CN106432312A - Mitochondria target fluorescence probe, as well as preparation method and application thereof - Google Patents
Mitochondria target fluorescence probe, as well as preparation method and application thereof Download PDFInfo
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- CN106432312A CN106432312A CN201610848120.6A CN201610848120A CN106432312A CN 106432312 A CN106432312 A CN 106432312A CN 201610848120 A CN201610848120 A CN 201610848120A CN 106432312 A CN106432312 A CN 106432312A
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- CFIIJGHGYCGKSL-QXMHVHEDSA-N CC/C(/CC[B](C1CC1)(F)=C)=C(\C)/C=C Chemical compound CC/C(/CC[B](C1CC1)(F)=C)=C(\C)/C=C CFIIJGHGYCGKSL-QXMHVHEDSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
- C07F5/02—Boron compounds
- C07F5/022—Boron compounds without C-boron linkages
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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
- G01N21/6486—Measuring fluorescence of biological material, e.g. DNA, RNA, cells
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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
- C09K2211/1003—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
- C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms
Abstract
The invention discloses a mitochondria target fluorescence probe, as well as a preparation method and application thereof. The probe has a structure as shown in formula (I). The mitochondria target fluorescence probe can overcome the defects of the traditional commodity probe and has the advantages of high fluorescence quantum yield, excellent water solubility, less influences of environment property and acid-base property on the probe, good imaging effect of mitochondria, low toxicity, high photo-bleaching resistance, and the like, so that the mitochondria target fluorescence probe has excellent application prospects in the fields of long-time living cell mitochondria imaging and bio-labeling.
Description
Technical field
The invention belongs to light technical field of analysis and detection is and in particular to a kind of Mitochondrially targeted fluorescent probe and its preparation side
Method and application.
Background technology
Mitochondrion is important organelle in cell, is the energy plants of cell, and in addition mitochondrion is gone back in cell
There are many important functions, such as control metabolism, calcium ion regulatory and the apoptosis path of cell to control etc., mitochondrial
Dysfunction can lead to multiple diseases, such as parkinson disease, Alzheimer etc., and therefore mitochondrion is imaged to subcellsular level
Diagnosis and treatment have great importance.
Existing frequently-used mitochondrial probe has Rhodamine 123, JC-1, Mitotracker series etc., although they have been made
It is used for mitochondrion for commodity probe to be imaged, but still have that cytotoxicity is big, anti-light bleaching power is weak, be not suitable for long-time line
Many inferior positions such as plastochondria imaging become it is therefore necessary to develop a kind of new mitochondrion fluorescent probe for active somatic cell mitochondrion
Picture.
Content of the invention
In order to overcome many deficiencies of traditional commodities probe, the invention provides a kind of mitochondrion imaging effect is good, toxicity
Strong Mitochondrially targeted fluorescent probe of low, anti-light bleaching power and its preparation method and application.
The technical scheme that the present invention provides is specific as follows：
A kind of fluorescent molecular probe (hereinafter referred to as TEA-BODIPY) with Mitochondrially targeted function, has formula (I) institute
The structure shown：
A kind of method preparing the above-mentioned fluorescent probe with Mitochondrially targeted function, comprises the following steps：
(1) hydroxy benzaldehyde is dissolved in dry DMF, adds Anhydrous potassium carbonate and Isosorbide-5-Nitrae-dibromobutane, room temperature reaction,
Obtain crude product, crude by column chromatography purification, obtain compound 1；Described compound 1 is
(2) compound 1 and 2,4- dimethyl pyrrole are together dissolved in anhydrous methylene chloride, under nitrogen protection, add
Trifluoroacetic acid, as catalyst, is stirred at room temperature 12 hours, is subsequently adding 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone, room temperature bar
Continue stirring 2 hours, stirring adds triethylamine and boron trifluoride diethyl etherate after terminating, and is stirred overnight under part, after reaction terminates, reaction
Liquid uses saturated sodium bicarbonate solution and water washing successively, is then extracted with dichloromethane, then with anhydrous sodium sulfate drying, will slightly produce
Thing adopts column chromatography purification after concentrating, and obtains compound 2；Described compound 2 is
(3) compound 2 is together flowed back 48 hours with triethylamine in dry toluene, through column chromatography after reactant liquor is concentrated
Purification obtains the compound of structure shown in formula (I).
In step (1), the mol ratio of hydroxy benzaldehyde, potassium carbonate and Isosorbide-5-Nitrae-dibromobutane is 1：1.5：2.
In step (2), compound 1,2,4- dimethyl pyrrole and 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone mole
Than for 1：2：1.
In step (3), compound 2 is 1 with the mol ratio of triethylamine：10.
In step (1), the leacheate of column chromatography is 8 for volume ratio：1 normal hexane-acetone mixture；In step (2), post
The leacheate of chromatography is 8 for volume ratio：1 petroleum ether-ethyl acetate mixed liquor；In step (3), the leacheate of column chromatography is body
Long-pending ratio is 4：1 methanol-ethyl acetate mixed liquor.
Application in biomarker field for the above-mentioned fluorescent probe with Mitochondrially targeted function.
The above-mentioned fluorescent probe with Mitochondrially targeted function is used for living cells mitochondria labelling and imaging.
A kind of method using the above-mentioned fluorescent probe detection line grain morphology change with Mitochondrially targeted function, by altogether
The morphology change of focal imaging technology for detection line grain.
The present invention has advantages below and beneficial effect：
(1) present invention preparation Mitochondrially targeted fluorescent probe, have fluorescence quantum yield height (0.80), good water solubility,
Environment polarity and Acidity of Aikalinity are little on probe impact, anti-light bleaching power is strong, the low advantage of cytotoxicity.
(2) synthetic method of the present invention is simple, can carry out large-scale production.
(3) the Mitochondrially targeted fluorescent probe of present invention preparation can be used for bio-imaging, mitochondrial markers, is to give birth to well
Substance markers probe.
Brief description：
Fig. 1 is the synthetic route chart of embodiment 1 middle probe TEA-BODIPY.
Fig. 2 is Absorption and emission spectra figure in acetonitrile for the embodiment 2 middle probe TEA-BODIPY.
Fig. 3 is embodiment 2 middle probe TEA-BODIPY Absorption and emission spectra figure in aqueous.
Fig. 4 is the test chart of embodiment 3 probe TEA-BODIPY fluorescence intensity under condition of different pH.
Fig. 5 is that the MTT cytotoxicity in SGC7901 cell and HeLa cell of embodiment 4 middle probe TEA-BODIPY is real
Test result figure；Wherein, Fig. 5 (a) is SGC7901 cell, and Fig. 5 (b) is HeLa cell.
Fig. 6 is embodiment 5 middle probe TEA-BODIPY and commodity mitochondrial dye Mito-Tracker red to living cells
Mitochondrial common location imaging experiment result figure；Wherein, Fig. 6 (a) is the image to living cells mitochondria for the TEA-BODIPY, figure
6 (b) is the image to living cells mitochondria for the Mito-Tracker red, and Fig. 6 (c) is TEA-BODIPY and Mito-Tracker
Red overlaps to the image of living cells mitochondria, and Fig. 6 (d) is emitting area and the TEA-BODIPY of Mito-Tracker red
Emitting area superposition.
Fig. 7 is the anti-light bleaching experiment result figure of embodiment 6 middle probe TEA-BODIPY, and wherein, 1～16 represents scanning sequence
Number.
Fig. 8 is the anti-light bleaching experiment result figure of commodity probe Mito-Tracker red in embodiment 6, wherein, 1～16
Represent scanning sequence number.
Specific embodiment
Below in conjunction with specific embodiment, technical scheme is described in further detail.Implement the present invention's
Process, condition, reagent, experimental technique etc., in addition to the following content specially referring to, are the universal knowledege of this area and known
General knowledge, the present invention is not particularly limited content.
Embodiment 1：The preparation of the fluorescent organic molecule (TEA-BODIPY) of Mitochondrially targeted function
Hydroxy benzaldehyde (1.22g, 10mmol) and 1,4- dibromobutane (4.30g, 20mmol) are dissolved in 20mL anhydrous
In DMF (DMF), add Anhydrous potassium carbonate (K2CO3) (2.07g, 15mmol) as alkali, room temperature reaction, obtain
To crude product, cross chromatographic column, obtain compound 1, leacheate is the normal hexane-acetone mixing of n-hexane/acetone (v/v)=8/1
Liquid, the structural formula of compound 1 is
Compound 1 (0.512g, 2mmol) and 2,4- dimethyl pyrrole (0.380g, 4mmol) are together dissolved in 200mL do
In dry dichloromethane, under nitrogen protection, with a small amount of trifluoroacetic acid (TFA) as catalyst, after being stirred at room temperature 12 hours
Add 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (2.27g, 20mmol), then continue stirring 2 at ambient temperature
Hour, stirring adds 5mL triethylamine (Et after terminating3) and 8mL boron trifluoride diethyl etherate (BF N3-OEt2), it is stirred overnight, reaction knot
Shu Hou, reactant liquor uses saturated sodium bicarbonate solution and water washing successively, is then extracted with dichloromethane, anhydrous sodium sulfate drying,
Crude product concentrates rear pillar chromatography purification, and leacheate is the petroleum ether-ethyl acetate mixing of petrol ether/ethyl acetate (v/v)=8/1
Liquid, obtains compound 2, and the structural formula of compound 2 is
Compound 2 (0.237g, 0.5mmol) and triethylamine (0.505g, 5mmol) are flowed back in dry toluene 48 little
When, reactant liquor evaporating column chromatography purification obtains target product TEA-BODIPY, and leacheate is methanol/ethyl acetate (v/v)=4/1
Methanol-ethyl acetate mixed liquor；1H NMR (300MHz, DMSO) δ=7.23-7.26 (d, J=8.6Hz, 2H), 7.08-
7.10 (d, J=8.5Hz, 2H), 6.14 (s, 2H), 4.06 (s, 2H), 3.20-3.22 (s, 2H), 3.20 (s, 6H), 2.40 (s,
6H),1.76(s,4H),1.36(s,6H),1.13(s,15H)；ESI:The theoretical value of elementary analysiss:C41H41BBrF2N2OP+(M+)
657.30；The actual numerical value measuring:657.40.
Embodiment 2：Absorption and emission spectra in opposed polarity solution for the Mitochondrially targeted fluorescent probe TEA-BODIPY
Test
The spectrum test concentration that the present invention adopts is 10 μM, and the solvent of test is aqueous solution and acetonitrile solution, TEA-
Absorption and emission spectra in different solvents for the BODIPY is as shown in Figures 2 and 3.The polarity of solvent is to the absorption of probe and transmitting
The change very little of spectrum, its Stokes shift does not almost change it is seen that solvent polarity is to probe TEA-BODIPY's
Impact very little.
Embodiment 3：The test of Mitochondrially targeted fluorescent probe TEA-BODIPY fluorescence intensity under condition of different pH
The spectrum test concentration that the present invention adopts is 10 μM, and the test of TEA-BODIPY fluorescence intensity under the conditions of pH is as schemed
Shown in 4.PH affects very little to the fluorescence intensity of probe, illustrates that this probe can normally use under the conditions of cell physiological pH.
Embodiment 4：The MTT cytotoxicity experiment of Mitochondrially targeted fluorescent probe TEA-BODIPY
Postdigestive cell is seeded on 96 orifice plates, cell-seeding-density is 104Individual/hole, in 37 DEG C, 5%CO2Condition
Lower culture 24 hours, suctions out culture fluid, then continues cultured cells 24 with the culture fluid of the variable concentrations containing TEA-BODIPY
Hour, then every hole adds 10 μ L MTT (5mg/mL), terminates culture after continuing culture 4 hours, suctions out culture fluid, and every hole adds
150 μ L dimethyl sulfoxides, shaking table shake 10 minutes after, tested using multi-function microplate reader, MTT cytotoxicity result as shown in figure 5,
The two kinds of cell HeLa being tested and SGC-7901 cell increase to 200 μm of ol/L in TEA-BODIPY concentration, cultivate 24 hours
After, cell survival rate is all higher than 90% it was demonstrated that this probe has relatively low cytotoxicity, can be used for cell imaging.
Embodiment 5：Mitochondrially targeted fluorescent probe TEA-BODIPY and commodity mitochondrial dye Mito-Tracker red
Common location experiment to living cells mitochondria
The cell that the present invention adopts is HeLa cell, postdigestive cell is seeded in culture dish, in 37 DEG C, 5%CO2
Under the conditions of, culture is allowed to adherent in 24 hours, is washed away with PBS solution and uses TEA-BODIPY (5 μM) after stale cell culture fluid
Cell culture fluid incubated cell 12 hours, then with continuing culture containing Mito-Tracker red (0.5 μM) cell culture fluid
30 minutes, washed with PBS solution and be imaged after three times, common location imaging results are as shown in fig. 6, TEA-BODIPY is swashed by 488nm laser
Send out, Mito-Tracker red by 561nm laser excitation, by the emitting area of commodity mitochondrial dye Mito-Tracker red
It is superimposed with the emitting area of TEA-BODIPY, find that the registration of the two is very high and imaging effect is good it was demonstrated that the line grain of the present invention
Body fluorescent probe TEA-BODIPY can be used for live body mitochondrial markers.
Embodiment 6：Mitochondrially targeted fluorescent probe TEA-BODIPY contrasts the anti-of commodity probe Mito-Tracker red
Photobleaching is tested
The anti-light bleaching experiment of TEA-BODIPY is specific as follows：The cell that experiment adopts is HeLa cell, will be postdigestive
Cell is seeded in culture dish, in 37 DEG C, 5%CO2Under the conditions of, culture is allowed to adherent in 24 hours, is washed away stale with PBS solution
Cell culture fluid after, with the cell culture fluid incubated cell 12 hours of TEA-BODIPY (5 μM), washed after three times with PBS solution
Imaging, then carries out photobleaching experiment with laser confocal microscope, and laser intensity is (65 μ W), and excitation wavelength is (488nm),
Scanning 13.6 seconds every time, experimental result is as shown in Figure 7.
The anti-light bleaching experiment of Mito-Tracker red is specific as follows：The cell that experiment adopts is HeLa cell, will disappear
Cell after change is seeded in culture dish, in 37 DEG C, 5%CO2Under the conditions of, culture is allowed to adherent in 24 hours, is washed away with PBS solution
After stale cell culture fluid, with continuing culture 30 minutes containing Mito-Tracker red (0.5 μM) cell culture fluid, use
PBS solution is imaged after washing three times, then carries out photobleaching experiment with laser confocal microscope, and laser intensity is (65 μ W), swashs
Sending out wavelength is (561nm), scanning 13.6 seconds every time, and experimental result is as shown in Figure 8.
Test result indicate that, the fluorescent probe TEA-BODIPY contrast commodity probe Mito-Tracker shown in the present invention
Red has very excellent anti-light bleaching characteristic, can be used for long-time mitochondrion imaging.
The protection content of the present invention is not limited to above example, under the spirit and scope without departing substantially from inventive concept, this
Skilled person it is conceivable that change and advantage be all included in the present invention, and with appending claims for protect
Shield scope.
Claims (9)
1. a kind of fluorescent molecular probe with Mitochondrially targeted function is it is characterised in that have the structure shown in formula (I)：
2. a kind of method with Mitochondrially targeted function fluorescent probe prepared described in claim 1 is it is characterised in that include
Following steps：
(1) hydroxy benzaldehyde is dissolved in dry DMF, adds Anhydrous potassium carbonate and Isosorbide-5-Nitrae-dibromobutane, room temperature reaction, obtain
Crude product, crude by column chromatography purification, obtain compound 1；Described compound 1 is
(2) compound 1 and 2,4- dimethyl pyrrole are together dissolved in anhydrous methylene chloride, under nitrogen protection, add trifluoro
Acetic acid, as catalyst, is stirred at room temperature 12 hours, is subsequently adding 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone, under room temperature condition
Continue stirring 2 hours, stirring adds triethylamine and boron trifluoride diethyl etherate after terminating, and is stirred overnight, after reaction terminates, reactant liquor according to
Secondary use saturated sodium bicarbonate solution and water washing, are then extracted with dichloromethane, then with anhydrous sodium sulfate drying, crude product is dense
Adopt column chromatography purification after contracting, obtain compound 2；Described compound 2 is
(3) compound 2 is together flowed back 48 hours with triethylamine in dry toluene, through column chromatography purification after reactant liquor is concentrated
Obtain the compound of structure shown in formula (I).
3. method according to claim 2 it is characterised in that：In step (1), hydroxy benzaldehyde, potassium carbonate and Isosorbide-5-Nitrae-
The mol ratio of dibromobutane is 1：1.5：2.
4. method according to claim 2 it is characterised in that：In step (2), compound 1,2,4- dimethyl pyrrole and 2,
The mol ratio of the chloro- 5,6- dicyano -1,4- benzoquinone of 3- bis- is 1：2：1.
5. method according to claim 2 it is characterised in that：In step (3), compound 2 with the mol ratio of triethylamine is
1：10.
6. method according to claim 2 it is characterised in that：In step (1), the leacheate of column chromatography is 8 for volume ratio：
1 normal hexane-acetone mixture；In step (2), the leacheate of column chromatography is 8 for volume ratio：1 petroleum ether-ethyl acetate mixes
Close liquid；In step (3), the leacheate of column chromatography is 4 for volume ratio：1 methanol-ethyl acetate mixed liquor.
7. described in claim 2, there is the application in biomarker field of the fluorescent probe of Mitochondrially targeted function.
8. the fluorescent probe with Mitochondrially targeted function described in claim 1 is used for living cells mitochondria labelling and becomes
Picture.
9. a kind of using the fluorescent probe detection line grain morphology change with Mitochondrially targeted function described in claim 1
Method it is characterised in that：Morphology change by conjugate focus imaging technique detection line grain.
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| CN106928189A (en) * | 2017-03-03 | 2017-07-07 | 济南大学 | A kind of mitochondrial fluorescence probe of identification with larger Stokes displacements |
| CN107722055A (en) * | 2017-10-09 | 2018-02-23 | 天津理工大学 | A kind of Mitochondrially targeted fluorescence probe sensitising agent of low-power white light driving and its synthetic method and application |
| CN109134545A (en) * | 2018-10-09 | 2019-01-04 | 深圳市第二人民医院 | A kind of Mitochondrially targeted fluorescence probe and the preparation method and application thereof |
| CN110790783A (en) * | 2019-11-19 | 2020-02-14 | 湖北科技学院 | Preparation method and application of mitochondrion targeted antitumor drug |
| CN111995619A (en) * | 2020-08-06 | 2020-11-27 | 广州医科大学附属第二医院 | Mitochondrial-targeted thioredoxin reductase fluorescent probe and preparation method and application thereof |
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106928189A (en) * | 2017-03-03 | 2017-07-07 | 济南大学 | A kind of mitochondrial fluorescence probe of identification with larger Stokes displacements |
| CN106928189B (en) * | 2017-03-03 | 2019-04-09 | 济南大学 | A kind of fluorescence probe of the identification mitochondria with larger Stokes displacement |
| CN107722055A (en) * | 2017-10-09 | 2018-02-23 | 天津理工大学 | A kind of Mitochondrially targeted fluorescence probe sensitising agent of low-power white light driving and its synthetic method and application |
| CN107722055B (en) * | 2017-10-09 | 2020-04-03 | 天津理工大学 | Low-power white-light-driven mitochondrion-targeted fluorescent probe photosensitizer and synthesis method and application thereof |
| CN109134545A (en) * | 2018-10-09 | 2019-01-04 | 深圳市第二人民医院 | A kind of Mitochondrially targeted fluorescence probe and the preparation method and application thereof |
| CN109134545B (en) * | 2018-10-09 | 2020-10-30 | 深圳市第二人民医院 | Mitochondrial targeting fluorescent probe and preparation method and application thereof |
| CN110790783A (en) * | 2019-11-19 | 2020-02-14 | 湖北科技学院 | Preparation method and application of mitochondrion targeted antitumor drug |
| CN110790783B (en) * | 2019-11-19 | 2022-05-13 | 湖北科技学院 | Preparation method and application of mitochondrion targeted antitumor drug |
| CN111995619A (en) * | 2020-08-06 | 2020-11-27 | 广州医科大学附属第二医院 | Mitochondrial-targeted thioredoxin reductase fluorescent probe and preparation method and application thereof |
| CN111995619B (en) * | 2020-08-06 | 2022-02-25 | 广州医科大学附属第二医院 | Mitochondrial-targeted thioredoxin reductase fluorescent probe and preparation method and application thereof |
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