CN110981896B - Preparation method and application of 11-mercaptoundecanoic acid modified gold nanocluster - Google Patents
Preparation method and application of 11-mercaptoundecanoic acid modified gold nanocluster Download PDFInfo
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Abstract
The invention provides a preparation method and application of a 11-mercaptoundecanoic acid modified gold nanocluster, wherein the preparation method comprises the following steps: dissolving 11-mercaptoundecanoic acid in alkaline ultrapure water, adding HAuCl under stirring4And standing the mixture in the dark for reaction, adding absolute ethyl alcohol, centrifuging and collecting precipitates to obtain the 11-mercaptoundecanoic acid modified gold nanocluster. The 11-mercaptoundecanoic acid modified gold nanocluster is used for detecting the content of glutathione. The method selects the gold nanoclusters with good fluorescence performance, long fluorescence life and simple and rapid synthesis as a detection platform, and realizes simple, rapid and sensitive detection of the glutathione by regulating and controlling copper ions.
Description
Technical Field
The present invention relates to the field of gold nanoclusters. More specifically, the invention relates to a preparation method and application of a 11-mercaptoundecanoic acid modified gold nanocluster.
Background
Reduced Glutathione (GSH) is a tripeptide consisting of glutamic acid, cysteine and glycine, is widely present in cells and tissues of animals and human bodies, can help to maintain the functions of a normal immune system, has the functions of detoxification, antioxidation and the like, and is widely used for the auxiliary treatment of alcohol, medicaments (chemotherapeutic drugs, antitumor drugs, antituberculosis drugs and the like) and liver injury caused by other various reasons clinically. Meanwhile, glutathione is involved in many physiological processes including xenobiotic metabolism, intracellular signaling and gene regulation. More importantly, glutathione is involved in the regulation of cancer cell death, including apoptosis, necrosis and autophagy. The increase in glutathione content in cancer cells can trigger resistance of cancer cells to chemotherapeutic drugs (e.g., doxorubicin). In addition, the concentration level of GSH can be used as an index for various diseases such as Parkinson's disease, Alzheimer's disease, AIDS, arthritis, diabetes and atherosclerosis, so that a highly sensitive and highly selective method for detecting glutathione is required.
For detecting GSH, the existing detection means mainly comprise an enzyme cycling method, a chromatography method, an electrophoresis method, an electrochemical analysis method and a fluorescence spectrometry method. The fluorescence spectrum method is widely applied to the advantages of good selectivity, high efficiency, simple sample pretreatment, no damage to samples, low cost and the like. In recent years, the use of fluorescent probes to detect GSH has received widespread attention. There are two common methods of GSH detection: (1) fluorescence resonance energy transfer is used as a detection platform, a probe is constructed by using two materials, and an energy receptor is consumed or the energy receptor and a donor are separated through the reducibility of GSH or the strong bonding capability of sulfydryl and metal, so that the fluorescence resonance energy transfer process is interrupted, the detection of the glutathione is realized, and the selectivity and the sensitivity of the detection method need to be improved. (2) The strong bonding capability of sulfydryl on the GSH and metal ions is utilized, the metal ions are added to quench the fluorescence of the probe, and then the GSH is added to enable the metal ions to fall off from the surface of the probe, so that the fluorescence of the probe is recovered, and the method is a common method for detecting the GSH at present.
Disclosure of Invention
An object of the present invention is to solve at least the above problems and/or disadvantages and to provide at least the advantages described hereinafter.
One of the purposes of the invention is to provide a preparation method of an 11-mercaptoundecanoic acid modified gold nanocluster, and the prepared gold nanocluster can be used for quantitative detection of glutathione content.
To achieve these objects and other advantages and in accordance with the purpose of the invention, there is provided a method for preparing 11-mercaptoundecanoic acid modified gold nanoclusters, comprising the steps of: dissolving 11-mercaptoundecanoic acid in alkaline ultrapure water, adding HAuCl under stirring4And standing the mixture in the dark for reaction, adding absolute ethyl alcohol, centrifuging and collecting precipitates to obtain the 11-mercaptoundecanoic acid modified gold nanocluster.
Preferably, 11-mercaptoundecanoic acid is reacted with HAuCl4In a molar ratio of 3-4: 1.
Preferably, the reaction time is 4-8h by keeping away from light.
The application of the 11-mercaptoundecanoic acid modified gold nanocluster prepared by the method is used for detecting the content of glutathione.
Preferably, the method for preparing the standard curve for detecting the content of glutathione comprises the following steps: the preparation method of the standard curve for detecting the content of the glutathione comprises the following steps: dispersing gold nanoclusters in ultrapure water to obtain gold nanocluster standby liquid, dispersing the gold nanocluster storage liquid in N-2-hydroxyethylpiperazine-N' -2-ethanesulfonic acid buffer solution to obtain gold nanocluster solution when in use, dividing the gold nanocluster solution into a plurality of parts, adding no copper ions into the first part, and adding Cu with the same content into each of the other parts2+And (3) performing incubation, except for the first part and the second part, adding GSH standard solutions with different gradient volumes into each other part respectively, reacting at room temperature, measuring the fluorescence intensity of the mixed reaction system at 595nm, and obtaining a GSH-recovery rate standard curve by taking the concentration of GSH in the mixed reaction system as an abscissa and the recovery rate of the mixed reaction system as an ordinate.
Preferably, the concentration of the N-2-hydroxyethyl piperazine-N' -2-ethanesulfonic acid buffer solution in the gold nanocluster solution is 10-20 mmol/L.
Preferably, the pH of the N-2-hydroxyethylpiperazine-N' -2-ethanesulfonic acid buffer solution is from 7.0 to 8.0.
Preferably, 8 μ L of 0.1-0.5mmol/L copper ion is added for incubation for 5-10min, and the reaction time is 3-5min at room temperature.
Preferably, the concentration of GSH in the sample to be tested is in the range of 0-12. mu. mol/L.
The invention at least comprises the following beneficial effects:
(1) the invention quenches the fluorescence of the gold nanocluster by the copper ions through charge transfer, enables the copper ions to fall OFF from the surface of the gold nanocluster by utilizing the strong bond and the capability of the copper ions and sulfydryl, recovers the fluorescence of the gold nanocluster, and is an OFF-ON detection mode. The detection model has the advantages of early appearance time, mature application and simple operation, and is applied from early cadmium quantum dots to current carbon dots. The gold nanoclusters with good fluorescence performance, long fluorescence life and simple and rapid synthesis are used as a detection platform, and copper ions are used for regulation and control, so that simple, rapid and sensitive detection of glutathione is realized.
(2) The gold nanocluster used by the invention has good fluorescence performance and long fluorescence life, and has wide application prospect in the field of biomedicine.
(3) Compared with most of the existing GSH detection methods, the method has lower detection limit.
Additional advantages, objects, and features of the invention will be set forth in part in the description which follows and in part will become apparent to those having ordinary skill in the art upon examination of the following or may be learned from practice of the invention.
Drawings
FIG. 1 is a graph showing the fluorescence spectrum, UV-VIS absorption spectrum of 11-mercaptoundecanoic acid modified gold nanoclusters prepared according to the present invention;
FIG. 2 is a transmission electron microscope image of 11-mercaptoundecanoic acid modified gold nanoclusters prepared by the present invention;
FIG. 3 is a diagram showing the distribution of the particle size of 11-mercaptoundecanoic acid modified gold nanoclusters prepared according to the present invention;
FIG. 4 is a graph of gold nanocluster concentration-recovery using different concentration gradients of 11-mercaptoundecanoic acid modified gold nanoclusters;
FIG. 5 is the addition of Cu with different concentration gradients to 11-mercaptoundecanoic acid modified gold nanoclusters2+Cu of (2)2+Concentration-recovery plot;
FIG. 6 is a graph of pH-recovery for 11-mercaptoundecanoic acid modified gold nanoclusters dispersed into hepes of different pH;
FIG. 7 is a bar graph of the recovery at 595nm for 11-mercaptoundecanoic acid modified gold nanoclusters after addition of different amino acids;
FIG. 8 is a graph of the fluorescence recovery of 11-mercaptoundecanoic acid modified gold nanoclusters after addition of GSH at different concentration gradients;
figure 9 is a linear regression plot of GSH concentration versus fluorescence recovery of 11-mercaptoundecanoic acid modified gold nanoclusters at 595nm over a linear range.
Detailed Description
The present invention is further described in detail below with reference to the attached drawings so that those skilled in the art can implement the invention by referring to the description text.
It will be understood that terms such as "having," "including," and "comprising," as used herein, do not preclude the presence or addition of one or more other elements or groups thereof.
Example 1
A preparation method of 11-mercaptoundecanoic acid modified gold nanoclusters comprises the following steps: dissolving 11-mercaptoundecanoic acid in alkaline ultrapure water, adding HAuCl under stirring4And standing the mixture in the dark for reaction, adding absolute ethyl alcohol, centrifuging and collecting precipitates to obtain the 11-mercaptoundecanoic acid modified gold nanocluster.
Example 2
A preparation method of 11-mercaptoundecanoic acid modified gold nanoclusters comprises the following steps: dissolving 11-mercaptoundecanoic acid in alkaline ultrapure water, adding HAuCl under stirring4Adding absolute ethyl alcohol after the reaction of keeping out of the sun and standing, centrifuging and collecting the precipitate to obtain the 11-mercaptoundecanoic acid modified gold nanocluster, wherein the 11-mercaptoundecanoic acid and HAuCl4Is 3: 1.
Example 3
A preparation method of 11-mercaptoundecanoic acid modified gold nanoclusters comprises the following steps: dissolving 11-mercaptoundecanoic acid in alkaline ultrapure water, adding HAuCl under stirring4Adding absolute ethyl alcohol after keeping standing and reacting for 4 hours in the dark, centrifuging and collecting precipitates to obtain the 11-mercaptoundecanoic acid modified gold nanocluster, wherein the 11-mercaptoundecanoic acid and HAuCl4Is 4: 1.
Example 4
A preparation method of 11-mercaptoundecanoic acid modified gold nanoclusters comprises the following steps: dissolving 11-mercaptoundecanoic acid in alkaline ultrapure water, adding HAuCl under stirring4Adding absolute ethyl alcohol after keeping the mixture stand away from light and reacting for 8 hours, and centrifuging and collecting precipitates to obtain the 11-mercaptoundecanoic acid modified gold nanoclusters, wherein the 11-mercaptoundecanoic acid and HAuCl4Is 3: 1.
Example 5
11-mercapto-elevenThe preparation method of the alkanoic acid modified gold nanocluster comprises the following steps: dissolving 26.2mg of 11-mercaptoundecanoic acid in 17mL of ultrapure water having a pH of 12.0; then 3mL of 0.01mol/L HAuCl was added with stirring4Stirring to colorless, standing in dark for 6h, adding anhydrous ethanol, centrifuging to obtain precipitate, dispersing the precipitate in ultrapure water to obtain gold nanocluster stock solution, dispersing the gold nanocluster stock solution in hepes buffer solution with pH of 7.4, measuring fluorescence spectrum and ultraviolet-visible absorption spectrum, and obtaining the result shown in FIG. 1, the transmission electron microscope picture shown in FIG. 2, and the particle size distribution picture shown in FIG. 3.
Test of concentration optimization of 11-mercaptoundecanoic acid-modified gold nanoclusters
Dissolving 26.2mg of 11-mercaptoundecanoic acid in 17mL of ultrapure water having a pH of 12.0; then 3mL of 0.01mol/L HAuCl was added with rapid stirring4Stirring to colorless, standing in dark for 6h, then adding absolute ethanol, centrifuging to obtain precipitate, dispersing the precipitate in ultrapure water to obtain gold nano-cluster stock solution, dispersing the gold nano-cluster stock solution in hepes buffer solution with pH of 7.4 when in use, setting gold nano-clusters with different concentration gradients, adding 10 μ L of 0.3mmol/L copper ions, incubating for 5min, adding 2 μ L of 2.5mmol/L GSH, reacting for 4min, and measuring the fluorescence recovery condition of 595nm, wherein the result is shown in FIG. 4.
Test II Cu2+Concentration optimization
Dissolving 26.2mg of 11-mercaptoundecanoic acid in 17mL of ultrapure water having a pH of 12.0; then 3mL of 0.01mol/L HAuCl was added with rapid stirring4Stirring to be colorless, standing for 6h in a dark place, then adding absolute ethyl alcohol, centrifuging, collecting precipitate, dispersing the precipitate in ultrapure water to obtain a gold nano-cluster stock solution, dispersing the gold nano-cluster stock solution in hepes buffer solution with the pH value of 7.4 when in use, measuring 2mL, adding copper ions with different concentration gradients, incubating for 5min, adding 2 μ L2.5mmol/L GSH, reacting for 4min, and detecting the fluorescence recovery condition of 595nm, wherein the result is shown in figure 5.
Test three pH optimization
Dissolving 26.2mg of 11-mercaptoundecanoic acid in 17mL of ultrapure water having a pH of 12.0; then rapidly stirringThen 3mL of 0.01mol/L HAuCl was added4Stirring to colorless, standing in dark for 6h, adding anhydrous ethanol, centrifuging to obtain precipitate, dispersing the precipitate in ultrapure water to obtain gold nanocluster stock solution, dispersing the gold nanocluster stock solution in hepes buffer solution with pH of 7.4, adjusting pH to 3, 4, 5, 6, 7, 8, 9, 10 and 11, measuring 2mL respectively, adding 8 μ L of 0.3mmol/L copper ions, incubating for 5min, adding 2 μ L of 2.5mmol/L GSH, reacting for 4min, and detecting 595nm fluorescence recovery, the result is shown in FIG. 6.
Test of the selectivity of the tetra-11-mercaptoundecanoic acid-modified gold nanocluster to GSH
Several 2mL hepes dispersions of 11-mercaptoundecanoic acid-modified gold nanoclusters, 6.25. mu.g/mL, were weighed, incubated for 5min with 8. mu.L of 0.3mmol/L copper ions, added with 2. mu.L of 5mmol/L GSH and 2. mu.L of 25mmol/L mono-amino acids of Cys, Ary, Met, Gly, Ala, Phe, Val, Pro, Asn, Lys, Tyr, Trp, Glu, and incubated for 4min before fluorescence measurement. The experimental result is shown in fig. 7, and only after GSH is added, the system has stronger fluorescence recovery, which indicates that other amino acids do not interfere with the detection of the GSH by the 11-mercaptoundecanoic acid-modified gold nanocluster.
Testing the working curve and sensitivity of the penta-11-mercaptoundecanoic acid modified gold nanocluster to GSH detection
Weighing a plurality of 2mL hepes dispersions of 11-mercaptoundecanoic acid modified gold nanoclusters with the concentration of 6.25 mu g/mL, and adding 8 mu L Cu with the concentration of 0.3mmol/L2+After incubation for 5min, 0. mu.L, 1. mu.L, 2. mu.L, 4. mu.L, 6. mu.L, 8. mu.L, 10. mu.L, 12. mu.L, 14. mu.L, 16. mu.L, 18. mu.L, 20. mu.L, 22. mu.L, and 24. mu.L of GSH standard solutions with a concentration of 1mmol/L were added and mixed uniformly to form mixed reaction systems, and after reaction for 4min at room temperature, the fluorescence intensity at 595nm of each mixed reaction system was measured, respectively, and the fluorescence recovery was as shown in FIG. 8. The GSH-fluorescence recovery standard curve is plotted by using the concentration of GSH in each mixed reaction system as the abscissa and the fluorescence recovery at 595nm of each mixed reaction system as the ordinate, as shown in fig. 9.
The method for calculating the recovery rate in the test comprises the following steps:
recovery rate (F-F)1)/F0×100％；
F is the fluorescence intensity of GSH addition, F1To add fluorescence intensity of copper ions, F0Is the fluorescence intensity of the gold nanoclusters.
While embodiments of the invention have been disclosed above, it is not intended to be limited to the uses set forth in the specification and examples. It can be applied to all kinds of fields suitable for the present invention. Additional modifications will readily occur to those skilled in the art. It is therefore intended that the invention not be limited to the exact details and illustrations described and illustrated herein, but fall within the scope of the appended claims and equivalents thereof.
Claims (7)
1. A preparation method of 11-mercaptoundecanoic acid modified gold nanoclusters for detecting glutathione content is characterized by comprising the following steps: dissolving 11-mercaptoundecanoic acid in alkaline ultrapure water, adding HAuCl under stirring4Adding absolute ethyl alcohol after the reaction is kept in a dark place, centrifuging and collecting the precipitate to obtain the 11-mercaptoundecanoic acid modified gold nanocluster; 11-mercaptoundecanoic acid with HAuCl4In a molar ratio of 3-4: 1; standing in dark for 4-8 h.
2. The application of the 11-mercaptoundecanoic acid modified gold nanocluster, which is characterized in that the gold nanocluster prepared by the preparation method of the 11-mercaptoundecanoic acid modified gold nanocluster of claim 1 is used for detecting the content of glutathione.
3. The application of the gold nanoclusters according to claim 2, wherein the method for preparing a standard curve for detecting the content of glutathione comprises the following steps: dispersing gold nanoclusters in ultrapure water to obtain gold nanocluster standby liquid, dispersing the gold nanocluster storage liquid in N-2-hydroxyethylpiperazine-N' -2-ethanesulfonic acid buffer solution to obtain gold nanocluster solution when in use, dividing the gold nanocluster solution into a plurality of parts, adding no copper ions into the first part, and adding Cu with the same content into each of the other parts2+The incubation is carried out in such a way that,adding GSH standard solutions with different gradient volumes into each of the other parts except the first part and the second part, reacting at room temperature, measuring the fluorescence intensity of the mixed reaction system at 595nm, and obtaining a GSH-recovery rate standard curve by taking the concentration of GSH in the mixed reaction system as an abscissa and the recovery rate of the mixed reaction system as an ordinate.
4. The use of gold nanoclusters according to claim 3, wherein the concentration of N-2-hydroxyethylpiperazine-N' -2-ethanesulfonic acid buffer in the gold nanocluster solution is 10-20 mmol/L.
5. The use of gold nanoclusters according to claim 3, wherein the pH of the N-2-hydroxyethylpiperazine-N' -2-ethanesulfonic acid buffer solution is 7.0 to 8.0.
6. The use of gold nanoclusters according to claim 3, wherein 8 μ L of 0.1-1.5mmol/L copper ions are added for incubation for 5-10min, and the reaction time at room temperature is 3-5 min.
7. The use of gold nanoclusters according to claim 3, wherein the concentration of GSH in the sample to be tested is in the range of 0-12 μmol/L.
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