CN103175884A - High-sensitivity glucose biosensor and preparation method thereof - Google Patents
High-sensitivity glucose biosensor and preparation method thereof Download PDFInfo
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- CN103175884A CN103175884A CN2013100871775A CN201310087177A CN103175884A CN 103175884 A CN103175884 A CN 103175884A CN 2013100871775 A CN2013100871775 A CN 2013100871775A CN 201310087177 A CN201310087177 A CN 201310087177A CN 103175884 A CN103175884 A CN 103175884A
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Abstract
The invention relates to a high -ensitivity glucose biosensor and a preparation method thereof. The preparation method comprises the steps of: putting a polished platinum electrode into a mixed solution of K2PdCl4 and sulfuric acid, carrying out electrodeposition to obtain a platinum electrode modified by palladium nano-particles, dissolving glucose oxidase and bovine serum albumin into a phosphate buffered solution, then adding a glutaraldehyde solution and a single-walled carbon nanotube solution treated by acid treatment into the phosphate buffered solution, mixing to obtain an enzyme solution, and dipping the platinum electrode modified by the palladium nano-particles in the enzyme solution to obtain the glucose biosensor. The high-sensitivity glucose biosensor and the preparation method thereof have the characteristics of simple electrode manufacturing and modifying method, high sensitivity, good stability and low detection limit compared with other methods of electrochemically detecting glucose.
Description
Technical field
The present invention relates generally to a kind of biology sensor and preparation method thereof, belongs to Electroanalytical Chemistry detection technique field.
Background technology
Glucose is a kind of material very important in organism, and the document that detects in recent years glucose content is a lot, but their a lot of detected objects are all serum, tissue fluid and cell liquid etc.The method that is widely used in detecting glucose is a lot, as spectrophotometric method, fluoroscopic examination, chemoluminescence method, electrochemical methods etc., and these methods all successfully being used for Capillary Electrophoresis detects glucose.
Electrochemical analysis method is highly sensitive, and amount of samples is few, and instrument is simple, and price is relatively cheap, therefore is widely used.Detect a lot of of glucose with electrochemical method in recent years, electrochemical method detects glucose and normally utilizes glucose dehydrogenase or glucose oxidase, makes enzyme biologic sensor.Enzyme biologic sensor is as the bio-sensing primitive with enzyme, by the reaction between various physics, chemical signal converter captured target thing and responsive primitive that produce with the signal the surveyed proportional relation of object concentration, realize the analytical instrument to the object quantitative measurement.Compare with other analytical approach, that electrochemica biological sensor has is portable, cost is low, highly sensitive, the advantage such as have good stability, and adds catalysis and the enhancement effect of CNTs itself, makes the enzyme biologic sensor based on CNTs have broad application prospects.
Chemically modified electrode is one of research field of present most active galvanochemistry and Electroanalytical Chemistry, give electrode certain specific character, can high selectivity carry out desired reaction, the overpotential that has occurred when having overcome the unmodified determination of electrode is higher, reaction velocity waits shortcoming slowly, even can be used for detecting and there is no electroactive material, especially be widely used aspect the preparation of biology sensor in the analytical chemistry field.Chemically modified electrode commonly used has Hg to modify microelectrode, the carbon magma microelectrode, and little metallic particles is modified microelectrode, the film modified microelectrode of surface molecular, powder microelectrode, enzyme electrode etc.
there is the potpourri with TiO2-MWNTs-CS to be modified on glass-carbon electrode in prior art, and then with the surface of Prussian blue electro-deposition at modified electrode, at last glucose oxidase and gold nano grain are adsorbed on (the Zhang M.H. that the glucose biological sensor of making on Prussian blue detects the content of glucose, Yuan R., Chai Y.Q., Li W.J., Zhong H.A., Wang C.Glucose biosensor based on titanium dioxide-multiwall carbon nanotubes-chitosan composite and functionalized gold nanoparticles[J] .Bioprocess Biosyst.Eng., 2011, 34:1143-1150.).Having with Pt and the Pd nano particle method by electro-deposition to be fixed on MWCNTs makes glucose biological sensor and detects glucose, (Cui H.F, Ye J.S, Zhang W.D, Li C.M, Luong J.H.T., Sheu F.S.Selective and sensitive electrochemical detection of glucose in neutral solution using platinum – lead alloy nanoparticle/carbon nanotube nanocomposites[J] .Analytica Chimica Acta2007,594:175-183.).Document (Reitz E, Jia W, Gentile M, Wang Y, Lei Y.CuO Nanospheres Based Nonenzymatic Glucose Sensor[J] .Electroanalysis, 2008, the CuO nanosphere is fixed on glass-carbon electrode in 20:2482.), fixingly go up the Nafion film preparation and become one without enzyme biologic sensor.These biology sensors or preparation method are complicated, or sensitivity, stability are good not.
Summary of the invention
The objective of the invention is to overcome the prior art deficiency and provide a kind of high sensitivity glucose biological sensor and preparation method thereof, the method to be simple and easy to do, the transducer sensitivity that makes is high, and detectability is low, and antijamming capability is strong.
The technical scheme that the present invention takes is:
A kind of high sensitivity glucose biological sensor comprises plating palladium platinum electrode, is distributed in plating palladium platinum electrode surface and hands over the carbon nano-tube that reticulates structure, and the glucose oxidase of electrode and the load of carbon nano-tube institute.
A kind of preparation method of high sensitivity glucose biological sensor comprises that step is as follows:
(1) the good platinum electrode of polishing is placed in K
2PdCl
4In the mixed solution of sulfuric acid, the electro-deposition current potential be made as-0.1 to-0.5V(vs.SCE), electro-deposition 10-15s rinses, dries and to get the platinum electrode modified of palladium nano-particles;
(2) preparation enzyme solutions: glucose oxidase and bovine serum albumin(BSA) are dissolved in phosphate buffered solution, and then add the Single Walled Carbon Nanotube solution of glutaraldehyde solution and acid treatment, mix this enzyme solutions stand-by; The concentration 908U/mL(of glucose oxidase in enzyme solutions is 109U/mg according to the activity of glucose oxidase, be equivalent to 8.3mg/mL), the mass ratio of glucose oxidase and bovine serum albumin(BSA) is 1:1-10, the concentration of glutaraldehyde in enzyme solutions is 8-10mg/mL, phosphate buffered solution pH6.0～8.0, the concentration of Single Walled Carbon Nanotube solution in enzyme solutions of acid treatment is 0.2-1.0mg/mL;
(3) platinum electrode of palladium nano-particles being modified dips 3-5 time in enzyme solutions, and the time that at every turn dips is 10～15s.
In the mixed solution of the described K2PdCl4 of step (1) and sulfuric acid, K2PdCl4 concentration is 1 * 10
-3Mol/L, H
2SO
4Concentration is 0.5mol/L.The preferred current potential of described electro-deposition is made as-0.2V(vs.SCE), and electro-deposition 15s.
The preparation method of the Single Walled Carbon Nanotube solution of the described acid treatment of step (2) adds every gram Single Walled Carbon Nanotube and adds hot reflux 6-6.5h in 400mL6mol/L nitric acid, cooled and filtered, be washed to neutrality with second distillation, put into baking oven dry, then with redistilled water, it be mixed with the aqueous solution that concentration is 10mg/mL..
Phosphate buffered solution is 0.2754～2.1202g Na
2HPO
412H
2O and 0.0517～0.8553g NaH
2PO
42H
2O is formulated in the volumetric flask of 250mL and is made into.
The present invention forms the palladium particle of very regular arrangement by being electrochemically-deposited in platinum electrode surface, the platinum electrode surface of plating palladium has many porous structures, the structure of this porous has increased the specific surface area of electrode, increased the charge capacity of enzyme at electrode surface, thereby the catalytic activity point is rolled up, promote the transfer rate of electronics, improved the sensitivity of current-responsive.The surface of electrode is comparatively smooth, the carbon nano-tube of sensor surface is crosslinked together, formed a huge reticulate texture, this structure is conducive to the conduction of electronics, the specific surface area that carbon nano-tube is large has also increased the charge capacity of enzyme at electrode surface, to improving current-responsive sensitivity, certain contribution is arranged.
The palladium nano-particles of sensor surface and carbon nano-tube have the effect that promotes that electronics shifts, and increase the specific surface area of electrode, strengthen catalytic activity, have improved detection sensitivity.Utilize the high selectivity of enzyme in this biology sensor and avoided the interference of other material to realize the detection fast and accurately of glucose in the blood of human body.The detection of sensor glucose of the present invention simultaneously is limited to 5 * 10
-7Mol/L, detectability is low.The present invention has electrode fabrication, method of modifying is simple, and is highly sensitive, and good stability is than the low characteristics of detectability of other Electrochemical Detection glucose method.
Description of drawings
Fig. 1 is the scan-type electrochemical microscope figure that the present invention plates the palladium platinum electrode.
Fig. 2 is the scan-type electrochemical microscope figure of glucose biological sensor of the present invention.
Fig. 3 is the installation drawing of kapillary Electrochemical Detection glucose of the present invention.
Fig. 4 is the detection cell of kapillary Electrochemical Detection glucose of the present invention.
Fig. 5 is the electrophoretic image of interfering material compound sample of the present invention, a-DA (0.2mM), b-glucose (0.6mM), c-halfcystine (0.5mM), d-AA (0.5mM), e-UA (0.8mM).
Fig. 6 is the electrophoretic image of glucose in Standard Addition Method for Determination human serum of the present invention, a.0, and b.0.6mmol/L glucose, c.1.0mmol/L glucose.
Wherein, 1, working electrode, 2, contrast electrode, 3, to electrode, 4, quartz glass capillary, 5, reference cell, 6, detection cell, 7 connecting pipes, 8, high-voltage power supply, 9, sampling system, 10, collection system, 11, detection cell, 12, kapillary, 13, negative pole, 14, positive pole.
Embodiment
Further illustrate below in conjunction with embodiment.
Embodiment 1 is most preferred embodiment
(1) preparation of the platinum electrode of palladium nano-particles modification: be 200 μ m with a diameter, the platinum filament that length is approximately 5cm penetrates one section quartz capillary (250 μ m I.D. that are about 3cm length, 375 μ mO.D.) in, make quartz capillary two ends expose simultaneously platinum filament, the one end is coated with full epoxide-resin glue, slowly draw back from an other end, platinum filament is just revealed to the kapillary port, and make it to be full of epoxide-resin glue, after 24h, treat adhesive curing.The copper wire of one section 5cm of intercepting, polishing is level and smooth on abrasive paper for metallograph, the platinum filament that is exposed is wound on copper wire, be coated with full conductive silver glue in winding place, be placed in baking oven and dry by the fire 30min under 70 ℃, last again with one approximately the glass tube (400 μ m I.D., 700 μ m O.D.) grown of 5cm be placed on platinum filament and copper wire interface, cling the two ends of glass tube with epoxide-resin glue, can use after drying in the air 24 hours.With thin abrasive paper for metallograph, that electrode polishing is level and smooth, make the platinum filament cross section concordant with the kapillary cross section, the platinum electrode that polishing is got well is each ultrasonic 5min in intermediate water, absolute ethyl alcohol, intermediate water respectively, and cleaned platinum electrode is placed in and contains 1 * 10
-3Mol/L K
2PdCl
40.5mol/L H
2SO
4Mixed liquor in, the electro-deposition current potential is made as-0.2V(vs.SCE), electro-deposition 15s.After electro-deposition is completed, with intermediate water, working electrode is rinsed well, obtained the microelectrode that palladium nano-particles is modified, naturally dry under room temperature environment.
(2) preparation enzyme solutions: preparation enzyme solutions: glucose oxidase and bovine serum albumin(BSA) are dissolved in phosphate buffered solution, and then add the Single Walled Carbon Nanotube solution of glutaraldehyde solution and acid treatment, mix this enzyme solutions stand-by; The mass ratio of glucose oxidase and bovine serum albumin(BSA) is 1:5, the concentration of glucose oxidase in enzyme solutions is 8.3mg/mL, and the concentration of glutaraldehyde in enzyme solutions is 9mg/mL, the concentration 0.025mol/L of phosphate buffered solution, pH is 7.4, phosphate buffered solution be 1.8131g Na
2HPO
412H
2O and 0.1853g NaH
2PO
42H
2O is formulated in the volumetric flask of 250mL, and the concentration of Single Walled Carbon Nanotube solution in enzyme solutions of acid treatment is 0.5mg/mL;
(3) platinum electrode of palladium nano-particles being modified dips in enzyme solutions 3 times, and the time that at every turn dips is 10～15s.
Fig. 1 and Fig. 2 are respectively the scanning electron microscope (SEM) photograph of plating palladium platinum electrode and glucose biological sensor.As can be seen from Figure 1, be electrochemically-deposited in the palladium nano-particles of platinum electrode surface very orderly be arranged in platinum electrode surface, promoted the transfer rate of electronics, the sensitivity that has improved current-responsive.As can be seen from Figure 2, the surface of electrode is comparatively smooth, the carbon nano-tube of sensor surface is crosslinked together, formed a huge reticulate texture, this structure is conducive to the conduction of electronics, the specific surface area that carbon nano-tube is large has also increased the charge capacity of enzyme at electrode surface, to improving current-responsive sensitivity, certain contribution is arranged.
Embodiment 2
The mass ratio that changes the middle glucose oxidase of step (2) and bovine serum albumin(BSA) is respectively 1:1,1:3, and 1:8,1:10, other steps are with embodiment 1.
Embodiment 3
The concentration of Single Walled Carbon Nanotube solution in enzyme solutions that changes acid treatment in step (2) is respectively 0.2mg/mL, 0.8mg/mL, and 1.0mg/mL, other steps are with embodiment 1.
Embodiment 4
Changing the middle concentration of glutaraldehyde in enzyme solutions of step (2) is 4mg/mL, 13mg/mL, and 17mg/mL, other steps are with embodiment 1.
Capillary electrophoresis amperometric detects glucose
(1) instrument
The self assembly capillary electrophoresis system, 0-30kV high-voltage power supply (instrument plant of Shandong Normal University, Jinan); Separation capillary (25 μ m I.D, 375 μ m O.D, length 60cm, Yongnian sharp Feng chromatogram device company limited); CHI832b electrochemical workstation (the magnificent Instr Ltd. of Shanghai occasion); Filtrator (0.20 μ m, Solution); Three-electrode system: saturated calomel electrode (contrast electrode), platinum electrode (to electrode), palladium nano-particles are modified microelectrode (working electrode) abrasive paper for metallograph (sand paper WA W5(06), grinding wheel factory, Shanghai, Shanghai); Ultrasonic cleaner (Kunshan Ultrasonic Instruments Co., Ltd., Jiangsu); High purity water distiller (Jintan City brilliant glass experimental apparatus factory, Jiangsu) boils in quartzy Asia; Supercentrifuge (Jintan City Medical Instruments factory, Jiangsu).
(2) method step and the top condition that detect
Detection method step: use the glucose sensor of embodiment 1, before kapillary, clean with sodium hydroxide solution, intermediate water, buffer solution respectively, then utilize the Three dimensional steerable instrument that the kapillary of handling well is alignd with working electrode, high pressure is transferred to 18kV, tests, see whether base current is steady, after if base current is steady, again high pressure is transferred to 5kV, the glucose standard solution sample introduction 10s that configures, accent voltage is 18kV, begin to test, obtain electrophoretogram analysis.
Optimal detection condition: separation voltage is that 18kV, the concentration that detects voltage-0.8V, buffer solution are 0.025mol/L, and pH is 7.4.
Reappearance and detectability
Under above-mentioned detection method and optimal detection condition, to 1 * 10
-3Mol/L glucose standard solution carries out 10 replicate determinations continuously, and the relative standard deviation of glucose peaks electric current and transit time is respectively 3.8% and 1.4%.Under this experiment condition, when signal to noise ratio (S/N ratio) S/N=3, the detection of glucose is limited to 5 * 10
-7Mol/L.Experimental implementation of the present invention, electrode fabrication, method of modifying is simple, and is highly sensitive, and good stability is lower than the detectability of other Electrochemical Detection glucose method.
Table 1 capillary electrophoresis electrochemical detects glucose working electrode used, the range of linearity, detectability contrast
[4]Mattos?I?L,Areias?M?C?C.Automated?determination?of?glucose?in?soluble?coffee?using?Prussian?Blue-glucose
modified?electrode[J].Talanta,2005,66:1281-1286.
[5]Tan?X,Tian?Y?X,Cai?P?X,Zou?X?Y.Glucose?biosensor?based?on?glucose?oxidase?immobilized?in?sol–gel?chitosan/silica?hybrid?composite?film?on?Prussian?blue?modified?glass?carbon?electrode[J].Analytical?and?Bioanalytical?Chemistry,2005,381(2):500-507.
[6]Cui?H?F,Ye?J?S,Zhang?W?D,Li?C?M,Luong?J?H?T,Sheu?F?S.Selective?and?sensitive?electrochemical?detection?of?glucose?in?neutral?solution?using?platinum–leadalloy?nanoparticle/carbon?nanotube?nanocomposites[J].Analytica?Chimica?Acta,2007,594(2):175-183.
[7]Pang?X?Y,He?D?M,Luo?S?L,Cai?Q?Y.An?amperometric?glucose?biosensor?fabricatd?with?Pt?nanoparticle?decorated?carbon?nanotubes/TiO
2nanotubes?arrays?composite[J].Sensors?and?Actuators?B,2009,137:134–138.
[8]Wang?X,Zhang?Y,Cheng?C,Dong?R,Hao?J.Glucose?in?human?serum?determined?by?capillary?electrophoresis?with?glucose?micro-biosensor[J].Analyst,2011,136,1753-1759.
Interference experiment
often contain some electroactive materials such as ascorbic acid (AA) in actual sample, halfcystine (L-Cys), uric acid (UA) etc., these materials can produce the detection that peak current might interfere with glucose in the process of measuring glucose, therefore carry out interference measurement to comprising these materials that may exist, configuration contains glucose, DA, L-Cys, AA, the hybrid standard sample of UA, this biased sample is detected simultaneously, the electrophoretic image that obtains as shown in Figure 5, as can be seen from the figure, their transit time is different from the transit time of glucose, the electrophoresis peak can be separated well with the electrophoresis peak of glucose, therefore can not have influence on the detection of glucose.
The detection of glucose in human serum
Above-mentioned capillary electrophoresis electrochemical detects the detection that can be used for glucose in the human blood sample, detected respectively the concentration of the glucose in two hypertension and two normal human bloods, respectively blood sample is diluted 100 times with 0.025mol/L PB, then directly carry out capillary sample inlet, glucose content in 4 parts of blood serum samples of Standard Addition Method for Determination, wherein the result of 1 duplicate samples as shown in Figure 6.
The result of the assay of glucose in table 2 human serum
Sample 1,3---diabetes patient's serum; Sample 2, the 4---Healthy Human Serum.
As can be seen from Table 2, this method is carried out the detection of glucose in blood and the testing result of hospital meets substantially, but totally slightly little, may be because blood sample is long standing time, causes a small amount of reason of decomposing of glucose.
Claims (6)
1. a high sensitivity glucose biological sensor, is characterized in that, comprises plating palladium platinum electrode, is distributed in plating palladium platinum electrode surface and hands over the carbon nano-tube that reticulates structure, and the glucose oxidase of electrode and the load of carbon nano-tube institute.
2. the preparation method of a high sensitivity glucose biological sensor, is characterized in that, comprises that step is as follows:
(1) the good platinum electrode of polishing is placed in K
2PdCl
4In the mixed solution of sulfuric acid, the electro-deposition current potential is made as-0.1 to-0.5V, and electro-deposition 10-15s rinses, dries and to get the platinum electrode modified of palladium nano-particles;
(2) preparation enzyme solutions: glucose oxidase and bovine serum albumin(BSA) are dissolved in phosphate buffered solution, and then add the Single Walled Carbon Nanotube solution of glutaraldehyde solution and acid treatment, mix this enzyme solutions stand-by; The mass ratio of glucose oxidase and bovine serum albumin(BSA) is 1:1-10, the concentration 8.3mg/mL of glucose oxidase in enzyme solutions, the concentration of glutaraldehyde in enzyme solutions is 8-10mg/mL, phosphate buffered solution pH6.0～8.0, the concentration of Single Walled Carbon Nanotube solution in enzyme solutions of acid treatment is 0.2-1.0mg/mL;
(3) platinum electrode of palladium nano-particles being modified dips 3-5 time in enzyme solutions, and the time that at every turn dips is 10～15s.
3. the preparation method of a kind of high sensitivity glucose biological sensor according to claim 2, is characterized in that, the described K of step (1)
2PdCl
4In the mixed solution of sulfuric acid, K
2PdCl
4Concentration is 1 * 10
-3Mol/L, H
2SO
4Concentration is 0.5mol/L.
4. the preparation method of a kind of high sensitivity glucose biological sensor according to claim 2, is characterized in that, described electro-deposition selects current potential to be made as-0.2V, electro-deposition 15s.
5. the preparation method of a kind of high sensitivity glucose biological sensor according to claim 2, it is characterized in that, the preparation method of the Single Walled Carbon Nanotube solution of the described acid treatment of step (2) adds every gram Single Walled Carbon Nanotube and adds hot reflux 6-6.5h in 400mL6mol/L nitric acid, cooled and filtered, be washed to neutrality with second distillation, put into baking oven dry, then with redistilled water, it be mixed with the aqueous solution that concentration is 10mg/mL..
6. the preparation method of a kind of high sensitivity glucose biological sensor according to claim 2, is characterized in that, phosphate buffered solution is every 0.2754～2.1202g Na
2HPO
412H
2O adds 0.0517～0.8553g NaH
2PO
42H
2O constant volume in the volumetric flask of 250mL makes.
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| CN104630869A (en) * | 2015-01-22 | 2015-05-20 | 江南大学 | DNA sensor for detecting staphylococcus aureus as well as preparation method and application of DNA sensor |
| CN105301086A (en) * | 2015-12-05 | 2016-02-03 | 桂林理工大学 | Preparation method and application of glucose oxidase biosensor |
| CN105606674A (en) * | 2015-12-22 | 2016-05-25 | 张利琴 | Modified gold electrode and preparation method thereof |
| CN107782777A (en) * | 2017-08-31 | 2018-03-09 | 华南师范大学 | A kind of either high redox activity bovine serum albumin(BSA) carbon nano-tube combination electrode and its preparation method and application |
| CN108918448A (en) * | 2018-06-28 | 2018-11-30 | 河南省肿瘤医院 | A kind of preparation method based on the enhanced enzyme biological sensing material of nanogold |
| CN109813777A (en) * | 2018-11-30 | 2019-05-28 | 合肥天一生物技术研究所有限责任公司 | A kind of three electrode sensor detection devices |
| CN110023745A (en) * | 2016-12-09 | 2019-07-16 | 东北大学 | The durable biosensor and droplet deposition fixing means based on enzyme |
| CN114252487A (en) * | 2020-09-24 | 2022-03-29 | 中国科学院理化技术研究所 | Enzyme electrode, electrochemical biosensor and method for analyzing phenol concentration in water |
| WO2022148114A1 (en) * | 2021-01-08 | 2022-07-14 | 中山大学 | Sensor for detecting plant active small molecules and manufacturing method |
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2013
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| CN104630869A (en) * | 2015-01-22 | 2015-05-20 | 江南大学 | DNA sensor for detecting staphylococcus aureus as well as preparation method and application of DNA sensor |
| CN104630869B (en) * | 2015-01-22 | 2017-07-14 | 江南大学 | A kind of DNA sensor for detecting staphylococcus aureus and its preparation and application |
| CN105301086A (en) * | 2015-12-05 | 2016-02-03 | 桂林理工大学 | Preparation method and application of glucose oxidase biosensor |
| CN105606674A (en) * | 2015-12-22 | 2016-05-25 | 张利琴 | Modified gold electrode and preparation method thereof |
| CN110023745A (en) * | 2016-12-09 | 2019-07-16 | 东北大学 | The durable biosensor and droplet deposition fixing means based on enzyme |
| CN110023745B (en) * | 2016-12-09 | 2022-08-23 | 东北大学 | Robust enzyme-based biosensor and droplet deposition immobilization method |
| CN107782777A (en) * | 2017-08-31 | 2018-03-09 | 华南师范大学 | A kind of either high redox activity bovine serum albumin(BSA) carbon nano-tube combination electrode and its preparation method and application |
| CN108918448A (en) * | 2018-06-28 | 2018-11-30 | 河南省肿瘤医院 | A kind of preparation method based on the enhanced enzyme biological sensing material of nanogold |
| CN108918448B (en) * | 2018-06-28 | 2020-10-02 | 河南省肿瘤医院 | Preparation method of nano-gold-based enhanced enzyme biosensing material |
| CN109813777A (en) * | 2018-11-30 | 2019-05-28 | 合肥天一生物技术研究所有限责任公司 | A kind of three electrode sensor detection devices |
| CN114252487A (en) * | 2020-09-24 | 2022-03-29 | 中国科学院理化技术研究所 | Enzyme electrode, electrochemical biosensor and method for analyzing phenol concentration in water |
| WO2022148114A1 (en) * | 2021-01-08 | 2022-07-14 | 中山大学 | Sensor for detecting plant active small molecules and manufacturing method |
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Application publication date: 20130626 |