CN114805178A - Fluorescent probe for detecting bisulfite ions, preparation thereof and application thereof in food detection - Google Patents
Fluorescent probe for detecting bisulfite ions, preparation thereof and application thereof in food detection Download PDFInfo
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- CN114805178A CN114805178A CN202210081364.1A CN202210081364A CN114805178A CN 114805178 A CN114805178 A CN 114805178A CN 202210081364 A CN202210081364 A CN 202210081364A CN 114805178 A CN114805178 A CN 114805178A
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- C07D209/56—Ring systems containing three or more rings
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- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
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- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
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- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
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- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
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Abstract
The application discloses a fluorescent probe for detecting bisulfite ions, a preparation method thereof and application thereof in food detection, wherein the structural formula of the fluorescent probe is shown as the formula (I):
Description
Technical Field
The application relates to the field of small molecule fluorescent probes, in particular to a bisulfite ion fluorescent probe with high signal-to-noise ratio, and preparation and application thereof in food detection.
Background
Bisulfite ion (HSO) is well known 3 - ) As a main existing form of sulfur dioxide, has superior antioxidant, preservative and antibacterial abilities, and is widely used in the pharmaceutical and food industries at present. In addition, sulfur-containing amino acids such as cysteine can also endogenously produce bisulfite ions in mammals. Recent studies have found that low concentrations of bisulfite ions have hypotensive, vasodilatory and antiatherogenic effects and are messengers in the cardiovascular system.
However, there is increasing evidence that abnormal bisulfite ion concentrations are associated with cardiovascular diseases and many neurological diseases, and are serious and even dangerous to human health. Many countries have strict control over the threshold of bisulfite ions in food and pharmaceutical products. Therefore, it is urgently required to develop a monitoring method of bisulfite ion with good selectivity and a high signal-to-noise ratio.
Disclosure of Invention
The application provides a bisulfite ion fluorescence probe of novel high signal-to-noise ratio, different with other bisulfite ion probes that have reported, this application the probe take place the addition reaction back with bisulfite ion, the product contains two naphthylamine derivatives that the structure is similar to realize the effect of two reinforcings of fluorescence intensity, improved the signal-to-noise ratio of probe detection bisulfite ion.
A fluorescent probe for detecting sulfite ions, wherein the structural formula of the fluorescent probe is shown as the formula (I):
a method of making a fluorescent probe as described, comprising:
mixing the compound (2), the compound (3), ethanol and piperidine to obtain a mixture, and heating the mixture under the protection of nitrogen to obtain a reaction solution; spin-drying the reaction liquid, separating and purifying to obtain the fluorescent probe with the structural formula shown in the formula (I);
optionally, the molar ratio of the compound (2), the compound (3) and the piperidine is 1: 1-1.2: 0.1.
optionally, the reaction conditions for heating the mixture under the protection of nitrogen are as follows: reacting for 6-10 hours at 60-80 ℃.
Alternatively, the separation and purification method may be as follows: concentrating the reaction solution under reduced pressure, and separating and purifying by silica gel column chromatography, wherein the volume ratio of the eluent is 20:1 dichloromethane: methanol to obtain the fluorescent probe (I).
Compound (2) of the present application is obtained commercially.
The compound (3) of the present invention is a disclosed compound, and its preparation method can be referred to in the literature (Zhu L, Fu M, Yin B, et al. A red-emitting fluorescent probe for mitochondria-target microviscosity in living cells and blood visual susceptibility in hyperglycemic detection [ J ]. Dyes and Pigments,2020,172: 107859).
After the high signal-to-noise ratio fluorescent probe and bisulfite ions are subjected to addition reaction, a conjugated system of probe molecules is destroyed to generate a product with two naphthylamine derivatives, so that the effect of turning on a blue fluorescent signal from off is achieved. Therefore, the fluorescent probe can be applied to qualitative or quantitative detection of the bisulfite ion concentration of the solution, and the detection reaction process is as follows:
based on the functional characteristics, the application also provides the application of the fluorescent probe in detecting the concentration of the bisulfite ions:
use of a fluorescent probe as described in the preparation of a product for detecting bisulfite ion concentration.
Optionally, the product is a test strip or a kit.
A kit for detecting sulfite ions comprises a fluorescent probe shown as a structural formula (I).
The fluorescent probe or the kit can be used for detecting the concentration of the bisulfite ions in the food.
A quantitative determination method of bisulfite ion concentration in food comprises:
and adding the fluorescent probe into the solution to be detected, carrying out mixing reaction, detecting the fluorescence intensity value of the reaction solution under the conditions that the excitation wavelength is 320nm and the emission wavelength is 475nm after the reaction is finished, substituting the fluorescence intensity value into a standard curve, and calculating to obtain the concentration of the hydrogen sulfite ions in the solution to be detected.
Optionally, the ratio of the concentration of the fluorescent probe in the solution to be detected to the concentration of the bisulfite ion is 5 μ M: 0 to 3 μ M. Within the range of the mixture ratio, the fluorescence intensity value and the concentration of the hydrogen sulfite ions in the solution to be detected form a linear relation.
Specifically, the standard curve is prepared as follows:
and (3) respectively putting 5 mu M of fluorescent probe and bisulfite ions in a solution of 0-3 mu M, collecting the fluorescence intensity of the solution under the excitation wavelength of 320nm and the emission wavelength of 475nm, and drawing by taking the fluorescence intensity as a vertical coordinate and the bisulfite ions in the solution as a horizontal coordinate to obtain a linear standard curve.
Optionally, the linear equation of the linear standard curve is: 254.19c +24.819 (R) 2 0.994), wherein F is the fluorescence intensity of the reaction solution at 475nm, and c is the concentration of hydrogensulfite ion in the reaction solution in μ M.
Optionally, when the concentration of sulfite ions in the solution to be detected is detected, the pH value of the solution is 7.4.
Compared with other detection methods, the fluorescent probe is used for detecting the bisulfite ion component in the food due to the advantages of simple preparation method, high detection speed and the like. The research and development of novel bisulfite ion fluorescent probe with high signal-to-noise ratio has urgent practical significance
Compared with the prior art, the invention has the beneficial effects that:
(1) the preparation method of the fluorescent probe provided by the invention is simple;
(2) the fluorescence characteristic of the application improves the signal-to-noise ratio of the probe for detecting the bisulfite ions, and can be used for detecting the concentration of the bisulfite ions in a food sample;
drawings
FIG. 1 shows nuclear magnetic hydrogen spectra of the fluorescent probe (I) prepared in example 1.
FIG. 2 shows nuclear magnetic carbon spectrum of the fluorescent probe (I) prepared in example 1.
FIG. 3 is a graph showing the change in the fluorescence intensity of the reaction with bisulfite ion of probe (I) prepared in example 1 at pH 7.4 depending on the concentration of bisulfite ion.
FIG. 4 is a standard curve of probe (I) prepared in example 1 at an excitation wavelength of 320nm and an emission wavelength of 475 nm.
FIG. 5 is a graph showing the measurement of interference rejection at an excitation wavelength of 320nm and an emission wavelength of 475nm for the probe (I) prepared in example 1. .
Detailed Description
The technical solutions in the embodiments of the present application will be described clearly and completely with reference to the drawings in the embodiments of the present application, and it is obvious that the described embodiments are only some embodiments of the present application, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present application.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this application belongs. The terminology used herein in the description of the present application is for the purpose of describing particular embodiments only and is not intended to be limiting of the application.
Example 1: preparation of fluorescent Probe (I) with high Signal-to-noise ratio
Compound (2) (0.5mmol) and compound (3) (0.5mmol) were placed in a round bottom flask, followed by the addition of 5mL acetonitrile and piperidine (0.05mmol) and the mixture was heated under nitrogen for 8 hours at 70 ℃. And (3) spin-drying the reaction liquid, and separating and purifying by using a silica gel column chromatography, wherein a developing agent is dichloromethane: methanol 20:1 (vol.%), fluorescent probe (I) was prepared with a high signal-to-noise ratio (0.1g, 39.5% yield).
The synthetic route is as follows:
the nuclear magnetic hydrogen spectrum and the nuclear magnetic carbon spectrum of the fluorescent probe (I) with the high signal-to-noise ratio are shown in the figure 1 and the figure 2 respectively.
1 H NMR(400MHz,DMSO-d 6 )δ8.63–8.52(m,2H),8.43(d,J＝8.5Hz,1H),8.28(d,J＝8.9Hz,1H),8.25–8.17(m,2H),8.08(d,J＝8.8Hz,1H),7.88(d,J＝9.1Hz,1H),7.83–7.76(m,2H),7.71(t,J＝7.5Hz,1H),7.64(d,J＝16.1Hz,1H),7.32(dd,J＝9.1,2.5Hz,1H),7.04(d,J＝2.5Hz,1H),4.29–4.20(m,3H),3.14(s,6H),2.05(s,6H). 13 C NMR(101MHz,DMSO-d 6 )δ182.13,153.33,151.25,140.01,138.12,137.84,135.78,133.40,131.37,131.22,130.49,128.79,128.35,127.29,127.22,125.55,125.08,123.52,116.99,113.57,109.71,105.86,53.75,34.95,27.40,25.98.
Example 2: the fluorescence intensity of the fluorescent probe (I) (prepared in example 1) reacted with bisulfite ion at pH 7.4 varied with the concentration of bisulfite ion.
A certain amount of the fluorescent probe (I) was weighed accurately, a probe stock solution with a concentration of 0.5mM was prepared using dimethyl sulfoxide, 10. mu.L of the probe stock solution was pipetted into 0.49mL of PBS buffer containing bisulfite ions at different concentrations (final values of sulfite ion were 0. mu.M, 0.6. mu.M, 0.8. mu.M, 1. mu.M, 1.5. mu.M, 2. mu.M, 2.5. mu.M, 3. mu.M, 4. mu.M, 5. mu.M, 8. mu.M, 10. mu.M, 15. mu.M, 20. mu.M, 30. mu.M, 40. mu.M, 50. mu.M, 80. mu.M, and 100. mu.M, and added to a 96-well plate, and the fluorescence emission spectrum of the compound (I) was measured using a multifunctional microplate reader.
As can be seen from FIG. 3, the fluorescent probe (I) has no emission peak in the range of 420-560nm in the PBS buffer when excited at 320 nm; as the concentration of the bisulfite increases, the emission intensity of the fluorescent probe (I) at 420-560nm is increased, which indicates that the probe has the capacity of identifying sulfite ions. Under the condition that the excitation wavelength is 320nm, when the concentration of bisulfite ions in the solution is increased from 0 muM to 100 muM, the fluorescence intensity value at 475nm is enhanced by about 350 times, which is in line with the phenomenon of high signal-to-noise ratio detection.
In addition, under the condition that the excitation wavelength is 320nm, a linear standard curve is obtained by drawing with the numerical value of the fluorescence intensity value at 475nm as the ordinate and the concentration of sulfite ions as the abscissa, and the standard curve is shown in figure 4. From the linear relationship chart, it can be found that in the range of 0-3 μ M of the concentration of sulfite ions, the two have a good linear relationship, and the linear equation: 254.19c +24.819 (R) 2 0.994), it was demonstrated that the fluorescent probe (I) detects qualitatively or quantitatively the concentration of sulphite ions in solution by a change in fluorescence intensity at 475 nm.
Example 3: measurement of interference rejection capability of fluorescent probe (I) (prepared in example 1).
Accurately weighing a certain amount of fluorescent probe (I), preparing a probe mother solution with the concentration of 0.5mM by using dimethyl sulfoxide, sucking 10 mu L by a pipette, adding the probe mother solution into 0.49mL of PBS solution containing different analytes (1-17 are bisulfite ions, potassium ions, copper ions, magnesium ions, zinc ions, fluorine ions, iodide ions, nitrite ions, acetate ions, calcium ions, L-cysteine, glutathione, DL-homocysteine, L-serine, L-arginine, L-lysine and L-leucine respectively, the final concentration is 100 mu M), and testing the fluorescence intensity of the probe mother solution at 475nm by using a multifunctional microplate reader, wherein the fluorescence excitation wavelength is 320 nm.
The fluorescence spectrum is shown in FIG. 5. Experimental results show that the influence of the addition of other analytes except bisulfite ions on the fluorescence intensity of the probe (I) is small, and the probe is proved to have good anti-interference capability.
Example 4: use of the fluorescent probe (I) (prepared in example 1) for detection in food samples.
In order to research the application of the probe (I) in the food field, the probe is applied to the content test of the hydrogen sulfite ions in the white granulated sugar. First, 1g of white granulated sugar is accurately weighed and dissolved in 100mL of buffer (PBS buffer with pH 7.4), 250 μ L of the buffer solution and 240 μ L of the buffer solution are sucked by a pipette gun and mixed, 10 μ L of probe stock solution with a concentration of 0.5mM is added, after a while, the fluorescence intensity at 475nm is tested, and the bisulfite ion content in the solution is calculated according to the linear standard curve of fig. 4. The concentration of sodium bisulfite in the white granulated sugar is actually measured to be 0.524 mu M. In addition, the result of adding bisulfite ion of 2.0. mu.M to the sample by the standard recovery method is shown in Table 1.
TABLE 1 Probe 1 detection of bisulfite ion content in white sugar
The experimental result shows that the probe (I) can be used for detecting the content of bisulfite ions in food.
The above-mentioned embodiments only express several embodiments of the present application, 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 concept of the present application, which falls within the scope of protection of the present application. Therefore, the protection scope of the present patent shall be subject to the appended claims.
Claims (10)
1. A fluorescent probe for detecting sulfite ions is characterized in that the structural formula of the fluorescent probe is shown as formula (I):
2. use of the fluorescent probe according to claim 1 for the preparation of a product for detecting bisulfite ion concentration.
3. The use according to claim 2, wherein the product is a test strip or kit.
4. A kit for detecting sulfite ions, comprising the fluorescent probe of claim 1.
5. Use of the fluorescent probe according to claim 1 or the kit according to claim 4 for detecting the concentration of bisulfite ions in food.
6. A quantitative detection method for bisulfite ion concentration in food, which is characterized by comprising the following steps:
adding the fluorescent probe of claim 1 into the solution to be tested, mixing and reacting, detecting the fluorescence intensity value of the reaction solution at an excitation wavelength of 320nm and an emission wavelength of 475nm after the reaction is finished, substituting into the standard curve, and calculating to obtain the concentration of the hydrogen sulfite ions in the solution to be tested.
7. The quantitative determination method according to claim 6, wherein the ratio of the final concentration of the fluorescent probe to the concentration of bisulfite ions in the solution to be measured is determined in accordance with a ratio of 5 μ M: 0 to 3 μ M.
8. The method of preparing a fluorescent probe according to claim 1, comprising:
mixing the compound (2), the compound (3), ethanol and piperidine to obtain a mixture, and heating the mixture under the protection of nitrogen to obtain a reaction solution; spin-drying the reaction liquid, separating and purifying to obtain the fluorescent probe with the structural formula shown in the formula (I);
9. the method according to claim 8, wherein the molar ratio of the compound (2), the compound (3) and the piperidine is 1: 1-1.2: 0.1; the reaction conditions for heating the mixture under nitrogen protection were: reacting for 6-10 hours at 60-80 ℃.
10. The preparation method according to claim 8, wherein the separation and purification method comprises: concentrating the reaction solution under reduced pressure, and separating and purifying by silica gel column chromatography, wherein the volume ratio of the eluent is 20:1 dichloromethane: methanol.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116621759A (en) * | 2023-05-31 | 2023-08-22 | 济南大学 | Fluorescent probe for double detection of peroxynitroso and sulfur dioxide and application thereof |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116621759A (en) * | 2023-05-31 | 2023-08-22 | 济南大学 | Fluorescent probe for double detection of peroxynitroso and sulfur dioxide and application thereof |
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