CN112645941B - Oxazole derivative fluorescent probe and preparation method and application thereof - Google Patents
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- G01N21/64—Fluorescence; Phosphorescence
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Abstract
The invention belongs to metalThe field of ion detection, relates to copper ion detection, and particularly relates to an oxazole derivative fluorescent probe and a preparation method and application thereof. The structural formula is as follows:
. The oxazole derivative fluorescent probe prepared by the invention can be used for single selective trace detection of copper ions in aqueous solution at room temperature, has strong anti-interference capability on other metal ions, can be used for quantitatively detecting the copper ions, and has the detection limit of 3.94 multiplied by 10‑8 M。
Description
Technical Field
The invention belongs to the field of metal ion detection, relates to copper ion detection, and particularly relates to an oxazole derivative fluorescent probe as well as a preparation method and application thereof.
Background
Copper ions play a crucial role both in the biological and chemical fields. It is known that copper is the third trace element second to iron and zinc among the elements essential to human physiology; metallic copper is also widely used as a catalyst for a large number of industrial and biomedical intermediates; copper ions are in turn a catalyst for the biological enzymatic conversion reaction. However, the existence of a large amount of copper ions has a great disadvantage that the copper ions pollute the environment, and the biological systems in the water can influence the self-cleaning capability of the biological systems under the interference of the copper ions, thereby causing harm to the health of people. There are even some disease conditions, such as Wilson's disease, hypoglycemia, coronary heart disease, senile dementia, etc. Therefore, how to detect the copper ions rapidly, accurately and quantitatively with high selectivity is very important.
At present, the common methods for detecting copper ions mainly comprise atomic absorption spectrometry, high performance liquid chromatography, spectrophotometry, electrochemical sensing methods, inductively coupled plasma emission spectrometry and the like, and the methods have prominent advantages and disadvantages. Recently, the detection of fluorescence technology has received increasing attention from scientists because of its high selectivity, simplicity of operation, low cost and high sensitivity.
Disclosure of Invention
In order to improve the detection sensitivity of copper ions and reduce the detection cost, the invention provides an oxazole derivative fluorescent probe and a preparation method and application thereof.
The technical scheme of the invention is realized as follows:
an oxazole derivative fluorescent probe, which has a structural formula as follows:
the preparation method of the oxazole derivative fluorescent probe comprises the following steps:
(1) adding thionyl chloride into a solvent containing 2- (2-hydroxybenzene) oxazole-4-formic acid, heating to 45 ℃ or 80 ℃ under magnetic stirring, carrying out reflux reaction for 4-6 hours, cooling to room temperature, and removing unreacted thionyl chloride and the solvent to obtain acyl chloride of oxazole;
(2) dissolving the acyl chloride of the oxazole prepared in the step (1) into a solvent, adding a certain amount of 2-aminomethyl pyridine, heating to 45 ℃ for full reaction, cooling to room temperature, and concentrating, carrying out column chromatography and purifying to obtain the oxazole derivative fluorescent probe.
The molar ratio of the 2- (2-hydroxybenzene) oxazole-4-carboxylic acid to the thionyl chloride in the step (1) is 1: 3.
The solvent in the steps (1) and (2) is anhydrous benzene or anhydrous dichloromethane.
In the step (2), the molar ratio of the 2-aminomethyl pyridine to the acyl chloride of the oxazole is (1.1-1.5): 1.
the oxazole derivative fluorescent probe is applied to the preparation of a reagent for detecting copper ions.
The method comprises the following steps: preparing an oxazole derivative fluorescent probe solution with a certain concentration as a subject, and preparing a metal salt solution with a certain concentration as an object; and (4) performing fluorescence titration to test the complexing coordination condition of the host and the guest.
The solvent in the main body is at least one of DMSO, ethanol and acetonitrile, the anion in the object is at least one of nitrate and chlorate, and the solution used for fluorescence titration is HEPES buffer solution, Tris-HCl buffer solution or EtOH-H2And O is any one of the mixed solutions.
The concentrations of the host and the guest are both 1.0 × 10-5mmol / L。
The invention has the following beneficial effects:
1. the invention synthesizes the brand-new copper ion detection reagent for the first time, and the compound has the advantages of simple synthesis step, easy purification and the like, and passes through1H NMR、13C NMR and HRMS verification.
2. The detection reagent for oxazole copper ions prepared by the invention has the advantages of simple reaction conditions, simple structure, low raw material cost, simple and convenient purification operation, high purity of the prepared detection reagent and good solubility. The detection reagent is verified by infrared spectroscopy, nuclear magnetic resonance hydrogen spectroscopy, carbon spectroscopy and high-resolution mass spectrometry. The color of the detection reagent is obviously changed under an ultraviolet lamp of 365 nm before and after the detection of the copper ions. Meanwhile, the prepared oxazole detection reagent can realize detection imaging of copper ions in cells. The method can detect copper ions in aqueous solution in a single selective trace manner at room temperature, and has strong anti-interference capability on other metal ions.
3. The detection reagent for oxazole copper ions prepared by the invention can quantitatively detect copper ions, and the detection limit reaches 3.94 multiplied by 10-8 M。
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, it is obvious that the drawings in the following description are only some embodiments of the present invention, and for those skilled in the art, other drawings can be obtained according to the drawings without creative efforts.
FIG. 1 is an infrared spectrum of the detection reagent for oxazole type copper ions of the present invention.
Fig. 2 is a nuclear magnetic resonance hydrogen spectrum of the detection reagent for oxazole copper ions of the present invention.
Fig. 3 is a nuclear magnetic resonance carbon spectrum of the detection reagent for oxazole copper ions of the present invention.
Fig. 4 is a high-resolution mass spectrum of the detection reagent for oxazole copper ions of the present invention.
FIG. 5 is a high-resolution mass spectrum of a 1:1 complex formed by the detection reagent for oxazole-based copper ions and copper ions.
FIG. 6 is a fluorescence titration chart of the detection reagent for oxazole-based copper ions of the present invention after the reaction with copper ions.
FIG. 7 is a fluorescence diagram of the detection reagent for oxazole-based copper ions of the present invention after reacting with different metal ions.
FIG. 8 is a Job's plot of fluorescence of the detection reagent for oxazole-based copper ions of the present invention after the reaction with copper ions.
Detailed Description
The technical solutions of the present invention will be described clearly and completely below with reference to embodiments of the present invention, and it should be apparent 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.
Example 1
A preparation method of an oxazole derivative fluorescent probe comprises the following technical routes:
the method comprises the following steps:
(1) thionyl chloride (0.90 g, 7.50mmol) was added to anhydrous benzene (40 mL) containing 2- (2-hydroxyphenyl) oxazole-4-carboxylic acid (0.51 g, 2.50mmol), heated to 80 ℃ with magnetic stirring, and reacted for 4 hours under reflux. Cooling to room temperature, and removing unreacted thionyl chloride and solvent benzene to obtain acyl chloride of the oxazole;
(2) dissolving the oxazole acyl chloride (1.50 mmol) prepared in the step (1) into anhydrous dichloromethane, adding 2-aminomethyl pyridine (0.33 g, 3.00mmol), heating to 45 ℃, fully reacting for 4 hours, cooling to room temperature, concentrating a solvent, and purifying by column chromatography to obtain 0.42 g of oxazole derivative fluorescent probe.
The characterization result of the oxazole copper ion detection reagent prepared in this example is as follows:
1) infrared spectrum determination: at 4000--1The content of the active ingredients iS measured by an infrared spectrometer with the model of ThermoNICOLET-iS 5. As shown in FIG. 1, the main test absorption peaks of the detection reagent are 3403.06, 3093.28, 1662.87,1589.29, 750.75 and 676.86 cm-1。
2) Hydrogen nuclear magnetic resonance spectroscopy: the hydrogen spectrum is measured by a Bruker 400 nuclear magnetic resonance instrument by taking TMS as an internal standard and DMSO-d6 as a solvent, and the result is shown in figure 2, and the nuclear magnetic resonance hydrogen spectrum of the detection reagent is as follows: 10.39 (s, 1H), 9.48 (t,J = 16.0 Hz, 1H), 8.78 (s, 1H), 8.52 (d, J = 6.0 Hz, 1H), 7.85 (d, J = 10.4 Hz, 1H), 7.76 (t, J = 12.0Hz, 1H), 7.48 – 7.43 (m, 1H), 7.34 (d, J = 10.4 Hz, 1H), 7.27 (d, J = 9.2 Hz, 1H), 7.09 – 6.99 (m, 2H), 4.57 (d, J = 8.4 Hz, 2H)。
3) nuclear magnetic resonance carbon spectrum measurement: the carbon spectrum is measured by a Bruker 400 nuclear magnetic resonance instrument by taking TMS as an internal standard and DMSO-d6 as a solvent, and the result is shown in FIG. 3, and the nuclear magnetic resonance carbon spectrum of the detection reagent is as follows: 160.36, 160.05, 158.82, 156.64, 149.33, 141.88, 137.23, 136.31, 133.51, 127.27, 122.66, 121.57, 120.29, 117.82, 110.99, 44.37.
4) High-resolution mass spectrometry: the result of measurement by using a Thermo Fisher-exact Orbitrap LC/MS system is shown in FIG. 4, and the high resolution mass spectrum of the detection reagent is 296.1028 [ M + H [ ]]+The theoretical value is 296.1030.
Example 2
A preparation method of an oxazole derivative fluorescent probe comprises the following steps:
(1) thionyl chloride (0.90 g, 7.50mmol) was added to anhydrous dichloromethane (40 mL) containing 2- (2-hydroxyphenyl) oxazole-4-carboxylic acid (0.51 g, 2.50mmol), heated to 45 ℃ with magnetic stirring and reacted for 6 hours under reflux. Cooling to room temperature, and removing unreacted thionyl chloride and dichloromethane serving as a solvent to obtain acyl chloride of the oxazole;
(2) dissolving the oxazole acyl chloride (3.00 mmol) prepared in the step (1) into anhydrous dichloromethane, adding 2-aminomethyl pyridine (0.363 g, 3.30mmol), heating to 45 ℃, fully reacting for 6 hours, cooling to room temperature, concentrating a solvent, and purifying by column chromatography to obtain 0.36 g of the oxazole copper ion detection reagent.
Example 3
A preparation method of an oxazole derivative fluorescent probe comprises the following steps:
(1) thionyl chloride (0.90 g, 7.50mmol) was added to anhydrous benzene (40 mL) containing 2- (2-hydroxyphenyl) oxazole-4-carboxylic acid (0.51 g, 2.50mmol), heated to 80 ℃ with magnetic stirring, and reacted for 4 hours under reflux. Cooling to room temperature, and removing unreacted thionyl chloride and solvent benzene to obtain acyl chloride of the oxazole;
(2) dissolving the oxazole acyl chloride (2.75 mmol) prepared in the step (1) into anhydrous dichloromethane, adding 2-aminomethyl pyridine (0.30 g, 2.75mmol), heating to 45 ℃, fully reacting for 5 hours, cooling to room temperature, concentrating a solvent, and purifying by column chromatography to obtain 0.31 g of oxazole derivative fluorescent probe.
Example 4
A preparation method of an oxazole derivative fluorescent probe comprises the following steps:
(1) thionyl chloride (0.90 g, 7.50mmol) was added to anhydrous benzene (40 mL) containing 2- (2-hydroxyphenyl) oxazole-4-carboxylic acid (0.51 g, 2.50mmol), heated to 80 ℃ with magnetic stirring and reacted under reflux for 4 hours. Cooling to room temperature, and removing unreacted thionyl chloride and solvent benzene to obtain acyl chloride of the oxazole;
(2) dissolving the oxazole acyl chloride (3.125 mmol) prepared in the step (1) into anhydrous dichloromethane, adding 2-aminomethyl pyridine (0.41 g, 3.75mmol), heating to 45 ℃, fully reacting for 4 hours, cooling to room temperature, concentrating a solvent, and purifying by column chromatography to obtain 0.47 g of oxazole derivative fluorescent probe.
Application example
1. Sensitivity test: preparing an oxazole derivative fluorescent probe solution with a certain concentration as a host, and preparing a metal salt solution with a certain concentration as an object; and (3) carrying out fluorescence titration to test the complexing coordination condition of the host and the guest: wherein the metal ions are anhydrous nitrate or nitrate hydrate, and are dissolved with ultrapure water to obtain the metal ions with the concentration of 1.0 × 10-5mmol/L stock solution; the oxazole derivative fluorescent probe prepared in example 1 was dissolved in DMSO to prepare a concentration of 1.0X 10-5mmol/L stock solution; all fluorescence titration experiments were performed in HEPES buffer at pH 7.40.
Different concentrations of copper ions (0, 0.1X 10)-5 mmol / L, 0.2×10-5 mmol / L，0.3×10-5mmol / L，0.4×10-5 mmol / L，0.5×10-5 mmol / L，0.7×10-5 mmol / L，0.9×10-5 mmol / L，1.1×10-5 mmol / L，1.3×10-5 mmol / L，1.5×10-5mmol / L，1.7×10-5mmol / L，1.9×10-5mmol / L，2.1×10-mmol / L，2.3×10-5mmol / L，2.5×10-5mmol/L) was added to the probe solution, and the change in fluorescence intensity was detected, and FIG. 6 shows the fluorescent probe (concentration: 1.0X 10)-5mol/L) fluorescence spectra of different concentrations of copper ions under HEPES. In FIG. 6, the excitation wavelength is 392nm, and the concentration of copper ions is from 0 to 2.5X 10-5mol/L. By fluorescence emission spectroscopy analysis, the concentration of added copper ions is 0 to 2.5X 10-5In the mol/L range, the fluorescence intensity and the copper ion concentration have a good linear relation curve, and the quantitative detection of the copper ions is realized. The complexation constant reaches 3.80 multiplied by 10 according to the calculation of a B-H equation and a detection limit equation4M, detection limit of 3.94X 10-8 M-1(ii) a High resolution mass spectrometry as shown in FIG. 5 and Job’The s-curve is shown in FIG. 8, demonstrating that the detection reagent forms a 1:1 complex with copper ions.
2. And (3) specific experiments: adding phase to fluorescent probe detection solutionSame concentration (2.5X 10)-5mmol/L) of Na+、K+、Ag+、Zn2+、Cd2+、Ca2+、Mg2+、Mn2+、Pb2+、Ba2+、Hg2+、Co2+、Fe2+、Al3+、Fe3+、Cr3+ When metal ions are used, the fluorescence intensity is not obviously changed; whereas the fluorescence intensity after addition of copper ions showed almost quenching, the probe color disappeared under 365 nm UV illumination, and the maximum emission wavelength blue shifted to 425 nm. The results are shown in FIG. 7, and it can be seen from FIG. 7 that: the fluorescent probe has the maximum emission wavelength of 456 nm under the excitation of the wavelength of 314 nm, and emits bluish violet light under the irradiation of an ultraviolet lamp of 365 nm. The fluorescent probe of the application realizes the specific detection of copper ions with high selectivity.
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 (8)
1. The preparation method of the oxazole derivative fluorescent probe is characterized in that the structural formula of the oxazole derivative fluorescent probe is as follows:
the preparation steps are as follows:
(1) adding thionyl chloride into a solvent containing 2- (2-hydroxybenzene) oxazole-4-formic acid, heating to 80 ℃ under magnetic stirring, carrying out reflux reaction for 4-6 hours, cooling to room temperature, and removing unreacted thionyl chloride and the solvent to obtain acyl chloride of oxazole;
(2) dissolving the acyl chloride of the oxazole prepared in the step (1) into a solvent, adding a certain amount of 2-aminomethyl pyridine, heating to 45 ℃ for full reaction, cooling to room temperature, and concentrating, carrying out column chromatography and purifying to obtain the oxazole derivative fluorescent probe.
2. The method of claim 1, wherein: the molar ratio of the 2- (2-hydroxybenzene) oxazole-4-carboxylic acid to the thionyl chloride in the step (1) is 1: 3.
3. The method of claim 1, wherein: the solvent in the steps (1) and (2) is anhydrous benzene or anhydrous dichloromethane.
4. The method of claim 1, wherein: in the step (2), the molar ratio of the 2-aminomethyl pyridine to the acyl chloride of the oxazole is (1.1-1.5): 1.
5. use of an oxazole derivative fluorescent probe prepared by the method of any one of claims 1 to 4 in the preparation of a reagent for detecting copper ions.
6. Use according to claim 5, characterized by the steps of: preparing an oxazole derivative fluorescent probe solution with a certain concentration as a host, and preparing a metal salt solution with a certain concentration as an object; and (4) performing fluorescence titration to test the complexing coordination condition of the host and the guest.
7. Use according to claim 6, characterized in that: the solvent in the main body is at least one of DMSO, ethanol and acetonitrile, the anion in the object is at least one of nitrate and chlorate, and the solution used for fluorescence titration is HEPES buffer solution, Tris-HCl buffer solution or EtOH-H2And O is any one of the mixed solutions.
8. Use according to claim 7, characterized in that: the concentrations of the host and the guest are both 1.0 × 10- 5mmol / L。
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