CN115728281A - Fluorescent probe for detecting L-tryptophan and preparation thereof - Google Patents
Fluorescent probe for detecting L-tryptophan and preparation thereof Download PDFInfo
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- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
Abstract
The invention belongs to the technical field of fluorescence analysis, and particularly relates to a fluorescent probe for detecting L-tryptophan and preparation thereof. Dissolving beta-cyclodextrin in NaOH solution, adding sublimed sulfur powder and ultrapure water, and heating and dialyzing to obtain the beta-cyclodextrin sulfur quantum dot. The invention takes beta-cyclodextrin sulfur quantum dots as fluorescent probes, can carry out quantitative detection on L-tryptophan, has a linear range of 50-500nmol/L and a detection limit of 9.3nmol/L. The sensing system has high sensitivity and good selectivity, can be used for detecting and determining L-tryptophan in an amino acid injection of an actual sample, and has good clinical application prospect.
Description
Technical Field
The invention belongs to the technical field of fluorescence analysis, and particularly relates to a fluorescent probe for detecting L-tryptophan and preparation thereof.
Background
The luminescent quantum dots have unique characteristics of size dependence, magnetism, optics, electrochemistry and the like, and compared with the toxicity and potential environmental hazard of other quantum dots containing heavy metals, the luminescent quantum dots mainly aim to find nontoxic non-heavy metal quantum dots, wherein the sulfur quantum dots are paid much attention due to good chemical stability, water dispersibility and biocompatibility.
L-tryptophan is an essential component of protein synthesis and is an aromatic amino acid required for growth and metabolism in animals and humans. Deficiency of L-tryptophan results in cataract, diabetes, depression, etc., and L-tryptophan is not synthesized in vivo and needs to be obtained by diet or supplementation. Therefore, the analytical detection of L-tryptophan is of great significance in pharmaceutical, environmental, clinical and industrial research. The fluorescent probe is a novel detection reagent, and is favored by people due to the advantages of higher sensitivity, lower detection cost, simple sample treatment, convenient operation, quick determination and real-time detection. However, no report has been made so far on the use of sulfur quantum dots as fluorescent probes for L-tryptophan detection.
Disclosure of Invention
Based on the background, the invention provides a fluorescent probe for detecting L-tryptophan and a preparation method thereof. The invention utilizes the sulfur quantum dots to construct the fluorescent probe, and constructs a linear relation curve by a fluorescence analysis method, thereby realizing the quantitative detection of the L-tryptophan. The method has the advantages of low cost, high sensitivity, good linear relation, simple and easy operation and good selectivity, can be used for quantitative detection of L-tryptophan in the amino acid injection, and has good clinical application prospect.
In order to realize the purpose, the invention is realized by the following technical scheme:
the invention provides a fluorescent probe for detecting L-tryptophan, which is a beta-cyclodextrin sulfur quantum dot.
Further, the preparation method of the beta-cyclodextrin sulfur quantum dot comprises the following steps: dissolving beta-cyclodextrin in NaOH solution, adding sublimed sulfur powder and ultrapure water, and carrying out heating and dialysis treatment to obtain the beta-cyclodextrin sulfur quantum dot.
Further, the concentration of the NaOH solution is 1.8-2.0mol/L.
Further, the mass ratio of the beta-cyclodextrin to the sublimed sulfur powder is 3:1-2.5.
Further, the heating mode is oil bath heating.
Furthermore, the heating time is 120-144h, and the temperature is 60-80 ℃.
Further, the specific process of dialysis is as follows: dialyzing in a dialysis bag with molecular weight cutoff of 3500Da for 12-24h.
The invention also provides application of the fluorescent probe in L-tryptophan detection.
Further, the method is applied to detection and determination of L-tryptophan in amino acid injection.
Further, adding beta-cyclodextrin sulfur quantum dots into the solution to be detected, adding a Tris-HCl buffer solution, and performing fluorescence spectrometry at a fixed excitation wavelength of 340 nm.
Compared with the prior art, the invention has the following beneficial effects:
(1) The method takes the cheap sulfur powder as a sulfur source and the beta-cyclodextrin as an etching agent, synthesizes the beta-cyclodextrin sulfur quantum dots by a one-pot method, and has simple operation, greenness and no pollution in the preparation process.
(2) The beta-cyclodextrin sulfur quantum dot prepared by the invention has good fluorescence performance and light stability as a fluorescent probe, has the strongest fluorescence intensity at the wavelength of 420nm when the excitation wavelength is 312nm, and has good peak shape of a fluorescence emission peak.
(3) The invention provides a novel method for quickly detecting L-tryptophan with high sensitivity and high selectivity. When the beta-cyclodextrin sulfur quantum dots are applied to L-tryptophan detection, the fluorescence emission of the beta-cyclodextrin sulfur quantum dots at the position of 420nm can be obviously enhanced, because the L-tryptophan and the beta-cyclodextrin sulfur quantum dots form a stable inclusion compound, and when the L-tryptophan and the beta-cyclodextrin sulfur quantum dots coexist, the fluorescence of the sulfur quantum dots can be obviously enhanced. Based on the method, the beta-cyclodextrin sulfur quantum dots can realize quantitative detection of L-tryptophan, the linear range is 50-500nmol/L, and the detection limit is 9.3nmol/L.
Drawings
FIG. 1 is an infrared spectrum of beta-cyclodextrin sulfur quantum dots.
FIG. 2 is a fluorescence excitation and emission spectrum of beta-cyclodextrin sulfur quantum dots.
FIG. 3 is a graph of the effect of pH on the stability of beta-cyclodextrin sulfur quantum dots.
FIG. 4 is a graph of the effect of ionic strength on the stability of beta-cyclodextrin sulfur quantum dots.
FIG. 5 shows the high selectivity of beta-cyclodextrin sulfur quantum dot detection of L-tryptophan.
FIG. 6 is a graph showing the linear relationship between the concentration of L-tryptophan and the change in the fluorescence intensity of the system.
Detailed Description
In order that the invention may be more fully understood, reference will now be made to the following description. This invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete.
Example 1
Preparation of beta-cyclodextrin sulfur quantum dots
Dissolving beta-cyclodextrin (3.7 g) in a round-bottom flask containing 20mL of NaOH (2.0 mol/L) solution, stirring at room temperature until the beta-cyclodextrin is completely dissolved, and then adding sublimed sulfur powder (1.4 g) and ultrapure water (30 mL) into the solution; and then placing the solution in an oil bath at 70 ℃ for stirring for 144h, and dialyzing for 24h by a dialysis bag with the molecular weight cutoff of 3500Da to obtain the beta-cyclodextrin sulfur quantum dots.
As shown in figure 1, the infrared spectrograms of sublimed sulfur powder, beta-cyclodextrin sulfur quantum dots and beta-cyclodextrin are sequentially arranged from top to bottom at 3410cm -1 、1633cm -1 The absorption peaks appeared at the positions correspond to the stretching vibration and the bending vibration of-OH respectively. 2926cm -1 Is the characteristic absorption peak of C-H stretching vibration. At 1155cm -1 、1030cm -1 The absorption peaks appeared at the positions correspond to C-O stretching vibration and O-H bending vibration of the beta-cyclodextrin respectively. By comparing the infrared spectrogram, the beta-cyclodextrin can be foundThe sulfur quantum dots and the beta-cyclodextrin are 1155cm -1 The absorption peaks are all strong, and the sublimed sulfur powder has no absorption peak at the positions. From this, it was found that β -cyclodextrin was successfully attached to the surface of the sulfur quantum dot.
FIG. 2 is a fluorescence excitation and emission spectrum of beta-cyclodextrin sulfur quantum dots. As can be seen from FIG. 2, the excitation wavelength of the beta-cyclodextrin sulfur quantum dots is 312nm, and the emission wavelength is 420nm.
Example 2
Stability testing of beta-cyclodextrin sulfur quantum dots
In order to examine the fluorescence stability of the beta-cyclodextrin sulfur quantum dots, the concentration of the beta-cyclodextrin sulfur quantum dots is fixed, 0.1mol/L PBS buffer solutions with different pH values are added, and the fluorescence intensity at 420nm is measured by fixing the excitation wavelength of 340 nm. FIG. 3 is the effect of pH conditions on the stability of beta-cyclodextrin sulfur quantum dots. As can be seen from FIG. 3, the beta-cyclodextrin sulfur quantum dots have good stability and good fluorescence performance within a wide pH (3.0-12) value range.
Fixing the concentration of the beta-cyclodextrin sulfur quantum dots, adding NaCl solutions with different concentrations and the same volume, finally fixing the volume by using 0.1mol/L Tris-HCl buffer solution with the pH value of 7.0, and inspecting the influence of the ionic strength on the stability of the beta-cyclodextrin sulfur quantum dots, wherein the result is shown in figure 4. As can be seen from FIG. 4, when the concentration of sodium chloride is increased to 1.0mol/L, the fluorescence property of the beta-cyclodextrin sulfur quantum dots is hardly affected, and it can be seen that the beta-cyclodextrin sulfur quantum dots have good stability and good fluorescence property.
Example 3
Selectivity test of beta-cyclodextrin sulfur quantum dots
In order to ensure the accuracy of the chiral beta-cyclodextrin sulfur quantum dots in the analysis of L-tryptophan in a complex sample, under the same test conditions, the influence of some potential interfering species including L-Val, L-His, L-Glu, L-Leu, L-Cys, L-Ala, L-Arg, L-Asn, thr, L-Phe, D/L-Ser, gly and D-Trp amino acids on the fluorescence intensity of the chiral beta-cyclodextrin sulfur quantum dots is determined. And respectively adding the interfering species into a Tris-HCl buffer solution, then adding a beta-cyclodextrin sulfur quantum dot solution, and fixing the excitation wavelength at 340nm to perform fluorescence intensity measurement at 420nm. FIG. 5 is a graph showing the change in fluorescence intensity of the amino acid and L-tryptophan at equal concentrations after incubation for 24 hours in a water bath at 30 ℃. As can be seen from FIG. 5, the fluorescence intensity of the beta-cyclodextrin sulfur quantum dots is significantly enhanced only after the addition of L-tryptophan. After other amino acids are added, the fluorescence intensity of the cyclodextrin sulfur quantum dots is basically not changed obviously, which indicates that other amino acids have no influence on the fluorescence intensity of the beta-cyclodextrin sulfur quantum dots. Therefore, the cyclodextrin sulfur quantum dots have higher selectivity to the L-tryptophan.
Example 4
Fluorescence change of beta-cyclodextrin sulfur quantum dots in the presence of L-tryptophan with different concentrations
The beta-cyclodextrin sulfur quantum dot prepared in example 1 was mixed with an L-tryptophan solution, and Tris-HCl buffer (pH = 7.0) was added to the mixture, the final concentration of the L-tryptophan solution was in the range of 0-1.0 μ M, and the fluorescence intensity of the beta-cyclodextrin sulfur quantum dot-L-tryptophan system at 420nm was tested at an excitation wavelength of 340 nm. Establishing a standard curve for analyzing and detecting the L-tryptophan according to the relation between the concentration of the L-tryptophan and the corresponding fluorescence change of a beta-cyclodextrin sulfur quantum dot-L-tryptophan system, wherein the fluorescence intensity is gradually enhanced along with the increase of the concentration of the L-tryptophan, as shown in figure 6, the fluorescence intensity and the concentration of the L-tryptophan are in a good linear relation within the range of 50-500nmol/L, and the corresponding linear regression equation is y =4.183 × 10 -2 x-0.3053, correlation coefficient R 2 =0.996, and the detection limit (LOD =3 σ/k) was 9.3nmol/L (n = 11).
Example 5
Detection of L-tryptophan in amino acid injection
Adding the beta-cyclodextrin sulfur quantum dots into 2.0mL of amino acid injection, then adding 2.0mL of Tris-HCl buffer (pH = 7.0), fixing the excitation wavelength to be 340nm, measuring the fluorescence intensity of a detection solution at 420nm, and calculating by using a linear regression equation in example 4 to measure that the content of the L-tryptophan in the amino acid injection is 108.10nmol/L. On the basis, the amino acid injection is subjected to the standard addition recovery experiment of the L-tryptophan, the result is shown in the table, and the standard addition recovery rate of the L-tryptophan is 99.30-103.36%, and the RSD is less than 4.0% (n = 6). The result shows that the beta-cyclodextrin sulfur quantum dots provided by the invention are successfully applied to the quantitative analysis of L-tryptophan in the amino acid injection.
TABLE 1 determination of L-Tryptophan in amino acid injection
The technical features of the embodiments described above may be arbitrarily combined, and for the sake of brevity, all possible combinations of the technical features in the embodiments described above are not described, but should be considered as being within the scope of the present specification as long as there is no contradiction between the combinations of the technical features.
The above-mentioned embodiments only express several embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent shall be subject to the appended claims.
Claims (10)
1. A fluorescent probe for detecting L-tryptophan is characterized in that the fluorescent probe is a beta-cyclodextrin sulfur quantum dot.
2. The fluorescent probe of claim 1, wherein: the preparation method of the beta-cyclodextrin sulfur quantum dot comprises the following steps: dissolving beta-cyclodextrin in NaOH solution, adding sublimed sulfur powder and ultrapure water, and heating and dialyzing to obtain the beta-cyclodextrin sulfur quantum dot.
3. The fluorescent probe of claim 2, wherein: the concentration of the NaOH solution is 1.8-2.0mol/L.
4. The fluorescent probe of claim 2, wherein: the mass ratio of the beta-cyclodextrin to the sublimed sulfur powder is 3:1-2.5.
5. The fluorescent probe of claim 2, wherein: the heating mode is oil bath heating.
6. The fluorescent probe of claim 2, wherein: the heating time is 120-144h, and the temperature is 60-80 ℃.
7. The fluorescent probe of claim 2, wherein: the specific process of dialysis is as follows: dialyzing in dialysis bag with molecular weight cutoff of 3500Da for 12-24h.
8. Use of a fluorescent probe according to any one of claims 1 to 7 in the detection of L-tryptophan.
9. Use according to claim 8, characterized in that: the method is applied to detection and determination of L-tryptophan in amino acid injection.
10. Use according to claim 8, characterized in that: adding beta-cyclodextrin sulfur quantum dots into the solution to be detected, adding a Tris-HCl buffer solution, and performing fluorescence spectrometry at a fixed excitation wavelength of 340 nm.
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