CN109239039B - Acetaldehyde detection method based on fluorescent probe and application thereof - Google Patents
Acetaldehyde detection method based on fluorescent probe and application thereof Download PDFInfo
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Abstract
The invention provides an acetaldehyde detection method based on a fluorescent probe and application thereof, and particularly provides a method for detecting acetaldehyde based on a fluorescent probe. The specific detection method comprises the following steps: the probe P1 is used as a fluorescent reagent, and the acetaldehyde specificity detection is realized by utilizing the acetaldehyde reactivity to perform a double condensation reaction with the probe P1 in a DMSO-Tris (pH =7.4,6:4, v/v) solution system. The detection method has the advantages of high specific selectivity and sensitivity on acetaldehyde, simple and convenient detection process, strong anti-interference capability, rapidness, sensitivity and accurate detection result.
Description
Technical Field
The invention relates to an acetaldehyde detection technology, in particular to an acetaldehyde detection method based on a fluorescent probe and application thereof.
Background
Acetaldehyde is a highly active two-carbon saturated aldehyde, colorless, flammable, volatile, and not readily bio-concentrated in lipids. Acetaldehyde has wide industrial application, is mainly used as a raw material for producing acetic acid, and is also used for synthesizing chemical reagents such as adjacent sucking, adjacent sucking alkalies, peracetic acid, chloral, ethylene glycol and the like; acetaldehyde is used in the technical processes of mirror silver plating, leather kneading, papermaking, rubber synthesis, aniline dye production, cosmetics, plastic products and the like; in addition, acetaldehyde is useful as a hardening agent for gelatin fibers, a preservative for fish products, and a food seasoning. Acetaldehyde is widely present in daily life, and so far, 150 kinds of foods have been found to contain acetaldehyde. Acetaldehyde is widely present in alcoholic beverages and is recognized as a class I carcinogen by the International agency for research on cancer (IARC). The low concentration of acetaldehyde taken in by the human body causes eye, nose and upper respiratory tract irritation symptoms and bronchitis. Ingestion of high levels of acetaldehyde can lead to anesthesia, with clinical manifestations of headache, lethargy, obnubilation and bronchitis, pulmonary edema, diarrhea, proteinuria and hepatic steatosis, and in severe cases death. Therefore, the development of a method for quickly, sensitively and specifically detecting acetaldehyde has important research significance in the fields of drinking wine, bioscience, agricultural product quality safety and the like.
The fluorescent probe has the advantages of good selectivity, high sensitivity, simple and rapid operation, less damage to a detected object and the like, and is widely applied to the aspects of detecting metal cations, anions, active small molecules in organisms and the like in environments and biological systems. The fluorescent probe is a tool for converting the intermolecular interaction into an easily recognized optical signal and transmitting the optical signal to the outside. After the fluorescent probe and a specific target analyte react, the fluorescent signal can be obviously changed, so that the detection aim is fulfilled. The application provides a first example of acetaldehyde detection method based on a fluorescent probe, and realizes specific identification and detection of acetaldehyde.
Disclosure of Invention
The invention provides an acetaldehyde detection method based on a fluorescent probe, which solves the technical problems of difficult detection and low detection sensitivity of acetaldehyde in drinking wine and agricultural products.
The technical scheme of the invention is realized as follows:
an acetaldehyde detection method based on a fluorescent probe comprises the following steps:
(1) preparing a Tris buffer solution with the pH =7.4 and the concentration of 10 mM, and mixing the Tris buffer solution with dimethyl sulfoxide (DMSO) in proportion to obtain a mixed solution A; preparing a probe P1 solution with the concentration of 1 mM by taking DMSO as a solvent;
(2) preparing 100 mu mol/L acetaldehyde solution by using distilled water, adding the mixed solution A into a clean fluorescent cuvette, adding a probe P1 solution, and then sequentially adding the acetaldehyde solution, wherein the adding volumes are as follows: 0 μ L, 3 μ L, 6 μ L, 9 μ L, 12 μ L, 15 μ L, 18 μ L, 21 μ L, while taking 440 nm as the excitation wavelength, the fluorescence emission intensity at 544nm was measured on a fluorescence spectrometer, and a working curve based on the acetaldehyde concentration was obtained with the acetaldehyde concentration as abscissa and the fluorescence intensity at 544nm as ordinate, and the linear regression equation was: f544 nm=2215.496C +827.705, C being in μmol/L;
(3) adding the mixed solution A and the probe P1 solution into a clean fluorescent cuvette, sucking V mu L of sample solution to be detected by a microsyringe, adding the sample solution to be detected into the fluorescent cuvette containing the mixed solution A and the probe P1 solution, testing on a fluorescence spectrometer, substituting the measured 544nm fluorescence emission intensity into the linear regression equation in the step (2) to obtain the concentration C, and obtaining the concentration C of the sample to be detectedSample to be tested=3000*C/V，CSample to be testedThe unit of (b) is μmol/L.
The volume ratio of the Tris buffer solution to the DMSO in the step (1) is 4: 6.
The fluorescent probe for detecting acetaldehyde is synthesized according to the reference literature (RSC adv., 2015, 5, 7083-:
an acetaldehyde detection method based on a fluorescent probe is characterized in that the linear concentration range of the acetaldehyde detection method is 0-0.7 mu M, and the lowest detection limit is 4.9 x 10-8mol/L。
The acetaldehyde detection method based on the fluorescent probe is applied to detecting acetaldehyde in drinking wine and agricultural products.
The technical scheme of the invention has the following beneficial effects:
(1) the acetaldehyde detection method is the acetaldehyde detection method based on the fluorescent probe for the first time. Compared with a fluorescence quenching probe, the fluorescence enhancement type probe provided by the invention has better specific selection, anti-interference performance and higher sensitivity; the minimum detection limit of fluorescence enhanced probe for acetaldehyde detection is 4.9 x 10-8mol/L, simple and convenient detection process, strong anti-interference capability, rapidness, sensitivity, accurate detection result and stronger practical application value.
(2) The mechanism of acetaldehyde recognition by the fluorescent probe P1 of the present invention is as follows: adding acetaldehyde into a recognition system containing a probe P1, and carrying out double condensation reaction on aldehyde groups in an acetaldehyde molecular structure and amino groups in a probe molecular structure to generate a fluorescent imine product P1-CH3CHO, releases a fluorescent signal. The product P1-CH was analyzed by high resolution mass spectrometry (HR-MS)3The structure of CHO was confirmed (FIG. 7). The experimental result shows that P1-CH3CHO theoretically calculates value [ M + H]+And [ M + Na]+295.1195 and 317.1014, respectively, and HR-MS results corresponding to 295.1189 and 317.1006, which corroborate the mechanism of action shown in FIG. 6.
Drawings
FIG. 1 is a graph showing fluorescence selectivity of a fluorescent probe P1 of the present invention, with an excitation wavelength of 440 nm;
FIG. 2 is an anti-interference graph of acetaldehyde recognized by fluorescent probe P1 of the present invention, with an excitation wavelength of 440 nm and an emission wavelength of 544 nm;
FIG. 3 is a graph showing the pH application range of acetaldehyde recognized by fluorescent probe P1 of the present invention, wherein the excitation wavelength is 440 nm and the emission wavelength is 544 nm;
FIG. 4 is a fluorescence titration chart of acetaldehyde recognized by the fluorescent probe P1 of the present invention, with an excitation wavelength of 440 nm;
FIG. 5 is a diagram showing the lowest detection limit of acetaldehyde recognized by the fluorescent probe P1 of the present invention, with an excitation wavelength of 440 nm and an emission wavelength of 544 nm;
FIG. 6 is a diagram showing the mechanism of acetaldehyde recognition by the fluorescent probe P1 of the present invention;
FIG. 7 is a high-resolution mass spectrum of the mechanism for identifying acetaldehyde by the fluorescent probe P1 of the present invention.
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, solvents, metal ions and the like used in the process of preparing the fluorescent probe P1 according to the present invention were purchased from Aladdin reagent company. Adopting a DTX-400 nuclear magnetic resonance spectrometer of Bruker company as a solvent, adopting deuterated chloroform and taking TMS as an internal standard to record a nuclear magnetic resonance hydrogen spectrum and a carbon spectrum in the process of confirming and testing the performance of the fluorescent probe P1; high resolution mass spectral data were recorded using a Q-exact HR-MS mass spectrometer from Thermo. The absorption spectra were recorded using the Cary100 uv-vis spectrophotometer from agilent.
Preparation of fluorescent Probe P1
A500 mL round bottom flask was charged with 2.76 g (10 mM) of 4-bromo-1, 8-naphthalic anhydride, and 300 mL of absolute ethanol. The mixture was refluxed with heating to suspend 4-bromo-1, 8-naphthalic anhydride in ethanol, and 5 mL of 80% hydrazine hydrate solution was added dropwise with stirring over 1 hour. Refluxing was continued for 12 h. Cooling to room temperature, filtering, washing the obtained solid with ethanol for 3 times, and separating by column chromatography (eluent volume ratio is CH)3OH:CH2Cl2= 1: 10), and 2.05 g of brick red solid can be obtained after vacuum drying. The yield was 85%.
Hydrogen nuclear magnetic resonance spectroscopy:1H NMR (400 MHz, DMSO, ppm) : 4.73 (s, 2 H), 5.75(s, 2 H), 7.27 (d, 1 H, J = 8.0 Hz), 7.67 (t, 1 H, J = 6.0 Hz), 8.32 (d, 1 H,J = 8.0 Hz), 8.45 (d, 1 H, J = 4.0 Hz), 8.66 (d, 1 H, J = 8.0 Hz), 9.24 (s, 1H)；
nuclear magnetic resonance carbon spectrum measurement:13C NMR (100 MHz, DMSO, ppm) : 160.66, 160.55,154.03, 134.87, 131.00, 128.77, 128.32, 124.64, 121.73, 118.99, 107.11,104.63;
high-resolution mass spectrometry: HR-MS m/z Calcd for C12H11N4O2 +([M+H+]+) 243.0882,found 243.0873 [M+H+]+。
Method for detecting acetaldehyde by fluorescence enhancement
Example 1
An acetaldehyde detection method based on a fluorescent probe comprises the following steps:
tris buffer solution with pH 7.4 and concentration 10 mM was prepared, mixed solution A was prepared with the above buffer solution and dimethyl sulfoxide (DMSO) in a volume ratio of 4:6, and probe P1 solution was prepared with DMSO at concentration 1 mM. The selectivity of probe P1 for acetaldehyde in mixed solution A was examined by fluorescence spectroscopy. As shown in FIG. 1, under the excitation condition at 440 nm, the probe P1(10 μ M) alone has weak fluorescence emission intensity at 544nm in the mixed solution A, and when acetaldehyde (10eq.) was added, the fluorescence emission intensity at 544nm was significantly increased, but when other substances (100 μ M) were added, the fluorescence emission intensity of the solution system was not significantly changed from that of the probe system alone.
The experimental results show that the probe P1 has good fluorescence specificity selectivity on acetaldehyde in the mixed solution A.
Example 2
An acetaldehyde detection method based on a fluorescent probe comprises the following steps:
a10 mM Tris buffer solution having a pH of 7.4 was prepared, a mixed solution A was prepared using the above buffer solution and DMSO in a volume ratio of 4:6, and a1 mM probe P1 solution was prepared using DMSO. 3000 μ L of mixed solution a and 30 μ L of DMSO solution of probe P1 were added to 19 clean fluorescence cuvettes, 10 molar equivalents of acetaldehyde and 10 molar equivalents of other analytes (various aldehydes, amino acids, peroxides, etc.) were added, and the mixture was detected by a fluorescence spectrometer, and a 544nm fluorescence intensity histogram corresponding to different analytes was plotted to obtain a fluorescence emission histogram (fig. 2).
Experiments prove that the probe P1 has better anti-interference performance on the recognition of acetaldehyde in the mixed solution A without being interfered by other analytes.
Example 3
An acetaldehyde detection method based on a fluorescent probe comprises the following steps:
preparing a Tris buffer solution with the pH of 4.3, 5.3, 6.3, 7.4, 8.2 and 9.4 and the concentration of 10 mM, preparing a mixed solution A1, A2, A3, A4, A5 and A6 with the volume ratio of 4:6 by using the buffer solution and DMSO, and preparing a probe P1 solution with the concentration of 1 mM by using the DMSO. Fluorescence emission intensity of the individual probe P1 (10. mu.M) and the probe P1 (10. mu.M) with acetaldehyde (10eq.) in the mixed solution A1-A6 was examined by a fluorescence spectrometer. As shown in FIG. 3, under the excitation condition at 440 nm, the single probe P1(10 μ M) has weak fluorescence emission intensity at 544nm in the mixed solution A with pH values of 4.3, 5.3, 6.3, 7.4, 8.2 and 9.4 respectively, and the fluorescence emission intensity is not greatly changed, and when acetaldehyde (10eq.) is added into the solution system, the fluorescence emission intensity at 544nm of the system is obviously enhanced.
The above experimental results show that the acetaldehyde identification by the probe P1 can be completed in a wider pH range, and the probe P1 has a better application range.
Example 4
An acetaldehyde detection method based on a fluorescent probe comprises the following steps:
a10 mM Tris buffer solution having a pH of 7.4 was prepared, a mixed solution A was prepared using the above buffer solution and DMSO in a volume ratio of 4:6, and a1 mM probe P1 solution was prepared using DMSO. Preparing 100 mu mol/L acetaldehyde solution with distilled water, adding 3 mL of mixed solution A and 30 mu L of DMSO solution of probe P1 into a clean fluorescence cuvette, gradually adding the acetaldehyde solution into the cuvette, respectively with the volumes of 0 mu L, 3 mu L, 6 mu L, 9 mu L, 12 mu L, 15 mu L, 18 mu L and 21 mu L, and simultaneously taking 440 nm as an excitation wavelength, measuring the fluorescence emission intensity at 544nm on a fluorescence spectrometer, taking the concentration of acetaldehyde as an abscissa and the fluorescence intensity at 544nm as an ordinate, and obtaining a working curve of the acetaldehyde concentration, wherein a linear regression equation is as follows: f544 nm=2215.496C +827.705, C being in μmol/L (drawing)4 and 5).
Application example
Minimum detection limit experiment:
good detection limits are one of the criteria for verifying whether a probe molecule has an application value. A10 mM Tris buffer solution having a pH of 7.4 was prepared, a mixed solution A was prepared using the above buffer solution and DMSO in a volume ratio of 4:6, and a1 mM probe P1 solution was prepared using DMSO. The concentration of the immobilized probe P1 is 10 mu M, the response intensity of the immobilized probe P1 to acetaldehyde with different concentrations is measured, the fluorescence emission intensity of the system is continuously enhanced at 544nm along with the increase of the acetaldehyde concentration, and the research finds that the linear range of the fluorescence emission intensity of the solution at the acetaldehyde concentration is 0-0.7 mu M (R)2= 0.993), and the detection limit of the probe molecule to acetaldehyde was calculated to be 4.9 × 10-8mol/L。
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (4)
1. A fluorescence probe-based acetaldehyde detection method is characterized by comprising the following steps:
(1) preparing a Tris buffer solution with the pH =7.4 and the concentration of 10 mM, and mixing the Tris buffer solution with dimethyl sulfoxide according to a proportion to obtain a mixed solution A; preparing a probe P1 solution with the concentration of 1 mM by using dimethyl sulfoxide as a solvent;
(2) preparing 100 mu mol/L acetaldehyde solution by using distilled water, adding the mixed solution A into a clean fluorescent cuvette, adding a probe P1 solution, and then sequentially adding the acetaldehyde solution, wherein the adding volumes are as follows: 0 μ L, 3 μ L, 6 μ L, 9 μ L, 12 μ L, 15 μ L, 18 μ L, 21 μ L, while taking 440 nm as the excitation wavelength, the fluorescence emission intensity at 544nm was measured on a fluorescence spectrometer, and a working curve based on the acetaldehyde concentration was obtained with the acetaldehyde concentration as abscissa and the fluorescence intensity at 544nm as ordinate, and the linear regression equation was: f544 nm=2215.496C +827.705, C being in μmol/L;
(3) adding the mixed solution A and the probe P1 solution into a clean fluorescent cuvette, sucking V mu L of sample solution to be detected by a microsyringe, adding the sample solution to be detected into the fluorescent cuvette containing the mixed solution A and the probe P1 solution, testing on a fluorescence spectrometer, substituting the measured 544nm fluorescence emission intensity into the linear regression equation in the step (2) to obtain the concentration C, and obtaining the concentration C of the sample to be detectedSample to be tested=3000 *C/V，CSample to be testedThe unit of (a) is mu mol/L;
the structure of the probe P1 is as follows:
2. the method of claim 1 for acetaldehyde detection based on a fluorescent probe, wherein: the volume ratio of the Tris buffer solution to the DMSO in the step (1) is 4: 6.
3. The method of claim 1 for acetaldehyde detection based on a fluorescent probe, wherein: the linear range of the concentration of the method for detecting acetaldehyde is 0-0.7 mu M, and the lowest detection limit is 4.9 multiplied by 10-8mol/L。
4. Use of the method for detecting acetaldehyde based on a fluorescent probe according to any one of claims 1 to 3 for detecting acetaldehyde in drinking wine, agricultural products.
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