CN105001852B - A kind of preparation method and application of the magnetic pyrene butanoic acid fluorescent probe detecting ferric ion - Google Patents
A kind of preparation method and application of the magnetic pyrene butanoic acid fluorescent probe detecting ferric ion Download PDFInfo
- Publication number
- CN105001852B CN105001852B CN201510304316.4A CN201510304316A CN105001852B CN 105001852 B CN105001852 B CN 105001852B CN 201510304316 A CN201510304316 A CN 201510304316A CN 105001852 B CN105001852 B CN 105001852B
- Authority
- CN
- China
- Prior art keywords
- butanoic acid
- magnetic
- pyrene butanoic
- fluorescent probe
- ferric ion
- 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
Abstract
The present invention relates to the preparation method and application of a kind of magnetic pyrene butanoic acid fluorescent probe detecting ferric ion, belong to new function material and technical field of analytical chemistry.Ferroso-ferric oxide has preferable magnetic, 1 pyrene butanoic acid has preferable fluorescence property, both are combined, the magnetic of ferroso-ferric oxide can be kept, the fluorescence property of 1 pyrene butanoic acid can be kept again, thus realize the detection to ferric ion and separation, it is limited to 0.01 mmol/L, the range of linearity 0.5 ~ 300 mmol/L for analyzing the detection of ferric ion.
Description
Technical field
The present invention relates to the preparation method and application of a kind of magnetic pyrene butanoic acid fluorescent probe detecting ferric ion, belong to new function material and chemical analysis technology field.
Background technology
Fe3+It is not only a kind of heavy metal ion, and it is also one of most important trace element in human body.It is present in many enzymes and protein, and as the cofactor of cellular metabolism reaction.Fe3+Blood can promote the formation of hemoglobin, and iron deficiency can cause people's anemia.But, the iron content of excess can damage biological system, this is because its redox form can be catalyzed generation high activity oxygen, and this material can participate in multiple disease, such as handkerchief parasol pine syndrome, Alzheimer’s disease and cancer.Therefore, in human body, the assay of iron ion is a very important problem.
Fluorescence analysis measures has simple to operate, highly sensitive and efficiency advantages of higher, has become one of most popular method.
1-pyrene butanoic acid is the fluorescent dye of a kind of Fourth Ring aromatics anionic, and this material is used for Fe3+Detection there is not been reported.
Ferroso-ferric oxide Fe3O4As the nano-particle bought, there is ferromagnetism, the steerable performance of magnetic and preferable biocompatibility, be widely used in multiple fields, such as biomagnetism separation, medicament transport release and nuclear magnetic resonance.
Ferroso-ferric oxide is connected by 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride and N-hydroxy-succinamide by the present invention with 1-pyrene butanoic acid, and uses it for the detection of ferric ion.The preparation condition of magnetic pyrene butanoic acid fluorescent probe is gentle and environmentally friendly.Magnetic pyrene butanoic acid fluorescent probe can not only keep the magnetic of ferroso-ferric oxide, moreover it is possible to keeps the fluorescence property of 1-pyrene butanoic acid, is capable of the detection to ferric ion and removal, so that magnetic pyrene butanoic acid fluorescent probe has preferable using value simultaneously.
Summary of the invention
An object of the present invention is to prepare a kind of magnetic pyrene butanoic acid fluorescent probe quick, overdelicate.
The two of the purpose of the present invention are detection and the removals that magnetic pyrene butanoic acid fluorescent probe is used for ferric ion.
Technical scheme is as follows:
1. the preparation of amination ferroso-ferric oxide, step is as follows:
The ferric chloride of 1 ~ 3 g is dissolved in 20 ~ 60 mL ethylene glycol, add anhydrous sodium acetate and the anhydrous ethylenediamine of 10 ~ 30 mL of 3 ~ 9 g, mixed liquor mechanical agitation 30 min, mixed liquor is transferred in politef reactor, 8 h are reacted at 200 DEG C, product is through Magneto separate, and cleans 3 ~ 6 times with dehydrated alcohol and water, is vacuum dried 12 h at 60 DEG C.
2. the preparation of magnetic pyrene butanoic acid fluorescent probe, step is as follows:
Weigh 10 ~ 30 mg amination ferroferric oxide nano granules, be scattered in 4 ~ 12 mL ultra-pure waters, ultrasonic 30 min, be allowed to form uniform dispersion liquid；Add and shake 12 h under the 1-pyrene butanoic acid of 200 mg and 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride that 1 ~ 3 mL molar concentration rate is 1:1 and N-hydroxy-succinamide mixed solution, room temperature；Under the effect of external magnetic field, carrying out unconjugated 1-pyrene butanoic acid separating and cleaning 3 ~ 5 times with distilled water, product vacuum is dried 6 h, prepares magnetic pyrene butanoic acid fluorescent probe；
Weigh 10 ~ 30 mg magnetic pyrene butanoic acid fluorescent probes, be scattered in 100 ~ 300
ML, volume ratio are in the dehydrated alcohol of 1: 1 and the mixed liquor of water, prepare the storing solution of magnetic pyrene butanoic acid fluorescent probe, save backup in 4 DEG C of refrigerators.
3. magnetic pyrene butanoic acid fluorescent probe application in ferric ion detects, step is as follows:
(1) preparation method according to claim 1 prepares a kind of magnetic pyrene butanoic acid fluorescent probe detecting ferric ion；
(2) arranging fluorescent instrument parameter: excitation wavelength is 300 nm, launching wave-length coverage is 350 ~ 480 nm, and exciting slit width is 10 nm, and launching slit width is 20 nm, and scanning speed is 1200 nm/min；The magnetic pyrene butanoic acid storing solution of 150 ~ 350 L is distributed to 10 mL, 20 mmol/L, pH 5.0 ~
In the PBS buffer solution of 8.49, the fluorescence spectrum of the ferric ion standard solution of detection variable concentrations, according to relation, drawing curve between magnetic pyrene butanoic acid fluorescent probe fluorescence intensity and the concentration of ferric ion at 395 nm；
(3) human serum sample's solution to be measured is replaced ferric ion standard solution, detect according to the working curve method for drafting of described iron ion.
The useful achievement of the present invention
(1) magnetic ferroferric oxide is incorporated in the preparation of magnetic fluorescence probe, utilizes the advantage such as the steerable performance of the ferromagnetism of magnetic ferroferric oxide, magnetic and preferable biocompatibility, it is possible to achieve the separation to object.
(2) utilize the 1-preferable fluorescence property of pyrene butanoic acid, use it for preparing magnetic pyrene butanoic acid, it is possible to achieve the analysis to object detects.
(3) with 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride and N-hydroxy-succinamide mixed solution activation amino and carboxyl, the preparation process of the magnetic pyrene butanoic acid fluorescent probe made is simple to operation, and environmental sound, process green cleans.
(4) the magnetic pyrene butanoic acid fluorescent probe that prepared by the present invention is possible not only to Selective recognition ferric ion, can also quickly be removed by iron ion simultaneously, have response time short from solution, the advantages such as detection limit is low, range of linearity width.It is limited to 0.01 mmol/L, the range of linearity 0.5 ~ 300 mmol/L for analyzing the detection of ferric ion.
Detailed description of the invention
Embodiment 1 The preparation of amination ferroso-ferric oxide
The ferric chloride of 1 g is dissolved in 20 mL ethylene glycol, add anhydrous sodium acetate and the anhydrous ethylenediamine of 10 mL of 3 g, mixed liquor mechanical agitation 30 min, mixed liquor is transferred in politef reactor, 8 h are reacted at 200 DEG C, product is through Magneto separate, and cleans 3 ~ 6 times with dehydrated alcohol and water, is vacuum dried 12 h at 60 DEG C.
Embodiment 2 The preparation of amination ferroso-ferric oxide
The ferric chloride of 2 g is dissolved in 40 mL ethylene glycol, add anhydrous sodium acetate and the anhydrous ethylenediamine of 20 mL of 6 g, mixed liquor mechanical agitation 30 min, mixed liquor is transferred in politef reactor, 8 h are reacted at 200 DEG C, product is through Magneto separate, and cleans 3 ~ 6 times with dehydrated alcohol and water, is vacuum dried 12 h at 60 DEG C.
Embodiment 3The preparation of amination ferroso-ferric oxide
The ferric chloride of 3 g is dissolved in 60 mL ethylene glycol, add anhydrous sodium acetate and the anhydrous ethylenediamine of 30 mL of 9 g, mixed liquor mechanical agitation 30 min, mixed liquor is transferred in politef reactor, 8 h are reacted at 200 DEG C, product is through Magneto separate, and cleans 3 ~ 6 times with dehydrated alcohol and water, is vacuum dried 12 h at 60 DEG C；
Embodiment 4The preparation of magnetic pyrene butanoic acid fluorescent probe
Weigh 10 amination ferroferric oxide nano granules, be scattered in 4mL ultra-pure water, ultrasonic 30
Min, is allowed to form uniform dispersion liquid；Add and shake 12 h under the 1-pyrene butanoic acid of 200 mg and 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride that 1 mL molar concentration rate is 1:1 and N-hydroxy-succinamide mixed solution, room temperature；Under the effect of external magnetic field, carrying out unconjugated 1-pyrene butanoic acid separating and cleaning 3 ~ 5 times with distilled water, product vacuum is dried 6 h, prepares magnetic pyrene butanoic acid fluorescent probe；
Weigh 10 mg magnetic pyrene butanoic acid fluorescent probes, be scattered in 100 mL, volume ratio is the dehydrated alcohol of 1: 1 and in the mixed liquor of water, prepare the storing solution of magnetic pyrene butanoic acid fluorescent probe, save backup in 4 DEG C of refrigerators.
Embodiment 5The preparation of magnetic pyrene butanoic acid fluorescent probe
Weigh 20 mg amination ferroferric oxide nano granules, be scattered in 8 mL ultra-pure waters, ultrasonic 30 min, be allowed to form uniform dispersion liquid；Add and shake 12 h under the 1-pyrene butanoic acid of 200 mg and 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride that 2 mL molar concentration rates are 1:1 and N-hydroxy-succinamide mixed solution, room temperature；Under the effect of external magnetic field, carrying out unconjugated 1-pyrene butanoic acid separating and cleaning 3 ~ 5 times with distilled water, product vacuum is dried 6 h, prepares magnetic pyrene butanoic acid fluorescent probe；
Weigh 20 mg magnetic pyrene butanoic acid fluorescent probes, be scattered in 200 mL, volume ratio is the dehydrated alcohol of 1: 1 and in the mixed liquor of water, prepare the storing solution of magnetic pyrene butanoic acid fluorescent probe, save backup in 4 DEG C of refrigerators.
Embodiment 6The preparation of magnetic pyrene butanoic acid fluorescent probe
Weigh 30 mg amination ferroferric oxide nano granules, be scattered in 12 mL ultra-pure waters, ultrasonic 30 min, be allowed to form uniform dispersion liquid；Add and shake 12 h under the 1-pyrene butanoic acid of 200 mg and 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride that 3 mL molar concentration rates are 1:1 and N-hydroxy-succinamide mixed solution, room temperature；Under the effect of external magnetic field, carrying out unconjugated 1-pyrene butanoic acid separating and cleaning 3 ~ 5 times with distilled water, product vacuum is dried 6 h, prepares magnetic pyrene butanoic acid fluorescent probe；
Weigh 30 mg magnetic pyrene butanoic acid fluorescent probes, be scattered in 300 mL, volume ratio is the dehydrated alcohol of 1: 1 and in the mixed liquor of water, prepare the storing solution of magnetic pyrene butanoic acid fluorescent probe, save backup in 4 DEG C of refrigerators.
Embodiment 7Magnetic pyrene butanoic acid fluorescent probe is for the detection of ferric ion, and step is as follows:
(1) preparation method according to claim 1 prepares a kind of magnetic pyrene butanoic acid fluorescent probe detecting ferric ion；
(2) arranging fluorescent instrument parameter: excitation wavelength is 300 nm, launching wave-length coverage is 350 ~ 480
Nm, exciting slit width is 10 nm, and launching slit width is 20 nm, and scanning speed is 1200 nm/min.By 150
The magnetic pyrene butanoic acid storing solution of L is distributed to 10 mL, 20 mmol/L, pH
In the PBS buffer solution of 5.0 ~ 8.49, the fluorescence spectrum of the ferric ion standard solution of detection variable concentrations, according to relation, drawing curve between magnetic pyrene butanoic acid fluorescent probe fluorescence intensity and the concentration of ferric ion at 395 nm；
(3) human serum sample's solution to be measured is replaced ferric ion standard solution, detect according to the working curve method for drafting of described iron ion.Its detection is limited to 0.01 mmol/L, the range of linearity 0.5 ~ 300 mmol/L.
Embodiment 8Magnetic pyrene butanoic acid fluorescent probe is for the detection of ferric ion, and step is as follows:
(1) preparation method according to claim 1 prepares a kind of magnetic pyrene butanoic acid fluorescent probe detecting ferric ion；
(2) arranging fluorescent instrument parameter: excitation wavelength is 300 nm, launching wave-length coverage is 350 ~ 480
Nm, exciting slit width is 10 nm, and launching slit width is 20 nm, and scanning speed is 1200 nm/min.By 250
The magnetic pyrene butanoic acid storing solution of L is distributed to 10 mL, 20 mmol/L, pH
In the PBS buffer solution of 5.0 ~ 8.49, the fluorescence spectrum of the ferric ion standard solution of detection variable concentrations, according to relation, drawing curve between magnetic pyrene butanoic acid fluorescent probe fluorescence intensity and the concentration of ferric ion at 395 nm；
(3) human serum sample's solution to be measured is replaced ferric ion standard solution, detect according to the working curve method for drafting of described iron ion.
Embodiment 9Magnetic pyrene butanoic acid fluorescent probe is for the detection of ferric ion, and step is as follows:
(1) preparation method according to claim 1 prepares a kind of magnetic pyrene butanoic acid fluorescent probe detecting ferric ion；
(2) arranging fluorescent instrument parameter: excitation wavelength is 300 nm, launching wave-length coverage is 350 ~ 480
Nm, exciting slit width is 10 nm, and launching slit width is 20 nm, and scanning speed is 1200 nm/min.By 350
The magnetic pyrene butanoic acid storing solution of L is distributed to 10 mL, 20 mmol/L, pH
In the PBS buffer solution of 5.0 ~ 8.49, the fluorescence spectrum of the ferric ion standard solution of detection variable concentrations, according to relation, drawing curve between magnetic pyrene butanoic acid fluorescent probe fluorescence intensity and the concentration of ferric ion at 395 nm；
(3) human serum sample's solution to be measured is replaced ferric ion standard solution, detect according to the working curve method for drafting of described iron ion.
Claims (2)
1. the preparation method of the magnetic pyrene butanoic acid fluorescent probe detecting ferric ion, it is characterised in that step is as follows:
The synthesis of amination ferroso-ferric oxide
The ferric chloride of 1 ~ 3 g is dissolved in 20 ~ 60 mL ethylene glycol, add anhydrous sodium acetate and the anhydrous ethylenediamine of 10 ~ 30 mL of 3 ~ 9 g, mixed liquor mechanical agitation 30 min, mixed liquor is transferred in politef reactor, 8 h are reacted at 200 DEG C, product is through Magneto separate, and cleans 3 ~ 6 times with dehydrated alcohol and water, is vacuum dried 12 h at 60 DEG C；
The synthesis of magnetic pyrene butanoic acid fluorescent probe
Weigh 10 ~ 30 mg amination ferroferric oxide nano granules, be scattered in
In 4 ~ 12 mL ultra-pure waters, ultrasonic 30 min, it is allowed to form uniform dispersion liquid；Add and shake 12 h under the 1-pyrene butanoic acid of 200 mg and 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride that 1 ~ 3 mL molar concentration rate is 1:1 and N-hydroxy-succinamide mixed solution, room temperature；Under the effect of external magnetic field, carrying out unconjugated 1-pyrene butanoic acid separating and cleaning 3 ~ 5 times with distilled water, product vacuum is dried 6 h, prepares magnetic pyrene butanoic acid fluorescent probe；
Weigh 10 ~ 30 mg magnetic pyrene butanoic acid fluorescent probes, be scattered in 100 ~ 300 mL, volume ratio is the dehydrated alcohol of 1: 1 and in the mixed liquor of water, prepare the storing solution of magnetic pyrene butanoic acid fluorescent probe, save backup in 4 DEG C of refrigerators.
A kind of magnetic pyrene butanoic acid fluorescent probe detecting ferric ion prepared by preparation method the most according to claim 1 detects for ferric ion, it is characterised in that step is as follows:
(1) preparation method according to claim 1 prepares a kind of magnetic pyrene butanoic acid fluorescent probe detecting ferric ion；
(2) arranging fluorescent instrument parameter: excitation wavelength is 300 nm, launching wave-length coverage is 350 ~ 480 nm, and exciting slit width is 10 nm, and launching slit width is 20 nm, and scanning speed is 1200 nm/min；The magnetic pyrene butanoic acid storing solution of 150 ~ 350 L is distributed in the PBS buffer solution of 10 mL, 20 mmol/L, pH 5.0 ~ 8.49, the fluorescence spectrum of the ferric ion standard solution of detection variable concentrations, according to relation, drawing curve between magnetic pyrene butanoic acid fluorescent probe fluorescence intensity and the concentration of ferric ion at 395 nm；
(3) human serum sample's solution to be measured is replaced ferric ion standard solution, detect according to the working curve method for drafting of described iron ion.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510304316.4A CN105001852B (en) | 2015-06-08 | 2015-06-08 | A kind of preparation method and application of the magnetic pyrene butanoic acid fluorescent probe detecting ferric ion |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510304316.4A CN105001852B (en) | 2015-06-08 | 2015-06-08 | A kind of preparation method and application of the magnetic pyrene butanoic acid fluorescent probe detecting ferric ion |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN105001852A CN105001852A (en) | 2015-10-28 |
| CN105001852B true CN105001852B (en) | 2016-10-12 |
Family
ID=54374725
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510304316.4A Active CN105001852B (en) | 2015-06-08 | 2015-06-08 | A kind of preparation method and application of the magnetic pyrene butanoic acid fluorescent probe detecting ferric ion |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN105001852B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109439314B (en) * | 2018-12-07 | 2022-05-10 | 武汉工程大学 | Preparation method of magnetic nano fluorescent probe for specifically recognizing Fe (III) |
| CN109900670B (en) * | 2019-04-02 | 2021-07-06 | 济南大学 | Bifunctional probe for identifying iron ions and fluorine ions, and preparation and application thereof |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102127586A (en) * | 2010-12-08 | 2011-07-20 | 苏州同科生物材料有限公司 | Magnetic fluorescent bifunctional nano biological probe and preparation method thereof |
| CN103235145B (en) * | 2013-04-19 | 2014-04-23 | 济南大学 | Preparation method and application of two-channel environmental estrogen immunosensor |
| CN103864640B (en) * | 2014-02-27 | 2015-12-09 | 华南师范大学 | Nitrogen, nitrogen '-two pyrene butyryl radicals ornithine and application thereof |
| CN104045857B (en) * | 2014-06-16 | 2016-04-13 | 安徽师范大学 | A kind of silicon-dioxide Chitosan Composites, preparation method and application thereof |
| CN104262811A (en) * | 2014-09-19 | 2015-01-07 | 哈尔滨工业大学 | Preparation method and application of polystyrene fluorescent microspheres |
-
2015
- 2015-06-08 CN CN201510304316.4A patent/CN105001852B/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN105001852A (en) | 2015-10-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Yang et al. | Synthesis of highly fluorescent lysine-stabilized Au nanoclusters for sensitive and selective detection of Cu 2+ ion | |
| CN102749317B (en) | Surface enhanced Raman scattering probe based on carbon nanotube and preparation method thereof | |
| Afshar et al. | Magnetic nanoparticles based on cerium MOF supported on the MWCNT as a fluorescence quenching sensor for determination of 6-mercaptopurine | |
| Dang et al. | Intensive and persistent chemiluminescence system based on nano-/bioenzymes with local tandem catalysis and surface diffusion | |
| CN109668874A (en) | A kind of preparation method of the electrochemical luminescence immunosensor of different luminol functionalization MOFs detection beta-amyloid protein | |
| CN101530798A (en) | New reagent for testing the content of hydrogen peroxide and new method thereof | |
| WO2018054391A1 (en) | Intracellular atp circular dichroism spectrum real-time detection method | |
| CN107254307B (en) | Silver nanocluster fluorescent vesicle and preparation method thereof and Fe detection method3+Application of | |
| Yu et al. | Two-stage ligand exchange in Mn (III)-based porphyrinic metal− organic frameworks for fluorescence water sensing | |
| CN105784820A (en) | Method of adapter sensor of silk-printed carbon electrode for detecting microcystic toxin | |
| CN105001852B (en) | A kind of preparation method and application of the magnetic pyrene butanoic acid fluorescent probe detecting ferric ion | |
| Bobba et al. | Resorufin based fluorescence ‘turn-on’chemodosimeter probe for nitroxyl (HNO) | |
| Zhang et al. | Colorimetric detection of bis-phosphorylated peptides using zinc (ii) dipicolylamine-appended gold nanoparticles | |
| CN104818016B (en) | A kind of method for tervalence gold ion detection | |
| CN112852418A (en) | Double-emission-ratio fluorescent carbon dot and preparation method and application thereof | |
| CN104178483B (en) | A kind of fluorescence nargol and its preparation method and application | |
| CN108752373B (en) | Fluorescent probe for identifying hydrogen peroxide based on phenylboronate | |
| Yang et al. | A stepwise recognition strategy for the detection of telomerase activity via direct electrochemical analysis of metal–organic frameworks | |
| CN103193826B (en) | Nanocluster and preparation method thereof and application | |
| CN106084232A (en) | The preparation of fluorescence magnetic graphite oxide thiazolinyl 4 chlorophenol molecularly imprinted polymer and application | |
| Han et al. | Determination of tetracycline, chlortetracycline and oxytetracycline by flow injection with inhibitory chemiluminescence detection using copper (II) as a probe ion | |
| CN104568882A (en) | Method for preparing glucose optical nanosensor | |
| CN104897627B (en) | A kind of method of the fluoroscopic examination folic acid based on molecular recognition | |
| CN108760695B (en) | Method for quantitatively detecting thrombin by using phosphorescence probe based on PRET | |
| CN109283163A (en) | Method based on calcium-metal-organic framework materials as fluorescence probe detection L-cysteine |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant |