CN109293632A - A kind of non-reactive mitochondria tracking fluorescence probe and its application containing 12 carbon alkyl chains - Google Patents
A kind of non-reactive mitochondria tracking fluorescence probe and its application containing 12 carbon alkyl chains Download PDFInfo
- Publication number
- CN109293632A CN109293632A CN201811259726.1A CN201811259726A CN109293632A CN 109293632 A CN109293632 A CN 109293632A CN 201811259726 A CN201811259726 A CN 201811259726A CN 109293632 A CN109293632 A CN 109293632A
- Authority
- CN
- China
- Prior art keywords
- mitochondria
- probe
- fluorescence probe
- ecpi
- reactive
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- 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
- G01N21/6486—Measuring fluorescence of biological material, e.g. DNA, RNA, cells
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
Abstract
The non-reactive mitochondria containing 12 carbon alkyl chains that the invention discloses a kind of tracks fluorescence probe and its is marking or showing that mitochondria is distributed in cell, and the application in Mitochondrial autophagy observation；The fluorescence probe is the carbazole pyridine salt compounds of the structure as shown in (I).The fluorescence probe can dye mitochondria in normal living cells, especially when mitochondrial membrane potential reduces or disappears, still can be fixed on mitochondria, show that the probe can track the dynamic change of mitochondria.The probe also has preferable two-phpton property, can be used in deep tissues imaging.The probe has hypotoxicity, and is capable of the dynamic process of real-time tracing Mitochondrial autophagy.Indicate that probe of the invention has broad application prospects in fluorescent biolabels field.
Description
Technical field
The present invention relates to a kind of fluorescence probe of targetted mitochondria and its applications, more particularly to one kind to contain 12 carbon alkyl chains
Non-reactive mitochondria tracking fluorescence probe and its marking or showing that mitochondria is distributed in cell, and in Mitochondrial autophagy
Application in observation.
Background technique
In the entire cell physiological period, the form and number for tracking mitochondria are for physiology, pathology and pharmacology
Research have great importance.Research shows that the form of mitochondria will be by the netted of tubulose in the early stage of Apoptosis
Structure becomes dotted or fragment shape.There are many tools that can observe the form and number of mitochondria at present, for example scanning electron is shown
Micro mirror (SEM), immunofluorescence technique (IFM) and the fluorescent microscopic imaging method for being aided with fluorescence probe.In these three methods, SEM and
The operating procedure of IFM is extremely complex, is suitable only for fixed biological sample, cannot in active biological sample real-time tracing line
The dynamic change of plastochondria.And be aided with the fluorescent microscopic imaging method of fluorescence probe due to it is easy with operating procedure, to the damage of sample
Hurt smaller and can be used for the advantages that active biological sample is imaged, become real-time tracing mitochondria dynamic change simply there are efficacious prescriptions
Method.
Current mitochondria fluorescence probe is broadly divided into two kinds: traditional cationic salts type mitochondrial probe and reaction molded line
Plastochondria tracks probe.Traditional cationic mitochondrial probe such as Rhodamine 123, TMRM etc., by mitochondria it is biggish-
180mV film potential (MMP) targetted mitochondria.When MMP is reduced or is disappeared, these probes will be fallen from mitochondria, from
And it cannot achieve tracking mitochondria.In order to solve this problem, researcher develops response type mitochondria tracking probe, including quotient
The MitoTracker plurality of probes of industry and response type mitochondria reported in the literature track probe.MitoTracker series
Probe is the cationic compound containing benzyl chloride group.These probes can gather mitochondria by electrostatic interaction,
Then nucleophilic displacement of fluorine occurs for the nucleophiles such as sulfydryl on benzyl chloride group and mitochondrial protein or peptide, thus solid by covalent bond
It is scheduled on mitochondria.Response type mitochondria tracking probe reported in the literature is based on this similar principle at present.Such as Han etc.
People reports the mitochondrial probe containing chloracetyl, and chloracetyl can react to be formed with the sulfydryl on mitochondrial protein
Covalent bond (Han, S., et al., 2012, Anal.Methods 4,1699-1703)；Sessler, Kang and Kim et al. exploitation
One mitochondrial probe with benzyl chloride based on naphthalimide, the probe be also can on mitochondrial protein
Sulfydryl occur nucleophilic displacement of fluorine (Sessler, J.L., Kang, C., Kim, J.S., et al., 2014, J.Am.Chem.Soc.136,
14136-14142)；Xiao and Pang et al. design have synthesized one on triphenylphosphine containing the mitochondrial probe of aldehyde radical, are somebody's turn to do
With the amino on mitochondrial membrance protein condensation reaction can occur for probe, make it possible to be fixed on mitochondria (Xiao, Y., Pang,
Y.,et al.,2015,Analyst,140,5488-5494)。
Although these response type mitochondrias tracking probe can be used for tracking the form and number of mitochondria, their meetings
Consume sulfydryl or amino on mitochondrial protein.Sulfydryl is a part of cysteine residues, the redox of cysteine residues
State properties many for stability, enzymatic activity and protein structure of protein etc. have a major impact.Amino is constitutive protein matter
Amino acid important constituent.Therefore, whether existing commercialized MitoTracker probe or it has been reported that
Mitochondria tracking type probe, will affect the property of mitochondrial protein after dyeing, to influence mitochondria normal new old generation
It thanks to state, and then high toxicity is generated to living cells.It is glimmering in relation to the non-reactive mitochondria tracking containing 12 carbon alkyl chains through retrieving
Light probe and its mark or show mitochondria in normal live cells, mitochondrial membrane potential reduce living cells in or mitochondria
The application being distributed in the cell that film potential disappears, or had not been reported in the application observed in intracellular mitochondrial autophagy.
Summary of the invention
In view of the deficiencies of the prior art, the problem to be solved in the present invention is to provide a kind of non-reactions containing 12 carbon alkyl chains
Molded line plastochondria tracks fluorescence probe and its is marking or showing that mitochondria is distributed in cell, and in Mitochondrial autophagy observation
Using.
The non-reactive mitochondria tracking fluorescence probe of the present invention for containing 12 carbon alkyl chains, it is characterised in that: should
Fluorescence probe is the compound of structure shown in formula (I):
The chemical name of compound shown in formula (I) are as follows: (E) -1- dodecyl -4- (2- (9- (2- ethoxyethyl group) -9H-
Carbazole -3- alkenyl) vinyl)-pyridine -1- salt compounded of iodine.Name are as follows: ECPI-12.
The Summarization for Preparation Methods of compound (ECPI-12) shown in above-mentioned formula (I) is as follows:
Synthesis is divided into four steps: being that carbazole reacts generation 9- (2- ethoxyethyl group) -9H- click with 2- bromoethyl ether first
Azoles；Then 9- (2- ethoxyethyl group) -9H- carbazole, phosphorus oxychloride and dimethylformamide (DMF) are reacted by Vilsmeier
Obtain 9- (2- ethoxyethyl group) -9H- carbazole -3- formaldehyde；4- picoline and 1- iodine dodecane are heated to reflux to obtain 1- 12
Alkyl -4- picoline -1- iodide；Last 9- (2- ethoxyethyl group) -9H- carbazole -3- formaldehyde and 1- dodecyl -4- first
Yl pyridines -1- iodide react to obtain final product (E) -1- dodecyl -4- (2- (9- (2- ethoxy by Knoevenagel
Base ethyl) -9H- carbazole -3- alkenyl) vinyl)-pyridine -1- salt compounded of iodine (ECPI-12).
It is as follows that compound (ECPI-12) shown in above-mentioned formula (I) prepares reaction equation:
a,CH3CH2OCH2CH2Br,KOH,DMF；b,POCl3,DMF,CHCl3；c,C12H25I,MeOH；d,
pyrrolidine,MeOH
The synthetic route of Scheme 1.ECPI-12
The non-reactive mitochondria tracking fluorescence probe of the present invention for containing 12 carbon alkyl chains is marking or is showing line grain
What body was distributed in normal live cells, in the living cells that mitochondrial membrane potential reduces or in the cell of mitochondrial membrane potential disappearance answers
With.
The non-reactive mitochondria tracking fluorescence probe of the present invention for containing 12 carbon alkyl chains is in observation intracellular grain
Application in body autophagy.
In above-mentioned application: the normal live cells refer to thin inner mitochondria film current potential be in normal value zooblast or
Cancer cell.
Wherein: the cancer cell is preferably HeLa cell.
Experiment discovery: non-reactive mitochondria tracking fluorescence probe of the present invention can be in normal live cells, mitochondria
Highly selective labeled mitochondria in the cell that the living cells or mitochondrial membrane potential that film potential reduces disappear, and can chase after in real time
The dynamic process of track Mitochondrial autophagy provides simple and direct, intuitive biological detection reagent for the relevant research of mitochondria.Also indicate
Compound ECPI-12 of the present invention has a wide range of applications as mitochondria fluorescence probe.
The invention discloses the non-reactive mitochondria tracking fluorescence probes and its biologic applications of a kind of 12 carbon alkyl chains.
It is a large amount of experiments have shown that: fluorescence probe ECPI-12 of the present invention can dye mitochondria in normal living cells, especially
It is that still can be fixed on mitochondria when mitochondrial membrane potential reduces or disappears, show that ECPI-12 can track mitochondria
Dynamic change.And ECPI-12 has preferable two-phpton property, can be used in deep tissues imaging.It is of the present invention non-
Response type mitochondria, which tracks fluorescence probe, has hypotoxicity, and is capable of the dynamic process of real-time tracing Mitochondrial autophagy.Indication
ECPI-12 has broad application prospects in fluorescent biolabels field.
Detailed description of the invention
Fig. 1: normal activity HeLa cell, the CCCP of dark red probe (MTDR) dyeing are tracked by ECPI-12 and mitochondria
The confocal fluorescent picture of the fixed HeLa cell of the HeLa cell and paraformaldehyde of reason.
The common location coefficient of ECPI-12 and MTDR label in the picture (Merge) of superposition.Excitation wavelength: ECPI-12 is
473nm, MTDR 633nm；Acquire wave band: ECPI-12 500-600nm, MTDR 650-750nm.
Fig. 2: by the HeLa cell and Rat Skeletal that the normal activity HeLa cell of ECPI-12 dyeing, paraformaldehyde are fixed
The two-photon fluorescence picture of muscular tissue.
Excitation wavelength: 840nm；Acquire wave band: 495-540nm.Scale is 20 μm.
Fig. 3: by the survival rate of the active HeLa cell of various concentration ECPI-12 and MTDR dyeing.
Fig. 4: it in the presence of 10 μM of CCCP and 7.5 μM of pepstatin A, is tracked by ECPI-12 (a, 2 μM) and lysosome
The HeLa cell confocal fluorescent picture of (0.2 μM, b) of probe (LTR) dyeing.
C) superposition of a and b；Scheming the white box regional enlarged drawing piece in a, b, c is respectively to scheme d, e, f；G) DIC picture；Scheme d
Middle arrow refers to the mitochondria marked by ECPI-12, schemes arrow in e and refers to the acidic organelles marked by LTR；h)
ECPI-12 is along the normalized fluorescence intensity profile in white arrow in figure f.
ECPI-12, exciting light 405nm, collection wave band are 450-540nm；LTR, exciting light 543nm collect wave band
For 600-700nm.Scale is 5 μm.
The dynamic process fluorescence picture of Fig. 5: ECPI-12 real-time tracing Mitochondrial autophagy.
Specific embodiment
The synthesis of 1 ECPI-12 of embodiment
Take 0.27g 9- (2- ethoxyethyl group) -9H- carbazole -3- formaldehyde (1mmol) and 0.39g 1- dodecyl -4- first
Yl pyridines -1- iodide (1mmol) are added in 5mL ethyl alcohol and stir.Then 200 μ L nafoxidines are added, stir at room temperature
Mix 5h.After reaction, it pours the mixture into petroleum ether, yellow solid is precipitated.After recrystallization, yellow solid final product is obtained
As (E) -1- dodecyl -4- (2- (9- (2- ethoxyethyl group) -9H- carbazole -3- alkenyl) vinyl)-pyridine -1- salt compounded of iodine,
Yield is about 67%.
1H NMR(300MHz,DMSO-d6), δ (ppm): 8.90 (d, J=6.90Hz, 2H), 8.56 (s, 1H), 8.21 (q, J
=8.00Hz, 4H), 7.89 (q, J=3.30Hz, 1H), 7.75 (d, J=8.70Hz, 1H), 7.69 (d, J=8.10Hz, 1H),
7.49-7.56 (m, 2H), 7.29 (t, J=7.35Hz, 1H), 4.61 (t, J=5.25Hz, 2H), 4.47 (t, J=7.20Hz,
2H), 3.77 (t, J=5.10Hz, 2H), 3.32-3.41 (m, 2H), 1.91 (s, 2H), 1.26 (d, J=15.60Hz, 18H),
0.96 (t, J=7.05Hz, 3H), 0.84 (t, J=6.60Hz, 3H)13C NMR(400MHz,DMSO),δ(ppm):153.98,
144.39,143.11,142.35,141.37,126.82,126.76,126.54,123.57,123.17,122.54,121.54,
120.75,120.46,120.24,110.96,110.69,68.63,66.11,59.97,43.41,31.74,30.93,29.45,
29.34,29.22,29.15,28.83,25.89,22.53,15.43,14.39.HRMS (m/z)=511.36, C35H47N2O+。
It is as follows that above compound (ECPI-12) prepares reaction equation:
a,CH3CH2OCH2CH2Br,KOH,DMF；b,POCl3,DMF,CHCl3；c,C12H25I,MeOH；d,
pyrrolidine,MeOH
The synthetic route of Scheme 1.ECPI-12
2 cell culture of embodiment and colouring method
Cell culture:
HeLa cell is grown in the H-DMEM culture medium containing 10% FBS and 1% penicillin and streptomysin.All
Cell is all in the CO containing 5%237 DEG C of constant incubator in cultivate.
Cell dyeing:
ECPI-12 is dissolved in the storing liquid for being made into that concentration is 1mM in DMSO.
HeLa cell grows 48h on the cover slip, and final concentration of 2 μM of ECPI-12 is then added, and is incubated at 37 DEG C
30min completes dyeing.
Embodiment 3 ECPI-12's and MTDR redyes experiment
MTDR is dissolved in the storing liquid for being made into that concentration is 0.1mM in DMSO.
1. in living cells: active HeLa cell is first incubated for 30min by 0.2 μM of MTDR, is then incubated by 2 μM of ECPI-12
Educate 30min；2. in the living cells that mitochondrial membrane potential reduces: active HeLa cell is first incubated for 30min by 0.2 μM of MTDR, so
30min is incubated for by 2 μM of ECPI-12 afterwards；30min is handled with 15 μM of CCCP again；3. in the cell that mitochondrial membrane potential disappears:
Active HeLa cell is first incubated for 30min by 0.2 μM of MTDR, is then incubated for 30min by 2 μM of ECPI-12；Again with 4% poly
The fixed reason 30min of formaldehyde.Before contaminating another probe every time, cell is washed 3 times with PBS.
The result is shown in Figure 1.
Fig. 1: the HeLa cell and poly first of the normal activity HeLa cell, CCCP processing that are dyed by ECPI-12 and MTDR
The confocal fluorescent picture of the fixed HeLa cell of aldehyde.
The common location coefficient of ECPI-12 and MTDR label in the picture (Merge) of superposition.Excitation wavelength: ECPI-12 is
473nm, MTDR 633nm；Acquire wave band: ECPI-12 500-600nm, MTDR 650-750nm.
4 two-photon cell of embodiment, imaging of tissue
Cell imaging: by 2 μM of ECPI-12 in 37 DEG C of incubation activity HeLa cell 30min, then with 4% paraformaldehyde
The fixed HeLa cell 30min dyed, then with two-photon fluorescence microscope respectively to activity and fixed HeLa cell
Imaging.
Imaging of tissue: Rat Skeletal muscular tissue is directly obtained from Vist mouse.It is incubated at room temperature with 5 μM of ECPI-12
1h.Then it is imaged with two-photon fluorescence microscope.
As a result see Fig. 2.
Fig. 2: by the HeLa cell and Rat Skeletal that the normal activity HeLa cell of ECPI-12 dyeing, paraformaldehyde are fixed
The two-photon fluorescence picture of muscular tissue.Excitation wavelength: 840nm；Acquire wave band: 495-540nm.Scale is 20 μm.
The experiment of 5 cytotoxicity test of embodiment
The toxotest of ECPI-12 is completed with MTT reagent.
HeLa and SiHa cell is planted respectively in 96 orifice plates, the cell density of average individual hole is 10000/mL, raw
Length is for 24 hours.Then it is separately added into the ECPI-12 and MTDR (200 hole μ L/) that concentration is 2,1,0.5 μM in experimental group, control group is added
H-DMEM (200 hole μ L/).Then two 96 orifice plates are put into the CO containing 5%237 DEG C of constant incubator in for 24 hours.Then
MTT (5mg/mL) is separately added into experimental group and control group.After placing 4h in the incubator, the liquid in each hole is taken
Out, 200 μ L DMSO are separately added into, to dissolve purple crystals.After 20min, each hole is tested in the extinction of 570nm with microplate reader
Degree.Calculate the survival rate of cell.The cytotoxicity experiment is repeated 3 times.
As a result see Fig. 3.
Fig. 3: by the survival rate of the active HeLa cell of various concentration ECPI-12 and MTDR dyeing.
Embodiment 6 tracks Mitochondrial autophagy process experiment with ECPI-12
(1) LTR is dissolved in the storing liquid for being made into that concentration is 0.1mM in DMSO.HeLa cell is first incubated for by 2 μM of ECPI-12
Then 30min handles 4h with 10 μM of CCCP and 7.5 μM of pepstatin A.Then 15min is dyed with 0.2 μM of LTR.Into
During row fluorescence imaging, CCCP and pepstatin A cannot be removed.
(2) it monitors ECPI-12 and lysosome tracks near-infrared probe (LT-NIR) redying in mitochondria autophagy process
The variation of rate.HeLa cell is first incubated for by 2 μM of ECPI-12 and 0.2 μM of LT-NIR, then with 10 μM CCCP and 7.5 μM
Pepstatin A processing.The fluorescence picture at 0h, 0.5h, 1h, 2h, 3h and 4h time point is recorded respectively and has obtained the time point
Redye rate.
As a result see Fig. 4 and Fig. 5.
Fig. 4: in the presence of 10 μM of CCCP and 7.5 μM of pepstatin A, by ECPI-12 (a, 2 μM) and LTR (0.2 μM,
B) the HeLa cell confocal fluorescent picture dyed.C) superposition of a and b；Scheme the white box regional enlarged drawing piece difference in a, b, c
To scheme d, e, f；G) DIC picture；Yellow arrows in figure d refer to the mitochondria marked by ECPI-12, scheme the blue arrow in e
Head refers to the acidic organelles marked by LTR；H) ECPI-12 is along the normalized fluorescence intensity in white arrow in figure f
Distribution map.ECPI-12, exciting light 405nm, collection wave band are 450-540nm；LTR, exciting light 543nm, collecting wave band is
600-700nm.Scale is 5 μm.
The dynamic process fluorescence picture of Fig. 5: ECPI-12 real-time tracing Mitochondrial autophagy.
Claims (5)
1. a kind of non-reactive mitochondria containing 12 carbon alkyl chains tracks fluorescence probe, it is characterised in that: the fluorescence probe
It is the compound of structure shown in formula (I):
Its chemical name is: (E) -1- dodecyl -4- (2- (9- (2- ethoxyethyl group) -9H- carbazole -3- alkenyl) ethylene
Base)-pyridine -1- salt compounded of iodine；Name are as follows: ECPI-12.
2. the non-reactive mitochondria tracking fluorescence probe described in claim 1 containing 12 carbon alkyl chains is marking or is showing line grain
What body was distributed in normal live cells, in the living cells that mitochondrial membrane potential reduces or in the cell of mitochondrial membrane potential disappearance answers
With.
3. the non-reactive mitochondria tracking fluorescence probe described in claim 1 containing 12 carbon alkyl chains is in observation intracellular grain
Application in body autophagy.
4. application as claimed in claim 2, it is characterised in that: the normal live cells refer to that thin inner mitochondria film current potential is in just
The zooblast or cancer cell of constant value.
5. application as claimed in claim 4, it is characterised in that: the cancer cell is HeLa cell.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811259726.1A CN109293632A (en) | 2018-10-26 | 2018-10-26 | A kind of non-reactive mitochondria tracking fluorescence probe and its application containing 12 carbon alkyl chains |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811259726.1A CN109293632A (en) | 2018-10-26 | 2018-10-26 | A kind of non-reactive mitochondria tracking fluorescence probe and its application containing 12 carbon alkyl chains |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN109293632A true CN109293632A (en) | 2019-02-01 |
Family
ID=65158887
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201811259726.1A Pending CN109293632A (en) | 2018-10-26 | 2018-10-26 | A kind of non-reactive mitochondria tracking fluorescence probe and its application containing 12 carbon alkyl chains |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109293632A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110776458A (en) * | 2019-11-01 | 2020-02-11 | 济南大学 | Fluorescent probe for detecting mitochondrial membrane potential and preparation method and application thereof |
| CN111362927A (en) * | 2020-04-16 | 2020-07-03 | 江西科技师范大学 | Interface targeting type mitochondrial probe and preparation method and application thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106588750A (en) * | 2016-12-07 | 2017-04-26 | 山东大学 | Disposable and rapid octadecyl-chain-containing targeting mitochondrion fluorescent probe and application thereof |
| CN106632264A (en) * | 2016-12-19 | 2017-05-10 | 山东大学 | Probe for clearly distinguishing cell membrane-lipid raft microdomain from non-lipid-raft microdomain by using two fluorescence colors and simultaneously imaging microdomains and application of probe |
| CN107024462A (en) * | 2017-04-17 | 2017-08-08 | 山东大学 | One group is used for the fluorescence probe of nucleus construction and cell configuration in display living cells simultaneously |
-
2018
- 2018-10-26 CN CN201811259726.1A patent/CN109293632A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106588750A (en) * | 2016-12-07 | 2017-04-26 | 山东大学 | Disposable and rapid octadecyl-chain-containing targeting mitochondrion fluorescent probe and application thereof |
| CN106632264A (en) * | 2016-12-19 | 2017-05-10 | 山东大学 | Probe for clearly distinguishing cell membrane-lipid raft microdomain from non-lipid-raft microdomain by using two fluorescence colors and simultaneously imaging microdomains and application of probe |
| CN107024462A (en) * | 2017-04-17 | 2017-08-08 | 山东大学 | One group is used for the fluorescence probe of nucleus construction and cell configuration in display living cells simultaneously |
Non-Patent Citations (1)
| Title |
|---|
| 张若瑶: "原位成像/追踪线粒体以及原位成像质膜超微结构的长烷基链型活细胞荧光探针的研制", 《山东大学博士论文》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110776458A (en) * | 2019-11-01 | 2020-02-11 | 济南大学 | Fluorescent probe for detecting mitochondrial membrane potential and preparation method and application thereof |
| CN110776458B (en) * | 2019-11-01 | 2021-10-26 | 济南大学 | Fluorescent probe for detecting mitochondrial membrane potential and preparation method and application thereof |
| CN111362927A (en) * | 2020-04-16 | 2020-07-03 | 江西科技师范大学 | Interface targeting type mitochondrial probe and preparation method and application thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN109293633A (en) | A kind of non-reactive mitochondria tracking fluorescence probe IVPI-12 and its application | |
| CN106590630B (en) | A kind of mitochondrial membrane potential fluorescence probe of space dependent form and its application | |
| CN103265947B (en) | A kind of indolepyridinium salt fluorescent probe for RNA in viable cell and kernel imaging | |
| CN106588750B (en) | A kind of fluorescence probe of the disposable and quick targetted mitochondria of the chain containing octadecyl and its application | |
| CN106946869B (en) | The fluorescence probe of fat drips in a kind of specific marker cell | |
| CN102127055B (en) | Single-photon and two-photon homocysteine fluorescent probes and use thereof | |
| Dmitriev et al. | Luminescence lifetime imaging of three-dimensional biological objects | |
| CN106632304A (en) | Two-photon RNA (Ribonucleic Acid) fluorescent probe and application thereof in living cell imaging | |
| CN105062467B (en) | Rotor-type two-photon mitochondrion fluorescence probe and application thereof | |
| CN106905309A (en) | A kind of very high selectivity and the amphipathic fat drips fluorescence probe of tool and its application | |
| CN109293632A (en) | A kind of non-reactive mitochondria tracking fluorescence probe and its application containing 12 carbon alkyl chains | |
| CN106814057B (en) | A kind of fluorescence probe, synthetic method and its application being used for Selective recognition ATP based on aggregation inducing fluorescence enhancement characteristic | |
| CN105566207A (en) | Two-photon deep red emission fluorescent probe for imaging cell membranes in tissues based on molecular rotors | |
| CN107200718A (en) | Detect compound, method and the kit of the serobilas of DNA G tetra- | |
| CN102993763A (en) | Single charge boron fluroride complexing dipyrrole methenyl fluorochrome and application thereof | |
| CN103275699B (en) | Pyrrole pyridine salt fluorescent probe used for RNA (ribonucleic acid) and nucleolus imaging in living cell | |
| CN110057804A (en) | Application of the fluorescent carbon point based on N- methyl-o-phenylenediamine hydrochloride in lysosome targeting | |
| CN108822031A (en) | A kind of red transmitting fluorescence probe of two-photon detecting mitochondria | |
| CN103710021B (en) | Fluorescent dye with nitrobenzimidazole as RNA (ribonucleic acid) recognition group as well as preparation method and application of fluorescent dye | |
| CN103709203B (en) | One class double-core ruthenium complex and preparation method thereof and as the application of living cells fluorescent dye | |
| CN105906619B (en) | A kind of two-photon fluorescence probe and its preparation method and application | |
| CN103382189B (en) | One class cyanine compound, its preparation method and application | |
| CN107024462B (en) | One group of fluorescence probe for being used for while showing living cells core construction and cell entirety | |
| Ameer-Beg et al. | Special issue on fluorescence lifetime imaging (FLIM): from fundamentals to applications | |
| Arranja et al. | Double-tailed long chain BODIPYs-Synthesis, characterization and preliminary studies on their use as lipid fluorescence probes |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| WD01 | Invention patent application deemed withdrawn after publication | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20190201 |