CN111504964A - MOF-Cd probe for detecting lysine and preparation method and application thereof - Google Patents
MOF-Cd probe for detecting lysine and preparation method and application thereof Download PDFInfo
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Abstract
The invention provides a MOF-Cd probe for detecting lysine, a preparation method and application thereof, wherein the MOF-Cd probe takes tetra (4-imidazolyl phenyl) ethylene as a ligand and utilizes Cd (NO)3)•4H2The MOF-Cd probe can detect analytes in water in a fluorescence-enhanced response mode, has the advantages of high selectivity, high sensitivity and high stability, can detect the content of lysine (L ys) in water under the interference of other seven kinds of essential amino acids of human bodies, has the detection limit of 200 nM, and has no influence on the detection effect by other amino acids.
Description
Technical Field
The invention relates to the technical field of amino acid detection, in particular to a MOF-Cd probe for detecting lysine and a preparation method and application thereof.
Background
Amino acids are indispensable components in organisms, and the growth and development processes of the organisms cannot be separated from the amino acids. In the aspect of detecting certain diseases, the content of the amino acid can be directly detected. For example, histidine (His), in addition to being an essential amino acid for human growth, is a regulator of neurotransmitter and metal transmission in mammals. Asthma and late cirrhosis can lead to abnormal levels of histidine-rich proteins; aspartic acid (Asp) is an endogenous amino acid for human growth, and a certain amount of aspartic acid in cells is essential for the cell proliferation process and respiration. Thus, detection of abnormal levels of aspartate can be used as an early diagnosis of tumors.
In recent years, researchers began to research and use MOFs as fluorescent probes to specifically detect amino acids, L ee research team reported that a fluorescent metal organic framework (L MOF) based on copper iodide (I) clusters, L MOF dispersed in water has selectivity to Cys higher than that of other amino acids, and K is calculatedSVHas a value of 6.128 × 102M-1(R =0.9914)（ji Lee, Huiyeong Ju, Jong Hwa Jung, Mari Ikeda, Yoichi Habata, andShim Sung Lee， Conventional and mechanochemical syntheses of copper(I) iodideluminescent MOF with bis(amidoquinoline) and Its application for thedetection of amino acid in aqueous solution [J]Inorg. chem., 2019, 58, 1177-. Although excellent in selectivity, the recognition process is based on fluorescence quenching, and the appearance of a bright signal in a completely dark environment is more easily detected than the decrease in a completely bright signal, so that it is important to develop a fluorescent probe for detecting an amino acid based on fluorescence enhancement.
Disclosure of Invention
The invention aims to provide a MOF-Cd probe for detecting lysine, a preparation method and application thereof, and provides a detection method which can identify L ys in water through fluorescence enhancement and has low detection limit and high selectivity.
The technical scheme adopted by the invention is as follows: a MOF-Cd probe for detecting lysine is characterized in that the MOF-Cd probe takes tetra (4-imidazolyl phenyl) ethylene as a ligand and utilizes Cd (NO)3)•4H2O is used asThe preparation process of the MOF-Cd probe comprises the following steps:
(a) respectively weighing tetra (4-iodophenyl) ethylene, imidazole, anhydrous potassium carbonate and anhydrous copper sulfate as raw materials, mixing the raw materials, adding the mixed raw materials into a high-pressure resistant reaction tube, and carrying out solvent-free reaction for 11-13 h in 180-fold sand bath at 190 ℃ under the protection of nitrogen, wherein the molar ratio of the raw materials is as follows: tetra (4-iodophenyl) ethylene, imidazole, anhydrous potassium carbonate, anhydrous copper sulphate = 2: 38-42: 10-12: 0.07-0.09;
(b) cooling to room temperature after reaction, washing the obtained solid with distilled water, drying, dissolving with dichloromethane, separating by column chromatography to obtain a pure product, and vacuum drying the pure product at 45-55 ℃ overnight to obtain a white ligand TIPE;
(c) weighing the ligands TIPE and Cd (NO)3)•4H2O in a glass bottle, wherein ligands TIPE and Cd (NO)3)•4H2Adding DMF, water and ammonia water with the mass concentration of 25% into a glass bottle, uniformly mixing, wherein a ligand TIPE, DMF, water and ammonia water =3 mg: 2-4 m L: 0.5-2m L: 0.5-2m L, then putting into an oven, carrying out temperature programming for 10-14 h to 75-85 ℃, carrying out constant temperature incubation for 45-52 h, and carrying out temperature programming for 65-78 h to 20-30 ℃ to obtain a light yellow cuboid crystal, namely an MOF-probe Cd.
In the step (a), the anhydrous potassium carbonate is ground into powder.
In the step (b), the stationary phase of column chromatography is silica gel GF254, the mobile phase is dichloromethane/methanol mixed solution with the volume ratio of 10: 1, and the eluent is decompressed and evaporated to remove the solvent to obtain the pure product.
A preparation method of an MOF-Cd probe for detecting lysine comprises the following steps:
(a) respectively weighing tetra (4-iodophenyl) ethylene, imidazole, anhydrous potassium carbonate and anhydrous copper sulfate as raw materials, mixing the raw materials, adding the mixed raw materials into a high-pressure resistant reaction tube, and carrying out solvent-free reaction for 11-13 h in 180-fold sand bath at 190 ℃ under the protection of nitrogen, wherein the molar ratio of the raw materials is as follows: tetra (4-iodophenyl) ethylene, imidazole, anhydrous potassium carbonate, anhydrous copper sulphate = 2: 38-42: 10-12: 0.07-0.09;
(b) cooling to room temperature after reaction, washing the obtained solid with distilled water, drying, dissolving with dichloromethane, separating by column chromatography to obtain a pure product, and vacuum drying the pure product at 45-55 ℃ overnight to obtain a white ligand TIPE;
(c) weighing the ligands TIPE and Cd (NO)3)•4H2O in a glass bottle, wherein ligands TIPE and Cd (NO)3)•4H2Adding DMF, water and ammonia water with the mass concentration of 25% into a glass bottle, uniformly mixing, wherein a ligand TIPE, DMF, water and ammonia water =3 mg: 2-4 m L: 0.5-2m L: 0.5-2m L, then putting into an oven, carrying out temperature programming for 10-14 h to 75-85 ℃, carrying out constant temperature incubation for 45-52 h, and carrying out temperature programming for 65-78 h to 20-30 ℃ to obtain a light yellow cuboid crystal, namely an MOF-probe Cd.
In the step (a), the anhydrous potassium carbonate is ground into powder.
In the step (b), the stationary phase of column chromatography is silica gel GF254, the mobile phase is dichloromethane/methanol mixed solution with the volume ratio of 10: 1, and the eluent is decompressed and evaporated to remove the solvent to obtain the pure product.
The MOF-Cd probe is applied to lysine detection in water.
The fluorescence intensity of the MOF-Cd probe in water is enhanced along with the increase of the lysine concentration in the concentration range of 0-5.66 mu M, and the detection limit of the MOF-Cd probe for recognizing lysine is 200 nM.
The invention can detect the analyte in water by a fluorescence enhanced response mode, has the advantages of high selectivity, high sensitivity and high stability, can detect the content of lysine (L ys) in water under the interference of other seven essential amino acids of human body, has the detection limit of 200 nM, and has no influence on the detection effect by other amino acids.
Drawings
FIG. 1: (a) schematic diagram of asymmetric structural units of MOF-Cd; (b) crystal stacking diagram along the y-axis.
FIG. 2: PXRD pattern of MOF-Cd.
FIG. 3 is a graph showing the results of selective recognition of L ys by MOF-Cd among eight essential amino acids for human body.
FIG. 4 is a fluorescence titration chart of L ys.
FIG. 5 Standard graph of MOF-Cd fluorescence change with L ys concentration.
FIG. 6 is a graph showing the change in fluorescence of MOF-Cd versus L ys in the presence of seven other essential amino acids (box: not added L ys; column: added L ys).
Detailed Description
The present invention is described in detail below with reference to specific examples, wherein reagents and procedures not mentioned in the examples are all performed according to the routine procedures in the art.
EXAMPLE 1 preparation of MOF-Cd probes
First, the ligand TIPE was synthesized: the compound tetrakis (4-iodophenyl) ethylene (1.67 g, 2.00 mmol), imidazole (2.70g, 40.00 mmol), anhydrous potassium carbonate (1.52 g, 11.00 mmol) ground to powder, anhydrous copper sulfate (0.02 g, 0.08 mmol) were added to a pressure resistant reaction tube and reacted in a sand bath at 185 ℃ for 12 h under nitrogen protection. And then cooling to room temperature, washing the obtained solid with distilled water for three times, drying, dissolving with dichloromethane, eluting and separating by using a column chromatography technology (a stationary phase is silica gel GF254, and a mobile phase is dichloromethane/methanol 10: 1), evaporating under reduced pressure to remove a solvent to obtain a pure product, and drying the pure product in vacuum at 50 ℃ overnight to obtain the white ligand TIPE.
Weighing the ligands TIPE (3 mg, 0.005 mmol) and Cd (NO)3)·4H2O (30 mg, 0.097 mmol) is filled into a small transparent glass bottle with the thickness of 10 m L, then 2m L DMF, 0.5 m L water and 0.5 m L25% ammonia water are added, the glass bottle is placed into an oven, the temperature is programmed to be 12 h to 80 ℃, the temperature is kept at constant temperature for 48 h, the temperature is programmed to be 72 h to 25 ℃, light yellow cuboid crystals, namely MOF-Cd probes, are obtained, the obtained MOF-Cd probes are analyzed, as shown in figures 1 and 2, figure 1 is the structure of the obtained MOF-Cd, and figure 2 is the PXRD diagram of the MOF-Cd.
Example 2 detection of L ys by MOF-Cd as fluorescent Probe
In this example, L ys was selectively detected by the synthesized MOF-Cd solution using eight amino acids essential to human body, i.e., valine (Val), isoleucine (Ile), threonine (Thr), lysine (L ys), methionine (Met), tryptophan (Trp), phenylalanine (Phe) and leucine (L eu).
Weighing 20 mg of ground MOF-Cd crystal powder, adding into 100M L distilled water, carrying out ultrasonic treatment for 1 h, standing overnight to obtain suspension with MOF-Cd concentration of 0.2 mg/M L, and preparing each amino acid stock solution with concentration of 10-4M.
Taking a MOF-Cd solution of 1.8 m L by using a pipette, then respectively adding amino acid aqueous solutions which are necessary for human bodies, namely valine (Val), isoleucine (Ile), threonine (Thr), lysine (L ys), methionine (Met), tryptophan (Trp), phenylalanine (Phe) and leucine (L eu), wherein the addition amount of the eight necessary amino acids is 200 mu L, respectively detecting the fluorescence intensity, carrying out a plurality of parallel tests on each amino acid, and finally, the result is shown in figure 3, wherein L ys in figure 3 obviously enhances the fluorescence of the MOF-Cd solution.
In the MOF-Cd solution, the concentration of the analyte in the MOF-Cd solution gradually increased with the addition of L ys, and the fluorescence gradually increased as shown in FIG. 4, when the fluorescence intensity at L ys with the addition of 120 u L (5.56 um) and the fluorescence intensity at L ys with the addition of 100 u L (4.74um) were substantially the same, the fluorescence did not increase any further as shown in FIG. 5, where I is plotted over a final concentration range of 0-5.66. mu.M0A graph of the relationship between I and L ys concentration, the regression linear equation is y = 162176.273 x-25337.835, the two are found to have good linear relationship, and the detection limit of MOF-Cd recognition L ys is calculated to be 200 nM according to the detection limit formula (3 sigma/k).
In the MOF-Cd solution of 1.6 m L, 200 mu L of other seven essential amino acids (valine (Val), isoleucine (Ile), threonine (Thr), methionine (Met), tryptophan (Trp), phenylalanine (Phe) and leucine (L eu)) are added, and 200 mu L of lysine (L ys) is added, so that other amino acids exist in the presence of L ys, and the fluorescence of the MOF-Cd solution is still enhanced after L ys is added under the condition that other seven essential amino acids exist in the human body, which indicates that the other seven essential amino acids do not interfere with the detection of L ys.
It will be appreciated that modifications and variations may be resorted to those skilled in the art, and that all such modifications and variations are intended to be included within the scope of the invention as defined by the appended claims.
Claims (8)
1. A MOF-Cd probe for detecting lysine is characterized in that the MOF-Cd probe takes tetra (4-imidazolyl phenyl) ethylene as a ligand and utilizes Cd (NO)3)•4H2The preparation process of the MOF-Cd probe comprises the following steps:
(a) respectively weighing tetra (4-iodophenyl) ethylene, imidazole, anhydrous potassium carbonate and anhydrous copper sulfate as raw materials, mixing the raw materials, adding the mixed raw materials into a high-pressure resistant reaction tube, and carrying out solvent-free reaction for 11-13 h in 180-fold sand bath at 190 ℃ under the protection of nitrogen, wherein the molar ratio of the raw materials is as follows: tetra (4-iodophenyl) ethylene, imidazole, anhydrous potassium carbonate, anhydrous copper sulphate = 2: 38-42: 10-12: 0.07-0.09;
(b) cooling to room temperature after reaction, washing the obtained solid with distilled water, drying, dissolving with dichloromethane, separating by column chromatography to obtain a pure product, and vacuum drying the pure product at 45-55 ℃ overnight to obtain a white ligand TIPE;
(c) weighing the ligands TIPE and Cd (NO)3)•4H2O in a glass bottle, wherein ligands TIPE and Cd (NO)3)•4H2Adding DMF, water and ammonia water with the mass concentration of 25% into a glass bottle, uniformly mixing, wherein a ligand TIPE, DMF, water and ammonia water =3 mg: 2-4 m L: 0.5-2m L: 0.5-2m L, then putting into an oven, carrying out temperature programming for 10-14 h to 75-85 ℃, carrying out constant temperature incubation for 45-52 h, and carrying out temperature programming for 65-78 h to 20-30 ℃ to obtain a light yellow cuboid crystal, namely an MOF-probe Cd.
2. The MOF-Cd probe for detecting lysine according to claim 1, wherein in step (a), the anhydrous potassium carbonate is ground into powder.
3. The MOF-Cd probe for detecting lysine according to claim 1, wherein in the step (b), a stationary phase of column chromatography is silica gel GF254, a mobile phase is a dichloromethane/methanol mixed solution with a volume ratio of 10: 1, and an eluent is subjected to reduced pressure evaporation to remove a solvent to obtain a pure product.
4. A preparation method of an MOF-Cd probe for detecting lysine is characterized by comprising the following steps:
(a) respectively weighing tetra (4-iodophenyl) ethylene, imidazole, anhydrous potassium carbonate and anhydrous copper sulfate as raw materials, mixing the raw materials, adding the mixed raw materials into a high-pressure resistant reaction tube, and carrying out solvent-free reaction for 11-13 h in 180-fold sand bath at 190 ℃ under the protection of nitrogen, wherein the molar ratio of the raw materials is as follows: tetra (4-iodophenyl) ethylene, imidazole, anhydrous potassium carbonate, anhydrous copper sulphate = 2: 38-42: 10-12: 0.07-0.09;
(b) cooling to room temperature after reaction, washing the obtained solid with distilled water, drying, dissolving with dichloromethane, separating by column chromatography to obtain a pure product, and vacuum drying the pure product at 45-55 ℃ overnight to obtain a white ligand TIPE;
(c) weighing the ligands TIPE and Cd (NO)3)•4H2O in a glass bottle, wherein ligands TIPE and Cd (NO)3)•4H2Adding DMF, water and ammonia water with the mass concentration of 25% into a glass bottle, uniformly mixing, wherein a ligand TIPE, DMF, water and ammonia water =3 mg: 2-4 m L: 0.5-2m L: 0.5-2m L, then putting into an oven, carrying out temperature programming for 10-14 h to 75-85 ℃, carrying out constant temperature incubation for 45-52 h, and carrying out temperature programming for 65-78 h to 20-30 ℃ to obtain a light yellow cuboid crystal, namely an MOF-probe Cd.
5. The method for preparing the MOF-Cd probe for detecting lysine according to claim 4, wherein in the step (a), the anhydrous potassium carbonate is ground into powder.
6. The preparation method of the MOF-Cd probe for detecting lysine according to claim 4, wherein in the step (b), a stationary phase of column chromatography is silica gel GF254, a mobile phase is dichloromethane/methanol mixed solution with a volume ratio of 10: 1, and an eluent is subjected to reduced pressure evaporation to remove a solvent to obtain a pure product.
7. Use of the MOF-Cd probe of any one of claims 1 to 3 for detecting lysine in water.
8. The use of claim 7, wherein the MOF-Cd probe has a fluorescence intensity in water in the range of 0-5.66 μ M that increases with increasing lysine concentration, and the MOF-Cd probe has a detection limit for lysine recognition of 200 nM.
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