CN108373447A - A kind of fluorescence probe that distinguishing dead/living cells and its synthetic method and application - Google Patents
A kind of fluorescence probe that distinguishing dead/living cells and its synthetic method and application Download PDFInfo
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- CN108373447A CN108373447A CN201810107191.XA CN201810107191A CN108373447A CN 108373447 A CN108373447 A CN 108373447A CN 201810107191 A CN201810107191 A CN 201810107191A CN 108373447 A CN108373447 A CN 108373447A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D215/14—Radicals substituted by oxygen atoms
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- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- 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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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
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- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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Abstract
The present invention provides the variable fluorescence probe of a kind of target and fluorescence color and its application being imaged in life or death cell is being distinguished, its chemical name is：2 (6 methoxyl group, 6 naphthalene vinyl) N methylquinoline salt compounded of iodine.It is synthesized by following steps：1,2 dimethyl quinoline salt compounded of iodine are synthesized with iodomethane with 2 methylquinolines；Condensation reaction generates product at room temperature using pyrrolidines as catalyst for 1,2 dimethyl quinoline salt compounded of iodine and 6 methoxyl group, 2 naphthaldehyde.The present invention also provides a kind of fluorescence probes to distinguish the application in life or death cell.The probe synthesis of the present invention is simple, can be had great application prospect with two kinds of fluorescence colors, two kinds of dyeing site separator life or death cells.
Description
Technical field
The present invention relates to a kind of fluorescence probes of the variable differentiation life or death cell of dual-target, fluorescence color, and synthesis side
Method and application belong to organic molecule fluorescence probe field.
Background technology
Distinguish detection life or death cell has great significance in biology, medical science and related field.In biology
In, it is the important tool for studying apoptosis process to distinguish detection life or death cell；In field of medicaments, distinguish detection life or death cell,
Statistics cell survival rate is the most direct method for confirming medicine effect and cytotoxicity.Therefore, it is possible to distinguish detection life or death cell
Reagent be life science important research tool, the development of life science can be promoted, have wide commercialization before
Scape.
Up to the present, people depend on the detection of life or death cell the reagent that can distinguish life or death cell.First, pass through
Cellular morphology is directly observed, people are difficult the judgement cell state removed.In addition, when doing statistical research to cell survival rate,
It is also required to that life or death cell can be provided the reagent for distinguishing signal.The reagent for distinguishing life or death cell at present is divided into than colour pattern and fluorescence
Two kinds of type.Representative than colour pattern reagent is the tetrazoliums salt compounds such as MTT and CCK-8.These compounds itself have shortwave and
Faint absorption spectrum can be reduced to long wave, strong absorbed by the mitochondrial membrane potential in living cells is direct or indirect
First a ceremonial jade-ladle, used in libation, therefore by measuring its absorbance, the quantization to viable cell survival rate may be implemented.In contrast, fluorescent type probe
With being more widely applied.Using fluorescent type probe, the observation individual cells shape that we can under the microscope in real time, in situ
State has life science the facilitation of bigger.The spy of differentiation life or death cell reported in commercialization at present and document
Needle is mostly that can only mark the probe of dead cell or living cells, therefore inevitable uneven dyeing can be brought very in experimental implementation
Big interference.Therefore, it to avoid interfering, provides more accurately as a result, it is desirable to which the fluorescence for providing separator life or death cell is visited
Needle, however this kind of probe rarely has report at present.
Invention content
For it is current lack distinguish detection it is dead/live cell fluorescent probe the problem of, the present invention provide a kind of differentiations detection extremely/
The fluorescence probe of living cells, fluorescence color are variable.
It is a further object of the present invention to provide a kind of synthetic methods of above-mentioned fluorescence probe.
Another object of the present invention be to provide a kind of above-mentioned fluorescence probe distinguish detection it is dead/living cells on application.
To achieve the above object, the present invention adopts the following technical scheme that.
A kind of fluorescence probe for distinguishing dead/living cells, its chemical name is 2- (6- methoxyl group -6- naphthalene vinyls)-N- first
Yl-quinoline salt compounded of iodine, abbreviation MNQI, chemical structural formula such as formula（I）It is shown：
Formula (I).
A kind of synthetic method of above-mentioned fluorescence probe, includes the following steps：
（1）2- methylquinolines heat in ethanol with iodomethane to react, isolated 1,2- Dimethyl-quinolins salt compounded of iodine after reaction
（Compound 1）；
（2）1,2- Dimethyl-quinolin salt compounded of iodine is dissolved in 6- methoxy-2-naphthaldehydes in ethyl alcohol, and room temperature is stirred in the presence of pyrrolidines
It mixes, there is solid precipitation, filter to obtain crude product, product is obtained after purification, that is, distinguishes the fluorescence probe of dead/living cells.
The step（1）In, the molar ratio of 2- methylquinolines and iodomethane is 1:1-2.Step（2）In, 1,2- dimethyl-
The molar ratio of quinoline salt compounded of iodine and 6- methoxy-2-naphthaldehydes is 5:4-6；Mole of 1,2- Dimethyl-quinolins salt compounded of iodine and pyrrolidines
Than being 1:1-9.
The step（1）In, reaction temperature is 40-60 DEG C, and the reaction time is 24-48 hours.
The step（2）Middle method of purification is to be recrystallized in ethyl alcohol.
The synthetic route of above-mentioned fluorescence probe is as follows：
。
The application of a kind of target and the variable fluorescence probe of fluorescence color in distinguishing dead/living cells, which is characterized in that single
Multiphoton excitation wavelength is 488 nm, and Dual channel detection, detection wave band is green light band 500-550 nm, near infrared band 663-
738 nm。
The operation principle of above-mentioned fluorescence probe is as follows：
Fluorescence probe of the present invention is cationic salt type compound, and monomer state is yellow-green fluorescence (580 nm),JState of aggregation
For red fluorescence (660 nm).There is living cells Mitochondria higher film potential, probe to be enriched on mitochondria, presentJIt is poly-
Collect state, sends out red fluorescence；After cell death or apoptosis, mitochondrial membrane potential disappears, and probe moves in nucleus, presents single
Figure sends out green fluorescence.To realize the difference of color and dyeing site in life or death cell.
The present invention has the following advantages：
The probe synthesis of the present invention is simple, high income is, it can be achieved that the bi-signal zone sorting to life or death cell is surveyed.
Description of the drawings
Fig. 1 is compound 11H H NMR spectroscopies；
Fig. 2 is compound 113C H NMR spectroscopies；
Fig. 3 is fluorescence probe MNQI's1H H NMR spectroscopies；
Fig. 4 is fluorescence probe MNQI's13C H NMR spectroscopies；
Fig. 5 is the fluorescence imaging picture that probe MNQI colours living cells and dead cell；
Fig. 6 is to be tested in the common location of living cells middle probe MNQI and the dark red probe of mitochondria；And in dead cell middle probe
The common location of MNQI and cell nuclear probe Hoechst33342 is tested；
Fig. 7 is the cytotoxicity test result of probe MNQI.
Specific implementation mode
With reference to embodiment and attached drawing, the present invention will be further described, but the present invention is not limited by following embodiments
System；Compound number in example corresponds to the number in above compound.
The synthesis of 1 fluorescence probe of embodiment.
（1）1,2- Dimethyl-quinolin salt compounded of iodine（Compound 1）Synthesis：
5-10 mL ethyl alcohol is added into round-bottomed flask, the 2- methylquinolines of 1.1-1.4 mL are then added, 0.5-1.2 mL are added
Iodomethane solution, be heated to 40-60 degree react 24-48 hours, reaction system is cooled to room temperature after completion of the reaction, there is solid
It is precipitated, filters and washs available 1,2- Dimethyl-quinolin salt compounded of iodine using ethyl alcohol（Compound 1）, yield 92%.Its nuclear-magnetism is total
The hydrogen that shakes spectrum is as shown in Figure 1.1H NMR (400 MHz, DMSO-d 6) δ 9.12 (d, J = 8.5 Hz, 1H), 8.60 (d,J = 9.0 Hz, 1H), 8.41 (dd, J = 8.2, 1.6 Hz, 1H), 8.24 (ddd, J = 8.8, 7.0, 1.6
Hz, 1H), 8.14 (d, J = 8.5 Hz, 1H), 8.00 (t, J = 7.6 Hz, 1H), 4.45 (s, 3H),
3.09 (s, 3H). 13C NMR (101 MHz, DMSO-d 6 ) δ (ppm): 161.63, 145.85, 139.65,
135.52, 130.77, 129.46, 128.24, 125.62, 119.49, 40.66, 40.45, 40.36, 40.24,
40.03, 39.82, 39.62, 39.41, 23.72。
（2）2- (6- methoxyl group -6- naphthalene vinyls)-N- Methyl-quinoline salt compounded of iodine（MNQI）Synthesis：
Take compound 1（0.6g, 2mmol）It is added in round-bottomed flask, the acetic anhydride of 5mL is added, reaction 8 hours is heated at 80 DEG C；
It boils off after solvent that recrystallization can obtain clean product 0.4g in ethanol, is yellow solid, yield 57%.Its nucleus magnetic hydrogen spectrum and carbon
Spectrum is as shown in Figures 2 and 3.1H NMR (400 MHz, DMSO-d 6) δ (ppm): 9.09 (d, J = 8.9 Hz, 1H),
8.65 (d, J = 9.0 Hz, 1H), 8.59 (d, J = 9.0 Hz, 1H), 8.45 – 8.31 (m, 3H), 8.26
– 8.13 (m, 2H), 8.07 – 7.90 (m, 4H), 7.44 (d, J = 2.5 Hz, 1H), 7.27 (dd, J =
8.9, 2.5 Hz, 1H), 4.60 (s, 3H), 3.93 (s, 3H). 13C NMR (101 MHz, DMSO-d 6 ) δ
(ppm): 159.52, 156.62, 147.77, 144.36, 139.67, 136.47, 135.31, 131.75,
130.97, 130.84, 130.52, 129.39, 128.57, 128.19, 128.11, 125.46, 121.46,
120.03, 119.79, 118.75, 106.91, 56.49, 55.92, 40.62, 40.41, 40.21, 40.00,
39.79, 39.58, 39.37。
The cell imaging of 2 fluorescence probe MNQI of embodiment.
（1）Cell culture, processing and dyeing：
It is 3 × 10 by density5 In the HeLa cell inoculations of a/mL to the 35 mm imaging culture dishes of sterilizing, in CO2Incubator
（Temperature is 37 DEG C, 5 % CO2）Culture 12 hours or more keeps cell adherent.It is obtained with 4% paraformaldehyde processing attached cell 30min
To dead cell sample.The probe DMSO solution that the embodiment 1 that compound concentration is 2.5 mM obtains is mother liquor, to life or death cell culture
The mother liquor being added in ware, it is 5 μM to make its final concentration.Continue to continue to cultivate 1 h respectively under the same conditions, then by cell
Culture solution siphons away, and rinses cell 3 times with culture medium, then carries out cell imaging experiment.
（2）Laser Scanning Confocal Microscope is imaged：
Using 488 nm as excitation wavelength, it is 500-550 nm that green channel, which collects wavelength, and it is 663- that near infrared channels, which collect wavelength,
738 nm obtain fluorescence picture as shown in figure 5, wherein first is classified as the imaging of living cells light field, the imaging of green channel, near infrared channels
Imaging and green channel and near infrared channels are superimposed picture.From figure 5 it can be seen that after MNQI dyeing, green light in living cells
Channel fluorescence is faint, and near infrared channels fluorescence is relatively strong and concentrates in cytoplasm；Green channel fluorescence is relatively strong in dead cell and collects
In in nucleus, near infrared channels fluorescence is weaker.Therefore probe MNQI can be double by fluorescent staining position and fluorescence color
Signal intensity detects life or death cell to distinguish.
3 probe MNQI of embodiment and commercialization probe common location.
In order to further confirm that coloration stations of the probe MNQI in life or death cell, commercial mitochondrial dye line is used respectively
Plastochondria dark red (MTDR) and the nucleus dyestuff (Hoechst33342) of commercialization carry out in living cells and dead cell with MNQI
Common location dyeing imaging.
In the experiment of cell common location, first with 30 min of MTDR staining cells of 200 nM, 5 μM of MNQI dyeing is added
60 min of cell, then siphons away cell culture fluid, rinses cell 3 times with culture medium, carries out cell imaging.It is sharp with 488 nm
Wavelength is sent out, collects the fluorescence of 570-620 nm to acquire the fluorescence signal of MNQI；It is excitation wavelength with 633 nm, collects 663-
The fluorescence of 738 nm acquires the fluorescence signal of MTDR.Fluorescence picture is obtained as shown in Fig. 6 first rows, wherein by it is left-to-right successively
For the imaging of living cells light field, the stacking chart of MTDR fluorescence imagings, MNQI fluorescence imagings and MTDR and MNQI.It is found that living cells
Be red fluorescence after MNQI probe reactions, living cells reacted with MTDR after for green fluorescence；At NIS-Elements images
Reason software calculate the rates of redying of two kinds of dyestuffs is 89%, illustrate that probe dyes mitochondria in living cells.
Dead cell（Living cells handles 30min through 4% paraformaldehyde）In common location experiment, first with 2 μM
30 min of Hoechst33342 staining cells adds 5 μM of 60 min of MNQI staining cells, then inhales cell culture fluid
It walks, rinses cell 3 times with culture medium, carry out cell imaging.It is excitation wavelength with 488 nm, the fluorescence for collecting 500-550 nm comes
Acquire the fluorescence signal of MNQI；It is excitation wavelength with 405 nm, collects the fluorescence of 425-475 nm to acquire Hoechst33342
Fluorescence signal.Fluorescence picture is obtained as shown in Fig. 6 secondary series, wherein by it is left-to-right be followed successively by living cells light field imaging,
The stacking chart of Hoechst33342 fluorescence imagings, MNQI fluorescence imagings and Hoechst33342 and MNQI.It can clearly be seen that
Dead cell is in blue-fluorescence with nucleus after Hoechst33342 probe reactions；Dead cell with after MNQI probe reactions in green it is glimmering
Light, and the staining cell core parts in dead cell MNQI.
Toxicity of the 4 probe MNQI of embodiment to cell.
In the HeLa cell inoculations to the partial hole of 96 orifice plates for being 8000/mL by cell density, remaining hole is then slow with PBS
Fliud flushing is filled, according to following conditions in CO2Incubated cell in incubator：Experimental group is to be incubated with the culture medium containing 5 μM of MNQI
Cell sample after 2 hours, 24 hours and 36 hours, control group are the cell sample for being not added with dyestuff, and blank group buffers for PBS
Liquid sample.It waits after the completion of being incubated, cell culture fluid is changed with fresh culture medium, and be added 10 μ L's in each culture hole
MTT, then incubated cell 4 hours.After the completion of incubation, culture medium is removed, the DMSO of 200 μ L is added per hole, shaking table is used in combination to shake it
10min is to dissolve first a ceremonial jade-ladle, used in libation.Absorbance of each hole at 570nm, the survival rate of cell are tested using microplate reader（Survival
rate）It can be calculated by following formula：
Wherein, AsampleFor experimental group absorbance, AcFor control group absorbance, AbFor the absorbance of blank group.When being incubated with probe
Between be abscissa, make Fig. 7 by ordinate of cell survival rate：Cell survival rate is still up to 90% after dyeing 36 hours, illustrates probe
It is very low to the toxicity of living cells.
Claims (7)
1. a kind of fluorescence probe for distinguishing dead/living cells, its chemical name is 2- (6- methoxyl group -6- naphthalene vinyls)-N- methyl -
Quinoline salt compounded of iodine, chemical structural formula such as formula（I）It is shown：
Formula (I).
2. a kind of synthetic method of fluorescence probe as described in claim 1, which is characterized in that include the following steps：
（1）2- methylquinolines heat in ethanol with iodomethane to react, isolated 1,2- Dimethyl-quinolins salt compounded of iodine after reaction
（Compound 1）；
（2）1,2- Dimethyl-quinolin salt compounded of iodine is dissolved in 6- methoxy-2-naphthaldehydes in ethyl alcohol, and room temperature is stirred in the presence of pyrrolidines
It mixes, there is solid precipitation, filter to obtain crude product, product is obtained after purification, that is, distinguishes the fluorescence probe of dead/living cells；
。
3. synthetic method according to claim 2, which is characterized in that the step（1）In, 2- methylquinolines and iodomethane
Molar ratio be 1:1-2.
4. synthetic method according to claim 2, which is characterized in that the step（1）In, reaction temperature is 40-60 DEG C,
Reaction time is 24-48 hours.
5. synthetic method according to claim 2, which is characterized in that the step（2）In, 1,2- Dimethyl-quinolin iodine
The molar ratio of salt and 6- methoxy-2-naphthaldehydes is 5:4-6；The molar ratio of 1,2- Dimethyl-quinolins salt compounded of iodine and pyrrolidines is 1:
1-9。
6. synthetic method according to claim 2, which is characterized in that the step（2）Middle method of purification is weight in ethyl alcohol
Crystallization.
7. a kind of application of fluorescence probe as described in claim 1 in distinguishing life or death cell.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109574922A (en) * | 2018-12-21 | 2019-04-05 | 济南大学 | A kind of mitochondrial membrane potential fluorescence probe and its synthetic method and application |
| CN109851553A (en) * | 2018-12-25 | 2019-06-07 | 济南大学 | A kind of mitochondria-kernel migration-type film potential fluorescence probe and its synthesis and application |
| CN110790722A (en) * | 2019-11-28 | 2020-02-14 | 济南大学 | Fluorescent probe for distinguishing dead and live cells and preparation method and application thereof |
| CN111217798A (en) * | 2020-02-24 | 2020-06-02 | 山西大学 | Coumarin-quinoline derivative and synthesis method and application thereof |
| CN112225711A (en) * | 2020-11-10 | 2021-01-15 | 山东大学 | PH-sensitive fluorescent probe capable of imaging cell nucleus and mitochondria in two colors simultaneously |
| CN112390790A (en) * | 2020-11-30 | 2021-02-23 | 西北师范大学 | Methyl quinoline-benzopyrylium derivative and preparation method and application thereof |
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| CN109574922A (en) * | 2018-12-21 | 2019-04-05 | 济南大学 | A kind of mitochondrial membrane potential fluorescence probe and its synthetic method and application |
| CN109851553A (en) * | 2018-12-25 | 2019-06-07 | 济南大学 | A kind of mitochondria-kernel migration-type film potential fluorescence probe and its synthesis and application |
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| CN112225711A (en) * | 2020-11-10 | 2021-01-15 | 山东大学 | PH-sensitive fluorescent probe capable of imaging cell nucleus and mitochondria in two colors simultaneously |
| CN112390790A (en) * | 2020-11-30 | 2021-02-23 | 西北师范大学 | Methyl quinoline-benzopyrylium derivative and preparation method and application thereof |
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