A supermolecular fluorescent probe for recognizing norfloxacin and preparation and application thereof

Abstract

The application discloses a supramolecular fluorescent probe for selectively recognizing norfloxacin and a preparation and application thereof. The supramolecular fluorescent probe is prepared from a Cucurbit [8] uril and a guest G; a specific method is as follows: the guest G is weighed, dissolved in water and prepared into a solution A; the Cucurbit [8] uril is weighed, dissolved in water and prepared into a solution B; the solution A and the solution B are mixed and diluted, and are fully shaken to obtain the supramolecular fluorescent probe for selectively recognizing norfloxacin. The supramolecular fluorescent probe can selectively recognize norfloxacin in a water system, and has the characteristics of simple preparation, convenient detection, sensitive detection, low detection cost and strong selectivity.

Description

TECHNICAL FIELD

[0001] The present application relates to a fluorescent probe and its preparation and application, in particular to a supramolecular fluorescent probe for selective recognition of norfloxacin and its preparation and application. BACKGROUND

[0002] Norfloxacin (NOF) as the third generation of quinolone antibiotics, not only has a positive inhibitory effect on cell DNA cyclase, but also can prevent DNA replication, kill skin epidermis bacteria, treat skin infections and other effects, and is widely used in aquaculture.

[0003] But because of its excessive use has caused serious pollution to human life and the ecological system of the environment, and it is necessary to conduct irregular detection on the polluted environment.

[0004] The fluorescent probe detection is a new type of chemical detection means, which has a series of advantages such as convenient operation, no need for pretreatment, no damage to the sample, low cost and no influence of external electromagnetic field, and is widely used in the field of chemical detection. However, due to the low solubility of the probe molecule in aqueous solution, and the lack of appropriate complementary binding sites between the antibiotic molecule and the fluorescent chemical sensor, the selective recognition and detection of antibiotic molecules is a difficulty and hotspot in the field of supramolecular chemistry and analytical chemistry.

[0005] And the main potential application field of the fluorescent probe is the biological, medical and environmental monitoring in water system, so the detection in aqueous solution has potential application value. SUMMARY

[0006] The present application provides a supramolecular fluorescent probe for selective recognition of norfloxacin and its preparation and application, in order to solve the above technical problems. The supramolecular fluorescent probe of the present application can selectively recognize norfloxacin in water system, and has the characteristics of simple preparation, convenient detection, sensitive detection, low detection cost and strong selectivity.

[0007] The technical scheme of the present application is a supramolecular fluorescent probe for selective recognition of norfloxacin, and its chemical structure is as follows:

[0008]

[0009] Among them is an eight-membered cucurbituril.

[0010] A preparation method of the supramolecular fluorescent probe for selective recognition of norfloxacin according to the foregoing is prepared from eight-membered cucurbituril and guest G; wherein the molecular formula of the guest G is C 29 H 24 N2O2 2+ , and the chemical structure is as shown in the following formula:

[0011]

[0012] In a preferred embodiment, the above-mentioned method for preparing a supramolecular fluorescent probe for selective recognition of norfloxacin comprises the following steps:

[0013] (1) Weigh the guest G, dissolve it in water to prepare solution A;

[0014] (2) Weigh the cucurbit [8] uril, dissolve it in water to prepare solution B;

[0015] (3) Mix and dilute solution A and solution B, shake well to obtain the supramolecular fluorescent probe for selective recognition of norfloxacin.

[0016] In a preferred embodiment, the above-mentioned method for preparing a supramolecular fluorescent probe for selective recognition of norfloxacin, the concentration of solution A is 0.5x10 -3 mol·L -1 -1.5x10 -3 mol·L -1 .

[0017] In a preferred embodiment, the above-mentioned method for preparing a supramolecular fluorescent probe for selective recognition of norfloxacin, the concentration of solution B is 0.5x10 -4 mol·L -1 -1.5x10 -4 mol·L -1 .

[0018] In a preferred embodiment, the above-mentioned method for preparing a supramolecular fluorescent probe for selective recognition of norfloxacin, when mixing solution A and solution B, the mixing molar ratio of cucurbit [8] uril to guest G is 1:0.5-1.5.

[0019] In a preferred embodiment, the above-mentioned method for preparing a supramolecular fluorescent probe for selective recognition of norfloxacin, after mixing solution A and solution B, dilute to 0.5x10 -5 mol·L -1 -1.5x10 -5 mol·L -1 .

[0020] An application of the above-mentioned supramolecular fluorescent probe in selective recognition of norfloxacin.

[0021] In a preferred embodiment, the above-mentioned application of the supramolecular fluorescent probe in selective recognition of norfloxacin is to drop the sample to be recognized into the supramolecular fluorescent probe to obtain a sample solution, and to excite the fluorescence of the sample solution and test the fluorescence wavelength of the excited fluorescence.

[0022] In the preferred scheme, the aforementioned supramolecular fluorescent probe is applied to selective recognition of norfloxacin, the excitation wavelength of the fluorescence excitation is 349 nm; when the sample to be recognized is added and norfloxacin is recognized, the maximum emission wavelength of the fluorescence of the reagent is 558 nm.

[0023] Advantages of the present application

[0024] 1. The supramolecular fluorescent probe of the present application is a new type of fluorescent probe, which can selectively recognize norfloxacin in a water system.

[0025] 2. The preparation method of the fluorescent probe of the present application is simple and easy to implement.

[0026] 3. The fluorescent probe of the present application is convenient, sensitive, low-cost, selective and strong anti-interference in detecting and recognizing norfloxacin.

[0027] In order to verify the effect of the present application, the inventors have carried out the following experiments:

[0028] I. Qualitative analysis test

[0029] In a certain concentration range (10 -6 -10 -4 mol / L) of the fluorescent probe A in water, when the excitation wavelength is 349 nm, the maximum emission wavelength of the fluorescent probe A is 490 nm, when the fluorescent probe aqueous solution exists norfloxacin molecule mixture, the maximum emission wavelength of the fluorescent probe is red shifted from 490 nm to 558 nm, which shows yellow fluorescence. And the existence of other drugs, amino acids and pesticides will not affect the detection and recognition of probe A to norfloxacin.

[0030] II. Quantitative analysis test

[0031] 1. Accurately weigh 1.3 mg of guest G, and prepare 3 mL of a solution with a concentration of 1.0x10 -3 mol / L with water; accurately weigh 7.5 mg of octa-cucurbit, and prepare 50 mL of a solution with a concentration of 1.0x10 -4 mol / L with water; mix the guest G and the octa-cucurbit in a 100 mL volumetric flask according to a 1:1 molar ratio, and dilute to the calibration line with water to obtain the probe A (1.0x10 -5 mol / L).

[0032] 2. Weigh the high-purity norfloxacin to prepare 100 mL of a 1.0x10 -3 mol / L aqueous solution, and dilute it step by step as needed.

[0033] 3. Take five 10.0 mL volumetric flasks and add 1.0 mL of fluorescent probe A standard solution to each flask. Add 0, 0.2, 0.5, and 1.2 mL of norfloxacin mixture solution respectively to dilute to the mark, shake, and let stand at room temperature for 5 minutes.

[0034] 4. Fluorescence spectroscopy was introduced for measurement, with an excitation wavelength of 349 nm.

[0035] 5. Plot the concentration of norfloxacin on the x-axis and the fluorescence intensity on the y-axis to obtain the curve.

[0036] 6. Sample determination: Take a 10.0 mL volumetric flask, add 1.0 mL of probe A and norfloxacin mixture solution, dilute to the mark, let stand at room temperature for 5 minutes, introduce into a 3.0 cm quartz cuvette for fluorescence measurement, and find the sample concentration on the working curve according to the fluorescence intensity.

[0037] The lowest concentration that can be detected and identified is 1.08 × 10⁻⁷ mol·L⁻¹ -1 .

[0038] III. Anti-interference test

[0039] When the concentration of probe A is 1.00 × 10⁻⁶ -5 mol·L -1 In the reagent, the fluorescence red-shifted after the addition of norfloxacin. Further tests were conducted on the fluorescence changes after adding other drugs, amino acids, and pesticides to the A-norfloxacin solution. The results showed that the fluorescence intensity of norfloxacin detected by the fluorescent reagent A was not affected by the other drugs, amino acids, and pesticides mentioned above. Attached Figure Description

[0040] Appendix Figure 1 The chemical structural formula of the main molecule is an eight-membered cucurbit ring;

[0041] Appendix Figure 2 Here is the chemical structural formula of the supramolecular fluorescent probe of the present invention;

[0042] Appendix Figure 3 The chemical structural formula of the guest G;

[0043] Appendix Figure 4 This is the detection limit of fluorescent probe A for norfloxacin;

[0044] Appendix Figure 5 Fluorescent probe A (1.00 × 10⁻⁶) -5 mol·L -1 Fluorescence spectra and fluorescence photographs under ultraviolet light after exposure to other drugs, amino acids and pesticides;

[0045] Appendix Figure 6 To investigate the effect of coexisting drugs on the fluorescence detection of norfloxacin using reagent A. Detailed Implementation

[0046] The application will be further described in connection with the following examples, but not as a limitation to the application.

[0047] Embodiment of the application

[0048] Example 1

[0049] The preparation method of the supramolecular fluorescent probe for selective recognition of norfloxacin is as follows:

[0050] (1) Take the guest G shown in the attached Figure 3 , dissolve it with water, and prepare solution A with a concentration of 1.0x10 -3 mol·L -1 ;

[0051] (2) Take the eight-membered cucurbituril shown in the attached Figure 1 , dissolve it with water, and prepare solution B with a concentration of 1.0x10 -4 mol·L -1 ;

[0052] (3) Mix and dilute solution A and solution B to 1.0x10 - 5 mol·L -1 with a mixing molar ratio of eight-membered cucurbituril to guest G being 1:1, and shake well to obtain the supramolecular fluorescent probe for selective recognition of norfloxacin, the chemical structural formula of which is shown in the attached Figure 2 .

[0053] Example 2

[0054] The preparation method of the supramolecular fluorescent probe for selective recognition of norfloxacin is as follows:

[0055] (1) Take the guest G shown in the attached Figure 3 , dissolve it with water, and prepare solution A with a concentration of 0.5x10 -3 mol·L -1 ;

[0056] (2) Take the eight-membered cucurbituril shown in the attached Figure 1 , dissolve it with water, and prepare solution B with a concentration of 0.5x10 -4 mol·L -1 ;

[0057] (3) Mix and dilute solution A and solution B to 0.5x10 -5 mol·L -1 with a mixing molar ratio of eight-membered cucurbituril to guest G being 1:0.5, and shake well to obtain the supramolecular fluorescent probe for selective recognition of norfloxacin.

[0058] Example 3

[0059] The preparation method of the super-molecular fluorescent probe for selective recognition of norfloxacin is as follows:

[0060] (1) take the guest G shown in the formula Figure 3 Dissolve it in water to prepare solution A with a concentration of 1.5x10 -3 mol·L -1 ;

[0061] (2) take the eight-membered cucurbituril shown in the formula Figure 1 Dissolve it in water to prepare solution B with a concentration of 1.5x10 -4 mol·L -1 ;

[0062] (3) mix solution A and solution B with a mixing molar ratio of eight-membered cucurbituril to guest G of 1:1.5, dilute to 1.5x10 -5 mol·L -1 , shake well, and obtain the super-molecular fluorescent probe for selective recognition of norfloxacin.

[0063] Example 4

[0064] Application of the fluorescent probe of the present application for selective recognition of norfloxacin

[0065] The method is: drop the sample to be recognized into the super-molecular fluorescent probe described in Example 1 to obtain a sample solution, perform fluorescence excitation on the sample solution and test and analyze the fluorescence wavelength of the fluorescence excitation, wherein the excitation wavelength of the fluorescence excitation is 349 nm; when the sample to be recognized is added and norfloxacin is recognized, the maximum emission wavelength of the reagent is 558 nm.

[0066] The above is only a preferred specific embodiment of the present application, but the protection scope of the present application is not limited to this, any person skilled in the art can make equivalent replacement or change according to the technical scheme and the inventive concept of the present application within the technical range disclosed by the present application, which should be covered in the protection scope of the present application.

Claims

1. A supramolecular fluorescent probe for selectively recognizing norfloxacin, characterized in that, Its chemical structural formula is shown below: ； in It is an eight-yuan melon ring.

2. A method for preparing a supramolecular fluorescent probe for selectively recognizing norfloxacin according to claim 1, characterized in that: It is prepared from an octagonal cucurbit ring and a guest G; wherein the molecular formula of the guest G is C0. 29 H 24 N2O2 2+ The chemical structural formula is shown in the figure below: ； The method includes the following steps: (1) Weigh out object G, dissolve it in water, and prepare solution A; (2) Weigh out an octagonal cucurbit ring, dissolve it in water, and prepare solution B; (3) Mix and dilute solutions A and B, shake well to obtain a supramolecular fluorescent probe for selective recognition of norfloxacin; The concentration of solution A is 0.5 x 10⁻⁶. -3 mol·L -1 -1.5x10 -3 mol·L -1 ; The concentration of solution B is 0.5 x 10⁻⁶. -4 mol·L -1 -1.5x10 -4 mol·L -1 ; When solutions A and B are mixed, the molar ratio of the octagonal cucurbit ring to guest G is 1:0.5-1.

5. After mixing solutions A and B, the mixture is diluted to 0.5 x 10⁻⁶. -5 mol·L -1 -1.5x10 -5 mol·L -1 .

3. The application of the supramolecular fluorescent probe according to claim 1 in the selective recognition of norfloxacin.

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