CN105315988A - Fluorochrome for cytolysosome positioning and preparation method and application thereof - Google Patents

Fluorochrome for cytolysosome positioning and preparation method and application thereof Download PDF

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CN105315988A
CN105315988A CN201510013216.6A CN201510013216A CN105315988A CN 105315988 A CN105315988 A CN 105315988A CN 201510013216 A CN201510013216 A CN 201510013216A CN 105315988 A CN105315988 A CN 105315988A
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formula
cell
preparation
tetraphenyl ethylene
fluorochrome
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刘又年
臧启光
王立强
邓留
李娟�
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Central South University
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Central South University
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Abstract

The invention discloses fluorochrome for cytolysosome positioning and a preparation method and application thereof. The preparation method of the fluorochrome compound includes the steps that a benzophenone derivative containing methyl substituents is reacted under the catalysis of Zn/TiC14, an obtained product and N-bromosuccinimide are subjected to a bromination reaction, then a product is reacted with morpholine, and the tetraphenyl ethylene derivative stain containing morpholine groups is obtained. The preparation method is easy to implement, raw materials are easy to get, and reaction conditions are mild. The obtained fluorochrome contains tetraphenyl ethylene fluorescence groups capable of gathering the activity of inducing fluorescence emission and can be used for performing specific staining on all kinds of cytolysosome. The fluorochrome has the advantages of being small in cytotoxicity, stable in cell metabolism resistance, good in photobleaching resisting effect and the like and hardly affects normal physiological activities of cells, and a new method is provided for observing the morphologic changes of cytolysosome for a long time. The fluorochrome can be widely applied to monitoring the morphology of cytolysosome, observing the apoptosis process and the like.

Description

A kind of Cytolysosome location fluorescence dye and its preparation method and application
Technical field
The present invention relates to a kind of Cytolysosome location fluorescence dye and its preparation method and application, belong to bioanalysis detection technique field.
Background technology
Lysosome is organoid important in cell, and play the critical functions such as intracellular organic matter katabolism, Immune discrimination, immune defense, meanwhile, lysosome also plays key player in apoptosis process.Therefore, location lysosomal in cell, tracking and morphologic observation are had great importance to the vital process understanding whole cell.
Lysosomal imaging is adopted usually to the method [HZhu, JFan, etal.Chem.Commun.2012,48,11766] of fluorescence targeted imaging.Business-like lysosome target fluorescence dye comprises at present redDND, LysoTrackerGreenDND-26, Lyso-TrackerBlue etc.These fluorescence dyes have targeting to lysosome, can be positioned the lysosome in cell.But this fluorochrome is owing to being in solution state, is usually faced with and is easy to the problems such as photobleaching, bio-toxicity is large, antibiont metabolic capacity is low occur.The particularly inner complex environment of lysosome, as caused the destruction of dye structure containing a large amount of high active enzyme and lower pH environment etc.Another kind of lysosome dyeing process adopts quantum dot fluorescence imaging [LCao, XWang, etal.J.Am.Chem.Soc.2007,129,11318], but due to current most of quantum dot, as CdS contains heavy metal, there is bio-toxicity, and the surface properties of quantum dot changes and may cause fluorescent quenching, also limits the application of quantum dot in fluorescence imaging.Therefore, urgently exploitation has good biocompatibility, high light stability and resistance to enzymolysis metabolism and long-time stable can be positioned lysosomal fluorescence dye.
Carry out under the lysosome target fluorescence dye reported at present is solution state cell dyeing [Zhou Xiang, Wu Zhiguo, field TOOLING, Weng little Cheng. China, CN10962536B, 2010-10-13; Fan Jiangli, Zhu Hao, Peng Xiaojun, Xu Qunli. China, CN102796395B, 2012-08-17; Fan Jiangli, Dong Huijuan, Peng Xiaojun, Hu Mingming. China, CN103044947B, 2013-01-09; Shen Zhen, Liu Hanzhuan, Guo Qiuli. China, CN103242355A, 2013-05-10].After organic molecule self-assembly in aqueous phase is colloidal particle, effectively can improve dye molecule to the tolerance of enzymolysis metabolism and light stability.Tetraphenyl ethylene group has aggregation inducing fluorescent emission (AIE) active [XDuan, JZeng, etal.J.Org.Comm.2006,71,98737], makes its assembling colloidal particle have stronger fluorescent emission performance.
Summary of the invention
An object of the present invention is to provide a kind of anti-light bleaching and good biocompatibility, and have the lysosome target fluorescent dye compound of the active tetraphenyl ethylene fluorophor of aggregation inducing fluorescent emission (AIE).
Two of object of the present invention is to provide the method that reaction conditions is gentle, simple to operate, low cost prepares described fluorescent dye compound.
Three of object of the present invention is to provide described luminescent dye molecule to be applied to lysosomal specific stain in active somatic cell.This luminescent dye molecule has that anti-light bleaching effect is good, biocompatibility is high, strong, the lysosome-targeting height of resistance to enzymolysis ability, can monitor the advantage such as lysosome metamorphosis in active somatic cell for a long time.
The invention provides a kind of fluorescent dye compound, this fluorescent dye compound has structure shown in formula 1:
Wherein, R 1, R 2, R 3and R 4be selected from the one in group, H atom, methyl, F atom or the methoxyl group with formula 2 structure independently of one another, and R 1, R 2, R 3and R 4in have at least one to be selected from the group with formula 2 structure.
Preferred luminescent dye molecule has structure shown in formula 3:
The invention provides the preparation method of luminescent dye molecule, will there is the benzophenone derivative of formula 4 structure and formula 5 structure at Zn/TiCl 4react under catalysis, obtain 1,1,2, the 2-tetraphenyl ethylene derivative with formula 6 structure; There is bromination reaction in gained 1,1,2,2-tetraphenyl ethylene derivative and N-bromosuccinimide (NBS), reaction product is reacted with morpholine again, obtains the tetraphenyl ethylene derivative containing morpholine group with formula 1 structure.
Wherein, R 5, R 6, R 7and R 8be selected from the one in H atom, methyl, F atom or methoxyl group independently of one another, R 5, R 6, R 7and R 8in have at least one to be selected from methyl.
The preparation method of fluorescent probe molecule of the present invention also comprises following preferred version:
Preferred R 5, R 6, R 7and R 8group is methyl or H atom and at least comprises a methyl; Most preferably be containing two methyl.
The benzophenone derivative in preferred preparation method with formula 4 structure and formula 5 structure refluxes 6 ~ 10h in tetrahydrofuran (THF).
1,1,2,2-tetraphenyl ethylene derivative described in preferred preparation method and N-bromosuccinimide back flow reaction 6 ~ 8h in tetracol phenixin.
1,1,2,2-tetraphenyl ethylene benzyl br-derivatives described in preferred preparation method and morpholine reflux 1-3h in Isosorbide-5-Nitrae-dioxane.
Present invention also offers the application of fluorescence dye, this application is lysosome target fluorescence imaging fluorescence dye being applied to viable cell.
Preferred application method, after being dissolved by fluorescence dye, then joins in cell culture fluid the staining fluid obtained containing fluorescence dye, moves in adherent viable cell culture system and dye with a small amount of water-miscible organic solvent.
Water-miscible organic solvent described in preferred application method comprises acetone, tetrahydrofuran (THF), dimethyl sulfoxide (DMSO), acetonitrile, acetone etc., and most preferred solvent is dimethyl sulfoxide (DMSO).
Viable cell described in preferred application method is all kinds of attached tumor cell lines and normal cell system.
Described dyeing time can between 0.5 ~ 24h.
Fluorescent dye compound synthetic route of the present invention following (synthesizing example with what there is the fluorescent probe molecule of formula 3 structure):
Fluorescent dye compound of the present invention builds tetraphenyl ethylene fluorescence skeleton by 4,4 '-disubstituted benzophenone derivates, and introduces morpholine structural unit as lysosome target group.The lysosomal mechanism of fluorescent dye compound target of the present invention is: the morpholine structural unit in such luminescent dye molecule has weakly alkaline (see Fig. 1), in cell, lysosomal pH is generally lower than 6.0, therefore under the promotion of pH gradient, dye molecule can a large amount of enrichment in lysosome, thus reaches targeted imaging effect.
Beneficial effect of the present invention:
The preparation method of fluorescent dye compound of the present invention is simple to operate, and raw material is easy to get, and reaction conditions is gentle.
Fluorescent dye compound stable chemical nature of the present invention, cytotoxicity is low, and anti-light bleaching effect is good, strong to lysosome station-keeping ability.
Luminescent dye molecule of the present invention can be assembled into colloidal particle in cell culture medium, effectively can improve the tolerance of dyestuff to enzyme classes in cell, make the dye molecule of this state of aggregation to be present in the long period in cell, therefore can realize the day-night observation to viable cell lysosome metamorphosis in 0.5 ~ 24h ultra-long time.
Luminescent dye molecule of the present invention is assembled into colloidal state in aqueous, produces hyperfluorescenceZeng Yongminggaoyingguang simultaneously transmit in 400 ~ 600nm wave band.In the substratum containing such dyestuff after culturing cell 0.5 ~ 24h, obvious intracellular Fluorescence can be observed under fluorescent microscope.Fluorescent dye compound elementary cell toxicity of the present invention is very little, and under normal dyeing concentration, process cell 1 ~ 48h, cell survival rate is higher than 80%.When being applied to cell imaging, its anti-light bleaching effect is better than commercial lysosome target dyestuff at present, and after the scanning of certain hour exciting light, the loss of signal is less than 25%, and commercialization dyestuff as a comparison redDND, its loss of signal is more than 70%.Such fluorescent dye compound is monitored for a long time at cytase volume morphing, the field such as observation of lysosome metamorphosis is with a wide range of applications in cellular physiological processes.
Accompanying drawing explanation
[Fig. 1] obtains the pH-fluorescence intensity graph of a relation of fluorescence dye for embodiment 1.Detection system is citrate-phosphate disodium hydrogen damping fluid (100mmol/L).
[Fig. 2] is for the obtained fluorescence dye of embodiment 1 is to the toxotest of L929 cell: adopt MTT method to calculate the cell survival rate after containing the culture medium culturing different time of different concns dyestuff.X-coordinate is the concentration (μm ol/L) of dyestuff.
[Fig. 3] is for the obtained fluorescence dye of embodiment 1 is to the toxotest of MCF-7 cell: adopt MTT method to calculate the cell survival rate after containing the culture medium culturing different time of different concns dyestuff.X-coordinate is the concentration (μm ol/L) of dyestuff
[Fig. 4] is the obtained fluorescence dye of embodiment 1 and commercialization lysosome target dyestuff redDND is to L929 cell Coloration experiment altogether.Blue channel Ch1 is the fluorescent signal of embodiment 1 gained dyestuff, and red channel Ch2 is redDND fluorescent signal.Image to right is Ch1 and the Ch2 channel fluorescence intensity-location diagram of dashed part in cell imaging figure.
[Fig. 5] is embodiment 1 gained fluorescence dye and commercialization lysosome target dyestuff light stability test after RedDND dyes altogether to L929 cell.Left side four pictures are fluorescence intensity under original state and stacking diagram, four, right side for after scanning 6.5min, the fluorescence intensity of each passage and stacking diagram.
[Fig. 6] is the obtained fluorescence dye of embodiment 1 and commercialization lysosome target dyestuff redDND strength of signal-sweep time graph of a relation.In figure, signal original state intensity is normalized.
[Fig. 7] is for the obtained fluorescence dye of embodiment 1 is to the observation figure of lysosome metamorphosis in L929 apoptosis process.Containing in the substratum of 10 μm of ol/L dye molecules, add 5 FU 5 fluorouracil, H respectively 2o 2, cis-DDP, carry out cell death inducing.Observe respectively at when 3h, 12h, 24h.
The proton nmr spectra of 1,2-bis-(4-brooethyl-phenyl)-1,2-diphenylethlene that [Fig. 8] obtains for embodiment 1.
The proton nmr spectra of the target compound that [Fig. 9] obtains for embodiment 1.
The high resolution mass spectrum of the target compound that [Figure 10] obtains for embodiment 1.
Embodiment
Following examples are intended to further illustrate content of the present invention, instead of limit the scope of the invention.
Embodiment 1:
The preparation of 1,2-bis-(4-methylphenyl)-1,2-diphenylethlene
4-methyl benzophenone (10.80g, 30mmol), Zn powder (9.75g, 150mmol) are added in 650mL anhydrous tetrahydro furan, titanium tetrachloride (8.3mL is dripped under ice bath, 75mmol), 1.6mL pyridine is added, then reflux.Monitor reaction process with thin-layer chromatography, treat raw material reaction complete (about needing 8h), cool to room temperature, distillation is except desolventizing.Use dichloromethane extraction again, organic phase uses saturated aqueous common salt and water washing respectively.Be separated organic phase, add anhydrous sodium sulfate drying, distillation is except desolventizing, and (developping agent is sherwood oil to column chromatographic isolation and purification: methylene dichloride=5: 1, R f=0.8) light yellow solid 1,2-bis-(4-methylphenyl)-1,2-diphenylethlene is obtained, output 9.80g, productive rate 90.6%.
The preparation of 1,2-bis-(4-brooethyl-phenyl)-1,2-diphenylethlene
By upper step obtained 1,2-bis-(4-methylphenyl)-1,2-diphenylethlene (9.80g, 27.18mmol), NBS (9.70g, 54.40mmol), benzoyl peroxide (BPO) (0.10g, 0.5mmol) add in 250mL tetracol phenixin, reflux.Monitor reaction process with thin-layer chromatography, treat raw material reaction complete (~ 10h), cool to room temperature, successively with saturated sodium sulfite solution and deionized water wash.Separated and collected organic phase, adds anhydrous sodium sulfate drying, and distillation is except desolventizing.After dissolving with a small amount of methylene dichloride, add sherwood oil, place in air, after methylene dichloride volatilization, separate out white crystals.After collecting crude product crystal, with dichloromethane-petroleum ether system recrystallization.Obtain White crystalline product 1,2-bis-(4-brooethyl-phenyl)-1,2-diphenylethlene, output 5.93g, productive rate 41.1%.
H 1nMR (400MHz, CDCl 3): δ ppm=7.192-7.092 (10H, m), 7.072-6.964 (8H, m), 4.44 (4H, d, J=6.4Hz). (nuclear-magnetism figure is shown in Fig. 8)
The preparation of target compound
Take step obtained 1, 2-bis-(4-brooethyl-phenyl)-1, 2-diphenylethlene (0.20g, 0.386mmol), be dissolved in 6mL1, in 4-dioxane, add 1mL morpholine (greatly excessive), reflux 30min, after being cooled to room temperature, add 10mL methylene dichloride, subsequently with deionized water extraction removing dioxane solvent and excessive morpholine, after organic phase is revolved and is steamed removing methylene dichloride, crude product is crossed silica gel chromatographic column (ethyl acetate is as developping agent, respectively there is a blue-green fluorescent point having AIE character at Rf=0.6 and 0.3 place), collect to obtain target compound (white powdery solids, output 0.073g, productive rate 36%) and cis-isomeride (white powdery solids, output 0.055g, productive rate 27%), this target compound structure is shown in Figure of description 9.
H 1nMR (500MHz, CDCl 3): δ ppm=7.119-7.079 (6H, m), 7.078-7.014 (8H, m), 6.987 (4H, d, J=8.0Hz), 3.719 (8H, t, J=4.0Hz), (3.433 4H, s), 2.412 (8H, s). (nuclear-magnetism figure is shown in Fig. 9)
MS:m/zcalcdforC 36h 39n 2o 2 +[M-H +]: 531.30, found531.30066. (mass spectrum is shown in Figure 10)
Embodiment 2
The actual Color of viable cell of lysosome target fluorescence dye
This fluorescence dye is dissolved in DMSO, obtains probe solution (0.001mol/L), after degerming with 0.22 μm of membrane filtration, join containing in 15%FBS and 1% dual anti-high glycoform DMEM/F12 substratum, shake up, obtain cell dyeing working fluid.After this working fluid and attached cell Dual culture certain hour, under laser confocal microscope, observe staining conditions.Fig. 2 and Fig. 3 shows, the cytotoxicity of this dyestuff is very little, and within 10 μm of ol/L concentration, after cultivating 48h, the survival rate of L929 cell and MCF-7 cell is all more than 90%.Proved (experimental result is shown in Fig. 4) by common Coloration experiment, this dyestuff has highly lysosome-targeting matter, can carry out lysosome vital staining rapidly and accurately.Fig. 5 and Fig. 6 shows, this dyestuff has excellent anti-light bleaching characteristic.With commercialization dyestuff redDND compares, and this dyestuff is after the excitation light irradiation of 6.5min, and its signal attenuation is less than 25%, and the decay of RedDND dye signal reaches 70%.
Embodiment 3
The tracking observation of lysosome target fluorescence dye lysosome form in apoptosis process
Get the adherent L929 cell being in logarithmic phase, the substratum added containing 10 μm of ol/L dyestuffs is cultivated.Add 5 FU 5 fluorouracil in the substratum of part cell, make 5 FU 5 fluorouracil concentration in cell culture system be 300 μ g/mL; H is added in the substratum of part cell 2o 2, make H in cell culture system 2o 2concentration is 100 μ g/mL; Add cis-DDP in the substratum of part cell, make concentration in cell culture system be 100 μ g/mL; Utilize the effect induction L929 cell undergoes apoptosis of three kinds of medicines.The observation of Cytolysosome form is carried out respectively at drug effect 3h, 12h, 24h time point.Result shows, and when L929 apoptosis, in cell, lysosome volume becomes large, and lysosome proportion in tenuigenin increases simultaneously.By the observation to lysosome metamorphosis in apoptosis process, also show the advantage that this dye molecule is observed active somatic cell lysosome long-time continuous.(accompanying drawing 7 is shown in by lysosome metamorphosis).

Claims (8)

1. a lysosome location fluorescence dye, is characterized in that, has structure shown in formula 1:
Wherein, R 1, R 2, R 3and R 4be selected from the one in group, H atom, methyl, F atom or the methoxyl group with formula 2 structure independently of one another, and R 1, R 2, R 3and R 4in have at least one to be selected from the group with formula 2 structure.
2. the preparation method of the fluorescent molecular probe compound shown in claim 1, is characterized by:
There is the benzophenone derivative of formula 3 structure and formula 4 structure at Zn/TiCl 4react under catalysis, obtain 1,1,2, the 2-tetraphenyl ethylene methyl-derivatives with formula 5 structure; There is bromination reaction in gained 1,1,2,2-tetraphenyl ethylene methyl-derivatives and N-bromosuccinimide (NBS), obtains 1,1,2,2-tetraphenyl ethylene benzyl br-derivatives; Gained 1,1,2,2-tetraphenyl ethylene benzyl br-derivatives reacts with morpholine again, obtains the tetraphenyl ethylene derivative containing morpholine group with formula 1 structure, i.e. lysosome location fluorescence dye involved by this patent;
Wherein, R 5, R 6, R 7and R 8be selected from the one in H atom, methyl, F atom or methoxyl group independently of one another, R 5, R 6, R 7and R 8in have at least one to be selected from methyl.
3. preparation method as claimed in claim 2, is characterized in that having benzophenone derivative heating reflux reaction 6 ~ 10h in tetrahydrofuran (THF) of formula 3 structure and formula 5 structure.
4. preparation method as claimed in claim 2, is characterized by:
1,1,2,2-described tetraphenyl ethylene methyl-derivatives and N-bromosuccinimide heating reflux reaction 6 ~ 8h in tetracol phenixin.
5. preparation method as claimed in claim 2, is characterized by:
1,1,2,2-described tetraphenyl ethylene benzyl br-derivatives and morpholine heating reflux reaction 1 ~ 3h in Isosorbide-5-Nitrae-dioxane.
6. the application of the dyestuff shown in claim 1, is characterized by:
Be applied to lysosomal positioning dyeing in viable cell, and, be applied to the real-time fluorescence imaging in viable cell.
7. apply as claimed in claim 6, it is characterized by:
After the dye molecule shown in claim 1 being dissolved with a small amount of water-miscible organic solvent, join in cell culture fluid, obtain the staining fluid containing dyestuff colloid, after co-culture of cells 0.5 ~ 24h to be measured, carry out fluorescence microscopy observation.
8. apply as claimed in claim 6, it is characterized by:
Described detection cell is the tumour cell, the normal cell that are in logarithmic phase, and, be in the tumour cell of apoptosis phase, normal cell.
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WO2018120970A1 (en) * 2016-12-27 2018-07-05 广东阿格蕾雅光电材料有限公司 Green light dye with aggregation-induced emission property
CN106749163A (en) * 2016-12-30 2017-05-31 南京理工大学 The self-assembled supermolecular of tetraphenyl ethylene Bis-Crown Ethers and the azole derivatives of fluorine boron two
CN107200709A (en) * 2017-05-24 2017-09-26 华南理工大学 One class has the fluorescent chemicals of aggregation-induced emission property and its application in cell fluorescence imaging field
CN107200709B (en) * 2017-05-24 2020-04-28 华南理工大学 Fluorescent compound with aggregation-induced emission property and application thereof in cell fluorescence imaging field
CN109030156A (en) * 2018-10-19 2018-12-18 武汉百合龙腾生物科技有限责任公司 A kind of flow cytometer showed dyeing liquor
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CN110174387A (en) * 2019-06-14 2019-08-27 郑州大学 A kind of application of fluorescent carbon point in naturally targeting lysosome
CN111434656A (en) * 2019-11-12 2020-07-21 陕西师范大学 Aggregation-induced photosensitive material with lysosome targeting property and preparation method and application thereof
CN111434656B (en) * 2019-11-12 2023-02-03 陕西师范大学 Aggregation-induced photosensitive material with lysosome targeting property and preparation method and application thereof
CN112028871A (en) * 2020-08-20 2020-12-04 宁波大学 Lysosome targeted photosensitizer, synthetic method and application in biological imaging
CN112028871B (en) * 2020-08-20 2021-12-28 宁波大学 Lysosome targeted photosensitizer, synthetic method and application in biological imaging
CN113899725A (en) * 2021-10-12 2022-01-07 江苏省人民医院（南京医科大学第一附属医院） Method for real-time quantitative detection of degranulation and killing capacity of NK effector cells

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