CN105727894B - Aptamer modified magnetic oxygenated graphene composite material and its preparation and application - Google Patents
Aptamer modified magnetic oxygenated graphene composite material and its preparation and application Download PDFInfo
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- CN105727894B CN105727894B CN201410749218.7A CN201410749218A CN105727894B CN 105727894 B CN105727894 B CN 105727894B CN 201410749218 A CN201410749218 A CN 201410749218A CN 105727894 B CN105727894 B CN 105727894B
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Abstract
The present invention relates to a kind of aptamer modified magnetic oxygenated graphene composite material.The magnetic oxygenated graphene composite material of described immobilized aptamer is to carry out ring-opening reaction by the epoxide group on amido modified nitrilotriacetic acid and graphene oxide to be made.Amido modified nitrilotriacetic acid is used in the preparation of magnetic oxygenated graphene nano metal/composite material by this method, can significantly improve the supported quantity of aptamer.The invention has preferable application prospect and practical value in terms of the affine separation based on aptamer with enrichment target protein.
Description
Technical field
It is specifically a kind of aptamer modified the present invention relates to the affine enrichment of selectivity that aptamer is used for albumen
Magnetic oxygenated graphene composite material preparation and its affine enrichment of efficient high selectivity for target protein.
Background technology
Aptamer (Aptamer, also known as aptamers, aptamer) is energy high-affinity, combines target with high specificity
Single stranded oligonucleotide (ssDNA or ssRNA), generally pass through part index concentration phyletic evolution technology (Systematic
Evolution of Ligands by EXponential enrichment, SELEX) screening acquisition.Aptamer is by model
De Huali, hydrogen bond, pi-pi accumulation, hydrophobic effect equimolecular intermolecular forces form special three-dimensional structure, so as to specifically identify target
Mark.Screening, which obtains aptamer, to be had good compatibility, selectively high, property stabilization, is easy to many advantages, such as chemical modification, at present
The aptamer target reported includes metal ion, small molecule, polypeptide, protein, cell, and application field is wide.
Graphene oxide is due to its excellent physico-chemical property, in field of bioanalysis by more and more extensive concern.Oxygen
Graphite alkene is not only big with specific surface area, while a large amount of oxy radicals, such as hydroxyl, epoxy and carboxyl are also contained in surface, easily
In chemical modification and hydrophilic modifying.These advantages cause graphene oxide to turn into the ideal carrier of metal and metal oxide
(Journal of Chromatography A,2012,1254,8-13;Nanoscale 2014,6,5616-5619), and extensively
It is general to be applied to field of bioanalysis.
The content of the invention
Aptamer is single-stranded oligonucleotides (ssDNA or ssRNA), special three-dimensional structure can be formed, to target
Mark has high selectivity and high specific, and chemical stability is high, is easy to chemical modification.Using aptamer as affinity ligand
It is immobilized in magnetic oxygenated graphene composite material, non-specific adsorption can be reduced, improves the selectivity of enrichment.The mesh of the present invention
Be content by improving surface of graphene oxide carboxyl, there is provided more aptamer binding sites, it is non-so as to prepare
The magnetic oxygenated graphene composite material that specific adsorption is small, bioaccumulation efficiency is high, easily operated, the high selectivity for protein
It is enriched with high specific.
To achieve the above object, the technical solution adopted by the present invention is:
Using amido modified nitrilotriacetic acid (NH2- NTA) with graphene oxide on epoxide group carry out ring-opening reaction,
The content of carboxyl is improved, so as to provide more reaction sites for follow-up modification.After activated carboxyl, with amido modified magnetic ball
Reacted, obtain magnetic oxygenated graphene (GO/NH2-NTA/Fe3O4).Again using magnetic oxygenated graphene as carrier, poly- second
Alkene imines (PEI) is used as reducing agent and stabilizer, is generated in its surface in situ and fixes nanogold particle, further in nanogold
The aptamer of particle surface covalent bond sulfydryl modification.
The preparation of the aptamer modified magnetic oxygenated graphene composite material, is comprised the following steps that:
(1) preparation of magnetic oxygenated graphene:By GO aqueous solution ultrasound 3h, GO is set thoroughly to peel off to form homogeneous solution.
Then NH is added2- NTA and highly basic, make NH2- NTA and carry out epoxy ring opening reaction under basic conditions with GO, centrifugation removes not anti-
The NH answered2-NTA.Add morphine ethyl sulfonic acid, regulation pH 5-6.Then 1- ethyls -3- (3- dimethyl aminopropyls)-carbonization is added
Diimine (EDC) and n-hydroxysuccinimide (NHS) are used as activating reagent, ultrasonic activation carboxyl 1-3h, and priming reaction is completed
Amino ferroso-ferric oxide is added afterwards, ultrasonic reaction 1-2h, prepares magnetic oxygenated graphene (GO/NH2-NTA/Fe3O4);
Wherein, count in mass ratio, NH2- NTA and GO rate of charge is 5:1-1:5;NH2- NTA and highly basic rate of charge 1:1-
1:5;GO and EDC rate of charge is 1:10-1:20;EDC and NHS rate of charge is 1.5:1-1:1;GO and Fe3O4Rate of charge be
1:1-1:5。
(2) magnetic oxygenated graphene composite material is prepared:PEI is added in magnetropism graphene oxide, acutely shakes 1-
10h.Magnetic absorption, after removing unreacted PEI, it is dispersed in water again, adds gold chloride, is well mixed, at 60-95 DEG C
1-4h is reacted in water-bath.Magnetic absorption, it is washed with deionized water three times, magnetic oxygenated graphene composite material is made;
Wherein, count in mass ratio, the rate of charge of magnetic oxygenated graphene and PEI is 1:10-1:40;Magnetic oxygenated graphene
Rate of charge with gold chloride is 25:1-2:1.
(3) preparation of the magnetic oxygenated graphene composite material of immobilized aptamer:Answered to the magnetic oxygenated graphenes of 0.1mg
The pH=7.2-8.0 of aptamers of the 0.1-0.5mL containing sulfydryl modification Tris-HCl cushioning liquid, room temperature are added in condensation material
Lower reaction 1-48h.
The aptamer of sulfydryl modification is dissolved in pH=7.2-8.0 Tris-HCl buffer solutions, the nucleic acid of sulfydryl modification
Fit molar concentration is 1-500 μM;Connected between mercapto groups and aptamer by spacerarm (2-18 methylene).
The magnetic oxygenated graphene composite material of the immobilized aptamer prepared can convenient, on-line preconcentration mesh with high selectivity
Mark albumen.
The invention has the advantages that:
1. the present invention, to the affine enrichment of target, has high selectivity and high specific using aptamer;
2. the present invention improves the content of surface of graphene oxide carboxyl using amido modified nitrilotriacetic acid, finally significantly carry
The supported quantity of high aptamer;
3. the present invention, can not only be a large amount of using immobilized matrix of the magnetic oxygenated graphene composite material as aptamer
Immobilized aptamer, and it is easy to operation;
4. the present invention carries out hydrophilic modifying to magnetic oxygenated graphene using polyethyleneimine, and former as nanogold particle
Position generation and immobilized reducing agent and stabilizer.
Brief description of the drawings
Fig. 1 is the preparation flow figure of aptamer modified magnetic oxygenated graphene composite material.
Fig. 2 is transmission electron microscope picture, and figure A is magnetic oxygenated graphene, and figure B is magnetic oxygenated graphene composite material.
Fig. 3 is the aptamer modified magnetic oxygenated graphene composite material of histone to poly- the third of histone concentration effect
Acrylamide gel electrophoresis analysis figure.
Embodiment
Method provided by the invention is described in detail below by embodiment, but the invention is not limited in any way.
Embodiment 1
1. the preparation of the aptamer modified magnetic oxygenated graphene composite material of histone
As shown in figure 1, prepared by following flow:
1) preparation of magnetic oxygenated graphene:By 2.0mg GO aqueous solution ultrasound 3h, GO is set thoroughly to peel off to be formed uniformly
Solution.Then 6mg NH are added2- NTA and 12mg KOH, makes NH2- NTA and that epoxy addition is carried out under basic conditions with GO is anti-
Should, centrifugation removes unreacted NH2-NTA.Add morphine ethyl sulfonic acid, regulation pH 5-6.Then 32mg 1- ethyls -3- is added
(3- dimethyl aminopropyls)-carbodiimides (EDC) and 23mg n-hydroxysuccinimides (NHS) are used as activating reagent, ultrasound
Activated carboxyl 3h, 4mg amino ferroso-ferric oxides are added after the completion of priming reaction, ultrasonic reaction 2h, prepare magnetic oxygenated graphene
(GO/NH2-NTA/Fe3O4);
2) magnetic oxygenated graphene composite material is prepared:40mg PEI (Mn are added into the magnetic oxygenated graphenes of 1mg
10000) 1h, is acutely shaken.Magnetic absorption, after removing unreacted PEI, it is dispersed in water again, adds 0.4mg gold chlorides,
It is well mixed, react 1h in 60 DEG C of water-bath.Magnetic absorption, it is washed with deionized water three times, magnetic oxygenated graphene is made and answers
Condensation material;
3) preparation of the magnetic oxygenated graphene composite material of immobilized aptamer:Answered to the magnetic oxygenated graphenes of 0.1mg
Histone aptamers (be purchased from precious bioengineering (Dalian) Co., Ltd) of the 0.5mL containing 1 sulfydryl modification is added in condensation material
PH=7.4 Tris-HCl cushioning liquid, react 24h at room temperature.By spacerarm (6 between mercapto groups and aptamer
Methylene) connection.
2. the transmission electron microscope picture of magnetic oxygenated graphene composite material prepared by is as shown in Figure 2;
3. detection (as shown in table 1) of the prepared magnetic oxygenated graphene composite material to aptamer supported quantity
Table 1 is supported quantity of the aptamer on magnetic oxygenated graphene composite material.
GO/NH2-NTA/Fe3O4/PEI/Au | |
Supported quantity nmol/mg | 33.06 |
Relative standard deviation (RSD) % | 7.38 |
Sample size n | 3 |
Embodiment 2
As shown in figure 1, the aptamer modified magnetic oxygenated graphene composite material of histone is prepared by following flow:
1) preparation of magnetic oxygenated graphene:By 2.0mg GO aqueous solution ultrasound 3h, GO is set thoroughly to peel off to be formed uniformly
Solution.Then 1mg NH are added2- NTA and 5mg KOH, makes NH2- NTA and epoxy ring opening reaction is carried out under basic conditions with GO,
Centrifugation removes unreacted NH2-NTA.Add morphine ethyl sulfonic acid, regulation pH 5-6.Then 20mg 1- ethyls -3- (3- bis- are added
Methyl aminopropyl)-carbodiimides (EDC) and 15mg n-hydroxysuccinimides (NHS) be used as activating reagent, ultrasonic activation
Carboxyl 1h, 2mg amino ferroso-ferric oxides are added after the completion of priming reaction, ultrasonic reaction 1h, prepare magnetic oxygenated graphene (GO/
NH2-NTA/Fe3O4);
2) magnetic oxygenated graphene composite material is prepared:10mg PEI (Mn are added into the magnetic oxygenated graphenes of 1mg
10000) 5h, is acutely shaken.Magnetic absorption, after removing unreacted PEI, it is dispersed in water again, adds 0.2mg gold chlorides,
It is well mixed, react 3h in 80 DEG C of water-bath.Magnetic absorption, it is washed with deionized water three times, magnetic oxygenated graphene is made and answers
Condensation material;
3) preparation of the magnetic oxygenated graphene composite material of immobilized aptamer:Answered to the magnetic oxygenated graphenes of 0.1mg
The pH of histone aptamers (be purchased from precious bioengineering (Dalian) Co., Ltd) of the 0.2mL containing sulfydryl modification is added in condensation material
=7.4 Tris-HCl cushioning liquid, reacts 1h at room temperature.By spacerarm (18 methylenes between mercapto groups and aptamer
Base) connection.
Embodiment 3
The aptamer modified magnetic oxygenated graphene composite material of histone is investigated (to implement to the selectivity of histone
The magnetic oxygenated graphene composite material that the histone of the preparation of example 1 is aptamer modified is enrichment material), specific determination step
For:
1) nucleoprotein extracts:Respectively take 1 × 106Individual Hela cells are each to add 0.2mL Lysis in 2 centrifuge tubes
Buffer, quickly being blown and beaten with syringe makes clasmatosis, and then 10000g centrifuges 10min (4 DEG C), removes supernatant.It is each to add 0.1mL
Extract Nuclear Protein Buffer, 4 DEG C of isothermal vibration 1h (1400rpm), then 16000g centrifuge 10min (4
DEG C), take supernatant to produce nucleoprotein solution in new centrifuge tube.
2) the aptamer modified magnetic oxygenated graphene composite material enrichment histone of histone:Take 50 μ g histone cores
The aptamer modified magnetic oxygenated graphene composite material (material) of acid, adds in a tube nucleus protein solution, shakes at room temperature respectively
Reaction 20s is swung, then magnetic adsorptive material and removes supernatant.Remaining tube nucleus protein solution is then precipitated with TCA, obtains adding material
Whole nucleoprotein (nucleoprotein) before material enrichment.
3) above-mentioned sample is subjected to SDS-PAGE analyses:It is aptamer modified to add 10 μ L sample-loading buffer dispersed proteins
Magnetic oxygenated graphene composite material (material);Whole nucleoprotein (the cores added after the molten TCA precipitations of 10 μ L sample-loading buffers weight
Albumen).10 μ L histones standard samples (standard items) are respectively taken again in addition.The SDS-PAGE of equal volume is added into all samples
Loading buffer, after boiling 5min in boiling water, it is added in gel duct.Using 4% concentration glue and 16% separation
Glue, separated under 120V constant-pressure conditions.As a result as shown in figure 3, H2A, H2B, H3, H4 can be clearly visible in " material " swimming lane
Band, this aptamer modified magnetic oxygenated graphene composite material of explanation histone can be enriched with histone well.
Claims (8)
1. the preparation method of aptamer modified magnetic oxygenated graphene composite material, it is characterised in that:Using sulfydryl modification
The nanogold particle of aptamer and covalent modification on magnetic oxygenated graphene composite material be combined, form immobilized nucleic acid
Fit magnetic oxygenated graphene composite material;
Its specific preparation process is as follows:
Utilize the graphene oxide GO containing epoxide group and amido modified nitrilotriacetic acid NH2- NTA carries out epoxy ring opening reaction,
Improve the content of carboxyl on graphene oxide;
Then by covalent reaction between carboxyl and amino ferroso-ferric oxide, magnetic oxygenated graphene GO/NH is prepared2-NTA/
Fe3O4;
Again using magnetic oxygenated graphene as carrier, polyethyleneimine PEI gives birth to as reducing agent and stabilizer in its surface in situ
Into with fixed nanogold particle, magnetic oxygenated graphene composite material is made;
The aptamer containing sulfydryl modification of 1-10 mass parts is added into the magnetic oxygenated graphene composite material of 1 mass parts
PH=7.2-8.0 Tris-HCl cushioning liquid, reacts 1-48h at room temperature;
Wherein, the aptamer of sulfydryl modification is dissolved in pH=7.2-8.0 Tris-HCl buffer solutions, the nucleic acid of sulfydryl modification
Fit molar concentration is 1-500 μM;Connected between mercapto groups and aptamer by 2-18 methylene spacerarm.
2. according to the preparation method described in claim 1, it is characterised in that:The preparation of the magnetic oxygenated graphene composite material
Process is:PEI is added in magnetropism graphene oxide, 1-10h is acutely shaken, magnetic absorption, removes unreacted PEI;Then
Product is dispersed in water again, and adds gold chloride, is well mixed, reacts 1-4h in 60-95 DEG C of water-bath;Magnetic is inhaled
It is attached, it is washed with deionized water three times, magnetic oxygenated graphene composite material is made.
3. according to the preparation method described in claim 2, it is characterised in that:Count in mass ratio, magnetic oxygenated graphene and PEI
Rate of charge is 1:10-1:40;The rate of charge of magnetic oxygenated graphene and gold chloride is 25:1-2:1.
4. according to the preparation method described in claim 1, it is characterised in that:The preparation process of described magnetic oxygenated graphene
For:By GO aqueous solution ultrasound 1-10h, GO is set thoroughly to peel off to form homogeneous solution;Then NH is added2- NTA and highly basic, make NH2-
NTA and GO carries out epoxy ring opening reaction under basic conditions, and centrifugation removes unreacted NH2-NTA;Morphine ethyl sulfonic acid is added, is adjusted
PH is saved between 3-6;Then 1- ethyls -3- (3- dimethyl aminopropyls)-carbodiimides EDC and N- hydroxysuccinimidyl acyl is added
Imines NHS is as activating reagent, ultrasonic activation carboxyl, and amino ferroso-ferric oxide, ultrasonic reaction are added after the completion of priming reaction
1-2h, prepare magnetic oxygenated graphene.
5. according to the preparation method described in claim 4, it is characterised in that:According to mass ratio meter, NH2- NTA and GO rate of charge
For 5:1-1:5; NH2- NTA and highly basic rate of charge 1:1-1:5;GO and EDC rate of charge is 1:10-1:20;EDC and NHS
Rate of charge be 1.5-1:1;The rate of charge of GO and amino ferroso-ferric oxide is 1:1-1:5.
6. according to the preparation method described in claim 4, it is characterised in that:The highly basic is NaOH, KOH, RbOH, CsOH, Sr
(OH)2Or Ba (OH)2In one or two or more kinds.
7. according to the preparation method described in claim 1, it is characterised in that:The aptamer is fitted for the nucleic acid of sulfydryl modification
Body, the sulfydryl amount modified thereon are 1-3.
8. the aptamer modified magnetic oxygenated graphene composite wood that the preparation method described in a kind of claim 1 is prepared
Expect be used for efficiently, be enriched with target protein with high selectivity.
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CN108084528A (en) * | 2016-11-23 | 2018-05-29 | 航天特种材料及工艺技术研究所 | A kind of rubber material and preparation method |
CN106636405B (en) * | 2016-12-26 | 2021-01-05 | 中国科学院长春光学精密机械与物理研究所 | Compound for nucleic acid detection, preparation method thereof and nucleic acid detection method |
CN109387500B (en) * | 2018-09-29 | 2021-01-12 | 南京农业大学 | Method for detecting escherichia coli based on magnetic graphene oxide composite star @ gold-silver alloy nanoparticles |
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CN111470500B (en) * | 2019-01-23 | 2021-10-08 | 清华大学 | Bioactive ligand functionalized graphene film and preparation method thereof |
CN112844308B (en) * | 2019-11-28 | 2022-05-06 | 中国科学院大连化学物理研究所 | Magnetic composite material modified by aptamer and preparation and application thereof |
CN113384534A (en) * | 2021-06-17 | 2021-09-14 | 曲阜师范大学 | Graphene oxide-based composite nano drug delivery system and preparation method thereof |
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