CN108107144B - Aptamer functionalized POSS (polyhedral oligomeric silsesquioxane) crosslinked organic-silica gel hybrid monolithic column and preparation method thereof - Google Patents
Aptamer functionalized POSS (polyhedral oligomeric silsesquioxane) crosslinked organic-silica gel hybrid monolithic column and preparation method thereof Download PDFInfo
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Abstract
The invention discloses a POSS (polyhedral oligomeric silsesquioxane) cross-linked organic-silica gel hybrid polymerization monolithic column functionalized by an aptamer and a preparation method thereof. The monolithic column is an affinity monolithic column which is directly prepared by dissolving a high-hydrophilicity organic polymeric monomer, a cage-type oligomeric silsesquioxane cross-linking agent, an acrylate cross-linking agent, a nucleic acid aptamer aqueous solution and an initiator through a ternary pore-forming agent to form a uniform solution, and injecting the uniform solution into the column to synchronously perform free radical thermal initiation polymerization and 'mercapto-alkene' click chemical reaction; the ternary pore-foaming agent is a mixed solution consisting of three components of water-N, N-dimethylformamide-PEG 10000. The aptamer is efficiently bonded by a covalent bond through a one-step method, and the prepared affinity monolithic column has a stable structure, is simple and quick, and is suitable for specific identification and separation of ochratoxin A.
Description
Technical Field
The invention belongs to the field of analytical chemistry, and particularly relates to a POSS (polyhedral oligomeric silsesquioxane) cross-linked organic-silica gel hybrid polymerization monolithic column functionalized by a nucleic acid aptamer and a preparation method thereof.
Background
The aptamer modified affinity monolithic column is used as a novel affinity action separation material, is attracted by researchers, and is successfully applied to separation of small molecular compounds, proteins and cells. The aptamer is combined with the monolithic column material to prepare the high-efficiency novel affinity-action stationary phase material, the advantages of the aptamer and the monolithic column material are fully exerted, and compared with immune antibody affinity chromatography, the aptamer-based affinity-action stationary phase material has the advantages of easiness in immobilization, easiness in keeping conformation, high coverage rate of the surface of the stationary phase, good stability, easiness in renaturation after deformation and the like.
Usually, the aptamer needs to be immobilized on the monolithic column by a specific method, and a more mature method is to immobilize the aptamer on the stationary phase based on the bridging action between biotin and streptavidin,the method has the advantages of mild preparation conditions, high yield, and the like, and is favorable for keeping the activity of the aptamer. ZHao et al use the bridging effect between biotin and streptavidin to modify the aptamer on an organic polymer monolithic column to prepare a aptamer affinity monolithic column and realize the separation and detection of thrombin (Zhao et al: (Anal. Chem., 2008, 80: 7586-7593). Recently, the research work of aptamer modified affinity monolithic column has been reported newly, Zhang et al prepared aminated organic-inorganic hybrid monolithic column, and the aptamer with amino group modified at the end was chemically bonded to the hybrid monolithic column through glutaraldehyde to realize the separation, purification and detection of target protein: (Anal. Chem2012, 84, 10186-; wang et al prepared a substrate column with an ethylenic unsaturation on the surface by a sol-gel method, and bound a thiol-modified aptamer to the substrate column by thiol-ene click chemistry to prepare an aptamer-modified monolithic column (aptamer-modified monolithic column)Talanta, 2015, 138: 52-58). These methods generally require post-column modification procedures, which are tedious in steps and time-consuming.
The polyhedral oligomeric silsesquioxane has a unique cage structure, has good compatibility with polymers and organic monomers on the size of a nano structure, is blended into a conventional organic polymer by a copolymerization, grafting or mixing method, and effectively improves the mechanical strength and stability of the original polymer. The polyhedral oligomeric silsesquioxane grafted by methacrylate is introduced as a cross-linking agent and has been due to a plurality of POSS-based cross-linked polymeric monolithic columns, but the prior research is mainly applied to a hydrophobic reaction system or a pore-foaming agent system adopting a large amount of organic reagents, and the problem of incompatibility of the POSS hydrophobic cross-linking agent and an aptamer aqueous solution still exists. The research for preparing the aptamer modified POSS cross-linked polymerized organic-silica gel hybrid monolithic column based on the one-step method has not been reported so far.
Disclosure of Invention
The invention aims to provide an aptamer functionalized POSS cross-linked organic-silica gel hybrid monolithic column and a preparation method thereof, aiming at the defects of the prior art. The monolithic column realizes high compatibility of four components of a high-hydrophilicity organic polymeric monomer, a cage-type oligomeric silsesquioxane (POSS) cross-linking agent, an acrylate cross-linking agent and a nucleic acid aptamer by a pore-foaming agent in a one-step polymerization mode, and directly bonds the nucleic acid aptamer to the monolithic column by utilizing the simultaneous generation of free radical thermal initiation polymerization and sulfydryl-ene click chemical reaction in the column, so that the fast, high-efficiency and stable preparation of the affinity monolithic column is realized; the obtained aptamer-modified affinity monolithic column can realize high-efficiency recognition of a target substance specifically bound by the aptamer.
In order to achieve the purpose, the invention adopts the following technical scheme:
a nucleic acid aptamer functionalized POSS (polyhedral oligomeric silsesquioxane) crosslinked organic-silica gel hybrid monolithic column is an affinity monolithic column which is directly prepared by dissolving a high-hydrophilicity organic polymerization monomer, a cage-type oligomeric silsesquioxane crosslinking agent, an acrylate crosslinking agent, a nucleic acid aptamer aqueous solution and an initiator through a ternary pore-foaming agent to form a uniform solution, injecting the uniform solution into the column and synchronously performing free radical thermal initiation polymerization and 'sulfydryl-ene' click chemical reaction; the ternary pore-foaming agent is a mixed solution consisting of three components of water-N, N-dimethylformamide-PEG 10000.
The pore-foaming agent comprises the following components in percentage by mass: 0.5 to 5.5 percent of water, 100004.3 percent of PEG, 90.2 to 95.2 percent of N, N-dimethylformamide, and the sum of the mass fractions of the components is 100 percent.
The high-hydrophilicity organic monomer is a 2-acrylamide-2-methylpropanesulfonic acid monomer; the cage type oligomeric silsesquioxane cross-linking agent is polyhedral oligomeric silsesquioxane grafted by methacrylate; the acrylate cross-linking agent is ethylene glycol dimethacrylate; the initiator is azodiisobutyronitrile; the aptamer is an anti-ochratoxin A aptamer.
The mass ratio of the high hydrophilic organic polymeric monomer to the cage type oligomeric silsesquioxane cross-linking agent to the acrylate cross-linking agent is as follows: 12.5:3.75: 83.75; the amount of the initiator accounts for 1.0wt% of the total amount of the monomer and the crosslinking agent; the molar amount of thiol-modified aptamer was 2.4 nmol.
The aptamer base sequence of the anti-ochratoxin A is 5' -SH-C6-GAT CGG GTG TGG GTGGCG TAA AGG GAG CAT CGG ACA.
A method of preparing an aptamer-functionalized POSS cross-linked organo-silica hybrid monolithic column as described above, comprising the steps of:
(1) centrifuging the sulfhydryl-modified aptamer for 5 minutes at 8000r/min, adding water to dilute the sulfhydryl-modified aptamer to 1000 mu mol/L, heating the sulfhydryl-modified aptamer for 3 minutes at 90 ℃, and cooling the sulfhydryl-modified aptamer to room temperature to form aptamer stock solution 1;
(2) adding a 2-acrylamide-2-methylpropanesulfonic acid monomer, methacrylate-grafted polyhedral oligomeric silsesquioxane, ethylene glycol dimethacrylate and azobisisobutyronitrile into a centrifugal tube, adding a ternary pore-forming agent into the centrifugal tube, uniformly mixing, adding a 2.4-microliter aptamer stock solution 1, carrying out vortex oscillation at room temperature for 20min, and carrying out ultrasonic degassing for 20min to form a uniform solution 2;
(3) injecting the obtained solution 2 into a quartz capillary column pretreated by 3- (methacryloyloxy) propyl trimethoxy silane at room temperature, sealing two ends, and immersing in 55 ℃ water bath for continuous reaction for 12 hours; after the reaction is finished, taking out the prepared monolithic column, connecting the monolithic column to a high-pressure pump of a liquid chromatography solvent, and washing the monolithic column by using a methanol aqueous solution (v: v =1: 1) until the pressure is stable;
(4) and (4) introducing the buffer solution into the monolithic column prepared in the step (3), and storing at the temperature of 4 ℃. The buffer solution is composed of 10mmol/L Tris-HCl with pH of 8.5, 120 mmol/L NaCl, 5mmol/L KCl and 20mmol/L CaCl2And (4) forming.
The invention has the advantages that:
(1) according to the invention, ternary pore-foaming agent water, N-dimethylformamide and PEG10000 are adopted, so that the aptamer is completely compatible with an organic polymerization monomer, a hydrophobic POSS cross-linking agent and a hydrophobic methacrylate cross-linking agent system, and the reaction system is uniform and stable;
(2) the invention directly prepares and forms the affinity monolithic column by synchronously generating free radical thermal initiation polymerization and 'sulfydryl-alkene' click chemical reaction in the column, the nucleic acid aptamer with the sulfydryl modified at the tail end is directly bonded on the monolithic column by one step through the 'click chemical' reaction, compared with the affinity monolithic column which fixes the nucleic acid aptamer by chemical bonding in other modes, the preparation is rapid, the influence of polymerization inhibitors such as water, oxygen and the like is small, and the reaction condition is mild;
(3) the methacrylate-grafted polyhedral oligomeric silsesquioxane disclosed by the invention has a unique inorganic-organic doped compound with a nano size and a cage-like structure, has good compatibility with a polymer and an organic monomer in the nano structure size due to an organic functional group, is used as a cross-linking agent together with ethylene glycol dimethacrylate, has more action sites with a terminal modified sulfhydryl aptamer, and has good swelling resistance of an integral column.
Drawings
In FIG. 1, (a) is the recognition of ochratoxin A by a blank column (unmodified aptamer), (b) is the recognition of ochratoxin A by a control column (modified non-OTA aptamer);
FIG. 2 specific recognition of ochratoxin A by aptamer affinity column (modified OTA aptamer), peak 1 is ochratoxin A.
Detailed Description
In order to make the present invention more comprehensible, the technical solutions of the present invention are further described below with reference to specific embodiments, but the present invention is not limited thereto.
Example 1
A preparation method of an aptamer functionalized POSS cross-linked organic-silica gel hybrid monolithic column comprises the following specific steps:
(1) centrifuging the sulfhydryl-modified aptamer for 5 minutes at 8000r/min, adding water to dilute the sulfhydryl-modified aptamer to 1000 mu mol/L, heating the sulfhydryl-modified aptamer for 3 minutes at 90 ℃, and cooling the sulfhydryl-modified aptamer to room temperature to form aptamer stock solution 1;
(2) according to the mass ratio of 12.5:3.75:83.75, 2-acrylamide-2-methylpropanesulfonic acid monomer, methacrylate-grafted polyhedral oligomeric silsesquioxane and ethylene glycol dimethacrylate are accurately weighed and added into a centrifuge tube, the amount of the initiator is accurately added to account for 1.0wt% of the total amount of the monomer and the cross-linking agent, then the pore-forming agent is proportionally PEG10000 to account for 4.3% of the total amount of the pore-forming agent, water to account for 0.5% (column 1), 2.5% (column 2), 5.0% (column 3) and 5.5% (column 4) of the total amount of the pore-forming agent respectively, corresponding to N, N-dimethylformamide to account for 95.2% (column 1), 93.2% (column 2), 90.7% (column 3) and 90.2% (column 4) of the pore-forming agent, the mixture is sequentially added into a 2.0 mL centrifuge tube, after uniform mixing, nucleic acid aptamer solution 1 with the volume of 2.4 muL is added, the mixture is subjected to oscillation at room temperature for 20min and ultrasonic degassing for 20min, so that a uniform solution 2 is formed;
(3) injecting the obtained solution 2 into a quartz capillary column pretreated by 3- (methacryloyloxy) propyl trimethoxy silane at room temperature, sealing two ends, and immersing in 55 ℃ water bath for continuous reaction for 12 hours; after the reaction is finished, taking out the prepared monolithic column, connecting the monolithic column to a high-pressure pump of a liquid chromatography solvent, and washing the monolithic column by using a methanol aqueous solution (v: v =1: 1) until the pressure is stable;
(4) and (4) introducing the buffer solution into the monolithic column prepared in the step (3), and storing at the temperature of 4 ℃. The buffer solution is composed of 10mmol/L Tris-HCl with pH of 8.5, 120 mmol/L NaCl, 5mmol/L KCl and 20mmol/L CaCl2And (4) forming.
Example 2
A blank column, a control column and an aptamer affinity column (column 3 is taken as an example), wherein the length of the affinity column is 10cm, and the method is implemented according to the following steps: (1) balancing: equilibrating with binding buffer solution (10 mmol/L Tris-HCl, 120 mmol/L NaCl, 5mmol/L KCl and 20mmol/L CaCl) for 0.5 hr under chromatographic conditions of flow rate of 0.10 mL/min and pressure of 250psi2pH 8.50; (2) enrichment: injecting 20 μ L10 ng/mL ochratoxin A solution respectively, enriching on the whole column for 1 hr, with chromatographic condition of 0.02 mL/min and pressure of 250 psi; (3) cleaning: loading the enrichment column on a liquid chromatography pump, and respectively cleaning the blank column, the control column and the aptamer affinity monolithic column by using a binding buffer solution; the cleaning conditions are that the flow rate is 0.1 mL/min, the pressure is 500psi, and the final cleaning solution is collected to be checked; (4) and (3) elution: with 30% ACN: 70% TE buffer (10 mM Tris-HCl pH8.5, 2.5mM EDTA) as eluent to elute OTA from the monolithic columnNext, a 250psi back pressure valve, flow rate 0.05mL/min collected 0.5 hours of eluate for examination. The pool was checked on an HPLC-fluorescence detector and no effective retention of ochratoxin A was seen for the blank and control columns (a, b in FIG. 1).
Aptamer affinity monolithic column was applied, using 30% ACN: 70% TE buffer (10 mM Tris-HCl pH8.5, 2.5mM EDTA) was used as eluent, OTA was eluted efficiently (FIG. 2), and the elution peaks in FIG. 1 are: 1. ochratoxin a (ota).
The above description is only a preferred embodiment of the present invention, and all equivalent changes and modifications made in accordance with the claims of the present invention should be covered by the present invention.
Sequence listing
<110> Fuzhou university
<120> aptamer functionalized POSS (polyhedral oligomeric silsesquioxane) crosslinked organic-silica gel hybrid monolithic column and preparation method thereof
<130>1
<160>1
<170>SIPOSequenceListing 1.0
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<213> Artificial sequence (analysis sequence)
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shcgatcggg tgtgggtggc gtaaagggag catcggaca 39
Claims (6)
1. An aptamer functionalized POSS cross-linked organic-silica gel hybrid monolithic column, which is characterized in that: the monolithic column is an affinity monolithic column which is directly prepared by dissolving a high-hydrophilicity organic polymeric monomer, a cage-type oligomeric silsesquioxane cross-linking agent, an acrylate cross-linking agent, a nucleic acid aptamer aqueous solution and an initiator through a ternary pore-forming agent to form a uniform solution, and injecting the uniform solution into the column to synchronously perform free radical thermal initiation polymerization and 'mercapto-alkene' click chemical reaction; the preparation method specifically comprises the following steps:
(1) centrifuging the sulfhydryl-modified aptamer for 5 minutes at 8000r/min, adding water to dilute the sulfhydryl-modified aptamer to 1000 mu mol/L, heating the sulfhydryl-modified aptamer for 3 minutes at 90 ℃, and cooling the sulfhydryl-modified aptamer to room temperature to form aptamer stock solution 1;
(2) adding a 2-acrylamide-2-methylpropanesulfonic acid monomer, methacrylate-grafted polyhedral oligomeric silsesquioxane, ethylene glycol dimethacrylate and azobisisobutyronitrile into a centrifugal tube, adding a ternary pore-forming agent into the centrifugal tube, uniformly mixing, adding a 2.4-microliter aptamer stock solution 1, carrying out vortex oscillation at room temperature for 20min, and carrying out ultrasonic degassing for 20min to form a uniform solution 2;
(3) injecting the obtained solution 2 into a quartz capillary column pretreated by 3- (methacryloyloxy) propyl trimethoxy silane at room temperature, sealing two ends, and immersing in 55 ℃ water bath for continuous reaction for 12 hours; taking out the prepared monolithic column after the reaction is finished, connecting the monolithic column to a high-pressure pump of a liquid chromatography solvent, and cleaning the monolithic column by using a methanol aqueous solution until the pressure is stable, wherein the volume ratio of methanol to water in the methanol aqueous solution is 1: 1;
(4) and (4) introducing the buffer solution into the monolithic column prepared in the step (3), and storing at the temperature of 4 ℃.
2. The aptamer-functionalized POSS cross-linked organo-silica hybrid monolithic column of claim 1, wherein: the ternary pore-foaming agent comprises the following components in percentage by mass: 90.2 to 95.2 percent of N, N-dimethylformamide, 0.5 to 5.5 percent of PEG-100004.3 percent of water, and the sum of the mass fractions of the components is 100 percent.
3. The aptamer-functionalized POSS-crosslinked organo-silica hybrid monolithic column of claim 1, wherein: the high-hydrophilicity organic polymeric monomer is a 2-acrylamide-2-methylpropanesulfonic acid monomer; the cage type oligomeric silsesquioxane cross-linking agent is polyhedral oligomeric silsesquioxane grafted by methacrylate; the acrylate cross-linking agent is ethylene glycol dimethacrylate; the initiator is azodiisobutyronitrile; the aptamer is an anti-ochratoxin A aptamer.
4. The aptamer-functionalized POSS-crosslinked organo-silica hybrid monolithic column of claim 1, wherein: the mass ratio of the high-hydrophilic organic polymerization monomer to the cage-type oligomeric silsesquioxane cross-linking agent to the acrylate cross-linking agent is 12.5:3.75: 83.75; the amount of the initiator accounts for 1.0wt% of the total amount of the monomer and the crosslinking agent; the molar amount of thiol-modified aptamer was 2.4 nmol.
5. The aptamer-functionalized POSS-crosslinked organo-silica hybrid monolithic column according to claim 3, wherein: the aptamer base sequence of the anti-ochratoxin A is 5' -SH-C6-GAT CGG GTG TGGGTG GCG TAA AGG GAG CAT CGG ACA.
6. The aptamer-functionalized POSS-crosslinked organo-silica hybrid monolithic column of claim 1, wherein: the buffer solution in the step (4) consists of 10mmol/L Tris-HCl with pH of 8.5, 120 mmol/L NaCl, 5mmol/L KCl and 20mmol/L CaCl2And (4) forming.
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| CN109342626A (en) * | 2018-11-28 | 2019-02-15 | 福州大学 | POSS organic-inorganic hybrid molecule trace integral post of specific recognition ochratoxin A and preparation method thereof |
| CN110102270B (en) * | 2019-06-03 | 2021-06-01 | 福州大学 | Aptamer affinity monolithic column for specifically recognizing F2 toxin and preparation method thereof |
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| CN110605104A (en) * | 2019-08-08 | 2019-12-24 | 福州大学 | Aptamer-imprinted monolithic column for specifically recognizing ochratoxin A and preparation method thereof |
| CN111135805B (en) * | 2020-01-21 | 2023-03-21 | 福州大学 | Aptamer functional extraction material for adsorbing phthalate, and preparation method and application thereof |
| CN111821961A (en) * | 2020-07-24 | 2020-10-27 | 福州大学 | High-hydrophilicity aptamer functional extraction material and application thereof |
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| CN113773453B (en) * | 2021-09-22 | 2023-07-14 | 北方民族大学 | Hydrophilic chromatographic stationary phase of graft copolymer brush on POSS silica gel, and preparation method and application thereof |
| CN115504559B (en) * | 2022-10-31 | 2023-08-08 | 肇庆旭源环保科技有限公司 | Preparation method of all-organic composite sewage flocculant microspheres |
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