CN111504964B - MOF-Cd probe for detecting lysine as well as preparation method and application thereof - Google Patents
MOF-Cd probe for detecting lysine as well as preparation method and application thereof Download PDFInfo
- Publication number
- CN111504964B CN111504964B CN202010327126.5A CN202010327126A CN111504964B CN 111504964 B CN111504964 B CN 111504964B CN 202010327126 A CN202010327126 A CN 202010327126A CN 111504964 B CN111504964 B CN 111504964B
- Authority
- CN
- China
- Prior art keywords
- mof
- probe
- water
- tipe
- lysine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Images
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- 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"
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
- C08G83/008—Supramolecular polymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1408—Carbocyclic compounds
- C09K2211/1425—Non-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1441—Heterocyclic
- C09K2211/1466—Heterocyclic containing nitrogen as the only heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/188—Metal complexes of other metals not provided for in one of the previous groups
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Immunology (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Medicinal Chemistry (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
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 )•4H 2 The MOF-Cd probe can detect analytes in water, detects the analytes in a fluorescence enhanced response mode, and has the advantages of high selectivity, high sensitivity and high stability. The invention can detect the content of lysine (Lys) in water under the interference of other seven kinds of amino acid necessary for human body, the detection limit is 200 nM, and the detection effect is not influenced by other amino acid.
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.
Conventional methods for detecting amino acids include: the methods of spectral analysis, high performance liquid chromatography, electrochemistry and the like have the defects of high cost, long time, complex test and the like. In recent years, researchers have begun investigating the specific detection of amino acids using MOFs as fluorescent probes. Lee scientific research group reports that a fluorescent metal organic framework (LMOF) based on copper iodide (I) clusters, the selectivity of the LMOF dispersed in water to Cys exceeds that of other amino acids, and K is calculated SV Has a value of 6.128 × 10 2 M -1 (R = 0.9914)（ji Lee, Huiyeong Ju, Jong Hwa Jung, Mari Ikeda, Yoichi Habata, and Shim Sung Lee， Conventional and mechanochemical syntheses of copper(I) iodide luminescent MOF with bis(amidoquinoline) and Its application for the detection of amino acid in aqueous solution [J]Inorg. Chem., 2019, 58, 1177-1183). 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 Lys through fluorescence enhancement in water 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 )•4H 2 The 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 mixture into a high-pressure resistant reaction tube, and carrying out a sand bath solvent-free reaction at 180-190 ℃ under the protection of nitrogen to obtain 11-13 h, wherein the molar ratio of the raw materials is as follows: tetra (4-iodophenyl) ethylene, imidazole, anhydrous potassium carbonate, anhydrous copper sulfate = 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 )•4H 2 O in a glass bottle, wherein the ligands TIPE and Cd (NO) 3 )•4H 2 Adding 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 mL: 0.5-2 mL: 0.5-2mL, then placing into an oven, programming the temperature to 10-14 h to 75-85 ℃, incubating at constant temperature to 45-52 h, programming the temperature to 65-78 h to 20-30 ℃, and obtaining a light yellow cuboid crystal, namely the MOF-Cd probe.
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 a 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 mixture into a high-pressure resistant reaction tube, and carrying out a sand bath solvent-free reaction at 180-190 ℃ under the protection of nitrogen to obtain 11-13 h, 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 )•4H 2 O in a glass bottle, wherein ligands TIPE and Cd (NO) 3 )•4H 2 Adding 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 are =3 mg: 2-4 mL: 0.5-2 mL: 0.5-2mL, then placing into an oven, programming the temperature to 10-14 h-75-85 ℃, incubating at the constant temperature to 45-52 h, programming the temperature to 65-78 h-20-30 ℃, and obtaining a light yellow cuboid crystal, namely the MOF-Cd probe.
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 increased along with the increase of the lysine concentration within 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, detects the analyte in a fluorescence enhanced response mode, and has the advantages of high selectivity, high sensitivity and high stability. The invention can detect the content of lysine (Lys) in water under the interference of other seven kinds of essential amino acid, the detection limit is 200 nM, and the detection effect is not influenced by other amino acid.
Drawings
FIG. 1: (a) a schematic of an asymmetric building block of MOF-Cd; (b) crystal stacking diagram along the y-axis.
FIG. 2: PXRD pattern of MOF-Cd.
FIG. 3: among the eight essential amino acids for human body, the result of selective recognition of Lys by MOF-Cd is shown.
FIG. 4: fluorescence titration of Lys.
FIG. 5: standard plot of MOF-Cd fluorescence change with Lys concentration.
FIG. 6: fluorescence profiles of MOF-Cd versus Lys in the presence of seven other essential amino acids for the human body (box: no Lys added; cylinder: lys added).
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 (2.70 g,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 ℃ under nitrogen protection with no solvent 12 h. And then cooling to room temperature, washing the obtained solid with distilled water for three times, drying, dissolving with dichloromethane, leaching and separating by using a column chromatography technology (a fixed 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 a white ligand TIPE.
The ligands TIPE (3 mg,0.005 mmol) and Cd (NO) were weighed 3 )·4H 2 O (30 mg,0.097 mmol), was charged into a 10 mL clear glass vial, after which 2mL DMF,0.5 mL water and 0.5 mL 25% ammonia were added. Putting the glass bottle into an oven, carrying out programmed temperature rise of 12 h-80 ℃, carrying out constant temperature incubation of 48 h, and carrying out programmed temperature reduction of 72 h-25 ℃ to obtain a light yellow cuboid crystal, namely an MOF-Cd probe, and analyzing the obtained MOF-Cd probe, wherein as shown in figures 1 and 2, figure 1 is a structure of the obtained MOF-Cd, and figure 2 is a PXRD diagram of the MOF-Cd.
Example 2: detection of Lys by MOF-Cd as a fluorescent Probe
In this example, lys was selectively detected by using synthesized MOF-Cd solution using eight amino acids essential to human body, i.e., valine (Val), isoleucine (Ile), threonine (Thr), lysine (Lys), methionine (Met), tryptophan (Trp), phenylalanine (Phe), and leucine (Leu).
Weighing the ground MOF-Cd crystal powder 20 mg, adding the powder into 100 mL distilled water, carrying out ultrasonic treatment on 1 h, standing overnight to obtain suspension with the MOF-Cd concentration of 0.2 mg/mL, and preparing amino acid stock solutions with the concentrations of 10-4M.
Taking the MOF-Cd solution of 1.8 mL by using a liquid moving machine, then respectively adding amino acid aqueous solutions which are necessary for human bodies, namely valine (Val), isoleucine (Ile), threonine (Thr), lysine (Lys), methionine (Met), tryptophan (Trp), phenylalanine (Phe) and leucine (Leu), wherein the adding amount of the eight necessary amino acids is 200 mu L, respectively detecting fluorescence intensity, performing a plurality of parallel tests on each amino acid, and finally, the final result is shown in figure 3, wherein Lys in figure 3 obviously enhances the fluorescence of the MOF Cd-Cd solution.
In the MOF-Cd solution, with the addition of Lys, the concentration of the analyte in the MOF-Cd solution gradually increases and the fluorescence gradually increases. As shown in FIG. 4, when the fluorescence intensity of Lys added with 120 uL (5.56 um) and the fluorescence intensity of Lys added with 100 uL (4.74 um) were substantially the same, the fluorescence did not increase any more. As shown in FIG. 5, I is plotted over the final concentration range of 0-5.66. Mu.M 0 -graph of the relationship between I and Lys concentration, regression linear equation: y = 162176.273 x-25337.835, the two are found to have good linear relation, and the detection limit for MOF-Cd to identify Lys is calculated to be 200 nM according to the detection limit formula (3 sigma/k).
To the 1.6 mL MOF-Cd solution, 200. Mu.L of each of the other seven essential amino acids (valine (Val), isoleucine (Ile), threonine (Thr), methionine (Met), tryptophan (Trp), phenylalanine (Phe) and leucine (Leu)) was added, and 200. Mu.L of lysine (Lys) was added, so that other amino acids were also present in the presence of Lys. FIG. 6 shows that the fluorescence of the MOF-Cd solution is still enhanced after addition of Lys in the presence of seven other essential amino acids, indicating that the seven other essential amino acids do not interfere with the detection of Lys.
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 uses tetra (4-imidazolyl phenyl) ethylene as a ligand and Cd (NO) 3 )•4H 2 The 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 mixture into a high-pressure resistant reaction tube, and carrying out a sand bath solvent-free reaction at 180-190 ℃ under the protection of nitrogen for 11-13 h, 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, dissolving the solid with dichloromethane after drying, separating by utilizing a column chromatography technology to obtain a pure product, and drying the pure product in vacuum at the temperature of 45-55 ℃ overnight to obtain a white ligand TIPE;
(c) Weighing the ligands TIPE and Cd (NO) 3 )•4H 2 O in a glass bottle, wherein the ligands TIPE and Cd (NO) 3 )•4H 2 Adding 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 mL: 0.5-2 mL: 0.5-2mL, then placing into an oven, programming the temperature to 10-14 h to 75-85 ℃, incubating at constant temperature to 45-52 h, programming the temperature to 65-78 h to 20-30 ℃, and obtaining a light yellow cuboid crystal, namely the MOF-Cd probe.
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 mixture into a high-pressure resistant reaction tube, and carrying out a sand bath solvent-free reaction at 180-190 ℃ under the protection of nitrogen to obtain 11-13 h, 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 )•4H 2 O in a glass bottle, wherein the ligands TIPE and Cd (NO) 3 )•4H 2 Adding 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 mL: 0.5-2 mL: 0.5-2mL, then placing into an oven, programming the temperature to 10-14 h to 75-85 ℃, incubating at constant temperature to 45-52 h, programming the temperature to 65-78 h to 20-30 ℃, and obtaining a light yellow cuboid crystal, namely the MOF-Cd probe.
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 recognizes lysine with a detection limit of 200 nM.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010327126.5A CN111504964B (en) | 2020-04-23 | 2020-04-23 | MOF-Cd probe for detecting lysine as well as preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010327126.5A CN111504964B (en) | 2020-04-23 | 2020-04-23 | MOF-Cd probe for detecting lysine as well as preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN111504964A CN111504964A (en) | 2020-08-07 |
| CN111504964B true CN111504964B (en) | 2022-11-18 |
Family
ID=71871220
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202010327126.5A Active CN111504964B (en) | 2020-04-23 | 2020-04-23 | MOF-Cd probe for detecting lysine as well as preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN111504964B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112812768B (en) * | 2021-01-22 | 2022-05-20 | 江西农业大学 | Functional Eu3+Preparation of @ UiO-66-FDC fluorescent probe and application thereof in detection of tryptophan |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1883417A2 (en) * | 2005-05-25 | 2008-02-06 | Curedm Inc. | Peptides, derivatives and analogs thereof, and methods of using same |
| WO2013051035A2 (en) * | 2011-10-03 | 2013-04-11 | Council Of Scientific And Industrial Research | Water soluble metal-organic frameworks (mofs) |
| WO2016000032A1 (en) * | 2014-07-03 | 2016-01-07 | Commonwealth Scientific And Industrial Research Organisation | Host-guest metal organic framework systems |
| CN106018360A (en) * | 2016-05-13 | 2016-10-12 | 深圳职业技术学院 | Method for detecting urea based on metal organic framework material fluorescent sensor |
| CN109206627A (en) * | 2017-06-30 | 2019-01-15 | 翁秋梅 | A kind of hybrid cross-linked dynamic aggregation object |
| CN109232589A (en) * | 2018-10-19 | 2019-01-18 | 贵州大学 | A kind of fluorescence probe and its preparation and application |
| CN109932345A (en) * | 2019-02-01 | 2019-06-25 | 中南民族大学 | A kind of lysine detection method based on quantum dot and nanogold |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100203647A1 (en) * | 2008-11-21 | 2010-08-12 | The Rockefeller University | Chemical Reporters of Protein Acylation |
| US9624216B2 (en) * | 2015-04-21 | 2017-04-18 | Forma Therapeutics, Inc. | Quinolinone five-membered heterocyclic compounds as mutant-isocitrate dehydrogenase inhibitors |
| US10793683B2 (en) * | 2016-07-27 | 2020-10-06 | Massachusetts Institute Of Technology | Block co-poly(metal organic nanostructures) (BCPMONs) and uses thereof |
-
2020
- 2020-04-23 CN CN202010327126.5A patent/CN111504964B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1883417A2 (en) * | 2005-05-25 | 2008-02-06 | Curedm Inc. | Peptides, derivatives and analogs thereof, and methods of using same |
| WO2013051035A2 (en) * | 2011-10-03 | 2013-04-11 | Council Of Scientific And Industrial Research | Water soluble metal-organic frameworks (mofs) |
| WO2016000032A1 (en) * | 2014-07-03 | 2016-01-07 | Commonwealth Scientific And Industrial Research Organisation | Host-guest metal organic framework systems |
| CN106018360A (en) * | 2016-05-13 | 2016-10-12 | 深圳职业技术学院 | Method for detecting urea based on metal organic framework material fluorescent sensor |
| CN109206627A (en) * | 2017-06-30 | 2019-01-15 | 翁秋梅 | A kind of hybrid cross-linked dynamic aggregation object |
| CN109232589A (en) * | 2018-10-19 | 2019-01-18 | 贵州大学 | A kind of fluorescence probe and its preparation and application |
| CN109932345A (en) * | 2019-02-01 | 2019-06-25 | 中南民族大学 | A kind of lysine detection method based on quantum dot and nanogold |
Non-Patent Citations (3)
| Title |
|---|
| A stable 3D Cd(II) metal–organic framework for;Jian-Long Du;《RSC Advances》;20171019;全文 * |
| Stable Cd(II)-MOF as a fluorescent sensor for efficient detection of uranyl;Jie Liu;《Materials Letters》;20190122;全文 * |
| Yanhong Liu.Post-imparting Brønsted acidity into an aminofunctionalized.《RSC Dalton Trans 》.2019, * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN111504964A (en) | 2020-08-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN109735328B (en) | Fluorescent probe for detecting intracellular hydrogen sulfide and preparation method and application thereof | |
| CN108863922B (en) | AIE-based polymer ratio fluorescence sensor capable of rapidly detecting hypochlorous acid and preparation method and application thereof | |
| CN104560027B (en) | A kind of fluorescent probe distinguishing detection biological thiol and preparation method thereof | |
| CN107721922B (en) | Quinoline biological thiol fluorescent probe and preparation and application thereof | |
| CN108690042B (en) | Simultaneous detection of ONOO-And H2Fluorescent probe of S and synthetic method and application thereof | |
| CN113136205A (en) | Fluorescent carbon quantum dot, preparation method and application thereof in detecting superoxide anion | |
| CN111504964B (en) | MOF-Cd probe for detecting lysine as well as preparation method and application thereof | |
| CN111233876B (en) | Fluorescent probe for detecting hydrogen sulfide and preparation method and application thereof | |
| CN113278157B (en) | Cadmium coordination polymer and preparation method and application thereof | |
| CN112745340B (en) | Selective detection of H based on BODIPY dye targeting lysosome2Fluorescent probe of S, preparation and application | |
| CN111233928B (en) | Coumarin derivative Mito-Cys and preparation method and application thereof | |
| CN111362958B (en) | Rhodamine fluorescent probe for specifically recognizing reduced GSH (glutathione), and preparation method and application thereof | |
| CN109283163B (en) | Method for detecting L-cysteine based on calcium-metal organic framework material as fluorescent probe | |
| CN117347336A (en) | Fluorescent aptamer biosensor for detecting kanamycin and preparation method and application thereof | |
| CN110964044B (en) | Peroxynitrite fluorescent probe based on dicoumarin derivative, preparation method and application | |
| CN117105760A (en) | Compound for recognizing chiral histidine, fluorescent probe, preparation method and application thereof | |
| CN110950877B (en) | Double-detection fluorescent probe, preparation method and application thereof in detection of hydrogen sulfide and copper ions | |
| CN111808061B (en) | Dual-channel fluorescent probe for distinguishing and detecting GSH and hydrogen polysulfide | |
| CN114805178A (en) | Fluorescent probe for detecting bisulfite ions, preparation thereof and application thereof in food detection | |
| CN111187289B (en) | Hydrogen peroxide fluorescent probe and preparation method and application thereof | |
| CN114349717A (en) | Benzothiazole derivative cysteine-based fluorescent probe and preparation method thereof | |
| CN110183515B (en) | Polypeptide for PTP1B detection and fluorescent probe containing polypeptide | |
| CN109781678B (en) | Preparation and application of ratiometric fluorescent probe applied to intramitochondrial hypochlorous acid detection | |
| CN110498795B (en) | Imidazo [1,2-a ] pyridine derivative cysteine fluorescent probe and application thereof | |
| CN113121552A (en) | Synthesis and application of fluorescent probe for selectively detecting cysteine |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |