CN110194766A - A kind of binary channels two-photon fluorescence polarity probes and its preparation method and application - Google Patents
A kind of binary channels two-photon fluorescence polarity probes and its preparation method and application Download PDFInfo
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Abstract
The invention discloses a kind of binary channels two-photon fluorescence polarity probes and its preparation method and application, and wherein the structure of binary channels two-photon fluorescence polarity probes is as follows:Two-photon fluorescence polarity probes molecule of the present invention shows specificity response in the system coexisted with other disturbing factors, to polarity.Cytotoxicity test shows the probe for cell almost without what toxic side effect, the experiment of two-photon confocal fluorescent micro-imaging shows that the probe is good to HeLa cell permeability, it can be suitable for polar binary channels two-photon fluorescence imaging and quantitative detection in cell mitochondrial with the mitochondria (orientation factor 0.95) in effective position cell.
Description
Technical field
The present invention relates to a kind of binary channels two-photon fluorescence polarity probes and its preparation method and application, to realize binary channels
Polarity in two-photon fluorescence imaging quantitative detection cell mitochondrial has single-minded selectivity, high sensitivity, bio-toxicity low
Advantage.
Background technique
Mitochondria is very important organelle in eukaryocyte, such as generating atriphos (ATP) is physiology course
Energy is provided, therefore it is referred to as the energy source of cell.In addition, it is, for example, macromolecular that mitochondria, which participates in many physiology courses,
Biosynthesis provides energy and maintains intracellular Ca2+Horizontal stable state etc..Mitochondria and polarity, viscosity, the microenvironments parameter such as pH
It is closely related.And mitochondria polarity is particularly important, it can influence mitochondria activity.Wherein, mitochondria dysfunction can be led
Cause a series of disease such as neurodegenerative disease etc..Mitochondria dysfunction will lead to Apoptosis.More importantly
Mitochondria polarity can change when mitochondria dysfunction, therefore can further monitor apoptosis by detecting reversing.
Apoptosis is one of process of programmed death, important role is played the part of in bioprocess, therefore examine
Apoptosis is surveyed to have great importance for biological study.At present the method for detection apoptosis be based on conventional method, such as
Detect the activity etc. of caspase protein.But the cost of these methods is very high, and the period is very long and sensibility is very poor, and they
The very high requirement for not being able to satisfy assessment Apoptosis of cost.So far, for assessing the fluorescence probe analysis side of Apoptosis
Method is still rarely found, and therefore, it is necessary to develop the fluorescence probe haveing excellent performance as early as possible to detect Apoptosis.
In the past decade, fluorescence probe method has been widely used in monitoring bioprocess, this is based primarily upon fluorescence
Probe technique is cheap, uses simple, high sensitivity, fast response time.Currently, very more fluorescence probes has been developed,
But the polar probe of detection mitochondria or considerably less, therefore the mitochondria polarity probes that exploitation is had excellent performance are very urgent
It cuts.
Polarity is to play very important effect in bioprocess.Such as the infiltration of the adjustable organelle film of polarity
Property.In addition, polar anomalous variation has very big contact with certain diseases.The polar main mechanism of current detection is based on ICT
Mechanism, this mechanism have to environment polarity it is more highly sensitive, to be provided during detect polarity accurate as a result, this is right
It is of great significance in bioenvironmental research.Also, polarity has very big change in apoptosis process, therefore can lead to
Polarity is crossed to detect apoptosis, this provides a good thinking for research Apoptosis.
Summary of the invention
The present invention is intended to provide a kind of binary channels two-photon fluorescence polarity probes and its preparation method and application, to be solved
The technical issues of be obtained by MOLECULE DESIGN it is a kind of can be with the knot of the Ratio-type two-photon fluorescence polarity probes of mitochondria positioning
Structure has selectivity specially to realize the change in polarity in binary channels two-photon fluorescence imaging detection apoptosis process mitochondria
One, the advantages of high sensitivity, Dual channel detection, cytotoxicity test shows fluorescence probe of the present invention to cell almost without toxicity
Effect.
Binary channels two-photon fluorescence polarity probes of the present invention, are abbreviated as Mito-PF, and using carbazole as parent, structural formula is such as
Under:
The preparation method of binary channels two-photon fluorescence polarity probes of the present invention, includes the following steps:
Step 1: by the iodo- 9H- carbazole -3- formaldehyde (1.0g, 2.86mmol) of compound 9- ethyl -6-, 4- fluorobenzene acetylene
(0.41g, 3.44mmol), triphenyl phosphorus palladium chloride (9.65mg, 0.014mmol), cuprous iodide (5.24mg,
It 0.027mmol) is added in reactor with triethylamine (2ml), is stirred 12 hours under the conditions of 30 DEG C of anhydrous and oxygen-frees；Mixture is cold
But to room temperature, precipitating is filtered and is concentrated, crude product is obtained；By column chromatography, (petroleum/methylene chloride=4:1 is as elution
Liquid) purification of crude product, obtain intermediate 1,0.80g, yield 82%.
Step 2: by compound 3- benzyl -2- methylbenzothiazole bromide salt (0.28g, 0.9mmol) and intermediate 1
(0.3g, 0.9mmol) is mixed in 50mL dehydrated alcohol, and mixed solution is flowed back under a nitrogen until TLC shows that raw material is anti-
Should after being cooled to room temperature mixture, solvent be removed by Rotary Evaporators completely (about 12 hours)；Obtained crude product is used
The washing of 30mL saturated brine, is then extracted, and evaporate solvent under vacuum with DCM (3 × 50mL), passes through column chromatography (dichloro
Methane/methanol=50:1 is as eluent) purification of crude product, obtain purpose product Mito-PF, 0.35g, yield 62%.
The synthesis process of two-photon fluorescence probe Mito-PF of the present invention is as follows:
The purposes of binary channels two-photon fluorescence polarity probes of the present invention is living in non-treatment or the quantitative detection of diagnostic purpose
It is used when change in polarity in cell Mitochondria as detection reagent.Detection method is as follows:
Two-photon fluorescence probe of the present invention is dissolved in the mother liquor that 2mM is made in DMSO, respectively takes 15 μ L mother liquors in 3mL not homopolarity
Property solvent in, obtain uv atlas of the probe Mito-PF in different solvents.Under the excitation of 360nm wavelength, in 436nm
The fluorescence intensity at place gradually weakens with the polar increase of test system, and fluorescence intensity has almost no change at 589nm.And
Fluorescence intensity (I436nm/I589nm) and Δ f between there are linear relationships, this shows that Mito-PF can be used for the common solution of ratio test
Polarity.In order to further verify probe Mito-PF to polar response characteristic, in water and tetrahydrofuran with different proportion
Within the scope of polarity, absorption and the fluorescence spectrum of Mito-PF are measured.When solvent polarity from containing 10% water (Δ f ≈ 0.2556) according to
It is secondary when increasing to containing 80% water (Δ f ≈ 0.3103), it can only see small variation in absorbing maximum value and survey different solvents
Polar result is consistent.On the contrary, when solution polarity (when Δ f) is reduced to 0.2556 (10% water) from 0.3103 (80% water),
Fluorescence intensity of the Mito-PF at 436nm increases 3.6 times, and red emission is at 589nm almost without response.Above-mentioned knot
Fruit also shows fluorescence intensity I436nm/I589nmThere is good linear dependence with Δ f, this shows Mito-PF to solvent polarity height
Degree is sensitive.In order to probe into probe Mito-PF optical stability in HeLa cell, this is very important experiment, because
In apoptosis process, mitochondrial membrane potential can be destroyed, and can this will affect the positioning performance of probe, real-time to be related to
Monitor apoptosis process.The article having been reported points out that 3- chlorobenzene hydrazone (CCCP) is film potential disrupting agent, can be with failure line grain
Body film potential.CCCP is added experiments have shown that probe Mito-PF is positioned not against membrane potential.In addition, utilizing probe Mito-PF
Test Etoposide (etoposide) induction HeLa apoptosis process, with going deep into for Apoptosis, intracellular line grain
Body polarity can be gradually reduced.
Two-photon fluorescence polarity probes molecule of the present invention is shown in the system coexisted with other disturbing factors to polarity
Specificity response.Cytotoxicity test shows the probe for cell almost without what toxic side effect, two-photon copolymerization coke
Fluorescent microscopic imaging experiment shows that the probe is good to HeLa cell permeability, can be with the mitochondria (positioning in effective position cell
Coefficient is respectively 0.95), to be suitable for polar binary channels two-photon fluorescence imaging and quantitative detection in cell mitochondrial, and can be with
By detecting mitochondria change in polarity real-time monitoring Apoptosis.
Detailed description of the invention
Fig. 1 is 10 μM of probes (a) uv absorption spectra in opposed polarity organic solvent；(b) fluorescence emission spectrum
Figure；(c) fluorescence intensity (I436nm/I589nm) and Δ f between linear relationship chart.
Fig. 2 be 10 μM of probes in different volumes than water/tetrahydrofuran in the mixed solvent (a) uv absorption spectra；(b)
Fluorescence emission spectrogram of compound；(c) fluorescence intensity (I436nm/I589nm) and Δ f between linear relationship chart.
Fig. 3 is fluorescent emission figure of 10 μM of probes in the methanol of tetrahydrofuran and different viscositys/glycerol mixed system.
Fig. 4 is 10 μM of probes in water/tetrahydrofuran different proportion pH stability diagram.
Fig. 5 is that 0.1mM probe is cut in different volumes two-photon absorption effectively than water/tetrahydrofuran in the mixed solvent (a)
Face figure；(b) opposite two-photon fluorescence intensity (Iout) and input power (Iin) logarithmic relationship figure.
Fig. 6 is the HeLa cell survival rate under the action of probe molecule of various concentration (0 μM, 10 μM, 20 μM, 30 μM)
Figure.
Fig. 7 be 10 μM of probes and 1 μM of Mitotracker green (MTG) and meanwhile altogether dye HeLa cell mitochondrial positioning test
Demonstrate,prove confocal fluorescent image.
Fig. 8 is to be added and two groups of experiments of people CCCP are not added, and probes into the optical stability of probe Mito-PF.
The HeLa Apoptosis confocal fluorescent that Fig. 9, which is 10 μM of probes, to be induced in 50 μM of Etoposides (etoposide) at
As figure.
Specific embodiment
Below by embodiment, the present invention will be further described.
Embodiment 1: the synthesis of fluorescent probe molecule Mito-PF
By compound 3- benzyl -2- methylbenzothiazole bromide salt (0.28g, 0.9mmol) and compound 1 (0.3g,
It 0.9mmol) is mixed in 50mL dehydrated alcohol, and mixed solution is flowed back under a nitrogen until TLC shows raw material fully reacting
(about 12 hours), after mixture is cooled to room temperature, remove solvent by Rotary Evaporators；Obtained crude product 30mL is satisfied
It with salt water washing, is then extracted with DCM (3 × 50mL), and evaporates solvent under vacuum, pass through column chromatography (methylene chloride/first
Alcohol=50:1 is as eluent) purification of crude product, obtain purpose product Mito-PF, 0.35g, yield 62%.
1H NMR (400MHz, DMSO) δ 8.95 (d, J=7.1Hz, 1H), 8.51 (d, J=15.4Hz, 1H), 8.44 (s,
1H), 8.40-8.36 (m, 1H), 8.18 (m, J=14.4,10.1Hz, 2H), 8.12-8.09 (m, 1H), 7.84-7.71 (m,
5H), 7.66-7.60 (m, 2H), 7.38 (t, J=13.9,7.1Hz, 5H), 7.29 (t, J=8.9Hz, 2H), 6.26 (s, 2H),
4.55-4.50 (m, 2H), 1.36 (t, J=6.8Hz, 3H)13C NMR(150MHz,DMSO)δ173.37,152.05,143.28,
141.69,140.58,134.43,134.00,133.94,130.50,129.93,129.68,129.41,129.03,128.71,
128.33,127.50,126.20,124.97,124.46,123.03,122.92,117.23,116.61,116.46,114.16,
111.21,111.07,110.54,90.50,87.55,51.72,38.18,14.36.
Embodiment 2: the spectrum test of fluorescent probe molecule
Fluorescence probe Mito-PF of the present invention is dissolved in the mother liquor that 2mM is made in DMSO, respectively takes 15 μ L mother liquors in 3mL difference
In polar solvent, uv atlas (Fig. 1 a) of the probe Mito-PF in different solvents is obtained.The increase of adjoint solvent polarity,
Value of its fluorescence intensity at 436nm is gradually reduced, and fluorescence intensity has almost no change at 589nm, is rung to provide ratio
Answer (Fig. 1 b).And fluorescence intensity (I436nm/I589nm) and Δ f between there are linear relationship (Fig. 1 c), this shows that Mito-PF can
Polarity for the common solution of Dual channel detection.In order to further prove the polar response characteristic of probe Mito-PF, at 25 DEG C
Within the scope of the water and tetrahydrofuran polarity with different proportion, absorption and the fluorescence spectrum (Fig. 2 a, 2b) of Mito-PF are measured.
When (when Δ f) is reduced to 0.2556 (10% water) from 0.3103 (80% water), Mito-PF is glimmering at 436nm for the polarity of solution
Luminous intensity increases 3.6 times, and red emission is at 589nm almost without response.The above results also show fluorescence intensity I436nm/
I589nmThere is good linear dependence (Fig. 2 c) with Δ f, this shows that Mito-PF is highly sensitive to solvent polarity.According to document report
Road, THF and methanol have almost the same viscosity (0.53cP is to 0.60cP) but polarity is different (0.21 pair 0.31).Mito-PF
Fluorescence intensity at 436nm shows huge difference, and the red emission at 589nm only shows that variation is little.With
Viscosity from the fluorescence intensity that 0.60cP increases at about 100cP, 436nm and 589nm have almost no change (Fig. 3) illustrate probe
Mito-PF is insensitive to viscosity change.In order to exclude the influence of pH, its pH stability is tested, in water/tetrahydrofuran difference system
In, pH value within the scope of 6-9, Mito-PF florescent intensity value change less (Fig. 4), this experimental results showed that pH value to spy
The influence of needle Mito-PF is smaller, and probe Mito-PF is insensitive to the variation of pH.Result above proves that probe Mito-PF can be special
Opposite sex detection polarity is not by the interference of external environment.
Embodiment 3: the two-photon performance test of fluorescent probe molecule
In different water and tetrahydrofuran in the mixed solvent, (content of tetrahydrofuran is respectively 90% to Mito-PF, 50% He
20%), effective two photon absorption cross section is maximum in 720nm appearance and with the reduction of content of tetrahydrofuran, gradually drops from 87GM
To 41GM (Fig. 5 a).It observed two-photon fluorescence excitation intensity of the Mito-PF in different solvents and input power (300-
800mw) the relationship (Fig. 5 b) of Cheng Pingfang.Prove Mito-PF with the ability in intracellular polar two-photon confocal fluorescent at
Picture.
Embodiment 4: cytotoxicity test
We have carried out cytotoxicity reality with MTT (5- dimethylthiazole -2- base -2,5- diphenyltetrazolium bromide) method
It tests.Various concentration (0 μM, 10.0 μM, 20.0 μM, 30.0 μM) is added in HeLa cell living in Mito-PF, tests after 24 hours,
As a result as shown in fig. 6, showing the bio-toxicity very little of Mito-PF above, biologic applications can be carried out.
Embodiment 5: cellular localization test
In order to study the mitochondria positioning performance of Mito-PF, this for research mitochondria polarity be it is very necessary, we
Commercial dyes Mitotracker green (MTG) used herein and Mito-PF carry out common location research in HeLa cell.
The result shows that red channel (the λ of Mito-PFem=560-600nm, λex=720nm) and MTG (λem=500-540nm, λex=
Fluorescent image overlapping 488nm) is good, and the Pearson common location coefficient of Mito-PF and MTG is calculated as 0.95 (Fig. 7).
These results indicate that Mito-PF can be positioned at well in the mitochondria of living cells.
Embodiment 6:Mito-PF stability experiment in mitochondria
In order to probe into probe Mito-PF optical stability in HeLa cell, this is very important experiment, because
In apoptosis process, mitochondrial membrane potential can be destroyed, and can this will affect the positioning performance of probe, real-time to be related to
Monitor apoptosis process.The article having been reported points out that 3- chlorobenzene hydrazone (CCCP) is film potential disrupting agent, can be with failure line grain
Body film potential.CCCP is added in one group of HeLa cell, another group is added without CCCP (Fig. 8).Fluorescence imaging is carried out after 30 minutes.
It is added and is added without CCCP, green and red channel do not change in fluorescence imaging, and mitochondria green quotient dye and probe
Red overlapping is very good, it was demonstrated that probe Mito-PF is positioned not against membrane potential.
Embodiment 7: cell mitochondrial body apoptosis confocal fluorescent imaging
Etoposide (etoposide) can cause Apoptosis, be a kind of generally acknowledged Apoptosis reagent.From existing
From the point of view of document report, Apoptosis can cause the variation of intracellular mitochondrial microenvironment, such as: polarity.Due to Apoptosis mistake
Journey Mitochondria polarity can change, therefore can detecte polarity fluctuation to monitor apoptosis.Therefore, we have done following some
It tests (Fig. 9).Mito-PF (10 μM, 0.5 hour) is entered into intracellular incubation.Later by (50 μM) addition cells of etoposide
Interior, the time was imaged every 10 minutes (A-E).By imaging it can be found that in blue channel (λem=420-460nm) in
Fluorescence intensity gradually increases.And in red channel (λem=560-600nm) in fluorescence intensity kept stable, this and external survey
The fluorescence data of examination is consistent.By the analysis of above data, we can clearly be had found, with addition Etoposide
(etoposide) time increases, i.e., apoptosis is deeper at this moment the polarity of intracellular mitochondrial is gradually reduced that (blue channel is glimmering
Light enhancing, red channel fluorescence are constant).This illustrates that Apoptosis can cause intracellular mitochondrial polarity to reduce.These data card
It is bright we Apoptosis is monitored by intracellular mitochondrial change in polarity is feasible.This is provided for monitoring Apoptosis later
The application that one good method is also later fluorescence probe in terms of biology provides a good thinking.
Claims (5)
1. a kind of binary channels two-photon fluorescence polarity probes, it is characterised in that its structural formula are as follows:
2. a kind of preparation method of binary channels two-photon fluorescence polarity probes described in claim 1, it is characterised in that including such as
Lower step:
Step 1: by iodo- 9H- carbazole -3- formaldehyde 1.0g, 4- the fluorobenzene acetylene 0.41g of compound 9- ethyl -6-, triphenyl phosphorus dichloro
Change palladium 9.65mg, cuprous iodide 5.24mg and triethylamine 2ml to be added in reactor, it is small that 12 are stirred under the conditions of 30 DEG C of anhydrous and oxygen-frees
When；Mixture is cooled to room temperature, precipitating is filtered and is concentrated, crude product is obtained；By column chromatography eluting crude product, obtain
Intermediate 1；
Step 2: by compound 3- benzyl -2- methylbenzothiazole bromide salt 0.28g and 1 0.3g of intermediate in dehydrated alcohol
Middle mixing, and mixed solution is flowed back under a nitrogen up to TLC shows raw material fully reacting, after mixture is cooled to room temperature,
Solvent is removed by Rotary Evaporators；Obtained crude product is washed with saturated brine, is then extracted with DCM, and under vacuum
It evaporates solvent and purpose product Mito-PF is obtained by column chromatography eluting crude product.
3. preparation method according to claim 2, it is characterised in that:
In step 1, eluent when by column chromatography eluting crude product is petroleum: methylene chloride=4:1, v/v.
4. preparation method according to claim 2, it is characterised in that:
In step 2, eluent when by column chromatography eluting crude product is methylene chloride: methanol=50:1, v/v.
5. a kind of purposes of binary channels two-photon fluorescence polarity probes described in claim 1, it is characterised in that:
Make when being the change in polarity in the quantitative detection living cells Mitochondria of non-treatment or diagnostic purpose as detection reagent
With.
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110724524A (en) * | 2019-12-02 | 2020-01-24 | 济南大学 | Fluorescent probe for detecting polarity in cells and preparation method and application thereof |
| CN110878050A (en) * | 2019-12-26 | 2020-03-13 | 安徽大学 | Multifunctional biological probe for two-photon photodynamic therapy and preparation method and application thereof |
| CN111253935A (en) * | 2019-12-24 | 2020-06-09 | 安徽大学 | Two-photon fluorescent probe for detecting polarity and viscosity through two channels and preparation method and application thereof |
| CN111925316A (en) * | 2020-08-19 | 2020-11-13 | 安徽大学 | Two-photon fluorescence polarity probe based on 4-fluorophenylethynyl and preparation method and application thereof |
| CN111995617A (en) * | 2020-09-21 | 2020-11-27 | 安徽大学 | Homocysteine fluorescent probe and preparation method and application thereof |
| CN113429335A (en) * | 2021-06-25 | 2021-09-24 | 安徽大学 | Lysosome targeted dual-response two-photon fluorescence probe and preparation method and application thereof |
| CN113444071A (en) * | 2021-06-25 | 2021-09-28 | 安徽大学 | Cell membrane targeted singlet oxygen generator and preparation method and application thereof |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102757659A (en) * | 2012-07-24 | 2012-10-31 | 大连理工大学 | Carbazole hemicyanine fluorescent dye and application thereof |
| CN104744453A (en) * | 2014-12-05 | 2015-07-01 | 大连理工大学 | Hemicyanine compound for detecting polarity of mitochondria |
| WO2016025382A2 (en) * | 2014-08-09 | 2016-02-18 | Baylor College Of Medicine | Probes for quantitative imaging of thiols in various environments |
| CN105733563A (en) * | 2016-03-31 | 2016-07-06 | 安徽大学 | Two-photon lysosome polar probe based on coumarin and preparing method and application thereof |
| CN108484590A (en) * | 2018-05-18 | 2018-09-04 | 安徽大学 | A kind of two-photon viscosity fluorescence probe and its preparation method and application based on carbazole |
-
2019
- 2019-07-04 CN CN201910597479.4A patent/CN110194766B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102757659A (en) * | 2012-07-24 | 2012-10-31 | 大连理工大学 | Carbazole hemicyanine fluorescent dye and application thereof |
| WO2016025382A2 (en) * | 2014-08-09 | 2016-02-18 | Baylor College Of Medicine | Probes for quantitative imaging of thiols in various environments |
| CN104744453A (en) * | 2014-12-05 | 2015-07-01 | 大连理工大学 | Hemicyanine compound for detecting polarity of mitochondria |
| CN105733563A (en) * | 2016-03-31 | 2016-07-06 | 安徽大学 | Two-photon lysosome polar probe based on coumarin and preparing method and application thereof |
| CN108484590A (en) * | 2018-05-18 | 2018-09-04 | 安徽大学 | A kind of two-photon viscosity fluorescence probe and its preparation method and application based on carbazole |
Non-Patent Citations (4)
| Title |
|---|
| ANETA SLODEK，等: "Phenothiazine derivatives - synthesis, characterization, and theoretical studies with an emphasis on the solvatochromic properties", 《JOURNAL OF MOLECULAR LIQUIDS》 * |
| JINWU FENG，等: "Naphthalene-based fluorophores: Synthesis characterization, and photophysical properties", 《JOURNAL OF LUMINESCENCE》 * |
| NA JIANG，等: "Ratiometric Fluorescence Imaging of Cellular Polarity: Decrease in Mitochondrial Polarity in Cancer Cells.", 《ANGEWANDTE CHEMIE INTERNATIONAL EDITION》 * |
| 姜娜，等: "线粒体荧光探针最新研究进展", 《化工学报》 * |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110724524B (en) * | 2019-12-02 | 2021-02-19 | 济南大学 | Fluorescent probe for detecting polarity in cells and preparation method and application thereof |
| CN110724524A (en) * | 2019-12-02 | 2020-01-24 | 济南大学 | Fluorescent probe for detecting polarity in cells and preparation method and application thereof |
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| CN111925316B (en) * | 2020-08-19 | 2023-08-04 | 安徽大学 | Two-photon fluorescence polar probe based on 4-fluorophenylethynyl and preparation method and application thereof |
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| CN113429335B (en) * | 2021-06-25 | 2023-05-16 | 安徽大学 | Lysosome-targeted dual-response two-photon fluorescent probe and preparation method and application thereof |
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