CN100427941C - Chiral sensor based on ox seralbumin and preparing process thereof - Google Patents
Chiral sensor based on ox seralbumin and preparing process thereof Download PDFInfo
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- CN100427941C CN100427941C CNB2006100254889A CN200610025488A CN100427941C CN 100427941 C CN100427941 C CN 100427941C CN B2006100254889 A CNB2006100254889 A CN B2006100254889A CN 200610025488 A CN200610025488 A CN 200610025488A CN 100427941 C CN100427941 C CN 100427941C
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Abstract
The present invention relates to the research fields of nanometer technology, biotechnology and electrochemistry. More specifically, the present invention provides a bovine serum albumin based chiral sensor and a preparing method thereof. Different chiral isomers are obviously different from each other in the aspects of bioactivity in organisms, pharmacological action, the metabolism course, etc.; consequently, the development of chiral identification methods with the advantages of simplicity, accuracy and high speed become the main direction of chiral analysis in recent years. The present invention provides a bovine serum albumin based chiral sensor. Bovine serum albumin (BSA) is used as a chiral selecting agent in the chiral sensor for identifying isomer samples marked by metal nanometer particles, and chiral identification is realized in an electrochemical detection approach. The chiral sensor of the present invention can be highly efficiently applied to the detection of chiral amino acid and chiral drugs; experiments indicate that the chiral sensor can detect amino acid isomers with the concentration of 0.1 picomole.
Description
Technical field
The present invention relates to nanometer technology, biotechnology and electrochemical research field, particularly, the invention provides a kind of chiral sensor based on bovine serum albumin(BSA) (BSA) with and preparation method thereof.
Background technology
Chipal compounds and life process are closely bound up, different chiral isomers biologically active in vivo, pharmacological action, metabolic processes etc. have tangible difference, therefore development is simple, and accurately, the chiral Recognition method becomes the main direction of chiral analysis in recent years fast.Recent years, the research of chiral sensor has obtained certain development, chiral selector major part wherein is the chiral stationary phase (A.Tsourkas that uses for reference on the chromatogram, O.Hofstetter, H.Hofstetter, R.Weissleder, L.Josephson, Angew.Chem.Int.Edit.2004,43,2395).Albumen is owing to have complicated and reversible conformation, separating chiral isomeride well on chromatogram, and domestic existing patent (number of patent application: 99113091.X, publication number: CN 1280986A) report utilizes albumen to make the chromatogram chiral stationary phase.For example BSA is used to separating chiral amino acid and chiral drug usually on chromatogram, separating effect is fine, and experiment and structure analysis prove that the chiral selectivity of BSA is mainly derived from its stereoselectivity between chipal compounds (host-guest), hydrogen bond action and hydrophilic and hydrophobic (M.Kato, K.Sakai-Kato, N.Matsumoto, T.Toyo ' oka, Anal.Chem.2002,74,1915; C.V.Kumar, A.Buranaprapuk, H.C.Sze, Chem.Comm.2001,3,297), yet up to the present, the BSA chiral Recognition of on chiral sensor, carrying out also of no use.Therefore, the advantage that can simply, fast and accurately measure analyte with good chiral selectivity of BSA and sensor is integrated as point of penetration, will have important theory and practical study meaning to the development of chiral sensor.
On the other hand, nano material is considered to the focus in cross-centennial investigation of materials field.The quantum size effect of nano material itself, small-size effect and surface effect etc. make it have many distinctive character, therefore are widely used at aspects such as catalysis, biological medicine and new materials.Synthetic (the P.Selvakannan of the aqueous metal nano particle of bibliographical information wherein, S.Mandal, S.Phadtare, A.Gole, R.Pasricha, S.D.Adyanthaya, M.Sastry, J.Colloid.Interf.Sci.2004,269,97), opened up wide prospect in the application (biological example mark and drug conveying) of biological field for nano material.For the chiral sensor of albumen as chiral selector, metal nanoparticle can be used for mark chiral amino acid isomeride, thereby detect the chiral Recognition result by the Electrochemical Detection metal nanoparticle.
Summary of the invention
The purpose of this invention is to provide a kind of chiral sensor, make chiral Recognition easy and simple to handle, the detection sensitivity height based on BSA.
Another object of the present invention provides the preparation method of the sensor.
The invention provides a kind ofly based on the bovine serum albumin(BSA) chiral sensor, electrode surface covers the alumina sol-gel mould contain bovine serum albumin(BSA) in this sensor, and the thickness range of film is 20～40nm.
Experimental result shows that this sensor is chiral Recognition effectively, and can detect amino acid isomeride and medicine isomeride delicately.
In the sensor of the present invention, electrode can be screen printing electrode or glass-carbon electrode etc.
The present invention also provides the preparation method of the sensor, and being about to concentration is 0.05-0.2mg mL
-1Bovine serum albumin(BSA) and alumina sol-gel mix, the volume ratio of bovine serum albumin(BSA) and alumina sol-gel is 0.5: 1-1.2: 1; Mixed solution is covered on the electrode, and 0-4 ℃ leaves standstill curing 60-80 hour, and the film thickness scope that obtains is 20～40nm; At last the above-mentioned electrode that makes is connected with electrochemical appliance, makes sensor.
In the sensor preparation process of the present invention, mixed solution covers on the electrode by dipping, coating or dropping method.Covering a used mixed solution cumulative volume of electrode can be 2-20 μ L.
In the sensor preparation process of the present invention, the concentration of used bovine serum albumin(BSA) is 0.09-0.15mg mL
-1The time, the result more optimizes.
In the sensor preparation process of the present invention, used electrode can be screen printing electrode or glass-carbon electrode etc.
Sensor of the present invention is in preparation process, and used sensor glass-carbon electrode is shaft-like, and its diameter can be the 2-4 millimeter.
This sensor mainly be by alumina sol-gel under cryogenic conditions fixedly BSA prepare sensor, the preparation method is simple, it is good that protein active keeps.During chiral Recognition, only need the amino acid isomeride solution of this sensor and metal nanoparticle mark was hatched respectively 8-12 minute, then obtain the chiral Recognition result by Electrochemical Detection, simple to operate, save time, and have higher detection sensitivity.
During sensor application of the present invention, two of the desirable above-mentioned sensors that obtains, phosphate buffer solution hatching 8-12 minute that places the chiral isomer testing sample that contains the metal nanoparticle mark respectively, the pH scope of phosphate buffer solution is 6-9; After the hatching, fully wash electrode with distilled water and carry out electrochemical gaging then and get final product.
In the sensor application process of the present invention, adopting metal nanoparticle can be gold grain, elargol particle or nano copper sulfate particle etc.
In the sensor application process of the present invention, adopting the testing sample isomeride is tryptophane isomeride, isomers of phenylalanine or tyrosine isomeride, also can be chiral drug etc.
Above-mentioned metal nanoparticle can be a gold size, behind gold label silver stain, comes the oxidation signal of Electrochemical Detection silver; Also can be elargol and Ag@Au or Cu@Au alloy nanoparticle etc., directly detect metal nanoparticle.The object of chiral Recognition can be the tryptophane isomeride, also can be phenylalanine, tyrosine and some chiral drugs.
In the sensor application process of the present invention, adopt three-electrode system to carry out electrochemical gaging, platinum filament is to electrode, and saturated calomel electrode is a contrast electrode, and sensor electrode after the chiral Recognition or carbon fiber electrically be working electrode very, at 0.08-0.12mol L
-1Acetate type buffer solution (pH 4.8-5.5) or 0.08-0.12mol L
-1In the liquid, write down the differential pulse voltammetry curve at the bottom of the nitric acid.
The invention provides a kind of chiral sensor based on bovine serum albumin(BSA).This chiral sensor preparation is simple, the activity of ankyrin stably, and maintenance albumen, and also detection sensitivity is than higher.Chiral sensor of the present invention can be applied to detect and separating chiral amino acid and chiral drug efficiently, and experiment shows that this chiral sensor can detect the amino acid isomeride of 0.1 picomole concentration.
Description of drawings
Fig. 1 is a chiral Recognition process synoptic diagram.
Fig. 2 is the figure as a result of chirality tryptophane identification.On behalf of this sensor, curve a and b L-and D-tryptophane are carried out the result of chiral Recognition respectively.Definition isomery selectivity factor α discerns the ratio of the oxidation peak current of gained silver to L-and D-type amino acid for this sensor.Then this sensor is 2.3 to the isomery selectivity factor of tryptophane.Experimental result shows that this sensor reaches 0.1 picomole concentration to the detectability of tryptophane isomeride.
Fig. 3 is the peak current of this sensor and isomery selectivity factor with tryptophane isomeride concentration change figure as a result.
Embodiment
Come below by the tryptophane isomeride of this sensor identification gold size mark that the present invention is described further.
(1) preparation of gold size
HAuCl with 500mL 1mM
4Solution is heated to and boils, and adds the citric acid three sodium solution of 50mL 38.8mM again, continues ebuillition of heated 10min, stops heated and stirred again 15 minutes, promptly makes the gold size that diameter is about 13-15nm, with being placed on brown bottle 0-4 ℃ preservation behind the 0.22 μ m membrane filtration.
(2) preparation of the tryptophane isomeride of gold size mark
Respectively the tryptophane isomeride solution of 1mL0.01mM concentration is joined above the 9mL in the freshly prepd gold size solution room temperature 20-30 ℃ of assembling 48 hours.
(3) sensor preparation
With 0.1mg mL
-1BSA and alumina sol-gel mixed solution 5 μ L (1: 1v/v) drip on glass-carbon electrode (Φ=4), leave standstill at 0-4 ℃ and solidified 72 hours, the alumina sol of formation-gel mould thickness is 25 ± 3nm.
(4) chiral Recognition
Tryptophane isomeride solution with the gold size mark of 10 μ L steps (2) preparations joins in the 10mL phosphate buffer solution (pH:7) respectively, then two sensors are hatched 10 minutes respectively therein after, fully wash with distilled water.
(5) gold label silver stain
Place silver to dye solution (mixed solution of the citrate buffer solution solution (pH=3.8) of the liquor argenti nitratis ophthalmicus of 150 μ L 0.22% and 150 μ L, 1% p-dihydroxy-benzene) lucifuge reaction 8 minutes respectively two sensors after the chiral Recognition, after fully washing with distilled water, then at 2.5% Na
2S
2O
3Aqueous solution placed 3 minutes, fully wash with distilled water more at last.
(6) electrochemical gaging
Adopt three-electrode system, platinum filament is to electrode, and saturated calomel electrode is a contrast electrode, and the glass-carbon electrode after silver dyes is a working electrode, and the acetic acid of 0.1mol/L-sodium acetate buffer solution (pH 5.2) is end liquid, record differential pulse voltammetry (DPV) curve.Sweep limit: 0.1V-0.8V (vs SCE).Wherein contrast electrode is isolated itself and end liquid with two salt bridges, avoids the Cl that constantly discharges
-Form AgCl precipitation interference measurement with silver.
This chiral sensor carries out the chiral Recognition tryptophane according to above-mentioned embodiment, and the chiral Recognition process is shown in Figure 1, and the chiral Recognition result who obtains as shown in Figures 2 and 3.In Fig. 2, on behalf of this sensor, curve a and b L-and D-tryptophane are carried out the result of chiral Recognition respectively.Definition isomery selectivity factor α discerns the ratio of the oxidation peak current of gained silver to L-and D-type amino acid for this sensor.Then this sensor is 2.3 to the isomery selectivity factor of tryptophane.Experimental result shows that this sensor reaches 0.1 picomole concentration to the detectability of tryptophane isomeride.Fig. 3 represents this sensor with tryptophane isomeride concentration change, the situation of change of the peak current of its detection and isomery selectivity factor.
Come below by the isomers of phenylalanine of this sensor identification gold size mark that the present invention is described further.
(1) preparation of the phenylalanine of the preparation of gold size and gold size mark is with embodiment 1
(2) sensor preparation
With 0.1mg mL
-1BSA and alumina sol-gel mixed solution 10 μ L (1: 1v/v) drip that (on the Φ=2mm), leave standstill at 0-4 ℃ and to solidify 72 hours, the alumina sol of formation-gel mould thickness is 31 ± 2nm at glass-carbon electrode.
(3) chiral Recognition
Isomers of phenylalanine solution with the gold size mark of 10 μ L steps (1) preparations joins in the 10mL phosphate buffer solution (pH:7.4) respectively, then two sensors are hatched 11 minutes respectively therein after, fully wash with distilled water.
(4) gold label silver stain
Place silver to dye solution (mixed solution of the citrate buffer solution solution (pH=3.8) of the liquor argenti nitratis ophthalmicus of 150 μ L 0.22% and 150 μ L, 1% p-dihydroxy-benzene) lucifuge reaction 8.5 minutes respectively two sensors after the chiral Recognition, after fully washing with distilled water, then at 2.5%Na
2S
2O
3Aqueous solution placed 3 minutes, fully wash with distilled water more at last.
(5) electrochemical determination method is with embodiment 1
This chiral sensor carries out chiral Recognition with above-mentioned embodiment to isomers of phenylalanine, and the isomery selectivity factor that obtains is 1.3.
Come below by the tyrosine isomeride of this sensor identification gold size mark that the present invention is described further.
(1) preparation of the tyrosine of the preparation of the preparation gold size of gold size and gold size mark is with embodiment 1
(2) sensor preparation
With 0.1mg mL
-1BSA and alumina sol-gel mixed solution 15 μ L (1: 1v/v) drip on glass-carbon electrode (Φ=4), leave standstill at 0-4 ℃ and solidified 72 hours, the alumina sol of formation-gel mould thickness is 36 ± 2nm.
(3) chiral Recognition
Tyrosine isomeride solution with the gold size mark of 10 μ L steps (1) preparations joins in the 10mL phosphate buffer solution (pH:8) respectively, then two sensors are hatched 12 minutes respectively therein after, fully wash with distilled water.
(4) gold label silver stain
Place silver to dye solution (mixed solution of the citrate buffer solution solution (pH=3.8) of the liquor argenti nitratis ophthalmicus of 150 μ L 0.22% and 150 μ L, 1% p-dihydroxy-benzene) lucifuge reaction 9 minutes respectively two sensors after the chiral Recognition, after fully washing with distilled water, then at 2.5% Na
2S
2O
3Aqueous solution placed 3 minutes, fully wash with distilled water more at last.
(5) electrochemical determination method is with embodiment 1
This chiral sensor carries out chiral Recognition tyrosine according to above-mentioned embodiment, and the isomery selectivity factor that obtains is 1.36.
Come below by the tryptophane isomeride of this sensor identification elargol mark that the present invention is described further.
(1) preparation of elargol
At 10mL 10
-3Mol L
-1AgNO
3In the solution, slowly drip 10mL 3 * 10
-3Mol L
-1NaBH
4Be reflected to stir in the ice bath and carry out, after dripping, leave ice bath, the stirring that does not stop is increased to room temperature gradually until solution temperature, the light yellow colloid of the clear that obtains, then with this colloid dialysis purification 24h in semi-permeable diaphragm, the pale brown look elargol that obtains, the nanometer elargol that promptly will prepare, its footpath grain is distributed within the 20-25nm scope.
(2) preparation of the tryptophane isomeride of elargol mark
Respectively the tryptophane isomeride solution of 1mL0.01mM concentration is joined above the 9mL in the freshly prepd fulmargin room temperature 20-30 ℃ of assembling 48 hours.
(3) sensor preparation
With 0.1mg mL
-1BSA and alumina sol-gel mixed solution 5 μ L (1: 1v/v) drip on glass-carbon electrode (Φ=4), leave standstill at 0-4 ℃ and solidified 72 hours.
(4) chiral Recognition
Tryptophane isomeride solution with the elargol mark of 10 μ L steps (2) preparations joins in the 10mL0.01M phosphate buffer solution (pH:7) respectively, then two sensors are hatched 8 minutes respectively therein after, fully wash with distilled water.
(5) Yin oxidation dissolution
Two sensors finishing the chiral Recognition reaction are immersed the HNO of 150 μ L 50% respectively
3In the solution, vibration makes silver-colored oxidation dissolution, takes out sensor behind the 5min, and adds 0.8mL 10mM HNO
3-KNO
3Solution carries out Electrochemical Detection as supporting electrolyte in this solution
(6) electrochemical gaging
Adopt three-electrode system, platinum filament is to electrode, and saturated calomel electrode is a contrast electrode, and 5 μ m carbon fiber microelectrodes with micro pipette tips are working electrode, in above-mentioned solution, adopts Anodic Stripping Voltammetry Determination Ag
+Electrode under-0.5V behind the preenrichment 150s, 0.0～+ the 0.6V scope in oppositely stripping, record stripping DPV signal.Wherein contrast electrode is isolated itself and end liquid with two salt bridges, avoids the Cl that constantly discharges
-Form AgCl precipitation interference measurement with silver.
Come below by the isomers of phenylalanine of this sensor identification elargol mark that the present invention is described further.
(1) preparation of the isomers of phenylalanine of the preparation of elargol and elargol mark is with embodiment 1
(2) sensor preparation
With 0.1mg mL
-1BSA and alumina sol-gel mixed solution 10 μ L (1: 1v/v) drip on glass-carbon electrode (Φ=3), leave standstill at 0-4 ℃ and solidified 72 hours.
(3) chiral Recognition
Isomers of phenylalanine solution with the elargol mark of 15 μ L steps (1) preparations joins in the 10mL0.02M phosphate buffer solution (pH:8) respectively, then two sensors are hatched 10 minutes respectively therein after, fully wash with distilled water.
(4) Yin oxidation dissolution
Two sensors finishing the chiral Recognition reaction are immersed respectively in the HNO3 solution of 200 μ L 50%, and vibration makes silver-colored oxidation dissolution, takes out glass-carbon electrode behind the 5min, and adds 1mL 10mM HNO
3-KNO
3Solution carries out Electrochemical Detection as supporting electrolyte in this solution
(5) electrochemical determination method is with embodiment 1
Claims (7)
1. the chiral sensor based on bovine serum albumin(BSA) is characterized in that, electrode surface covers the alumina sol-gel mould that contains bovine serum albumin(BSA) in this sensor, and the thickness range of film is 20～40nm; And the concentration of the bovine serum albumin(BSA) of alumina sol-gel mixing is 0.05-0.2mg mL
-1, the volume ratio of bovine serum albumin(BSA) and alumina sol-gel is 0.5: 1-1.2: 1.
2. sensor according to claim 1 is characterized in that electrode is screen printing electrode or glass-carbon electrode in this sensor.
3. the preparation method of sensor according to claim 1 is characterized in that, is 0.05-0.2mg mL with concentration
-1Bovine serum albumin(BSA) and alumina sol-gel mix, the volume ratio of bovine serum albumin(BSA) and alumina sol-gel is 0.5: 1-1.2: 1; Mixed solution is covered on the electrode, and 0-4 ℃ leaves standstill curing 60-80 hour, and the film thickness scope that obtains is 20～40nm; At last the above-mentioned electrode that makes is connected with electrochemical appliance, makes sensor.
4. the preparation method of sensor as claimed in claim 3 is characterized in that, mixed solution covers on the electrode by dipping, coating or dropping method.
5. the preparation method of sensor as claimed in claim 3 is characterized in that, the concentration of bovine serum albumin(BSA) is 0.09-0.15mg mL
-1
6. as the preparation method of sensor as described in the claim 3, it is characterized in that electrode is screen printing electrode or glass-carbon electrode in this sensor.
7. as the preparation method of sensor as described in the claim 3, it is characterized in that glass-carbon electrode is shaft-like in this sensor, diameter is the 2-4 millimeter.
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| CN101963564B (en) * | 2010-08-20 | 2012-06-06 | 中国科学院苏州纳米技术与纳米仿生研究所 | Chiral sensor and preparation method thereof |
| CN112326760A (en) * | 2020-10-22 | 2021-02-05 | 天津大学 | Preparation and detection method of epitaxial gate field effect transistor sensor for detecting chiral tryptophan |
| CN114544719A (en) * | 2022-01-10 | 2022-05-27 | 中国科学院化学研究所 | PH sensing electrode, preparation method thereof and electrochemical sensor |
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