CN113618059A - Tryptophan-terminated silver nanocluster fluorescent probe and preparation method and application thereof - Google Patents
Tryptophan-terminated silver nanocluster fluorescent probe and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a tryptophan end-capped silver nanocluster fluorescent probe and a preparation method and application thereof. The preparation method of the tryptophan end-capped silver nanocluster comprises the following steps: to be provided withDTryptophan is used as a reducing agent and a protective agent, and the silver nanocluster capped by the tryptophan is rapidly prepared by using microwave assistance. The process does not need to add other reducing agents, and has the advantages of simple reaction conditions, short reaction time and environmental friendliness. Silver nanoparticles prepared by the inventionThe nanocluster fluorescent probe has high selectivity and sensitivity for detecting copper ions. In addition, since silver nanoclusters have low toxicity and good biocompatibility, they can also be applied to bioimaging in living cells.
Description
Technical Field
The invention relates to the technical field of detection and cell imaging, in particular to a preparation method of a tryptophan end-capped silver nano-cluster fluorescent probe and application of the tryptophan end-capped silver nano-cluster fluorescent probe in analysis detection and cell imaging.
Background
Metal Nanoclusters (NCs) have become a new class of nanomaterials with a wide range of applications, particularly in the areas of biosensing, bioimaging, therapeutic applications, and catalysis, with increasing attention. They lie between the metallic nanoparticle and atomic dimensions and therefore exhibit a discrete electronic structure, resulting in unique physical and chemical properties. Among them, silver nanoclusters (Ag NCs) exhibit better photostability, chemical stability, and low cytotoxicity. In addition, Ag NCs are attractive fluorescent probes for luminescence-based sensing and bioimaging due to their ultra-fine size, good biocompatibility and long luminescence lifetime. However, the traditional synthesis method of Ag NCs is complex, needs additional reducing agents and has long preparation time. Such resources and time consuming synthesis processes limit their further applications. At the same time, they irreversibly aggregate due to their high surface energy. Therefore, development of a method for preparing fluorescent Ag NCs that are green, rapid, and highly stable is urgently required.
Copper plays an important role in animals and plants as an essential micronutrient for organisms. However, excessive copper (cu (ii)) ions are harmful to human health and can disrupt cellular metabolic processes, leading to a range of diseases such as kidney/liver damage and nervous system damage. On the other hand, the modern society causes more and more serious copper pollution in the environment due to the unreasonable discharge of the sewage containing Cu (II). Therefore, it is clearly very necessary to have available a cost-effective, rapid and sensitive new and efficient cu (ii) detection method. The fluorescent probe has the advantages of simple operation, rapid analysis, low cost and the like, and becomes an attractive detection method for Cu (II) detection. At the same time, optical imaging probes with low cytotoxicity and high biocompatibility are also becoming increasingly important for the study of in vivo nano-diagnostics and imaging. Therefore, the tryptophan-terminated silver nanocluster can be used as a promising multifunctional fluorescent probe for Cu (II) sensing and cell imaging.
Disclosure of Invention
The invention aims to solve the problems and provides a microwave-assisted green and rapid fluorescence nano-cluster probe for measuring Cu (II), which has the advantages of high response speed (1 min), wide linear range and low limit of detection (LOD). Meanwhile, exhibits excellent biocompatibility and low cytotoxicity, and has been successfully applied to cell imaging.
In order to achieve the technical purpose, the invention adopts the following technical scheme: the first purpose of the invention is to provide a tryptophan end-capped silver nanocluster, wherein tryptophan is used as a reducing agent and a protective agent, silver nitrate is used as a metal source, the silver nanocluster is rapidly prepared by a microwave-assisted method, the particle size distribution of the silver nanocluster is about 3nm-6nm, the average particle size of the silver nanocluster is 4.3nm, and blue fluorescence is displayed at 450nm when the silver nanocluster is excited at an excitation wavelength of 374 nm.
The second purpose of the invention is to provide a preparation method of the tryptophan end-capped silver nanocluster, which comprises the following steps:
(1) adopting a microwave-assisted heating method, wherein the silver nitrate and the tryptophan AgNO are3The molar ratio of/Trp is 1:1-1:40, by silver nitrate AgNO3AndD-tryptophanD-Trp mixed reaction to prepare silver nanocluster Trp-Ag NCs, wherein the microwave power is 180-900W, and the reaction time is 5-35 min;
(2) and (3) performing purification treatment on the step (1), centrifuging the silver nano cluster dispersion liquid at 10000rpm for 10min to remove large particles, dialyzing for 24h by using a 500-Da dialysis bag, and freeze-drying for 48h at-40 ℃ to obtain the tryptophan end-capped silver nano cluster of brown yellow powder.
Further, in the step (1), the silver nitrate and tryptophan AgNO are3Mole of/TrpThe molar ratio is 1: 2.
Further, in the step (1), the microwave power of the reaction is 540W.
Further, in the step (1), the reaction time is 30 min.
The third purpose of the invention is to provide the tryptophan end-capped silver nanocluster fluorescent probe.
The fourth purpose of the invention is to provide a method for detecting Cu (II) by utilizing the tryptophan-terminated silver nanoclusters.
A fifth object of the present invention is to provide a cell imaging agent as a good bio-imaging ability in HeLa cells using tryptophan-terminated silver nanoclusters.
Has the advantages that: according to the invention, the tryptophan end-capped silver nanocluster is rapidly prepared through green microwave radiation, and shows strong blue luminescence, long fluorescence life and excellent stability. For the highly selective and sensitive detection of Cu (II). In addition, the silver nanoclusters may be well applied to cell imaging due to excellent biocompatibility.
Compared with the prior art, the invention has the following advantages:
(1) the silver nanocluster fluorescent probe prepared by the invention has high selectivity and sensitivity for detecting copper ions, no other reducing agent is required to be added in the preparation process, the reaction condition is simple, the reaction time is short, and the method is environment-friendly.
(2) The invention prepares the tryptophan end-capped silver nanocluster by a green microwave-assisted method. The silver nanoclusters prepared by the method disclosed by the invention show excellent photoluminescence characteristics and have high light stability, time stability and metal stability.
(3) The silver nanocluster prepared by the method can be used for detecting Cu (II) with high selectivity and sensitivity. The linear range is wide, and the detection limit LOD is low.
(4) The silver nano cluster prepared by the method has low toxicity and good biocompatibility, and can be used as potential application of biological imaging in living cells.
Drawings
FIG. 1(a) is a transmission electron microscope image of a silver nanocluster fluorescent probe prepared in test example 1 of the present invention, and the inset is a particle size distribution diagram of the silver nanocluster; (b) ultraviolet absorption spectrum, excitation spectrum and emission spectrum of the prepared silver nanoclusters prepared in example 1 of the present invention;
FIG. 2 is a linear fluorescence diagram of silver nanoclusters prepared in Experimental example 1 of the present invention for detecting Cu (II) at different concentrations;
FIG. 3 shows the selectivity and anti-interference performance of silver nanocluster fluorescent probe prepared in test example 1 of the present invention for different anions and cations;
FIG. 4 is a diagram showing a cell image of HeLa cells using silver nanocluster fluorescent probe prepared in test example 1 of the present invention, (a) using 405nm excitation wavelength, and (b) using 488nm excitation wavelength;
FIG. 5 is a cytotoxicity test of the silver nanocluster fluorescent probe prepared in test example 1 of the present invention.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail below with reference to the accompanying drawings and embodiments, but the scope of the present invention is not limited to these embodiments.
Example 1
According to the tryptophan end-capped silver nanocluster, tryptophan is used as a reducing agent and a protective agent, silver nitrate is used as a metal source, the silver nanocluster is rapidly prepared by a microwave-assisted method, the particle size distribution of the silver nanocluster is about 3nm-6nm, the average particle size is 4.3nm, the silver nanocluster is excited at an excitation wavelength of 374nm, and blue fluorescence is displayed at a position of 450 nm.
The preparation method of the tryptophan end-capped silver nanocluster comprises the following steps: (1) adopting a microwave-assisted heating method, wherein the silver nitrate and the tryptophan AgNO are3The molar ratio of/Trp is 1:1, and the silver nitrate AgNO is added3AndD-tryptophanD-Trp mixed reaction to prepare silver nanocluster Trp-Ag NCs; the microwave power of the reaction is 900W, and the reaction time is 29 min.
(2) And (3) performing purification treatment on the step (1), centrifuging the silver nano cluster dispersion liquid at 10000rpm for 10min to remove large particles, dialyzing for 24h by using a 500-Da dialysis bag, and freeze-drying for 48h at-40 ℃ to obtain the tryptophan end-capped silver nano cluster of brown yellow powder.
The tryptophan end-capped silver nanocluster fluorescent probe is disclosed by the invention.
The silver nanocluster blocked by tryptophan is used for detecting Cu (II).
The silver nanocluster capped by tryptophan is used as a cell imaging agent with good biological imaging capacity in HeLa cells.
Example 2
According to the tryptophan end-capped silver nanocluster, tryptophan is used as a reducing agent and a protective agent, silver nitrate is used as a metal source, the silver nanocluster is rapidly prepared by a microwave-assisted method, the particle size distribution of the silver nanocluster is about 3nm-6nm, the average particle size is 4.3nm, the silver nanocluster is excited at an excitation wavelength of 374nm, and blue fluorescence is displayed at a position of 450 nm.
The preparation method of the tryptophan end-capped silver nanocluster comprises the following steps: in the step (1), a microwave-assisted heating method is adopted, and the silver nitrate and the tryptophan AgNO are3The molar ratio/Trp is 1:40, by silver nitrate AgNO3AndD-tryptophanD-Trp mixed reaction to prepare silver nanocluster Trp-Ag NCs; the microwave power of the reaction is 180W, and the reaction time is 35 min.
In the step (2), the purification treatment is carried out on the step (1), the silver nano cluster dispersion liquid is centrifuged for 10min at 10000rpm to remove large particles, dialyzed for 24h by using a dialysis bag of 500-1000Da, and freeze-dried for 48h at-40 ℃ to obtain the tryptophan end-capped silver nano cluster of brown yellow powder.
Example 3
The particle size distribution of the silver nanoclusters is about 3-6nm, and the average particle size of the silver nanoclusters is 4.3 nm.
The preparation method of the tryptophan end-capped silver nanocluster comprises the following steps: in the step (1), a microwave-assisted heating method is adopted, and the silver nitrate and the tryptophan AgNO are3The molar ratio of/Trp is1:2 by silver nitrate AgNO3AndD-tryptophanD-Trp mixed reaction to prepare silver nanocluster Trp-Ag NCs; the microwave power of the reaction is 540W, and the reaction time is 5 min.
In the step (2), the purification treatment is carried out on the step (1), the silver nano cluster dispersion liquid is centrifuged for 10min at 10000rpm to remove large particles, dialyzed for 24h by using a dialysis bag of 500-1000Da, and freeze-dried for 48h at-40 ℃ to obtain the tryptophan end-capped silver nano cluster of brown yellow powder.
Test example 1
(1) Experimental apparatus and model:
the morphology was obtained by a transmission electron microscope (JEM-2100 plus, Japan Electron Co., Ltd.); the particle size distribution was recorded by a particle size analyzer (malvern Nano ZS90, uk); the fluorescence spectrum was measured by a fluorescence spectrophotometer (Hitachi F-7000, Japan); cell imaging was obtained by laser confocal microscopy (leicas sp5, germany); cytotoxicity assays were measured by a microplate reader (molecular leica SP5, usa).
(2) Preparing a silver nanocluster probe:
2mL of 0.02M Trp and 200. mu.L of 0.1MAGNO3Mixing in a beaker, and heating with microwave for 30min at 540W. After the reaction is completed, the reaction product is cooled to room temperature, and 10mL of deionized water is used for dissolving the product and ultrasonic treatment is carried out for 10 min. Centrifuging at 10000rpm for 10min, dialyzing with 500-1000Da for 24h, freeze-drying at-40 deg.C for 48h to obtain brown yellow powder of tryptophan terminated silver nanocluster, and storing in a refrigerator at 4 deg.C for use.
The method is characterized in that a microwave-assisted method is utilized to rapidly prepare silver nanoclusters, the silver nanoclusters are quasi-spherical, small particles with uniform dispersion and uniform size are distributed between 3nm and 6nm in particle size, and the average particle size is 4.3nm (shown in figure 1 a).
Dissolving the prepared silver nanocluster powder in water, wherein the concentration is 100 mu g/mL, applying the silver nanocluster powder to an ultraviolet spectrophotometer, and enabling an absorption peak of maximum absorption to appear at 356 nm; the fluorescence spectrophotometer measured the maximum excitation and emission wavelengths, which were 374nm and 450nm, respectively (FIG. 1 b).
Test example 2
The experimental procedure for the determination of Cu (II) is as follows: stock solutions (10mM, 1mM, 0.1mM, and 0.01mM) were prepared at different concentrations of Cu (II) by deionized water. To a stock of 1mL Trp-Ag NCs (100 μ g/mL), 2mL of standard buffer solution (50mM, pH 4) was added, and cu (ii) solutions of different concentrations were added to the mixed solution. After 1 minute of incubation, emission fluorescence spectra were collected at 450nm in a quartz cuvette at an excitation wavelength of 374nm, and a linear relationship was established between Δ F fluorescence intensity and cu (ii) concentration (fig. 2), indicating a wide linear range and a low detection limit.
Test example 3
The selectivity and interference immunity of the fluorescent sensor was also evaluated, with different cations (20. mu.M) (Cu)2+,K+,Na+,Ag+,Hg2+,Mg2+,Mg2+,Cd2+,Ni2+,Ca2+,Mn2+,Pb2+,Fe2+,Zn2+,Fe3+,Al3+And Co3+) And anions (Cl)-,Br-,I-,NO3 -,CO3 2-,SO4 2-And PO4 3-) The resulting mixture was added to 3mL of Trp-Ag NCs to examine the selectivity. At the same time, 20 μ M Cu was added2+Added to Trp-Ag NCs solution together with 100. mu.M of the above ions to evaluate whether other ions are Cu-pairing2+The results show that the silver nanoclusters have better selectivity and interference resistance.
Test example 4
Cell imaging experiments of silver nanoclusters: HeLa cells in DMEM medium (density approximately 2X10 per well)4Individual cells) at 37 ℃ and 5% CO2And culturing for 48 hours. After incubation for 2h with 100. mu.L Trp-Ag NCs (100. mu.g/mL), the cells were washed 3 times with phosphate buffered saline (PBS buffer). Finally, cellular imaging was obtained by confocal laser fluorescence microscopy at 405 and 488nm excitation (fig. 4 a-b).
Test example 5
And (3) testing cytotoxicity of the silver nanocluster: 8x10 per hole3The HeLa cells were cultured overnight in 96-well plates, and 100. mu.L of each was addedTrp-Ag NCs were added to DMEM medium at a concentration of 5% CO at 37 deg.C2And culturing for 24 hours. The medium was changed to 110 μ L of mixed solution (100 μ L of EMEM medium containing 10% Fetal Bovine Serum (FBS) and 10 μ L of CCK-8 reagent, incubated for 2h, followed by washing of PBS buffer and detection of absorbance at 450nm by microplate reader.) the results showed that silver nanoclusters had low toxicity and high biocompatibility (fig. 5).
The foregoing shows and describes the general principles, essential features, and advantages of the invention. It will be understood by those skilled in the art that the present invention is not limited to the embodiments described above, which are described in the foregoing description only for the purpose of illustrating the principles of the present invention, but that various changes and modifications may be made therein without departing from the spirit and scope of the invention as defined by the appended claims, specification, and equivalents thereof.
Claims (9)
1. A tryptophan-terminated silver nanocluster, comprising: tryptophan is used as a reducing agent and a protective agent, silver nitrate is used as a metal source, a microwave-assisted method is utilized to rapidly prepare silver nanoclusters, the particle size distribution of the silver nanoclusters is about 3nm-6nm, the average particle size of the silver nanoclusters is 4.3nm, and the silver nanoclusters are excited at an excitation wavelength of 374nm and show blue fluorescence at a wavelength of 450 nm.
2. The method of preparing tryptophan end-capped silver nanoclusters as recited in claim 1, comprising the steps of:
(1) adopting a microwave-assisted heating method, wherein the silver nitrate and the tryptophan AgNO are3The molar ratio of/Trp is 1:1-1:40, and the synthesis is carried out by silver nitrate AgNO3AndD-tryptophanDPreparing silver nanocluster Trp-Ag NCs through Trp mixed reaction, wherein the microwave power is 180-900W, and the reaction time is 5-35 min;
(2) and (3) performing purification treatment on the step (1), centrifuging the silver nano cluster dispersion liquid at 10000rpm for 10min to remove large particles, dialyzing for 24h by using a 500-Da dialysis bag, and further performing freeze drying at-40 ℃ for 48h to obtain the brown yellow powder tryptophan end-capped silver nano cluster.
3. The method of preparing tryptophan-terminated silver nanoclusters according to claim 2, wherein: in the step (1), the silver nitrate and the tryptophan AgNO are3The molar ratio of/Trp is 1: 2.
4. The method of preparing tryptophan-terminated silver nanoclusters according to claim 3, wherein: in the step (1), the microwave power of the reaction is 540W.
5. The method of preparing tryptophan-terminated silver nanoclusters according to claim 2, wherein: in the step (1), the reaction time is 30 min.
6. The tryptophan end-capped fluorescent probe for silver nanoclusters of any one of claims 1 to 5.
7. Use of the tryptophan end-capped silver nanocluster fluorescent probe of any one of claims 1 to 5 for detecting Cu (II).
8. Use of the tryptophan-terminated silver nanocluster fluorescent probe as recited in any one of claims 1 to 5 in a cell imaging agent having good biological imaging capability.
9. Use according to claim 8, characterized in that: the tryptophan end-capped silver nanocluster fluorescent probe is applied to the preparation of HeLa cell imaging.
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