CN109651249A - A kind of fluorescence probe detecting endocytoplasmic reticulum cysteine and its synthesis and application - Google Patents
A kind of fluorescence probe detecting endocytoplasmic reticulum cysteine and its synthesis and application Download PDFInfo
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- CN109651249A CN109651249A CN201910014959.3A CN201910014959A CN109651249A CN 109651249 A CN109651249 A CN 109651249A CN 201910014959 A CN201910014959 A CN 201910014959A CN 109651249 A CN109651249 A CN 109651249A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
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Abstract
The present invention provides a kind of ratio type fluorescence probe for detecting endocytoplasmic reticulum cysteine, structural formula is.The probe has high specific to cysteine, and anti-interference, high sensitivity has good fluorescence emission spectral property, the real time measure for the cysteine that can be used in living cells endoplasmic reticulum.Fluorescence probe of the invention can be obtained through chemical synthesis, and synthesis technology is simple and easy, and raw material is cheap and easy to get, and preparation cost is low, easy to spread.
Description
Technical field
The invention belongs to small organic molecule fluorescence probe fields, and in particular to a kind of detection based on naphthalimide derivative
Cysteine fluorescence probe and its synthetic method in endocytoplasmic reticulum.
Background technique
Endoplasmic reticulum is widely present in the various eukaryocytes except mammal, is many in addition to nucleic acid in biological cell
Important biomolecule macromolecular, such as the base of protein, lipid and carbohydrate synthesis.Smooth surfaced endoplasmic reticulum also has function of detoxification, as liver is thin
Contain some enzymes in smooth surfaced endoplasmic reticulum in born of the same parents, to remove the harmful substance of fat-soluble waste and metabolism generation.Normal
Or under pathological state, endoplasmic reticulum generates er stress under the stimulation of extraneous factor, with cancer, AIDS sea silent disease, Parkinson
The generation of the major diseases such as disease is closely related.As reproducibility mercaptan generally existing in a kind of organism, cysteine can be with
It is maintained in endoplasmic reticulum as a kind of important regulator by the interaction with active oxygen during er stress
Redox state.On the other hand, excessive cysteine can lead to the abnormal metabolism, acid-base imbalance and oxidation of high homocysteine
Stress, there is very big toxic side effect to biosystem.Excessive cysteine can induce in endoplasmic reticulum and generate a large amount of vesica,
Promote the expression of CHOP albumen, and then activates er stress.Therefore, in real-time detection endoplasmic reticulum cysteine content for
Further investigated cysteine is of great significance in the biomechanism of endoplasmic reticulum, facilitates the research endoplasmic reticulum from cellular level and answers
Sharp physiology and pathologic process.
Compared to traditional electrochemical method, fluorescence imaging analysis method have high sensitivity, selectivity it is good, response rapidly,
Simple operation and other advantages, and biological sample is not damaged substantially, it is widely used in the intracorporal small molecule detection of various biologies.
What therefore exploitation was new has highly selective, highly sensitive, photostability and permeable membrane good, can detect cell endoplasm real-time, quickly
The fluorescence probe of cysteine has great importance in net.Compared to enhanced fluorescence probe, ratio type fluorescence probe not by
The influence of the extraneous factors such as probe environment, laser intensity, it is easier to obtain accurate test result.So far, endoplasmic reticulum targets
Ratio type cysteine fluorescence probe have not been reported.
Summary of the invention
Aiming at the problems existing in the prior art, the present invention provides a kind of ratio type for detecting endocytoplasmic reticulum cysteine
Fluorescence probe.
It is a further object of the present invention to provide a kind of synthetic method of above-mentioned fluorescence probe, raw material is easy to get, synthesis step is simple
Single, high income.
To achieve the above object, the present invention adopts the following technical scheme that.
A kind of ratio type fluorescence probe detecting endocytoplasmic reticulum cysteine, structural formula are as shown in the formula (I):
Formula (I).
A kind of synthetic method of above-mentioned ratio type fluorescence probe, comprising the following steps:
(1) compound 1 and n-Hydroxyphthalimide are in K2CO3DMSO solution in heat reaction, separate, purify to obtain change
Close object 2:
；
(2) compound 2, acryloyl chloride and N, N- diisopropylethylamine is in CH2Cl2Middle reaction separates, purifies to obtain pale yellow colored solid
Body detects the ratio type fluorescence probe of endocytoplasmic reticulum cysteine:
。
In step (1), the compound 1, n-Hydroxyphthalimide, K2CO3The mass ratio of the material be 0.25:
0.3:0.38。
In step (1), the heating temperature is 120 DEG C, reaction time 5h.
Separating-purifying step is to pour into reaction solution in cold water in step (1), uses HClO4It adjusts PH to Precipitation, filters
It is concentrated under reduced pressure under vacuum afterwards, with column chromatographic purifying；Eluent is the CH that volume ratio is 20:12Cl2And CH3The mixing of OH.
In step (2), the compound 2, acryloyl chloride, n,N-diisopropylethylamine the mass ratio of the material be 0.1:0.3:
0.1。
In step (2), the reaction time is 2.5h.
In step (2), the separating-purifying step is after reaction solution is concentrated under reduced pressure under vacuum, with column chromatographic purifying；
The CH that eluent is 50:12Cl2And CH3The mixing of OH.
A kind of application of above-mentioned ratio type fluorescence probe in detection endocytoplasmic reticulum cysteine.
In the application, excitation wavelength is 390 nm, and Detection wavelength is 440nm and 550nm.
In the application, when between 10-80 μM of semicystinol concentration, cysteine content and fluorescence intensity ratio I550/
I440It is linearly related.
The mechanism of action of the invention:
Fluorescence probe of the present invention can be applied to the detection evaluation of endocytoplasmic reticulum cysteine.The probe is as endoplasmic reticulum
The specific probe of cysteine, cysteine there are in the environment of, acrylate can be hydrolyzed to hydroxyl, generation has
The fluorescent material of high fluorescent emission ability, fluorescence probe can emit the green fluorescence (peak value of naphthalimide derivative dyestuff at this time
About 550 nm).The rapid sensitive detection that fluorescence detector realizes product, testing conditions are as follows: excitation wavelength 390 can be used
Nm carries out the detection of fluorescence emission spectrum between 400 ~ 700 nm.Pass through the fluorescence intensity ratio before detection response and after response
Value measures semicystinol concentration.
The invention has the benefit that
The fluorescence probe of detection endoplasmic reticulum cysteine of the present invention has high specific, is carrying out corresponding cysteine inspection
Substantially not by the interference of other components during surveying；High sensitivity has good fluorescence emission spectral property, can be used for living thin
The real time measure of cysteine in born of the same parents' endoplasmic reticulum.Fluorescence probe of the invention can be obtained through chemical synthesis, and synthesis technology is simple
Easy, raw material is cheap and easy to get, and preparation cost is low, easy to spread.
Detailed description of the invention
Fig. 1 is compound 21H NMR spectra；
Fig. 2 is fluorescence probe1H NMR spectra；
Fig. 3 is fluorescence spectrum of fluorescence probe under the conditions of various concentration cysteine；
Fig. 4 is the linear relationship data of fluorescence probe and semicystinol concentration；
Fig. 5 is the fluorescence spectrum after fluorescence probe is reacted with different material；
Fig. 6 is imaging applications of the fluorescence probe in living cells.
Specific embodiment
Below with reference to embodiment and attached drawing, the present invention will be further described, but the present invention is not by the limit of following embodiments
System.
The preparation of 1 cysteine fluorescence probe of embodiment
By compound 1(118mg, 0.25mmol), n-Hydroxyphthalimide (49mg, 0.3mmol), K2CO3(52mg,
It 0.38mmol) is dissolved in 4mLDMSO, stirring 5h is heated to reflux at 120 DEG C, reaction mixture is poured into 5mL cold water, is used
HClO4It adjusts PH to Precipitation, is concentrated under reduced pressure under vacuum after suction filtration, and use CH2Cl2: the eluent of MeOH=20:1 passes through column
Chromatographic purifying obtains yellow solid, is compound 2, yield 56%.Compound 21H NMR spectra is shown in Fig. 1:
；
By compound 2(41mg, 0.1mmol), acryloyl chloride (27mg, 0.3mmol), n,N-diisopropylethylamine (DIEA,
13mg, 0.1mmol) it is dissolved in 3mLCH2Cl2In, it is stirred to react 2.5h at room temperature, after being concentrated under reduced pressure under vacuum, is used in combination
CH2Cl2: the eluent of MeOH=50:1 obtains faint yellow solid by column chromatographic purifying, visits for detection endoplasmic reticulum cysteine fluorescence
Needle, yield 78%.Fluorescence probe1H NMR spectra is shown in Fig. 2:
。
Fluorescence spectrum of 2 fluorescence probe of embodiment under different semicystinol concentrations
It prepares the PBS buffer solution of 5 μM of embodiments, the 1 gained probe of 10 parts of 5mL in advance, contains 5% ethyl alcohol, cysteine be added
Solution to concentration be 0,10,20,30,40,50,60,70,80,90,100,110,120,130,140,150,160,170,180,
190,200 μM.Then fluorescence detection (λ is carried outEx=390nm), pass through the fluorescence intensity ratio at analysis 440nm and 550nm
(I550/I440) with the relationship of semicystinol concentration, assess the probe to the response performance of cysteine.It is with semicystinol concentration
Abscissa, with fluorescence intensity ratio (I550/I440) it is ordinate, Fig. 3 and Fig. 4 are respectively.From the figure 3, it may be seen that with cysteine
The increase of concentration, the fluorescence intensity ratio (I of solution550/I440) gradually increase.As shown in Figure 4, when semicystinol concentration is in 10-
Within the scope of 80 μM, the fluorescence intensity ratio (I of solution550/I440) and cysteine concentration be in preferable linear relationship.
The specificity of 3 fluorescence probe of embodiment
Prepare the PBS buffer solution (containing 5% ethyl alcohol, pH=7.4) of 5 μM of embodiments, the 1 gained fluorescence probe of 10 parts of 5mL in advance, so
Sequentially add Hcys, Na that 50 μ L concentration are 200 μM into the system respectively afterwards2S、Na2SO3、NO、H2O2、HClO4、Cys、
GSH、NaNO2, VC PBS solution (pH=7.4).Then fluorescence detection (λ is carried outEx=390nm), and it is strong to calculate fluorescence in each system
Spend ratio (I550/I440), different material is assessed to the interference of fluorescence probe, as a result such as Fig. 5.As shown in Figure 5, certain probe is molten
Hcys, Na are added in liquid2S、Na2SO3、NO、H2O2、HClO4、GSH、NaNO2, Vc when, only cysteine can lead to solution
The fluorescence of solution does not change substantially when generating significant change in fluorescence, and other small molecules are added, this indicates that the probe is only right
Cysteine has response, substantially not by the interference of other small molecules.
Imaging applications of 4 fluorescence probe of embodiment in living cells
Hela cell is placed in culture medium (DMEM culture solution and 10% fetal calf serum), 37 DEG C, 5%CO are placed in2And 20%O2Training
It supports in case and cultivates 24-48h.Contained with DMSO solution (concentration 1mM) injection that microsyringe draws probe obtained by 10 μ L embodiments
In the culture medium for having Hela cell, 30 min are cultivated in continuation in the incubator.Culture is rinsed with PBS buffer solution (pH=7.4) later
Cell 3 times, carry out fluorescence imaging.Then 100 μ L aqueous cystein solutions (concentration 1mM) are added, fluorescence imaging, knot are carried out
Fruit such as Fig. 6.By finding out in Fig. 6, when addition probe, cell has stronger blue-fluorescence and weaker green fluorescence；It adds
After cysteine, the blue-fluorescence of cell weakens, green fluorescence enhancing, this indicates that the probe can be used for detecting half in cell
Cystine.
Claims (9)
1. a kind of ratio type fluorescence probe for detecting endocytoplasmic reticulum cysteine, structural formula are as shown in the formula (I):
Formula (I).
2. a kind of synthetic method of ratio type fluorescence probe as described in claim 1, which comprises the following steps:
(1) compound 1 and n-Hydroxyphthalimide are in K2CO3DMSO solution in heat reaction, separate, purify to obtain change
Close object 2:
；
(2) compound 2, acryloyl chloride and N, N- diisopropylethylamine is in CH2Cl2Middle reaction separates, purifies to obtain faint yellow solid,
Detect endoplasmic reticulum cysteine fluorescence probe:
。
3. synthetic method according to claim 2, which is characterized in that in step (1), the compound 1, N- hydroxyl neighbour's benzene
Dicarboximide, K2CO3The mass ratio of the material be 0.25:0.3:0.38；
In step (2), the compound 2, acryloyl chloride, n,N-diisopropylethylamine the mass ratio of the material be 0.1:0.3:0.1.
4. synthetic method according to claim 2, which is characterized in that in step (1), the heating temperature is 120 DEG C, instead
It is 5h between seasonable；In step (2), reaction time 2.5h.
5. synthetic method according to claim 2, which is characterized in that separating-purifying step is in step (1), by reaction solution
It pours into cold water, uses HClO4It adjusts PH to Precipitation, is concentrated under reduced pressure under vacuum after suction filtration, with column chromatographic purifying；Eluent is
Volume ratio is the CH of 20:12Cl2And CH3The mixing of OH.
6. synthetic method according to claim 2, which is characterized in that in step (2), the separating-purifying step is will be anti-
After answering liquid to be concentrated under reduced pressure under vacuum, with column chromatographic purifying；The CH that eluent is 50:12Cl2And CH3The mixing of OH.
7. a kind of ratio type fluorescence probe as described in claim 1 is in the application of detection endocytoplasmic reticulum cysteine.
8. application according to claim 7, which is characterized in that excitation wavelength be 390 nm, Detection wavelength be 440nm and
550nm。
9. application according to claim 8, which is characterized in that when between 10-80 μM of semicystinol concentration, cysteine
Content and fluorescence intensity ratio I550/I440It is linearly related.
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Cited By (4)
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|---|---|---|---|---|
| CN110078665A (en) * | 2019-05-16 | 2019-08-02 | 济南大学 | A kind of hypochlorous fluorescence probe of detection of endoplasmic reticulum targeting and application |
| CN110563650A (en) * | 2019-08-27 | 2019-12-13 | 湖南大学 | Ratio type two-photon fluorescent probe of sulfatase, synthetic method and application thereof |
| CN112341374A (en) * | 2020-10-26 | 2021-02-09 | 山东师范大学 | Compound, preparation method and application of compound as pH ratio detection type fluorescent probe |
| CN115003678A (en) * | 2019-12-30 | 2022-09-02 | 塞尔吐温株式会社 | Real-time fluorescence imaging sensor for measuring glutathione in endoplasmic reticulum and method of using the same |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110078665A (en) * | 2019-05-16 | 2019-08-02 | 济南大学 | A kind of hypochlorous fluorescence probe of detection of endoplasmic reticulum targeting and application |
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| CN115003678B (en) * | 2019-12-30 | 2024-05-10 | 塞尔吐温株式会社 | Real-time fluorescence imaging sensor for measuring glutathione in endoplasmic reticulum and method of using the same |
| CN112341374A (en) * | 2020-10-26 | 2021-02-09 | 山东师范大学 | Compound, preparation method and application of compound as pH ratio detection type fluorescent probe |
| CN112341374B (en) * | 2020-10-26 | 2022-05-27 | 山东师范大学 | Compound, preparation method and application of compound as pH ratio detection type fluorescent probe |
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Application publication date: 20190419 |