CN110514713A - A kind of aptamers biosensor preparation method and application based on ferrocene as electron donor - Google Patents
A kind of aptamers biosensor preparation method and application based on ferrocene as electron donor Download PDFInfo
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- CN110514713A CN110514713A CN201811239957.6A CN201811239957A CN110514713A CN 110514713 A CN110514713 A CN 110514713A CN 201811239957 A CN201811239957 A CN 201811239957A CN 110514713 A CN110514713 A CN 110514713A
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N27/00—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means
- G01N27/26—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating electrochemical variables; by using electrolysis or electrophoresis
- G01N27/28—Electrolytic cell components
- G01N27/30—Electrodes, e.g. test electrodes; Half-cells
- G01N27/327—Biochemical electrodes, e.g. electrical or mechanical details for in vitro measurements
- G01N27/3275—Sensing specific biomolecules, e.g. nucleic acid strands, based on an electrode surface reaction
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N27/00—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means
- G01N27/26—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating electrochemical variables; by using electrolysis or electrophoresis
- G01N27/28—Electrolytic cell components
- G01N27/30—Electrodes, e.g. test electrodes; Half-cells
- G01N27/327—Biochemical electrodes, e.g. electrical or mechanical details for in vitro measurements
- G01N27/3275—Sensing specific biomolecules, e.g. nucleic acid strands, based on an electrode surface reaction
- G01N27/3277—Sensing specific biomolecules, e.g. nucleic acid strands, based on an electrode surface reaction being a redox reaction, e.g. detection by cyclic voltammetry
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N27/00—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means
- G01N27/26—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating electrochemical variables; by using electrolysis or electrophoresis
- G01N27/416—Systems
- G01N27/48—Systems using polarography, i.e. measuring changes in current under a slowly-varying voltage
Abstract
A kind of aptamers biosensor preparation method and application based on ferrocene as electron donor, steps are as follows: chitosan solution being added in the graphene oxide solution of activated carboxyl, then modifies the mixed solution on screen printing carbon electrode surface；Aptamers end adds particular bases and synthesizes hairpin structure to design, and modifies amino and ferrocene respectively at both ends, and the aptamers chain is effectively fixed in graphene oxide-chitosan/screen printing carbon electrode surface by the formation of amido bond；Aptamers and the specific recognition of object induce aptamers conformational change, change so as to cause the current signal that ferrocene generates in phosphate buffer solution, and then be monitored to object.The present invention is able to achieve the super sensitivity detection of Profenofos, thimet, four kinds of isocarbophos, omethoate organophosphorus pesticides, and detection time is short, and detection limit is low, provides a kind of new technology for the detection of organophosphorus pesticide and other field harmful substance.
Description
Technical field
The present invention relates to a kind of aptamers biosensor preparation method and application based on ferrocene as electron donor,
Belong to electrochemica biological sensor detection technique field.
Background technique
Organophosphorus pesticide is a kind of organic phosphorus compound, because its efficiently, low toxicity, low-residual the advantages of, agriculturally by
It is widely used in prevention and treatment pest and disease damage and weeds.The use of these pesticides can help prevent crop loss.But it is remained on agricultural product
Excessive organophosphorus pesticide can enter human body by food chain, nerve dysfunction is caused in conjunction with acetylcholinesterase, is led
It causes paralysis even dead, high risks is caused to human health.Profenofos, thimet, isocarbophos and omethoate are extensive
The organophosphorus pesticide used, its exceeded event frequent occurrence in victual.Therefore, constructing a kind of quick, sensitive, safety can
The Detecting Pesticide analysis method leaned on is very necessary.
In the past few decades, various effective organophosphorus pesticide detection methods are had been set up, for example, gas phase
Chromatography, high performance liquid chromatography, enzyme linked immunosorbent assay, colorimetric method, fluorescence method etc..But their most time and effort consumings, instrument
Equipment is expensive, and operator's technical requirements are high, is not suitable for live quickly analysis.In order to improve these problems, electrochemistry adaptation
Body sensor due to its it is good selectivity, high sensitivity and it is cheap the advantages that and be used widely.In electrochemistry
In the application process of aptamer sensor, the generation and amplification of electrochemical signals are the key that restrict the performances such as transducer sensitivity
Factor.
Graphene oxide is well-known excellent electrical-conductive nanometer material, and the combination of it and chitosan solution is in amplification electrification
Good biocompatibility and stability also are provided for biological identification molecule while learning signal.Ferrocene is a kind of organic transitional
Metallic compound is widely used as electrochemistry letter due to its excellent reversible redox performance and good chemical stability
Number probe.In recent years, having document report, it can provide electronics in phosphate buffer, and resulting electrochemical signals have
Super high sensitivity.Therefore, using above-mentioned material it is expected to develop a kind of overdelicate electrochemical aptamer sensor and for organic
Phosphorus Pesticides Testing.
Summary of the invention
The purpose of the present invention is to provide a kind of high sensitivity, easy to operate, the good aptamers biosensor of selectivity,
And it is used for the detection of Profenofos, thimet, four kinds of isocarbophos, omethoate organophosphorus pesticides.
The technical solution of the present invention is as follows: having graphene oxide-chitosan laminated film silk-screen printing carbon in surface modification
The hair fastener aptamers of the fixed ferrocene label of electrode surface, constitute aptamers biosensor；Pretreatment, oxidation including electrode
The preparation of graphene-chitosan solution, the design of aptamers hairpin structure and label, organophosphorus pesticide detection, specific steps
Are as follows:
(1) pretreatment of electrode: screen printing carbon electrode working region is completely immersed in 0.5 M sulfuric acid solution ,-
5 circle cyclic voltammetry scans are carried out in 1.0~+1.0 V potential ranges, stablize electrode to obtain performance；
(2) EDC and NHS, room temperature condition graphene oxide-chitosan solution preparation: are added in graphene oxide solution
The lower carboxyl being incubated on active oxidation graphene, chitosan solution is added after eccentric cleaning, prepares 1 mg/mL graphene oxide-
Chitosan solution；
(3) design and label of aptamers hairpin structure: in aptamers (5 '-AGCTTGCTGCAGCGA
TTCTTGATCGCCACAGAGCT-3 ') 3 ' end addition with 5 ' hold before several base-pair (AGCTTG) complementary pairings base-pairs
CAAGCT, and amino (- NH is marked respectively at both ends2) and ferrocene (Fc), newly synthesized aptamers chain (NH2-AGCTTGCTGC
AGCGATTCTTGATCGCCACAGAGC TCAAGCT-Fc) hairpin structure can be effectively formed；
(4) detection of organophosphorus pesticide: the organophosphorus pesticide standard items of various concentration are added dropwise and are passed in the biology prepared
On sensor, it is incubated for certain time at room temperature, combines aptamers sufficiently with pesticide；Target pesticide and aptamers it is special
Property combine open aptamers hairpin structure, cause electron donor ferrocene far from electrode surface, when the phosphate in pH 7.4
When executing the detection of electrochemistry differential pulse voltammetry in buffer solution, the current peak that+0.7V or so occurs will reduce, in turn
Detection target concentration；Selected aptamers are broad spectrum activity aptamers, are had to Profenofos, thimet, isocarbophos, omethoate
Good detectability.
Preparation principle of the invention are as follows: graphene oxide-chitosan nano of screen printing carbon electrode surface modification is compound
Material can not only amplify electrochemical signals, and a large amount of carboxyl can be with the amino knot modified in aptamers on graphene oxide
The fixation for being conducive to aptamers is closed, in addition, the good biocompatibility of the composite material helps to maintain aptamers activity.Design
The hair fastener aptamers of synthesis include two segments: one be specific recognition organophosphorus pesticide aptamers sequence, the other is
The oligonucleotide sequence for being used to form loop-stem structure of autonomous Design addition.In 5 ' and 3 ' end difference of the hair fastener aptamers sequence
It modifies amino and ferrocene and it is chitosan-modified to be fixed on by graphene oxide-by the combination of amino and carboxyl for hair fastener aptamers
Screen printing carbon electrode surface.In the presence of no object, aptamers keep hairpin structure, and ferrocene is tightly attached to
Electrode surface, the current signal protrusion for causing electron donor ferrocene to generate under certain voltage effect display.Work as target
In the presence of molecule, the expansion of aptamers hairpin structure causes electrochemical signals to reduce.With the increase of aimed concn, electric signal is strong
Degree gradually decreases, so as to measure organophosphorus pesticide target concentration.
The invention has the benefit that the present invention provides a kind of aptamers biologies based on ferrocene as electron donor
Transducer production method and application, and it is used for the detection of four kinds of organophosphorus pesticides.Use ferrocene as electric signal probe
Strategy keeps the signal of the sensor very sensitive, in addition, transducer production method is simple, there is higher stability and specificity,
It can be used in the detection of organophosphorus pesticide in vegetable sample.Therefore, the present invention is that the remaining detection of small molecule harmful substance proposes
It is a kind of novel and there are highly sensitive and accuracy analysis detection means.
Detailed description of the invention
The preparation process of Fig. 1 aptamers biosensor.
The electrochemical Characterization of Fig. 2 aptamers biosensor.
The feasibility study of Fig. 3 aptamers biosensor.
Fig. 4 measures DPV response and the respective standard curve of various concentration Profenofos.
Fig. 5 measures DPV response and the respective standard curve of various concentration thimet.
Fig. 6 measures DPV response and the respective standard curve of various concentration isocarbophos.
Fig. 7 measures DPV response and the respective standard curve of various concentration omethoate.
Fig. 8 sensor detects the major parameter of different pesticides.
Fig. 9 actual sample recovery of standard addition.
The specificity analysis of Figure 10 aptamers biosensor.
Specific embodiment
Present invention is further described in detail with reference to the accompanying drawings and examples, it should be pointed out that reality as described below
Example is applied to be intended to convenient for the understanding of the present invention, without limiting its protection scope.
Embodiment 1:
A kind of aptamers biosensor preparation method based on ferrocene as electron donor, preparation method it is specific
Step is:
(1) design and the preparation of its solution of hair fastener aptamers (HP)
Before 3 ' end additions of aptamers (5 '-AGCTTGCTGCAGCGATTCTTGATCGCCACAGAGCT-3 ') are held with 5 '
The base-pair CAAGCT of several base-pair (AGCTTG) complementary pairings, and amino (- NH is marked respectively at both ends2) and ferrocene
(Fc), newly synthesized aptamers chain (NH2- AGCTTGCTGC AGCGATTCTTGATCGCCACAGAGCTCAAGCT-Fc) it uses
DNAman software Fitting Analysis, discovery can be effectively formed hairpin structure.In order to which the aptamers for synthesizing the design form hair fastener
Structure, the aptamers stoste heat 5min in 95 DEG C of water-baths, are then slowly cooled to room temperature.With the Tris-HCl of pH 7.5
2 μM of storage solutions are diluted to for solvent.
(2) preparation of graphene oxide-chitosan (GO-CS) solution
5 mg Chitosan powders are added in the acetic acid solution that 25 mL concentration are 1.0%, being made into concentration is 0.2 wt%'s
Chitosan solution magnetic agitation 8 hours or more, is completely dissolved chitosan.It is added in the graphene oxide solution of 1 mg/mL
0.15 M EDC and 0.1 M NHS is incubated for carboxyl on 30 min active oxidation graphenes under room temperature, is then centrifuged for machine centrifugation
(8000 rpm, 15 min) are afterwards plus water cleans 3 times and removes remaining EDC and NHS, and 1 mL is finally added in obtained sediment
0.2 wt% chitosan solution prepares graphene oxide-chitosan solution of 1 mg/mL.
(3) pretreatment of electrode
The working region screen printing carbon electrode (SPCE) is completely immersed in 0.5 M sulfuric acid solution, in-1.0 -+1.0 V
5 circle cyclic voltammetry scans are carried out in potential range, to obtain stablizing electrochemical signals.It is clean rear spare with ultrapure water.
(4) building of aptamers biosensor
Graphene oxide-chitosan solution of 1 mg/mL of step (2) preparation is diluted to 0.2 mg/mL, 8 μ L should receive
Rice composite solution is added dropwise in the working region SPCE that step (3) has pre-processed, and dries at room temperature；Take 8 μ L, 2 μM of aptamers
Solution is added dropwise on the chitosan-modified electrode of graphene oxide-, and the amino in aptamers can be with the carboxyl shape of graphene oxide
At amido bond, so that aptamers be made to be tightly fixed to electrode surface；Finally, after the sensor of the drying is gently rinsed with ultrapure water
It is spare to be put in 4 DEG C of refrigerators.The preparation process of aptamers biosensor is as shown in Figure 1.
(5) electrochemical Characterization of aptamers biosensor
As shown in Fig. 2, having carried out CV characterization to the assembling process of aptamers biosensor preparation process.With naked screen printing
Brush carbon electrode compares (Fig. 2-a), and the redox peak current of the chitosan-modified electrode of graphene oxide-is higher (Fig. 2-b), this
It is since the compound has stronger electric conductivity.In addition, the increase of DPV peak current and the offset of spike potential also illustrate electrode table
Face is successfully modified.With the further modification of hair fastener aptamers, current peak dramatically increases (Fig. 2-c), this may be due to
The ferrocene marked in hair fastener aptamers generates larger current signal close to electrode surface.When sensor the third bromine of target molecule
After phosphorus (profenofos) is incubated for, peak current is substantially reduced (Fig. 2-d), this may be because of are as follows: aptamers shape in conjunction with object
At object-adaptor complex hinder electronics transfer in potassium ferricyanide solution；Object opens aptamers hairpin structure,
Make ferrocene far from electrode surface.The successful building of the aptamers biosensor of above-mentioned the results show.
(6) feasibility study of aptamers biosensor
Fig. 3 illustrates the feasibility of the aptamers biosensor.DPV is carried out when bare electrode immerses phosphate buffer solution
When measuring (potential range :+0.4~+0.9V) (Fig. 3-a), discovery current curve is almost straight line, without apparent peak
Value.It is chitosan-modified rear (Fig. 3-b) with graphene oxide-, very faint electrochemical signals have been obtained, have shown graphite oxide
Alkene-chitosan helps to amplify electrochemical signals.Further electricity obtained above is modified with the hair fastener aptamers that the present invention designs
There is a very big current peak in pole (Fig. 3-d).However, when by be only marked with amino organic phosphorus aptamers (Apt,
NH2- AGCTTGCTG CAGCGATTCTTGATCGCCACAGAGCT) it is fixed on the chitosan-modified electrode table of graphene oxide-
Face (Fig. 3-c), obtained peak signal is negligible.This shows that the electrochemical signals that the system generates are ferrocene
It is generated under certain potentials.Target pesticide Profenofos, which is added, leads to current reduction (Fig. 3-e), illustrates that object is adapted to hair fastener
Body, which combines, makes ferrocene far from electrode surface, and the super sensitivity detection of object can be achieved according to the difference of electrochemical signals.
Embodiment 2:
A kind of application of the aptamers biosensor based on ferrocene as electron donor:
(1) in water organophosphorus pesticide detection
The different organophosphorus pesticides of 8 μ L various concentrations are added dropwise on aptamers biosensor, are incubated in air
1h.After ultrapure water is gently rinsed and is dried with nitrogen, its DPV electrochemical signals is measured in 7.4 phosphate buffer solution of pH.Knot
Fruit as shown in figs. 4-7 (Fig. 4 Profenofos, Fig. 5 thimet, Fig. 6 isocarbophos, Fig. 7 omethoate), DPV response signal and four
There is good linear relationship between the logarithm of kind organophosphorus pesticide concentration.Their equation of linear regression, the range of linearity, correlation
Coefficient and detection limit are summarized in fig. 8.The extremely low detection line of the sensor shows aptamers biosensor prepared by the present invention
With high sensitivity.
(2) in vegetable sample organophosphorus pesticide detection
In order to further study the practicability of aptamers biosensor, recovery experiment is carried out using standard addition method.Letter
Yan Zhi, the Profenofos mark of sprinkling various concentration (10 nM, 100 nM) in vegetable sample (rape, wild cabbage, spinach, pakchoi)
Quasi- solution, then pre-processes vegetable sample, extracts remaining pesticide.Then, with aptamers biology prepared by the present invention
Sensor carries out Electrochemical Detection to all extracting solutions.Fig. 9 lists experimental result, and the rate of recovery is 79.66%~136.90%
Between, show that the sensor can be used for the detection and analysis of actual sample.
Embodiment 3:
A kind of performance test of the aptamers biosensor based on ferrocene as electron donor:
(1) specificity analysis
Use sevin, malathion, acephatemet, Azodrin and chlopyrifos and their mixture as interference pesticide pair
The selectivity of the aptamer sensor is detected.(a, b, c, d, e, f respectively represent five kinds of interference as shown in Figure 10
Pesticide and their mixture；G, h, i, j, k respectively represent Profenofos, thimet, isocarbophos and omethoate and its
Mixture；L represents this nine kinds of pesticide combinations；All pesticide concentrations are 10 nM), there is (the third bromine without specific targets object
Phosphorus, thimet, isocarbophos and omethoate) when, electrochemical signals are larger, show that aptamers cannot be with these interference pesticides point
Son combines.In addition, histogram k and l is not distinguished significantly, aptamers biosensor prepared by the present invention is demonstrated again
There are specificity and anti-interference ability well.
(2) stability study
In order to study the stability of the aptamers biosensor, the sensor that 10 prepare is stored in 4 DEG C of refrigerators
It is interior, its DPV signal is measured after a period of time and is compared with the DPV signal of freshly prepared sensor.Storage is electric after a week
Chemical signal variation is negligible.After storage 15 days, peak point current remains at 91.35% or so, and relative standard is inclined
Difference is 7.06%.Illustrate that the biosensor is with good stability.
Claims (8)
1. a kind of aptamers biosensor preparation method and application based on ferrocene as electron donor, the sensor are
Screen printing carbon electrode, which is characterized in that have graphene oxide-chitosan laminated film silk-screen printing carbon electric in surface modification
The hair fastener aptamers of the fixed ferrocene label of pole surface, complete the building of aptamer sensor.
2. it is as described in claim 1 it is a kind of based on ferrocene as the aptamers biosensor preparation method of electron donor and
Using, which is characterized in that screen printing carbon electrode working region screen printing carbon electrode pretreatment: is completely immersed in 0.5 M sulphur
In acid solution, cyclic voltammetry scan 5 is carried out in -1.0~+1.0 V potential ranges and is enclosed, to obtain the stable electrode of performance.
3. it is as described in claim 1 it is a kind of based on ferrocene as the aptamers biosensor preparation method of electron donor and
Using, which is characterized in that it is prepared for graphene oxide-chitosan mixed solution: EDC and NHS being added in graphene oxide solution,
Chitosan solution, preparation 1 mg/mL oxidation are added after eccentric cleaning for the carboxyl being incubated on active oxidation graphene under room temperature
Graphene-chitosan solution.
4. it is as described in claim 1 it is a kind of based on ferrocene as the aptamers biosensor preparation method of electron donor and
Using, which is characterized in that the design synthesis of hair fastener aptamers and label: in aptamers (5 '-AGCTTGCTG
CAGCGATTCTTGATCGCCACAGAGCT-3 ') 3 ' end additions held with 5 ' before several base-pair (AGCTTG) complementary pairings
Base-pair CAAGCT, and amino (- NH2) and ferrocene (Fc), newly synthesized aptamers chain (NH2- are marked respectively at both ends
AGCTTGCTGCAGCGATTCTTGATCGC CACAGAGCTCAAGCT-Fc) hairpin structure can be effectively formed.
5. it is as described in claim 1 it is a kind of based on ferrocene as the aptamers biosensor preparation method of electron donor and
Using, which is characterized in that for measuring organophosphorus pesticide: the organophosphorus pesticide standard items of various concentration being added dropwise and are being prepared
On biosensor, it is incubated for certain time at room temperature, combines aptamers sufficiently with pesticide；Then the sensor is set
The detection of electrochemistry differential pulse voltammetry is executed in 7.4 phosphate buffer solution of pH.
6. it is as described in claim 1 it is a kind of based on ferrocene as the aptamers biosensor preparation method of electron donor and
Using, which is characterized in that can be used for four kinds of object analyses: selected aptamers are broad spectrum activity aptamers, are mixed with Profenofos, first
Phosphorus, isocarbophos, omethoate have good specific binding capacity.
7. it is as described in claim 1 it is a kind of based on ferrocene as the aptamers biosensor preparation method of electron donor and
Using, which is characterized in that electrochemical signals derive from ferrocene: under the voltage effect of+0.7 V or so, phosphate-buffered is molten
Ferrocene in liquid can produce electronics, provide electrochemical signals.
8. it is as described in claim 1 it is a kind of based on ferrocene as the aptamers biosensor preparation method of electron donor and
Reflect pesticide concentration using, which is characterized in that difference electrochemical signals caused by aptamers conformation change: target pesticide be adapted to
The hairpin structure of aptamers is opened in the specific binding of body, causes ferrocene far from electrode surface, thus the electrification for generating it
It learns signal to reduce, and then detection target concentration.
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