CN110078714A - A kind of two-photon viscosity probe and its preparation method and application positioning mitochondria - Google Patents
A kind of two-photon viscosity probe and its preparation method and application positioning mitochondria Download PDFInfo
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Abstract
The present invention provides the two-photon fluorescence probes that one kind can distinguish different viscosities:.The probe is by 4-(lignocaine) salicylide, ethyl acetoacetate, 1,3,3- trimethyl -2- methylene indoleacetaldehyde raw material is obtained, and step is simple, purifying is convenient, high income.Fluorescence probe of the invention, sensitivity with higher, good optical stability and to viscosity specificly-response；And realize the detection of mitochondria viscosity in the cell.
Description
Technical field
The invention belongs to small organic molecule fluorescence probe fields, and in particular to a kind of two-photon fluorescence for distinguishing different viscosities
Probe and its preparation method and application.
Background technique
Viscosity is to measure the mobility and diffusible principal element of a kind of dense fluid, while being fluid diffusion rate
Primary Reference index.The viscosity of microenvironment play the role of in pathological research it is very important because the variation of viscosity is often
It will affect the progress of various metabolism in cell micro-environment.Mitochondria is a kind of dynamics organelle, Intramitochondrial viscosity
The metabolism of mitochondria is directly affected, the exception of viscosity is related with many diseases.So viscous in detection cell Mitochondria
Degree has great importance for clinical diagnosis and pathological analysis.
Imaging-PAM due to real-time monitoring, background signal is low, high sensitivity the advantages that and become detection biology
Molecule and a kind of important means of biological microenvironment.Two-phpton property has high-penetration degree, few to biological sample damage etc. excellent
It puts and is widely applied in bio-imaging.So it is Intramitochondrial for detecting to develop a kind of new two-photon fluorescence probe
Viscosity is of great significance.
Summary of the invention
Aiming at the problems existing in the prior art, the present invention provides a kind of two-photon fluorescence spy that can distinguish different viscosities
Needle, the probe can be positioned at mitochondria, and the good, high sensitivity of selectivity.
It is a further object of the present invention to provide a kind of synthetic method of above-mentioned fluorescence probe, raw material is easy to get, synthesis step is simple
Single, high income.
Another object of the present invention is to provide a kind of application of above-mentioned fluorescence probe in detection cell viscosity.
To achieve the above object, the present invention adopts the following technical scheme that.
A kind of two-photon viscosity probe positioning mitochondria, chemical name 1,3,3- trimethyl -2- methylene indoles-perfume
Legumin, referred to as Mito-V, structural formula are as shown in the formula (I):
Formula (I).
A kind of synthetic method of above-mentioned two-photon viscosity probe, comprising the following steps:
(1) 4-(lignocaine) salicylide (1) and ethyl acetoacetate (2) are heated to reflux in ethyl alcohol anti-in the presence of piperidines
It answers, isolates and purifies to obtain 3- acetyl butylcoumariii (3):
；
(2) in protective atmosphere, 3- acetyl butylcoumariii (3) and 1,3,3- trimethyl -2- methylene indoleacetaldehydes (4) are deposited in piperidines
It is heated to reflux in ethanol under, isolates and purifies to obtain 1,3,3- trimethyl -2- methylene indoles-cumarin, i.e. probe Mito-V
(5):
。
In step (1), 4- (lignocaine) salicylide: the molar ratio of ethyl acetoacetate is 1:1-1.3.
In step (1), the purification procedures are as follows: the system after reaction is cooled to room temperature, golden yellow precipitate is precipitated,
Pure products are obtained after recrystallizing.
In step (1) and (2), the reaction temperature is 80 DEG C, reaction time 12h.
In step (2), the 3- acetyl butylcoumariii: 1,3,3- trimethyl -2- methylene indoleacetaldehyde: mole of piperidines
Than for 1:1:1.
In step (2), the purification procedures are as follows: the system after reaction is evaporated under reduced pressure, solvent is spin-dried for and is slightly produced
After object, purified product is obtained through pillar layer separation；The mobile phase of the pillar layer separation is the methanol that volume ratio is 1:50 and two
Chloromethanes.
A kind of application of above-mentioned two-photon viscosity probe in the viscosity reagents of preparation detection solution and mitochondria.
The recognition mechanism of fluorescence probe of the present invention is as follows:
Since indoles salt is connected with 3- acetyl butylcoumariii by singly-bound, so indoles can pass through in the case where low viscosity
Singly-bound rotates freely, and keeps entire probe molecule not coplanar, and probe is in "Off" state almost without fluorescence, that is, fluorescence；When
When in the bigger system of viscosity, since rotating freely for indoles is restricted, so that entire probe molecule is coplanar, probe is just
Very strong fluorescence can be issued, i.e. fluorescent switch is opened.So can detecte by this " switching mode " fluorescence probe different
Viscosity.
The invention has the benefit that
It is provided by the present invention distinguish different viscosities fluorescence probe, sensitivity with higher, good optical stability with
And to viscosity specificly-response；And realize the detection of mitochondria viscosity in the cell.Meanwhile the present invention provides the probes
Synthetic method, step is simple, purifying is convenient, high income.
Detailed description of the invention
Fig. 1 is probe1H H NMR spectroscopy；
Fig. 2 is probe13C H NMR spectroscopy；
Fig. 3 is emission spectrum of the probe in different viscosities system；
Fig. 4 is positioning experiment of the probe in mitochondria；
Fig. 5 is the cell imaging application of probe.
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 Mito-V of embodiment
(1) synthesis of compound (3)
By 1.93 g 4-(lignocaines) salicylide (10 mmol) (1) and 1.53 g ethyl acetoacetates (13 mmol) (1),
0.09g piperidines is added in the round-bottomed flask equipped with 20 mL ethyl alcohol, after mixing evenly, is put into 80 DEG C of oil bath pans isothermal reaction about
System after reaction is cooled to room temperature by 12 h after the reaction was completed, and golden yellow precipitate is precipitated, carries out recrystallizing pure after suction filtration
Product 3- acetyl butylcoumariii (3)；
(2) fluorescence probe Cou-MV(5) synthesis:
Weigh 0.244 g 3- acetyl butylcoumariii (3) (1 mmol) and 0.201 g 1,3,3- trimethyl -2- methylene indoles
Acetaldehyde (4) (1 mmol), is added 100 μ L piperidines, the hybrid reaction in 25mL ethyl alcohol, and deoxygenation is warming up to 80 DEG C of back flow reactions
It after 12 h, is evaporated under reduced pressure, is spin-dried for solvent, column is then carried out as mobile phase for the methanol and methylene chloride of 1:50 using volume ratio
Chromatographic purification obtains 1,3,3- trimethyl -2- methylene indoles-cumarin (5).Probe1H H NMR spectroscopy such as Fig. 1,13C H NMR spectroscopy
Such as Fig. 2；
1H NMR (400 MHz, CDCl3) δ 10.04 (d, J = 8.8 Hz, 1H), 8.56 ( s, 1H), 8.29
(m, 1H), 7.44 (d, J = 8.8 Hz, 1H), 7.08 (t, J=7.6 Hz, 1H), 6.97 (t, J = 7.4
Hz, 1H), 6.87 (d, J = 8.0 Hz, 1H), 6.76 (d, J = 8.0 Hz, 1H), 6.63 (dd, J1 =
9.2 Hz, J2 = 4.2 Hz, 1H), 6.52 (d, J = 2.0 Hz, 1H), 5.73 (d, J = 13.2 Hz,
2H), 5.41 (d, J = 8.8 Hz, 1H), 3.47 (q, J = 7.07 Hz, 4H), 3.26 (d, J = 2.4
Hz, 3H), 1.68 (d, J = 2.6 Hz, 6H), 6.97 (m, 6H)；
13C NMR (101 MHz, CDCl3) δ 186.49, 173.62, 165.91, 165.53, 158.14, 152.27,
147.40, 144.29, 142.17, 139.61, 139.39, 131.26, 128.05, 127.81, 122.45,
121.81, 121.70, 121.05, 119.21, 109.48, 108.81, 107.99, 106.99, 99.00, 96.63,
45.06, 29.56, 28.79, 12.49。
Fluorescence spectrum of the 2 fluorescence probe Mito-V of embodiment in different viscosities system
Compound concentration is that the test mother liquor of the dimethyl sulfoxide (DMSO) of 1 mM embodiment, 1 gained fluorescence probe is stand-by；
In test fluid, take respectively 3ml different proportion glycerol and methanol solvent (glycerol: methanol=0:10,1:9,2:8,3:7,4:
6,5:5,6:4,7:3,8:2,9:1,10:0), probe mother liquor (final concentration of 10 μM) then are added, carry out fluorescent scanning (excitation
561 nm of wavelength detects wave band 570-800 nm), relative intensity of fluorescence in each system is measured, as shown in Figure 3.From the figure 3, it may be seen that
With the increase of solvent viscosity, relative intensity of fluorescence becomes strong.
3 fluorescence probe of embodiment is with commercialization probe to the common location of mitochondria
Compound concentration is that the test mother liquor of the dimethyl sulfoxide (DMSO) of 1 mM embodiment, 1 gained fluorescence probe is stand-by；
35 mm of the Hela cell inoculation of suitable density to sterilizing are imaged in culture dish, in CO2Incubator (temperature 37
DEG C, 5 % CO2) in culture, after cell is adherent, while viscosity fluorescence probe Mito-V and mitochondria quotient being added into cell
Industry dyestuff mitochondria is green, makes 10 μM of viscosity fluorescence probe ultimate density, and the green ultimate density of mitochondria is 5 μM.Half an hour
Afterwards, culture medium is discarded, is rinsed cell 3 times with PBS buffer solution, then carrying out fluorescence imaging, (excitation wavelength: 561 nm, green are logical
Road: 500-550 nm；570 nm-620 nm of red channel), as a result as shown in Figure 4.Wherein, (a) is Mito-V logical in red color
The light that road is collected；It (b) is the green light in green channel of mitochondria；(c) be (a) He (b) stacking chart；It (d) is (a) and (b)
Spectral intensity stacking chart.As shown in Figure 4, the probe imaging position green with mitochondria is identical, and common location coefficient is 0.97.
Probe Mito-V is primarily located in the mitochondria in cell, thus probe of the invention can be used to detect cell Mitochondria
Viscosity.
Imaging of 4 fluorescence probe of embodiment in cell
Compound concentration is that the test mother liquor of the dimethyl sulfoxide (DMSO) of 1 mM embodiment, 1 gained fluorescence probe is stand-by；
35 mm of the Hela cell inoculation of suitable density to sterilizing are imaged in culture dish, in CO2Incubator (temperature 37
DEG C, 5 % CO2) in culture, after cell is adherent, it is laggard that first group of addition, 10 μM of viscosity fluorescence probe Mito-V are incubated for half an hour
Row bio-imaging (single photon image: excitation wavelength: 561nm, launch wavelength: 570-620nm；Two photon imaging: excitation wavelength
780nm, launch wavelength: 570-620nm)；Second group is first added 10 μM of viscosity stimulant cobans (Monensin), and 30 minutes
After add 10 μM of viscosity fluorescence probe Mito-V, carry out bio-imaging after being incubated for half an hour；10 μM of viscosity are first added in third group
10 μM of viscosity fluorescence probe Mito-V are added in stimulant nystatin (Nystatin) after 30 minutes, carry out after being incubated for half an hour
Bio-imaging；Imaging results are as shown in Figure 5.Compared by analysis it can be seen that no matter in single photon or in two-photon condition
Under, cell is only sent out faint in the case where only probe light；Added with probe and viscosity stimulant, (coban is made mould
Rhzomorph) in the case where cell issue strong feux rouges；Therefore the probe that can synthesize through the invention of cell of different viscosities into
Row cell imaging is distinguished.
Claims (7)
1. a kind of two-photon viscosity probe for positioning mitochondria, chemical name 1,3,3- trimethyl -2- methylene indoles-tonka-bean
Element, structural formula are as shown in the formula (I):
Formula (I).
2. a kind of synthetic method of two-photon viscosity probe as described in claim 1, which comprises the following steps:
(1) 4- (lignocaine) salicylide and the ethyl acetoacetate heating reflux reaction in ethyl alcohol in the presence of piperidines, separation
Purifying obtains 3- acetyl butylcoumariii；
(2) in protective atmosphere, 3- acetyl butylcoumariii and 1,3,3- trimethyl -2- methylene indoleacetaldehydes in the presence of piperidines in
It is heated to reflux in ethyl alcohol, isolates and purifies to obtain 1,3,3- trimethyl -2- methylene indoles-cumarin.
3. synthetic method according to claim 2, which is characterized in that 4- (lignocaine) salicylide described in step (1):
The molar ratio of ethyl acetoacetate is 1:1-1.3；
3- acetyl butylcoumariii described in step (2): the molar ratio of 1,3,3- trimethyl -2- methylene indoleacetaldehyde is 1:1.
4. synthetic method according to claim 2, which is characterized in that purification procedures described in step (1) are as follows: will be anti-
System after answering is cooled to room temperature, and golden yellow precipitate is precipitated, pure products are obtained after recrystallizing.
5. synthetic method according to claim 2, which is characterized in that in step (1) and (2), reaction temperature is 80 DEG C, instead
It is 12h between seasonable.
6. synthetic method according to claim 2, which is characterized in that purification procedures described in step (2) are as follows: will be anti-
System vacuum distillation after answering is spin-dried for after solvent obtains crude product, obtains purified product through pillar layer separation；The column chromatography point
From mobile phase be preferably volume ratio be 1:50 methanol and methylene chloride.
7. a kind of two-photon viscosity probe as described in claim 1 answering in preparation detection solution and mitochondria viscosity reagents
With.
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| CN112442020A (en) * | 2019-09-03 | 2021-03-05 | 南京大学 | Fluorescent probe capable of tracing mitochondria-lysosome interaction in super-resolution mode |
| CN112939957A (en) * | 2021-02-03 | 2021-06-11 | 山西大学 | Benzoindole derivative In-XY1, and synthesis method and application thereof |
| CN113004276A (en) * | 2021-03-15 | 2021-06-22 | 天津理工大学 | Fluorescent probe for positioning mitochondria and preparation method and application thereof |
| CN113582985A (en) * | 2021-08-25 | 2021-11-02 | 安徽大学 | Mitochondrion targeted pH and viscosity dual-channel detection fluorescent probe and preparation method and application thereof |
| CN113735757A (en) * | 2021-09-30 | 2021-12-03 | 陕西师范大学 | Microenvironment sensitive fluorescent organic small molecule compound and synthetic method and application thereof |
| CN114133387A (en) * | 2021-11-29 | 2022-03-04 | 郑州大学 | Fluorescent probe with viscosity sensing property and capable of targeting multiple organelles |
| CN114891021A (en) * | 2022-05-13 | 2022-08-12 | 天津理工大学 | Fluorescent dye for positioning mitochondria and preparation method thereof |
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| CN112939957A (en) * | 2021-02-03 | 2021-06-11 | 山西大学 | Benzoindole derivative In-XY1, and synthesis method and application thereof |
| CN112939957B (en) * | 2021-02-03 | 2022-09-23 | 山西大学 | Benzoindole derivative In-XY1, and synthesis method and application thereof |
| CN113004276A (en) * | 2021-03-15 | 2021-06-22 | 天津理工大学 | Fluorescent probe for positioning mitochondria and preparation method and application thereof |
| CN113004276B (en) * | 2021-03-15 | 2022-06-03 | 天津理工大学 | Fluorescent probe for positioning mitochondria and preparation method and application thereof |
| CN113582985A (en) * | 2021-08-25 | 2021-11-02 | 安徽大学 | Mitochondrion targeted pH and viscosity dual-channel detection fluorescent probe and preparation method and application thereof |
| CN113735757A (en) * | 2021-09-30 | 2021-12-03 | 陕西师范大学 | Microenvironment sensitive fluorescent organic small molecule compound and synthetic method and application thereof |
| CN113735757B (en) * | 2021-09-30 | 2024-03-15 | 陕西师范大学 | Micro-environment sensitive fluorescent organic small molecular compound and synthetic method and application thereof |
| CN114133387A (en) * | 2021-11-29 | 2022-03-04 | 郑州大学 | Fluorescent probe with viscosity sensing property and capable of targeting multiple organelles |
| CN114891021A (en) * | 2022-05-13 | 2022-08-12 | 天津理工大学 | Fluorescent dye for positioning mitochondria and preparation method thereof |
| CN114891021B (en) * | 2022-05-13 | 2023-09-12 | 天津理工大学 | Fluorescent dye for mitochondrial localization and preparation method thereof |
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Application publication date: 20190802 |