CN106700086A - Preparation method of polymer brush for chemical and biological sensing - Google Patents
Preparation method of polymer brush for chemical and biological sensing Download PDFInfo
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- CN106700086A CN106700086A CN201611024970.0A CN201611024970A CN106700086A CN 106700086 A CN106700086 A CN 106700086A CN 201611024970 A CN201611024970 A CN 201611024970A CN 106700086 A CN106700086 A CN 106700086A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
- C08G81/02—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers at least one of the polymers being obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C08G81/021—Block or graft polymers containing only sequences of polymers of C08C or C08F
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F120/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F120/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F120/10—Esters
- C08F120/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F120/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
- G01N33/574—Immunoassay; Biospecific binding assay; Materials therefor for cancer
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Abstract
The invention discloses a preparation method of a polymer brush for chemical and biological sensing. The method is characterized by comprising the steps of enabling polyacrylonitrile and sodium azide to have click chemical reaction so as to prepare polyvinyl tetrazole, enabling the polyvinyl tetrazole to have reaction with methacrylate compounds to obtain a product, dialyzing the product, and carrying out freeze drying to obtain the polymer brush. The polymer brush prepared by the preparation method disclosed by the invention successfully realizes the amplification for cancer embryo antigen detection signals, and the minimum detection limit is 0.1pg/ml.
Description
Technical field
The present invention relates to a kind of preparation method of polymer brush, specifically a kind of polymer that can be used for chemical-biological sensing
The preparation method of brush, belongs to functional high polymer material field.
Background technology
In recent years, with the continuous quickening and the rapid raising of industrialized level of urbanization process, the problem of environmental pollution
Protrude further.The harmful effect that environmental pollution is brought is so that tumor incidence cumulative year after year.The early detection and diagnosis of tumour
It is prevented and treated most important.
Polymer brush is a kind of polymer containing big molecule side chain, in recent years because its unique architectural feature and application are preceding
Scape, causes the extensive research interest of scholars.The appearance of click chemistry and after successfully referring to field of polymer technology, because it has
Have the advantages that reaction condition is gentle, speed is fast, efficiency high, rapidly becomes a kind of important means for preparing polymer brush.
Detection antibody is connected in polymer brush main chain terminal, is designed on side chain and be can be used for signal amplification combination containing multiple
Monomer, it is and polymer brush is immobilized to compound is formed on the carriers such as nm of gold, signal output will be made exponentially to increase.
Therefore, the signal for quickly and efficiently preparing the polymer brush compound constructed and using it for tumor-marker analyte detection amplifies to be had
Significance.
The content of the invention
It is an object of the present invention to provide a kind of preparation method of the polymer brush that can be used for chemical-biological sensing.
The invention provides a kind of preparation method of the polymer brush that can be used for chemical-biological sensing, comprise the following steps：
Using the chain transfer agents containing carboxyl, end group is obtained for carboxyl by reversible addion-fragmentation chain transfer radical polymerization
Polyacrylonitrile, be then added in DMF with sodium azide, ammonium chloride, stir, be placed in 120 Celsius
Click chemistry reaction is carried out under the conditions of degree, reaction is carried out at least 12 hours, wherein, polyacrylonitrile is with the mass ratio of sodium azide
1:1~20:1, ammonium chloride is 1 with the mass ratio of sodium azide:1, product is obtained through cooling, hydrochloric acid acidifying, separation, vacuum drying
Polyvinyl alcohol tetrazole, is then birdsed of the same feather flock together polyvinyl alcohol tetrazole with the methacrylate obtained by ATRP
Compound and triethylamine are added in DMF, are stirred, and are placed under 65 degrees celsius and are reacted, instead
Should at least carry out 3 hours, wherein polyacrylonitrile and the mass ratio of methacrylic polymer is 1:1~1:5, triethylamine and first
The mass ratio of base acrylic polymer is 1:1, product obtains polymer brush through cooling, dialysis, freeze-drying.
Compared with the prior art the present invention has advantages below：The preparation method is simple of the polymer brush that the present invention is provided is easy
OK, by the regulation to polyacrylonitrile and sodium azide consumption, the grafting density of polymer brush, the polymer of gained can be controlled
Brush is applied to the detection of tumor markers, is successfully realized the amplification that carcinomebryonic antigen surveys signal, lowest detection be limited to 0.1 pik/
Milliliter.
Specific embodiment：
The following detailed description of the present invention and provide several embodiments：
Embodiment one：
2.0 milliliters of acrylonitrile, 0.042 gram of 4- itrile group valeric acids dithiobenzoic acid, 0.0123 gram of azodiisobutyronitrile are added to
In equipped with 2.0 milliliters of ampoule bottles of DMF, stir, be placed under 75 degrees celsius and react 4 hours, produce
Thing obtains polyacrylonitrile through precipitation, suction filtration, vacuum drying, by 2.0 milliliters of GMAs, 0.0223 milliliter of 2-
Isobutyl ethyl bromide, 0.0338 gram of copper bromide, 0.0322 milliliter of pentamethyl-diethylenetriamine, 0.0266 gram of ascorbic acid are added to
In equipped with 2.0 milliliters of ampoule bottles of DMF, stir, be placed under 65 degrees celsius and react 6 hours, produce
Thing obtains poly (glycidyl methacrylate) through cooling, dialysis, freeze-drying, by 0.5 gram of polyacrylonitrile, 0.5 gram of Azide
Sodium, 0.5 gram of ammonium chloride will enter in equipped with 5.0 milliliters of ampoule bottles of DMF, stir, and are placed in 120 and take the photograph
Reacted 12 hours under the conditions of family name's degree, product obtains polyvinyl alcohol tetrazole, 0.5 gram through cooling, hydrochloric acid acidifying, separation, vacuum drying
Polyvinyl alcohol tetrazole, 0.5 gram of poly (glycidyl methacrylate), 0.68 milliliter of triethylamine are added to equipped with 3.0 milliliters of N, N-
In the ampoule bottle of dimethylformamide, stir, be placed under 65 degrees celsius and react 3 hours, product thing through cooling, thoroughly
Analysis, freeze-drying obtain polymer brush.Resulting polymers brush is applied to the detection of carcinomebryonic antigen with the compound that nm of gold is constructed,
Lowest detection is limited to 0.16 pg/ml.
Embodiment two：
2.0 milliliters of acrylonitrile, 0.042 gram of 4- itrile group valeric acids dithiobenzoic acid, 0.0123 gram of azodiisobutyronitrile are added to
In equipped with 2.0 milliliters of ampoule bottles of DMF, stir, be placed under 75 degrees celsius and react 4 hours, produce
Thing obtains polyacrylonitrile through precipitation, suction filtration, vacuum drying, by 2.0 milliliters of GMAs, 0.0223 milliliter of 2-
Isobutyl ethyl bromide, 0.0338 gram of copper bromide, 0.0322 milliliter of pentamethyl-diethylenetriamine, 0.0266 gram of ascorbic acid are added to
In equipped with 2.0 milliliters of ampoule bottles of DMF, stir, be placed under 65 degrees celsius and react 6 hours, produce
Thing obtains poly (glycidyl methacrylate) through cooling, dialysis, freeze-drying, by 0.5 gram of polyacrylonitrile, 0.05 gram of Azide
Sodium, 0.05 gram of ammonium chloride will enter in equipped with 5.0 milliliters of ampoule bottles of DMF, stir, and be placed in 120
Reacted 12 hours under degrees celsius, product obtains polyvinyl alcohol tetrazole, 0.5 through cooling, hydrochloric acid acidifying, separation, vacuum drying
Gram polyvinyl alcohol tetrazole, 0.5 gram of poly (glycidyl methacrylate), 0.68 milliliter of triethylamine are added to equipped with 3.0 milliliters of N,
In the ampoule bottle of dinethylformamide, stir, be placed under 65 degrees celsius and react 3 hours, product thing through cooling, thoroughly
Analysis, freeze-drying obtain polymer brush.Resulting polymers brush is applied to the detection of carcinomebryonic antigen with the compound that nm of gold is constructed,
Lowest detection is limited to 0.34 pg/ml.
Embodiment three：
2.0 milliliters of acrylonitrile, 0.042 gram of 4- itrile group valeric acids dithiobenzoic acid, 0.0123 gram of azodiisobutyronitrile are added to
In equipped with 2.0 milliliters of ampoule bottles of DMF, stir, be placed under 75 degrees celsius and react 4 hours, produce
Thing obtains polyacrylonitrile through precipitation, suction filtration, vacuum drying, by 2.0 milliliters of GMAs, 0.0223 milliliter of 2-
Isobutyl ethyl bromide, 0.0338 gram of copper bromide, 0.0322 milliliter of pentamethyl-diethylenetriamine, 0.0266 gram of ascorbic acid are added to
In equipped with 2.0 milliliters of ampoule bottles of DMF, stir, be placed under 65 degrees celsius and react 6 hours, produce
Thing obtains poly (glycidyl methacrylate) through cooling, dialysis, freeze-drying, by 0.5 gram of polyacrylonitrile, 0.5 gram of Azide
Sodium, 0.5 gram of ammonium chloride will enter in equipped with 5.0 milliliters of ampoule bottles of DMF, stir, and are placed in 120 and take the photograph
Reacted 12 hours under the conditions of family name's degree, product obtains polyvinyl alcohol tetrazole, 0.5 gram through cooling, hydrochloric acid acidifying, separation, vacuum drying
Polyvinyl alcohol tetrazole, 1.0 grams of poly (glycidyl methacrylate)s, 1.36 milliliters of triethylamines are added to equipped with 3.0 milliliters of N, N-
In the ampoule bottle of dimethylformamide, stir, be placed under 65 degrees celsius and react 3 hours, product thing through cooling, thoroughly
Analysis, freeze-drying obtain polymer brush.Resulting polymers brush is applied to the detection of carcinomebryonic antigen with the compound that nm of gold is constructed,
Lowest detection is limited to 0.16 pg/ml.
Example IV：
2.0 milliliters of acrylonitrile, 0.042 gram of 4- itrile group valeric acids dithiobenzoic acid, 0.0123 gram of azodiisobutyronitrile are added to
In equipped with 2.0 milliliters of ampoule bottles of DMF, stir, be placed under 75 degrees celsius and react 4 hours, produce
Thing obtains polyacrylonitrile through precipitation, suction filtration, vacuum drying, and 2.0 milliliters of hydroxyethyl methacrylates, 0.0204 milliliter of 2- bromine is different
Ethyl butyrate, 0.0310 gram of copper bromide, 0.0294 milliliter of pentamethyl-diethylenetriamine, 0.0243 gram of ascorbic acid are added to and are equipped with
In 2.0 milliliters of ampoule bottles of DMF, stir, be placed under 65 degrees celsius and react 6 hours, product warp
Cooling, dialysis, freeze-drying obtain poly hydroxy ethyl acrylate, by 0.5 gram of polyacrylonitrile, 0.5 gram of sodium azide, 0.5 gram
Ammonium chloride will enter in equipped with 5.0 milliliters of ampoule bottles of DMF, stir, and be placed in 120 degrees celsius
Lower reaction 12 hours, product obtains polyvinyl alcohol tetrazole, 0.5 gram of polyvinyl through cooling, hydrochloric acid acidifying, separation, vacuum drying
Tetrazolium, 0.5 gram of poly (glycidyl methacrylate), 0.68 milliliter of triethylamine are added to equipped with 3.0 milliliters of N, N- dimethyl methyls
In the ampoule bottle of acid amides, stir, be placed under 65 degrees celsius and react 3 hours, product thing is dry through cooling, dialysis, freezing
It is dry to obtain polymer brush.Resulting polymers brush is applied to the detection of carcinomebryonic antigen with the compound that graphene oxide is constructed, minimum
Detection is limited to 1.4 pg/mls.
Embodiment five：
2.0 milliliters of acrylonitrile, 0.042 gram of 4- itrile group valeric acids dithiobenzoic acid, 0.0123 gram of azodiisobutyronitrile are added to
In equipped with 2.0 milliliters of ampoule bottles of DMF, stir, be placed under 75 degrees celsius and react 4 hours, produce
Thing obtains polyacrylonitrile through precipitation, suction filtration, vacuum drying, and 2.0 milliliters of hydroxyethyl methacrylates, 0.0204 milliliter of 2- bromine is different
Ethyl butyrate, 0.0310 gram of copper bromide, 0.0294 milliliter of pentamethyl-diethylenetriamine, 0.0243 gram of ascorbic acid are added to and are equipped with
In 2.0 milliliters of ampoule bottles of DMF, stir, be placed under 65 degrees celsius and react 6 hours, product warp
Cooling, dialysis, freeze-drying obtain poly hydroxy ethyl acrylate, by 0.5 gram of polyacrylonitrile, 0.05 gram of sodium azide, 0.05
Gram ammonium chloride will enter in equipped with 5.0 milliliters of ampoule bottles of DMF, stir, and be placed in 120 degrees Celsius of bars
Reacted 12 hours under part, product obtains polyvinyl alcohol tetrazole, 0.5 gram of polyethylene through cooling, hydrochloric acid acidifying, separation, vacuum drying
Base tetrazolium, 0.5 gram of poly (glycidyl methacrylate), 0.68 milliliter of triethylamine are added to equipped with 3.0 milliliters of N, N- dimethyl
In the ampoule bottle of formamide, stir, be placed under 65 degrees celsius and react 3 hours, product thing is through cooling, dialysis, freezing
It is dried to obtain polymer brush.Resulting polymers brush is applied to the detection of carcinomebryonic antigen with the compound that graphene oxide is constructed, most
Low detection is limited to 2.3 pg/mls.
Embodiment six：
2.0 milliliters of acrylonitrile, 0.042 gram of 4- itrile group valeric acids dithiobenzoic acid, 0.0123 gram of azodiisobutyronitrile are added to
In equipped with 2.0 milliliters of ampoule bottles of DMF, stir, be placed under 75 degrees celsius and react 4 hours, produce
Thing obtains polyacrylonitrile through precipitation, suction filtration, vacuum drying, and 2.0 milliliters of hydroxyethyl methacrylates, 0.0204 milliliter of 2- bromine is different
Ethyl butyrate, 0.0310 gram of copper bromide, 0.0294 milliliter of pentamethyl-diethylenetriamine, 0.0243 gram of ascorbic acid are added to and are equipped with
In 2.0 milliliters of ampoule bottles of DMF, stir, be placed under 65 degrees celsius and react 6 hours, product warp
Cooling, dialysis, freeze-drying obtain poly hydroxy ethyl acrylate, by 0.5 gram of polyacrylonitrile, 0.5 gram of sodium azide, 0.5 gram
Ammonium chloride will enter in equipped with 5.0 milliliters of ampoule bottles of DMF, stir, and be placed in 120 degrees celsius
Lower reaction 12 hours, product obtains polyvinyl alcohol tetrazole, 0.5 gram of polyvinyl through cooling, hydrochloric acid acidifying, separation, vacuum drying
Tetrazolium, 1.0 grams of poly (glycidyl methacrylate)s, 1.36 milliliters of triethylamines are added to equipped with 3.0 milliliters of N, N- dimethyl methyls
In the ampoule bottle of acid amides, stir, be placed under 65 degrees celsius and react 3 hours, product thing is dry through cooling, dialysis, freezing
It is dry to obtain polymer brush.Resulting polymers brush is applied to the detection of carcinomebryonic antigen with the compound that graphene oxide is constructed, minimum
Detection is limited to 0.6 pg/ml.
Claims (3)
1. it is a kind of can be used for chemical-biological sensing polymer brush preparation method, it is characterized in that：Use first and contain carboxyl
Chain transfer agents, the polyacrylonitrile that end group is carboxyl is obtained by reversible addion-fragmentation chain transfer radical polymerization, then with it is folded
Sodium nitride, ammonium chloride are added in DMF, are stirred, and click chemistry are carried out under 120 degrees celsius anti-
Should, reaction is carried out at least 12 hours, wherein, polyacrylonitrile is 1 with the mass ratio of sodium azide:1~20:1, ammonium chloride and nitrine
The mass ratio for changing sodium is 1:1, product obtains polyvinyl alcohol tetrazole through cooling, hydrochloric acid acidifying, separation, vacuum drying, then will be poly-
Vinyl tetrazolium is added to the methacrylic acid lipid aggregate thing and triethylamine that are prepared by ATRP
In DMF, stir, reacted under 65 degrees celsius, reaction is at least carried out 3 hours, wherein poly- second
Alkenyl tetrazolium is 1 with the mass ratio of methacrylic acid lipid aggregate thing:1~1:5, triethylamine and methacrylic acid lipid aggregate thing
Mass ratio be 1:1, product obtains polymer brush through cooling, dialysis, freeze-drying.
2. can be used to the preparation method of polymer brush of chemical-biological sensing its feature according to a kind of described in claim 1. exist
Methacrylic acid lipid aggregate thing used when the polymer brush is prepared is poly (glycidyl methacrylate) and poly- methyl
Hydroxy-ethyl acrylate.
3. can be used to the preparation method of polymer brush of chemical-biological sensing its feature according to a kind of described in claim 1. exist
Chemical-biological sensing is applied in the polymer brush for preparing, the amplification of carcinomebryonic antigen detection signal, minimum inspection is successfully realized
Survey is limited to 0.1 pg/ml.
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| CN201611024970.0A CN106700086B (en) | 2016-11-22 | 2016-11-22 | A kind of preparation method for the polymer brush can be used for chemical-biological sensing |
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| CN201611024970.0A CN106700086B (en) | 2016-11-22 | 2016-11-22 | A kind of preparation method for the polymer brush can be used for chemical-biological sensing |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108585543A (en) * | 2018-04-17 | 2018-09-28 | 黔南民族师范学院 | A kind of bio-sensing three-dimensional chip and preparation method thereof |
| CN109908982A (en) * | 2019-03-11 | 2019-06-21 | 黔南民族师范学院 | A kind of preparation method and applications of traditional Chinese medicinal components screening three-dimensional chip |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102952236A (en) * | 2011-08-29 | 2013-03-06 | 南开大学 | Molecularly imprinted polymeric microsphere resin applicable to aqueous solution system and preparing method thereof |
| CN103665387A (en) * | 2013-12-09 | 2014-03-26 | 东南大学 | Method for preparing accurate polymer network |
| CN104371131A (en) * | 2014-03-12 | 2015-02-25 | 南开大学 | Preparation method for molecularly imprinted polymer microballoon with hydrophilic high-molecular brush |
-
2016
- 2016-11-22 CN CN201611024970.0A patent/CN106700086B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102952236A (en) * | 2011-08-29 | 2013-03-06 | 南开大学 | Molecularly imprinted polymeric microsphere resin applicable to aqueous solution system and preparing method thereof |
| CN103665387A (en) * | 2013-12-09 | 2014-03-26 | 东南大学 | Method for preparing accurate polymer network |
| CN104371131A (en) * | 2014-03-12 | 2015-02-25 | 南开大学 | Preparation method for molecularly imprinted polymer microballoon with hydrophilic high-molecular brush |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108585543A (en) * | 2018-04-17 | 2018-09-28 | 黔南民族师范学院 | A kind of bio-sensing three-dimensional chip and preparation method thereof |
| CN108585543B (en) * | 2018-04-17 | 2020-10-09 | 黔南民族师范学院 | Biosensing three-dimensional chip and preparation method thereof |
| CN109908982A (en) * | 2019-03-11 | 2019-06-21 | 黔南民族师范学院 | A kind of preparation method and applications of traditional Chinese medicinal components screening three-dimensional chip |
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