CN106496102B - A kind of mitochondria two-photon fluorescence viscosity probe and preparation method thereof - Google Patents
A kind of mitochondria two-photon fluorescence viscosity probe and preparation method thereof Download PDFInfo
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Abstract
The invention discloses a kind of mitochondria two-photon fluorescence viscosity probe and preparation method thereof, the structural formulas of Mitochondria two-photon fluorescence viscosity probe are as follows:
Description
Technical field
The present invention relates to a kind of mitochondria two-photon fluorescence viscosity probe and preparation method thereof, be it is a kind of have it is non-toxic,
Identification single-minded to cell mitochondrial and the good two-photon absorbing material of photostability --- vinylpyridine nitric acid salt derivative.
Background technique
Mitochondria (Mitochondria) is the key cells device of cell survival, and generation is more than the energy of 90% somagenic need
Amount is grown with sustaining life and supporting, in many important physiology courses, 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, different variations can all occur for size, quantity and the form of mitochondria.Work in recent years it has been shown that
The form and quantity of mitochondria, it is related to many diseases, such as neurodegenerative disease Parkinson's disease (Parkinson ' s
Disease), A Zihaimoshi sick (Alzheimer ' s disease), atherosclerosis, heart disease, apoplexy and cancer,
In be mainly shown as that the viscosity that is shown by mitochondrial swelling increases.Therefore, it observes in living cells and is imaged by fluorescence probe
The metamorphosis of mitochondria understands effect of the mitochondria in bio-metabolic process, has in terms of disease early diagnosis and therapy
There is directive significance.
However, the small organic molecule mitochondrial probe commercially produced at present, is by fluorescence and phosphorescence skill mostly
Art carries out imaging analysis, such as Rhodamine123, Mito to mitochondria quantity and formGreenFM and MitoRed FM, they are broadly divided into visits dependent on the fluorescence probe of mitochondrial membrane potential and the mitochondria of dependent/non-dependent
Needle, although these dyestuffs are able to carry out living cells imaging, their cytotoxicity is big, photo-labile, poorly water-soluble,
Stokes displacement is smaller, cannot identify to the mitochondria viscosity increase generated by disease, to limit making for they
With.Therefore, develop the high mitochondria fluorescence probe of a kind of nontoxic, good water solubility, photostability have important scientific meaning and
Apparent application prospect.
Applicant has carried out following literature search to the theme of the application:
1, scholar.glgoo.org net search result: (2016/9/29)
2, middle National IP Network's search result:
Retrieval mode one:
Piece name-mitochondria two-photon fluorescence viscosity probe: without pertinent literature.
A piece a kind of mitochondria two-photon fluorescence viscosity probe of name---- vinylpyridine nitric acid salt derivative and its preparation side
Method: without pertinent literature.
Retrieval mode two:
In full-mitochondria two-photon fluorescence viscosity probe: without pertinent literature.
In full-a kind of mitochondria two-photon fluorescence viscosity probe --- vinylpyridine nitric acid salt derivative and its preparation side
Method: without pertinent literature.
Summary of the invention
The present invention is intended to provide a kind of mitochondria two-photon fluorescence viscosity probe and preparation method thereof, is with iodomethane, first
Yl pyridines, dimethyl hydroxyethyl amine, 4-Fluorobenzaldehyde are raw material, and what is be simple and efficient has synthesized organic pyridine nitric acid of D- π-A configuration
Salt.Target molecule of the present invention has good cellular affinity, and double light of long-time stable can be carried out to living cells mitochondria
Son imaging, and can identify mitochondria viscosity change.Effective visualization tool is provided for variation of the tracking mitochondria in cell,
With good development and application values.
Mitochondria two-photon fluorescence viscosity probe of the present invention is vinylpyridine nitric acid salt derivative, structural formula are as follows:
The preparation method of mitochondria two-photon fluorescence viscosity probe of the present invention, includes the following steps:
1, the synthesis of intermediate 1
Iodomethane (14.40g, 100mmol) is added into 50mL round-bottomed flask, is slowly dropped under stirring and is dissolved in 4mL ethyl alcohol
4-methyl pyridine (6.20g, 65mmol), be heated to back flow reaction 20min, a large amount of white crystals be precipitated, filter, ethanol washing
And intermediate 1,14.60g, yield 96% are obtained after drying.
2, the synthesis of intermediate 2
DMSO (200mL), dimethyl hydroxyethyl amine (165g, 2200mmol), Carbon Dioxide are added into 500mL round-bottomed flask
Potassium (166g, 1200mmol) and 3 drop Aliquat-336, are warming up to 95 DEG C of reaction 10min, add 4-Fluorobenzaldehyde
(124g, 1000mmol), the reaction was continued three days at 95 DEG C；It is cooled to room temperature after reaction, reaction solution is poured into ice water, use
Salt acid for adjusting pH value collects water layer after being vigorously stirred, adjusts pH value to 11 with NaOH solution, collected organic layer operates repeatedly to 2
3 time, organic phase is collected with DCM extraction, anhydrous magnesium sulfate drying is added, obtains intermediate 2 after removing solvent, is faint yellow solid,
142g, yield 79%.
3, the synthesis of target product B1
Intermediate 2 (1.80g, 10mmol), intermediate 1 (2.40g, 20mmol), 30mL are added into 100mL round-bottomed flask
Dehydrated alcohol and 3 drips piperidines, is stirred to react for 24 hours at 60 DEG C, obtains dark red solution；It is added dropwise and contains into the dark red solution
AgNO3The 30mL ethanol solution of (1.70g, 10mmol), back flow reaction 2h are cooled down after reaction, filtering, ethanol washing
And it is dry, then recrystallized with DCM, there is red crystals precipitation, obtains target product 2.00g, yield 60%.
4, 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 co-cultivation in 10 minutes, PBS buffer solution is cleaned 2-3 times, then cultivates 10 with the Mitotracker Far Red of 500nM
Minute.By two-photon laser confocal microscopy, target molecule and mitochondria commercial dyes Mitotracker are found
Far Red is overlapped well, and has the function of responding mitochondria viscosity (viscosity) variation.
Compared with the prior art, the beneficial effects of the present invention are embodied in:
1, the vinylpyridine nitrate B1 that synthesizes of the present invention is that a kind of two-photon absorption with biological developing function has
Machine small molecule material can identify the variation of active somatic cell Mitochondria viscosity, can be used as mitochondria two-photon fluorescence viscosity
Probe；
2, compared with document report or commercial dye, target product B1 of the invention has two-photon absorption feature, to thin
The features such as born of the same parents are not damaged, good water solubility, high photostability, and there is apparent application value；
3, target product B1 of the invention single-minded can develop to mitochondria, and its extremely low cytotoxicity and
High photostability is applicable to track form and viscosity change of the mitochondria in living cells for a long time.
4, target product B1 of the invention is a kind of novel mitochondrial dye.
5, the raw material of target product B1 of the invention be easy to get, synthetic route it is brief, synthesis condition is mild.
Detailed description of the invention
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 structure.
Fig. 2 is the water-soluble test of target product B1 of the present invention, illustrates that B1 has excellent water solubility.
Fig. 3 be target product B1 of the present invention to the real-time monitoring of the cell proliferation activity influence of HepG-2 and 3T3 as a result, table
Bright B1 has good biocompatibility to two kinds of cytotoxics.
Fig. 4 is the development of single, double photon and the 3D image of target product B1 of the present invention, (a) single photon (b) two-photon (c)
Overlay chart (d) three-dimensional imaging shows that B1 is able to enter intracellular and has the function of single, double photon development.
Fig. 5 is the development figure of target product B1 of the present invention Yu commercial dyes Mitotracker Far Red common location,
Pearson ' s Rr=0.8921 illustrates that B1 has being overlapped 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 Mitochondria
Microviscosity gradient distribution image, show B1 have the function of respond mitochondria viscosity (viscosity) variation.
Fig. 7 is microviscosity gradient distribution image of the target product B1 of the present invention to the imaging region of variety classes cell, is said
Bright B1 can be used as mitochondria two-photon fluorescence viscosity probe, with a wide range of applications.
Fig. 8 is the development that target product B1 of the present invention detects cell in 0-72h, illustrates that the chemical combination object light is steady
Qualitative height can be used for for a long time being tracked the mitochondria of living cells.
Specific embodiment
The preparation of the present embodiment Mitochondria two-photon fluorescence viscosity probe and biological developing method are as follows:
1, the synthesis of intermediate 1
Iodomethane (14.40g, 100mmol) is added into 50mL round-bottomed flask, is slowly dropped under stirring and is dissolved in 4mL ethyl alcohol
4-methyl pyridine (6.20g, 65mmol), be heated to 78 DEG C of back flow reaction 20min, a large amount of white crystals be precipitated, filter, ethyl alcohol
Intermediate 1,14.60g, yield 96% are obtained after washing and drying.
2, the synthesis of intermediate 2
DMSO (200mL), dimethyl hydroxyethyl amine (165g, 2200mmol), Carbon Dioxide are added into 500mL round-bottomed flask
Potassium (166g, 1200mmol) and 3 drop Aliquat-336, are warming up to 95 DEG C of reaction 10min, add 4-Fluorobenzaldehyde
(124g, 1000mmol), the reaction was continued three days at 95 DEG C；It is cooled to room temperature after reaction, reaction solution is poured into ice water, use
Salt acid for adjusting pH value collects water layer after being vigorously stirred, adjusts pH value to 11 with NaOH solution, collected organic layer operates repeatedly to 2
3 time, organic phase is collected with DCM extraction, anhydrous magnesium sulfate drying is added, obtains intermediate 2 after removing solvent, is faint yellow solid,
142g, yield 79%.
3, the synthesis of target product
Intermediate 2 (1.80g, 10mmol), intermediate 1 (2.40g, 20mmol), 30mL are added into 100mL round-bottomed flask
Dehydrated alcohol and 3 drop piperidines, are heated to 60 DEG C and are stirred to react for 24 hours, obtain dark red solution；It is added dropwise and contains into the dark red solution
There is AgNO3The 30mL ethanol solution of (1.70g, 10mmol), back flow reaction 2h are cooled down after reaction, and filtering, ethyl alcohol is washed
It washs and dries, then recrystallized with DCM, there is red crystals precipitation, 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+]
4, 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 co-cultivation in 10 minutes, PBS buffer solution is cleaned 2-3 times, then cultivates 10 with the Mitotracker Far Red of 500nM
Minute.By two-photon laser confocal microscopy, target molecule and mitochondria commercial dyes Mitotracker are found
Far Red is overlapped well, and has the function of responding mitochondria viscosity (viscosity) variation.
Claims (2)
1. a kind of mitochondria two-photon fluorescence viscosity probe, it is characterised in that its structural formula are as follows:
2. a kind of preparation method of mitochondria two-photon fluorescence viscosity probe described in claim 1, it is characterised in that including such as
Lower step:
(1) synthesis of intermediate 1
Iodomethane 100mmol is added into 50mL round-bottomed flask, the 65mmol for being dissolved in 4mL ethyl alcohol is slowly added dropwise under stirring to methyl
Pyridine is heated to back flow reaction 20min, and a large amount of white crystals are precipitated, filtering, ethanol washing and after drying intermediate 1；
(2) synthesis of intermediate 2
Into 500mL round-bottomed flask be added DMSO 200mL, dimethyl hydroxyethyl amine 2200mmol, Anhydrous potassium carbonate 1200mmol with
And 3 drop Aliquat-336,95 DEG C of reaction 10min are warming up to, add 4-Fluorobenzaldehyde 1000mmol, the reaction was continued at 95 DEG C
Three days；It is cooled to room temperature after reaction, reaction solution is poured into ice water, with salt acid for adjusting pH value to 2, collect water after stirring
Layer, with NaOH solution adjusting pH value to 11, collected organic layer is extracted with DCM and collects organic phase, and addition anhydrous magnesium sulfate is 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 into 100mL round-bottomed flask,
It is stirred to react at 60 DEG C for 24 hours, obtains dark red solution；It is added dropwise into the dark red solution and contains 10mmol AgNO330mL without
Hydrous ethanol solution, back flow reaction 2h, cools down after reaction, filtering, ethanol washing and drying, then is recrystallized with DCM, there is red
Crystal is precipitated, and obtains target product.
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| CN107382991B (en) * | 2017-08-08 | 2020-11-06 | 安徽大学 | Two-photon fluorescent material benzoxazolyl pyridine salt and preparation method and application thereof |
| CN107987014B (en) * | 2017-12-13 | 2021-02-09 | 安徽大学 | Pyridine sulfonic acid inner salt compound and preparation method and application thereof |
| US11506605B2 (en) * | 2019-05-14 | 2022-11-22 | Hach Company | System for measuring monochloramine with a thiocarbamate indicator and iodide |
| 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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