CN107102054B - It is a kind of for detecting the preparation method of ginsenoside Re's molecular engram sensor - Google Patents
It is a kind of for detecting the preparation method of ginsenoside Re's molecular engram sensor Download PDFInfo
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Abstract
The invention discloses a kind of for detecting the preparation method of ginsenoside Re's molecular engram sensor, is modified first using copper acetate and graphene oxide glass-carbon electrode, obtains Nanometer Copper/graphene modified electrode；Then, it is added in the reactor, methanol: 40 ~ 50%, divinylbenzene ethyleneglycol dimethacrylate: 12 ~ 18%, methyl acrylate: 4 ~ 10%, vinylpyridine: 5 ~ 12%, azobisisoheptonitrile: 1.0 ~ 3.0%, ginsenoside Re: 20 ~ 25%, the sum of each component content is absolutely, stirring and dissolving, logical 15 min of nitrogen deoxygenation, anaerobic atmosphere, 55 ± 2 DEG C are stirred to react 24 ~ 28h, drying is to get ginsenoside Re's polymer；Polymer drops are coated onto modified electrode again, template molecule is removed using methanol and acetic acid mixed solution, ginsenoside Re's molecular imprinting electrochemical sensor is made.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
Be related to it is a kind of for detecting the preparation method of ginsenoside Re's molecular engram sensor, for detecting drug, food, biological sample
In ginsenoside Re.
Background technique
Ginsenoside (Ginsenoside) is a kind of steroid compound, triterpenoid saponin.It is primarily present in Panax medicinal material
In.Ginsenoside is considered to be the active constituent in ginseng, thus becomes the target of research.Because ginsenoside affects multiple
Metabolic pathway, so its efficiency is also complicated, and the monomer component of various ginsenosides is to be difficult to separate and detect
Come.Contain a variety of active ingredients in ginseng, ginsenoside is main active in ginseng, and ginsenoside monomer is separated
46 kinds are identified, wherein Re and Rg1 belongs to triol saponins.Ginsenoside Re has the function of anti-arrhythmia and liver protection,
Rg1 shows as promoting central nervous excitation, intelligence development, promote the synthesis of protein, DNA and RNA and there is enhancing immunity of organisms etc.
Effect.The main sorting method of Re has thin-layered chromatography, high performance liquid chromatography, Flavonoids by Macroporous Adsorption Resin etc., but similar to its
The separation of the object Re drawback big there are separating difficulty.Molecular structure is close to be difficult to separate and detect.
Ginsenoside Re, molecular formula C48H82O18, relative molecular mass 947.14, ginsenoside Re is Fourth Ring three
Terpene derivant, colorless needle crystals are soluble in methanol, ethyl alcohol, do not dissolve in ether, benzene.Inhibit nervous centralis, promote DNA,
RNA synthesis.The effect of plasma corticosterone is increased, blood vessel is expanded.It can be reduced the contraction in guinea pig in vitro uterus caused by acetylcholine.
There are reducing heart rate and Bipolar blood pressure (falling after rising) effect to rat.Behavior and electroencephalogram to cat show medium inhibition.
There is antifatigue effect.
Currently, the method for detection ginsenoside Re mainly has high performance liquid chromatography, liquid chromatography-mass spectrography, chromatographic standard
Exactness, which is subject to certain restrictions, and instrument is somewhat expensive needs professional to operate, and also limits its application.In addition, due to Re with
Other flavonoids molecular structures are very close to be difficult to separate, and when measurement interferes with each other, and accurate to detect ginsenoside Re highly difficult.Cause
This, finds a kind of good selectivity, high sensitivity, the method for the detection ginsenoside Re easy to operate being used for and uses valence with important
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, to ginsenoside Re's content accurate quantitative analysis in food, drug, biological sample
It measures very necessary.
Summary of the invention
The purpose of the present invention is combining molecular engram with electrochemical sensor, a kind of Nanometer Copper/graphene is provided
The preparation method of modified electrode ginsenoside Re's molecular engram sensor, mainly using ginsenoside Re as template, in glass carbon electricity
Pole surface passes through the modification of graphene oxide, nanometer copper particle, improves the sensitivity of sensor, prepares people using drop coating legal system
Join saponin(e Re molecular imprinting electrochemical sensor.
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).
Graphene oxide；Divinylbenzene ethylene glycol dimethacrylate, methyl acrylate；Vinylpyridine, azo two
Different heptonitrile, methanol, ethyl alcohol；Ginsenoside Re；Copper acetate；Polyvinyl alcohol；Hydrazine hydrate, phosphate buffer solution；Agents useful for same is
Analyze pure, experimental water is secondary distilled water.
The purpose of the present invention is achieved through the following technical solutions.
It is a kind of to be characterized in that for detecting the preparation method of ginsenoside Re's molecular engram sensor, this method have with
Lower processing step:
(1) Nanometer Copper/graphene modified liquid preparation: in the reactor, being added by following composition mass percentage concentration, go from
Sub- water: 80~86%, copper acetate: 2.0~5.0%, graphene oxide: 6~12%, ultrasound 20min, is uniformly dispersed at room temperature,
Add hydrazine hydrate: 4~8%, the sum of each component content is absolutely, to be heated to 60 ± 2 DEG C, be stirred to react 60min, obtain
Nanometer Copper/graphene modified liquid；
(2) glass-carbon electrode successively Nanometer Copper/graphene modified electrode preparation: is subjected to table with 0.2 μm, 0.01 μm of polishing powder
Face 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
Nanometer Copper/graphene modified liquid, is placed under infrared lamp, to get Nanometer Copper/graphene modified electrode preparation after the dry solvent that volatilizees；
(3) it the preparation of ginsenoside Re's polymer: in the reactor, is added by following composition mass percentage concentration, methanol:
40~50%, divinylbenzene ethylene glycol dimethacrylate: 12~18%, methyl acrylate: 4~10%, vinylpyridine:
5~12%, azobisisoheptonitrile: 1.0~3.0%, ginsenoside Re: 20~25%, the sum of each component content is a hundred percent,
Stirring and dissolving leads to nitrogen deoxygenation 15min, and anaerobic atmosphere, 55 ± 2 DEG C are stirred to react 24~28h, dry to get ginsenoside
Re polymer；
(4) preparation method of ginsenoside Re's molecular imprinting electrochemical sensor: suitable ginsenoside Re's polymer is taken
It is scattered in 1% gelatin solution, ginsenoside Re's polymer solution of 20g/L is made；Then by above-mentioned 12~15 μ L of solution
It is added drop-wise to Nanometer Copper/graphene modified electrode of step (2) preparation, is placed under infrared lamp, is volatilized after dry solvent, electrode is impregnated
In 12~15h of methanol and acetic acid mixed solution that volume ratio is 8:1, template molecule is removed to get ginsenoside Re's molecular engram
Electrochemical sensor.
The mass ratio of the copper acetate described in step (1) and graphene oxide is 1:3.
The methyl acrylate described in step (3) and vinylpyridine mole are 1:1.
The anaerobic atmosphere described in step (3) is that polymerization process is passed through always nitrogen.
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 ginsenoside Re's trace electrochemical sensor with specific selectivity.By with nanometer
That the response of the molecular engram electrode of silver/carbon nanotube modification is compared, ginsenoside Re's molecule print prepared by the present invention
The response of mark sensor greatly improves.The trace sensor shows higher compatibility and selectivity to ginsenoside Re, rings
Answer the concentration of electric current and ginsenoside Re 1.0 × 10-7~1.0 × 10-4It is in good linear relationship, detection within the scope of mol/L
It is limited to 1.76 × 10-8Ginsenoside Re's molecular imprinting electrochemical sensor prepared by the present invention is used successfully to drug, food by mol/L
In product, biological sample in the detection of ginsenoside Re, the rate of recovery is therefore prepared by the present invention between 96.62~105.32%
Ginsenoside Re's molecular engram sensor can be widely applied to the related fieldss such as chemical industry, biological medicine, food, environmental protection tests.
Specific embodiment
Embodiment 1
(1) it Nanometer Copper/graphene modified liquid preparation: in the reactor, is separately added into, deionized water: 83mL, copper acetate:
4g, graphene oxide: 8g, ultrasound 20min: the 5g that is uniformly dispersed, adds hydrazine hydrate are heated to 60 ± 2 DEG C, stirring at room temperature
60min is reacted, Nanometer Copper/graphene modified liquid is obtained；
(2) glass-carbon electrode successively Nanometer Copper/graphene modified electrode preparation: is subjected to table with 0.2 μm, 0.01 μm of polishing powder
Face polishing, is then cleaned by ultrasonic with secondary distilled water, ethanol washing respectively, is dried up, and L nanometers of 17 μ is added dropwise in glassy carbon electrode surface
Copper/graphene modified liquid, is placed under infrared lamp, to get Nanometer Copper/graphene modified electrode preparation after the dry solvent that volatilizees；
(3) it the preparation of ginsenoside Re's polymer: in the reactor, is separately added into, methanol: 57mL, divinylbenzene second two
Alcohol dimethylacrylate: 15g, methyl acrylate: 7g, vinylpyridine: 8g, azobisisoheptonitrile: 2.0g, ginsenoside
Re:23g, stirring and dissolving lead to nitrogen deoxygenation 15min, and anaerobic atmosphere, 55 ± 2 DEG C are stirred to react 25h, dry to get ginseng soap
Glycosides Re polymer；
(4) preparation method of ginsenoside Re's molecular imprinting electrochemical sensor: suitable ginsenoside Re's polymer is taken
It is scattered in 1% gelatin solution, ginsenoside Re's polymer solution of 20g/L is made；Then above-mentioned 13 μ L of solution is added dropwise
To Nanometer Copper/graphene modified electrode of step (2) preparation, it is placed under infrared lamp, after the dry solvent that volatilizees, electrode is immersed in body
Product removes template molecule than the methanol and acetic acid mixed solution 13h that are 8:1 to get ginsenoside Re's molecular imprinting electrochemical biography
Sensor.
Embodiment 2
(1) it Nanometer Copper/graphene modified liquid preparation: in the reactor, is separately added into, deionized water: 86mL, copper acetate:
2g, graphene oxide: 6g, ultrasound 20min: the 6g that is uniformly dispersed, adds hydrazine hydrate are heated to 60 ± 2 DEG C, stirring at room temperature
60min is reacted, Nanometer Copper/graphene modified liquid is obtained；
(2) glass-carbon electrode successively Nanometer Copper/graphene modified electrode preparation: is subjected to table with 0.2 μm, 0.01 μm of polishing powder
Face polishing, is then cleaned by ultrasonic with secondary distilled water, ethanol washing respectively, is dried up, and L nanometers of 16 μ is added dropwise in glassy carbon electrode surface
Copper/graphene modified liquid, is placed under infrared lamp, to get Nanometer Copper/graphene modified electrode preparation after the dry solvent that volatilizees；
(3) it the preparation of ginsenoside Re's polymer: in the reactor, is separately added into, methanol: 51mL, divinylbenzene second two
Alcohol dimethylacrylate: 18g, methyl acrylate: 10g, vinylpyridine: 6g, azobisisoheptonitrile: 1.0g, ginsenoside
Re:25g, stirring and dissolving lead to nitrogen deoxygenation 15min, and anaerobic atmosphere, 55 ± 2 DEG C are stirred to react 26h, dry to get ginseng soap
Glycosides Re polymer；
(4) preparation method of ginsenoside Re's molecular imprinting electrochemical sensor: suitable ginsenoside Re's polymer is taken
It is scattered in 1% gelatin solution, ginsenoside Re's polymer solution of 20g/L is made；Then above-mentioned 14 μ L of solution is added dropwise
To Nanometer Copper/graphene modified electrode of step (2) preparation, it is placed under infrared lamp, after the dry solvent that volatilizees, electrode is immersed in body
Product removes template molecule than the methanol and acetic acid mixed solution 14h that are 8:1 to get ginsenoside Re's molecular imprinting electrochemical biography
Sensor.
Embodiment 3
(1) it Nanometer Copper/graphene modified liquid preparation: in the reactor, is separately added into, deionized water: 80mL, copper acetate:
5g, graphene oxide: 12g, ultrasound 20min: the 3g that is uniformly dispersed, adds hydrazine hydrate are heated to 60 ± 2 DEG C, stirring at room temperature
60min is reacted, Nanometer Copper/graphene modified liquid is obtained；
(2) glass-carbon electrode successively Nanometer Copper/graphene modified electrode preparation: is subjected to table with 0.2 μm, 0.01 μm of polishing powder
Face polishing, is then cleaned by ultrasonic with secondary distilled water, ethanol washing respectively, is dried up, and L nanometers of 15 μ is added dropwise in glassy carbon electrode surface
Copper/graphene modified liquid, is placed under infrared lamp, to get Nanometer Copper/graphene modified electrode preparation after the dry solvent that volatilizees；
(3) it the preparation of ginsenoside Re's polymer: in the reactor, is separately added into, methanol: 63mL, divinylbenzene second two
Alcohol dimethylacrylate: 16g, methyl acrylate: 6g, vinylpyridine: 5g, azobisisoheptonitrile: 3.0g, ginsenoside
Re:20g, stirring and dissolving lead to nitrogen deoxygenation 15min, and anaerobic atmosphere, 55 ± 2 DEG C are stirred to react for 24 hours, dry to get ginseng soap
Glycosides Re polymer；
(4) preparation method of ginsenoside Re's molecular imprinting electrochemical sensor: suitable ginsenoside Re's polymer is taken
It is scattered in 1% gelatin solution, ginsenoside Re's polymer solution of 20g/L is made；Then above-mentioned 13 μ L of solution is added dropwise
To Nanometer Copper/graphene modified electrode of step (2) preparation, it is placed under infrared lamp, after the dry solvent that volatilizees, electrode is immersed in body
Product removes template molecule than the methanol and acetic acid mixed solution 13h that are 8:1 to get ginsenoside Re's molecular imprinting electrochemical biography
Sensor.
Embodiment 4
(1) it Nanometer Copper/graphene modified liquid preparation: in the reactor, is separately added into, deionized water: 82mL, copper acetate:
3g, graphene oxide: 10g, ultrasound 20min: the 5g that is uniformly dispersed, adds hydrazine hydrate are heated to 60 ± 2 DEG C, stirring at room temperature
60min is reacted, Nanometer Copper/graphene modified liquid is obtained；
(2) glass-carbon electrode successively Nanometer Copper/graphene modified electrode preparation: is subjected to table with 0.2 μm, 0.01 μm of polishing powder
Face polishing, is then cleaned by ultrasonic with secondary distilled water, ethanol washing respectively, is dried up, and L nanometers of 18 μ is added dropwise in glassy carbon electrode surface
Copper/graphene modified liquid, is placed under infrared lamp, to get Nanometer Copper/graphene modified electrode preparation after the dry solvent that volatilizees；
(3) it the preparation of ginsenoside Re's polymer: in the reactor, is separately added into, methanol: 61mL, divinylbenzene second two
Alcohol dimethylacrylate: 12g, methyl acrylate: 4g, vinylpyridine: 10g, azobisisoheptonitrile: 2.0g, ginsenoside
Re:24g, stirring and dissolving lead to nitrogen deoxygenation 15min, and anaerobic atmosphere, 55 ± 2 DEG C are stirred to react 28h, dry to get ginseng soap
Glycosides Re polymer；
(4) preparation method of ginsenoside Re's molecular imprinting electrochemical sensor: suitable ginsenoside Re's polymer is taken
It is scattered in 1% gelatin solution, ginsenoside Re's polymer solution of 20g/L is made；Then above-mentioned 15 μ L of solution is added dropwise
To Nanometer Copper/graphene modified electrode of step (2) preparation, it is placed under infrared lamp, after the dry solvent that volatilizees, electrode is immersed in body
Product removes template molecule than the methanol and acetic acid mixed solution 15h that are 8:1 to get ginsenoside Re's molecular imprinting electrochemical biography
Sensor.
Embodiment 5
By ginsenoside Re's molecular imprinting electrochemical sensor prepared by above-described embodiment 1~4, it to be used for ginsenoside Re
Detection, steps are as follows:
(1) standard solution is prepared: the ginsenoside Re's standard for preparing one group of various concentration including blank standard specimen is molten
Liquid, bottom liquid are the phosphate buffer solution of pH7.0；
(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 as I0, contain various concentration
The response current of ginsenoside Re's standard solution be Ii, the difference that response current reduces is △ I=I0-Ii, △ I and ginseng
It is in a linear relationship between the mass concentration c of saponin(e Re standard solution, draw △ I~c working curve；
(3) detection of ginsenoside Re: replacing ginsenoside Re's standard solution in step (1) with sample to be tested, according to
The method of step (2) is detected, and the difference △ I and working curve of current reduction, obtain ginseng in sample to be tested according to response
The content of saponin(e Re；
The K3[Fe(CN)6] solution concentration be 1.0mmol/L；
The concentration of the phosphate buffer solution of the pH7.0 is in 40m mol/L.
Claims (5)
1. it is a kind of for detecting the preparation method of ginsenoside Re's molecular engram sensor, it is characterized in that, this method has following
Processing step:
(1) it Nanometer Copper/graphene modified liquid preparation: in the reactor, is added by following composition mass percentage concentration, deionization
Water: 80~86%, copper acetate: 2.0~5.0%, graphene oxide: 6~12%, ultrasound 20min, is uniformly dispersed at room temperature, then
Addition hydrazine hydrate: 4~8%, the sum of each component content is absolutely, to be heated to 60 ± 2 DEG C, be stirred to react 60min, received
Rice copper/graphene modified liquid；
(2) glass-carbon electrode successively Nanometer Copper/graphene modified electrode preparation: is subjected to surface throwing with 0.2 μm, 0.01 μm of polishing powder
Then light is cleaned by ultrasonic with secondary distilled water respectively, ethanol washing, drying, and L nanometers of 15~18 μ is added dropwise in glassy carbon electrode surface
Copper/graphene modified liquid, is placed under infrared lamp, to get Nanometer Copper/graphene modified electrode preparation after the dry solvent that volatilizees；
(3) it the preparation of ginsenoside Re's polymer: in the reactor, is added by following composition mass percentage concentration, methanol: 40~
50%, divinylbenzene ethylene glycol dimethacrylate: 12~18%, methyl acrylate: 4~10%, vinylpyridine: 5~
12%, azobisisoheptonitrile: 1.0~3.0%, ginsenoside Re: 20~25%, the sum of each component content is absolutely, to stir
Dissolution is mixed, leads to nitrogen deoxygenation 15min, anaerobic atmosphere, 55 ± 2 DEG C are stirred to react 24~28h, dry to get ginsenoside Re
Polymer；
(4) preparation method of ginsenoside Re's molecular imprinting electrochemical sensor: suitable ginsenoside Re's polymer is taken to disperse
In 1% gelatin solution, ginsenoside Re's polymer solution of 20g/L is made；Then above-mentioned 12~15 μ L of solution is added dropwise
To Nanometer Copper/graphene modified electrode of step (2) preparation, it is placed under infrared lamp, after the dry solvent that volatilizees, electrode is immersed in body
Product removes template molecule than the 12~15h of methanol and acetic acid mixed solution for being 8:1 to get ginsenoside Re's molecular engram electrification
Learn sensor.
2. according to claim 1 a kind of for detecting the preparation method of ginsenoside Re's molecular engram sensor, feature
It is, the mass ratio of copper acetate described in step (1) and graphene oxide is 1:3.
3. according to claim 1 a kind of for detecting the preparation method of ginsenoside Re's molecular engram sensor, feature
It is, methyl acrylate described in step (3) and vinylpyridine mole are 1:1.
4. according to claim 1 a kind of for detecting the preparation method of ginsenoside Re's molecular engram sensor, feature
It is, anaerobic atmosphere described in step (3) is that polymerization process is passed through always nitrogen.
5. prepared by a kind of preparation method for detecting ginsenoside Re's molecular engram sensor according to claim 1
Ginseng saponin(e Re molecular engram sensor.
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