CN116177498B - Chiral selenium nano-film with light response, preparation method thereof and application thereof in detection of L-kynurenine - Google Patents
Chiral selenium nano-film with light response, preparation method thereof and application thereof in detection of L-kynurenine Download PDFInfo
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B19/00—Selenium; Tellurium; Compounds thereof
- C01B19/02—Elemental selenium or tellurium
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N27/00—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means
- G01N27/26—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating electrochemical variables; by using electrolysis or electrophoresis
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N27/00—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means
- G01N27/26—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating electrochemical variables; by using electrolysis or electrophoresis
- G01N27/403—Cells and electrode assemblies
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
- Y02P70/50—Manufacturing or production processes characterised by the final manufactured product
Abstract
The invention provides a chiral selenium nano-film with light response, a preparation method thereof and application thereof in detecting L-kynurenine, and belongs to the field of two-dimensional nano-film biotechnology detection. According to the invention, cysteine chiral ligand is introduced in the synthesis process, so that chiral selenium nano-particles are obtained, and the chiral selenium nano-particles are subjected to liquid-liquid interface self-assembly, so that the single-layer uniform chiral selenium nano-film with light response can be prepared. The chiral selenium nano-film with the light response prepared by the invention can be used for detecting the content of L-kynurenine in human body. Under the illumination condition, the chiral selenium nano film obtains light response current, and after L-kynurenine is added, a photocurrent signal is weakened, so that a standard curve of the photocurrent signal and the concentration of the L-kynurenine is established, and the content of the L-kynurenine in a sample can be detected. Compared with the traditional detection method, the detection method has the advantages of low cost, high sensitivity, convenience and rapidness and good practical application prospect.
Description
Technical Field
The invention relates to the field of two-dimensional nano-film ion channel detection, in particular to a chiral selenium nano-film with light response, a preparation method thereof and application thereof in detecting L-kynurenine.
Background
L-kynurenine (Kyn) is one of the metabolites of the human essential amino acid tryptophan (L-Trp). Trp is most metabolized in mammals via the kynurenine (Kyn) metabolic pathway. Kyn and its metabolites are closely related to various neuropsychiatric diseases, renal failure, cataracts, various chronic malignant diseases, etc. Therefore, quantitative determination of Kyn content in organisms has important reference value for researches such as diagnosis and treatment of related diseases, curative effect monitoring and pathogenesis.
Liquid Chromatography (LC) -Mass Spectrometry (MS) has become the most highly sensitive and high throughput metabolic analysis, however LC-MS involves time consuming, expensive and complex procedures. Therefore, developing a detection technique with high sensitivity and easy operation is an important task. The modification sites with controllable nano channel size and surface diversity of the artificial nano channel provide great possibility for constructing functional ion channels, and the nano channel constructed by self-assembly of nano particles has higher specific surface area and nano size effect, simple sample adding, lower equipment and cost and wide application value in the separation and detection fields.
Therefore, the chiral nano-channel technology is of great significance in identifying and detecting the L-KYn.
Disclosure of Invention
In order to solve the problems, the invention provides a chiral selenium nano-film with light response, a preparation method thereof and application thereof in detecting L-kynurenine. The invention adopts a monolayer chiral selenium nano-film formed by self-assembly of chiral selenium nano-particles and anodic aluminum oxide to construct a chiral nano-channel. When L-kynurenine passes through the chiral nano-channel, different current signals are displayed, and the characteristic can be utilized to realize the identification and detection of the L-kynurenine.
The invention is realized by the following technical scheme:
the first object of the invention is a preparation method of chiral selenium nano-film with light response, comprising the following steps:
(1) SeO addition to surfactant solutions 2 Mixing and stirring the solution and chiral ligand; adding water and a reducing agent to react to obtain chiral selenium nano-particles;
(2) Mixing the chiral selenium nano-particles obtained in the step (1) with an organic solvent, dropwise adding alcohol, transferring to a substrate after the organic solvent volatilizes, and performing thermal fixation to prepare the chiral selenium nano-film with light response.
In one embodiment of the invention, in step (1), the surfactant is selected from PVP and/or CTAB.
In one embodiment of the present invention, in step (1), the PVP has a molecular weight of 8K-13K.
In one embodiment of the invention, in step (1), the chiral ligand is selected from the group consisting of L/D-cysteine molecules and/or L/D-cysteine molecule derivatives.
In one embodiment of the present invention, in step (1), the reducing agent is selected from NaBH 4 。
In one embodiment of the present invention, in step (2), the organic solvent is selected from one or more of n-hexane, chloroform and toluene.
In one embodiment of the invention, in step (2), the substrate is selected from a porous anodized aluminum template.
In one embodiment of the present invention, in step (2), the conditions for the thermal fixing are: and drying at 70 ℃ for 4-12 h.
In one embodiment of the invention, the method further comprises the step of repeating the step (1) and the step (2) to prepare the multilayer chiral selenium nano-film, wherein the number of layers of the film is 2-15.
The second object of the invention is to provide the chiral selenium nano-film with light response obtained by the preparation method.
The third object of the invention is to provide the application of the chiral selenium nano-film with light response in detecting L-kynurenine.
In one embodiment of the invention, the method of application comprises the steps of:
and (3) placing the chiral selenium nano-film with the light response in a sample cell with a hole, incubating with a solution containing L-kynurenine, detecting a photocurrent signal under the illumination condition, and carrying out qualitative or quantitative analysis of the L-kynurenine.
In one embodiment of the invention, the illumination conditions are: the illumination wavelength is 405nm-660nm; the illumination intensity is 5mw/m 2 -80 mw/m 2 The method comprises the steps of carrying out a first treatment on the surface of the The illumination time is 10s-60s.
In one embodiment of the present invention, the concentration of L-kynurenine is 1X 10 -1 mM-1×10 -8 mM。
In one embodiment of the invention, the minimum limit of detection is 0.0074nM.
According to the technical scheme, the method for detecting the L-kynurenine by using the chiral selenium nanochannel is adopted, the chiral nanochannel is placed in the middle of a porous electrolyte sample cell to serve as an ion channel, and the detection of the L-kynurenine can be realized by adopting electrochemical test of ion transmission signals containing different concentrations of kynurenine.
In one embodiment of the invention, the preparation method of the chiral selenium nano-film with light response comprises the following steps:
(1) Adding SeO to PVP solution 2 Mixing and stirring the solution with 5mM-75mM chiral ligand solution; adding ultrapure water during stirring, and adding NaBH 4 Continuing to react for 2.5-12 hours, and obtaining chiral selenium nano particles after the reaction is finished; centrifuging the prepared chiral selenium nano-particles twice and re-suspending the chiral selenium nano-particles in an equal volume of ultrapure water, wherein the centrifugal speed is 7500rpm for 10min;
(2) Transferring the chiral selenium nano-particles to a substrate in a liquid-liquid self-assembly (LBL) mode, and performing thermal fixation to prepare a single-layer chiral selenium nano-film;
(3) Using the preparation method of the single-layer film, carrying out multi-layer film transfer to obtain a multi-layer chiral selenium film;
(4) And placing the single-layer or multi-layer chiral selenium nano-film into a specific electrolytic cell for photocurrent testing. Wherein the electrolyte solution KCl has an electrolyte concentration of 0.01mM-100mM.
The chiral selenium nano film with the light response is obtained by adopting chiral selenium nano particles to induce self-assembly at an n-hexane-ethanol interface through dropwise adding absolute ethyl alcohol. The chiral selenium nano-channel is placed in the middle of the electrolyte sample cell with the hole to be used as an ion channel, and light stimulation generates a photocurrent signal.
In one embodiment of the present invention, the specific method of application comprises the steps of:
(1) Preparing standard curves between L-kynurenine with different concentrations and photocurrent signals; preparing L-kynurenine standard solutions with different concentrations, adding the standard solutions into a chiral selenium nano-film ion channel detector, respectively incubating for a period of time, then detecting photocurrent signals, and establishing standard curves between the L-kynurenine with different concentrations and the photocurrent signals;
(2) Sample detection: and adding the serum sample and the cerebrospinal fluid sample into the chiral selenium nano-film ion channel for testing, and calculating the concentration of the L-kynurenine through a working curve.
The technical scheme of the invention has the following advantages:
(1) The invention provides a chiral selenium nano-film with light response, a preparation method and application thereof in detecting L-kynurenine, which can obtain a strong chiral two-dimensional selenium nano-film material through simple and low-price nano-material self-assembly and provide a new thought for preparing chiral nano-particles and chiral nano-films.
(2) The invention drives ion transportation under illumination condition to obtain photocurrent signals, realizes conversion from light energy to electric energy and has great potential in the field of energy conversion. The chiral nano channel directly recognizes and detects the L-kynurenine through the different recognition capacities of the L, D-kynurenine and the huge difference of photocurrent signals, thereby realizing the ultrasensitive detection of the L-kynurenine. This has great potential for chiral recognition bioassays.
Drawings
In order that the invention may be more readily understood, a more particular description of the invention will be rendered by reference to specific embodiments thereof that are illustrated in the appended drawings.
FIG. 1 is a transmission electron microscope image of chiral selenium nanoparticles of example 1 of the present invention;
FIG. 2 is a circular dichroism spectrum (FIG. 2-A) and an absorption spectrum (FIG. 2-B) of chiral selenium nanoparticles of example 1 of the present invention;
FIG. 3 is a transmission electron microscope image of the chiral selenium nano-film of example 2 of the present invention;
FIG. 4 is a macroscopic photograph of the chiral selenium nano-film of example 2 of the present invention;
FIG. 5 is a circular dichroism spectrum (FIG. 5-A) and an absorption spectrum (FIG. 5-B) of the chiral selenium nano-film of example 2 of the present invention;
FIG. 6 is a graph of photocurrent versus time for a chiral selenium nanofilm channel of example 4 of the present invention with different configurations of kynurenine; wherein fig. 6-a is a photocurrent-time graph of D-type chiral selenium nanomembrane; FIG. 6-B is a graph of photocurrent versus time for an L-type chiral selenium nanomembrane;
FIG. 7 is a graph of photocurrent versus time for the chiral selenium nanomembrane channel of example 5 of the present invention with different concentrations of kynurenine added; wherein fig. 7-a is a graph of photocurrent versus time for different concentrations of D-kynurenine; FIG. 7-B is a graph of photocurrent versus time for different concentrations of L-kynurenine;
FIG. 8 is a graph of the photocurrent versus time plot obtained from FIG. 7 plotted as a function of kynurenine concentration in example 5 of the present invention;
FIG. 9 is a graph showing the detection of channel specificity of the prepared photo-responsive chiral selenium nano-film in example 6 of the present invention;
FIG. 10 is a circular dichroism spectrum of chiral selenium nanoparticle prepared by different chiral ligands in example 7 of the present invention.
Detailed Description
The present invention will be further described with reference to the accompanying drawings and specific examples, which are not intended to be limiting, so that those skilled in the art will better understand the invention and practice it.
Example 1 preparation of chiral selenium nanoparticles.
(1) 1mL of 0.1M SeO was added to 0.5mL of 50mg/mL PVP (polyvinylpyrrolidone) solution 2 Stirring the solution, adding 2.5mL and 0.3M L/D-Cys in the stirring process, and continuously stirring;
(2) 4.5mL of ultrapure water was added while stirring, and 2.5mL of 0.1MNaBH was added 4 And (3) carrying out a reaction for 2.5h, and obtaining the chiral selenium nano-particles after the reaction is finished. The chiral selenium nano-particles are subjected to electron microscopy and chiral test, and the characterization results are shown in fig. 1 and 2.
FIG. 1 is a transmission electron microscope image of chiral selenium nanoparticles; fig. 2 is a circular dichroism spectrum of chiral selenium nanoparticle. As can be seen from fig. 1 and fig. 2, the chiral selenium nanoparticle prepared by the method is a uniform and dispersed particle, the morphology of the chiral selenium nanoparticle is the morphology and spectrum signal which are not reported at present, the flower-like monodisperse 50nm selenium nanoparticle has a chiral signal range of 300nm-700nm, and the chiral signal of the chiral molecule is before 300nm, so that the chiral nanoparticle obtains a circular dichroism signal in the ultraviolet region, which possibly induces the chiral signal of the selenium nanoparticle due to the addition of the chiral molecule in the synthesis process, thus indicating the successful preparation of the chiral selenium nanoparticle.
Example 2 preparation of light-responsive chiral selenium nanofilm.
4mL of the chiral selenium nanoparticle obtained in example 1 was placed in a 6-well plate, 1.5mL of n-hexane was added thereto, and a significant liquid-liquid interfacial delamination phenomenon was observed in the container. To this was added dropwise 2mL of absolute ethanol, and a clear selenium film formation was observed at the liquid-liquid interface. After the n-hexane at the upper layer is completely volatilized, transferring the selenium film to the surface of a purchased porous anodic aluminum oxide template through a layer-by-layer self-assembly technology (LBL technology) to obtain the chiral nano channel. And (3) drying the obtained chiral nano-channel in a drying oven at 70 ℃ for 4 hours for thermal fixation to prepare the photoresponsive chiral selenium nano-film. The results of electron microscopy and chiral test characterization of the photoresponsive chiral selenium nanofilm are shown in fig. 3, 4 and 5. Multiple selenium films can be prepared by repeating the above steps for subsequent experimental use.
Fig. 3 is a TEM spectrum of a single-layer selenium nano-film, fig. 4 is a macroscopic photograph of the single-layer selenium nano-film, and fig. 5 is a spectral characterization of the single-layer selenium nano-film. As can be seen from fig. 3, 4 and 5, this example can produce a uniform selenium nanofilm whose spectral characterization demonstrates the successful production of chiral films.
Example 3 light stimulated electrochemical testing of chiral selenium nanochannels.
The chiral selenium nano channel (chiral selenium nano film) is arranged between two organic glass cubes (sample cells) with the volume of 2mL, and the used cubes are provided with pores with the diameter of 3mm, so that the two cubes are communicated with the nano channel. In both sample cells, an Ag/AgCl electrode was connected to each cell, and an electrochemical signal was measured, wherein the electrolyte used was KCl solution with a concentration of 0.01M. By electrochemical operationThe station tests the current-time change condition of the system to obtain an open-circuit current-time curve. The illumination adopts 405nm laser to irradiate one side of the selenium nano film of the nano channel, and the electrochemical signal test is carried out on the light response chiral selenium nano film while the illumination is carried out. The illumination time is 60s, and the light source intensity is 60mW/m 2 。
Example 4 identification of kynurenine enantiomer.
In both sample cells for electrochemical tests, an L-or D-form kynurenine aqueous solution was simultaneously added to both sample cells in addition to 2mL of 10mM KCl solution so that the final concentration of kynurenine in the electrolyte solution was 100. Mu.M. After addition of kynurenine solution, the whole system was incubated at room temperature for 10min and then subjected to electrochemical testing. Testing an electrochemical curve of the D-type chiral selenium nano film before kynurenine is added, wherein the photocurrent is 38.9nA; after incubation for 10min with L-kynurenine, the electrochemical curve was tested, with a photocurrent of 4.16nA and after addition of D-kynurenine with a photocurrent of 38.1nA. Testing an L-shaped chiral selenium nano film, and testing an electrochemical curve before kynurenine is added, wherein the photocurrent is 38.5nA; after 10min incubation with D-kynurenine, the electrochemical curve was tested, with photocurrent 4.56nA, and after L-kynurenine was added, photocurrent 37nA; the results of the specific electrochemical tests are shown in fig. 6. As can be seen from fig. 6, under the illumination condition, the photocurrent of the D-type selenium nano-film reaches 38.9nA, after L-kynurenine is added, the photocurrent is obviously reduced to 4.16nA, and after D-kynurenine is added, the photocurrent is almost unchanged, and the L-type chiral selenium nano-film also shows obvious photocurrent response to L-kynurenine, which indicates that the chiral selenium nano-film has good selective identification for kynurenine. The D-type chiral selenium nano-film has good selectivity to L-kynurenine.
Example 5 detection of L-kynurenine.
(1) A standard curve between kynurenine and photocurrent signals of different concentrations is prepared: preparing kynurenine standard solutions with different concentrations, adding the kynurenine standard solutions into a D-selenium nano-film ion channel detector, respectively incubating for a period of time, and then detecting photocurrent signals to establish D-dogs with different concentrationsA standard curve between urinary, L-kynurenine and photocurrent signals; as particularly shown in fig. 7 and 8; as can be seen from FIGS. 7 and 8, the photocurrent decreased linearly with the change of the L-kynurenine concentration, and a linear detection range of 1X 10 of the L-kynurenine standard curve was established -1 mM-1×10 -8 mM, minimum limit of detection of 0.0074nM; the chiral selenium nano-film prepared by the invention has extremely high sensitivity and can meet the measurement of kynurenine in human body.
(2) True sample detection:
test object: a total of 10 patients diagnosed with Alzheimer's Disease (AD) (diagnosed by clinical detection means) were diagnosed by clinical diagnosis, and a total of 10 healthy volunteers. Electrochemical tests were performed to obtain corresponding photocurrent-time curves, and kynurenine concentrations were calculated from the working curves, with the results shown in table 1.
TABLE 1 concentration of kynurenine in vivo in Alzheimer's disease and healthy volunteers
As can be seen from Table 1, in the sera of 10 patients with Alzheimer's disease and 10 healthy volunteers provided in hospitals, it was detected that the content of L-kynurenine in the serum of healthy volunteers (0.820.+ -. 0.38. Mu. Mol/L) was lower than that in the serum of patients with Alzheimer's disease (1.132.+ -. 0.066. Mu. Mol/L), indicating that the content of L-kynurenine in the serum of AD patients would be higher than that of normal persons; in a cerebrospinal fluid sample provided by a hospital, detecting that the content of L-kynurenine in cerebrospinal fluid of a healthy volunteer (0.105+/-0.061 mu mol/L) is lower than the content in cerebrospinal fluid of a patient with Alzheimer disease (0.150+/-0.065 mu mol/L); it follows that L-kynurenine is present in a higher amount in AD patients than in healthy persons. Thus, kynurenine in serum and cerebrospinal fluid can be detected by the method of the invention.
Example 6 specific detection of chiral selenium nanomembranes.
In both sample cells for electrochemical tests, an aqueous solution of L-or D-form chiral amino acid molecules (kynurenine, phenylalanine, serine, aspartic acid, glutamic acid, histidine, glucose and mixed solution) was simultaneously added to both sample cells, except for 2mL of KCl solution at a concentration of 10mM, so that the final concentration of the amino acid in the KCl solution was 100. Mu.M. After the amino acid solution was added, the whole system was incubated at room temperature for 10min and then subjected to electrochemical test. The electrochemical test results are shown in fig. 9.
The result of fig. 9 shows that the chiral selenium nano-film has good specificity for L-kynurenine, has better recognition capability for L-kynurenine, and cannot be interfered by other biological samples.
Example 7 other chiral molecules chiral selenium nanoparticles were prepared.
The same procedure as in example 1 was followed except that penicillamine, glutathione, tartaric acid, histidine, phenylalanine, glutamic acid, aspartic acid, lysine, cystine, cysteine methyl ester hydrochloride, cysteine hydrochloride, N-acetylcysteine, dipeptide (cysteine-phenylalanine) were added instead of cysteine in the synthesis, and selenium nanoparticle was obtained after the reaction. The selenium nano-particle is subjected to chiral test, and the characterization result is shown in figure 10, so that a chiral peak of cysteine hydrochloride at about 428nm and other chiral signals are obtained. It can be seen that the cysteine molecule and the derivative of the cysteine molecule are unique in the process of synthesizing chiral selenium nanoparticles.
It is apparent that the above examples are given by way of illustration only and are not limiting of the embodiments. Other variations and modifications of the present invention will be apparent to those of ordinary skill in the art in light of the foregoing description. It is not necessary here nor is it exhaustive of all embodiments. And obvious variations or modifications thereof are contemplated as falling within the scope of the present invention.
Claims (8)
1. The application of the chiral selenium nano-film with the light response in detecting the L-kynurenine is characterized in that the preparation method of the chiral selenium nano-film with the light response comprises the following steps:
(1) SeO addition to surfactant solutions 2 Mixing and stirring the solution and chiral ligand; adding water and a reducing agent to react to obtain chiral selenium nano-particles;
(2) Mixing the chiral selenium nano-particles obtained in the step (1) with an organic solvent, adding alcohol, transferring to a substrate after the organic solvent volatilizes, and performing thermal fixation to prepare the chiral selenium nano-film with light response.
2. Use according to claim 1, wherein in step (1) the surfactant is selected from PVP and/or CTAB; the molecular weight of PVP is 8K-13K.
3. The use according to claim 1, wherein in step (1) the chiral ligand is selected from the group consisting of L/D-cysteine molecules and/or L/D-cysteine molecule derivatives.
4. The use according to claim 1, wherein in step (1) the reducing agent is selected from NaBH 4 The method comprises the steps of carrying out a first treatment on the surface of the The substrate is selected from a porous anodized aluminum template.
5. The use of claim 1, further comprising repeating step (1) and step (2) to produce a multilayer chiral selenium nanofilm, wherein the number of layers of the film is 2-15.
6. The application according to claim 1, characterized in that the method of application comprises the steps of:
and (3) placing the chiral selenium nano-film with the light response in a sample cell with a hole, incubating with a solution containing L-kynurenine, detecting a photocurrent signal under the illumination condition, and carrying out qualitative or quantitative analysis of the L-kynurenine.
7. The use according to claim 6, wherein the illumination conditions are: the illumination wavelength is 405nm-660nm; the illumination intensity is 5mw/m 2 -80 mw/m 2 The method comprises the steps of carrying out a first treatment on the surface of the The illumination time is 10s-60s.
8. The use according to claim 6, wherein the concentration of L-kynurenine is 1 x 10 -1 mM-1×10 -8 mM。
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