CN111521593A - Rapid visual detection method based on water-soluble perylene bisimide derivative - Google Patents
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Abstract
The invention relates to the field of folic acid detection, and discloses a rapid visual detection method based on a water-soluble perylene bisimide derivative. Specifically, disclosed is a method for detecting folic acid, which uses perylene bisimide derivatives with the structure shown in formula (I) as a probe. The perylene bisimide derivative has good water solubility, and can realize high-sensitivity, specificity and visual folic acid detection. The detection method provided by the invention has higher detection efficiency and sensitivity.
Description
Technical Field
The invention relates to the technical field of biological detection, in particular to a rapid visual detection method based on a water-soluble perylene bisimide derivative.
Background
Folic acid, also known as acyl glutamic acid, is a water-soluble B-group vitamin widely found in some fresh fruits, green vegetables, animal livers and beans. It is a cofactor for one carbon unit and plays an important role in maintaining many biochemical processes in the growth and metabolism of the human body. Many studies have demonstrated that folate deficiency can lead to physiological dysfunction and symptoms of certain diseases, such as megaloblastic anemia, neurodegenerative diseases, neonatal neural tube malformations, osteoporosis, and the like.
At present, folate deficiency is considered a worldwide health problem and the World Health Organization (WHO) has clearly defined recommended daily folate intakes. With health concerns, folic acid is added to a variety of special dietary and health foods. Therefore, the rapid and accurate detection of folic acid in food has important significance for guiding the intake of folic acid and ensuring the safety and effectiveness.
Disclosure of Invention
In view of the above, the technical problem to be solved by the present invention is to provide a rapid visual detection method based on a water-soluble perylene bisimide derivative, and specifically to disclose a method for detecting folic acid, which overcomes the defects of low detection efficiency and low sensitivity in the existing method for detecting folic acid.
In order to achieve the above object, the present invention provides the following technical solutions:
the invention provides an application of perylene bisimide derivative shown as a formula (I) in folic acid detection:
the perylene bisimide derivative with the structure shown in the formula (I) has good water solubility, can realize high-sensitivity and specific folic acid detection, and has obvious specificity and anti-interference capability in detection.
The conformation and aggregation state of the perylene bisimide derivative with the structure shown in the formula (I) in the invention show different states to external stimuli, and further cause the change of the optical characteristics of the perylene bisimide derivative, such as the change of the solution color and the opening or quenching phenomenon of fluorescence.
Therefore, when the perylene bisimide derivative is used for detecting folic acid, the effect of fluorescence response can be realized, namely, the fluorescence of the perylene bisimide derivative is quenched, and the quenching effect can be seen by naked eyes under the irradiation of an ultraviolet lamp.
In addition, the detection limit of the perylene bisimide derivative is as low as 29.2nmol/L, the visual effect in the solution is obvious, and the visual detection limit is as low as 6 mu mol/L.
The perylene bisimide derivative provided by the invention has excellent folic acid detection performance, and may be based on the following principle: the perylene bisimide derivative and the folic acid can be identified through multiple non-covalent interactions, and the perylene bisimide derivative and the folic acid form stable supramolecular aggregates in an aqueous solution, so that the fluorescent signal of the probe is changed.
The source of the perylene imide derivative having the structure represented by the formula (I) is not particularly limited in the present invention, and the perylene imide derivative can be generally commercially available or can be prepared by a method known to those skilled in the art.
In order to obtain the perylene bisimide derivative with the structure shown in the formula (I) with higher quality and yield, the invention provides a preferable preparation method for preparing the perylene bisimide derivative with the structure shown in the formula (I), specifically:
secondly, the invention provides a preparation method of the perylene bisimide derivative, which comprises the following steps:
(1) carrying out a first contact reaction on a compound shown in a formula (II) and a compound shown in a formula (III) to obtain a compound shown in a formula (IV);
(2) in the presence of a solvent, carrying out a second contact reaction on the compound shown in the formula (IV), formaldehyde and formic acid to obtain a compound shown in a formula (V);
(3) in the presence of a solvent, carrying out a third contact reaction on the compound shown in the formula (V), methanol, sodium carbonate and methyl iodide to obtain a compound shown in a formula (I);
the present invention is not particularly limited with respect to the origin of the compound represented by the formula (II), and may be obtained, for example, by commercially available methods or by synthesis using methods provided in the prior art.
Preferably, the conditions of the first contact reaction include: the reaction is carried out for 24 hours at the reaction temperature of 90-110 ℃ and then for 4 hours at the temperature of 120 ℃.
Preferably, the conditions of the second contact reaction include: stirred at room temperature for 1h and then heated at 110-.
Preferably, the conditions of the third contact reaction include: stirring at room temperature for 12h, adding methyl iodide, heating to 50-70 deg.C, preferably 60 deg.C, and reacting for 12 h.
Preferably, the first contact reaction further comprises: the obtained reaction mixture is subjected to solvent removal treatment and first precipitation treatment in sequence to obtain the compound shown in the formula (IV).
Preferably, the first precipitation treatment specifically includes:
the crude product solid obtained after the solvent removal treatment is washed by toluene and ethyl acetate respectively and then dried in vacuum.
Preferably, the second contact reaction further comprises: the obtained reaction mixture is subjected to solvent removal treatment and second precipitation treatment in sequence to obtain the compound shown in the formula (V).
Preferably, the second precipitation treatment specifically includes:
the crude solid obtained after the solvent removal treatment is washed by anhydrous ether and then dried in vacuum.
Preferably, the third contact reaction further comprises: the obtained reaction mixture is subjected to solvent removal treatment and third precipitation treatment in sequence to obtain the compound shown in the formula (I).
Preferably, the third precipitation treatment specifically includes:
the crude solid obtained after the solvent removal treatment is washed by anhydrous ether and then dried in vacuum.
Thirdly, the invention provides a reagent, test paper or kit for detecting folic acid, which comprises the perylene bisimide derivative or the perylene bisimide derivative prepared by the preparation method.
Fourthly, the invention provides a rapid visual detection method based on the water-soluble perylene bisimide derivative, in particular to a method for detecting folic acid, wherein the perylene bisimide derivative or the perylene bisimide derivative prepared by the preparation method is used as a probe.
Preferably, the concentration of the probe is 3. mu. mol/L.
Specifically, the detection method of the invention comprises the following steps: the spectrum of folic acid was measured at the probe concentration of 3. mu. mol/L in 1mmol/L Tris buffer (pH 9.0), the excitation wavelength was 498nm for detection, and the slit width for excitation and emission was 5.0 nm. And (3) selecting the fluorescence intensity at the position with the emission wavelength of 548nm to calculate the fluorescence quenching efficiency of the probe, and establishing a detection standard curve by taking the concentration of folic acid as a horizontal coordinate and the fluorescence quenching efficiency of the probe as a vertical coordinate. Visual detection of folic acid was performed in 1mmol/L Tris buffer at pH 9.0 at the probe concentration of 10. mu. mol/L, and fluorescence quenching was visually recognized by the probe under irradiation of an ultraviolet lamp.
Compared with the prior art, the invention provides a rapid visual detection method based on water-soluble perylene bisimide derivatives, which takes the perylene bisimide derivatives with the structure shown in the formula (I) as a probe. The perylene bisimide derivative has good water solubility, and can realize high-sensitivity and specific detection of folic acid. The detection method provided by the invention has higher detection efficiency and sensitivity.
Drawings
FIG. 1 shows the fluorescence quenching efficiency (. lamda.mol/L) of perylene imide derivative probes (3. mu. mol/L) after different concentrations of folic acid were added to Tris buffer (1mmol/L pH 9.0)ex＝498nm，λem＝548nm)；
FIG. 2 shows the relative fluorescence intensity of perylene imide derivative probe (10. mu. mol/L) and different substances (10. mu. mol/L) in Tris buffer (pH 9.0: 1 mmol/L) ((M))λex＝498nm，λem548nm), (1-blank, 2-folic acid, 3-serine, 4-threonine, 5-glycine, 6-phenylalanine, 7-glutamic acid, 8-histidine, 9-nicotinic acid, 10-vitamin C, 11-vitamin B6, 12-vitamin B1,13-K+,13-Cl-,14-Ca2+,15-Mg2+,16-Na+,17-NO3 -,18-H2PO4 -,19-SO4 2-,20-CO3 2-)；
FIG. 3 shows the fluorescence change of perylene imide derivative probe (10. mu. mol/L) under UV irradiation after different concentrations of FA (0,2,4,6,8,10,15, 20. mu. mol/L) are added;
FIG. 4 shows the fluorescence change of perylene imide derivative probe (10. mu. mol/L) under UV irradiation after adding different substances (10. mu. mol/L) (1-blank, 2-folic acid, 3-serine, 4-threonine, 5-glycine, 6-phenylalanine, 7-glutamic acid, 8-histidine, 9-nicotinic acid, 10-vitamin C, 11-vitamin B6, 12-vitamin B1, 13-K)+,13-Cl-,14-Ca2+,15-Mg2+,16-Na+,17-NO3 -,18-H2PO4 -,19-SO4 2-,20-CO3 2-)；
FIG. 5 shows the fluorescence quenching efficiency (. lamda.mol/L) of perylene imide derivative probes (3. mu. mol/L) after addition of different concentrations of folic acid to Tris buffer containing 10% fetal bovine serum (pH 9.0 at 1 mmol/L)ex＝498nm，λem＝548nm)。
Detailed Description
In order to further illustrate the present invention, the following examples are provided to describe the method for rapid visual detection based on water-soluble perylene imide derivatives in detail.
Preparation of a substance for use:
preparation of a buffer: weighing Tris solid, preparing into 500mL Tris buffer solution with the concentration of 1mmol/L by using distilled water, and adjusting the pH value to 9.0 by using 1mol/L sodium hydroxide standard solution. Storing in a refrigerator at 4 deg.C.
Preparing a probe mother solution: the solid of formula (I) is weighed out, prepared into a mother liquor with the concentration of 1mmol/L by using distilled water, and subpackaged into solutions with the same volume for standby in small bottles. For the spectroscopic measurement, the sample was diluted to a predetermined concentration with a prepared Tris buffer (1mmol/L, pH 9.0) and used for the measurement.
Preparing a to-be-detected object and an interferent: the folic acid is prepared into stock solution with the concentration of 1mmol/L by distilled water for standby. Other interfering substances were prepared into 1mmol/L stock solutions with distilled water. These solutions were stored in a refrigerator at 4 ℃ until use.
Preparation of actual samples: folic acid tablets were produced by beijing mihaidi pharmaceutical company ltd, and 5 folic acid tablets (0.4 mg × 31 tablets/bottle, mass of each tablet about 0.125g) were dissolved in 10mL of ultrapure water, sonicated at 40 ℃ for 4 minutes, and the whole substance was transferred to a 25mL volumetric flask to a constant volume, filtered through a 0.22 μm microporous membrane, and the filtrate was used for the experiment.
Example 1
Preparation of the compound of formula (I). 784mg of perylene anhydride was reacted with 6mL of tris (2-aminoethyl) amine, stirred at 100 ℃ for 24h, and then reacted at 120 ℃ for 4 h. After the reaction, the reaction mixture was cooled to room temperature, and ethanol/diethyl ether (1:3) was added to precipitate the product, which was then filtered off with suction. After suction filtration, the reaction mixture was washed three times with toluene and ethyl acetate, respectively, and vacuum-dried at 40 ℃ to obtain the compound of (IV). 276mg of the substance described In (IV) was taken, and 1.28mL of 85% formic acid and 0.88mL of 30% formaldehyde were added thereto, stirred at room temperature for 1 hour, and then heated at 120 ℃ for 16 hours. After cooling to room temperature, 30mL of anhydrous ether was added for washing, and washing was repeated 3 times to obtain the compound of (V). 150mg of the compound described in (V) was added with 6mL of methanol and 100m of sodium carbonate, stirred at room temperature for 12 hours, then added with 0.3mL of methyl iodide, heated to 60 ℃ and reacted for 12 hours. After cooling to room temperature, 40mL of anhydrous ether was added and the mixture was washed and repeated for 3 times to obtain the compound represented by (I) (hereinafter referred to as probe or perylene imide derivative).
It is characterized as follows:1H NMR(400MHz,CF3COOD)8.88(d,8H),4.97(s,4H),4.43(s,20H),4.18(s,6H),3.48(s,36H)。13C-NMR(100MHz,CF3COOD),ppm：166.0,136.7,133.2,129.6,126.6,124.5,121.6,59.2,54.3,54.1,53.6,48.5,47.3,35.2。
the probe is well soluble in water, and can be dissolved by adding water.
Example 2
Measurement of fluorescence spectra：
Mixing 3 μ L of probe mother liquor and 950 μ L of 1mmol/L Tris buffer solution, adding into 1mL sample cell, mixing well, measuring fluorescence spectrum of probe buffer solution, and recording fluorescence intensity I under 548nm0. And then gradually adding folic acid with a certain concentration gradient into the sample cell, uniformly mixing, measuring the corresponding fluorescence spectrum, and recording the fluorescence intensity I under 548 nm.
The results are shown in fig. 1 (that is, fig. 1 shows the degree of quenching of fluorescence of the perylene imide derivative at 548nm with folic acid concentration in Tris (1mmol/L, pH 9.0) buffer0-I)/I0]×100％，λexThe slit width of the excitation and emission light was 5.0nm at 498 nm. )
The perylene bisimide derivative is excited under the excitation wavelength of 498nm, a maximum emission peak at 548nm is emitted, the fluorescence emission intensity of the perylene bisimide derivative is gradually reduced along with the addition of folic acid, and when the concentration of folic acid is dropwise added to 4 mu mol/L, the quenching degree of the perylene bisimide derivative reaches 90%. According to the estimation method of the detection limit, the detection limit of the perylene bisimide derivative to the folic acid is 29.2 nmol/L.
Example 3
Selectivity study:
selecting common interferents for detecting folic acid, including thiamine (vitamin B)1) Vitamin B6Vitamin C, nicotinic acid, glutamic acid, phenylalanine, glycine, histidine, serine, threonine and Na+、K+、Ca2+、Mg2+、Cl-、SO4 2-、CO3 2-、NO3 -、H2PO4 -. In the test, the concentration of the perylene bisimide derivative is 3 mu mol/L, and the concentration of all interferents is 10 mu mol/L, and the fluorescence spectrum test is carried out under the same test conditions. Before adding interferentsThe absorption value of the perylene bisimide derivative at 548nm is taken as the ratio, I0the/I is used as a parameter for measuring the influence degree of the perylene bisimide derivative on the substance to be measured.
The results are shown in fig. 2 (i.e., fig. 2 shows a graph of relative absorption values of the perylene imide derivatives with folic acid and other interferents in Tris (1mmol/L, pH 9.0) buffer).
As can be seen from the figure, I of all other substances except folic acid0I ≈ 1, and I of folic acid0The result shows that the perylene imide derivative has excellent selectivity on folic acid, wherein I is 16.8, which is far higher than other compounds.
Example 4
Visual detection：
The concentration of the perylene bisimide derivative is 10 mu mol/L, and folic acid with different concentrations is added.
FIG. 3 is a photograph of different concentrations of folic acid under 365nm UV light, and it can be seen that as the concentration of folic acid increases, the corresponding solution fluorescence gradually darkens from yellow to complete quenching, with a limit of 6. mu. mol/L for visual detection.
Example 5
In order to more intuitively observe the effect graph after interaction of the perylene bisimide derivative and folic acid and interferents thereof, the fluorescence change of the solution in the selective folic acid investigation process of the perylene bisimide derivative in the aqueous solution is monitored under the irradiation of a 365nm ultraviolet lamp.
Selecting folic acid and the interfering substance, as shown in FIG. 4, when 10 μmol/L of the interfering substance is added to 10 μmol/L of the perylene imide derivative, the fluorescence of the solution is not changed, and when folic acid is added, the fluorescence of the solution is strongly quenched.
Example 6
Application of actual samples：
To verify the feasibility of this detection method in real samples, folic acid tablets were selected for recovery determination.
The spiked recoveries after addition of 0.25. mu. mol/L and 0.50. mu. mol/L folic acid were 101.4% and 101.0%, respectively (RSD < 6%), with results indicating better accuracy of the method.
Example 7
The detection of folic acid under physiological conditions is researched by selecting fetal calf serum, and the detection method and indexes are similar to those of the detection steps.
FIG. 5 shows the fluorescence response of folate titration in Tris buffer containing 10% fetal calf serum. The good linearity is found in the range of 1.0-10 mu mol/L, which indicates that the perylene bisimide derivative can be used for quantitative detection of folic acid under physiological conditions to a certain extent.
From the above results, it is understood that the perylene imide derivative having the structure represented by the formula (I) of the present invention has good water solubility, and can detect folic acid with high sensitivity and specificity, and can perform visual detection of folic acid.
The above description of the embodiments is only intended to facilitate the understanding of the method of the invention and its core idea. It should be noted that, for those skilled in the art, it is possible to make various improvements and modifications to the present invention without departing from the principle of the present invention, and those improvements and modifications also fall within the scope of the claims of the present invention.
Claims (9)
1. The perylene bisimide derivative shown as the formula (I) is applied to the detection of folic acid;
2. a method for detecting folic acid is characterized in that perylene bisimide derivatives shown in a formula (I) are used as probes;
3. a reagent, test paper or kit for detecting folic acid is characterized by comprising a perylene bisimide derivative shown as a formula (I);
4. the use according to claim 1, or the method according to claim 2, or the reagent, test paper or kit according to claim 3, wherein the perylene imide derivative according to formula (I) is prepared according to the following method:
(1) carrying out a first contact reaction on a compound shown in a formula (II) and a compound shown in a formula (III) to obtain a compound shown in a formula (IV);
(2) in the presence of a solvent, carrying out a second contact reaction on the compound shown in the formula (IV), formaldehyde and formic acid to obtain a compound shown in a formula (V);
(3) in the presence of a solvent, carrying out a third contact reaction on the compound shown in the formula (V), methanol, sodium carbonate and methyl iodide to obtain a compound shown in a formula (I);
5. the use, method, reagent, strip or kit according to claim 4, wherein the conditions of the first contact reaction comprise: the reaction is carried out for 24 hours at the reaction temperature of 90-110 ℃ and then for 4 hours at the temperature of 120 ℃.
6. The use, method, reagent, strip or kit according to claim 4, wherein the conditions of the second contact reaction comprise: stirred at room temperature for 1h and then heated at 110-130 ℃ for 16 h.
7. The use, method, reagent, strip or kit according to claim 4, wherein the conditions of the third contact reaction comprise: stirring at room temperature for 12h, adding methyl iodide, heating to 50-70 deg.C, and reacting for 12 h.
8. The use, method, reagent, strip or kit according to claim 4, further comprising after said first contact reaction: sequentially carrying out solvent removal treatment and first precipitation treatment on the obtained reaction mixture to obtain a compound shown as a formula (IV);
after the second contact reaction, the method further comprises the following steps: sequentially carrying out solvent removal treatment and second precipitation treatment on the obtained reaction mixture to obtain a compound shown as a formula (V);
after the third contact reaction, the method further comprises the following steps: the obtained reaction mixture is subjected to solvent removal treatment and third precipitation treatment in sequence to obtain the compound shown in the formula (I).
9. The use, method, reagent, strip or kit according to claim 4, wherein said first precipitation treatment comprises in particular:
respectively cleaning the crude product solid obtained after the solvent removal treatment with toluene and ethyl acetate, and then carrying out vacuum drying;
the second precipitation treatment specifically comprises:
washing the crude product solid obtained after the solvent removal treatment with anhydrous ether, and then drying in vacuum;
the third precipitation treatment specifically includes:
the crude solid obtained after the solvent removal treatment is washed by anhydrous ether and then dried in vacuum.
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| CN114249727A (en) * | 2021-09-28 | 2022-03-29 | 中国农业大学 | Fluorescence rapid visual detection method of perfluorooctane sulfonate based on cationic perylene bisimide |
| CN114874211A (en) * | 2022-03-30 | 2022-08-09 | 西安交通大学 | Imide derivative, preparation method and application in flow battery |
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| CN114874211B (en) * | 2022-03-30 | 2023-09-26 | 西安交通大学 | Imide derivative, preparation method and application thereof in flow battery |
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