CN104155453A - Hyaluronic acid modified surface plasma resonance spectrometer chip and preparation method thereof - Google Patents
Hyaluronic acid modified surface plasma resonance spectrometer chip and preparation method thereof Download PDFInfo
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Abstract
The invention relates to a hyaluronic acid modified surface plasma resonance spectrometer chip and a preparation method thereof. The structure of the hyaluronic acid modified chip is orderly composed of a glass layer, a chromium layer, a gold film layer, a mercapto-alcohol monomolecular layer and a hyaluronic acid layer. The surface of the gold film is modified by use of mercaptoundecanol and then a self-assembly single layer can be formed; next, the self-assembly single layer is epoxidized by use of epoxy chloropropane and then immersed into a hyaluronic acid solution, covalently modified with a layer of hyaluronic acid and further subjected to carboxylation by use of bromoacetic acid, and finally, the hyaluronic acid-based surface plasma resonance spectrometer chip can be obtained. The chip has excellent antifouling property in a single protein, a natural complex sample and 10% blood serum, and has high immobilization capacity and excellent compatibility for biomacromolecular antibodies, and high-specificity sensitive quick detection on target molecules in a complex protein system is realized. The chip has excellent antifouling property, and is low in raw material cost; the preparation method of the chip is easy to operate; the chip has excellent economic feasibility and practicability.
Description
Technical field
The present invention relates to a kind of surface plasma resonance instrument chip based on hyaluronic acid decorated and preparation method thereof, belong to design and the preparation method of surface plasma resonance spectrometer antipollution chip.
Background technology
Surface plasma resonance (surface plasmon resonance, being called for short SPR) spectrometer has the advantages such as easy, quick, highly sensitive because of it, by abroad large-scale instrument company is generally good, and start to research and develop on a large scale, develop into powerful qualitative or quantitative measurment interaction of molecules, be subject to numerous scientific research personnel, large-scale medicine enterprises pay attention and attention, be widely used in the numerous areas such as biotechnology, medical detection, environmental science, food security, drug screening, material analysis.
SPR chip (the CM5 series of AM General company as more in current application, on naked golden film, connect last layer glucosan) be the surface plasma resonance spectrometer assembly of core the most, the essential physical condition that produces spr signal is provided, mainly comprises coupled apparatus, metal film and surface matrix etc.On SPR chip, non-specific adsorption is the ubiquity problem that SPR analyzes, and this is to be determined by the chemical property of chip surface, structure, electronegativity and water wettability.Do not do the naked golden chip of any modification, because surface is extremely hydrophobic, if directly apply to detection, can adsorb the non-thing to be detected of last layer.More common glucan-modified SPR chip at present, is exactly to modify one deck glucosan in naked gold surface, makes chip obtain good water wettability, the aquation absorption of inhibition of impurities albumen to a certain extent that hydrogen bond produces.But this chip only has good anti-absorption property for single protein solution, for more complicated system, as soya-bean milk, milk etc. can not meet the demands substantially.Due to the monopolization of offshore company, glucosan family chip is expensive on the other hand.Therefore, research and development have the SPR chip of antifouling property, reduce surperficial non-specific adsorption, improve detection accuracy and degree of accuracy and become one of experts and scholars' problem demanding prompt solution.
Summary of the invention
The object of the invention is to provide a kind of surface plasma resonance instrument chip based on hyaluronic acid decorated and preparation method thereof.Hyaluronic acid layer, because having better water wettability, produces stronger water affinity, therefore has the performance of good anti-nonspecific proteins absorption, especially detect for actual sample, and as soya-bean milk, the complicated solution systems such as the serum of milk and dilution.And this chip preparation cost is low, procedure is simple.The present invention is realized by the following technical programs.
One of the present invention is based on hyaluronic surface plasma resonance instrument chip; The structure of its hyaluronic acid decorated chip is followed successively by glassy layer, chromium layer, golden membranous layer, mercaptoalcohol unimolecular layer and hyaluronic acid layer composition.
Described BK7 glassy layer thickness is preferably 0.3-0.7 millimeter.Described chromium layer thickness is preferably 2-3 nanometer.Described golden membranous layer thickness is preferably 45-50 nanometer.Described mercaptoalcohol layer is unimolecular layer.Described hyaluronic acid layer thickness is preferably 6-15 nanometer.
Of the present invention based on hyaluronic surface plasma resonance instrument chip preparation method, comprise the following steps:
A) naked golden chip preparation
In BK7 substrate of glass, first apply 2-3nm thick chromium layer by vacuum sputtering, then apply 45-50nm thick gold membrane, obtained naked golden chip;
B) naked golden chip pre-service
The naked golden chip that step a) is obtained immerses in the mixed solution of the concentrated sulphuric acid and hydrogen peroxide volume ratio 1:0.4-1:1, under normal temperature, soaks 1-6h; Then take out by washed with de-ionized water until surface, without sulfuric acid and hydrogen peroxide residue, then dries up with nitrogen;
C) mercaptoalcohol is modified
11-sulfydryl-1-undecyl alcohol the solution that is 5-10mM with absolute ethyl alcohol compound concentration; The naked golden chip that step b) is obtained immerses in above-mentioned 11-sulfydryl-1-undecyl alcohol solution, takes out after soaking 6-15h under normal temperature, has formed mercaptoalcohol self-assembled monolayer on golden film surface; , then dry up with nitrogen until be not attached to golden film surface mercaptoalcohol and be cleaned totally by ethanol and washed with de-ionized water;
D) hyaluronic acid decorated
1) the epichlorokydrin solution that is 0.6M with diethylene glycol dimethyl ether compound concentration; The chip that step c) is obtained immerses in above-mentioned epichlorokydrin solution, takes out after soaking 2-8h under normal temperature; Wash residual epichlorokydrin and diethylene glycol dimethyl ether with deionized water, then and dry up with nitrogen;
2) be the hyaluronic acid solution that 1-10mg/mL, molecular weight are 10-2000kDa with the sodium hydroxide solution compound concentration of 0.1M; By step 1) chip that obtains immerses in above-mentioned hyaluronic acid solution, takes out after soaking 5-24h under normal temperature; Wash unreacted hyaluronic acid off with deionized water, and dry up for subsequent use with nitrogen;
E) carboxylated modification
The bromoacetic acid solution that is 1M with the sodium hydroxide solution compound concentration of 1M; By steps d) chip that obtains immerses in above-mentioned bromoacetic acid solution, under normal temperature, soaks 8-24h, in self-assembled monolayer finishing layer of transparent matter acid layer.Dry up by washed with de-ionized water and with nitrogen.
Described golden silverskin, silver/golden composite membrane replacement for film.Described hyaluronan molecule amount is 10-2000kDa, and concentration is 1-10mg/mL.But do not limit to its molecule type and source.
Hyaluronic acid decorated naked golden chip prepared by method of the present invention, and there is good anti-protein adsorption performance, up to the present be that nobody reported, and we have also carried out the bovine serum albumin(BSA) in practical application-detection soya-bean milk to it, verify that this chip has good non-specific recognition capability.
Beneficial effect of the present invention:
1) the present invention's development has good antifouling property based on hyaluronic acid SPR chip, and in lysozyme, bovine serum albumin, soya-bean milk, milk and orange juice, non-Characteristic Adsorption amount is respectively 4.6ng/cm
2, 7.7ng/cm
2, 0.6ng/cm
2, 9.8ng/cm
2and 16.1ng/cm
2, see accompanying drawing 2.Simultaneously, connecting after biological identification molecule (bovine serum albumin(BSA) antibody), there is not obvious variation in the antifouling property of this chip, in lysozyme, soya-bean milk, milk, 10% serum and 100% serum, non-Characteristic Adsorption amount is respectively 0.67ng/cm
2, 2.5ng/cm
2, 17ng/cm
2, 16ng/cm
2and 60ng/cm
2, see accompanying drawing 3.
2) the present invention development has high stability based on hyaluronic acid SPR chip, under drying regime, store 4 months or pH7.4 phosphate buffer in store after 7 days, antifouling property is unchanged.
3) the present invention's development has high supported quantity and biocompatibility based on hyaluronic acid SPR chip, and taking bovine serum albumin antibody (anti-BSA) as example, supported quantity reaches 780ng/cm
2; This sensing chip has high specific, and taking 15nM bovine serum albumin as object, taking lysozyme and soya-bean milk as reference protein, signal to noise ratio (S/N ratio) has reached respectively 94.6 and 25.8, sees accompanying drawing 4.
4) the present invention development based on hyaluronic acid SPR chip on fix bovine serum albumin antibody, within the scope of 15-700nM, realized the quantitative detection of bovine serum albumin, see accompanying drawing 5.
Brief description of the drawings
The SPR chip of Fig. 1 based on hyaluronic acid decorated; Wherein, at the bottom of 1-glass chip, 2-chromium layer, 3-golden membranous layer, 4-mercaptoalcohol unimolecular layer, 5-hyaluronic acid layer.
Fig. 2 hyaluronic acid-based chip is to the non-specific adsorption amount in lysozyme (1mg/mL), bovine serum albumin (1mg/mL), soya-bean milk (10mg/mL), milk (30mg/mL) and orange juice (10mg/mL) solution.
The non-specific adsorption amount of the hyaluronic acid-based SPR chip of the immobilized bovine serum albumin antibody of Fig. 3 in lysozyme (1mg/mL), soya-bean milk (10mg/mL), milk (30mg/mL), 10% serum and 100% serum.
The testing result of the hyaluronic acid-based SPR chip of the immobilized bovine serum albumin antibody of Fig. 4 in single albumen and compound protein system.Wherein, lysozyme 1mg/mL; Soya-bean milk 10mg/mL; Bovine serum albumin 15nM; Bovine serum albumin 15nM+ lysozyme 1mg/mL; Bovine serum albumin 15nM+ soya-bean milk 10mg/mL.
The hyaluronic acid-based SPR chip of the immobilized bovine serum albumin antibody of Fig. 5 quantitatively detects the typical curve of bovine serum albumin.
Fig. 6 the present invention prepares the schematic flow sheet of the surface plasma resonance instrument chip based on hyaluronic acid decorated.
Embodiment
Embodiment 1
In BK7 substrate of glass, first apply one deck 2nm thick chromium layer by vacuum sputtering, then apply one deck 48nm thick gold membrane or electrum (blending ratio arbitrarily), obtained naked golden chip.Naked golden chip is immersed in the concentrated sulphuric acid and hydrogen peroxide (volume ratio 1:0.4) mixed solution, under normal temperature, soak 3h.Then take out and dry up with nitrogen again by washed with de-ionized water.Dried naked golden chip is immersed in 11-sulfydryl-1-undecyl alcohol solution (ethanol preparation) of 5mM, under normal temperature, soak 12h.After ethanol, washed with de-ionized water and nitrogen drying, immerse in the epichlorokydrin solution (diethylene glycol dimethyl ether preparation) of 0.6M, under normal temperature, soak 4h.Drying up rear immersion concentration with washed with de-ionized water and nitrogen is in 1mg/mL, molecular weight 10kDa hyaluronic acid solution (preparation of 0.1M sodium hydroxide solution), under normal temperature, soaks 16h.Dry up by washed with de-ionized water and with nitrogen.Then immerse in the bromoacetic acid solution (preparation of 1M sodium hydroxide solution) of 1M, under normal temperature, soak 12h.Dry up by washed with de-ionized water and with nitrogen.Obtain as shown in Figure 6 based on hyaluronic acid bio-sensing chip, wherein mercaptoalcohol layer is unimolecular layer, hyaluronic acid layer 6-10 nanometer.
Embodiment 2
In BK7 substrate of glass, first apply one deck 2nm thick chromium layer by vacuum sputtering, then apply one deck 48nm thick gold membrane or electrum (blending ratio arbitrarily), obtained naked golden chip.Naked golden chip is immersed in the concentrated sulphuric acid and hydrogen peroxide (volume ratio 1:0.6) mixed solution, under normal temperature, soak 3h.Then take out and dry up with nitrogen again by washed with de-ionized water.Dried naked golden chip is immersed in 11-sulfydryl-1-undecyl alcohol solution (ethanol preparation) of 5mM, under normal temperature, soak 12h.After ethanol, washed with de-ionized water and nitrogen drying, immerse in the epichlorokydrin solution (diethylene glycol dimethyl ether preparation) of 0.6M, under normal temperature, soak 4h.Drying up rear immersion concentration with washed with de-ionized water and nitrogen is in 3mg/mL, molecular weight 1000kDa hyaluronic acid solution (preparation of 0.1M sodium hydroxide solution), under normal temperature, soaks 16h.Dry up by washed with de-ionized water and with nitrogen.Then immerse in the bromoacetic acid solution (preparation of 1M sodium hydroxide solution) of 1M, under normal temperature, soak 12h.Dry up by washed with de-ionized water and with nitrogen.Obtain as shown in Figure 1 based on hyaluronic acid bio-sensing chip, wherein mercaptoalcohol layer is unimolecular layer, hyaluronic acid layer 8-12 nanometer.
Embodiment 3
In BK7 substrate of glass, first apply one deck 2nm thick chromium layer by vacuum sputtering, then apply one deck 48nm thick gold membrane or electrum (blending ratio arbitrarily), obtained naked golden chip.Naked golden chip is immersed in the concentrated sulphuric acid and hydrogen peroxide (volume ratio 1:1) mixed solution, under normal temperature, soak 3h.Then take out and dry up with nitrogen again by washed with de-ionized water.Dried naked golden chip is immersed in 11-sulfydryl-1-undecyl alcohol solution (ethanol preparation) of 5mM, under normal temperature, soak 12h.After ethanol, washed with de-ionized water and nitrogen drying, immerse in the epichlorokydrin solution (diethylene glycol dimethyl ether preparation) of 0.6M, under normal temperature, soak 4h.Drying up rear immersion concentration with washed with de-ionized water and nitrogen is in 10mg/mL, molecular weight 2000kDa hyaluronic acid solution (preparation of 0.1M sodium hydroxide solution), under normal temperature, soaks 16h.Dry up by washed with de-ionized water and with nitrogen.Then immerse in the bromoacetic acid solution (preparation of 1M sodium hydroxide solution) of 1M, under normal temperature, soak 12h.Dry up by washed with de-ionized water and with nitrogen.Obtain as shown in Figure 1 based on hyaluronic acid bio-sensing chip, wherein mercaptoalcohol layer is unimolecular layer, hyaluronic acid layer 10-15 nanometer.
Embodiment 4
The hyaluronic acid-based SPR chip pitch that embodiment 2 is obtained fits on the prism of SPR system.Phosphate buffer taking pH as 7.3 is as mobile phase, and flow velocity is 10 μ L/min.After baseline is steady, toward the bovine serum albumin solution that injects 100 μ L1mg/mL in quantitative ring, promote protein solution through mobile phase and arrive chip surface, by SPR system measurement resonance angle real-time change curve, after 20min, read SPR resonance angle changing value, and to calculate non-specific adsorption amount be 8.0ng/cm
2.
Embodiment 5
The hyaluronic acid-based SPR chip pitch that embodiment 2 is obtained fits on the prism of SPR system.Phosphate buffer taking pH as 7.3 is as mobile phase, and flow velocity is 10 μ L/min.After baseline is steady, toward quantitatively injecting 100 μ L lysozymes (1mg/mL) or bovine serum albumin (1mg/mL) or soya-bean milk (10mg/mL) or milk (30mg/mL) or orange juice (10mg/mL) solution in ring, promote protein solution through mobile phase and arrive chip surface, by SPR system measurement resonance angle real-time change curve, after 20min, read SPR resonance angle changing value, and calculate non-specific adsorption amount and be respectively 4.6ng/cm
2, 7.7ng/cm
2, 0.6ng/cm
2, 9.8ng/cm
2and 16.1ng/cm
2.
Embodiment 6
The hyaluronic acid-based SPR chip pitch that embodiment 2 is obtained fits on the prism of SPR system.Phosphate buffer taking pH as 7.3 is as mobile phase, and flow velocity is 10 μ L/min.After baseline is steady, in in quantitative ring, inject 100 μ L1-ethyl-3-(3-dimethylaminopropyl) phosphinylidyne diimine (EDC, concentration is 0.4M) and N-hydroxy thiosuccinimide (NHSS, concentration is 0.1M) mixed solution, promote EDC/NHSS solution through mobile phase and arrive chip surface.After 15min, inject 100 μ L bovine serum albumin antibody (anti-BSA, 1mg/mL), promote anti-BSA solution through mobile phase and arrive chip surface, after monoethanolamine sealing, after 30min, obtain the SPR sensing chip of immobilized anti-BSA.
The hyaluronic acid-based SPR chip of above-mentioned acquisition is fitted on the prism of SPR system with pitch.Phosphate buffer taking pH as 7.3 is as mobile phase, and flow velocity is 10 μ L/min.After baseline is steady, toward quantitatively injecting 100 μ L lysozymes (1mg/mL) or soya-bean milk (10mg/mL) or milk (30mg/mL) or 10% serum or 100% serum in ring, promote protein solution through mobile phase and arrive chip surface, by SPR system measurement resonance angle real-time change curve, after 20min, read SPR resonance angle changing value, and calculate non-specific adsorption amount and be respectively 0.67ng/cm
2, 2.5ng/cm
2, 17ng/cm
2, 16ng/cm
2and 60ng/cm
2.
Embodiment 7
The hyaluronic acid-based SPR chip pitch that embodiment 1 is obtained fits on the prism of SPR system.Phosphate buffer taking pH as 7.3 is as mobile phase, and flow velocity is 10mL/min.After baseline is steady, in in quantitative ring, inject 100 μ L1-ethyl-3-(3-dimethylaminopropyl) phosphinylidyne diimine (EDC, concentration is 0.4M) and N-hydroxy thiosuccinimide (NHSS, concentration is 0.1M) mixed solution, promote EDC/NHSS solution through mobile phase and arrive chip surface.After 15min, inject 100 μ L bovine serum albumin antibody (anti-BSA, 1mg/mL), promote anti-BSA solution through mobile phase and arrive chip surface, after monoethanolamine sealing, after 30min, obtain the SPR sensing chip of immobilized anti-BSA, inject respectively 100 μ L lysozymes (1mg/mL), soya-bean milk (10mg/mL), bovine serum albumin (the 15nM of variable concentrations, 75nM, 150nM, 300nM, 450nM and 700nM), bovine serum albumin+lysozyme (15nM, 1mg/mL), bovine serum albumin+soya-bean milk (15nM, 10mg/mL), by the BSA solution of SPR system log (SYSLOG) resonance angle real-time change, recording resonance angle changes, obtain BSA content and examination criteria curve.
The present invention is based on hyaluronic acid decorated surface plasma resonance instrument chip and preparation method thereof.The structure of hyaluronic acid decorated chip is followed successively by glassy layer, chromium layer, golden membranous layer, mercaptoalcohol unimolecular layer and hyaluronic acid layer composition.On golden film surface, modify with sulfydryl undecyl alcohol, form self-assembled monolayer.Then after epichlorokydrin epoxidation, immerse in hyaluronic acid solution, the acid of covalent modification layer of transparent matter, and then it is carboxylated to adopt bromoacetic acid to carry out, and obtains a kind of based on hyaluronic surface plasma resonance instrument chip.Chip of the present invention is at single albumen (bovine serum albumin, lysozyme), in natural complex sample (milk, soya-bean milk, orange juice) and 10% serum, all there is good antifouling property, and biomacromolecule antibody is had to high supported quantity and good compatibility, can realize high specific, the sensitive fast detecting of target molecule in complicated albumen system (lysozyme, soya-bean milk).Chip of the present invention has the advantages such as good antifouling property, high stability and high supported quantity, and raw materials cost is low, preparation method's easy operating, has good economic feasibility and practicality.
Claims (9)
1. one kind based on hyaluronic surface plasma resonance instrument chip; The structure that it is characterized in that hyaluronic acid decorated chip is followed successively by glassy layer, chromium layer, golden membranous layer, mercaptoalcohol unimolecular layer and hyaluronic acid layer composition.
2. resonance instrument chip as claimed in claim 1; It is characterized in that described BK7 glassy layer thickness is 0.3-0.7 millimeter.
3. resonance instrument chip as claimed in claim 1; It is characterized in that described chromium layer thickness is 2-3 nanometer.
4. resonance instrument chip as claimed in claim 1; It is characterized in that described golden membranous layer thickness is 45-50 nanometer.
5. resonance instrument chip as claimed in claim 1; It is characterized in that described mercaptoalcohol layer is unimolecular layer.
6. resonance instrument chip as claimed in claim 1; It is characterized in that described hyaluronic acid layer thickness is 6-15 nanometer.
Claim 1 based on hyaluronic surface plasma resonance instrument chip preparation method, it is characterized in that comprising the following steps:
A) naked golden chip preparation
In BK7 substrate of glass, first apply 2-3nm thick chromium layer by vacuum sputtering, then apply 45-50nm thick gold membrane, obtained naked golden chip;
B) naked golden chip pre-service
The naked golden chip that step a) is obtained immerses in the mixed solution of the concentrated sulphuric acid and hydrogen peroxide volume ratio 1:0.4-1:1, under normal temperature, soaks 1-6h; Then take out by washed with de-ionized water until surface, without sulfuric acid and hydrogen peroxide residue, then dries up with nitrogen;
C) mercaptoalcohol is modified
11-sulfydryl-1-undecyl alcohol the solution that is 5-10mM with absolute ethyl alcohol compound concentration; The naked golden chip that step b) is obtained immerses in above-mentioned 11-sulfydryl-1-undecyl alcohol solution, takes out after soaking 6-15h under normal temperature, has formed mercaptoalcohol self-assembled monolayer on golden film surface; , then dry up with nitrogen until be not attached to golden film surface mercaptoalcohol and be cleaned totally by ethanol and washed with de-ionized water;
D) hyaluronic acid decorated
1) the epichlorokydrin solution that is 0.6M with diethylene glycol dimethyl ether compound concentration; The chip that step c) is obtained immerses in above-mentioned epichlorokydrin solution, takes out after soaking 2-8h under normal temperature; Wash residual epichlorokydrin and diethylene glycol dimethyl ether with deionized water, then and dry up with nitrogen;
2) be the hyaluronic acid solution that 1-10mg/mL, molecular weight are 10-2000kDa with the sodium hydroxide solution compound concentration of 0.1M; By step 1) chip that obtains immerses in above-mentioned hyaluronic acid solution, takes out after soaking 5-24h under normal temperature; Wash unreacted hyaluronic acid off with deionized water, and dry up for subsequent use with nitrogen;
E) carboxylated modification
The bromoacetic acid solution that is 1M with the sodium hydroxide solution compound concentration of 1M; By steps d) chip that obtains immerses in above-mentioned bromoacetic acid solution, under normal temperature, soaks 8-24h, in self-assembled monolayer finishing layer of transparent matter acid layer.Dry up by washed with de-ionized water and with nitrogen.
8. method as claimed in claim 7, is characterized in that described golden silverskin, silver/golden composite membrane replacement for film.
9. method as claimed in claim 7, is characterized in that described hyaluronan molecule amount is 10-2000kDa, and concentration is 1-10mg/mL.
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| CN104691032A (en) * | 2015-03-10 | 2015-06-10 | 中国石油大学(华东) | Hyaluronic acid film and application thereof |
| CN104865225A (en) * | 2015-05-14 | 2015-08-26 | 北京化工大学 | Method for detecting protein content of small rubber particles in rubber plants and method for screening rubber plant lines by using method |
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| CN105403540A (en) * | 2015-12-04 | 2016-03-16 | 天津大学 | Surface plasmon resonance instrument chip based on zwitterion heptapeptide modification and preparation method thereof |
| CN105548085A (en) * | 2015-12-04 | 2016-05-04 | 天津大学 | Preparation method of surface plasma resonance instrument chip based on amphiphilic heptapeptide modification |
| CN105738451A (en) * | 2016-02-01 | 2016-07-06 | 大连理工大学 | Direct electron transfer type glucose biosensor and preparation method and application |
| CN105954237A (en) * | 2016-04-26 | 2016-09-21 | 天津大学 | Surface plasma resonance instrument chip and preparation method thereof |
| CN106018347A (en) * | 2016-05-06 | 2016-10-12 | 中国科学院电子学研究所 | Surface plasma resonance sensing chip and preparation method and application thereof |
| CN106018347B (en) * | 2016-05-06 | 2019-06-18 | 中国科学院电子学研究所 | A kind of surface plasmon resonance sensing chip and its preparation method and application |
| CN106896087A (en) * | 2017-03-31 | 2017-06-27 | 丁利 | The preparation method of the surface plasma resonance instrument chip based on hyperbranched amphion polymethyl base cysteine modified |
| CN107064072A (en) * | 2017-03-31 | 2017-08-18 | 丁利 | The preparation method of surface plasma resonance instrument chip based on amphion polymethyl base cysteine modified |
| CN106896087B (en) * | 2017-03-31 | 2019-04-23 | 丁利 | The preparation method of surface plasma resonance instrument chip based on hyperbranched amphoteric ion polymethyl base cysteine modified |
| CN107064072B (en) * | 2017-03-31 | 2019-04-26 | 丁利 | The preparation method of surface plasma resonance instrument chip based on amphoteric ion polymethyl base cysteine modified |
| WO2021185091A1 (en) * | 2020-03-19 | 2021-09-23 | 京东方科技集团股份有限公司 | Detection chip and modification method therefor |
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