CN107202822B - The preparation of nano silver/carbon nano tube modified electrode aurantiin molecular engram sensor - Google Patents
The preparation of nano silver/carbon nano tube modified electrode aurantiin molecular engram sensor Download PDFInfo
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Abstract
The invention discloses a kind of preparations of nano silver/carbon nano tube modified electrode aurantiin molecular engram sensor, use nano silver/carbon nano tube modified glass-carbon electrode first, and nano silver/carbon nano tube modified electrode is made；Then in the reactor, it is separately added into, ethyl alcohol: 52 ~ 62%, dipentaerythritol triacrylate: 8 ~ 15%, itaconic acid: 5 ~ 10%, 1- acrylic -3- ethyl imidazol(e) hexafluorophosphate: 10 ~ 18%, azodiisobutyronitrile: 1.0 ~ 3.0%, aurantiin: 4.0 ~ 10%, anaerobic atmosphere, 60 ± 2 DEG C be stirred to react 18 ~ for 24 hours, template molecule is removed to get aurantiin molecularly imprinted polymer using methanol and acetic acid mixed solution；Again by molecularly imprinted polymer drop coating to nano silver/carbon nano tube modified electrode, aurantiin molecular engram sensor is obtained.The sensor has high compatibility and selectivity.With high sensitivity, specificity is good, detection is quick, can Reusability.
Description
Technical field
Applied technical field the present invention relates to a kind of preparation method of molecular engram sensor and quickly is detected, especially
It is related to a kind of preparation method of nano silver/carbon nano tube modified electrode aurantiin molecular engram sensor, for detecting drug, food
Aurantiin in product, biological sample.
Background technique
Aurantiin (alias: naringin, naringin, aurantiin), molecular formula C27H32O14, relative molecular mass is
580.53, white is dissolved in methanol, ethyl alcohol, acetone, acetic acid, dilute alkaline soln and hot water to Light yellow crystals powder, under room temperature,
Solubility in water is 0.1%, up to 10% at 75 DEG C.Insoluble in nonpolar solvents such as petroleum ether, ether, benzene and chloroforms.Shaddock
Skin glycosides is a kind of Flavanones compound.Due to being absolutely not conjugated between A ring and B ring, so there is strong purple in 282nm
Outer absorption peak makes aurantiin show various biological activity and pharmacological action.With anti-inflammatory, antiviral, anticancer, antimutation, resist
Allergy, antiulcer, analgesia, hypotensive activity, energy hypercholesterolemia, the formation for reducing thrombus, improve local microcirculation and nutrition
Supply, can be used for producing prevention and treatment cardiovascular and cerebrovascular disease.Naringin has apparent anti-inflammatory effect, the naringin pair of 200mg/l concentration
Vesicular stomatitis virus has very strong inhibiting effect；It reduces the viscosity of blood, reduce the formation of thrombus, and have analgesia, town
Quiet and stronger increase experimental animal bile secretion；There are desensitization and antiallergy, blood circulation promoting spasmolysis, improve local microcirculation and nutrition
The performance of supply, the toxic side effect of damage, alleviation streptomysin to promotion excretion of drug, releasing streptomysin to the 8th pair of cranial nerve
There is unique curative effect；Naringin is under alkaline condition, oxidation-treated, and dihydrochalcone sweetener can be obtained, and sugariness is sucrose
1000 times.Naringin and isovanillin act on, and obtain neohesperidin, it is one that neohesperidin, which is 950 times of dihydrochalcone sugariness,
Plant the sweetener of new generation of nontoxic, low energy, Gao Tiandu.
Currently, the method for detection aurantiin mainly has high performance liquid chromatography, liquid chromatography-mass spectrography, chromatographic accuracy
It is subject to certain restrictions and instrument is somewhat expensive that professional is needed to operate, also limit its application.In addition, due to aurantiin with
Other flavonoids molecular structures are very close to be difficult to separate, and when measurement interferes with each other, and accurate to detect aurantiin highly difficult.Therefore,
Finding a kind of good selectivity, high sensitivity, the method for the detection aurantiin easy to operate being used for has important use value.
Molecular imprinting technology is one of the main method of high selectivity material that current exploitation has molecular recognition function, it
It is to be polymerize after removing template molecule in molecular engram by forming a highly cross-linked rigid macromolecule around template molecule
The recognition site with binding ability is left in the network structure of object, and one kind of high selection recognition performance is shown to template molecule
Technology.This technology imitates precordainment with its structure and specific recognition has been to be concerned by more and more people, and has been used successfully to solid phase
Extraction or the fields such as micro- Solid Phase Extraction, affinity chromatography or Capillary Electrophoresis and sensor.
According to the molecular engram sensor of this technology preparation, it is applied to Pharmaceutical Analysis, environmental protection and life science
In play a very important role.Functional molecular is modified on electrode in a suitable manner, the selective good, high sensitivity of preparation,
There is the reproducible electrochemical sensor of certain service life to become analysis science worker and makes great efforts the project explored.But it is traditional
Trace film thickness prepared by immunoblot method is difficult to control, and high-crosslinking-degree makes electron transmission speed and low-response, Monitoring lower-cut
Height influences application of the molecular imprinting technology in electrochemical sensor.Therefore, it establishes a kind of sensitive, quick, easy, specific
The detection method that high, reproducible economy uses measures the naringin content accurate quantitative analysis in food, drug, biological sample
It is very necessary.
Summary of the invention
The purpose of the present invention is combining molecular engram with electrochemical sensor, a kind of aurantiin molecular engram is provided
The preparation method of electrochemical sensor, mainly using aurantiin as template, glassy carbon electrode surface by oxide/carbon nanometer tube, receive
The modification of rice silver particles, improves the sensitivity of sensor, prepares aurantiin molecular imprinting electrochemical sensing using drop coating legal system
Device.
Instrument and reagent
CHI660B electrochemical workstation (Shanghai Chen Hua instrument company), experiment use three-electrode system: supplemented by platinum electrode
Electrode is helped, Ag/AgCl is reference electrode (SCE), and glass-carbon electrode (GCE) is working electrode；KQ-250E type ultrasonic cleaner
(Kun Feng ultrasonic instrument Co., Ltd).
Oxide/carbon nanometer tube；Pentaerythritol triacrylate (PETA), itaconic acid；1- acrylic -3- ethyl imidazol(e) hexafluoro
Phosphate, azodiisobutyronitrile, dehydrated alcohol；Aurantiin；Silver nitrate；Gelatin；Phosphate buffer solution；Agents useful for same is analysis
Pure, experimental water is secondary distilled water.
The purpose of the present invention is achieved through the following technical solutions.
A kind of preparation method of nano silver/carbon nano tube modified electrode aurantiin molecular engram sensor, is characterized in that, should
Method has following processing step:
(1) it nano silver/carbon nano tube modified liquid preparation: in the reactor, is added, goes by following composition mass percentage concentration
Ionized water: 78 ~ 84%, silver nitrate: 2.0 ~ 5.0%, oxide/carbon nanometer tube: 3 ~ 8%, ultrasound 20min, is uniformly dispersed at room temperature, then plus
Entering mass percentage concentration is 20% hydrazine hydrate: 10 ~ 15%, the sum of each component content is absolutely, to be stirred to react 20min, is placed
Overnight, nano silver/carbon nano tube modified liquid is obtained；
(2) nano silver/carbon nano tube modified electrode preparation: glass-carbon electrode is successively carried out with 0.2 μm, 0.01 μm of polishing powder
Then surface polishing is cleaned by ultrasonic with secondary distilled water respectively, ethanol washing, drying, and 15 ~ 18 μ L are added dropwise in glassy carbon electrode surface
Nanogold graphene modified liquid, is placed under infrared lamp, to get nano silver/carbon nano tube modified electrode after the dry solvent that volatilizees；
(3) preparation of aurantiin molecularly imprinted polymer: in the reactor, being added by following composition mass percentage concentration,
Ethyl alcohol: 52 ~ 62%, dipentaerythritol triacrylate: 8 ~ 15%, itaconic acid: 5 ~ 10%, 1- acrylic -3- ethyl imidazol(e) hexafluoro phosphorus
Hydrochlorate: 10 ~ 18%, azodiisobutyronitrile: 1.0 ~ 3.0%, aurantiin: 4.0 ~ 10%, the sum of each component content is absolutely, to stir
Mix dissolution, lead to 15 min of inert gas deoxygenation, anaerobic atmosphere, 60 ± 2 DEG C be stirred to react 18 ~ for 24 hours, the product first that will be obtained
Alcohol: acetic acid volume ratio is that 3:1 mixed solution impregnates 12 ~ 15h, removes template molecule, dry to get the polymerization of aurantiin molecular engram
Object；
(4) preparation method of aurantiin molecular imprinting electrochemical sensor: suitable aurantiin molecularly imprinted polymer is taken
It is scattered in 1% gelatin solution, the aurantiin imprinted polymer solution of 20g/L is made；Then by above-mentioned solution 15 ~ 20
μ L is added drop-wise to nano silver/carbon nano tube modified electrode of step (2) preparation, is placed under infrared lamp, to get shaddock after the dry solvent that volatilizees
Skin glycosides molecular imprinting electrochemical sensor.
The mass ratio of the silver nitrate and oxide/carbon nanometer tube is that 1:2 ~ 3 are optimal in step (1).
Dipentaerythritol triacrylate described in step (3): itaconic acid: 1- acrylic -3- ethyl imidazol(e) hexafluoro
Phosphatic mole optimal for 1:1:1.
The inert gas is neon or argon gas in step (3).
The anaerobic atmosphere is that polymerization process is passed through always inert gas in step (3).
Advantages of the present invention and effect are:
The present invention combines engram technology, LBL self-assembly method and drop-coating, in nano silver/carbon nano tube modified glass carbon
Electrode surface successfully has developed a kind of aurantiin trace electrochemical sensor with specific selectivity.By with nano silver/
That the response of carbon nano tube modified molecular engram electrode is compared, aurantiin molecular engram sensor prepared by the present invention
Response greatly improve.The trace sensor shows higher compatibility and selectivity, response current and shaddock ped to aurantiin
The concentration of glycosides is 1.0 × 10-7~2.0×10-4It is in good linear relationship within the scope of mol/L, detection is limited to 2.16 × 10-8mol/
Aurantiin molecular imprinting electrochemical sensor prepared by the present invention is used successfully to drug, food, aurantiin in biological sample by L
In detection, the rate of recovery is between 96.52 ~ 104.12%, therefore aurantiin molecular engram sensor prepared by the present invention can answer extensively
For related fieldss such as chemical industry, biological medicine, food, environmental protection tests.
Specific embodiment
Embodiment 1
(1) it nano silver/carbon nano tube modified liquid preparation: in the reactor, is separately added into, deionized water: 8 mL, nitric acid
Silver: 0.3g, oxide/carbon nanometer tube: 0.6g, ultrasound 20min, is uniformly dispersed at room temperature, 20% hydrazine hydrate: 1.1 mL are stirred to react
20min is stood overnight, and obtains nano silver/carbon nano tube modified liquid；
(2) nano silver/carbon nano tube modified electrode preparation: glass-carbon electrode is successively carried out with 0.2 μm, 0.01 μm of polishing powder
Then surface polishing is cleaned by ultrasonic with secondary distilled water respectively, ethanol washing, drying, and 16 μ L are added dropwise in glassy carbon electrode surface and receive
Rice gold-graphene decorating liquid, is placed under infrared lamp, to get nano silver/carbon nano tube modified electrode after the dry solvent that volatilizees；
(3) it the preparation of aurantiin molecularly imprinted polymer: in the reactor, is separately added into, ethyl alcohol: 72 mL, two Ji Wusi
Alcohol triacrylate: 12g, itaconic acid: 8g, 1- acrylic -3- ethyl imidazol(e) hexafluorophosphate: 14g, azodiisobutyronitrile:
2.0g, aurantiin: 7g, stirring and dissolving lead to 15 min of inert gas deoxygenation, and anaerobic atmosphere, 60 ± 2 DEG C are stirred to react 20h, will
The product methanol arrived: acetic acid volume ratio is that 3:1 mixed solution impregnates 13h, removes template molecule, dry to get aurantiin point
Sub- imprinted polymer；
(4) preparation method of aurantiin molecular imprinting electrochemical sensor: suitable aurantiin molecularly imprinted polymer is taken
It is scattered in 1% gelatin solution, the aurantiin imprinted polymer solution of 20g/L is made；Then by above-mentioned 16 μ L of solution
It is added drop-wise to nano silver/carbon nano tube modified electrode of step (2) preparation, is placed under infrared lamp, to get shaddock ped after the dry solvent that volatilizees
Glycosides molecular imprinting electrochemical sensor.
Embodiment 2
(1) it nano silver/carbon nano tube modified liquid preparation: in the reactor, is separately added into, deionized water: 7.8 mL, nitric acid
Silver: 0.2g, oxide/carbon nanometer tube: 0.5g, ultrasound 20min, is uniformly dispersed at room temperature, 20% hydrazine hydrate: 1.5 mL are stirred to react
20min is stood overnight, and obtains nano silver/carbon nano tube modified liquid；
(2) nano silver/carbon nano tube modified electrode preparation: glass-carbon electrode is successively carried out with 0.2 μm, 0.01 μm of polishing powder
Then surface polishing is cleaned by ultrasonic with secondary distilled water respectively, ethanol washing, drying, and 17 μ L are added dropwise in glassy carbon electrode surface and receive
Rice gold-graphene decorating liquid, is placed under infrared lamp, to get nano silver/carbon nano tube modified electrode after the dry solvent that volatilizees；
(3) it the preparation of aurantiin molecularly imprinted polymer: in the reactor, is separately added into, ethyl alcohol: 6.6mL, two Ji Wusi
Alcohol triacrylate: 1.5g, itaconic acid: 1.0g, 1- acrylic -3- ethyl imidazol(e) hexafluorophosphate: 1.0g, two isobutyl of azo
Nitrile: 0.3g, aurantiin: 1.0g, stirring and dissolving lead to 15 min of inert gas deoxygenation, and anaerobic atmosphere, 60 ± 2 DEG C are stirred to react
18h, the product methanol that will be obtained: acetic acid volume ratio is that 3:1 mixed solution impregnates 12h, removes template molecule, it is dry to get
Aurantiin molecularly imprinted polymer；
(4) preparation method of aurantiin molecular imprinting electrochemical sensor: suitable aurantiin molecularly imprinted polymer is taken
It is scattered in 1% gelatin solution, the aurantiin imprinted polymer solution of 20g/L is made；Then by above-mentioned 17 μ L of solution
It is added drop-wise to nano silver/carbon nano tube modified electrode of step (2) preparation, is placed under infrared lamp, to get shaddock ped after the dry solvent that volatilizees
Glycosides molecular imprinting electrochemical sensor.
Embodiment 3
(1) it nano silver/carbon nano tube modified liquid preparation: in the reactor, is separately added into, deionized water: 8.4mL, nitric acid
Silver: 0.3g, oxide/carbon nanometer tube: 0.3g, ultrasound 20min, is uniformly dispersed at room temperature, 20% hydrazine hydrate: 1.0 mL are stirred to react
20min is stood overnight, and obtains nano silver/carbon nano tube modified liquid；
(2) nano silver/carbon nano tube modified electrode preparation: glass-carbon electrode is successively carried out with 0.2 μm, 0.01 μm of polishing powder
Then surface polishing is cleaned by ultrasonic with secondary distilled water respectively, ethanol washing, drying, and 15 μ L are added dropwise in glassy carbon electrode surface and receive
Rice gold-graphene decorating liquid, is placed under infrared lamp, to get nano silver/carbon nano tube modified electrode after the dry solvent that volatilizees；
It (preparation of (3) aurantiin molecularly imprinted polymer: in the reactor, is separately added into, ethyl alcohol: 7.8mL, two seasons penta
Tetrol triacrylate: 0.8g, itaconic acid: 0.8g, 1- acrylic -3- ethyl imidazol(e) hexafluorophosphate: 1.8g, two isobutyl of azo
Nitrile: 0.1g, aurantiin: 0.6g, stirring and dissolving lead to 15 min of inert gas deoxygenation, and anaerobic atmosphere, 60 ± 2 DEG C are stirred to react
For 24 hours, the product methanol that will be obtained: acetic acid volume ratio is that 3:1 mixed solution impregnates 14h, removes template molecule, it is dry to get
Aurantiin molecularly imprinted polymer；
(4) preparation method of aurantiin molecular imprinting electrochemical sensor: suitable aurantiin molecularly imprinted polymer is taken
It is scattered in 1% gelatin solution, the aurantiin imprinted polymer solution of 20g/L is made；Then by above-mentioned 20 μ L of solution
It is added drop-wise to nano silver/carbon nano tube modified electrode of step (2) preparation, is placed under infrared lamp, to get shaddock ped after the dry solvent that volatilizees
Glycosides molecular imprinting electrochemical sensor.
Embodiment 4
(1) it nano silver/carbon nano tube modified liquid preparation: in the reactor, is separately added into, deionized water: 8 .2mL, nitric acid
Silver: 0.2g, oxide/carbon nanometer tube: 0.6g, ultrasound 20min, is uniformly dispersed at room temperature, 20% hydrazine hydrate: 1.0 mL are stirred to react
20min is stood overnight, and obtains nano silver/carbon nano tube modified liquid；
(2) nano silver/carbon nano tube modified electrode preparation: glass-carbon electrode is successively carried out with 0.2 μm, 0.01 μm of polishing powder
Then surface polishing is cleaned by ultrasonic with secondary distilled water respectively, ethanol washing, drying, and 12 μ L are added dropwise in glassy carbon electrode surface and receive
Rice gold-graphene decorating liquid, is placed under infrared lamp, to get nano silver/carbon nano tube modified electrode after the dry solvent that volatilizees；
(3) it the preparation of aurantiin molecularly imprinted polymer: in the reactor, is separately added into, ethyl alcohol: 7.6mL, two Ji Wusi
Alcohol triacrylate: 1.0g, itaconic acid: 0.7g, 1- acrylic -3- ethyl imidazol(e) hexafluorophosphate: 1.7g, two isobutyl of azo
Nitrile: 0.2g, aurantiin: 0.4g, stirring and dissolving lead to 15 min of inert gas deoxygenation, and anaerobic atmosphere, 60 ± 2 DEG C are stirred to react
19h, the product methanol that will be obtained: acetic acid volume ratio is that 3:1 mixed solution impregnates 15h, removes template molecule, it is dry to get
Aurantiin molecularly imprinted polymer；
(4) preparation method of aurantiin molecular imprinting electrochemical sensor: suitable aurantiin molecularly imprinted polymer is taken
It is scattered in 1% gelatin solution, the aurantiin imprinted polymer solution of 20g/L is made；Then by above-mentioned 15 μ L of solution
It is added drop-wise to nano silver/carbon nano tube modified electrode of step (2) preparation, is placed under infrared lamp, to get shaddock ped after the dry solvent that volatilizees
Glycosides molecular imprinting electrochemical sensor.
Embodiment 5
By aurantiin molecular imprinting electrochemical sensor prepared by above-described embodiment 1 ~ 4, for the detection of aurantiin, step
It is rapid as follows:
(1) standard solution is prepared: preparing the aurantiin standard solution of one group of various concentration including blank standard specimen, bottom
Liquid is the phosphate buffer solution of pH7.2；
(2) working curve is drawn: being reference electrode by Ag/AgCl, platinum electrode is auxiliary electrode, electricity prepared by the present invention
Extremely working electrode forms three-electrode system, CHI660B electrochemical workstation is connected, in K3[Fe(CN)6] in solution, using following
Ring voltammetry is detected in -0.20 ~ 1.0V potential range, and the response current of blank standard specimen is denoted asI 0 , contain various concentration
The response current of aurantiin standard solution beI i , response current reduce difference be△I=I 0 -I i ,△IWith aurantiin mark
The mass concentration of quasi- solutioncBetween it is in a linear relationship, draw△I ~cWorking curve；
(3) detection of aurantiin: the aurantiin standard solution in step (1) is replaced with sample to be tested, according to step (2)
Method is detected, according to response the difference of current reduction△IAnd working curve, obtain the content of aurantiin in sample to be tested；
The K3[Fe(CN)6] solution concentration be 6.0mmol/L；
The concentration of the phosphate buffer solution of the pH7.2 is in 20m mol/L.
Claims (5)
1. a kind of nano silver/carbon nano tube modified electrode aurantiin molecular engram sensor preparation method, is characterized in that, the party
Method has following processing step:
(1) it nano silver/carbon nano tube modified liquid preparation: in the reactor, is added by following composition mass percentage concentration, deionization
Water: 78~84%, silver nitrate: 2.0~5.0%, oxide/carbon nanometer tube: 3~8%, ultrasound 20min, is uniformly dispersed at room temperature, then
Addition mass percentage concentration is 20% hydrazine hydrate: 10~15%, the sum of each component content is absolutely, to be stirred to react 20min,
It stands overnight, obtains nano silver/carbon nano tube modified liquid；
(2) glass-carbon electrode successively nano silver/carbon nano tube modified electrode preparation: is subjected to surface with 0.2 μm, 0.01 μm of polishing powder
Polishing, is then cleaned by ultrasonic with secondary distilled water, ethanol washing respectively, is dried up, and 15~18 μ L are added dropwise in glassy carbon electrode surface and receive
Rice silver/carbon nanotube decorating liquid, is placed under infrared lamp, to get nano silver/carbon nano tube modified electrode after the dry solvent that volatilizees；
(3) it the preparation of aurantiin molecularly imprinted polymer: in the reactor, is added by following composition mass percentage concentration, ethyl alcohol:
52~62%, dipentaerythritol triacrylate: 8~15%, itaconic acid: 5~10%, 1- acrylic -3- ethyl imidazol(e) hexafluoro
Phosphate: 10~18%, azodiisobutyronitrile: 1.0~3.0%, aurantiin: 4.0~10%, the sum of each component content is percentage
Hundred, stirring and dissolving leads to inert gas deoxygenation 15min, anaerobic atmosphere, 60 ± 2 DEG C be stirred to react 18~for 24 hours, the production that will be obtained
Object methanol: acetic acid volume ratio is that 3:1 mixed solution impregnates 12~15h, removes template molecule, dry to get aurantiin molecule
Imprinted polymer；
(4) preparation of aurantiin molecular imprinting electrochemical sensor: suitable aurantiin molecularly imprinted polymer is taken to be scattered in 1%
Gelatin solution in, be made 20g/L aurantiin imprinted polymer solution；Then above-mentioned 15~20 μ L of solution is added drop-wise to
Nano silver/carbon nano tube modified electrode of step (2) preparation, is placed under infrared lamp, to get aurantiin molecule after the dry solvent that volatilizees
Trace electrochemical sensor.
2. a kind of nano silver according to claim 1/carbon nano tube modified electrode aurantiin molecular engram sensor system
Preparation Method is characterized in that the mass ratio of silver nitrate described in step (1) and oxide/carbon nanometer tube is 1:2~3.
3. a kind of nano silver according to claim 1/carbon nano tube modified electrode aurantiin molecular engram sensor system
Preparation Method is characterized in that, dipentaerythritol triacrylate described in step (3): itaconic acid: 1- acrylic -3- ethyl miaow
Azoles hexafluorophosphate mole be 1:1:1.
4. a kind of nano silver according to claim 1/carbon nano tube modified electrode aurantiin molecular engram sensor system
Preparation Method is characterized in that inert gas described in step (3) is neon or argon gas.
5. a kind of nano silver according to claim 1/carbon nano tube modified electrode aurantiin molecular engram sensor system
Preparation Method is characterized in that anaerobic atmosphere described in step (3) is that polymerization process is passed through always inert gas.
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| CN108760849A (en) * | 2018-06-19 | 2018-11-06 | 孙大明 | A kind of preparation method of the molecularly imprinted polymer modified electrode of quick detection Ofloxacin |
| CN109142498B (en) * | 2018-08-29 | 2020-09-04 | 济南大学 | Preparation method of paraquat molecular imprinting sensor |
| CN109001285B (en) * | 2018-08-29 | 2020-06-23 | 济南大学 | Preparation method of prometryn molecular imprinting sensor |
| CN109324097A (en) * | 2018-10-11 | 2019-02-12 | 大连大学 | A kind of electrode and its application for melamine measurement |
| CN111551618B (en) * | 2020-04-09 | 2022-05-10 | 济南大学 | Preparation method of sirolimus molecularly imprinted erbium nitride composite paste electrode |
| CN115096976B (en) * | 2022-06-20 | 2024-01-26 | 商丘师范学院 | Silver cluster/nitrogen-doped carbon electrode material, in-situ finite field synthesis method and application thereof |
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