CN107141304A - A kind of fluoresceins cysteine fluorescence probe - Google Patents
A kind of fluoresceins cysteine fluorescence probe Download PDFInfo
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- CN107141304A CN107141304A CN201710341356.5A CN201710341356A CN107141304A CN 107141304 A CN107141304 A CN 107141304A CN 201710341356 A CN201710341356 A CN 201710341356A CN 107141304 A CN107141304 A CN 107141304A
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- cysteine
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/10—Spiro-condensed systems
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- 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
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- 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"
- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
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- 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
- G01N21/75—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated
- G01N21/77—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator
- G01N21/78—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator producing a change of colour
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
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- Optics & Photonics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Abstract
The invention discloses a kind of fluoresceins cysteine fluorescence probe, particular chemical formula is shown below：
Description
Technical field
The present invention relates to a kind of fluoresceins cysteine fluorescence probe and its detection cysteine in application.
Background technology
Cysteine (cysteine) belongs to one of 20 kinds of natural amino acids, is a kind of nonessential amino acid of sulfur-bearing.It is dynamic
It can be synthesized in object via methionine and serine.Damaging action of the radioactive ray to human body is repaired with alleviation.Cysteine is
Unstable compound, easy redox is mutually changed with cystine.Thioether can be condensed into poisonous aromatic compound
Propylhomoserin (mercapturic acid) and rise detoxication.Cysteine has many purposes in food processing, and it is mainly used
In baked goods, as the required composition of flour-dough improver, it is as a kind of reducing agent, and it can promote the formation of gluten, subtract
Time and required medicinal energy needed for few mixing, cysteine by change between protein molecule and protein molecule in
The disulfide bond in portion, reduces the structure of protein, and such protein is just extended.
At present, cysteine content method for measuring have gas chromatography-mass spectrometry, high performance liquid chromatography, it is complete from
Dynamic fluorescent polarization immunoassay, high performance capillary electrophoresis, organic molecule fluorescence probe detection method etc..In various methods
Organic molecule fluorescence probe detection method has simple, convenient, cost low, quick, sensitive and its potential intracellular due to it
The characteristics such as imaging, have proved to be a kind of very effective detection method, and many organic molecule fluorescence probes are opened at present
Issue.
Fluorescein has the feature such as stronger fluorescence intensity, excellent dissolubility, easily prepared, therefore as fluorescence probe
Use one of fluorophor widely.
The content of the invention
It is an object of the present invention to provide a kind of fluoresceins cysteine fluorescence probe, it is suitable in food, medicine, cosmetics
Deng detecting cysteine in product.
More particularly, the present invention relates to a kind of fluoresceins cysteine fluorescence probe, it is represented by following formula：
Brief description of the drawings
Fig. 1 is that in phosphate buffered saline solution, fluorescence probe (10 μM) of the invention is before (30 μM) additions of cysteine
Color change afterwards.
Fig. 2 is in phosphate buffered saline solution, with the addition of various concentrations cysteine, fluorescence probe of the invention
The fluorescence intensity change of (10 μM).Embedded figure：The concentration of cysteine.
Fig. 3 is that in phosphate buffered saline solution, fluorescence probe (10 μM) fluorescence intensity of the invention is dense with cysteine
Spend the standard curve of change.
Embodiment
The preparation of the fluoresceins cysteine fluorescence probe of embodiment 1.
Synthetic route is shown below：
By 1g (3mmol) A fluoresceins and 0.8g (3mmol) B 2,4- dinitrophenyl chlorides are added to 50mL three-necked flasks
In, then by one drop triethylamine be added thereto, add 10mL chloroforms, be heated to reflux 5h.Afterwards by the near room temperature of temperature, revolving
Concentration, column chromatographic isolation and purification (petroleum ether: ethyl acetate=5: 1), obtains white crystal 105mg.
Product is levied by nucleus magnetic hydrogen spectrum and nuclear-magnetism carbon stave.
1H NMR (300MHz, DMSO), δ (ppm)：10.25 (s, 1H), 8.91 (d, J=2.7Hz, 1H), 8.48 (dd, J
=9.3,2.7Hz, 1H), 8.00 (d, J=7.2Hz, 1H), 7.72-7.85 (m, 2H), 7.42 (d, J=9.3Hz, 1H), 7.26-
7.36 (m, 2H), 7.00 (dd, J=8.7,2.4Hz, 1H), 6.91 (d, J=8.7Hz, 1H), 6.70 (d, J=0.9Hz, 1H),
6.61 (s, 2H)
13C NMR (300MHz, DMSO)：δ(ppm)：169.1,160.2,156.1,154.2,152.8,152.4,151.9,
142.8,140.5,136.4,136.4,130.9,130.3,129.7,126.3,125.4,124.6,122.5,121.5,
117.0,116.2,113.7,109.6,108.5,102.8,82.4.
As shown in figure 1, with the addition of cysteine, the color of fluorescence probe solution of the invention is changed into yellow from light yellow
Green, the color change can be observed directly with human eye under natural light, show that the fluorescence probe of the present invention can be used for half Guang
The qualitative detection of propylhomoserin.The fluorescence intensity of the fluorescence probe of the present invention is as the change of semicystinol concentration is as shown in Fig. 2 foundation
The change can make the standard curve that fluorescence probe (10 μM) fluorescence intensity changes with semicystinol concentration, and standard curve is such as
Shown in Fig. 3, by the foundation of the standard curve, fluorescence probe of the invention can be used for the quantitative detection of cysteine.
Claims (2)
1. a kind of fluoresceins cysteine fluorescence probe, particular chemical formula is as follows：
2. fluorescence probe described in claim 1 detects the application of cysteine in food, medicine, cosmetics.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710341356.5A CN107141304A (en) | 2017-05-16 | 2017-05-16 | A kind of fluoresceins cysteine fluorescence probe |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710341356.5A CN107141304A (en) | 2017-05-16 | 2017-05-16 | A kind of fluoresceins cysteine fluorescence probe |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN107141304A true CN107141304A (en) | 2017-09-08 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710341356.5A Pending CN107141304A (en) | 2017-05-16 | 2017-05-16 | A kind of fluoresceins cysteine fluorescence probe |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108299427A (en) * | 2018-03-22 | 2018-07-20 | 泰山医学院 | Imidazopyridine Ben Bing oxadiazole class cysteine ratio fluorescent probes and its application |
| CN108362671A (en) * | 2018-02-23 | 2018-08-03 | 银川高新区广煜科技有限公司 | The method for detecting cysteine |
| CN108440551A (en) * | 2018-04-04 | 2018-08-24 | 中南大学 | A kind of fluorescence probe of detection biological thiol |
| CN110724114A (en) * | 2018-07-16 | 2020-01-24 | 北京工商大学 | Fluorescent probe for detecting bisulfite and hydrogen sulfide |
| CN111116433A (en) * | 2018-10-31 | 2020-05-08 | 北京工商大学 | Double-recognition-site hydrogen sulfide fluorescent probe |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060105412A1 (en) * | 2003-07-11 | 2006-05-18 | Osaka Industrial Promotion Organization | Sulfonate compound and fluorescent probe using the same |
-
2017
- 2017-05-16 CN CN201710341356.5A patent/CN107141304A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060105412A1 (en) * | 2003-07-11 | 2006-05-18 | Osaka Industrial Promotion Organization | Sulfonate compound and fluorescent probe using the same |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108362671A (en) * | 2018-02-23 | 2018-08-03 | 银川高新区广煜科技有限公司 | The method for detecting cysteine |
| CN108299427A (en) * | 2018-03-22 | 2018-07-20 | 泰山医学院 | Imidazopyridine Ben Bing oxadiazole class cysteine ratio fluorescent probes and its application |
| CN108440551A (en) * | 2018-04-04 | 2018-08-24 | 中南大学 | A kind of fluorescence probe of detection biological thiol |
| CN110724114A (en) * | 2018-07-16 | 2020-01-24 | 北京工商大学 | Fluorescent probe for detecting bisulfite and hydrogen sulfide |
| CN110724114B (en) * | 2018-07-16 | 2022-10-21 | 北京工商大学 | Fluorescent probe for detecting bisulfite and hydrogen sulfide |
| CN111116433A (en) * | 2018-10-31 | 2020-05-08 | 北京工商大学 | Double-recognition-site hydrogen sulfide fluorescent probe |
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Application publication date: 20170908 |