CN108107144A - A kind of POSS of aptamer functionalization is crosslinked organic-silica gel hybridization integral post and preparation method thereof - Google Patents
A kind of POSS of aptamer functionalization is crosslinked organic-silica gel hybridization integral post and preparation method thereof Download PDFInfo
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- CN108107144A CN108107144A CN201711480316.5A CN201711480316A CN108107144A CN 108107144 A CN108107144 A CN 108107144A CN 201711480316 A CN201711480316 A CN 201711480316A CN 108107144 A CN108107144 A CN 108107144A
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- G—PHYSICS
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- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
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- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/10—Selective adsorption, e.g. chromatography characterised by constructional or operational features
- B01D15/22—Selective adsorption, e.g. chromatography characterised by constructional or operational features relating to the construction of the column
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- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/26—Selective adsorption, e.g. chromatography characterised by the separation mechanism
- B01D15/38—Selective adsorption, e.g. chromatography characterised by the separation mechanism involving specific interaction not covered by one or more of groups B01D15/265 - B01D15/36
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- B01D15/3819—Affinity chromatography of the nucleic acid-nucleic acid binding protein type
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Abstract
POSS cross-linked silicone glue hybrid polymer integral posts the invention discloses a kind of aptamer functionalization and preparation method thereof.The integral post is by high hydrophilic organic polymerized monomer, polyhedral oligomeric sesquialter multi-polysiloxane crosslinking agent, acrylate cross linked dose and aptamer aqueous solution and initiator, it dissolves to form homogeneous solution by ternary pore-foaming agent, injects in column and free radical thermal-initiated polymerization and the reaction of " sulfydryl alkene " click chemistry synchronously occurs and directly prepares the affine integral post of formation；The ternary pore-foaming agent is 10,000 3 kinds of water N, N dimethylformamide PEG into the mixed solution be grouped into.Amplifying nucleic acid aptamers of the present invention are bonded by one-step method with covalent bond high efficiency, and prepared affine integral post stable structure, method is simple and quick, are separated suitable for the specific recognition of ochratoxin A.
Description
Technical field
The invention belongs to analytical chemistry fields, and in particular to a kind of POSS of aptamer functionalization is crosslinked organic-silicon
Glue hybrid polymer integral post and preparation method thereof.
Background technology
Aptamer modified affine integral post has obtained researcher as a kind of new affinity interaction separation material
Concern, be successfully applied in separation micromolecular compound, protein and cell.Aptamer is mutually tied with Monolithic Columns
It closes, prepares the affinity interaction stationary phase material of new high-efficiency, the advantage of the two is given full play to, with immune antiboidy affinity chromatography phase
Than, have easily fixing, easily keep conformation, the coverage rate of fixed phase surface is high, stability is good, easy renaturation etc. after deformation
Advantage.
Normal conditions, aptamer needs are immobilized on by specific mode in integral post, and the mode of comparative maturity is
Aptamers are fixed in stationary phase based on the bridge linking effect between biotin and Streptavidin, this method preparation condition temperature
It is high with yield, the advantages that being conducive to keep the activity of aptamers.Zhao etc. utilizes the bridging between biotin and Streptavidin
Effect by aptamers modification to Organic Polymer Monolithic Columns, is prepared for the affine integral post of aptamer, and realizes to solidifying
The separation and detection of hemase（Anal. Chem., 2008, 80: 7586-7593）.In recent years, aptamer modified parent
Research work with integral post has new report, and Zhang etc. prepares amidized organic-inorganic hybridization monolithic column, by end
The aptamer for being modified to amino is chemically bonded to by glutaraldehyde in hydridization integral post, realizes and target protein is divided
From purifying and detection（Anal. Chem., 2012, 84, 10186-10190）；Wang etc. is prepared for by sol-gel method
Surface carries the matrix column of unsaturated ethylene linkage, is reacted using sulfydryl-alkene clicking chemistry by the aptamer of end modified sulfydryl
It is bonded on matrix column, is prepared for aptamer modified integral post（Talanta, 2015, 138: 52-58）.These sides
Method generally needs modification after column, and complex steps, time-consuming.
Polyhedral oligomeric sesquialter silane has unique cage structure, with polymer and organic monomer in nanostructured ruler
There is good compatibility on very little, be admixed in conventional organic polymers, effectively improved by the method for being copolymerized, grafting or mix
The mechanical strength and stability of original copolymer.It introduces methacrylate and connects the polyhedral oligomeric silsesquioxane of branch as crosslinking
Agent obtains to have in multiple POSS bases cross-linked polymeric integral posts, but research mainly in hydrophobicity reaction system or is adopted at present
It is applied in the pore-foaming agent system of a large amount of organic reagents, the incompatibility problem of POSS hydrophobic crosslinking agents and aptamers aqueous solution is still
So exist.Based on one-step method prepare aptamer modified POSS cross-linked polymerics it is organic-research of silica gel hybridization integral post extremely
It is modern that there is not been reported.
The content of the invention
In view of the above-mentioned deficiencies in the prior art, it is an object of the present invention to provide a kind of POSS crosslinkings of aptamer functionalization
Organic-silica gel hybridization integral post and preparation method thereof.The integral post is real using pore-foaming agent by way of " one-step polymerization "
Existing high hydrophilic organic polymerized monomer, polyhedral oligomeric sesquialter multi-polysiloxane（POSS）Crosslinking agent, acrylate cross linked dose and nucleic acid
The highly compatible of four kinds of components of aptamers, using free radical thermal-initiated polymerization and " sulfydryl-alkene " click chemistry synchronously occur in column
It reacts and directly aptamer is led to and is covalently bound in integral post, realize quick, the affine integral post of high efficiency, stabilization
It prepares；Obtained aptamer modified affine integral post can realize the height of the object to aptamer specific bond
Effect identification.
To achieve these goals, the present invention adopts the following technical scheme that：
The POSS of aptamer functionalization a kind of is crosslinked organic-silica gel hybridization integral post, be by high hydrophilic organic polymerized monomer,
Polyhedral oligomeric sesquialter multi-polysiloxane crosslinking agent, acrylate cross linked dose and aptamer aqueous solution and initiator, pass through three
First pore-foaming agent dissolves to form homogeneous solution, injects in column and free radical thermal-initiated polymerization and " sulfydryl-alkene " clickization synchronously occurs
It learns reaction and directly prepares the affine integral post of formation；The ternary pore-foaming agent is water-N,N-dimethylformamide-PEG
10000 3 kinds into the mixed solution be grouped into.
The dosage of pore-foaming agent each component is as mass fraction：Water 0.5%-5.5%, PEG 10,000 4.3%, N, N- diformazans
The sum of base formamide 90.2%-95.2%, the above components mass fraction are 100%.
The high hydrophilic organic monomer is 2- acrylamide-2-methyl propane sulfonic monomers；The polyhedral oligomeric sesquialter
Multi-polysiloxane crosslinking agent connects the polyhedral oligomeric silsesquioxane of branch for methacrylate；Described acrylate cross linked dose
For ethylene glycol dimethacrylate；The initiator is azo-bis-isobutyl cyanide；The aptamer is anti-Aspergillus ochraceus
The aptamer of toxin A.
High hydrophilic organic polymerized monomer, polyhedral oligomeric sesquialter multi-polysiloxane crosslinking agent, acrylate cross linked dose of quality
Than for：12.5:3.75:83.75；The dosage of initiator accounts for monomer and the 1.0wt% of crosslinking agent total amount；Mercapto-modified nucleic acid is fitted
The mole of ligand is 2.4nmol.
The aptamer base sequence of the anti-ochratoxin A is 5'-SH-C6-GAT CGG GTG TGG GTG
GCG TAA AGG GAG CAT CGG ACA。
A kind of POSS for preparing aptamer functionalization as described above is crosslinked the side of organic-silica gel hybridization integral post
Method comprises the following steps：
（1）Mercapto-modified aptamer first with the rate of 8000r/min is centrifuged 5 minutes, water is then added in and is diluted to
1000 μm of ol/L are heated 3 minutes in 90 DEG C, and aptamer stock solution 1 is formed after being cooled to room temperature；
（2）2- acrylamide-2-methyl propane sulfonics monomer, methacrylate are first connect to the polyhedral oligomeric silsesquioxane of branch
Alkane, ethylene glycol dimethacrylate and azodiisobutyronitrile are added in centrifuge tube, then by ternary pore-foaming agent add in from
In heart pipe, the aptamer stock solution 1 that volume is 2.4 μ L is added in after mixing, at room temperature 20 min of vortex oscillation,
Ultrasound degassing 20min, forms it into uniform solution 2；
（3）Obtained solution 2 is injected at room temperature and is pre-processed using 3- (methacryloxypropyl) propyl trimethoxy silicane
Quartz capillary column in, both ends sealing after immerse 55 DEG C of water-bath successive reaction 12h；The integral post that will be prepared after the completion of reaction
It takes out, liquid chromatography solvents high-pressure pump is connected to, using methanol aqueous solution（v:v=1:1）Cleaning is until pressure stability；
（4）Buffer solution is passed through step（3）In obtained integral post, preserved at a temperature of 4 DEG C.Buffer solution by pH for 8.5,
10 mmol/L Tris-HCl, 120 mmol/L NaCl, 5 mmol/L KCl and 20mmol/L CaCl2Composition.
The advantage of the invention is that：
（1）The present invention uses ternary pore-foaming agent water, n,N-Dimethylformamide and PEG 10000 so that aptamer is with having
Machine polymerized monomer, hydrophobicity POSS crosslinking agents, hydrophobic methacrylates cross linker system are completely compatible, and reaction system is homogeneous
Stablize；
（2）The present invention is directly made by the way that free radical thermal-initiated polymerization and the reaction of " sulfydryl-alkene " click chemistry synchronously occur in column
Standby to form affine integral post, the aptamer of end modified sulfydryl utilizes " click chemistry " to react a direct step and is bonded to entirety
On column, compared with the affine integral post of other modes chemical bonding fixed nucleic acid aptamers, prepare quickly, be subject to water and oxygen etc.
The influence of polymerization inhibitor is small, and reaction condition is mild；
（3）Methacrylate of the present invention connect branch polyhedral oligomeric silsesquioxane have unique nano-scale and
The inorganic organic blended compound of cage structure, organo-functional group make it with polymer and organic monomer in nanostructure size
On have good compatibility, with ethylene glycol dimethacrylate collectively as crosslinking agent, be adapted to end modified sulfydryl nucleic acid
Body action site is more, and integral post resistance to swelling is good.
Description of the drawings
In Fig. 1（a）For blank column（Unmodified aptamer）Identification to ochratoxin A,（b）It is control column（It repaiies
Adorn non-OTA aptamers）Identification to ochratoxin A；
Fig. 2 aptamer affinity columns（Modify OTA aptamers）To the specific recognition of ochratoxin A, peak 1 is Aspergillus ochraceus
Toxin A.
Specific embodiment
In order to which content of the present invention is made to easily facilitate understanding, With reference to embodiment to of the present invention
Technical solution is described further, but the present invention is not limited only to this.
Embodiment 1
A kind of POSS of aptamer functionalization is crosslinked the preparation method of organic-silica gel hybridization integral post, concretely comprises the following steps：
（1）Mercapto-modified aptamer first with the rate of 8000r/min is centrifuged 5 minutes, water is then added in and is diluted to
1000 μm of ol/L are heated 3 minutes in 90 DEG C, and aptamer stock solution 1 is formed after being cooled to room temperature；
（2）It is 12.5 in mass ratio：3.75：83.75 ratio, precise 2- acrylamide-2-methyl propane sulfonics monomer,
Methacrylate connects the polyhedral oligomeric silsesquioxane of branch, ethylene glycol dimethacrylate is added in centrifuge tube, accurate
The dosage for really adding in initiator accounts for monomer and the 1.0wt% of crosslinking agent total amount, then accounts for pore-foaming agent for PEG 10000 in proportion
It is respectively 0.5% that pore-foaming agent, which forms the 4.3% of total amount, water and accounts for pore-foaming agent composition total amount,（Column 1）、2.5%（Column 2）、5.0%（Column 3）、
5.5%（Column 4）, correspond to n,N-Dimethylformamide and account for the 95.2% of pore-foaming agent（Column 1）、93.2%（Column 2）、90.7%（Column 3）,
90.2%（Column 4）, sequentially add into 2.0 mL centrifuge tubes, it is molten to add in the aptamer that volume is 2.4 μ L after mixing
Liquid 1,20 min of vortex oscillation, ultrasound degassing 20min form it into uniform solution 2 at room temperature；
（3）Obtained solution 2 is injected at room temperature and is pre-processed using 3- (methacryloxypropyl) propyl trimethoxy silicane
Quartz capillary column in, both ends sealing after immerse 55 DEG C of water-bath successive reaction 12h；The integral post that will be prepared after the completion of reaction
It takes out, liquid chromatography solvents high-pressure pump is connected to, using methanol aqueous solution（v:v=1:1）Cleaning is until pressure stability；
（4）Buffer solution is passed through step（3）In obtained integral post, preserved at a temperature of 4 DEG C.Buffer solution by pH for 8.5,
10 mmol/L Tris-HCl, 120 mmol/L NaCl, 5 mmol/L KCl and 20mmol/L CaCl2Composition.
Embodiment 2
Using blank column, control column and aptamer affinity column（Exemplified by column 3）, affine column length 10cm, respectively according to the following steps
Implement：（1）Balance：First with combination buffer balance 0.5 it is small when, chromatographic condition be flow velocity 0.10 mL/min, pressure 250psi,
The combination buffer is 10mmol/L Tris-HCl, 120 mmol/L NaCl, 5 mmol/L KCl and 20mmol/L
CaCl2, pH 8.50；（2）Enrichment：20 μ L, 10 ng/mL ochratoxin A solution is injected separately into, in whole on-column enrichment
1 it is small when, chromatographic condition be 0.02 mL/min, pressure 250psi；（3）Cleaning：Enriching column is attached on liquid chromatography pump, with knot
Buffer solution is closed to be respectively washed blank column, control column and the affine integral post of aptamer；Cleaning condition is 0.1 mL/ of flow velocity
It is to be checked to collect last cleaning solution by min, pressure 500psi；（4）Elution：Use 30%ACN：70%TE buffer solutions（10mM Tris-
HCl pH8.5,2.5mM EDTA）OTA is eluted from integral post as eluent, 250psi backpressure valves, flow velocity
Eluent when 0.05mL/min collections 0.5 are small is to be checked.Using detecting collection liquid on HPLC- fluorescence detectors, blank column and right
Ochratoxin A is had no according to column and is effectively retained（A in Fig. 1, b）.
Using the affine integral post of aptamer, using 30%ACN：70%TE buffer solutions（10mM Tris-HCl pH8.5,
2.5mM EDTA）As eluent, OTA is effectively eluted（Fig. 2）, eluting peak is in Fig. 1：1. ochratoxin A
（OTA）.
The foregoing is merely presently preferred embodiments of the present invention, all equivalent changes done according to scope of the present invention patent with
Modification should all belong to the covering scope of the present invention.
Sequence table
<110>University of Fuzhou
<120>A kind of POSS of aptamer functionalization is crosslinked organic-silica gel hybridization integral post and preparation method thereof
<130> 1
<160> 1
<170> SIPOSequenceListing 1.0
<210> 1
<211> 39
<212> DNA
<213>Artificial sequence (analysis sequence)
<400> 1
shcgatcggg tgtgggtggc gtaaagggag catcggaca 39
Claims (7)
1. a kind of POSS of aptamer functionalization is crosslinked organic-silica gel hybridization integral post, it is characterised in that：The entirety
Column is to fit high hydrophilic organic polymerized monomer, polyhedral oligomeric sesquialter multi-polysiloxane crosslinking agent, acrylate cross linked dose and nucleic acid
Ligand aqueous solution and initiator dissolve to form homogeneous solution by ternary pore-foaming agent, inject in column and free radical synchronously occurs
Thermal-initiated polymerization and " sulfydryl-alkene " click chemistry react and directly prepare the affine integral post of formation.
2. the POSS of aptamer functionalization according to claim 1 is crosslinked organic-silica gel hybridization integral post, feature
It is：The composition of ternary pore-foaming agent is as mass fraction：N,N-Dimethylformamide 90.2%-95.2%, PEG-10000
The sum of 4.3%, water 0.5%-5.5%, the above components mass fraction are 100%.
3. a kind of POSS of aptamer functionalization according to claim 1 is crosslinked organic-silica gel hybridization integral post,
It is characterized in that：The high hydrophilic organic monomer is 2- acrylamide-2-methyl propane sulfonic monomers；The polyhedral oligomeric sesquialter
Multi-polysiloxane crosslinking agent connects the polyhedral oligomeric silsesquioxane of branch for methacrylate；Described acrylate cross linked dose
For ethylene glycol dimethacrylate；The initiator is azo-bis-isobutyl cyanide；The aptamer is anti-Aspergillus ochraceus
The aptamer of toxin A.
4. a kind of POSS of aptamer functionalization according to claim 1 is crosslinked organic-silica gel hybridization integral post,
It is characterized in that：High hydrophilic organic polymerized monomer, polyhedral oligomeric sesquialter multi-polysiloxane crosslinking agent, acrylate cross linked dose of quality
Than for 12.5:3.75:83.75；The dosage of initiator accounts for monomer and the 1.0wt% of crosslinking agent total amount；Mercapto-modified nucleic acid adaptation
The mole of body is 2.4nmol.
5. a kind of POSS of aptamer functionalization according to claim 3 is crosslinked organic-silica gel hybridization integral post,
It is characterized in that：The aptamer base sequence of the anti-ochratoxin A is 5'-SH-C6-GAT CGG GTG TGG
GTG GCG TAA AGG GAG CAT CGG ACA。
6. it is a kind of prepare as claim 3-5 any one of them aptamer functionalization POSS be crosslinked organic-silica gel it is miscellaneous
Change the method for integral post, which is characterized in that comprise the following steps：
（1）Mercapto-modified aptamer first with the rate of 8000r/min is centrifuged 5 minutes, water is then added in and is diluted to
1000 μm of ol/L are heated 3 minutes in 90 DEG C, and aptamer stock solution 1 is formed after being cooled to room temperature；
（2）2- acrylamide-2-methyl propane sulfonics monomer, methacrylate are first connect to the polyhedral oligomeric silsesquioxane of branch
Alkane, ethylene glycol dimethacrylate and azodiisobutyronitrile are added in centrifuge tube, then by ternary pore-foaming agent add in from
In heart pipe, the aptamer stock solution 1 that volume is 2.4 μ L is added in after mixing, at room temperature 20 min of vortex oscillation,
Ultrasound degassing 20min, forms it into uniform solution 2；
（3）Obtained solution 2 is injected at room temperature and is pre-processed using 3- (methacryloxypropyl) propyl trimethoxy silicane
Quartz capillary column in, both ends sealing after immerse 55 DEG C of water-bath successive reaction 12h；The integral post that will be prepared after the completion of reaction
It takes out, liquid chromatography solvents high-pressure pump is connected to, using methanol aqueous solution（v:v=1:1）Cleaning is until pressure stability；
（4）Buffer solution is passed through step（3）In obtained integral post, preserved at a temperature of 4 DEG C.
7. the POSS according to claim 6 for preparing aptamer functionalization is crosslinked organic-silica gel hybridization integral post
Method, it is characterised in that：Step（4）Described in buffer solution by pH be 8.5,10 mmol/L Tris-HCl, 120 mmol/L
NaCl, 5 mmol/L KCl and 20mmol/L CaCl2Composition.
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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 |
| CN110102270A (en) * | 2019-06-03 | 2019-08-09 | 福州大学 | A kind of affine integral post of aptamer of specific recognition F2 toxin and preparation method thereof |
| CN110115992A (en) * | 2019-06-06 | 2019-08-13 | 福州大学 | A kind of aptamer functional poly zygostyle and preparation method thereof for mycotoxin specific recognition |
| 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 |
| CN111135805A (en) * | 2020-01-21 | 2020-05-12 | 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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| 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 |
| CN110102270A (en) * | 2019-06-03 | 2019-08-09 | 福州大学 | A kind of affine integral post of aptamer of specific recognition F2 toxin and preparation method thereof |
| CN110115992A (en) * | 2019-06-06 | 2019-08-13 | 福州大学 | A kind of aptamer functional poly zygostyle and preparation method thereof for mycotoxin specific recognition |
| CN110115992B (en) * | 2019-06-06 | 2021-06-01 | 福州大学 | Aptamer functionalized polymer column for specific recognition of mycotoxin and preparation method thereof |
| 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 |
| CN111135805A (en) * | 2020-01-21 | 2020-05-12 | 福州大学 | Aptamer functional extraction material for adsorbing phthalate, and preparation method and application 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 |
| CN113406154A (en) * | 2021-06-17 | 2021-09-17 | 哈尔滨工业大学 | Three-dimensional hydrogel-graphene-based biosensor and preparation method thereof |
| CN113406172A (en) * | 2021-06-17 | 2021-09-17 | 哈尔滨工业大学 | Device for detecting myocardial infarction protein marker |
| US11619602B2 (en) | 2021-06-17 | 2023-04-04 | Harbin Institute Of Technology | Three-dimensional hydrogel-graphene-based biosensor and preparation method thereof |
| CN113773453A (en) * | 2021-09-22 | 2021-12-10 | 北方民族大学 | Hydrophilic chromatographic stationary phase for grafting copolymer brush on POSS silica gel, and preparation method and application thereof |
| CN115504559A (en) * | 2022-10-31 | 2022-12-23 | 广东天祺环保科技有限公司 | Preparation method of all-organic composite sewage flocculant microspheres |
| 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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