CN106866738B - One kind regulating and controlling H in accurate detection mitochondria by light2S2Fluorescence probe and its preparation method and application - Google Patents
One kind regulating and controlling H in accurate detection mitochondria by light2S2Fluorescence probe and its preparation method and application Download PDFInfo
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
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- 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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- 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
- G01N21/645—Specially adapted constructive features of fluorimeters
- G01N21/6456—Spatial resolved fluorescence measurements; Imaging
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- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
Abstract
The present invention relates to one kind regulating and controlling H in accurate detection mitochondria by light2S2Fluorescence probe and its preparation method and application, belong to organic fluorescence probe field.H2S is the human body gaseous signal molecule that the third after NO and CO is identified, and under the action of ROS, H2S can be converted into H2S2, so H2S2Fluorescence probe has a very important significance.Mito-H2S2The structural formula of fluorescence probe is such as shown in (I).Fluorescence probe of the present invention can accurately detect Intramitochondrial H2S2And avoid intracytoplasmic H2S2Interference, in addition, the probe has the characteristics that preferable Mitochondrially targeted property, chemical stability, bio-compatibility and selectivity.Laser confocal imaging experiment shows that the probe has preferable cell permeability, has no toxic side effect to cell and organism, the detection of subcellsular level reactive oxygen species may be implemented, and further apply the research of neurodegenerative disease and cancer.
Description
Technical field
The present invention relates to one kind regulating and controlling H in accurate detection mitochondria by light2S2Fluorescence probe and preparation method thereof and answer
With belonging to organic fluorescence probe field.
Background technology
Hydrogen sulfide is the human body gaseous signal molecule that the third after NO and CO is identified, in Neurotransmission mistake
Highly important adjustment effect is played in journey.Hydrogen sulfide, which is also found in cardiovascular system, simultaneously also has many important lifes
Function is managed, such as adjusts the diastole, anti-oxidant, inhibition inflammation, reduction metabolic rate of vascular smooth muscle.Hydrogen sulfide levels are different
It is often also believed to closely related with alzheimer's disease, Down's syndrome, diabetes and hepatic sclerosis etc..The physiology of hydrogen sulfide
Have become the hot spot of chemistry and biological study at present with pathology functional study, and develops the sulfurated hydrogen detection of accurate quick
Method becomes one of the key subject in the field.
Since the pKa1 of hydrogen sulfide is about 7.04, deprotonation dissociation can occur for hydrogen sulfide under the conditions of physiology (pH 7.40)
Effect, intracellular H2S and HS-Ratio be about 1: 2 (nH2S∶nHS-).Therefore often with NaHS or Na in document2S is as H2S donors
The research of probe response performance is carried out, similarly uses Na herein2S2As H2S2Donor carries out the research of probe response performance.
Key player of the mitochondria in life promotes it always as the most important thing in scientific research.In mitochondria
Research in, mostly with fluorescence probe master, an ideal fluorescence probe is the dream of numerous scientist, so far it has been reported that going out
Carry out many fluorescence probes, such as detection reactive oxygen species, active nitrogen cluster, metal ion, the fluorescence probe of biological micromolecule etc., still
These fluorescence probes all have the shortcomings that one it is fatal be exactly by cytoplasm targetted mitochondria during be avoided that come
From the interference of intracytoplasmic detected material, result of study is caused to lack persuasion.In order to solve the problems, such as that this exists for a long time,
It is badly in need of researching and developing a kind of fluorescence probe that can be positioned mitochondria and be avoided that detected material in cytoplasm again.
Invention content
Present invention solves the technical problem that being：It proposes that one kind can position living cells Mitochondria, and is regulated and controled accurately by light
Detect H in mitochondria2S2Fluorescence probe and its preparation method and application.
In order to solve the above-mentioned technical problem, technical solution proposed by the present invention is：One kind regulating and controlling accurate detection line by light
H in plastochondria2S2Fluorescence probe, which is characterized in that the fluorescence probe be Mito-H2S2Fluorescence probe, Mito-H2S2Fluorescence
The structural formula of probe is such as shown in (I)：
In order to solve the above-mentioned technical problem, technical solution proposed by the present invention is：Described regulates and controls accurate detection by light
Intramitochondrial H2S2Mito-H described in the preparation method of fluorescence probe2S2The preparation method of fluorescence probe includes the following steps：
Fluorescein derivative compound and 4- nitrine butyl triphenyl phosphines are added sequentially in acetonitrile, stirring at normal temperature 8-12h, it is cooling to take out
Filter removes solvent, purifies to obtain target product Mito-H through silica gel column chromatography2S2Fluorescence probe, reaction equation are as follows：
Preferably, the molar ratio of the fluorescein derivative compound and 4- nitrine butyl triphenyl phosphines is 0.8-1:1.
Preferably, the preparation method of the fluorescein derivative is as follows：
(1) fluorescein is dissolved in n,N-Dimethylformamide DMF, K is then added2CO3With bromopropyl alkynes, wherein bromine
Propyl alkynes has 80% volume ratio in toluene, then bromopropyl alkynes stirs 1-3h at 60 DEG C, waters down reaction mixing with water
Object, then extraction are spin-dried for, purify to obtain fluorescein list propargyl bromide by plastic column chromatography,
(2) (3- dimethyl propylamines) carbodiimide of 1- ethyls -3 EDCI is added in dichloromethane in ice bath, is then added
Enter light blocking group and 4-dimethylaminopyridine DMAP stirring 10-30min, fluorescein list propargyl bromide is eventually adding, and stirs 20-
Then 28h is filtered, rinsed with dichloromethane, and filtrate is selected dry, then purifies to obtain light protection fluorescein list through silica gel column chromatography
Propargyl bromide.
Preferably, the molar ratio of fluorescein and bromopropyl alkynes is 1 in the step (1):1-1.2, bromopropyl alkynes cannot
Excessively, it will produce excessive miscellaneous point.
Preferably, fluorescein list propargyl bromide in the step (2), light blocking group molar ratio be 1:1-1.3 wherein noting
The carboxyl of meaning light blocking group pays attention to activating, and is conducive to the yield of light protection fluorescein list propargyl bromide.
In order to solve the above-mentioned technical problem, technical solution proposed by the present invention is：Described regulates and controls accurate detection by light
H in mitochondria2S2The application of fluorescence probe, the fluorescence probe can be applied in physiological systems accurately detect Intramitochondrial
H2S2。
Beneficial effects of the present invention：
The fluorescence probe of the present invention has preferable Mitochondrially targeted property, chemical stability, bio-compatibility and H2S2Choosing
Selecting property.Laser confocal imaging experiment shows that the probe has preferable cell permeability, secondary work nontoxic to cell and organism
With.
The fluorescence probe of the present invention accurately detects Intramitochondrial H in it can be applied to cell system by light regulation and control2S2
And it avoids from H in cytoplasm2S2Interference application.
H in the accurate survey line plastochondria of the present invention2S2Fluorescence probe can be used for living cells mitochondria H2S2Accurate detection,
Living cells mainly is Hela cell strains.
Laser confocal imaging experiment shows that the probe has preferable cell permeability, to cell and the nontoxic pair of organism
Effect, may be implemented the detection of subcellsular level reactive oxygen species, and further apply neurodegenerative disease and cancer
Research.
Description of the drawings
The present invention is described further below in conjunction with the accompanying drawings.
Fig. 1 is Mito-H prepared by embodiment 12S2(10uM) is after UV illumination 150 seconds to the Na of 40um2S2Concentration
The fluorescence spectra of the different response times of the buffer solution of PBS.
Fig. 2 is Mito-H prepared by embodiment 12S2To the slow of the PBS of the various ions of 100um after (10uM) illumination 150 seconds
Rush the fluorescence spectra of the response of solution.
Fig. 3 is Mito-H prepared by embodiment 12S2The confocal microscopic image of (10uM) in cell mitochondrial.
Specific implementation mode
Embodiment 1
Regulate and control H in accurate detection mitochondria by light2S2Fluorescence probe preparation method it is as follows：
(1) 0.8g fluoresceins are dissolved in n,N-Dimethylformamide DMF, the K of 0.93g is then added2CO3With
The bromopropyl alkynes of 0.18ml, wherein bromopropyl alkynes have 80% volume ratio in toluene, then stir 1h at 60 DEG C, use water
Reaction mixture is watered down, then extraction is spin-dried for, and purifies to obtain fluorescein list propargyl bromide through silica gel column chromatography.1H NMR(300MHz,
CDCl3):δ 10.14 (s, 1H), 8.02 (t, J=6Hz, 1H), 7.82 (t, J=7.5Hz, 1H), 7.75 (t, J=7.5Hz,
1H), 7.30 (d, J=6Hz, 1H), 7.01 (d, J=3Hz, 1H), 6.74 (m, 3H) 6.58 (s, 1H), 4.89 (d, J=
1.5Hz, 2H), 3.62 (d, J=1.5Hz, 1H).
(2) the n,N-Dimethylformamide EDCI of 106mg is added in the dichloromethane of 10ml in ice bath, is then added
The light blocking group of 193.9mg and the 4-dimethylaminopyridine DMAP of 7mg stir 10min, the fluorescein list propargyl bromide of 250mg
It is eventually adding stirring 22h, then filters, is rinsed with dichloromethane, filtrate is selected dry, then purifies to obtain light through silica gel column chromatography
Protect fluorescein list propargyl bromide.1H NMR(300MHz,CDCl3):δ 8.07 (t, J=7.5Hz, 2H), 7.96 (d, J=4.5Hz,
1H),7.71(dd, J1=3.8Hz, J2=7.5Hz, 2H), 7.59 (t, J=7.9Hz, 1H), 7.35 (m, 5H), 7.19 (d, J=
7.2Hz, 1H), 7.10 (s, 1H), 6.89 (s, 1H), 6.80 (s, 2H), 6.76 (t, J=5.7Hz, 2H), 5.07 (s, 2H),
4.74 (s, 2H), 4.84 (s, 2H), 3.65 (d, J=1.5Hz, 1H).
(3) the 4- nitrine butyl triphenyl phosphines of the fluorescein derivative compound of 71.11mg and 50mg are added sequentially to 3ml
Acetonitrile in, stirring at normal temperature 8 hours is cooling to filter, and removes solvent, purifies to obtain target product Mito-H through silica gel column chromatography2S2
Fluorescence probe, 1H NMR (300MHz, CDCl3):δ 8.25 (t, J=4.5Hz, 2H), 8.16 (d, J=4.5Hz, 1H), 8.07
(d, J=4.5Hz, 1H), 7.90 (m, 3H), 7.84 (m, 14H), 7.36 (t, J=1.8Hz, 2H), 7.31 (dd, J1=
4.5Hz,J2=3.9Hz, 3H), 7.26 (t, J=4.0Hz, 3H), 7.15 (d, J=1.5Hz, 1H), 7.07 (dd, J1=
2.6Hz,J2=2.6Hz, 1H), 6.91 (d, J=5Hz, 1H), 6.84 (dd, J1=2.7Hz, J2=2.7Hz, 1H), 6.76 (d,
J=5.1Hz, 1H), 5.24 (s, 2H), 4.99 (s, 2H), 4.45 (s, 4H), 2.03 (m, 2H), 1.60 (m, 2H), 1.53 (m,
2H)。
Embodiment 2
Regulate and control H in accurate survey line plastochondria by light2S2Fluorescence probe preparation method it is as follows：
(1) 1g fluoresceins are dissolved in the n,N-Dimethylformamide DMF solution of 4.5ml, are then added 1.16g's
K2CO3With the bromopropyl alkynes of 0.244ml, wherein bromopropyl alkynes has 80% volume ratio in toluene, is then stirred at 60 DEG C
3h waters down anti-a with water and answers mixture, and then extraction is spin-dried for, and purifies to obtain fluorescein list propargyl bromide through silica gel column chromatography；
(2) the n,N-Dimethylformamide EDCI of 53.75mg is added in the dichloromethane of 5ml in ice bath, is then added
Enter the light blocking group of 114mg and the 4-dimethylaminopyridine DMAP stirring 20min of 3.42mg, the fluorescein list bromine third of 128mg
Alkynes is eventually adding stirring 26h, then filters, is rinsed with dichloromethane, and filtrate is selected dry, then purifies to obtain through silica gel column chromatography
Light protects fluorescein list propargyl bromide.
(3) the 4- nitrine butyl triphenyl phosphines of the fluorescein derivative compound of 156.8mg and 100mg are added sequentially to
In the acetonitrile of 4ml, stirring at normal temperature 10 hours is cooling to filter, and removes solvent, purifies to obtain target product through silica gel column chromatography
Mito-H2S2Fluorescence probe.
Embodiment 3
Regulate and control H in accurate survey line plastochondria by light2S2Fluorescence probe preparation method it is as follows：
(1) 1.8g fluoresceins are dissolved in the n,N-Dimethylformamide DMF solution of 9ml, are then added 2.33g's
K2CO3With the bromopropyl alkynes of 0.455ml, wherein bromopropyl alkynes has 80% volume ratio in toluene, is then stirred at 60 DEG C
4h waters down reaction mixture with water, and then extraction is spin-dried for, and purifies to obtain fluorescein list propargyl bromide through silica gel column chromatography；
(2) the n,N-Dimethylformamide EDCI of 107.5mg is added in the dichloromethane of 10ml in ice bath, is then added
Enter the light blocking group of 236mg and the 4-dimethylaminopyridine DMAP stirring 30min of 6.85mg, the fluorescein list of 249.06mg
Propargyl bromide is eventually adding stirring 20h, then filters, is rinsed with dichloromethane, and filtrate is selected dry, is then purified through silica gel column chromatography
Obtain light protection fluorescein list propargyl bromide.
(3) the 4- nitrine butyl triphenyl phosphines of the fluorescein derivative compound of 400mg and 225mg are added sequentially to 10ml
Acetonitrile in, stirring at normal temperature 11 hours is cooling to filter, and removes solvent, purifies to obtain target product Mito- through silica gel column chromatography
H2S2Fluorescence probe.
Embodiment 4
Regulate and control H in accurate survey line plastochondria by light2S2Fluorescence probe preparation method it is as follows：
(1) 8.6g fluoresceins are dissolved in the n,N-Dimethylformamide DMF solution of 45ml, are then added 11.65g's
K2CO3With the bromopropyl alkynes of 2.4ml, wherein bromopropyl alkynes has 80% volume ratio in toluene, then stirs 4h at 60 DEG C,
Reaction mixture is watered down with water, then extraction is spin-dried for, and purifies to obtain fluorescein list propargyl bromide through silica gel column chromatography；
(2) the n,N-Dimethylformamide EDCI of 537.5mg is added in the dichloromethane of 50ml in ice bath, is then added
Enter the light blocking group of 1246mg and the 4-dimethylaminopyridine DMAP stirring 25min of 34mg, the fluorescein list bromine third of 1236mg
Alkynes is eventually adding stirring 28h, then filters, is rinsed with dichloromethane, filtrate is spin-dried for, and then purifies to obtain through silica gel column chromatography
Light protects fluorescein list propargyl bromide；
(3) the 4- nitrine butyl triphenyl phosphines of the fluorescein derivative compound of 1.56g and 1g are added sequentially to 30ml's
In acetonitrile, stirring at normal temperature 12 hours is cooling to filter, and removes solvent, purifies to obtain target product Mito-H through silica gel column chromatography2S2
Fluorescence probe.
Embodiment 5
Regulate and control H in accurate survey line plastochondria by light2S2Fluorescence probe to H2S2Response detection：
1、Mito-H2S2To 10 equivalent Na2S2The fluorescence response (Fig. 1) of different response times：
With buffer preparation 10uM Mito-H2S2H2S2After UV illumination 150 seconds, 10 equivalents are added in probe
Na2S2, test response 60 minutes, 80 minutes, 100 minutes, 120 minutes fluorescence intensities respectively with fluorescence spectrophotometry, and
Draw Mito-H2S2To the Na of 4 equivalents2S2The fluorescence spectra of different response times.As a result it describes：Here illustrate Mito-H2S2
Probe respond again 120 minutes after can reach the maximum value of reaction.
2、Mito-H2S2To the fluorescence response (Fig. 2) of 10 equivalent different metal ions：
With buffer preparation 10uM Mito-H2S2H2S2After UV illumination 150 seconds, the difference of 10 equivalents is added in probe
Metal ion is tested with fluorescence spectrophotometry, and draws Mito-H respectively2S2Na2S2Probe is to the glimmering of different metal ions
Light spectrogram.As a result it describes：Here illustrate Mito-H2S2Probe to removing Na2S2There is response outer, other ions are not all rung
It answers, illustrates our probe to H2S2High degree of specificity.
3、Mito-H2S2Confocal microscopic image (Fig. 3) in cell mitochondrial：
Add Mito-H into the culture dish containing Hela cells2S2DMSO solution after mixing with cell culture fluid makes
Mito-H2S2A concentration of 5uM in culture solution after dyeing 2 hours, is rinsed 3 times, by this with the buffer solution of pH=7.35
Culture dish is imaged under Laser Scanning Confocal Microscope, takes out culture dish, after UV illumination 150 seconds, 1 hour is stood, again by the culture
Ware is imaged under Laser Scanning Confocal Microscope.As a result it describes：(1) be the light field figure for having cell, (2) be have cell only plus probe H-1
Dark field plot, (3) are the dark field plots for having cell plus probe H-1 and illumination 150 seconds, (4) be have cell plus probe H-1 and
Na2S2Dark field plot, (5) are that have cell plus probe H-1 and Na2S2, and the dark field plot of illumination 150 seconds can be with from several figures
It was found that probe is only in illumination condition and Na2S2Under the conditions of existing for all, just it may be implemented to Na2S2Detection, it is thus real
Showed light it is controllable to Na in mitochondria2S2Detection, and avoid Na in cytoplasm2S2Influence.
The present invention's is not limited to the above embodiment the specific technical solution, all technologies formed using equivalent replacement
Scheme be the present invention claims protection domain.
Claims (3)
1. a kind of regulating and controlling H in accurate detection mitochondria by light2S2Fluorescence probe, which is characterized in that the fluorescence probe is
Mito-H2S2Fluorescence probe, Mito-H2S2The structural formula of fluorescence probe is such as shown in (I)：
2. a kind of accurately detecting Intramitochondrial H by light regulation and control as described in claim 12S2The preparation method of fluorescence probe,
It is characterized in that, the Mito-H2S2The preparation method of fluorescence probe includes the following steps：By fluorescein derivative compound and
4- nitrine butyl triphenyl phosphorus is added sequentially in acetonitrile, stirring at normal temperature 8-12h, cooling to filter, and solvent is removed, through silica gel column layer
Analysis purification obtains target product Mito-H2S2Fluorescence probe, reaction equation are as follows：
3. according to claim 2 regulate and control H in accurate detection mitochondria by light2S2The preparation method of fluorescence probe, it is special
Sign is that the molar ratio of the fluorescein derivative compound and 4- nitrine butyl triphenyl phosphorus is 0.8-1:1.
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| "Capture and Visualization of Hydrogen Sulfide by a Fluorescent Probe";Chunrong Liu,et al.;《Angew. Chem.》;20110906;第123卷;第10511-10513页 * |
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