubing is made powder at last, promptly obtain artificial antigen: dioctyl phthalate (DOP)-bovine serum albumin.
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|---|---|---|---|---|
| CN102206269A (en) * | 2011-05-05 | 2011-10-05 | 聊城大学 | Diheptyl phthalate complete antigen and preparation method and application thereof |
| CN102225898A (en) * | 2011-05-05 | 2011-10-26 | 聊城大学 | Synthesis method of 4- nitro diheptyl phthalate |
| CN102225901A (en) * | 2011-05-05 | 2011-10-26 | 聊城大学 | Synthetic method for 4-amino diheptyl phthalate |
| CN102680715A (en) * | 2012-01-15 | 2012-09-19 | 河南科技大学 | Colloidal gold test paper for quickly detecting di-n-octyl ortho-phthalate and preparation method thereof |
| CN103149351A (en) * | 2013-03-21 | 2013-06-12 | 江南大学 | Synthesis and application of envelope antigen universal for pyrethriods pesticide |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101161681B (en) * | 2007-11-01 | 2010-12-15 | 江南大学 | Method for preparing double-flumethasone artificial antigen |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102206269A (en) * | 2011-05-05 | 2011-10-05 | 聊城大学 | Diheptyl phthalate complete antigen and preparation method and application thereof |
| CN102225898A (en) * | 2011-05-05 | 2011-10-26 | 聊城大学 | Synthesis method of 4- nitro diheptyl phthalate |
| CN102225901A (en) * | 2011-05-05 | 2011-10-26 | 聊城大学 | Synthetic method for 4-amino diheptyl phthalate |
| CN102680715A (en) * | 2012-01-15 | 2012-09-19 | 河南科技大学 | Colloidal gold test paper for quickly detecting di-n-octyl ortho-phthalate and preparation method thereof |
| CN102680715B (en) * | 2012-01-15 | 2014-08-06 | 河南科技大学 | Colloidal gold test paper for quickly detecting di-n-octyl ortho-phthalate and preparation method thereof |
| CN103149351A (en) * | 2013-03-21 | 2013-06-12 | 江南大学 | Synthesis and application of envelope antigen universal for pyrethriods pesticide |
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