CN107573287A - A kind of cation poly-phenylene vinylene (ppv) derivative and its preparation method and application - Google Patents
A kind of cation poly-phenylene vinylene (ppv) derivative and its preparation method and application Download PDFInfo
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Abstract
The invention provides a kind of cation poly-phenylene vinylene (ppv) derivative and its preparation method and application, derivative provided by the invention with structure shown in formula (I), quaternary ammonium salt group is modified by the side chain in derivative, that is side chain connection N methylimidazoles, make conjugated polymer positively charged, and then cause derivative provided by the invention that there is advantages below relative to other existing cell imaging agent：(1) fluorescence quantum yield is high, and (2) Stokes shift is big, and (3) biocompatibility is strong, (4) good light stability；And conjugated polymer can distribution of specific in lysosome, therefore, lysosome specificity image probe and long-time cell tracker agent can be used as.In addition, preparation method provided by the invention is simple, synthesis yield is high, it is easy to accomplish industrialization.
Description
Technical field
The present invention relates to biomedicine field, more particularly to a kind of cation poly-phenylene vinylene (ppv) derivative and its preparation side
Method and application
Background technology
Fluorescent nano probe is imaged in subcellular fraction, it is continuous follow the trail of cell carry out dynamic monitoring for example cell division, cell differentiation,
Played an important role in cell cycle circulation, Apoptosis etc..Conjugated polymer is a kind of big point with pi-conjugated system
Son, the fluorescence of different wave length can be launched according to the difference of its skeleton.Using this feature, conjugated polymer is as optical function material
It has been successfully applied to biomedicine field.
Lysosome is widely present in various cells in addition to bacteria, wherein containing kind of acid hydrolase about more than 60.It is molten
Enzyme body has extremely close relation, such as inflammation, silicosis, tumour and congenital lyase volume defect with many diseases
It is extremely relevant with lysosome etc. disease, it is significant therefore, it is possible to the lysosome that quick and precisely detects intracellular.
The content of the invention
In view of this, the technical problems to be solved by the invention are to provide a kind of cation poly-phenylene vinylene (ppv) derivative
And its preparation method and application, cation poly-phenylene vinylene (ppv) derivative provided by the invention can be used as lysosome specificity imaging
Probe, and long-time cell tracker agent can be used as.
The invention provides a kind of cation poly-phenylene vinylene (ppv) derivative, has structure shown in formula (I),
Wherein, the m1For 3~10；
The m2For 3~10；
The n is 5~10.
Preferably, the m1For 4,5,6,7,8 or 9.
Preferably, the m2For 4,5,6,7,8 or 9.
Present invention also offers a kind of preparation method of cation poly-phenylene vinylene (ppv) derivative, including：
The compound of formula (II) structure and N- methylimidazoles are reacted, obtain having the cation of formula (I) structure poly- to benzene
Support ethene derivatives；
Wherein, the m1For 3~10；
The m2For 3~10；
The n is 5~10.
Preferably, the compound of formula (II) structure is prepared in accordance with the following methods：
The compound of the compound of formula (III) structure and formula (IV) structure is reacted, obtains the compound of formula (II) structure；
Wherein, the m1For 3~10；
The m2For 3~10.
Preferably, the auxiliary agent of the reaction is palladium, trimethylphenyl phosphine oxide and n-butylamine.
Preferably, the compound and three n-butyl vinyl base tin of formula (III) structure of formula (IV) structure
Hybrid reaction obtains.
Preferably, the catalyst of the reaction is tetra-triphenylphosphine palladium, ferrocene palladium or palladium.
Present invention also offers a kind of fluorescence probe for being used to detect lysosome, the fluorescence probe is of the present invention
Cation poly-phenylene vinylene (ppv) derivative.
Present invention also offers a kind of cell tracker agent, including cation poly-phenylene vinylene (ppv) of the present invention to derive
Thing.
Compared with prior art, the invention provides a kind of cation poly-phenylene vinylene (ppv) derivative, have shown in formula (I)
Structure, wherein, by modifying quaternary ammonium salt group, i.e. side chain connection N- methylimidazoles in the side chain of derivative, make conjugated polymer
Positively charged, and then cause derivative provided by the invention that there is advantages below relative to other existing cell imaging agent：(1) it is glimmering
Quantum yield is high, and (2) Stokes shift is big, and (3) biocompatibility is strong, (4) good light stability；And conjugated polymer can be special
The opposite sex is distributed in lysosome, therefore, can be used as lysosome specificity image probe and long-time cell tracker agent.In addition, this
It is simple to invent the preparation method provided, synthesis yield is high, it is easy to accomplish industrialization.
Brief description of the drawings
Fig. 1 is the MCF-7 cell survival rate measurement results that the PPV of various concentrations is handled；
Fig. 2 is the common focused view of the MCF-7 cells with 30 μM of PPV and 1 μM of Lyso-Tracker processing simultaneously；
Fig. 3 is that PPV and Lyso-Tacker photostability determines curve；
Fig. 4 is simultaneously with the MCF-7 cell long-period images of 30 μM of PPV and 1 μM of Lyso-Tracker processing；
Fig. 5 is Confocal Images and fluorescence intensity image of the MCF-7 cells from 30 μM of PPV under different rejection conditions.
Embodiment
The invention provides a kind of cation poly-phenylene vinylene (ppv) derivative, has structure shown in formula (I),
Wherein, the m1For 3~10；
The m2For 3~10；
The n is 5~10.
Wherein, the m1Preferably 4,5,6,7,8 or 9, the m2Preferably 4,5,6,7,8 or 9, the n is preferably 6,7,
8 or 9.
Present invention also offers a kind of preparation method of cation poly-phenylene vinylene (ppv) derivative, including：
The compound of formula (II) structure and N- methylimidazoles are reacted, obtain having the cation of formula (I) structure poly- to benzene
Support ethene derivatives；
Wherein, the m1For 3~10；
The m2For 3~10；
The n is 5~10.
According to the present invention, the present invention reacts the compound and N- methylimidazoles of formula (II) structure, obtains tying with formula (I)
The cation poly-phenylene vinylene (ppv) derivative of structure；Wherein, the m in the compound of formula (II) structure1、m2Selection with n is with before
State identical；The solvent of the reaction is preferably the mixed liquor of chloroform and acetonitrile, and the volume ratio of the chloroform and acetonitrile is preferably 1
: (4~6), more preferably 1: 5；The present invention does not have particular/special requirement to the dosage of reaction raw materials, and those skilled in the art can basis
Common knowledge selects suitable dosage；The temperature of the reaction is preferably 80~100 DEG C, more preferably 90~95 DEG C；It is described anti-
The time answered is preferably 60~90 hours, more preferably 72~80 hours.
In the present invention, the compound of formula (II) structure is preferably prepared in accordance with the following methods：
The compound of the compound of formula (III) structure and formula (IV) structure is reacted, obtains the compound of formula (II) structure；
Wherein, the auxiliary agent of the reaction is palladium, trimethylphenyl phosphine oxide and n-butylamine；The solvent of the reaction is preferably toluene；
The temperature of the reaction is 90~110 DEG C, more preferably 100~105 DEG C；The time of the reaction is preferably 36~60 hours,
More preferably 48~50 hours.Amount ratio of the present invention to the compound and the compound of formula (IV) structure of formula (III) structure
There is no particular/special requirement, those skilled in the art can select suitable ratio according to reaction actual conditions.
Wherein, the m1For 3~10；The m2For 3~10.
In the present invention, the compound and three n-butyl vinyl bases of formula (III) structure of formula (IV) structure
Tin hybrid reaction obtains；Wherein, the solvent of the reaction is preferably toluene；The catalyst of the reaction is preferably four triphenylphosphines
Palladium, ferrocene palladium or palladium；The temperature of the reaction is preferably 90~110 DEG C, more preferably 100~105 DEG C；The reaction
Time be preferably 10~30 hours, more preferably 12~24 hours.The present invention also wants to the amount ratio of each raw material without special
Ask, those skilled in the art can select suitable ratio according to reaction actual conditions.
Present invention also offers a kind of fluorescence probe for being used to detect lysosome, the fluorescence probe is of the present invention
Cation poly-phenylene vinylene (ppv) derivative.
Present invention also offers a kind of cell tracker agent, including cation poly-phenylene vinylene (ppv) of the present invention to derive
Thing.
The invention provides a kind of cation poly-phenylene vinylene (ppv) derivative, has structure shown in formula (I), wherein, pass through
Modified quaternary ammonium salt group in the side chain of derivative, i.e. side chain is connected to N- methylimidazoles, makes conjugated polymer positively charged, and then
So that derivative provided by the invention has advantages below relative to other existing cell imaging agent：(1) fluorescence quantum yield
Height, (2) Stokes shift is big, and larger Stokes shift avoids the self-quenching of the PPV in imaging process.Therefore, PPV
Can be as prolonged cell imaging agent, (3) biocompatibility is strong, low toxicity, (4) good light stability；And conjugated polymer can be special
The opposite sex is distributed in lysosome, therefore, can be used as lysosome specificity image probe and long-time cell tracker agent；In addition, this
It is simple to invent the preparation method provided, synthesis yield is high, it is easy to accomplish industrialization.
It is clearly and completely described below in conjunction with the technical scheme of the embodiment of the present invention, it is clear that described implementation
Example only part of the embodiment of the present invention, rather than whole embodiments.It is common based on the embodiment in the present invention, this area
The every other embodiment that technical staff is obtained under the premise of creative work is not made, belong to the model that the present invention protects
Enclose.
Embodiment 1
The synthesis of compound PPV shown in Formulas I, reaction process are as follows：
Specifically synthesis step is：
1st, the synthesis of compound 2
1.16g compounds 1 are dissolved in 25mL degassed toluene solution, under nitrogen atmosphere, add the n-butyl vinyls of 1.34g tri-
Ji Xi and 40mg tetra-triphenylphosphine palladiums.Mixture is stirred 12 hours at 100 DEG C.50mL 2M potassium fluoride aqueous solutions are added to quench
Go out reaction, organic phase is dried with anhydrous magnesium sulfate, be evaporated off silica gel post separation after solvent (eluant, eluent: dichloromethane: petroleum ether=1:
3) 822mg yellow solids are obtained.Characterization of The Products：1H NMR (400MHz, CDCl3)：δ 6.98-7.07 (m, 4H), 5.69-5.75
(d, 2H), 5.24-5.30 (d, 2H), 3.94-3.99 (m, 4H), 3.41-3.45 (m, 1H), 3.18-3.23 (m, 3H), 1.79-
1.89 (m, 8H), 1.48-1.52 (m, 4H) 1.25-1.42 (m, 4H)
2nd, the synthesis of compound 3
688mg compound Isosorbide-5-Nitrae 88mg compounds 2,10mg palladiums, 10mg trimethylphenyls phosphine oxide and 100 μ L normal-butyl
Amine solvent is in 3mL toluene, and under nitrogen atmosphere, 100 DEG C are flowed back 48 hours.Hot solution is poured into 100mL acetone, and centrifugation afterwards is received
Collection precipitation.Precipitation is dried under vacuum, and obtains 50mg red brown solids.Characterization of The Products：1H-NMR (400MHz, CDCl3, ppm)：
δ 7.3-7.4 (m, 2H), 7.0-7.1 (m, 2H), 3.7-4.1 (m, 4H), 3.3-3.4 (m, 2H), 3.1-3.2 (m, 2H), 1.1-
1.5 (m, 8H), 1.7-1.9 (m, 8H)
3rd, compound PPV synthesis
4.6mg PPV solution is dissolved in the mixed liquor (v/v=1/5) of 1.2mL chloroforms and acetonitrile, adds 18mg N- first
Base-imidazoles, solution are heated to 90 DEG C and kept for 72 hours.Remove solvent under vacuum and N- methyl-imidazoles, red residue are molten
Solution is freeze-dried after being dialysed 2 days with pellicle (molecular weight 3500) in 1mL DMSO and obtains 3.3mg red solid products.Production
Thing characterizes：1H NMR (400MHz, DMSO)：δ 7.2-7.7 (br, 10H), 4.0-4.2 (m, 8H), 3.8 (s, 6H), 1.4-1.9
(m, 16H)
Embodiment 2
PPV is added in cultured MCF-7 cells, its cytotoxicity is detected, specifically comprises the following steps：
Every hole inoculum density is 5 × 10 in 96 orifice plates3Individual MCF-7 cells, at 37 DEG C with the PPV (0- of various concentrations
100 μM) cultivate 6 hours.
After removing PPV remaining in culture medium, fresh culture medium is added at 37 DEG C and continues culture 18 hours.
By MTT (5mgmL-1) be added in each hole and continue culture 4 hours.
Supernatant is removed, 100 μ L DMSO are added per hole and remove lysigenous first a ceremonial jade-ladle, used in libation.Flat board is shaken afterwards 2 minutes,
The absorption value in each hole is read under 520nm wavelength illuminations.
The survival ratio (VR) of cell is calculated according to equation below, and draws curves of the VR to PPV concentration：
A is to have the experimental group absorption value after PPV processing, A0To be added without PPV control group absorption value.
By the way that the PPV of MCF-7 cells and various concentrations is mixed in the embodiment, MTT experiment is carried out.As a result as schemed
1, Fig. 1 MCF-7 cell survival rate measurement results handled for the PPV of various concentrations, it can be seen that when PPV concentration is
100 μM, the survival rate of cell has exceeded 70%.The concentration used in cell imaging experiment, the survival rate of cell have exceeded 90%.
Therefore, PPV illustrates fabulous biocompatibility and low cytotoxicity.
Embodiment 3
PPV is added in cultured MCF-7 cells, it is detected in cell with confocal laser scanning microscope, CLSM (CLSM)
In distribution and carry out long-time cell imaging experiment；Specifically it may include following steps：
At 37 DEG C, inoculum density is 5 × 104In culture dish, culture adds individual/mL MCF-7 cells after 12 hours
(30 μM) of PPV is cultivated 6 hours.
PPV remaining in culture medium is removed, is washed three times with PBS, adds 1 μM of Lyso-Tracker dyes afterwards
Material, cultivate 30 minutes at room temperature.
Cell excites PPV under CLSM, with 488nm, is detected after exciting Lyso-Tracker dyestuffs with 559nm.
Control group is without any processing.
For cell long-time image checking, cell is with after PPV and Lyso-Tracker processing, every other day carrying out CLSM
Characterize.
As a result it is as follows：
One) distributions of the compound PPV in cell
In order to probe into distributions of the PPV in cell, commercial lysosome specific dye (Lyso-Tracker) is selected to be used for
With PPV common locations.MCF-7 cells are first cultivated 6 hours in the culture medium containing 30 μM of PPV, are then changed again containing 1 μM of Lyso-
Tracker medium culture 30min.Excited respectively with the light of 488nm and 559nm wavelength and carry out fluorescence imaging.PPV transmittings
Green fluorescence and the red fluorescence of Lyso-Tracker transmittings can preferably overlap yellowing fluorescence.Quantitatively calculate Pearson
Coefficient has reached 0.98, it was demonstrated that PPV has been concentrated mainly in the lysosome of cell, as a result as shown in Fig. 2 Fig. 2 is simultaneously uses
The common focused view of the MCF-7 cells of 30 μM of PPV and 1 μM of Lyso-Tracker processing；It can be seen that PPV can conduct
Lysosome specificity image forming material.
Two) long-time cell imaging is tested
In study tumor cell behavior, can long-time cell imaging serve key effect.Therefore, PPV conducts
Cell imaging agent needs to test the ability of its photostability and long-time imaging, and contrast material chases after for commercial lysosome
Track agent (Lyso-Tracker).After illumination 120 seconds, PPV and Lyso-Tracker is drawn respectively relative to initial fluorescent intensity
Percentage curve, as a result see Fig. 3, Fig. 3 is that PPV and Lyso-Tacker photostability determines curve, it can be seen that
Under the same conditions, PPV remains the 80% of initial strength, and Lyso-Tracker only remains the 40% of initial strength,
Illustrate that PPV has good photostability.
Three) prolonged cell imaging experiment is contrasted PPV and Lyso-Tracker.MCF-7 cells successively containing
Have in PPV and Lyso-Tracker culture medium and cultivate.As indicated at 4, Fig. 4 is simultaneously with 30 μM PPV and 1 μM to Confocal Images
The MCF-7 cell long-period images of Lyso-Tracker processing；It is glimmering that MCF-7 cells illustrate obvious PPV greens after 7 days
Light, and Lyso-Tracker red fluorescence just disappeared after the 3rd day.Between Lyso-Tracker excitation peaks and emission peak
Stokes shift is 19nm, and PPV has reached 102nm.Larger Stokes shift avoids the PPV in imaging process
Self-quenching.Therefore, PPV can be used as prolonged cell imaging agent.
Embodiment 4
Add PPV simultaneously in different rejection conditions and inhibitor to co-culture with MCF-7 cells, carry out cell endocytic suppression
Experiment, probe into cell endocytic PPV mechanism；Specifically it may include following steps：
At 37 DEG C, MCF-7 cells are containing chlorpromazine (10 μ g/mL), dynasore (80 μM), nystatin respectively
Cultivated together in the serum free medium of (5mg/mL) and sucrose (0.45M), and the nothing of any inhibitor is added without at 4 DEG C
Cultivated 1 hour in blood serum medium.
Then PPV is added in the culture medium of above-mentioned cell, final concentration of 30 μM, while with suppression same as described above
Condition processing cell 6 hours.
Finally cell is washed with PBS three times, then characterized using laser confocal microscope CLSM.
Cultivated by making MCF-7 cells under different rejection conditions, including low temperature (4 DEG C), different inhibitor (chlorpromazines
(CPZ), dynasore, nystatin and sucrose).MCF-7 cells are first from different rejection conditions without in hyclone culture medium
Culture 1 hour, it is mixed 6 hours with PPV again afterwards.The fluorogram characterized by laser confocal scanning microscope (CLSM)
As shown in figure 5, Fig. 5 is Confocal Images and fluorescence intensity figure of the MCF-7 cells from 30 μM of PPV under different rejection conditions
Picture, it can be seen that MCF-7 shows seldom fluorescence intensity in low temperature and under conditions of dynasore being present.
MCF-7 cells with PPV and chlorpromazine it is simultaneous under the conditions of cultivate when, show compared to when only being cultivated with MCF-7 cells and PPV
Weak fluorescence intensity is shown.Low temperature inhibits the cell endocytic process that energy mediates, dynasore prevent the formation of vesica and
Chlorpromazine inhibits clathrin-mediated endocytosis process.Therefore, MCF-7 cell internalizings PPV is energy mediation, and clathrin is situated between
Lead and formed what vesica process drove jointly.
To sum up, the present invention has synthesized a species specificity imaging cells lysosome, and available for the poly- of long-time cell imaging
Compound.Concentration in scope of experiment does not have obvious cytotoxicity.It is distributed mainly on after into cell in the lysosome of cell,
Larger Stokes shift is presented, photostability is high, can be present in for a long time in cell.It is a kind of potential to show PPV
Can continue detection cell dynamic behaviour cell imaging agent.
The explanation of above example is only intended to help the method and its core concept for understanding the present invention.It should be pointed out that pair
For those skilled in the art, under the premise without departing from the principles of the invention, the present invention can also be carried out
Some improvement and modification, these are improved and modification is also fallen into the protection domain of the claims in the present invention.
Claims (10)
1. a kind of cation poly-phenylene vinylene (ppv) derivative, there is structure shown in formula (I),
Wherein, the m1For 3~10；
The m2For 3~10；
The n is 5~10.
2. cation poly-phenylene vinylene (ppv) derivative according to claim 1, it is characterised in that the m1For 4,5,6,7,8
Or 9.
3. cation poly-phenylene vinylene (ppv) derivative according to claim 1, it is characterised in that the m2For 4,5,6,7,8
Or 9.
4. a kind of preparation method of cation poly-phenylene vinylene (ppv) derivative, including：
The compound of formula (II) structure and N- methylimidazoles are reacted, obtain cation polyparaphenylene's second with formula (I) structure
Ene derivative；
Wherein, the m1For 3~10；
The m2For 3~10；
The n is 5~10.
5. preparation method according to claim 4, it is characterised in that the compound of formula (II) structure is according to lower section
Method is prepared：
The compound of the compound of formula (III) structure and formula (IV) structure is reacted, obtains the compound of formula (II) structure；
Wherein, the m1For 3~10；
The m2For 3~10.
6. preparation method according to claim 5, it is characterised in that the auxiliary agent of the reaction is palladium, trimethylphenyl
Phosphine oxide and n-butylamine.
7. preparation method according to claim 5, it is characterised in that the formula (III) of formula (IV) structure
The compound of structure and three n-butyl vinyl base tin hybrid reactions obtain.
8. preparation method according to claim 7, it is characterised in that the catalyst of the reaction be tetra-triphenylphosphine palladium,
Ferrocene palladium or palladium.
9. a kind of fluorescence probe for being used to detect lysosome, the fluorescence probe are the sun described in claims 1 to 3 any one
Ion poly-phenylene vinylene (ppv) derivative.
10. a kind of cell tracker agent, including the cation poly-phenylene vinylene (ppv) derivative described in claims 1 to 3 any one.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1673241A (en) * | 2004-03-23 | 2005-09-28 | 中国科学院化学研究所 | Poly(p-phenylene ethylene) and its prepn process and use |
| CN102731405A (en) * | 2012-07-06 | 2012-10-17 | 中国科学院化学研究所 | Photodynamic treatment medicament, medical composition and preparation method thereof |
-
2017
- 2017-09-18 CN CN201710844320.9A patent/CN107573287A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1673241A (en) * | 2004-03-23 | 2005-09-28 | 中国科学院化学研究所 | Poly(p-phenylene ethylene) and its prepn process and use |
| CN102731405A (en) * | 2012-07-06 | 2012-10-17 | 中国科学院化学研究所 | Photodynamic treatment medicament, medical composition and preparation method thereof |
Non-Patent Citations (2)
| Title |
|---|
| ZHUO CHEN ET AL.: "Synthesis of a cationic poly(p-phenylenevinylene) derivative for lysosome-specific and long-term imaging", 《CHINESE CHEMICAL LETTERS》 * |
| 王德平: "钯催化Stille交叉偶联反应研究新进展", 《有机化学》 * |
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