CN110028473A - A kind of polar fluorescence probe of detection fat drips - Google Patents
A kind of polar fluorescence probe of detection fat drips Download PDFInfo
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- CN110028473A CN110028473A CN201910437639.9A CN201910437639A CN110028473A CN 110028473 A CN110028473 A CN 110028473A CN 201910437639 A CN201910437639 A CN 201910437639A CN 110028473 A CN110028473 A CN 110028473A
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Abstract
The present invention provides polar fluorescence probe in a kind of detection cell fat drips, chemical structural formula are as follows:.The fluorescence probe can issue stronger fluorescence in the lesser cancer cell fat drips environment of polarity, and weaker fluorescence can be issued in the biggish normal cell fat drips environment of polarity, therefore normal cell and cancer cell can be distinguished, accurately it is positioned at fat drips, sensitivity with higher, good optical stability and to polarity specificly-response, realizes to the polar detection of intracellular fat drips.There can be potential application value in the content for evaluating and studying fat drips in cell, the physiological function for obtaining fat drips in cell to research by Imaging-PAM using probe of the invention.Meanwhile the synthesis step of the probe is simple, purifying is convenient, high income.
Description
Technical field
The invention belongs to small organic molecule fluorescence probe fields, and in particular to a kind of polar fluorescence probe of detection fat drips and
It is applied.
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.Cause
This, the quantity of fat drips can be considered as the potential tumor marker of cancer diagnosis.Further, since in cancer cell lipid-metabolism it is specific
Change, the polarity of fat drips is lower than normal cell in cancer cell.It therefore, will be cancer in conjunction with two indices (quantity and polarity of fat drips)
Disease diagnosis provides more reliable and accurate information.However, as far as we know, being examined by monitoring quantity and the change in polarity of fat drips
The research of disconnected cancer is not yet realized.
Cancer is generally acknowledged one of the incurable disease in the whole world, has a large amount of people to die of cancer every year.Although cancer is important
Disease, but if our timely Clinics and Practices, cancer mortality be can control.It is examined at present by tumor markers
Disconnected cancer has been hot spot, although existing some tumor markers have substantially increased cancer diagnosis rate, due to it
Have the shortcomings that invasive and inconvenient for operation and limit their extensive use.Therefore, develop new tumor marker
Object has a very important significance the Clinics and Practices of cancer.In recent years, fat drips because of its unique structure and performance widely
Cause everybody concern.Fat drips are also related with many important physiological activities other than providing energy for cell.There is report
Road claims, since the metabolic mechanism of fat drips is different, so polarity of the fat drips in cancer cell can be bigger than in normal cell.Cause
This, the polarity of fat drips can be used as an important indicator for distinguishing cancer cell and normal cell.So the polarity for detecting fat drips will
Important tutorial message can be provided for the diagnosis of cancer.
Currently, Imaging-PAM is since it is highly sensitive, Non-invasive detection and highly selective, it has also become detect biological micropolar
The powerful of property environment.Therefore, develop diagnosis of the polarity for cancer that the new polarity probes of one kind detect intracellular fat drips
Have great importance with clinical research.
Summary of the invention
The problem of for currently available technology, the present invention provide and a kind of can detect polar fluorescence in fat drips and visit
Needle.The probe has hypotoxicity, and good optical stability can be accurately positioned fat drips and to polarity specificly-response, utilize this
The probe of invention detects cancer cell by Imaging-PAM.
It is a further object of the present invention to provide a kind of polar applications in detection cell fat drips of above-mentioned fluorescence probe.
To achieve the above object, the present invention adopts the following technical scheme that.
Polar fluorescence probe in a kind of detection cell fat drips, chemical structural formula are as shown in the formula (I):
Formula (I).
The preparation method of above-mentioned fluorescence probe, comprising the following steps:
(1) 3- nitro -7- diethylaminocoumarin (1) and stannic chloride are stirred to react in concentrated hydrochloric acid, and separating-purifying obtains compound
3- amino -7- diethylaminocoumarin (2).
(2) 3- amino -7- diethylaminocoumarin (2) heats in dimethyl sulfoxide with p-fluoronitrobenzene react after, add
Enter cesium fluoride catalysis Reaction Separation and purify to obtain the bis- 4- nitrobenzophenones of compound 3-() amino -7- diethyl amino coumarin (3), i.e.,
Fluorescence probe:
。
In step (1), the mass ratio of the material of the material 3- nitro -7- diethylaminocoumarin (1) and stannic chloride is 1:
3。
In step (1), the separating-purifying step is that sodium hydroxide solution is added into reaction solution to neutralize, until solution is in
Existing neutrality, is precipitated yellow mercury oxide, filters, and filter residue crosses silicagel column using methylene chloride/methanol=20:1v/v as leacheate.
In step (2), the mass ratio of the material of material 3- amino -7- diethylaminocoumarin (2) and p-fluoronitrobenzene
For 1:2.
In step (2), the separating-purifying step is that yellow mercury oxide is precipitated in reaction solution deionized water, is filtered, filter residue
Silicagel column is crossed using methylene chloride/methanol=20:1v/v as leacheate.
A kind of above-mentioned fluorescence probe polar application of fat drips in detection cell.
Mechanism of the invention is as follows:
Since cumarin carbonyl structure is a strong electron-withdrawing group group, diethylin is an electron-donating group, so in probe
In structure, there is the electronics transfer partially occurred from " diethylin " to " carbonyl " part, i.e. cyclic voltammetry method (ICT) is imitated
It answers.Exactly this ICT effect makes probe have " solvation effect ".Within the scope of certain polarity, such as tetrahydrofuran solvent pole
Before property, since " negative solvent effect " accounts for main function so that probe with the polar increase fluorescence intensity of polar solvent gradually
Increase；After further increasing tetrahydrofuran solvent polarity with solvent polarity, since " positive solvent effect " accounts for leading role, make
Fluorescence probe intensity is obtained to reduce with polar variation.However, no matter in normal cell or in cancer cell, fat drips
Polarity all can before tetrahydrofuran polarity, also, in cancer cell fat drips polarity can be less than normal cell in fat drips polarity.
So when probe can issue stronger fluorescence in the lesser cancer cell fat drips environment of polarity, and in the biggish normal cell of polarity
Weaker fluorescence can be issued in fat drips environment.Therefore, normal cell and cancer cell can carry out area by the variation of fluorescence intensity
Point, to realize the diagnosis of diagnosis cancer.
The invention has the following advantages that
Fluorescence probe provided by the invention can distinguish normal cell and cancer cell, accurately be positioned at fat drips, spirit with higher
Sensitivity, good optical stability and to polarity specificly-response are realized to the polar detection of intracellular fat drips.Utilize this
The probe of invention can obtain fat drips in cell to research in the content for evaluating and studying fat drips in cell by Imaging-PAM
Physiological function have potential application value.Meanwhile the synthesis step of the probe is simple, purifying is convenient, high income.
Detailed description of the invention
Fig. 1 is fluorescence probe1H NMR spectra；
Fig. 2 is ultraviolet spectra of the fluorescence probe in opposed polarity solvent.The concentration of probe: 5 μM；
Fig. 3 is fluorescence spectrum of the fluorescence probe in the solvent of opposed polarity.Wherein excitation wavelength is 405 nm；Probe it is dense
Degree: 10 μM；
Fig. 4 is that cell imaging of the fluorescence probe at l cell (3T3) and mouse mastopathy cell (4T-1) is tested.It visits
Needle concentration is 10 μM, and excitation wavelength is 405 nm；
Fig. 5 is imaging of tissue test of the fluorescence probe in mouse tumor tissue.Concentration and probe concentration is 10 μM, excitation wavelength 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.
The synthesis of 1 fluorescence probe of embodiment
(1) 3- nitro -7- diethylaminocoumarin (1) and stannic chloride stir (molar ratio 1:3) in concentrated hydrochloric acid, and reaction 6 is small
When, sodium hydroxide solution is added and neutralizes, until neutrality is presented in solution, yellow mercury oxide is precipitated, filters, purifying obtains compound 3- ammonia
Base -7- diethylaminocoumarin (2):
；
(2) 3- amino -7- diethylaminocoumarin (2) and p-fluoronitrobenzene stir (molar ratio 1:2) in dimethyl sulfoxide,
After reaction 1 hour, catalyst-cesium fluoride is added, reacts 12 hours, yellow mercury oxide is precipitated with deionized water, Purification by suction filtration obtains
The bis- 4- nitrobenzophenones of compound 3-() amino -7- diethyl amino coumarin, as fluorescence probe:
,
Its1H NMR spectra such as Fig. 1.
Ultraviolet spectra of 2 fluorescence probe of embodiment in opposed polarity solvent
Compound concentration is the mother liquor of the 1 gained fluorescence probe of embodiment of 1 mM as spare, and dimethyl sulfoxide is solvent.It is added 10
μ L probe mother liquor is in the solvent of 2 mL opposed polarities, and final concentration of 5 μM of probe.Solvent arranged from small to large according to polarity according to
It is secondary are as follows: toluene, Isosorbide-5-Nitrae-dioxane, tetrahydrofuran, methylene chloride, dimethyl sulfoxide, methanol, deionized water.Detect each solvent
Ultra-violet absorption spectrum, as shown in Figure 2.As shown in Figure 2, which has different absorption maximums in the solvent of opposed polarity
Wavelength.
Fluorescence spectrum of 3 fluorescence probe of embodiment in the solvent of opposed polarity
The mother liquor of fluorescence probe obtained by the embodiment that 10 mL concentration are 1 mM is prepared as spare, dimethyl sulfoxide is solvent.Add
20 μ L probe mother liquors are in the solvent of 2 mL opposed polarities, and final concentration of 10 μM of probe.Solvent is arranged from small to large according to polarity
Leie are as follows: toluene, Isosorbide-5-Nitrae-dioxane, tetrahydrofuran, methylene chloride, dimethyl sulfoxide, methanol, deionized water.Excitation wave
A length of 415nm detects fluorescence probe fluorescence spectrum in each solvent, as shown in Figure 3.With polar increase, the probe is most
Apparent red shift trend is presented in big launch wavelength.
Cell imaging of 4 fluorescence probe of embodiment in 3T3 and 4T-1 is tested
The mother liquor of fluorescence probe obtained by the embodiment that 10 mL concentration are 1 mM is prepared as spare, dimethyl sulfoxide is solvent.It will
The probe mother liquor of 10 μ L is separately added into 3T3 cell (l cell) and 4T-1(mouse mastopathy cell) it incubates in 0 cell
Educate 20 min.After cultivating, 3T3 and 4T-1 cell fluorescence photograph is shot respectively under monochromatic light subpattern with fluorescence microscope
Piece, excitation wavelength are 405 nm, as described in Figure 4.As shown in Figure 4, fluorescence probe carries out in mouse mastopathy cell (4T-1)
The fluorescence of green is launched in aggregation, and in l cell (3T3), fluorescence probe does not issue fluorescence.
Common location of 5 fluorescence probe of embodiment in mouse mammary tumor cells with commercialization fat drips dyestuff
Compound concentration is that the test mother liquor that the dimethyl Asia of fluorescence probe obtained by the embodiment of 1 mM is soughed is stand-by；Compound concentration is 20
μM commercially available Nile red fat drips dedicated targeting agent the test mother liquor soughed of dimethyl Asia it is stand-by.By the mouse cream of suitable density
Adenoncus oncocyte is inoculated into the imaging culture dish of sterilizing, is cultivated in the incubator, after cell is adherent, while respectively to three groups
Fat drips are added in cell and are commercialized dyestuff Nile red, fluorescence probe, Nile red+probe, make 10 μ of fluorescence probe ultimate density
M, Nile red ultimate density are 5 μM.After half an hour, culture medium is discarded, it is secondary with PBS buffer solution (pH=7.2) flushing cell (3), with
After carry out fluorescence imaging, green excitation wavelength is 405 nm, and red excitation wavelength is 561 nm.With fluorescence microscope in monochromatic light
The fluorescence photo that Nile red for shooting, fluorescence probe and the common incubated cell of Nile red+probe are distinguished under subpattern, such as Fig. 5 institute
Show.As shown in Figure 5, fluorescence probe launches green fluorescence in cell；Nile red launches red fluorescence in cell；And
Nile red+probe launches overlapping yellow fluorescence in cell.The experimental results showed that the probe can be accurately positioned into the cell
Fat drips.
Claims (6)
1. polar fluorescence probe in a kind of detection cell fat drips, chemical structural formula are as shown in the formula (I):
Formula (I).
2. a kind of preparation method of fluorescence probe as described in claim 1, which comprises the following steps:
(1) 3- nitro -7- diethylaminocoumarin and stannic chloride are stirred to react in concentrated hydrochloric acid, and separating-purifying obtains compound 3- ammonia
Base -7- diethylaminocoumarin:
；
(2) 3- amino -7- diethylaminocoumarin heats in dimethyl sulfoxide with p-fluoronitrobenzene react after, be added cesium fluoride
Catalysis Reaction Separation purifies to obtain the bis- 4- nitrobenzophenones of compound 3-() amino -7- diethyl amino coumarin, i.e. fluorescence probe:
。
3. preparation method according to claim 2, which is characterized in that in step (1), the material 3- nitro -7- diethyl
The mass ratio of the material of amido cumarin and stannic chloride is 1:3；In step (2), the material 3- amino -7- diethylaminocoumarin
The mass ratio of the material with p-fluoronitrobenzene is 1:2.
4. preparation method according to claim 2, which is characterized in that in step (1), the separating-purifying step is to anti-
Answer and sodium hydroxide solution is added in liquid neutralizes, until solution presents neutral, yellow mercury oxide is precipitated, filters, filter residue with methylene chloride/
Methanol=20:1v/v is that leacheate crosses silicagel column.
5. preparation method according to claim 2, which is characterized in that in step (2), the separating-purifying step is will be anti-
It answers liquid deionized water that yellow mercury oxide is precipitated, filters, filter residue crosses silicagel column using methylene chloride/methanol=20:1v/v as leacheate.
6. a kind of polar application of fat drips in detection cell of fluorescence probe as described in claim 1.
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| CN201910437639.9A CN110028473B (en) | 2019-05-24 | 2019-05-24 | Fluorescent probe for detecting polarity of lipid droplets |
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| CN201910437639.9A CN110028473B (en) | 2019-05-24 | 2019-05-24 | Fluorescent probe for detecting polarity of lipid droplets |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110981842A (en) * | 2019-11-15 | 2020-04-10 | 郑州大学 | Fluorescent probe for distinguishing normal cells and cancer cells and specifically detecting lipid droplets and application |
| CN113603654A (en) * | 2021-07-14 | 2021-11-05 | 江苏大学 | Difunctional fluorescent probe for detecting lipid droplets and/or protein aggregates and preparation method and application thereof |
| CN113773292A (en) * | 2021-09-29 | 2021-12-10 | 皖南医学院 | Washing-free AIEgen fluorescent probe targeting lipid droplets and preparation method and application thereof |
| CN113845519A (en) * | 2021-09-18 | 2021-12-28 | 山西大学 | Microenvironment sensitive type fluorescent probe and preparation method and application thereof |
| CN114702507A (en) * | 2022-05-23 | 2022-07-05 | 济南大学 | Fluorescent probe for detecting lipid droplets and endoplasmic reticulum |
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| CN108440475A (en) * | 2018-03-16 | 2018-08-24 | 济南大学 | A kind of Ratiometric fluorescent probe and its preparation method and application for distinguishing opposed polarity fat drips |
| CN108822019A (en) * | 2018-08-21 | 2018-11-16 | 济南大学 | Polar fluorescence probe of a kind of detection fat drips and its preparation method and application |
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2019
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| CN108440475A (en) * | 2018-03-16 | 2018-08-24 | 济南大学 | A kind of Ratiometric fluorescent probe and its preparation method and application for distinguishing opposed polarity fat drips |
| CN108822019A (en) * | 2018-08-21 | 2018-11-16 | 济南大学 | Polar fluorescence probe of a kind of detection fat drips and its preparation method and application |
Non-Patent Citations (2)
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| JUNLING YIN 等: "Rational design of a lipid-droplet-polarity based fluorescent probe for potential cancer diagnosis", 《CHEM. COMMUN.》 * |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110981842A (en) * | 2019-11-15 | 2020-04-10 | 郑州大学 | Fluorescent probe for distinguishing normal cells and cancer cells and specifically detecting lipid droplets and application |
| CN110981842B (en) * | 2019-11-15 | 2021-07-02 | 郑州大学 | Fluorescent probe for distinguishing normal cells and cancer cells and specifically detecting lipid droplets and application |
| CN113603654A (en) * | 2021-07-14 | 2021-11-05 | 江苏大学 | Difunctional fluorescent probe for detecting lipid droplets and/or protein aggregates and preparation method and application thereof |
| CN113603654B (en) * | 2021-07-14 | 2022-07-22 | 江苏大学 | Difunctional fluorescent probe for detecting lipid droplets and/or protein aggregates as well as preparation method and application thereof |
| CN113845519A (en) * | 2021-09-18 | 2021-12-28 | 山西大学 | Microenvironment sensitive type fluorescent probe and preparation method and application thereof |
| CN113845519B (en) * | 2021-09-18 | 2022-05-31 | 山西大学 | Microenvironment sensitive type fluorescent probe and preparation method and application thereof |
| CN113773292A (en) * | 2021-09-29 | 2021-12-10 | 皖南医学院 | Washing-free AIEgen fluorescent probe targeting lipid droplets and preparation method and application thereof |
| CN114702507A (en) * | 2022-05-23 | 2022-07-05 | 济南大学 | Fluorescent probe for detecting lipid droplets and endoplasmic reticulum |
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