CN111189783B - Detection method and application of D-glucose - Google Patents

Detection method and application of D-glucose Download PDF

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CN111189783B
CN111189783B CN202010013434.0A CN202010013434A CN111189783B CN 111189783 B CN111189783 B CN 111189783B CN 202010013434 A CN202010013434 A CN 202010013434A CN 111189783 B CN111189783 B CN 111189783B
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glucose
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cysteine
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molybdenum dioxide
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CN111189783A (en
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程佳吉
王秋实
郝俊杰
林家颖
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Hubei University
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Abstract

The invention provides a detection method and application of D-glucose. The detection method provided by the invention has the advantages that the molybdenum dioxide at the end sealed by the chiral cysteine is matched with the glucose oxidase (Gox), so that the detection of D-glucose can be realized, and the detection method has no response to other sugar molecule samples other than D-glucose and has high selectivity; meanwhile, the detection sensitivity is high, and the D-glucose detection Limit (LOD) is low.

Description

Detection method and application of D-glucose
Technical Field
The invention belongs to the technical field of chiral signal detection, and relates to a detection method and application of D-glucose.
Background
Chiral molecules in the chiral recognition enantiomers are very important, especially in the aspects of stereoselective synthesis, biosensing, bioimaging, the medical field and the like. Therefore, the development of efficient methods for efficiently identifying and quantifying enantiomerically pure molecules has become a major motivation for modern nanomaterial design.
To date, surface-modified metal nanoparticles, semiconductors, and carbon-based nanomaterials, etc. have been intensively studied for chiral recognition of biomolecules. However, current methods rely primarily on modulating the interaction between the nanomaterial surface and the chiral ligand through surface modification (e.g., chemical bonding and electrostatic attraction). Despite the great progress that has been made, the stability of nanomaterials and the sensitivity of chiral recognition are still unsatisfactory.
Ligand-induced chiral transition metal oxides with tunable absorption wavelengths are of wide interest for a wide range of potential applications, including biosensing, hyperspectral imaging, and optical detection. For example, Kotov et al disclose chiral WO modified with chiral ligands (e.g., proline, aspartic acid and cysteine)3-xAnd Co3O4The nanoparticles exhibit strong optical chirality, even enhanced when paramagnetic properties are present. In this case, the chirality is caused by the metal-ligand charge transfer (MLCT) effect, due toThe transition of the unpaired electrons from the metal delta orbital to the ligand-based pi and pi x orbitals indicates that the valence state of the metal atom is important for such atoms. There is still little current research on the chiral origin of MLCT.
The detection of glucose is generally based on ultraviolet or fluorescence spectrum analysis, and due to the universality of ultraviolet and fluorescence, namely ultraviolet absorption or fluorescence emission spectrum of a large amount of substances, the detection specificity is low, and chiral glucose (D-glucose and L-glucose) cannot be directly identified.
CN110231486A discloses a method for detecting glucose, comprising a glucose detection kit which comprises a glucose oxidase solution, an alkaline aqueous solution and MnO2NPs and luminol working solutions; a method for detecting glucose, comprising: 1) mixing a sample to be detected with a glucose oxidase solution with the concentration of 0.8-1.5 mg/mL, and reacting for 6-10min at the temperature of 30-37 ℃; 2) taking 100 mu L of reacted solution, 100 mu L of NaOH aqueous solution and 10 mu L of MnO with the concentration of 0.01-1.0mg/mL2Mixing NPs and luminol working solution; 3) the CL signal was measured and the glucose concentration was calculated according to the regression equation. Although the patent can detect the concentration of glucose, it cannot distinguish the concentration of chiral glucose.
Therefore, it is desirable to provide an assay that can identify and detect chiral glucose.
Disclosure of Invention
The invention aims to provide a detection method and application of D-glucose. The detection method provided by the invention has the advantages that the molybdenum dioxide at the end sealed by the chiral cysteine is matched with the glucose oxidase (Gox), so that the detection of D-glucose can be realized, and the detection method has no response to other sugar molecule samples other than D-glucose and has high selectivity; meanwhile, the detection sensitivity is high, and the D-glucose detection Limit (LOD) is low.
In order to achieve the purpose, the invention adopts the following technical scheme:
in a first aspect, the invention provides a method for detecting D-glucose, which comprises detecting by using molybdenum dioxide capped by chiral cysteine.
In the invention, the chemical valence of the molybdenum dioxide can be changed by the hydrogen peroxide, so that the chiral signal of the molybdenum dioxide at the chiral cysteine end is changed, and the glucose oxidase can only specifically catalyze the oxidation of the D-glucose to generate the hydrogen peroxide, so that the D-glucose can be specifically identified and detected by the molybdenum dioxide at the chiral cysteine end.
In the present invention, the detection method comprises the steps of:
(1) drawing a standard curve;
(2) mixing a sample to be detected with molybdenum dioxide at the end sealed by chiral cysteine, and detecting the circular dichroism spectrum of the mixed solution;
(3) and (3) determining the concentration of the D-glucose in the sample to be detected according to the CD peak absolute value of the circular dichroism spectrum obtained in the step (2) and corresponding to the standard curve.
In the invention, the standard curve takes the concentration of D-glucose as an abscissa and takes the CD peak absolute value of the circular dichroism spectrum of the molybdenum dioxide at the end capped by the chiral cysteine as an ordinate.
Because the CD peak change value of the circular dichroism spectrum of the molybdenum dioxide at the chiral cysteine end-sealed end and the hydrogen peroxide concentration change value are in a linear relation, and the glucose oxidase catalyzes the D-glucose to generate the hydrogen peroxide, the standard curve is in a linear relation, and the concentration of each D-glucose corresponds to a unique CD peak absolute value.
Namely, the CD peak value of the circular dichroism spectrum of the molybdenum dioxide at the chiral cysteine end in the sample to be tested is tested, and the concentration of the D-glucose in the sample to be tested can be obtained.
Preferably, the method for drawing the standard curve comprises the following steps:
(A) respectively preparing D-glucose solutions with different concentrations, wherein the D-glucose solutions comprise glucose oxidase;
(B) mixing the D-glucose solution with molybdenum dioxide at the chiral cysteine end, and detecting the CD peak absolute value of the molybdenum dioxide at the chiral cysteine end by using circular dichroism;
(C) and drawing a standard curve by taking the concentration of the D-glucose as an abscissa and taking the absolute value of the CD peak as an ordinate.
Preferably, the concentration of D-glucose in the D-glucose solution of step (A) is 0-100000. mu.M, such as 1. mu.M, 50. mu.M, 100. mu.M, 600. mu.M, 800. mu.M, 1000. mu.M, 5000. mu.M, 10000. mu.M, 50000. mu.M, 80000. mu.M and the like, preferably 200-.
Preferably, at least 3 or more (e.g., 4, 5, 6, 7, 8, etc.) D-glucose solutions with different concentrations are prepared in step (a), and more preferably 5 or more.
Preferably, the concentration of the glucose oxidase in the D-glucose solution is 50-400U/mL, such as 100U/mL, 150U/mL, 200U/mL, 250U/mL, 300U/mL, 350U/mL, etc., and more preferably 100U/mL.
Preferably, in the mixed solution in the step (B), the concentration of the molybdenum dioxide at the chiral cysteine end is 0.1-100mmol/L, such as 0.2mmol/L, 0.5mmol/L, 1mmol/L, 2mmol/L, 5mmol/L, 10mmol/L, 12mmol/L, 20mmol/L, 50mmol/L, 80mmol/L, 90mmol/L, etc., and further preferably 10 mmol/L.
Preferably, the mixing time in step (B) is 10-120min, such as 20min, 30min, 50min, 100min, 110min, etc., and further preferably 30 min.
Preferably, the molybdenum dioxide at the chiral cysteine end comprises molybdenum dioxide at the L-cysteine end and/or molybdenum dioxide at the D-cysteine end.
Preferably, the preparation method of the chiral cysteine-terminated molybdenum dioxide comprises the following steps:
chiral cysteine is used for reacting with molybdenum trioxide to obtain the molybdenum dioxide terminated by the chiral cysteine.
Preferably, the molar ratio of the chiral cysteine to the molybdenum trioxide is (50-200):3, such as 60:3, 70:3, 80:3, 85:3, 90:3, 95:3, 100:3, 120:3, 150:3, 180:3, etc., further preferably 100: 3.
Preferably, the reaction comprises incubation for 1 week after 5min of sonication in the dark.
Preferably, the molybdenum trioxide participates in the reaction in the form of a solution.
Preferably, the preparation method of the molybdenum trioxide comprises the following steps:
and mixing molybdenum disulfide and hydrogen peroxide for reaction to obtain the molybdenum trioxide.
Preferably, the chiral cysteine includes L-cysteine and/or D-cysteine;
preferably, the chiral cysteine is L-cysteine, and the molybdenum dioxide at the end of the chiral cysteine is L-cysteine-terminated molybdenum dioxide (L-Cys-MoO)2 NP)。
Preferably, the chiral cysteine is D-cysteine, and the molybdenum dioxide at the end of the chiral cysteine is D-cysteine-terminated molybdenum dioxide (D-Cys-MoO)2)。
To ensure Cys-MoO2The NP was well dispersed in the solution and samples in aqueous solution were purified by centrifugation for 3 minutes, removing the precipitate (if any) at 8000rpm and maintained at 20 ℃ until use.
In a second aspect, the present invention provides the use of the method for detecting D-glucose according to the first aspect for the detection of reactive oxygen radicals or dopamine in vivo.
Since the molybdenum dioxide at the cysteine end has sensitive response to the oxidant in the external environment, the sensing and the detection of the oxidants such as oxygen anions, hydroxyl radicals, dopamine, hypochlorite, hydrogen peroxide and the like generated in the metabolism in biological cells can be realized by the method.
Compared with the prior art, the invention has the following beneficial effects:
(1) in the invention, the chemical valence of the molybdenum dioxide can be changed by the hydrogen peroxide, so that the chiral signal of the molybdenum dioxide at the chiral cysteine end is changed, and the glucose oxidase can only specifically catalyze the oxidation of the D-glucose to generate the hydrogen peroxide, so that the D-glucose can be specifically identified and detected by the molybdenum dioxide at the chiral cysteine end.
(2) Because the CD peak change value of the circular dichroism spectrum of the molybdenum dioxide at the chiral cysteine sealed end is in a linear relation with the hydrogen peroxide concentration change value, and the glucose oxidase catalyzes the D-glucose to generate the hydrogen peroxide, the concentration of the D-glucose and the CD peak absolute value are in a linear relation, namely the concentration of the D-glucose in the sample to be detected can be obtained by utilizing the CD peak value of the circular dichroism spectrum of the molybdenum dioxide at the chiral cysteine sealed end in the sample to be detected.
Drawings
FIG. 1 is D-Cys-MoO synthesized in preparation example 12HRTEM of NP.
FIG. 2 is HRTEM-based D-Cys-MoO synthesized in preparation example 12Particle size distribution profile of NPs.
FIG. 3 is a circular dichroism spectrum of preparation example 1.
Fig. 4 is an XPS energy spectrum of the sample provided in preparation example 1.
Fig. 5 is a graph of the high resolution XPS spectra and fitting results for the Mo 3d region of the sample provided in preparation example 1.
Fig. 6 is a standard graph fitted in example 1.
Fig. 7 is a standard graph of the fit in example 2.
FIG. 8 is D-Cys-MoO2The results of a selective study of NP with various sugars.
FIG. 9 is a graph of a fit of the detection limits for D-glucose in performance tests.
Detailed Description
The technical solution of the present invention is further described below by way of specific embodiments. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
Preparation example 1
D-cysteine-terminated molybdenum dioxide nanoparticles (D-Cys-MoO)2NP), the preparation method is as follows:
(1)MoO3preparation of the solution:
with vigorous stirring, 0.8g of the original black MoS2The powder (5mmol) was dissolved in 462.5mL of deionized water, after which 37.5mL of 30 wt% H was added2O2Adding to the prepared solution; the black mixture then turned clear yellow and the solution was heated to 80 ℃ to remove excess H2O2. After the mixed dispersion became transparent, the heat treatment was stopped.
(2) Preparation of D-Cys-MoO2 NP：
60mg of D-cysteine (D-Cys) was added to 1.5mL (10mM) of MoO obtained in step (1)3Solution, sonicating the mixture for 5 minutes, and then incubating in the dark for 1 week to obtain D-Cys-MoO2 NP。
Preparation example 2
L-cysteine-terminated molybdenum dioxide nanoparticle (L-Cys-MoO)2NP), preparation method reference is made to preparation example 1, except that D-Cys is replaced by L-Cys.
Performance test 1
The performance test of the chiral cysteine-capped molybdenum dioxide nanoparticles provided in preparation examples 1-2 was performed by the following method:
(1) particle size distribution: observing the particle size by using a high-resolution transmission electron microscope (HRTEM);
FIG. 1 shows D-Cys-MoO synthesized in preparation example 12HRTEM image of NP, FIG. 2 is D-Cys-MoO synthesized in HRTEM-based preparation example 12The particle size distribution diagram of NP, which observes and counts 100 individual nanoparticles, can be seen from FIG. 1 and FIG. 2, and the particle size of the molybdenum dioxide nanoparticles with chiral cysteine end capping is in the range of 24.9 + -0.8 mm.
(2) Circular dichroism spectrum test: performing circular dichroism spectrum test by using a JASCO J-1500 circular dichroism instrument;
FIG. 3 is a circular dichroism spectrum of preparation example 1, and it can be seen that a strong CD signal can be observed. Two CD bands at 376nm and 580nm, hereinafter denoted as peak (I) and peak (II), were recorded, respectively, the chiral enantiomers of the ligand showed opposite linear shapes, while pure L-or D-cysteine had CD bands at 220nm, indicating that the preparation of the present invention yielded chiral cysteine-capped molybdenum dioxide nanoparticles.
(3) Elemental analysis of the sample: analysis by X-ray photoelectron spectroscopy (XPS);
FIG. 4 is a XPS energy spectrum of the sample provided in preparative example 1, FIG. 5 is a plot of the high resolution XPS spectrum of the Mo 3d region and the results of a fit, FIG. 4 demonstrates the presence of cysteine and molybdenum and oxygen, FIG. 5 when fitting the high resolution XPS spectrum of Mo 3d, the splitting energy of the Mo 3d5/2-Mo 3d3/2 doublet is about 3.15eV, the fixed area ratio is 3:2, the fit requires the use of two positions on the molybdenum 3d5/2 peak, one for Mo (IV), one for Mo (VI), 229.2eV and 232.5eV, respectively, consistent with literature reports; contribution of this higher oxidation state of Mo (Mo VI) (Mo VI)<5%) may be due to MoO2Partial surface oxidation of the nanoparticles. The Mo IV ratio according to the XPS results was about 94.8%. The existence of the molybdenum dioxide is proved; the shoulder peak at 226.9eV may be due to the S2S contribution of the cysteine ligand grafted onto the NP, which is also confirmed by the S2 p peak at 161.8 eV.
Example 1
A method for detecting D-glucose comprises the following steps:
(1) drawing a standard curve:
a. preparing 0.5mL of an aqueous solution of Gox and D-glucose, which contains 80. mu.L of Gox (5U/. mu.L) and different concentrations of D-glucose, and incubating the enzymatic reaction system for 30 min;
wherein the D-glucose concentrations were 200. mu.M, 400. mu.M, 600. mu.M, 800. mu.M and 1000. mu.M, respectively.
b. 1.5mL of D-Cys-MoO2A solution (400. mu.L, 10mM) was added to the above solution, the reaction system was continuously stirred for 30min, and the CD peak absolute value of molybdenum dioxide at the chiral cysteine end was detected by circular dichroism.
c. And drawing a standard curve by taking the concentration of the D-glucose as an abscissa and taking the absolute value of a CD peak as an ordinate.
(2) A sample to be detected and D-Cys-MoO are mixed2Mixing with a solvent, and detecting the circular dichroism spectrum of the mixed solution;
(3) and (3) determining the concentration of the D-glucose in the sample to be detected according to the CD peak absolute value of the circular dichroism spectrum obtained in the step (2) and corresponding to the standard curve.
FIG. 6 is a schematic view ofFrom the standard curve fitted in example 1, the correlation coefficient R is shown20.988 > 0.98, indicating a good linearity.
Example 2
The difference from example 1 is that D-Cys-MoO2Replacement by L-Cys-MoO2。
FIG. 7 is a graph showing the correlation coefficient R of the calibration curve obtained in example 220.997 > 0.99, indicating a good linearity.
Performance test 2
The detection method provided by the embodiment is verified, and the method comprises the following steps:
(1) and (3) verifying the accuracy:
preparing a solution to be tested of D-glucose, wherein the solution comprises 80 mu L of Gox (5U/. mu.L) and D-glucose with different concentrations, and incubating an enzymatic reaction system for 30 min;
wherein the D-glucose concentrations are 385 muM, 560 muM and 937 muM respectively,
then, the detection method provided by the embodiment is used for detection, and the detection result is shown in table 1:
TABLE 1
Detection method Measured value (μ M) Preparation number (μ M) Error/%)
Example 1 400.4 385 4.0
Example 1 546.9 560 2.3
Example 1 925.8 937 1.2
Example 2 406.9 385 5.7
Example 2 539.3 560 3.7
Example 2 932.3 937 0.5
According to the embodiment and the performance test, the detection method provided by the invention can be used for accurately detecting the D-glucose, and has the advantages of higher detection accuracy, smaller error and less than 6 percent of error.
(2) Selectivity study: the system is utilized to detect different sugars, and research shows that only D-glucose has obvious response and proves the specific recognition of the D-glucose;
FIG. 8 is D-Cys-MoO2The results of the selectivity studies of NP against various sugars are shown. As can be seen from FIG. 8, the system has a response only to D-glucoseIt should not respond to L-glucose and other saccharides.
(3) Limit of detection (LOD): preparing mixed solutions of D-glucose concentrations of 0. mu.M, 1. mu.M, 3. mu.M, 5. mu.M, 10. mu.M, 30. mu.M and 50. mu.M, respectively, containing 80. mu.L of Gox (5U/. mu.L), and performing a test with reference to a method for drawing a standard curve;
fig. 9 is a graph of the fitted detection limit, and it can be seen that the fitted curve y is a + bx, a is 0.455, b is 0.218, and R is20.992; the limit of detection (LOD) was calculated to be 0.446. mu.M.
As can be seen from the examples and performance tests, the detection method provided by the invention can realize specific detection of D-glucose, has high detection accuracy and sensitivity, and has a low detection limit of D-glucose below 0.446. mu.M.
The applicant states that the present invention is illustrated by the above examples to the detection method and application of D-glucose, but the present invention is not limited to the above process steps, i.e. it does not mean that the present invention must rely on the above process steps to be carried out. It will be apparent to those skilled in the art that any modification of the present invention, equivalent substitutions of selected materials and additions of auxiliary components, selection of specific modes and the like, which are within the scope and disclosure of the present invention, are contemplated by the present invention.

Claims (23)

1. The detection method of the D-glucose is characterized by comprising the step of detecting by using molybdenum dioxide blocked by chiral cysteine.
2. The method for detecting D-glucose according to claim 1, wherein the method comprises the steps of:
(1) drawing a standard curve;
(2) mixing a sample to be detected with molybdenum dioxide at the end sealed by chiral cysteine, and detecting the circular dichroism spectrum of the mixed solution;
(3) and (3) determining the concentration of the D-glucose in the sample to be detected according to the CD peak absolute value of the circular dichroism spectrum obtained in the step (2) and corresponding to the standard curve.
3. The method for detecting D-glucose according to claim 2, wherein the standard curve has a D-glucose concentration as an abscissa and an absolute value of a CD peak of a circular dichroism spectrum of the molybdenum dioxide capped with the chiral cysteine as an ordinate.
4. The method for detecting D-glucose according to claim 2 or 3, wherein the standard curve is plotted by the method comprising the steps of:
(A) respectively preparing D-glucose solutions with different concentrations, wherein the D-glucose solutions comprise glucose oxidase;
(B) mixing the D-glucose solution with molybdenum dioxide at the chiral cysteine end, and detecting the CD peak absolute value of the molybdenum dioxide at the chiral cysteine end by using circular dichroism;
(C) and drawing a standard curve by taking the concentration of the D-glucose as an abscissa and taking the absolute value of a CD peak as an ordinate.
5. The method for detecting D-glucose according to claim 4, wherein the concentration of D-glucose in the D-glucose solution in the step (A) is 0 to 100000. mu.M.
6. The method for detecting D-glucose as claimed in claim 5, wherein the concentration of D-glucose in the D-glucose solution in step (A) is 200 μ M and 1000 μ M.
7. The method for detecting D-glucose according to claim 4, wherein 3 or more D-glucose solutions having different concentrations are prepared in the step (A).
8. The method for detecting D-glucose according to claim 7, wherein more than 5 kinds of D-glucose solutions having different concentrations are prepared in the step (A).
9. The method for detecting D-glucose according to claim 8, wherein the concentration of the glucose oxidase in the D-glucose solution is 50 to 400U/mL.
10. The method for detecting D-glucose as claimed in claim 4, wherein the concentration of the molybdenum dioxide at the end of the chiral cysteine in the mixed solution in the step (B) is 0.1-100 mmol/L.
11. The method for detecting D-glucose in claim 10, wherein the concentration of the molybdenum dioxide at the chiral cysteine end-capping in the mixed solution in the step (B) is 10 mmol/L.
12. The method for detecting D-glucose in accordance with claim 4, wherein the mixing time in step (B) is 10 to 120 min.
13. The method for detecting D-glucose according to claim 12, wherein the mixing time in the step (B) is 30 min.
14. The method for detecting D-glucose as claimed in claim 1, wherein the molybdenum dioxide at the end of the chiral cysteine comprises molybdenum dioxide at the end of the L-cysteine and/or molybdenum dioxide at the end of the D-cysteine.
15. The method for detecting D-glucose as claimed in claim 1, wherein the preparation method of the molybdenum dioxide capped with the chiral cysteine is as follows:
chiral cysteine is used for reacting with molybdenum trioxide to obtain the molybdenum dioxide terminated by the chiral cysteine.
16. The method for detecting D-glucose as claimed in claim 15, wherein the molar ratio of the chiral cysteine to the molybdenum trioxide is (50-200): 3.
17. The method for detecting D-glucose according to claim 15, wherein the reaction comprises incubating for 1 week after 5min with ultrasound under dark conditions.
18. The method for detecting D-glucose according to claim 15, wherein the molybdenum trioxide is reacted in the form of a solution.
19. The method for detecting D-glucose according to claim 18, wherein the method for preparing molybdenum trioxide comprises the steps of:
and mixing molybdenum disulfide and hydrogen peroxide for reaction to obtain the molybdenum trioxide.
20. The method for detecting D-glucose in accordance with claim 15, wherein the chiral cysteine comprises L-cysteine and/or D-cysteine.
21. The method for detecting D-glucose as claimed in claim 20, wherein the chiral cysteine is L-cysteine, and the molybdenum dioxide capped by the chiral cysteine is L-cysteine-capped molybdenum dioxide.
22. The method for detecting D-glucose as claimed in claim 20, wherein the chiral cysteine is D-cysteine, and the molybdenum dioxide capped by the chiral cysteine is D-cysteine-capped molybdenum dioxide.
23. Use of the method for the detection of D-glucose according to any one of claims 1-22 in the detection of reactive oxygen radicals or dopamine in vivo.
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