CN113736452A - Method for detecting salicylic acid by using fluorescent micrometer probe and application - Google Patents
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Abstract
The invention discloses a method for detecting salicylic acid by using a fluorescent micrometer probe and application thereof, which are characterized in that curcumin is used as a target, hexachlorocyclotriphosphazene is used as a connecting group to form polycyclotriphosphazene-curcumin fluorescent microspheres, the fluorescent microspheres and Al (III) are complexed to form a PC-Al (III) fluorescent micrometer probe, and in an ethanol solution system, salicylic acid and the fluorescent micrometer probe PC-Al (III) are complexed to form a PC-Al (III) -SA ternary system, so that a purple fluorescent signal appears in the solution system, and the salicylic acid is detected. The invention can realize quick response to the salicylic acid within 1min, has obvious fluorescence enhancement phenomenon in the system, has the lowest detection limit of 0.1 mu M to the salicylic acid, and has higher sensitivity, stronger anti-interference capability, quick identification and accurate and simple detection result.
Description
Technical Field
The invention belongs to the technical field of salicylic acid detection, and particularly relates to a method for detecting salicylic acid by using a fluorescent micrometer probe and application thereof.
Background
Salicylic Acid (SA), known by the chemical name o-hydroxybenzoic acid, is a common small molecular phenolic compound in plants, and is widely used as an antimicrobial and antifungal agent in many medical products due to its broad spectrum, good stability, non-volatility, etc., and is generally used for treating common skin diseases such as acne, callus and psoriasis, and relieving pain and fever, but the long-term use of high dose of salicylic acid causes nausea and dizziness and gastrointestinal adverse reactions. In addition, since SA has anti-acne and whitening effects, it has also been widely added to cosmetics for skin care, beauty and dermatologic treatment in daily life. However, excessive use of such compounds can have negative effects on consumer health, such as irritation, and may cause skin damage, and the determination of salicylic acid in pharmaceutical and cosmetic products is particularly important for quality assurance and consumer safety.
In the prior art, methods for detecting the concentration of SA mainly include an ultraviolet spectrophotometry, a fluorescence spectrophotometry, a colorimetric method, an electrochemical analysis method, a gas chromatography, a high performance liquid chromatography and the like, but these methods usually require expensive instruments, time-consuming and complex operations and the like, and are rarely suitable for routine analysis. In recent years, since fluorescent probes have excellent characteristics such as good selectivity, high sensitivity, easy observation, and real-time detection, SA can be detected by fluorescent probes, but most of fluorescent probes have a slow response time and poor sensitivity.
Disclosure of Invention
The invention mainly aims to provide a fluorescent micrometer probe.
The invention also aims to provide the application of the fluorescent micrometer probe in the detection of the salicylic acid, which has the advantages of quick response time and high sensitivity, and is particularly suitable for the quick detection of the salicylic acid in the medicines or cosmetics.
In order to achieve the purpose, the invention adopts the following technical scheme:
a fluorescent microsphere is a copolymer formed by curcumin and hexachlorocyclotriphosphazene, wherein hydroxyl of the curcumin and chlorine of the hexachlorocyclotriphosphazene are condensed to form the copolymer.
Preferably, the fluorescent microspheres have a particle size of 0.5-2 microns.
The preparation method of the fluorescent microsphere comprises the following steps:
(1) dissolving cyclotriphosphazene and curcumin in an organic solvent;
(2) adding triethylamine, and reacting for 4-12 hours.
The organic solvent of step (1) is acetonitrile, toluene, tetrahydrofuran or DMF, preferably acetonitrile.
In the step (1), the molar ratio of hexachlorocyclotriphosphazene to curcumin is 1: 1.5-5, preferably 1: 2-4, and in a preferred mode of the invention, the molar ratio of hexachlorocyclotriphosphazene to curcumin is 1: 3.
In the step (2), the molar ratio of hexachlorocyclotriphosphazene is 1: 50-150, preferably 1: 80-100, and in a preferred mode of the invention, the molar ratio of hexachlorocyclotriphosphazene to triethylamine is 1: 90.
And (3) after the reaction in the step (2) is finished, centrifuging or filtering, performing suction filtration, collecting the precipitate, washing with water and ethanol, and drying.
A fluorescent micrometer probe is a mixture of the fluorescent microsphere and aluminum ions.
Dissolving the fluorescent microspheres in an ethanol solution, and mixing the solution with an aluminum salt solution to form the fluorescent micrometer probe, wherein the mass ratio of the fluorescent microspheres to aluminum ions in a mixed system is 1: 1-2, and preferably 1: 1.7.
A method for detecting salicylic acid comprises the following steps:
(1) dissolving the fluorescent microspheres in an ethanol solution, and mixing the solution with an aluminum salt solution; the mass ratio of PC to Al (III) in the mixed system is 1: 1-2, preferably 1: 1.7; then adding a sample to be tested and mixing;
(2) and (2) mixing the mixture obtained in the step (1) with a sample to be detected, measuring the fluorescence emission intensity at 400nm by taking 313nm as an excitation wavelength, and performing qualitative or quantitative detection.
In the step (1), after the ethanol solution of the fluorescent microspheres is mixed with the aluminum salt solution, the mixture is diluted by the ethanol solution until the content of the fluorescent microspheres is 50-100 mug/mL.
The linear range of the concentration of the salicylic acid detected by the method is 0.5-5 multiplied by 10-5mol/L, the lowest detection limit is 0.1 mu mol/L.
Mechanism of salicylic acid recognition by fluorescent microprobe: due to the good coordination capability of the salicylic acid and the metal ions, the salicylic acid is combined with Al (II) in the probe to form a ternary system of PC-Al (III) -SA, and a fluorescence signal is released, so that the fluorescence of the system is enhanced.
The invention has the beneficial effects that:
(1) the fluorescent microsphere and the probe obtained by the invention can be used for detecting salicylic acid, are fluorescence-enhanced probes, and have better specific selection, anti-interference performance and higher sensitivity compared with fluorescence quenching probes; according to the invention, good coordination capability of salicylic acid and metal ions is utilized, strong purple fluorescence is released after the probe is combined with the salicylic acid, and the fluorescence of a solution system is obviously enhanced, so that the salicylic acid is detected.
(2) The invention provides a polyphosphazene hyperbranched micron-sized fluorescent probe based on a complexing mechanism, which realizes fluorescence enhancement and salicylic acid identification through the complexing capacity of salicylic acid and metal ions, utilizes curcumin as a fluorophore, realizes complexation with the metal ions through carbonyl of the fluorophore and modulates fluorescence change, and the hyperbranched framework of polyphosphazene is beneficial to the construction of a curcumin-metal ion-salicylic acid microreactor so as to improve the fluorescence signal stability and the sensing performance under the interference of a complex background, and has strong practicability in the complex simulated sample environment of various metal ions and salicylic acid substances.
(3) The invention has the lowest detection limit of 0.1 mu mol/L on salicylic acid micromolecules, realizes quick response within 1min, has simple and convenient detection process, strong anti-interference capability, quickness and sensitivity and accurate detection result, and can be used for detecting salicylic acid, particularly the salicylic acid in medicines and cosmetics.
Drawings
FIG. 1 is a fluorescence selectivity diagram of a fluorescent micrometer probe PC-Al (III) in the example, and the excitation wavelength is 313 nm.
FIG. 2 is an anti-interference graph for identifying salicylic acid by a fluorescent micrometer probe PC-Al (III) in the example, and the excitation wavelength is 313 nm.
FIG. 3 is a graph of response time of fluorescent microprobe PC-Al (III) to salicylic acid in examples.
FIG. 4 shows the stability of salicylic acid identified by the fluorescent microprobe PC-Al (III) in the examples.
FIG. 5 is a fluorescence titration chart of the fluorescent micrometer probe PC-Al (III) for identifying salicylic acid in the example, and the excitation wavelength is 313 nm.
FIG. 6 is a diagram of the lowest detection limit of salicylic acid identified by the fluorescent micrometer probe PC-Al (III) in the example, and the excitation wavelength is 313 nm.
Detailed Description
The technical solutions of the present invention will be described clearly and completely with reference to the following embodiments of the present invention, and it should be understood that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be obtained by a person skilled in the art without inventive effort based on the embodiments of the present invention, are within the scope of the present invention.
The chemical reagents and solvents used in the preparation of the fluorescent microprobe PC-Al (III) were purchased from explorations, the metal ions and the like were purchased from Aladdin reagents, and the fluorescence spectra were recorded using an Edinburgh FS-5 fluorescence analyzer, England.
EXAMPLE 1 preparation of fluorescent microspheres and fluorescent microprobes
Preparation of fluorescent microspheres
In a 250mL round bottom flask, 0.10g (0.30mmol) of Hexachlorocyclotriphosphazene (HCCP) and 0.32g (0.90mmol) of curcumin were dissolved in 50mL of acetonitrile, and after the hexachlorocyclotriphosphazene and curcumin were completely dissolved in the acetonitrile solution, 2mL of triethylamine (about 27mmol) was added and the mixture was stirred at room temperature for 8 hours. Centrifuging after complete reaction to obtain a lower-layer precipitate, washing the precipitate with ethanol and purified water until the supernatant is clear, and performing vacuum drying on the obtained precipitate at 50 ℃ for 12 hours to obtain light yellow powder with the particle size of 0.5-2 microns, wherein the technical route is as follows:
(II) preparation of fluorescent micrometer probe PC-Al (III)
Preparing 12mg/mL PC solution with ethanol solution, and preparing 100mg/mL Al (NO) with purified water3)3·9H2O aqueous solution (aluminum ion concentration 7mg/mL), and adding 10. mu.L of PC solution and 10. mu.L of Al (III) solution into 2mL of ethanol solution, and uniformly mixing to obtain the finished probe.
Example 2 fluorescence specificity selectivity
A12 mg/mL ethanol solution of PC and a 100mg/mL aqueous solution of Al (III) are prepared, 2mL ethanol solution, 10. mu.L PC solution and 10. mu.L aqueous solution of Al (III) are added to a cuvette, and the selectivity of the probe PC-Al (III) to small molecules such as salicylic acid is examined by a fluorescence spectrometer. As shown in figure 1, under the excitation condition of 313nm, the single probe PC-Al (III) has weak fluorescence emission intensity at 400nm in an ethanol solution, when salicylic acid is added, the fluorescence emission intensity at 400nm is obviously enhanced, and when other substances are added, the fluorescence emission intensity of a solution system is not obviously changed compared with that of the single probe system, so that the probe PC-Al (III) has better fluorescence specificity selectivity on the salicylic acid in the ethanol solution.
Example 3 interference immunity test
12mg/mL of PC in ethanol and 100mg/mL of Al (III) in water are prepared, and 2mL of ethanol and 10. mu.L of PC and 10. mu.L of Al (III) are added to 18 clean fluorescence cuvettes, respectively, followed by 10. mu.M of salicylic acid and 100. mu.M of other analytes, such as:
other classes of small molecules: salicylamide (SAM), Benzoic Acid (BA), p-hydroxybenzoic acid (4-HBA);
cation: na (Na)+、K+、Ca2+、Mg2+、Co2+、Ni2+、Cu2+、Zn2+、Sn2+、Fe3+；
Anion: cl-、NO3 -、ACO-、HCO3 -、CO3 2-In the fluorescence ofDetecting on a spectrometer, and drawing a fluorescence emission histogram with the highest fluorescence intensity corresponding to different analytes, as shown in fig. 2, which proves that the probe PC-Al (III) has better anti-interference performance on the recognition of salicylic acid in the ethanol solution without being interfered by other analytes.
Example 4 response time testing
12mg/mL of PC ethanol solution and 100mg/mL of Al (III) water solution are prepared, 2mL of ethanol solution, 10 μ L of PC solution and 10 μ L of Al (III) solution are added into a cuvette, and the response time of the probe PC-Al (III) to the salicylic acid micromolecule is examined by a fluorescence spectrometer. The detection of the salicylic acid can be realized within 1min by the PC-Al (III), and as shown in figure 3, the rapid response of the probe PC-Al (III) to the salicylic acid can be proved to realize the rapid detection of the salicylic acid in an ethanol solution.
Example 5 stability testing
12mg/mL of an ethanol solution of PC and 100mg/mL of an aqueous solution of Al (III) are prepared, and 2mL of the ethanol solution, 10 μ L of the PC solution and 10 μ L of the Al (III) solution are added into a cuvette and kept for 0-120min to determine the detection effect on salicylic acid. As shown in the attached figure 4, the fluorescence of the probe PC-Al (III) and the fluorescence intensity of the probe PC-Al (III) for salicylic acid detection are almost unchanged within 2h, and the result shows that the probe PC-Al (III) shows good stability in an ethanol solution system.
Example 6 Linear regression equation
Preparing 12mg/mL PC ethanol solution and 100mg/mL Al (III) water solution, preparing 2mmol/L salicylic acid solution, adding 2mL ethanol solution, 10 μ L PC and 10 μ L Al (III) water solution into a clean fluorescence cuvette, gradually adding salicylic acid solution with the volume of 0, 5 μ L, 10 μ L, 15 μ L, 20 μ L, 25 μ L, 30 μ L, 35 μ L, 40 μ L, 45 μ L, 50 μ L and 55 μ L while using 313nm as excitation wavelength, measuring fluorescence emission intensity at 400nm on a fluorescence spectrometer, obtaining a working curve of salicylic acid concentration by using salicylic acid concentration as abscissa and fluorescence intensity at 400nm as ordinate, and using a linear regression equation F400nm＝3.58×1010C-1.05×10-5And the unit of C is mol/L, as shown in FIG. 5.
Example 7 lowest detection Limit experiment
The good detection limit is one of the standards for checking whether one probe molecule has application value, 12mg/mL of ethanol solution of PC and 100mg/mL of Al (III) aqueous solution are prepared, 2mL of ethanol solution, 10 mu L of PC and 10 mu L of Al (III) aqueous solution are added into a clean fluorescence cuvette, the response intensity of the cuvette to different concentrations of salicylic acid is measured, the fluorescence emission intensity of the system is continuously enhanced at 400nm along with the increase of the concentration of the salicylic acid, and the fluorescence emission intensity of the solution is found to be 0.5-5 x 10 in the linear range of the concentration of the salicylic acid-5mol/L(R2The detection limit of the probe molecule to the salicylic acid is 0.1 mu mol/L (figure 6) through calculation (3 sigma/k), and the detection of the probe PC-Al (III) to the salicylic acid has potential application value.
Claims (9)
1. A fluorescent microsphere is characterized in that the fluorescent microsphere is a copolymer formed by curcumin and hexachlorocyclotriphosphazene.
2. The fluorescent microsphere of claim 1, wherein the particle size is 0.5-2 microns.
3. The method for preparing fluorescent microspheres according to claim 1 or 2, comprising the steps of:
(1) dissolving cyclotriphosphazene and curcumin in an organic solvent;
(2) adding triethylamine, and reacting for 4-12 hours.
4. The method for producing fluorescent microspheres according to claim 3,
in the step (1), the molar ratio of hexachlorocyclotriphosphazene to curcumin is 1: 1.5-5;
in the step (2), the molar ratio of hexachlorocyclotriphosphazene to triethylamine is 1: 50-150.
5. A fluorescent microprobe which is a mixture of the fluorescent microsphere of claim 1 or 2 and aluminum ions.
6. The method for preparing a fluorescent microprobe according to claim 5, comprising the steps of: the fluorescent microsphere according to claim 1 or 2, which is obtained by dissolving the fluorescent microsphere in an ethanol solution and mixing the solution with an aluminum salt solution.
7. Use of the fluorescent microsphere of claim 1 or 2, the fluorescent microprobe of claim 5 for detecting salicylic acid.
8. A method for detecting salicylic acid, comprising the steps of:
(1) dissolving the fluorescent microspheres of claim 1 or 2 in an ethanol solution, mixing with an aluminum salt solution, adding a sample to be tested, and mixing;
(2) and measuring the fluorescence emission intensity at 400nm by taking 313nm as an excitation wavelength, and performing qualitative or quantitative detection.
9. The method for detecting salicylic acid according to claim 8, wherein in the mixed system in the step (1), the mass ratio of the fluorescent microspheres to the aluminum ions is 1: 1-2.
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| CN113143785A (en) * | 2021-04-02 | 2021-07-23 | 西安交通大学 | Natural polyphenol functionalized antioxidant compound sunscreen agent and preparation method thereof |
| CN113563592A (en) * | 2021-06-11 | 2021-10-29 | 上海工程技术大学 | Fluorescent microsphere, fluorescent probe and method for detecting tetracycline |
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