CN106986782A - A kind of cell viscosity fluorescence probe and its preparation and application - Google Patents
A kind of cell viscosity fluorescence probe and its preparation and application Download PDFInfo
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/22—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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- 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
- G01N21/6402—Atomic fluorescence; Laser induced fluorescence
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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
- G01N21/645—Specially adapted constructive features of fluorimeters
- G01N21/6456—Spatial resolved fluorescence measurements; Imaging
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- 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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- 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
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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
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Abstract
The present invention synthesizes the fluorescence probe for the tested viscosity that two-photon fluorescence imaging can be utilized with up conversion property by MOLECULE DESIGN；And there is provided a kind of simple and convenient process for preparing of the fluorescence probe：Using cyclopentanone and 4 dimethylamino cinnamaldehydes as raw material, in the presence of a base, reacted in organic solvent, gained precipitation is the fluorescence probe；The fluorescence probe be can be applied to carry out viscosity in solution and cell sensing detection, and the sensing detection is detected comprising fluoroscopic examination, cell imaging.The cell viscosity fluorescence probe of the present invention is that one kind is simple, quickly, sensitive cell viscosity measurements reagent, you can is applied to two-photon fluorescence again for the sub- fluoremetry of leaf-comb and determines, is had broad application prospects in biomolecule detection field.
Description
Technical field
The present invention relates to a kind of method such as fluorescence probe for detecting viscosity and its preparation and utilization spectrum test, cell imaging
Solution and cell viscosity are detected, belongs to organic molecule fluorescence probe field.
Background technology
Intracellular different zones have different viscosity, meanwhile, cell viscosity is a weight of measure of cell viscous-elastic behaviour
Want parameter.When anomalous variation occurs for intracellular viscosity number, embrane-associated protein activity can be influenceed, suppress insulin synthesis etc., led
Cause to produce relevant disease.The method of traditional detection viscosity has：Capillary viscometer, falling ball viscometer, rotation viscometer etc..But
Conventional viscometer easily causes sample pollution, causes larger measurement error, also, can only detect plasma viscosity, it is impossible to realization pair
The detection of viscosity in cell or tissue sample.
Relatively conventional detection method, fluorescent spectrometry has the features such as simple to operate, response is rapid, spatial resolution is high,
The real-time monitoring in cell, tissue is had been carried out, is played an important role in biological field.On the other hand, this patent is adopted
It is two photon imaging technology, there is smaller phototoxicity and Bleachability compared with single photon image technology, biological sample can be reduced
The ambient interferences of product, obtain more preferable three-dimensional imaging effect.The viscosity fluorescence probe reported at present is mostly one-photon excitation, is also reported
The road viscosity fluorescence probe of a part of utilization two-photon excitation.But, utilize the upper conversion imaging nature examination viscosity of dyestuff
Probe, all do not had been reported that in periodical and patent at home and abroad.Therefore, the dyestuff with up conversion property is developed, and is used for
The detection of solution viscosity, can develop the research for promoting intracellular viscosity measurements.
The content of the invention
For current organic molecule fluorescence probe problem present in the detection of cell viscosity, the present invention passes through molecule
Design, synthesizes the fluorescence probe for the tested viscosity that two-photon fluorescence imaging can be utilized with up conversion property.
Present invention also offers a kind of simple and convenient process for preparing of above-mentioned fluorescence probe and in solution and the sensing inspection of cell viscosity
Application in survey.
To achieve the above object, the present invention is adopted the following technical scheme that.
A kind of fluorescence probe for determining cell viscosity, with such as following formula（Ⅰ）Shown structure：
Formula（1）.
A kind of preparation method of above-mentioned fluorescence probe, comprises the following steps：
（1）Using cyclopentanone and 4- dimethylaminos cinnamaldehyde as raw material, in the presence of a base, reacted in organic solvent, it is raw
Into red precipitate, filtering to precipitate, as crude product, and reaction equation is：
；
（2）Crude product recrystallizes such as formula（I）Shown fluorescence probe（BNCPO）Sterling.
In above-mentioned preparation method, the mol ratio of cyclopentanone and 4- dimethylamino cinnamaldehydes is 1:Alkali described in 2 is NaOH, is had
Machine solvent is ethanol；Reaction temperature is room temperature；Reaction is using nitrogen as protection；Reaction end passes through thin-layer chromatography（TLC）Detect 4-
Dimethylamino cinnamaldehyde；Crude product is recrystallized using absolute ethyl alcohol.
Fluorescence probe of the present invention is used for water environment and biosystem determines the application of viscosity.The fluorescence probe is used
In water environment and the sensing detection of the viscosity of biosystem, the sensing detection is detected comprising fluoroscopic examination, cell imaging.Monochromatic light
The fluorimetric excitation wavelength of son is 488nm, and the excitation wavelength that two-photon fluorescence is determined is 860nm, and fluorescence peak is bimodal, peak value
Respectively 540nm and 620nm.
The present invention has advantages below：The synthetic method of fluorescence probe is simple；Using the up conversion property of probe, realize thin
Intracellular two-photon fluorescence imaging；Realize that solution viscosity is detected by up-conversion fluorescence spectral detection, it is easy, quick.Therefore, this hair
Bright is that one kind is simple, quickly, sensitive cell viscosity measurements reagent, and low to cytotoxicity, in biomolecule detection field tool
Have broad application prospects.
Brief description of the drawings
Fig. 1 is probe BNCPO nucleus magnetic hydrogen spectrum figure；
Fig. 2 is single photon fluorescence transmitting collection of illustrative plates of the probe BNCPO in the solution of different viscosity；
Fig. 3 is up-conversion fluorescence transmitting collection of illustrative plates of the probe BNCPO in the solution of different glycerine-water ratio；
Fig. 4 is that HeLa cells stimulate 30 min single photon fluorescence image and two-photon fluorescence by probe BNCPO, coban
Image；
Fig. 5 is that HeLa cells stimulate 60 min single photon fluorescence image and two-photon fluorescence by probe BNCPO, coban
Image；
Fig. 6 is toxotests of the probe BNCPO to HeLa cells.
Embodiment
With reference to embodiment and accompanying drawing, the present invention will be further described, but the present invention is not limited by following embodiments
System.
The fluorescence probe BNCPO of embodiment 1 synthesis.
The mmol of cyclopentanone 1 is dissolved in 15 mL absolute ethyl alcohols, a small amount of solid NaOH is added, at room temperature stirring reaction liquid
It is completely dissolved to NaOH.Then, the mmol of 4- dimethylaminos cinnamaldehyde 2 is added in above-mentioned reactor, under nitrogen atmosphere room
Temperature stirring, TLC detection reaction ends.In course of reaction, red precipitate is gradually separated out, suction filtration obtains crude product.Use absolute ethyl alcohol
Recrystallization once, obtains red probe BNCPO, yield is 81%.1H NMR (400 MHz, CDCl3): δ = 7.41 (d, J
= 8.8 Hz, 4H), 7.23-7.26 (m, 2H), 6.90 (d, J = 15.6 Hz, 2H), 6.81-6.77 (m,
2H), 6.75-6.69 (m, 4H), 3.02 (s, 12H), 2.87 (s, 4H). HRMS: m/z [M+H]+ calcd
for [C27H31N2O]+ 399.2436, found 399.2428。
The fluorescence probe BNCPO fluorescence intensities of embodiment 2 with viscosity change.
Probe BNCPO prepared by Example 1 is dissolved in DMSO, and 1 mM storing solution is made.30 are taken out from storing solution
μ L are added among 5 mL centrifuge tube, use different proportion（0,20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, 95%）'s
Glycerine water solution（pH = 7.2）3 mL are diluted to, its photoluminescent property is measured.Single photon fluorescence spectrum is as shown in Fig. 2 abscissa
For wavelength, ordinate is fluorescence intensity.From Figure 2 it can be seen that with the increase of solution viscosity, fluorescence intensity increase.Up-conversion fluorescence
Spectrum is as shown in figure 3, abscissa is wavelength, and ordinate is fluorescence intensity.As seen from Figure 3, with the increase of solution viscosity, fluorescence
Intensity gradually increases, and fluorescence is stronger at the obtained nm of maximum emission wavelength 620.
The fluorescence probe BNCPO of embodiment 3 determines viscosity to the imaging of HeLa cell fluorescences.
Fluorescence probe BNCPO of the present invention is applied in HeLa cells, fluorescence imaging, concrete operations are carried out to cell viscosity
Step is as follows：
Ctr groups are blank assay, and both at 37 DEG C, the min of HeLa cell incubations 30 takes pictures, as a result as shown in figs. 4a-d.37
Under the conditions of DEG C, HeLa cells are cultivated into 30 min, PBS bufferings in 10.0 μM of probe BNCPO cell culture fluid is added
After solution is washed three times, it is placed under confocal fluorescent microscope and carries out single photon respectively（λex= 488 nm）Fluorescence imaging and double
Photon（λex= 860 nm）Fluorescence imaging, as a result as shown in Fig. 4 e-h.Contrast experiment is to add 10.0 μM of cobans to educate
In the cell culture fluid for there are HeLa cells, 30 min are cultivated at 37 DEG C, then with 10.0 μM of fluorescence probe BNCPO cell culture
After liquid culture 30 min, PBS cushioning liquid are washed three times, it is placed under confocal fluorescent microscope and carries out single photon（λex = 488
nm）Fluorescence imaging and two-photon（λex= 860 nm）Fluorescence imaging, as a result as shown in Fig. 4 i-l.
Repeat the above steps, difference is, each incubation time is 60min, obtains Fig. 5.
As illustrated in figures 4-5, a-d shows HeLa cell itself unstressed configurations；E-h fluorescence represents that probe BNCPO is penetrated into carefully
Intracellular, green fluorescence is all presented under single two-photon excitation；Adding coban stimulates cell, and i-l, which is shown, obtains stronger glimmering
Light, illustrates that cell viscosity increases, the enhancing of probe illumination effect.
Toxicity of the fluorescence probe BNCPO of embodiment 4 to cell.
Utilize MTT experiment detection probe toxicity.Under the conditions of 37 DEG C, Ctr groups are tested to be incubated 24 h HeLa cells
Group is：With the probe BNCPO of various concentrations（5.0, 10.0, 20.0 μM）It is incubated the h of HeLa cells 24.Measure glimmering at 540 nm
Luminous intensity, using fluorescence probe concentration as abscissa, using cell survival rate as ordinate, obtains Fig. 6.As a result show, concentration and probe concentration reaches
During to 20.0 μM, the cell survival rate after 24 hours remains to reach 90%, illustrates that probe BNCPO is substantially non-toxic.
Claims (5)
1. a kind of fluorescence probe for determining cell viscosity, with such as following formula（Ⅰ）Shown structure：
Formula（1）.
2. a kind of preparation method of fluorescence probe as claimed in claim 1, using following steps：
（1）Using cyclopentanone and 4- dimethylaminos cinnamaldehyde as raw material, in the presence of a base, reacted in organic solvent, it is raw
Into red precipitate, filtering to precipitate, as crude product；
（2）Crude product recrystallizes such as formula（I）Shown fluorescence probe（BNCPO）Sterling.
3. preparation method according to claim 2, it is characterised in that mole of cyclopentanone and 4- dimethylamino cinnamaldehydes
Than for 1:2；The alkali is NaOH；Organic solvent is ethanol；Reaction temperature is room temperature；Reaction is using nitrogen as protection；Reaction end
Pass through thin-layer chromatography（TLC）Detect 4- dimethylamino cinnamaldehydes；Crude product is recrystallized using absolute ethyl alcohol.
4. the application that viscosity is determined for water environment and biosystem of fluorescence probe as claimed in claim 1, its feature exists
Be used for the sensing detection of the viscosity of water environment and biosystem in, the fluorescence probe, the sensing detection comprising fluoroscopic examination,
Cell imaging is detected.
5. application according to claim 4, it is characterised in that the excitation wavelength that single photon fluorescence is determined is 488nm, double light
The fluorimetric excitation wavelength of son is 860nm, and fluorescence peak is bimodal, and peak value is respectively 540nm and 620nm.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109438265A (en) * | 2018-12-06 | 2019-03-08 | 四川大学 | A kind of compound and its preparation method and application with brown adipose tissue with affinity |
| CN110172070A (en) * | 2019-06-05 | 2019-08-27 | 商丘师范学院 | A kind of fluorescence probe and its synthetic method and application detecting viscosity and hydrogen peroxide |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004323394A (en) * | 2003-04-23 | 2004-11-18 | Hayashibara Biochem Lab Inc | Cyclopentanone comound |
-
2017
- 2017-03-23 CN CN201710175952.0A patent/CN106986782A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004323394A (en) * | 2003-04-23 | 2004-11-18 | Hayashibara Biochem Lab Inc | Cyclopentanone comound |
Non-Patent Citations (1)
| Title |
|---|
| A. O. DOROSHENKO ET AL.: "Fluorescence Probing of Cell Membranes with Azacrown Substituted Ketocyanine Dyes", 《JOURNAL OF FLUORESCENCE》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109438265A (en) * | 2018-12-06 | 2019-03-08 | 四川大学 | A kind of compound and its preparation method and application with brown adipose tissue with affinity |
| CN109438265B (en) * | 2018-12-06 | 2020-05-08 | 四川大学 | Compound with affinity with brown adipose tissue and preparation method and application thereof |
| CN110172070A (en) * | 2019-06-05 | 2019-08-27 | 商丘师范学院 | A kind of fluorescence probe and its synthetic method and application detecting viscosity and hydrogen peroxide |
| CN110172070B (en) * | 2019-06-05 | 2021-11-02 | 商丘师范学院 | Fluorescent probe for detecting viscosity and hydrogen peroxide as well as synthesis method and application thereof |
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