CN114907840B - Fluorescent gold nanocluster for monitoring intracellular GSH concentration and preparation method thereof - Google Patents
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Abstract
The invention discloses a fluorescent gold nanocluster for monitoring GSH concentration in cells and a preparation method thereof, wherein the preparation method of the fluorescent gold nanocluster comprises the following steps: and (3) mixing the micromolecular thiol ligand with chloroauric acid in a methanol aqueous solution for reaction, and performing ultrafiltration after the reaction to obtain the fluorogold nanocluster for monitoring the intracellular GSH concentration. The invention synthesizes water-soluble nanoclusters with accurate atoms for qualitative detection of GSH in cells for the first time, and provides a novel nano material for detecting GSH; the fluorescent gold nanocluster can selectively react with GSH, is not interfered by other substances in organisms, and has an extremely low detection limit of 13 mu M for GSH.
Description
Technical Field
The invention relates to the technical field of nanoclusters, in particular to a fluorescent gold nanocluster for monitoring intracellular GSH concentration and a preparation method thereof.
Background
Currently, GSH is detected by gold nanoclusters by connecting groups to peripheral ligands of the clusters to achieve functionalization of the cluster surfaces. However, this method results in an increase in the size of the water-soluble clusters, and thus is not easily metabolized by the human body. In addition, it is reported in the literature that functionalized clusters are typically above 10nm in size, and larger size clusters can also cause clusters to aggregate within cells, thereby affecting the detection results.
Disclosure of Invention
Based on the technical problems in the background technology, the invention provides the fluorescent gold nanocluster for monitoring the intracellular GSH concentration and the preparation method thereof, and the fluorescent gold nanocluster has the advantages of intracellular detection, low detection limit and the like.
The invention provides a preparation method of a fluorogold nanocluster for monitoring GSH concentration in cells, which comprises the following steps: and (3) mixing the micromolecular thiol ligand with chloroauric acid in a methanol aqueous solution for reaction, and performing ultrafiltration after the reaction to obtain the fluorogold nanocluster for monitoring the intracellular GSH concentration.
Preferably, the small molecule thiol is a purine thiol, a folic acid thiol or a pyrimidine thiol.
Preferably, the small molecule thiol is 6-thioguanine.
Preferably, the molar ratio of the 6-thioguanine to the chloroauric acid is 1:20-40.
Preferably, the volume ratio of water to methanol in the aqueous methanol solution is 1:2-6.
Preferably, the reaction temperature is 20-50℃and the reaction time is 5-48 hours.
The fluorescent gold nanocluster for monitoring the intracellular GSH concentration, which is prepared by the method, is provided by the invention.
Preferably, the molecular formula of the fluorescent gold nanocluster is Au m (SR) n Wherein SR is a ligand.
Preferably, m=21 and n=16 in the molecular formula of the fluorogold nanocluster.
The invention provides application of the fluorescent gold nanocluster in detecting intracellular GSH concentration.
The beneficial technical effects of the invention are as follows:
(1) The invention synthesizes water-soluble nanoclusters with accurate atoms for qualitative detection of GSH in cells for the first time, and provides a novel nano material for detecting GSH.
(2) The fluorescent gold nanocluster synthesized by the invention can selectively react with GSH and is not interfered by other substances in organisms.
(3) The size of the fluorescent gold nanocluster synthesized by the invention is only about 1nm, thereby effectively avoiding the aggregation of the nanocluster in cells and being easier to be metabolized by human bodies.
(4) The synthesized fluorescent water-soluble nanoclusters of the present invention have an extremely low detection limit of 13 μm for GSH.
Drawings
FIG. 1 is a mass spectrum of a fluorescent gold nanocluster according to the present invention;
FIG. 2 is a graph of DLS detection results of fluorogold nanoclusters according to the present invention;
FIG. 3 is a graph showing GSH effect of the specific detection of the fluorogold nanoclusters according to the present invention;
FIG. 4 is a GSH titration diagram of a fluorogold nanocluster according to the present invention;
FIG. 5 is a schematic diagram of monitoring intracellular GSH of a fluorogold nanocluster according to the present invention.
Detailed Description
Example 1
A preparation method of a fluorescent gold nanocluster for monitoring intracellular GSH concentration comprises the following steps: uniformly mixing chloroauric acid and 6-thioguanine in a mixed solvent of water and methanol at room temperature, and ultrafiltering with a 3kDa ultrafiltration tube after reaction to finally obtain the purified fluorogold nanocluster.
Wherein: the mol ratio of chloroauric acid to 6-thioguanine is 1:40, and the volume ratio of water to methanol is 1:6; the reaction temperature was 35℃and the reaction time was 24 hours.
Example 2
A preparation method of a fluorescent gold nanocluster for monitoring intracellular GSH concentration comprises the following steps: uniformly mixing chloroauric acid and 6-thioguanine in a mixed solvent of water and methanol at room temperature, and ultrafiltering with a 3kDa ultrafiltration tube after reaction to finally obtain the purified fluorogold nanocluster.
Wherein: the mol ratio of chloroauric acid to 6-thioguanine is 1:20, and the volume ratio of water to methanol is 1:2; the reaction temperature was 20℃and the reaction time was 5 hours.
Example 3
A preparation method of a fluorescent gold nanocluster for monitoring intracellular GSH concentration comprises the following steps: uniformly mixing chloroauric acid and 6-thioguanine in a mixed solvent of water and methanol at room temperature, and ultrafiltering with a 3kDa ultrafiltration tube after reaction to finally obtain the purified fluorogold nanocluster.
Wherein: the mol ratio of chloroauric acid to 6-thioguanine is 1:30, and the volume ratio of water to methanol is 1:4; the reaction temperature was 50℃and the reaction time was 48h.
Taking the fluorogold nanocluster for monitoring intracellular GSH concentration prepared in example 1 and application thereof as an example, a related performance test was performed, wherein:
to detect the selectivity of fluorogold nanoclusters and explore their potential application in cell sensing, we studied the effect of foreign ions. Selecting biomolecules such as L-histidine (L-His), cysteine (Cys), glycine (Gly), leucine (Leu), glutamic acid (Glu), lysine (Lys), histidine (His) and arginine (Arg), cationic Zn 2+ ，K + ，Na + ，Cu 2+ ，Mg 2+ ，Fe 2+ ，Fe 3+ ，Cu + As a control experiment, the concentration of the fluorescent gold nanocluster is 2 mu mol/L (equal to GSH), and the selectivity of the fluorescent gold nanocluster to GSH is compared, so that the result shows that the fluorescent gold nanocluster can realize high-selectivity detection of GSH.
To investigate the sensitivity of fluorescent nanoclusters to GSH, we mixed them with different concentrations of GSH. As GSH concentration increases from 0 to 12. Mu. Mol/L, the fluorescence intensity of nanoclusters gradually decreases. As GSH content increases, the quenching effect gradually increases. Further, as shown in fig. 4, the detection Limit (LOD) of GSH was 13 μmol/L at 0-5 μΜ, according to the detection limit=3σ/s.
FIG. 1 is a mass spectrum of a fluorogold nanocluster, 2mL,1.5mmol/L anticancer nanocluster was purified by a 3kDa ultrafiltration tube, and purified by a high resolution mass spectrometer (Waters Q-TOF precursor, available in negative ion modeMass spectrometry from vortical corporation in united states) and its molecular formula was simulated, it was found from fig. 1 that the fluorescent nanocluster cluster had two sets of peaks at 1381Da and 1726Da, simulated by Isopro software, and the small inset in fig. 1 demonstrated that the theoretical peak was quite identical to the experimental peak, and the molecular formula of the nanocluster was Au 21 (SR) 16 (sr=ligand), valence number n=m-N-q=21-16+1=6. Thus, ESI-MS also demonstrated that the prepared fluorophore had a 6e structure.
Fig. 2 is a size diagram of a fluorescent gold nanocluster, 2mL of the purified solution is taken, and the size of the fluorescent gold nanocluster is measured by using a DLS (laser particle sizer, model ZS90, manufacturer malvern), and as can be seen from fig. 2, the size of the fluorescent gold nanocluster prepared by the method is only about 1nm, which is far smaller than the size (more than 10 nm) of the existing functionalized fluorescent gold nanocluster, so that aggregation of the clusters in cells is effectively avoided, and the clusters are more easily metabolized by a human body.
FIG. 3 is a graph showing the effect of detecting GSH by specificity of fluorogold nanoclusters, and the specific test method comprises the following steps: preparing L-histidine (L-His), cysteine (Cys), glycine (Gly), leucine (Leu), glutamic acid (Glu), lysine (Lys), histidine (His) and arginine (Arg) with concentration of 2 mu mol/L, and cation Zn 2+ ，K + ，Na + ，Cu 2+ ，Mg 2+ ，Fe 2+ ，Fe 3+ ，Cu + 2. Mu.L of the solution was added to 100. Mu.L of gold nanoclusters, respectively, and the emission intensity was measured in a fluorescence detector.
Fig. 4 is a titration diagram of GSH detection by fluorogold nanoclusters, and the specific test method is as follows: GSH was formulated at a concentration of 1. Mu. Mol/L to be added to 100. Mu.L of gold nanoclusters and the emission intensity was tested in a fluorescence detector.
FIG. 5 is a graph showing the effect of detecting GSH in a fluorescent gold nanocluster cell, and the specific test method is as follows: cancer cells Hela cells were incubated overnight in 96-well plates. The old medium was discarded, gold nanoclusters were added at a concentration of 20. Mu.g/mL, GSH 0. Mu.L, 4. Mu.L, 8. Mu.L, 12. Mu.L at a concentration of 1. Mu.mol/L were added after 2 hours, and a fluorescence photograph was taken with a laser confocal microscope.
The foregoing description of the preferred embodiments of the invention is not intended to be limiting, but rather is intended to cover all modifications, equivalents, alternatives, and improvements that fall within the spirit and scope of the invention.
Claims (4)
1. The preparation method of the fluorogold nanocluster for monitoring the GSH concentration in cells is characterized by comprising the following steps: mixing micromolecular mercaptan ligand and chloroauric acid in methanol aqueous solution for reaction, and ultrafiltering after the reaction to prepare a fluorogold nanocluster for monitoring the intracellular GSH concentration;
the small molecule thiol ligand is 6-thioguanine;
the molar ratio of the small molecule thiol ligand to the chloroauric acid is 1:20-40;
the volume ratio of water to methanol in the methanol aqueous solution is 1:2-6;
the reaction temperature is 20-50 ℃ and the reaction time is 5-48h.
2. A fluorogold nanocluster for monitoring intracellular GSH concentration prepared by the method of claim 1.
3. The fluorogold nanocluster for monitoring intracellular GSH concentration according to claim 2, wherein the fluorogold nanocluster has a molecular formula of Au 21 （SR） 16 Wherein SR is a ligand.
4. Use of a fluorogold nanocluster according to claim 2 or 3 for monitoring intracellular GSH concentration.
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Citations (5)
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| CN104101584A (en) * | 2014-06-12 | 2014-10-15 | 东南大学 | Application of gold nanocluster as glutathione fluorescent probe |
| CN104749151A (en) * | 2015-04-08 | 2015-07-01 | 东南大学 | Application of glutathione-based stable gold nano cluster particles to detection of sulfhydryl compound |
| CN109705841A (en) * | 2018-12-24 | 2019-05-03 | 山西大学 | A kind of transferrins is the gold nano cluster and its preparation method and application of template |
| CN111269715A (en) * | 2020-02-13 | 2020-06-12 | 中国科学院合肥物质科学研究院 | Ratiometric fluorescent probe and application thereof in visual detection of glutathione |
| CN113663072A (en) * | 2021-06-29 | 2021-11-19 | 安徽大学 | Anti-cancer cluster targeting cell lysosome and preparation method thereof |
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| TWI361081B (en) * | 2008-08-29 | 2012-04-01 | Univ Chung Yuan Christian | Fluorescent gold nanocluster and method for forming the same |
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104101584A (en) * | 2014-06-12 | 2014-10-15 | 东南大学 | Application of gold nanocluster as glutathione fluorescent probe |
| CN104749151A (en) * | 2015-04-08 | 2015-07-01 | 东南大学 | Application of glutathione-based stable gold nano cluster particles to detection of sulfhydryl compound |
| CN109705841A (en) * | 2018-12-24 | 2019-05-03 | 山西大学 | A kind of transferrins is the gold nano cluster and its preparation method and application of template |
| CN111269715A (en) * | 2020-02-13 | 2020-06-12 | 中国科学院合肥物质科学研究院 | Ratiometric fluorescent probe and application thereof in visual detection of glutathione |
| CN113663072A (en) * | 2021-06-29 | 2021-11-19 | 安徽大学 | Anti-cancer cluster targeting cell lysosome and preparation method thereof |
Non-Patent Citations (2)
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| Xin Yi Wong et al..Integrating gold nanoclusters, folic acid and reduced graphene oxide for nanosensing of glutathione based on "turn‑off" fluorescence.Scientific Reports.2021,第11卷第2375页. * |
| Yuanqing Sun et al..Tunable near-infrared fluorescent gold nanoclusters: temperature sensor and targeted bioimaging.New J. Chem..2017,第41卷第5412-5419页. * |
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