CN110031436A - A kind of organosilicon fluorescence probe detecting fat drips - Google Patents
A kind of organosilicon fluorescence probe detecting fat drips Download PDFInfo
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Abstract
The present invention provides a kind of organosilicon fluorescence probes for detecting fat drips:.Probe of the invention has AIE effect, by judging that the power of fluorescence can distinguish different cells.There can be potential application value in the physiological function for evaluating and studying cancer cell, the physiological function for obtaining cancer cell to research by Imaging-PAM using probe of the invention.
Description
Technical field
The invention belongs to technical field of analytical chemistry, and in particular to it is a kind of detect fat drips fluorescence probe and its application.
Background technique
Fat drips obtain the concern of numerous researchers due to its special structure and physiological function recently.Fat drips are used as and are rich in
The subcellular organelle of lipid, is widely present in eukaryocyte, is made of the core of neutral lipid, and the neutral lipid is by installation phase
The single layer phosphatide for closing protein surrounds.Other than as energy storage device, fat drips also participate in various physiology courses, including cell is lived
Change, migrates, proliferation, apoptosis etc..More and more evidences show that the exception of fat drips is related with cancer development.It is reported that cancer cell
The quantity of middle fat drips is higher than normal cell, because the big energy that fat drips provide is necessary to cancer cell is proliferated faster.This
Outside, due to the specific change of lipid-metabolism in cancer cell, the polarity of fat drips is lower than normal cell in cancer cell.Therefore, in conjunction with two
A index (quantity and polarity of fat drips) can position cancerous tumor cell.However, being become at present by the quantity and polarity of monitoring fat drips
Change is not yet realized to position the research of cancerous tumor cell.
Inconvenience that there are many methods of traditional detection cancer cell with it is restricted, fluorescence probe is quick and convenient, sensitive because of its
It spends high, detection immediately and responds numerous advantages such as rapid, it is fast-developing again in recent years.These advantages make it in chemistry, biology
The ambits such as medicine suffer from relatively broad application, and especially in field of biomedicine, fluorescence probe be can be not only used for
Analyzed in vitro can be also used for the iconography research of living body.In recent years, the small-molecule fluorescent probe for detecting cancer cell is largely reported
Road.However, many probe poorly water-solubles, sensitivity is low, pH variation is larger to the influential effect of detection, separately there are some spies
Needle bio-toxicity is big, membrane permeability ability is poor, these defects largely affect the application of Small-molecule probe.Therefore it sends out
The probe that sensitive detection cancer cell is stablized in exhibition has a very important significance.
Summary of the invention
For current probe poorly water-soluble, sensitivity is low, pH variation is larger to the influential effect of detection, probe biology poison
Property big, membrane permeability ability difference problem, the present invention provides a kind of organosilicon fluorescence probe of detection fat drips, response speed
Fastly, strong antijamming capability.
It is a further object of the present invention to provide a kind of above-mentioned fluorescence probes in the application for detecting intracellular fat drips.
To achieve the above object, the present invention adopts the following technical scheme that.
A kind of organosilicon fluorescence probe detecting fat drips, abbreviation TR, chemical structural formula are as shown in the formula (I):
Formula (I).
The preparation method of above-mentioned organosilicon fluorescence probe, comprising the following steps:
(1) aminopropyl silicone oil and bromo- 1, the 8- naphthalene anhydride of 4- heating reflux reaction in ethanol, is filtered, filter residue is with body after reaction
Product than be 1:20 methanol: methylene chloride is that leacheate crosses silicagel column, then dry compound 1:
；
(2) under protective atmosphere, compound 1 and 4- boric acid triphenylamine are in toluene in K2CO3In the presence of with four (triphenyl phosphorus) palladiums
It is catalyzed heating reflux reaction, be after reaction the methanol of 1:10 using volume ratio: methylene chloride crosses silicagel column as leacheate, then
Dry organosilicon fluorescence probe:
。
The mass ratio of the aminopropyl silicone oil and the bromo- 1,8- naphthalene anhydride of 4- is 5:1.
The mass ratio of the compound 1 and 4- boric acid triphenylamine is 1:0.8-1.
In step (1) and step (2), reaction temperature is 80 DEG C.
A kind of application of above-mentioned organosilicon fluorescence probe in preparation detection cell fat drips quantity and polar reagent.
Mechanism of the invention is as follows:
Probe TR of the invention has AIE effect, and the poor solubility in fat drips.It can make when fat drips content increases in cell thin
Born of the same parents' polarity reduces, to make the probe TR content in cytoplasm is opposite to improve, fluorescence intensity is caused to increase, and launch wavelength occurs
Blue shift.By judging that the power of fluorescence can distinguish different cells.
The invention has the following advantages that
Fluorescence probe provided by the invention differentiates cancer cell by change in polarity and normal cell, the result and its phenomenon is made a living
Object imaging applications have established theoretical basis, indicate that it has potentially in LASER Excited Fluorescence biomarker field using valence
Value.Correspondingly, can be in evaluating and the physiological function of research cancer cell, to grinding by Imaging-PAM using probe of the invention
Studying carefully the physiological function for obtaining cancer cell has potential application value.
Detailed description of the invention
Fig. 1 is the nuclear magnetic spectrogram of probe；
Fig. 2 is fluorescence spectrum of the probe in the solvent of opposed polarity.Wherein excitation wavelength is 405 nm；The concentration of probe: 10
µM；
Fig. 3 is fluorescence spectrum of the probe in the petroleum ether of different proportion and the mixed solution of tetrahydrofuran.Wherein excitation wavelength
For 405 nm；10 μM of the concentration of probe；
Fig. 4 is that probe is incubated for for 24 hours afterwards to cytotoxicity；
Fig. 5 is that cell imaging of the probe at l cell (3T3) and mouse mastopathy cell (4T-1) is tested.Probe is dense
Degree is 10 μM, and excitation wavelength is 405 nm.
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, compound number correspond to reaction equation in summary of the invention.
The synthesis of 1 fluorescence probe of embodiment
(1) first 2 g aminopropyl silicone oil are dissolved in the ethyl alcohol of 20 mL, then bromo- 1, the 8- naphthalene anhydride of 0.4 g 4- is dissolved in 40 mL's
It in ethyl alcohol, is added in the eggplant type reaction flask of 100 mL jointly, is warming up to 80 DEG C, back flow reaction 8h.After reaction, it filters
To solid, (methanol: dichloro=1:20) is purified by column chromatography, obtains compound 1 after dry；
(2) the compound A of 0.37 g is dissolved in the toluene of 20 mL, then the 4- boric acid triphenylamine of 0.346 g is dissolved in 20 mL
Toluene in, in the common eggplant type reaction flask that 100 mL are added.It is added four (triphenyl phosphorus) palladiums of 0.058 g thereto again, 2
The K of mL2CO3Aqueous solution (2 mol/L).10 h are stirred in nitrogen protection, 80 DEG C of reactions.After reaction, it is mentioned by column chromatography
Pure (methanol: dichloro=1:10) obtains compound TR after dry.Its1H NMR spectra such as Fig. 1.
Fluorescence spectrum of 2 fluorescence probe of embodiment in the solvent of opposed polarity
Preparing 10 mL concentration is the polar high molecular fluorescent probe TR mother liquor of detection of the present invention of 1 mM as spare.Add
Enter 20 μ L probe mother liquors (concentration and probe concentration is 10 μM) in the solvent of 2 mL opposed polarities.Solvent is arranged from small to large according to polarity
Leie are as follows: toluene, dichloro, tetrahydrofuran, Isosorbide-5-Nitrae-dioxane, acetonitrile, DMF, DMSO.Excitation wavelength is 405nm.As a result such as
Shown in Fig. 2: with the increase of solvent polarity red shift gradually occurs for the maximum emission peak of probe TR.
Fluorescence spectrum of 3 fluorescence probe of embodiment in different proportion petroleum ether and tetrahydrofuran
Preparing 10 mL concentration is the polar high molecular fluorescent probe TR mother liquor of detection of the present invention of 1 mM as spare.Point
The petroleum ether and tetrahydrofuran mixed solvent of 2 mL different proportions are not configured, petroleum ether: tetrahydrofuran=0,10%, 20%, 30%,
40%, 50%, 60%, 70%, 80%, 90%, 95%.The mother liquor of 10 μ L is added in 2 mL opposed polarity solvents and tests fluorescence spectrum,
Excitation wavelength is 405 nm, as a result as shown in Figure 3: with the increase of petroleum ether volume content within the volume, fluorescence intensity is gradually
Increase.This is because probe solubility in petroleum ether is very poor, increase the percentage of petroleum ether in a solvent, being equivalent to makes probe
TR is assembled, and intensity increases, and illustrates that probe TR has AIE effect, and blue shift occurs for launch wavelength.
Toxicity of 4 fluorescence probe of embodiment to cell
In the HeLa cell inoculation to the partial hole of 96 orifice plates for being 8000/mL by cell density, remaining hole is then used cell-free
Culture medium filling, and under different conditions in CO2Incubated cell in incubator.Experimental group is the training with the TR containing 1-30 μM
The cell sample after base is incubated for 24 hours is supported, control group is the cell sample that dyestuff is not added, and blank group is cell-free culture
Based specimen.After the completion of being incubated for, cell culture fluid is changed with fresh culture medium, and is 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 in every hole, and shakes it with shaking table
10min is to dissolve first a ceremonial jade-ladle, used in libation.Absorbance of each hole at 440nm is tested using microplate reader, cell survival rate can pass through following public affairs
Formula is calculated:
Wherein, AsampleFor experimental group absorbance, AcFor control group absorbance, AbFor the absorbance of blank group.As shown in figure 4, dye
After color 24 hours, when the concentration of TR probe is 10 μM or less, cell survival rate illustrates that the toxicity of probe is very low up to 90% or more.
Imaging applications of 5 fluorescence probe of embodiment in different cells
With manufacturing probe TR mother liquor, concentration is 1 mM, and 10 μM of probe mother liquor is separately added into 3T3 and 4T-1 cell and is incubated for
20 min.After cultivating, 3T3 and 4T-1 cell fluorescence photo is shot respectively under monochromatic light subpattern with fluorescence microscope,
As a result as shown in Figure 5: probe TR is assembled in mouse mastopathy cell (4T-1), launches the fluorescence of green, and small
In mouse fibroblast cell (3T3), probe TR does not issue fluorescence.Since the quantity of fat drips in 4T-1 cell is higher than normal cell,
And the polarity of fat drips is far below the fat drips in 3T3 cell, so probe TR assembles in 4T-1 cell because AIE effect fluorescence is strong
Degree increases.
Claims (5)
1. a kind of organosilicon fluorescence probe for detecting fat drips, chemical structural formula are as follows:
。
2. a kind of preparation method of organosilicon fluorescence probe as described in claim 1, which comprises the following steps:
(1) aminopropyl silicone oil and bromo- 1, the 8- naphthalene anhydride of 4- heating reflux reaction in ethanol, is filtered, filter residue is with body after reaction
Product than be 1:20 methanol: methylene chloride is that leacheate crosses silicagel column, then dry compound 1:
；
(2) under protective atmosphere, compound 1 and 4- boric acid triphenylamine are in toluene in K2CO3In the presence of urged with four (triphenyl phosphorus) palladiums
Change heating reflux reaction, be after reaction the methanol of 1:10 using volume ratio: methylene chloride crosses silicagel column as leacheate, then does
It is dry to obtain organosilicon fluorescence probe:
。
3. preparation method according to claim 2, which is characterized in that the aminopropyl silicone oil and bromo- 1, the 8- naphthalene anhydride of 4-
Mass ratio is 5:1；The mass ratio of the compound 1 and 4- boric acid triphenylamine is 1:0.8-1.
4. preparation method according to claim 2, which is characterized in that in step (1) and step (2), reaction temperature 80
℃。
5. a kind of organosilicon fluorescence probe as described in claim 1 is in preparation detection cell fat drips quantity and polar reagent
Using.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110372738A (en) * | 2019-07-30 | 2019-10-25 | 济南大学 | A kind of fluorescence probe and its preparation method and application of positioning fat drips detection hydrogen sulfide |
| CN110643355A (en) * | 2019-09-19 | 2020-01-03 | 济南大学 | Fluorescent probe for detecting polarity of endoplasmic reticulum as well as preparation method and application thereof |
| CN111393441A (en) * | 2020-04-28 | 2020-07-10 | 四川大学 | Aggregation-induced lipid droplet targeted staining reagent based on purine skeleton and preparation method and application thereof |
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| CN111393441A (en) * | 2020-04-28 | 2020-07-10 | 四川大学 | Aggregation-induced lipid droplet targeted staining reagent based on purine skeleton and preparation method and application thereof |
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