CN113736452B - Method for detecting salicylic acid by fluorescent micron probe and application - Google Patents
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Abstract
The invention discloses a method for detecting salicylic acid by using a fluorescent micron probe and application thereof, wherein curcumin is used as a target, hexachlorocyclotriphosphazene is used as a connecting group to form a polycyclotriphosphazene co-curcumin fluorescent microsphere, the fluorescent microsphere is complexed with Al (III) to form a PC-Al (III) fluorescent micron probe, and in an ethanol solution system, the salicylic acid is complexed with the PC-Al (III) fluorescent micron probe to form a PC-Al (III) -SA ternary system, so that a purple fluorescent signal appears in the solution system, and the detection of salicylic acid is realized. The invention can realize the rapid response to the salicylic acid within 1min, the system has obvious fluorescence enhancement phenomenon, the lowest detection limit to the salicylic acid is as low as 0.1 mu M, and the invention has the advantages of higher sensitivity, stronger anti-interference capability, rapid identification and accurate and simple detection result.
Description
Technical Field
The invention belongs to the technical field of salicylic acid detection, and in particular relates to a method for detecting salicylic acid by using a fluorescent micron probe and application thereof.
Background
Salicylic Acid (SA), a small molecular phenolic compound commonly found in plants, 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 long-term use of high-dose salicylic acid causes nausea and dizziness and gastrointestinal adverse reactions. In addition, since SA has anti-acne and whitening effects, it has been widely used in cosmetics for skin care, beauty and skin disease treatment in daily life. However, excessive use of such compounds can have negative effects on the health of the consumer, such as irritation, and may cause damage to the skin, and the determination of salicylic acid in pharmaceuticals and cosmetics is particularly important for quality assurance and consumer safety.
In the prior art, methods for detecting the concentration of SA mainly comprise ultraviolet spectrophotometry, fluorescence spectrophotometry, colorimetric method, electrochemical analysis method, gas chromatography, high performance liquid chromatography and the like, but the methods often require expensive instruments, time consuming and complex operations and the like, and are rarely suitable for conventional analysis. In recent years, since fluorescent probes have good characteristics such as good selectivity, high sensitivity, convenient observation, and capability of real-time detection, detection of SA can be performed using fluorescent probes, but most fluorescent probes have slow response time and poor sensitivity.
Disclosure of Invention
The main object of the present invention is to provide a fluorescent micron probe.
The invention also aims to provide the application of the fluorescent micrometer probe in detecting salicylic acid, and the fluorescent micrometer probe has the advantages of quick response time and high sensitivity, and particularly has the advantage of quick detection of salicylic acid in medicines or cosmetics.
In order to achieve the above purpose, the invention adopts the following technical scheme:
a fluorescent microsphere is a copolymer formed by curcumin and hexachlorocyclotriphosphazene, wherein the hydroxyl group of the curcumin is condensed with chlorine of the hexachlorocyclotriphosphazene 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) The cyclotriphosphazene and the curcumin are dissolved in an organic solvent;
(2) Triethylamine was added and the reaction was carried out for 4 to 12 hours.
The organic solvent of step (1) is acetonitrile, toluene, tetrahydrofuran or DMF, preferably acetonitrile.
In 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 step (2), the mole ratio of hexachlorocyclotriphosphazene is 1:50-150, preferably 1:80-100, and in a preferred mode of the invention, the mole ratio of hexachlorocyclotriphosphazene to triethylamine is 1:90.
After the reaction of the step (2), centrifuging or filtering, collecting the precipitate by suction filtration, washing with water and ethanol, and drying.
A fluorescent micrometer probe is a mixture of the fluorescent microsphere and aluminum ions.
The fluorescent microspheres are dissolved in ethanol solution and then mixed with aluminum salt solution to form fluorescent micrometer probes, wherein the mass ratio of the fluorescent microspheres to aluminum ions in the mixed system is 1:1-2, preferably 1:1.7.
A method for detecting salicylic acid, comprising the steps of:
(1) Dissolving the fluorescent microspheres in ethanol solution, and then mixing with 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) Mixing the mixture obtained in the step (1) with a sample to be detected, and measuring the fluorescence emission intensity at 400nm by taking 313nm as an excitation wavelength to perform qualitative or quantitative detection.
In the step (1), the ethanol solution of the fluorescent microspheres is mixed with the aluminum salt solution, and then 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 salicylic acid concentration detected in the invention is 0.5 to 5 multiplied by 10 -5 The minimum detection limit is 0.1. Mu. Mol/L.
Mechanism of recognition of salicylic acid by fluorescent micron probes: because of the good coordination capability of salicylic acid and 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 salicylic acid detection, are fluorescence enhancement type probes, and have better specific selection, anti-interference performance and higher sensitivity compared with fluorescence quenching type probes; the invention utilizes the good coordination capability of salicylic acid and metal ions, and releases strong purple fluorescence after the probe is combined with the salicylic acid, so that the fluorescence of a solution system is obviously enhanced, thereby realizing the detection of the salicylic acid.
(2) The invention provides a polyphosphazene hyperbranched micron-sized fluorescent probe based on a complexing mechanism, which realizes fluorescence enhancement and identification of salicylic acid through the complexing capability of salicylic acid and metal ions, utilizes curcumin as a fluorophore, realizes complexing with the metal ions through carbonyl groups of the fluorophore and modulates fluorescence change, and a hyperbranched skeleton of polyphosphazene is beneficial to construction of a curcumin-metal ion-salicylic acid microreactor so as to improve fluorescence signal stability and sensing performance under complex background interference, and has strong practicability in complex simulation sample environments of various metal ions and salicylic acid substances.
(3) The minimum detection limit of the salicylic acid micromolecules is 0.1 mu mol/L, the rapid response within 1min is realized, the detection process is simple and convenient, the anti-interference capability is strong, the detection is rapid and sensitive, the detection result is accurate, and the salicylic acid micromolecule detection method can be used for detecting salicylic acid, especially for rapidly detecting salicylic acid in medicines and cosmetics.
Drawings
FIG. 1 is a graph showing fluorescence selectivity of PC-Al (III) as a fluorescent microprojection in the example, and the excitation wavelength is 313nm.
FIG. 2 is a diagram showing interference resistance of a fluorescent micron probe PC-Al (III) to identify salicylic acid in the example, wherein the excitation wavelength is 313nm.
FIG. 3 is a graph showing the response time of the fluorescent microprojection PC-Al (III) to salicylic acid in the examples.
FIG. 4 shows the stability of the fluorescent microprojection PC-Al (III) recognition salicylic acid in the examples.
FIG. 5 is a fluorescence titration diagram of a fluorescent microprojection PC-Al (III) recognition salicylic acid with excitation wavelength of 313nm in the example.
FIG. 6 is a graph showing the lowest detection limit of salicylic acid identified by the fluorescent microprojection PC-Al (III) in the example, and the excitation wavelength is 313nm.
Detailed Description
The technical solutions of the present invention will be clearly and completely described in conjunction with the embodiments of the present invention, and it is apparent that the described embodiments are only some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without any inventive effort, are intended to be within the scope of the invention.
The chemical reagent and solvent used in the preparation process of the fluorescent micron probe PC-Al (III) are purchased from exploration company, metal ions and the like are purchased from Aba Ding Shiji company, and a fluorescent spectrum is recorded by using an Edinburgh FS-5 fluorescent analyzer.
Example 1 preparation of fluorescent microspheres and fluorescent microprojections
Preparation of fluorescent microspheres
In a 250mL round bottom flask, 0.10g (0.30 mmol) of Hexachlorocyclotriphosphazene (HCCP) and 0.32g (0.90 mmol) of curcumin were dissolved in 50mL of acetonitrile, after hexachlorocyclotriphosphazene and curcumin were completely dissolved in acetonitrile solution, 2mL of triethylamine (about 27 mmol) was added and stirred at room temperature for 8 hours. Centrifuging after the reaction is completed to obtain a lower precipitate, washing the lower precipitate with ethanol and purified water until the supernatant is clear, and vacuum drying 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:
preparation of (II) fluorescent micron probe PC-Al (III)
Preparing 12mg/mL PC solution with ethanol solution, and preparing 100mg/mL Al (NO) with purified water 3 ) 3 ·9H 2 O aqueous solution (aluminum ion concentration 7 mg/mL), 10. Mu.L of PC solution and 10. Mu.L of Al (III) solution were added to 2mL of ethanol solution, and the mixture was mixed well to prepare a probe.
Example 2 fluorescence specific selectivity
An ethanol solution of 12mg/mL of PC and an Al (III) aqueous solution of 100mg/mL were prepared, 2mL of the ethanol solution, 10. Mu.L of the PC solution and 10. Mu.L of the Al (III) aqueous solution were added to a cuvette, and the selectivity of the probe PC-Al (III) to small molecules such as salicylic acid was examined by a fluorescence spectrometer. As shown in FIG. 1, under the excitation condition of 313nm, the single probe PC-Al (III) has weak fluorescence emission intensity at 400nm in 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 the fluorescence emission intensity of the single probe system, so that the probe PC-Al (III) has better fluorescence specific selectivity to salicylic acid in ethanol solution.
Example 3 interference immunity test
12mg/mL of PC in ethanol and 100mg/mL of Al (III) in water were prepared, and 2mL of ethanol and 10. Mu.L of PC in water and 10. Mu.L of Al (III) in water were added to 18 clean fluorescent cuvettes, respectively, and 10. Mu.M salicylic acid and 100. Mu.M of other analytes were added, respectively, as follows:
other classes of small molecules: salicylamide (SAM), benzoic Acid (BA), p-hydroxybenzoic acid (4-HBA);
cation: na (Na) + 、K + 、Ca 2+ 、Mg 2+ 、Co 2+ 、Ni 2+ 、Cu 2+ 、Zn 2+ 、Sn 2+ 、Fe 3+ ；
Anions: cl - 、NO 3 - 、ACO - 、HCO 3 - 、CO 3 2- And (3) detecting on a fluorescence spectrometer, drawing a fluorescence emission histogram of the highest fluorescence intensity corresponding to different analytes, and as shown in figure 2, proving that the recognition of the probe PC-Al (III) on salicylic acid in ethanol solution is not interfered by other analytes, and the probe PC-Al (III) has better anti-interference performance.
Example 4 response time test
12mg/mL of PC in ethanol and 100mg/mL of Al (III) in water were prepared, 2mL of ethanol solution, 10. Mu.L of PC solution and 10. Mu.L of Al (III) solution were added to the cuvette, and the response time of the probe PC-Al (III) to small salicylic acid molecules was examined by a fluorescence spectrometer. The detection of the salicylic acid can be realized within 1min by the PC-Al (III), as shown in figure 3, which proves that the rapid response of the probe PC-Al (III) to the salicylic acid can realize the rapid detection of the salicylic acid in ethanol solution.
Example 5 stability test
An ethanol solution of 12mg/mL of PC and an Al (III) aqueous solution of 100mg/mL were prepared, and 2mL of the ethanol solution, 10. Mu.L of the PC solution and 10. Mu.L of the Al (III) solution were added to a cuvette and the effect of salicylic acid detection was measured while maintaining the temperature for 0 to 120 minutes. As shown in FIG. 4, the fluorescence of the probe PC-Al (III) and the fluorescence intensity of the probe PC-Al (III) on salicylic acid detection hardly change within 2 hours, 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 of ethanol solution of PC and 100mg/mL of Al (III) aqueous solution, preparing 2mmol/L of salicylic acid solution, adding 2mL of ethanol solution, 10 mu L of PC and 10 mu L of Al (III) aqueous solution into a clean fluorescence cuvette, gradually adding the salicylic acid solution with the volumes of 0, 5 mu L, 10 mu L, 15 mu L, 20 mu L, 25 mu L, 30 mu L, 35 mu L, 40 mu L, 45 mu L, 50 mu L and 55 mu L respectively, simultaneously taking 313nm as an excitation wavelength, measuring the fluorescence emission intensity at 400nm on a fluorescence spectrometer, taking the fluorescence intensity at 400nm as an abscissa, obtaining a working curve of the salicylic acid concentration with the fluorescence intensity at 400nm as an ordinate, and taking a linear regression equation as F 400nm ＝3.58×10 10 C-1.05×10 -5 The unit of C is mol/L as shown in FIG. 5.
Example 7 minimum detection limit experiment
A good detection limit is one of the criteria for checking whether a probe molecule has application value, preparing 12mg/mL of ethanol solution of PC and 100mg/mL of Al (III) aqueous solution, adding 2mL of ethanol solution, 10 mu L of PC and 10 mu L of Al (III) aqueous solution into a clean fluorescent cuvette, measuring the response intensity of the solution to salicylic acid with different concentrations, and increasing the fluorescence emission intensity of the system at 400nm along with the increase of the concentration of the salicylic acid, so as to find the dissolutionThe fluorescence emission intensity of the liquid is in the linear range of 0.5-5×10 in salicylic acid concentration -5 mol/L(R 2 The detection limit of the probe molecule on salicylic acid is 0.1 mu mol/L (figure 6) obtained by calculation (3 sigma/k), which shows that the probe PC-Al (III) has potential application value on the detection of salicylic acid.
Claims (1)
1. A method of detecting salicylic acid, comprising the steps of:
(1) Dissolving fluorescent microspheres in ethanol solution, mixing with aluminum salt solution, and adding a sample to be tested for mixing;
in the mixed system of the step (1), the mass ratio of the fluorescent microspheres to aluminum ions is 1:1-2;
the particle size of the fluorescent microsphere is 0.5-2 microns, and the fluorescent microsphere is a copolymer formed by curcumin and hexachlorocyclotriphosphazene;
the preparation method of the fluorescent microsphere comprises the following steps: dissolving hexachlorocyclotriphosphazene and curcumin in a molar ratio of 1:1.5-5 in an organic solvent; adding triethylamine, and reacting for 4-12 hours, wherein the mol ratio of hexachlorocyclotriphosphazene to triethylamine is 1:50-150;
(2) And (3) using 313nm as excitation wavelength, measuring fluorescence emission intensity at 400nm, and carrying out qualitative or quantitative detection.
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