CN112011082B - DNA imprinting material based on block macromolecular chain monomer and preparation method thereof - Google Patents
DNA imprinting material based on block macromolecular chain monomer and preparation method thereof Download PDFInfo
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Abstract
The invention discloses a DNA imprinting material based on a block macromolecular chain monomer and a preparation method thereof, wherein O-ethyl-S- (1-phenethyl) dithiocarbonate is used as a chain transfer agent, brominated 1-butyl-3-vinyl imidazole and 4-chloromethyl styrene are used as functional monomers, a reversible addition-fragmentation chain transfer polymerization technology is adopted to obtain a block macromolecular chain precursor, the precursor is further reacted with vinyl imidazole, the functional block macromolecular chain monomer is obtained after purification, the functional block macromolecular chain monomer is self-assembled with DNA, and the functional block macromolecular chain precursor is polymerized in an ammonium persulfate and tetramethyl ethylene diamine initiation system to obtain the DNA imprinting hydrogel. According to the invention, through the design and application of the block macromolecular chain monomer, on one hand, the good structural stability of DNA can be maintained in the imprinting process, and the accuracy and the integrity of imprinting holes are ensured; on the other hand, highly concentrated cross-linking region chain segments in the block macromolecular chain monomer can efficiently construct a imprinted hole structure, and the conditions provide guarantee for realizing the high-identification DNA imprinted material.
Description
Technical Field
The invention belongs to the technical field of high polymer materials, and particularly relates to a DNA imprinting material based on a block macromolecular chain monomer and a preparation method thereof.
Background
In the past decades, deoxyribonucleic acid (DNA) detection has attracted considerable attention due to its related applications, particularly in molecular diagnostics and early diagnosis of various diseases, such as genetic diseases, cancer, viral infections and chronic diseases. In these diseases, DNA recognition and isolation is critical. Therefore, the research on novel DNA identification and separation methods and the development of novel efficient DNA separation materials become the targets pursued by researchers in the fields of biology, chemistry, materials and the like.
Molecularly Imprinted Polymers (MIPs) are materials with research targets because they have an artificial recognition cavity for the target molecule. The recognition cavities complement the chemical structure of the target molecule in terms of shape, size and arrangement of functional groups. Three special features of MIP make it the target of intensive research: (1) Their high affinity and selectivity are similar to natural receptors. (2) Its unique stability is superior to that exhibited by natural biomolecules; (3) The preparation is simple and convenient and the adaptability in different practical applications is realized. The intelligent recognition effect of the molecularly imprinted polymer material on the template molecules is mainly caused by the existence of imprinted holes which have the function of mutually matching the shape, size and functional groups of the template molecules in the polymer, and the technology is put forward by scholars at home and abroad. The development of southern blotting techniques has been relatively slow in recent years compared to blotting techniques using small molecules as templates, mainly because of their low recognition ability, which is difficult to meet the practical demands of development in the modern biomedical field. An important factor affecting the recognition of southern blotting techniques is the structural stability of the template DNA during the blotting process. The traditional functional monomer and cross-linking agent endow them with strong flexibility relative to the small molecular volume of DNA, so that the functional monomer and cross-linking agent can easily permeate into the DNA, thereby destroying the hydrogen bonds in the DNA for maintaining the stable structure and conformation, and causing the change of the DNA structure.
Disclosure of Invention
The invention aims to provide a DNA imprinting material based on a block macromolecular chain monomer and a preparation method thereof, wherein the block macromolecular chain monomer consists of a functional region chain segment which has good interaction with DNA and a cross-linking region chain segment which can construct an accurate imprinting hole structure. The macromolecular chain monomer can keep the structural stability of DNA on one hand, and can obtain an imprinted hole structure with high specificity interaction in a molecularly imprinted material on the other hand.
In order to achieve the technical purpose, the invention is specifically realized by the following technical scheme:
a preparation method of a DNA imprinting material based on a block macromolecular chain monomer comprises the following steps:
1) Dissolving O-ethyl-S- (1-phenylethyl) dithiocarbonate and brominated 1-butyl-3-vinyl imidazole in an organic solvent, adding an initiator, and reacting at a preset reaction temperature and time (the reaction temperature and the reaction time are determined according to the half-life of AIBN) under an oxygen-free condition to obtain a block macromolecular chain transfer agent; the reaction route is as follows:
wherein, X takes a value of 10-200;
2) Respectively adding a block macromolecular chain transfer agent, 4-chloromethyl styrene and an initiator into an organic solvent, reacting under an anaerobic condition, and obtaining a block macromolecular chain precursor at a preset reaction temperature and time (the reaction temperature and the reaction time are determined according to the half-life of AIBN); the reaction route is as follows:
wherein y takes a value of 10-100;
3) Carrying out alkylation reaction on the macromolecular chain precursor and vinyl imidazole to obtain a final functional macromolecular chain monomer; the reaction route is as follows:
4) Placing DNA and a functional macromolecular chain monomer in a phosphoric acid buffer solution for assembly, sequentially adding ammonium persulfate and tetramethyl ethylene diamine, and reacting under an anaerobic condition to obtain the DNA imprinting hydrogel:
further, the molar ratio of the O-ethyl-S- (1-phenylethyl) dithiocarbonate to the brominated 1-butyl-3-vinyl imidazole is 1.
Further, the molar ratio of the block macromolecular chain transfer agent to the p-4-chloromethyl styrene is 1.
Further, the mass ratio of the block macromolecular chain precursor to the vinyl imidazole is 1.5-2.
Furthermore, the mass ratio of the DNA to the functional macromolecular chain monomer is 1 to 5.
Further, the organic solvent is N, N-dimethyl sulfoxide; the initiator is azobisisobutyronitrile.
In another aspect of the present invention, the southern blotting hydrogel prepared by the above-mentioned preparation method is also within the scope of the present invention.
The invention has the beneficial effects that:
according to the invention, the template molecules capable of stabilizing in the imprinting process are synthesized by utilizing the designability of macromolecules and the characteristics of ionic liquid polyion liquid polymers from the problem of structural stability of template DNA. The monomer is used for preparing a DNA imprinting material, and can stably imprint template DNA in an imprinting process, so that the construction of the high-identification DNA imprinting material is finally realized.
Detailed Description
The technical solutions of the present invention will be described clearly and completely with reference to specific embodiments of the present invention, and it should be understood that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The invention realizes the construction of the high-identification DNA imprinting material simultaneously comprising a functional area and a cross-linking area through the design of the block macromolecular chain monomer. The method specifically comprises the following steps:
1. preparation of block macromolecular chain monomer
1) An amount of O-ethyl-S- (1-phenylethyl) dithiocarbonate as a Chain Transfer Agent (CTA) and an amount of brominated 1-butyl-3-vinylimidazole ([ BVIM ] Br) were dissolved in a N, N-Dimethylsulfoxide (DMSO) solution (ensuring a total monomer concentration of 2-20% mg/mL), followed by adding an amount of azobisisobutyronitrile initiator (AIBN weight as an initiator of 0.5-2% wt of the total monomer weight) to the mixed solution. Wherein the molar ratio of CTA to [ BVIM ] Br is 1.
2) Introducing nitrogen into the mixed solution to remove oxygen for 30min, and reacting at 60-80 ℃ for 1-18h. The reacted solution was precipitated in 50-100mL of ethyl ether and washed several times with 200mL of ethyl ether. And drying the precipitated product at room temperature for 12h under a vacuum condition to obtain the block macromolecular chain transfer agent.
3) 200mg of block macromolecular chain transfer agent was taken up in an amount of DMSO ensuring a total monomer concentration of 2-20 mg/mL, and then to the solution were added an amount of 4-Chloromethylstyrene (CMS) and azobisisobutyronitrile initiator (the initiator AIBN weight represents 0.5-2% by weight of the total monomer weight). Wherein, the molar ratio of the macromolecular chain transfer agent to the CMS is 1.
4) Introducing nitrogen into the mixed solution of the functional macromolecular chain transfer agent to remove oxygen for 30min, and reacting for 2-24h at 60-80 ℃. The reacted solution was precipitated in 100mL of ethyl ether and washed several times with 200mL of ethyl ether. And drying the precipitated product at room temperature for 12h under a vacuum condition to obtain a precursor of the block macromolecular chain.
5) And (3) carrying out alkylation reaction (12-50 h) on the obtained macromolecular chain precursor and vinyl imidazole at 50 ℃ (solvent DMSO) to obtain the final functional macromolecular chain monomer. The mass ratio of the block macromolecular chain precursor to the vinyl imidazole is 1.5-2. The precipitated crude product was dissolved in 10mL of deionized water, and the aqueous solution was dialyzed for 2 days in a dialysis bag having a molecular weight cut-off of 1000. And (4) freeze-drying the dialyzed aqueous solution to obtain the final block macromolecular chain monomer.
2. Preparation of DNA imprinting hydrogel based on block macromolecular chain monomer
1) 100mg of DNA was assembled with 100-500 mg of functional macromolecular chains in 1-10 mL (ensuring gel solid content between 5% -30% wt) of phosphate buffer (pH =7, 10 mM) for 2h.
2) Then, an amount of ammonium persulfate was dissolved in the above solution, and oxygen was removed by introducing nitrogen for 30min. A certain amount of tetramethylethylenediamine was quickly added to the solution. The mixed solution reacts for 3 to 18 hours at a temperature of between 15 and 30 ℃.
Wherein ammonium persulfate and tetramethylethylenediamine account for 0.5 to 2% by weight of the total monomer mass, the ratio of ammonium sulfate and tetramethylethylenediamine is 1
3) Washing the generated imprinted hydrogel in NaCl solution with the concentration range of 0.1-0.5M at 15-30 ℃, measuring the characteristic peak of the eluent at 280nm by using an ultraviolet spectrophotometer, and continuing the washing process until the characteristic peak at 280nm cannot be observed in the ultraviolet spectrum of the eluent. Then, 1L of deionized water was used to elute NaCl from the surface of the hydrogel. The obtained blotting hydrogel was dried in a vacuum oven at 30 ℃ for 24 to 48 hours. The preparation of non-imprinted hydrogels (NIH) was identical to the above-described imprinted hydrogels (MIH) except that no template DNA molecule was added.
Example 1
1. Preparation of block macromolecular chain monomer
1) 25mg of O-ethyl-S- (1-phenylethyl) dithiocarbonate as a chain transfer agent (CTA, mn =226 g/mol) and 1227mg of brominated 1-butyl-3-vinylimidazole ([ BVIM ] Br, mn =231 g/mol) were dissolved in 10mL of a solution of N, N-dimethyl sulfoxide (DMSO), followed by addition of 12mg of azobisisobutyronitrile initiator to the mixed solution.
2) And introducing nitrogen into the mixed solution to remove oxygen for 30min, and reacting at 60 ℃ for 18h. The reacted solution was precipitated in 100mL of iced ether and washed with 200mL of ether several times. And drying the precipitated product for 12 hours under the vacuum condition at normal temperature to obtain the block macromolecular chain transfer agent.
3) 500mg of the block macromolecular chain transfer agent was dissolved in 10mL of DMSO, and 300mg of the para-CMS and 6mg of azobisisobutyronitrile initiator were added to the solution.
4) And introducing nitrogen into the obtained mixed solution to remove oxygen for 30min, and reacting at 60 ℃ for 18h. The reacted solution was precipitated in 100mL of ethyl ether and washed several times with 200mL of ethyl ether. And drying the precipitated product for 12 hours under the vacuum condition at normal temperature to obtain the precursor of the block macromolecular chain.
5) Further, 500mg of the obtained macromolecular chain precursor and 200mg of vinyl imidazole and 5mL of DMSO are subjected to alkylation reaction at 50 ℃, the solution after the reaction is precipitated in 100mL of ethyl acetate, and the solution is washed for multiple times by 200mL of ethyl acetate. The precipitated crude product was dissolved in 10mL of deionized water, and the aqueous solution was placed in a dialysis bag with a molecular weight cut-off of 1000 for dialysis for 2 days. Freeze drying the dialyzed water solution to obtain the final block macromolecular chain monomer
2. Preparation of DNA imprinting hydrogel based on block macromolecular chain monomer
1) 200mg of DNA was assembled with 200mg of functional macromonomer in 4mL of phosphate buffered solution (pH =7, 10 mM) for 2h.
2) Subsequently, 8mg of ammonium persulfate was dissolved into the above solution, and oxygen was removed by introducing nitrogen for 30min. To the solution was added 8. Mu.L of tetramethylethylenediamine quickly. The solution was reacted at 15 ℃ for 6 hours.
3) The generated imprinted hydrogel is washed in NaCl solution with the concentration range of 0.1-0.5M at 15 ℃, the characteristic peak of the eluent at 280nm is measured by an ultraviolet spectrophotometer, and the washing process is continued until the characteristic peak at 280nm cannot be observed in the ultraviolet spectrum of the eluent. Then, 1L of deionized water was used to elute NaCl from the surface of the hydrogel. The obtained blotting hydrogel was dried in a vacuum oven at 30 ℃ for 24 to 48 hours.
Example 2
1. Preparation of block macromolecular chain monomer
1) 25mg of O-ethyl-S- (1-phenylethyl) dithiocarbonate as a Chain Transfer Agent (CTA) and 1840mg of brominated 1-butyl-3-vinylimidazole ([ BVIM ] Br) were dissolved in 10mL of a solution of N, N-dimethyl sulfoxide (DMSO), followed by addition of 20mg of azobisisobutyronitrile initiator to the mixed solution.
2) And introducing nitrogen into the mixed solution to remove oxygen for 30min, and reacting at 73 ℃ for 3h. The reacted solution was precipitated in 100mL of ethyl ether and washed several times with 200mL of ethyl ether. And drying the precipitated product for 12 hours at room temperature under vacuum condition to obtain the block macromolecular chain transfer agent.
3) 500mg of the block macromolecular chain transfer agent was dissolved in 10mL of DMSO, and 150mg of the para-CMS and 5mg of azobisisobutyronitrile initiator were added to the solution.
4) The obtained mixed solution is introduced with nitrogen to remove oxygen for 30min, and then reacts for 3h at 73 ℃. The reacted solution was precipitated in 100mL of ethyl ether and washed several times with 200mL of ethyl ether. And drying the precipitated product for 12 hours under the vacuum condition at normal temperature to obtain a precursor of the block macromolecular chain.
5) Further, 500mg of the obtained precursor of the macromonomer was subjected to alkylation reaction with 120mg of vinylimidazole and 4mL of DMSO at 50 ℃, and the solution after the reaction was precipitated in 100mL of ethyl glacial ether and washed with 200mL of ether several times. The precipitated crude product was dissolved in 10mL of deionized water, and the aqueous solution was placed in a dialysis bag with a molecular weight cut-off of 1000 for dialysis for 2 days. And (4) freeze-drying the dialyzed aqueous solution to obtain the final block macromolecular chain monomer.
2. Preparation of DNA imprinting hydrogel based on block macromolecular chain monomer
1) 100mg of DNA was assembled with 300mg of functional macromonomer in 4mL of phosphate buffered solution (pH =7, 10 mM) for 2h.
2) Subsequently, 8mg of ammonium persulfate was dissolved into the above solution, and oxygen was removed by introducing nitrogen for 30min. To the solution was added immediately 8. Mu.L of tetramethylethylenediamine. The solution was reacted at 15 ℃ for 8 hours.
3) Washing the generated imprinted hydrogel in NaCl solution with the concentration range of 0.1-0.5M at 15 ℃, measuring the characteristic peak of the eluent at 280nm by using an ultraviolet spectrophotometer, and continuing the washing process until the characteristic peak at 280nm cannot be observed in the ultraviolet spectrum of the eluent. Then, 1L of deionized water was used to elute NaCl from the surface of the hydrogel. The obtained blotting hydrogel was dried in a vacuum oven at 30 ℃ for 24 to 48 hours.
Example 3
1. Preparation of block macromolecular chain monomer
1) 25mg of O-ethyl-S- (1-phenylethyl) dithiocarbonate as a Chain Transfer Agent (CTA) and 2425mg of brominated 1-butyl-3-vinylimidazole ([ BVIM ] Br) were dissolved in 10mL of N, N-dimethyl sulfoxide (DMSO) solution, followed by addition of 20mg of azobisisobutyronitrile initiator to the mixed solution.
2) And introducing nitrogen into the mixed solution to remove oxygen for 30min, and reacting at 65 ℃ for 12h. The reacted solution was precipitated in 100mL of ethyl ether and washed several times with 200mL of ethyl ether. And drying the precipitated product at normal temperature for 12h under vacuum condition to obtain the block macromolecular chain transfer agent.
3) 500mg of the block macromolecular chain transfer agent was dissolved in 10mL of DMSO and 400 pairs of CMS and 10mg of azobisisobutyronitrile initiator were added as solution.
4) Introducing nitrogen into the obtained mixed solution, deoxidizing for 30min, and reacting for 12h at 65 ℃. The reacted solution was precipitated in 100mL of ethyl ether and washed several times with 200mL of ethyl ether. And drying the precipitated product for 12 hours under the vacuum condition at normal temperature to obtain the precursor of the block macromolecular chain.
5) Further dissolving 500mg of the obtained macromolecular chain precursor and 350mg of vinyl imidazole in 6mL of DMSO, carrying out alkylation reaction at 50 ℃, precipitating the reacted solution in 100mL of glacial ethyl ether, and washing with 200mL of ethyl ether for multiple times. The precipitated crude product was dissolved in 10mL of deionized water, and the aqueous solution was placed in a dialysis bag with a molecular weight cut-off of 1000 for dialysis for 2 days. And (4) freeze-drying the dialyzed aqueous solution to obtain the final block macromolecular chain monomer.
2. Preparation of DNA imprinting hydrogel based on block macromolecular chain monomer
1) 100mg of DNA was assembled with 500mg of functional macromolecular strands in 10mL of phosphate buffered solution (pH =7, 10 mM) for 2h.
2) Subsequently, 8mg of ammonium persulfate was dissolved into the above solution, and oxygen was removed by introducing nitrogen for 30min. To the solution was added immediately 8. Mu.L of tetramethylethylenediamine. The solution was reacted at 15 ℃ for 18 hours.
3) Washing the generated imprinted hydrogel in NaCl solution with the concentration range of 0.1-0.5M at 15 ℃, measuring the characteristic peak of the eluent at 280nm by using an ultraviolet spectrophotometer, and continuing the washing process until the characteristic peak at 280nm cannot be observed in the ultraviolet spectrum of the eluent. Then, 1L of deionized water was used to elute NaCl from the surface of the hydrogel. The obtained blotting hydrogel was dried in a vacuum oven at 30 ℃ for 24 to 48 hours.
Although embodiments of the present invention have been shown and described, it will be appreciated by those skilled in the art that changes, modifications, substitutions and alterations can be made in these embodiments without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.
Claims (7)
1. A preparation method of a DNA imprinting material based on a block macromolecular chain monomer is characterized by comprising the following steps:
1) Dissolving O-ethyl-S- (1-phenethyl) dithiocarbonate and brominated 1-butyl-3-vinyl imidazole in an organic solvent, adding an initiator, and reacting under an anaerobic condition to obtain a macromolecular chain transfer agent;
2) Respectively adding a macromolecular chain transfer agent, 4-chloromethyl styrene and an initiator into an organic solvent, and reacting under an anaerobic condition to obtain a block macromolecular chain precursor;
3) Performing alkylation reaction on the block macromolecular chain precursor and vinyl imidazole, and putting the product into a dialysis bag for dialysis to obtain a final functional block macromolecular chain monomer;
4) And (3) placing the DNA and the block macromolecular chain monomer in a phosphoric acid buffer solution for assembly, sequentially adding ammonium persulfate and tetramethylethylenediamine, and reacting under an anaerobic condition to obtain the DNA imprinting hydrogel.
2. The method for preparing the southern blotting material based on the block macromonomer according to claim 1, wherein the molar ratio of O-ethyl-S- (1-phenylethyl) dithiocarbonate to brominated 1-butyl-3-vinylimidazole is 1.
3. The method for preparing a southern blotting material based on a block macromonomer according to claim 1, wherein the molar ratio of the macromolecular chain transfer agent to 4-chloromethylstyrene is 1 to 10 to 100.
4. The method for preparing a DNA imprinting material based on a block macromolecular chain monomer according to claim 1, characterized in that the mass ratio of the block macromolecular chain precursor to vinylimidazole is 1.5-2.
5. The method for preparing the southern blotting material based on the block macromonomer according to claim 1, wherein the mass ratio of the DNA to the functional block macromonomer is 1 to 5.
6. The method for preparing a block macromonomer-based southern blotting material as claimed in claim 1, wherein the organic solvent is N, N-dimethyl sulfoxide; the initiator is azobisisobutyronitrile.
7. A southern blot hydrogel prepared by the preparation method of claim 1.
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| CN103833915A (en) * | 2012-11-20 | 2014-06-04 | 南开大学 | Molecular imprinting polymer nanoparticles for pure biological sample, and preparation method thereof |
| CN106317335A (en) * | 2015-07-01 | 2017-01-11 | 南开大学 | Molecularly imprinted polymer sensing material suitable for biological samples and preparation method of sensing material |
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| CN103833915A (en) * | 2012-11-20 | 2014-06-04 | 南开大学 | Molecular imprinting polymer nanoparticles for pure biological sample, and preparation method thereof |
| CN106317335A (en) * | 2015-07-01 | 2017-01-11 | 南开大学 | Molecularly imprinted polymer sensing material suitable for biological samples and preparation method of sensing material |
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