CN106496102A - A kind of mitochondrion two-photon fluorescence viscosity probe and preparation method thereof - Google Patents
A kind of mitochondrion two-photon fluorescence viscosity probe and preparation method thereof Download PDFInfo
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Abstract
The invention discloses a kind of mitochondrion two-photon fluorescence viscosity probe and preparation method thereof, the structural formula of its Mitochondria two-photon fluorescence viscosity probe is：Target molecule of the present invention has good cellular affinity, can carry out the two photon imaging of long-time stable to living cells mitochondria, and can recognize mitochondrion viscosity B coefficent.Effective visualization tool is provided for tracking change of the mitochondrion in cell, with good development and application values.
Description
Technical field
The present invention relates to a kind of mitochondrion two-photon fluorescence viscosity probe and preparation method thereof, be a kind of have avirulence,
Identification single-minded to cell mitochondrial and the good two-photon absorbing material vinylpyridine nitric acid salt derivative of light stability.
Background technology
Mitochondrion (Mitochondria) is the key cells device of cell survival, produces the energy of the somagenic need more than 90%
Amount is grown with sustaining life and supporting, in many important physiological process, such as apoptosis, differentiation, signal transduction and activity
Indispensable effect is played in the generation of oxygen (ROS).In the different phase of cell division and metabolism and in cell development
In atomization, mitochondrial size, quantity and form can all occur different changes.Work in recent years it has been shown that
Mitochondrial form and quantity, such as neurodegenerative disease parkinson (Parkinson ' s related to numerous disease
Disease), A Zihaimoshi diseases (Alzheimer ' s disease), atherosclerosiss, heart disease, apoplexy and cancer, its
In be mainly shown as that the viscosity that shown by mitochondrial swelling increases.Therefore, by imaging in fluorescent probe observation living cells
Mitochondrial metamorphosis, understand effect of the mitochondrion in bio-metabolic process, have in terms of disease early diagnosis and therapy
There is directive significance.
However, the organic molecule mitochondrial probe that has commercially produced at present, is by fluorescence and phosphorescence skill mostly
Art carries out imaging analysis, such as Rhodamine123, Mito to mitochondrion quantity and formGreenFM and MitoRed FM, they are broadly divided into the mitochondrion of the fluorescent probe and dependent/non-dependent that depend on mitochondrial membrane potential
Probe, although these dyestuffs can carry out living cells imaging, but their cytotoxicity is big, photo-labile, poorly water-soluble,
Stokes displacements are less, it is impossible to the mitochondrion viscosity increase produced because of disease is identified, so as to limit making for they
With.Therefore, develop the high mitochondrion fluorescent probe of a kind of nontoxic, good water solubility, light stability have important scientific meaning and
Obvious application prospect.
Applicant has carried out following literature search to the theme of the application：
1st, scholar.glgoo.org nets retrieval result：(2016/9/29)
2nd, middle National IP Network's retrieval result：
Retrieval mode one：
Piece name-mitochondrion two-photon fluorescence viscosity probe：Without pertinent literature.
A kind of piece name-mitochondrion two-photon fluorescence viscosity probe vinylpyridine nitric acid salt derivative and its preparation side
Method：Without pertinent literature.
Retrieval mode two：
In full-mitochondrion two-photon fluorescence viscosity probe：Without pertinent literature.
A kind of in full-mitochondrion two-photon fluorescence viscosity probe vinylpyridine nitric acid salt derivative and its preparation side
Method：Without pertinent literature.
Content of the invention
The present invention is intended to provide a kind of mitochondrion two-photon fluorescence viscosity probe and preparation method thereof, is with iodomethane, first
Yl pyridines, dimethyl hydroxyethyl amine, 4-Fluorobenzaldehyde are raw material, have simply efficiently synthesized organic pyridine nitric acid of D- π-A configurations
Salt.Target molecule of the present invention has good cellular affinity, can carry out double light of long-time stable to living cells mitochondria
Son imaging, and mitochondrion viscosity B coefficent can be recognized.Effective visualization tool is provided for tracking change of the mitochondrion in cell,
There are good development and application values.
Mitochondrion two-photon fluorescence viscosity probe of the present invention is vinylpyridine nitric acid salt derivative, and its structural formula is：
The preparation method of mitochondrion two-photon fluorescence viscosity probe of the present invention, comprises the steps：
1st, the synthesis of intermediate 1
Iodomethane (14.40g, 100mmol) is added in 50mL round-bottomed flasks, is slowly dropped under stirring and is dissolved in 4mL ethanol
4-methyl pyridine (6.20g, 65mmol), be heated to back flow reaction 20min, separate out a large amount of white crystals, filter, washing with alcohol
And after drying, obtain intermediate 1,14.60g, yield 96%.
2nd, the synthesis of intermediate 2
DMSO (200mL), dimethyl hydroxyethyl amine (165g, 2200mmol), Carbon Dioxide is added in 500mL round-bottomed flasks
Potassium (166g, 1200mmol) and 3 drop Aliquat-336, are warming up to 95 DEG C of reaction 10min, add 4-Fluorobenzaldehyde
(124g, 1000mmol), continues reaction three days at 95 DEG C；Reaction is cooled to room temperature after terminating, and reactant liquor is poured in frozen water, uses
Salt acid for adjusting pH value collects water layer to 2, after being stirred vigorously, with NaOH solution regulation pH value to 11, collected organic layer, repeatable operation
3 times, extracted with DCM and collect organic faciess, add anhydrous magnesium sulfate to dry, intermediate 2 is obtained after removing solvent, be faint yellow solid,
142g, yield 79%.
3rd, the synthesis of target product B1
Intermediate 2 (1.80g, 10mmol), intermediate 1 (2.40g, 20mmol), 30mL is added in 100mL round-bottomed flasks
Dehydrated alcohol and 3 drop piperidines, stirring reaction 24h at 60 DEG C obtain dark red solution；To in the dark red solution, Deca contains
AgNO3The 30mL ethanol solutions of (1.70g, 10mmol), back flow reaction 2h, reaction are cooled down after terminating, and are filtered, washing with alcohol
And dry, then DCM recrystallization are used, there are red crystals to separate out, obtain target product 2.00g, yield 60%.
4th, the bio-imaging research of target molecule B1 of the present invention
In living cells co-focusing imaging, the target molecule B1 and human hepatocarcinoma cells HepG2 of low concentration (1-10 μm of ol)
After the co-cultivation of 10 minutes, PBS buffer solution is cleaned 2-3 time, then the Mitotracker Far Red cultures 10 with 500nM
Minute.By two-photon laser confocal microscopy, target molecule and mitochondrion commercial dyes Mitotracker are found
Far Red are overlapped well, and there is the effect for responding that mitochondrion viscosity (viscosity) changes.
Compared with the prior art, beneficial effects of the present invention are embodied in：
1st, the vinylpyridine nitrate B1 of present invention synthesis is that a kind of two-photon absorption with biological developing function has
Machine small molecule material, is capable of identify that the change of active somatic cell Mitochondria viscosity, can be used as mitochondrion two-photon fluorescence viscosity
Probe；
2nd, compared with document report or commercial dye, the target product B1 of the present invention has two-photon absorption feature, to thin
The features such as born of the same parents' not damaged, good water solubility, high light stability, and there is obvious using value；
3rd, target product B1 of the invention single-minded can develop to mitochondrion, and its extremely low cytotoxicity and
High light stability is applicable to long-time and follows the trail of form and viscosity B coefficent of the mitochondrion in living cells.
4th, target product B1 of the invention is the new mitochondrial dye of a class.
5th, the raw material of target product B1 of the invention be easy to get, synthetic route brief, synthesis condition is gentle.
Description of the drawings
Fig. 1 is the crystal structure figure of target product B1 of the present invention, illustrates that B1 is the novel substance for having clear and definite structure.
Fig. 2 is the water solublity test of target product B1 of the present invention, illustrates that B1 has excellent water solublity.
Fig. 3 is real-time monitoring results of the target product B1 of the present invention to the cell proliferation activity influence of HepG-2 and 3T3, table
Bright B1 to two kinds of cytotoxics, with good biocompatibility.
Fig. 4 is that the single, double photon of target product B1 of the present invention develops and 3D images, (a) single photon (b) two-photon (c)
Overlay chart (d) three-dimensional imaging, shows that B1 can enter intracellular and with the development of single, double photon function.
Fig. 5 is the development figure of target product B1 of the present invention and commercial dyes Mitotracker Far Red common locations,
Pearson ' s Rr=0.8921 illustrate that B1 has overlapping for height with commercial dyes MTFR.
Fig. 6 is development figure and intracellular Fluorescence imaging region of the target product B1 of the present invention in HepG-2 cell Mitochondrias
Microviscosity Gradient distribution image, show that B1 has response mitochondrion viscosity (viscosity) effect that changes.
Fig. 7 is microviscosity Gradient distribution images of the target product B1 of the present invention to the imaging region of variety classes cell, says
Bright B1 can be with a wide range of applications as mitochondrion two-photon fluorescence viscosity probe.
Fig. 8 is the development detected to cell in 0-72h by target product B1 of the present invention, illustrates that the chemical combination object light is steady
Qualitative height, can be used for long-time and the mitochondrion of living cells is tracked.
Specific embodiment
The preparation of the present embodiment Mitochondria two-photon fluorescence viscosity probe and biological developing method are as follows：
1st, the synthesis of intermediate 1
Iodomethane (14.40g, 100mmol) is added in 50mL round-bottomed flasks, is slowly dropped under stirring and is dissolved in 4mL ethanol
4-methyl pyridine (6.20g, 65mmol), be heated to 78 DEG C of back flow reaction 20min, separate out a large amount of white crystals, filter, ethanol
Intermediate 1,14.60g, yield 96% is obtained after washing and drying.
2nd, the synthesis of intermediate 2
DMSO (200mL), dimethyl hydroxyethyl amine (165g, 2200mmol), Carbon Dioxide is added in 500mL round-bottomed flasks
Potassium (166g, 1200mmol) and 3 drop Aliquat-336, are warming up to 95 DEG C of reaction 10min, add 4-Fluorobenzaldehyde
(124g, 1000mmol), continues reaction three days at 95 DEG C；Reaction is cooled to room temperature after terminating, and reactant liquor is poured in frozen water, uses
Salt acid for adjusting pH value collects water layer to 2, after being stirred vigorously, with NaOH solution regulation pH value to 11, collected organic layer, repeatable operation
3 times, extracted with DCM and collect organic faciess, add anhydrous magnesium sulfate to dry, intermediate 2 is obtained after removing solvent, be faint yellow solid,
142g, yield 79%.
3rd, the synthesis of target product
Intermediate 2 (1.80g, 10mmol), intermediate 1 (2.40g, 20mmol), 30mL is added in 100mL round-bottomed flasks
Dehydrated alcohol and 3 drop piperidines, are heated to 60 DEG C of stirring reactions 24h, obtain dark red solution；To in the dark red solution, Deca contains
There is AgNO3The 30mL ethanol solutions of (1.70g, 10mmol), back flow reaction 2h, reaction are cooled down after terminating, and are filtered, and ethanol is washed
Wash and dry, then use DCM recrystallization, there are red crystals to separate out, obtain target product 2.00g, yield 60%.
1H NMR(400MHz,d6- DMSO) δ=8.67 (d, 2H), 8.02 (d, 2H), 7.89 (d, 1H), 7.56 (d, 2H),
7.14(d,1H),6.79(d,2H),4.76(s,1H),4.17(s,3H),3.53(d,4H),3.03(d,3H).
13C NMR(101MHz,d6- DMSO) δ=153.34,151.06,144.25,141.38,130.20,122.04,
116.77,111.67,58.14,53.83,46.25,38.70.
Anal.Calcd.for C17H21N3O4:C,61.62；H,6.39；N, 12.68%.Found:C,56.08；H,
7.052；N, 11.64%.IR (KBr, cm-1):3390(m),2925(w),1640(m),1584(s),1518(s),1377(vs),
1176(s),1040(w),818(w),535(m).
M.p.=120 DEG C of .ESI:m/z,cal:269.36,found:269.42[M+]
4th, the bio-imaging research of target molecule B1 of the present invention
In living cells co-focusing imaging, the target molecule B1 and human hepatocarcinoma cells HepG2 of low concentration (1-10 μm of ol)
After the co-cultivation of 10 minutes, PBS buffer solution is cleaned 2-3 time, then the Mitotracker Far Red cultures 10 with 500nM
Minute.By two-photon laser confocal microscopy, target molecule and mitochondrion commercial dyes Mitotracker are found
Far Red are overlapped well, and there is the effect for responding that mitochondrion viscosity (viscosity) changes.
Claims (2)
1. a kind of mitochondrion two-photon fluorescence viscosity probe, it is characterised in that its structural formula is：
2. the preparation method of the mitochondrion two-photon fluorescence viscosity probe described in a kind of claim 1, it is characterised in that include as
Lower step：
(1) synthesis of intermediate 1
Iodomethane 100mmol is added in 50mL round-bottomed flasks, and the 65mmol for being dissolved in 4mL ethanol is slowly added dropwise under stirring to methyl
Pyridine, is heated to back flow reaction 20min, separates out a large amount of white crystals, filters, and obtains intermediate 1 after washing with alcohol drying；
(2) synthesis of intermediate 2
To in 500mL round-bottomed flasks add DMSO 200mL, dimethyl hydroxyethyl amine 2200mmol, Anhydrous potassium carbonate 1200mmol with
And 3 drop Aliquat-336, be warming up to 95 DEG C reaction 10min, add 4-Fluorobenzaldehyde 1000mmol, at 95 DEG C continue reaction
Three days；Reaction is cooled to room temperature after terminating, and reactant liquor is poured in frozen water, with salt acid for adjusting pH value to 2, collects water after stirring
Layer, adjusts pH value to 11 with NaOH solution, and collected organic layer collects organic faciess with DCM extractions, adds anhydrous magnesium sulfate to dry,
Intermediate 2 is obtained after removing solvent；
(3) synthesis of target product B1
2 10mmol of intermediate, 1 20mmol, 30mL dehydrated alcohol of intermediate and 3 drop piperidines are added in 100mL round-bottomed flasks,
Stirring reaction 24h at 60 DEG C, obtains dark red solution；To in the dark red solution, Deca contains 10mmol AgNO330mL without
Hydrous ethanol solution, back flow reaction 2h, reaction are cooled down after terminating, and are filtered, and washing with alcohol is simultaneously dried, then use DCM recrystallization, has redness
Crystal is separated out, and obtains target product.
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Cited By (4)
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| CN107382991A (en) * | 2017-08-08 | 2017-11-24 | 安徽大学 | Two-photon fluorescence material benzoxazolyl pyridiniujm and its preparation method and application |
| CN107987014A (en) * | 2017-12-13 | 2018-05-04 | 安徽大学 | A kind of pyridine-sulfonic acid inner salt compound and its preparation method and application |
| CN110885327A (en) * | 2019-11-20 | 2020-03-17 | 浙江工业大学 | Hypochlorous acid rapid response fluorescent probe and preparation method and application thereof |
| CN113711033A (en) * | 2019-05-14 | 2021-11-26 | 哈希公司 | Ultra low range chlorine measurement |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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| CN107987014A (en) * | 2017-12-13 | 2018-05-04 | 安徽大学 | A kind of pyridine-sulfonic acid inner salt compound and its preparation method and application |
| CN107987014B (en) * | 2017-12-13 | 2021-02-09 | 安徽大学 | Pyridine sulfonic acid inner salt compound and preparation method and application thereof |
| CN113711033A (en) * | 2019-05-14 | 2021-11-26 | 哈希公司 | Ultra low range chlorine measurement |
| CN113711033B (en) * | 2019-05-14 | 2023-09-01 | 哈希公司 | Ultra Low Range Chlorine Measurement |
| CN110885327A (en) * | 2019-11-20 | 2020-03-17 | 浙江工业大学 | Hypochlorous acid rapid response fluorescent probe and preparation method and application thereof |
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