CN108658893A - A kind of fluorescent molecular probe compound, preparation method and the application in detection L-cysteine - Google Patents
A kind of fluorescent molecular probe compound, preparation method and the application in detection L-cysteine Download PDFInfo
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- CN108658893A CN108658893A CN201810589214.5A CN201810589214A CN108658893A CN 108658893 A CN108658893 A CN 108658893A CN 201810589214 A CN201810589214 A CN 201810589214A CN 108658893 A CN108658893 A CN 108658893A
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- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
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- 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"
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- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
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Abstract
The invention discloses a kind of fluorescent molecular probe compound, preparation method and in the application for detecting L cysteines.The fluorescence probe of the present invention, structural formula are as follows：Invention also provides the preparation methods of the probe.Blue-fluorescence is presented in fluorescence probe provided by the invention itself in buffer solution, can have the product of yellow-green fluorescence with specific reaction, generation occurs with L cysteines, to realize the specificly-response to L cysteines.This probe steady it is good thus being capable of long-term preservation and use.Probe has selectivity well to L cysteines.
Description
Technical field
The invention discloses a kind of fluorescence probe that can detect L-cysteine (L-Cysteine, L-cys) and its synthesis
Methods and applications, more particularly to a kind of fluorescence probe that can detect L-cysteine by different emission, belonging to
Learn technical field of analysis and detection.
Background technology
L-cysteine is a kind of amino acid common in organism, can (methionine, human body must by internal methionine
Need amino acid) it is transformed, it can be with the mutual inversion of phases of cystine.
The decomposition of cysteine be under anaerobic by take off the effect of sulfhydryl enzyme resolve into pyruvic acid and hydrogen sulfide and
Ammonia, or by transamination, it is decomposed into pyruvic acid and Sulfur via intermediate product mercaptopyruvic acid, in oxidation item
Under the conditions of, after being oxidized to cysteine sulfurous acid, pyruvic acid and sulfurous acid can be decomposed into through transamination, and by decarboxylation
Hypotaurine, taurine etc. are decomposed into base effect.In addition, cysteine is unstable compound, it is easy redox, with
Cystine is mutually converted.It can also be condensed into mercapturic acid (mercapturic acid) with toxic aromatic compound and be sent to a place under guard
Toxic action.
Cysteine is a kind of naturally-produced amino acid, has many purposes in food processing, it is mainly used for roasting
Baked goods, the required ingredient as flour-dough improver.Cysteine is a kind of reducing agent, it can promote the formation of gluten, subtract
Time needed for few mixing and required medicinal energy, cysteine pass through between change protein molecule and in protein molecule
The disulfide bond in portion, reduces the structure of protein, and such protein just extends.
L-cysteine is a kind of critically important a-amino acid containing sulfydryl, plays many important works in vivo
With, such as participate in protein synthesis, removing toxic substances, metabolism.L-cysteine can be found in many protein of human body
Presence, be one of most important constituent of biological related protein.L-cysteine additionally assists in maintaining Cellular Oxidation
Reduction activation, signal transduction and Gene regulation.If the content of L-cysteine, which deviates normal level, in cell can lead to many diseases
Disease, the health of harmful to human.Meanwhile L-cysteine is also widely used for the necks such as food industry, biological medicine, Biochemical Research
Domain.Therefore, establish it is a kind of simplicity, the L-cysteine detection method with good selectivity be a meaningful work
Make.Fluorescence chemical sensor have easy to operate, high sensitivity, selectivity is good, the response time is short, can also be measured in real time
The advantages that, be widely used in environment, in food and organism trace samplings detection.
Invention content
A kind of fluorescence probe that can detect L-cysteine of the present invention, molecular formula C23H14N2O2S2, structural formula
As follows：
A kind of fluorescence probe that can detect L-cysteine of the present invention, is realized by the following method：
A kind of fluorescence probe that can detect L-cysteine of the present invention, is realized by the following method：
Compound 1 and triethylamine are added in reaction bulb, while anhydrous methylene chloride is added as solvent, then ice bath (-
5~0 DEG C) under the conditions of be added needed for dosage acryloyl chloride.After stirring 0.5h, TLC contact plates monitoring reaction to raw material has been reacted
Entirely, by EA:PE=1:The eluant, eluent ratio of 6-15 crosses column and obtains target product.1H NMR(400MHz,DMSO)δ8.53(d,J
=8.0Hz, 1H), 8.18 (d, J=12Hz, 4H), 8.10 (t, J=8.0Hz, 2H), 7.58 (t, J=8.0Hz, 2H), 7.50
(t, J=8.0Hz, 2H), 6.74-6.61 (m, 2H), 6.35 (d, J=8.0Hz, 1H)13C NMR(101MHz,DMSO)δ
165.08, 163.87,160.55,153.40,152.10,148.18,135.68,134.94,134.82,130.54,
127.55,127.53,127.49, 126.93,126.88,126.04,125.31,123.19,123.11,122.51,
122.39,122.17.HRMS theoretical value：415.0569, experiment value:415.0560.
The present invention is by the fluorescent molecular probe compound in the application for detecting L-cysteine.
The synthesis of advantages of the present invention, probe only needs a step that can complete, and last handling process is simple.The choosing of probe
Selecting property is good, high sensitivity, shows selectivity good to L-cysteine and that amino acid coexists is good anti-interference to other
Ability.
Description of the drawings
Fig. 1 is 1 middle probe of embodiment1HNMR collection of illustrative plates.
Fig. 2 is 1 middle probe of embodiment13CNMR collection of illustrative plates.
Fig. 3 is the HRMS collection of illustrative plates of 1 middle probe of embodiment.
Fig. 4 is the fluorescence spectrum of 2 middle probe of embodiment detection L-cysteine.
The synthesis of 1 probe molecule of embodiment
Embodiment 1-1 adds to 36mg (0.10mmol) compound 1 and 40.4mg (0.4mmol) triethylamine in reaction bulb, is added simultaneously
As solvent, then at 0~5 DEG C after addition acryloyl chloride (0.3mL) reaction 0.5h, TLC contact plates monitor 5ml anhydrous methylene chlorides
To raw material, the reaction was complete for reaction, by EA:PE=1:The eluant, eluent ratio of 6-15 crosses column and obtains target product, yield 40%.
Embodiment 1-2 adds to 108mg (0.30mmol) compound 1 and 477.3mg (3mmol) triethylamine in reaction bulb,
10ml anhydrous methylene chlorides are added as solvent simultaneously, then after acryloyl chloride (0.2mL) reaction 0.5h is added at 0~5 DEG C,
To raw material, the reaction was complete for TLC contact plates monitoring reaction, by EA:PE=1:The eluant, eluent ratio of 6-15 crosses column and obtains target product, production
Rate is 37.7%.
108mg (0.30mmol) compound 1 and 151.78mg (1.5mmol) triethylamine are added to reaction bulb by embodiment 1-3
In, while 8ml anhydrous methylene chloride solution is added as solvent, then acryloyl chloride (0.5mL) is added at 0~5 DEG C and reacts
After 0.5h, to raw material, the reaction was complete for TLC contact plates monitoring reaction, by EA:PE=1:The eluant, eluent ratio of 6-15 crosses column and obtains target
Product, yield 40.7%.
Embodiment 1-4 adds to 108mg (0.30mmol) compound 1 and 417.3mg (3mmol) triethylamine in reaction bulb,
8ml anhydrous methylene chlorides are added as solvent simultaneously, then after acryloyl chloride (0.4mL) reaction 0.5h is added at 0~5 DEG C, TLC
To raw material, the reaction was complete for contact plate monitoring reaction, by EA:PE=1:The eluant, eluent ratio of 6-15 crosses column and obtains target product, and yield is
36.1%.
108mg (0.30mmol) compound 1 and 155.2mg (1.53mmol) triethylamine are added to reaction bulb by embodiment 1-5
In, while 8ml anhydrous methylene chlorides are added as solvent, then be added at 0~5 DEG C after acryloyl chloride (0.5mL) reacts 0.5h,
To raw material, the reaction was complete for TLC contact plates monitoring reaction, by EA:PE=1:The eluant, eluent ratio of 6-15 crosses column and obtains target product, production
Rate is 26.7%.
2 probe in detecting L-cysteine of embodiment
Fluorescent probe compounds prepared by Example 1, are dissolved into DMSO solution, and the probe for being configured to 500umol is female
L-cysteine is dissolved into distilled water by liquid, is configured to the L-cysteine mother liquor of 10mmol.Configure acetonitrile：Hep buffer solutions
(0.01mM, pH=7.4)=4：6 spectrum solution, every test tube 3mL.6 μ L (1 μM) are taken out from probe mother liquor to be added to often
In root test tube, take the L-cysteine mother liquor of different volumes in the aforementioned test tube for filling 3mL spectrum solution and probe.Reaction
After 35 minutes, using the excitation wave of 350nm, with Fluorescence Spectrometer test probe and various concentration (0,5,10,15,20,23.3,
26.7,30,33.3,40,50,60,80,100,120,140,160,180,200,250,3 00,350,400 μM) half Guangs of L-
The fluorescence spectrum of propylhomoserin changes.Fluorescence spectrum situation of change is as shown in Figure 4.The results show that with the L- half that various concentration is added
After cystine, fluorescent emission enhances at 523nm.
Claims (5)
1. a kind of fluorescent molecular probe compound, which is characterized in that its molecular formula is：C23H14N2O2S2；Structural formula is as follows：
2. a kind of synthetic method of fluorescent molecular probe compound described in claim 1, which is characterized in that synthetic method is such as
Under：
Compound 1 and triethylamine are added in reaction bulb, solvent is added, acryloyl chloride is then added at 0~5 DEG C, stirring is anti-
It answers, to raw material, the reaction was complete for TLC contact plates monitoring reaction, and column chromatography obtains target product；The synthetic route of this method is as follows：
3. the synthetic method of the fluorescent molecular probe compound described in claim 2, it is characterised in that：Compound 1, acryloyl
Chlorine, triethylamine molar ratio be 1：10-20：5-10.
4. the synthetic method of the fluorescent molecular probe compound described in claim 2, it is characterised in that：The solvent is anhydrous
Dichloromethane.
5. the fluorescent molecular probe compound being prepared described in claim any one of 2-4 answering in detection L-cysteine
With.
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| CN201810589214.5A CN108658893A (en) | 2018-06-08 | 2018-06-08 | A kind of fluorescent molecular probe compound, preparation method and the application in detection L-cysteine |
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| CN201810589214.5A CN108658893A (en) | 2018-06-08 | 2018-06-08 | A kind of fluorescent molecular probe compound, preparation method and the application in detection L-cysteine |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110003890A (en) * | 2019-04-28 | 2019-07-12 | 三峡大学 | Ratio type fluorescence probe, preparation method and the application on detection hydrazine hydrate |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013019978A1 (en) * | 2011-08-03 | 2013-02-07 | State Of Oregon Acting By And Through The State Board Of Higher Education On Behalf Of Portland State University | Fluorescence detection of cysteine and homocysteine |
| US20150177255A1 (en) * | 2013-12-23 | 2015-06-25 | Scintillon Research LLC | Novel fluorescent dyes, labeled conjugates and analytical methods |
-
2018
- 2018-06-08 CN CN201810589214.5A patent/CN108658893A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013019978A1 (en) * | 2011-08-03 | 2013-02-07 | State Of Oregon Acting By And Through The State Board Of Higher Education On Behalf Of Portland State University | Fluorescence detection of cysteine and homocysteine |
| US20150177255A1 (en) * | 2013-12-23 | 2015-06-25 | Scintillon Research LLC | Novel fluorescent dyes, labeled conjugates and analytical methods |
Non-Patent Citations (4)
| Title |
|---|
| I. S. IRGIBAEVA ET AL.: "Research of Electronic Absorption Spectra of Benzazols Derivatives by Ab Initio Calculations", 《INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY》 * |
| JOEL M. KAUFFMAN ET AL.: "Lack of progress on waveshifting fluors for use in or with polystyrene scintillators in high-energy particle detection", 《AIP CONFERENCE PROCEEDINGS》 * |
| MENG LI ET AL.: "A novel 2,5-bis(benzo[d]thiazol-2-yl)phenol scaffold-based ratiometric fluorescent probe for sensing cysteine in aqueous solution and serum", 《SPECTROCHIMICA ACTA PART A: MOLECULAR AND BIOMOLECULAR SPECTROSCOPY》 * |
| XIAOHONG ZHOU ET AL.: "A novel AIEE and EISPT fluorescent probe for selective detection of cysteine", 《TETRAHEDRON LETTERS》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110003890A (en) * | 2019-04-28 | 2019-07-12 | 三峡大学 | Ratio type fluorescence probe, preparation method and the application on detection hydrazine hydrate |
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