CN109293633A - A kind of non-reactive mitochondria tracking fluorescence probe IVPI-12 and its application - Google Patents
A kind of non-reactive mitochondria tracking fluorescence probe IVPI-12 and its application Download PDFInfo
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- CN109293633A CN109293633A CN201811259728.0A CN201811259728A CN109293633A CN 109293633 A CN109293633 A CN 109293633A CN 201811259728 A CN201811259728 A CN 201811259728A CN 109293633 A CN109293633 A CN 109293633A
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- 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
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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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
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
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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
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N2021/6439—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" with indicators, stains, dyes, tags, labels, marks
Abstract
The invention discloses a kind of non-reactive mitochondrias to track fluorescence probe IVPI-12, contains 12 carbon alkyl chains in the probe chemical structure, is the indolepyridinium salt compounds of structure shown in formula (I).The invention also discloses the probes to mark or show that mitochondria is distributed in cell, with the application in Mitochondrial autophagy is observed, experiment confirms that the probe can dye mitochondria in normal living cells, especially when mitochondrial membrane potential reduces or disappears, still it 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.Probe of the invention has hypotoxicity, and is capable of the dynamic process of real-time tracing Mitochondrial autophagy, 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 IVPI-12 and its marking or showing that mitochondria is distributed in cell, and it is online
Application in the observation of plastochondria autophagy.
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
It light probe such as (E) -4- (2- (1H- indoles -3- alkenyl) vinyl) -1- dococylpyridinium -1- salt compounded of iodine and its is marking or aobvious
Timberline plastochondria divides in normal live cells, in the living cells that mitochondrial membrane potential reduces or in the cell of mitochondrial membrane potential disappearance
The application of cloth, 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 IVPI-12 and its is marking or showing that mitochondria is distributed in cell, and in Mitochondrial autophagy
Application in observation.
Non-reactive mitochondria of the present invention tracks fluorescence probe IVPI-12, it is characterised in that: the fluorescence probe
Contain 12 carbon alkyl chains in chemical structure, be the compound of structure shown in formula (I):
The chemical name of compound shown in formula (I) are as follows: (E) -4- (2- (1H- indoles -3- alkenyl) vinyl) -1- dodecane
Yl pyridines -1- salt compounded of iodine；Name are as follows: non-reactive mitochondria tracks fluorescence probe IVPI-12.
The Summarization for Preparation Methods of compound (IVPI-12) shown in above-mentioned formula (I) is as follows:
Synthesis is divided into four steps: 4- picoline and 1- iodine dodecane are heated to reflux to obtain 1- dodecyl -4- methyl first
Pyridine -1- iodide；Then 1H- indole -3-formaldehyde passes through with 1- dodecyl -4- picoline -1- iodide
Knoevenagel reacts to obtain final product IVPI-12.
It is as follows that compound (IVPI-12) shown in above-mentioned formula (I) prepares reaction equation:
Non-reactive mitochondria tracking fluorescence probe IVPI-12 of the present invention is marking or is showing that mitochondria is normally being lived
In cell, in the living cells that mitochondrial membrane potential reduces or the application that is distributed in cell that mitochondrial membrane potential disappears.
Non-reactive mitochondria tracking fluorescence probe IVPI-12 of the present invention is in observation intracellular mitochondrial autophagy
Using.
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 and 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 IVPI-12 of the present invention has a wide range of applications as mitochondria fluorescence probe.
The invention discloses a kind of non-reactive mitochondria tracking fluorescence probe IVPI-12 and its biologic applications.Largely
Experiments have shown that: fluorescence probe IVPI-12 of the present invention can dye mitochondria in normal living cells, especially online
When mitochondrial membrane potential is reduced or disappeared, it still can be fixed on mitochondria, show that IVPI-12 can track the dynamic of mitochondria
Variation.IVPI-12 has preferable two-phpton property, can be used in deep tissues imaging.Non-reactive mitochondria of the invention
Tracking fluorescence probe IVPI-12 has hypotoxicity, and is capable of the dynamic process of real-time tracing Mitochondrial autophagy.The above results show
IVPI-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 IVPI-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 IVPI-12 and MTDR label in the picture (Merge) of superposition.Excitation wavelength: IVPI-12 is
473nm, MTDR 633nm；Acquire wave band: IVPI-12 500-600nm, MTDR 650-750nm.
Fig. 2: by the HeLa cell and Rat Skeletal that the normal activity HeLa cell of IVPI-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 IVPI-12 and MTDR dyeing.
Fig. 4: in the presence of 10 μM of CCCP and 7.5 μM of pepstatin A, by IVPI-12 (a, 2 μM) and LTR (0.2 μM,
B) the HeLa cell confocal fluorescent picture dyed.
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
In yellow arrows refer to by IVPI-12 mark mitochondria, scheme e in blue arrow refer to by LTR mark acidity
Organelle；H) IVPI-12 is along the normalized fluorescence intensity profile in white arrow in figure f.IVPI-12, exciting light are
405nm, collection wave band are 450-540nm；LTR, exciting light 543nm, collection wave band are 600-700nm.Scale is 5 μm.
The dynamic process fluorescence picture of Fig. 5: IVPI-12 real-time tracing Mitochondrial autophagy.
Specific embodiment
The synthesis of 1 IVPI-12 of embodiment
Take 0.15g 1H- indole -3-formaldehyde (1mmol) and 0.39g 1- dodecyl -4- picoline -1- iodide
(1mmol) is added in 5mL ethyl alcohol and stirs.Then 200 μ L nafoxidines are added, 5h is stirred at room temperature.After reaction,
It pours the mixture into petroleum ether, Orange red solid is precipitated.After recrystallization, obtaining Orange red solid final product is (E) -4-
(2- (1H- indoles -3- alkenyl) vinyl) -1- dococylpyridinium -1- salt compounded of iodine, yield is about 73%.
1H NMR(300MHz,CDCl3), δ (ppm): 8.14 (s, 1H), 7.76-7.63 (m, 5H), 7.62 (d, J=
3.60Hz, 1H), 7.33 (s, 1H), 7.27 (s, 1H), 7.19 (d, J=2.40Hz, 2H), 6.58 (d, J=15.60Hz, 1H),
4.25 (s, 1H), 1.75 (s, 2H), 1.23 (s, 18H), 0.87 (t, J=6.60Hz, 3H)13C NMR(400MHz,DMSO),δ
(ppm):155.03,143.78,138.03,137.02,132.85,125.40,123.39,122.36,121.61,120.90,
117.28,114.12,113.07,59.51,31.74,30.89,29.45,29.34,29.23,29.15,28.84,25.89,
22.53,14.38.HRMS (m/z)=389.30, C27H37N2 +。
It is as follows that above compound (IVPI-12) prepares reaction equation:
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 cells are all in the CO containing 5%237 DEG C of constant incubator in cultivate.
Cell dyeing:
IVPI-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 IVPI-12 is then added and is incubated at 37 DEG C
30min completes dyeing.
Embodiment 3 IVPI-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 IVPI-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 IVPI-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 IVPI-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 IVPI-12 and MTDR
The confocal fluorescent picture of the fixed HeLa cell of aldehyde.
The common location coefficient of IVPI-12 and MTDR label in the picture (Merge) of superposition.Excitation wavelength: IVPI-12 is
473nm, MTDR 633nm；Acquire wave band: IVPI-12 500-600nm, MTDR 650-750nm.
4 two-photon cell of embodiment, imaging of tissue
Cell imaging: by 2 μM of IVPI-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 IVPI-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 IVPI-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 IVPI-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 IVPI-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 IVPI-12 and MTDR dyeing.
Embodiment 6 tracks Mitochondrial autophagy process experiment with IVPI-12
(1) lysosome tracking searchlight (LTR) is dissolved in the storing liquid for being made into that concentration is 0.1mM in DMSO.HeLa cell
It first is incubated for 30min by 2 μM of IVPI-12, then handles 4h with 10 μM of CCCP and 7.5 μM of pepstatin A.Then with 0.2 μM
LTR dyes 15min.During carrying out fluorescence imaging, CCCP and pepstatin A cannot be removed.
(2) it monitors IVPI-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 IVPI-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 IVPI-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 IVPI-12, scheme the blue arrow in e
Head refers to the acidic organelles marked by LTR；H) IVPI-12 is along the normalized fluorescence intensity in white arrow in figure f
Distribution map.IVPI-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: IVPI-12 real-time tracing Mitochondrial autophagy.
Claims (5)
1. a kind of non-reactive mitochondria tracks fluorescence probe IVPI-12, it is characterised in that: in the fluorescence probe chemical structure
It is the compound of structure shown in formula (I) containing 12 carbon alkyl chains:
Its chemical name is: (E) -4- (2- (1H- indoles -3- alkenyl) vinyl) -1- dococylpyridinium -1- salt compounded of iodine；Name
Are as follows: non-reactive mitochondria tracks fluorescence probe IVPI-12.
Marking or showing mitochondria normal 2. non-reactive mitochondria described in claim 1 tracks fluorescence probe IVPI-12
In living cells, in the living cells that mitochondrial membrane potential reduces or the application that is distributed in cell that mitochondrial membrane potential disappears.
3. non-reactive mitochondria described in claim 1 tracks fluorescence probe IVPI-12 in observation intracellular mitochondrial autophagy
Application.
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.
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| CN109851553A (en) * | 2018-12-25 | 2019-06-07 | 济南大学 | A kind of mitochondria-kernel migration-type film potential fluorescence probe and its synthesis and application |
| CN110305055A (en) * | 2019-07-12 | 2019-10-08 | 济南大学 | A kind of fluorescence probe and the preparation method and application thereof identifying mitochondria viscosity |
| 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 |
| CN111398269A (en) * | 2020-04-09 | 2020-07-10 | 湖北科技学院 | Method for preparing PH test paper by indole pyridinium derivative |
| CN111393411A (en) * | 2020-04-09 | 2020-07-10 | 湖北科技学院 | Indole pyridinium derivative as pH indicator and synthetic method thereof |
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| 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 |
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| CN111393411A (en) * | 2020-04-09 | 2020-07-10 | 湖北科技学院 | Indole pyridinium derivative as pH indicator and synthetic method thereof |
| CN111393411B (en) * | 2020-04-09 | 2021-05-04 | 湖北科技学院 | Indole pyridinium derivative as pH indicator and synthetic method thereof |
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| 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 |
| CN113848197A (en) * | 2021-10-26 | 2021-12-28 | 常熟理工学院 | Application of fluorescent probe |
| CN113848197B (en) * | 2021-10-26 | 2023-10-13 | 常熟理工学院 | Use of fluorescent probe |
| CN116217545A (en) * | 2021-12-06 | 2023-06-06 | 中国科学院上海药物研究所 | Mitochondria-targeted positron emission or fluorescence probe, preparation method and application thereof |
| WO2023104009A1 (en) * | 2021-12-06 | 2023-06-15 | 中国科学院上海药物研究所 | Mitochondria-targeted positron emission or fluorescent probe, and preparation method therefor and use thereof |
| CN116217545B (en) * | 2021-12-06 | 2024-01-02 | 中国科学院上海药物研究所 | Mitochondria-targeted positron emission or fluorescence probe, preparation method and application thereof |
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