CN107325814A - A kind of fluorescence silicon nano dots and preparation method and application - Google Patents
A kind of fluorescence silicon nano dots and preparation method and application Download PDFInfo
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Abstract
The invention discloses a kind of fluorescence silicon nano dots (SiNDs), it is prepared by silane and Bengal rose red with the step of hydro-thermal method one.Compared with prior art, the SiNDs prepared by the present invention has the fluorescence quantum yield (100%) of superelevation, and can realize the long-time specific imaging to mammalian cell lysosome.In addition, the lysosome imaging effect of the SiNDs is not cleaned by cell, fixed and permeabilization etc. influences, there is resistance to cleaning, resistance to fixation and resistance to permeabilization.Meanwhile, cost is low, synthetic method is simple, water dispersible good, fluorescence emission peak width, good light stability, cell compatibility are good, the low advantage of cell phototoxicity also with preparing by the SiNDs, is expected to turn into new lysosome fluorescence probe.
Description
Technical field
The invention belongs to nano material and biological technical field, and in particular to a kind of fluorescence silicon nano dots and preparation method thereof
With application.
Background technology
Fluorescent material is widely used in biomedicine.With traditional organic fluorescence small molecular phase ratio, fluorescence nano
Material was received significant attention in recent years because it has the advantages that preferable light stabilization, adjustable excitation-emission wavelength.At present
Some fluorescent nano material species are a lot, but they all have the shortcomings that it is certain, such as：Traditional semiconductor-quantum-point (such as selenium
Cadmium, vulcanized lead etc.) the larger heavy metal element of toxicity is typically contained, so its dosage in biomedicine is by very
Big limitation；Although noble-metal nanoclusters (such as gold nanoclusters, silver nanoclusters) and the biocompatibility of upper conversion nano particle are better than
Semiconductor-quantum-point, but its quantum yield is typically relatively low, and imaging effect is not good；The synthetic method of polymer quantum dot is more multiple
It is miscellaneous, while may have considerable influence to its photoluminescent property to polymer quantum dot surface modification；Carbon point and graphene quantum dot
Fluorescence emission peak it is wider, while also have multicolor luminous property, be unfavorable for other probes while using；Other Performances of Novel Nano-Porous
There are problems that surface is difficult modification, preparation condition if rice point (such as black phosphorus quantum dot).Therefore, exploitation excellent performance and symbol
The superbright fluorescent nano material of symphysis thing medical significance is significant.
On the other hand, lysosome is the key cells device in eukaryotic, is the coated cystic structures of monofilm, includes many
A variety of exogenous and endogenic molecule and material in kind of acid hydrolase, decomposable asymmetric choice net and vitellophag, be cell digestion in
The heart.Lysosome also Apoptosis, cell autophagy, intracellular cholesteryl balance, plasma membrane reparation, cytoskeleton and tissue reconstruction,
Played an important role in a series of physiology courses such as pathogen defence and intracellular signal transduction.Quantity therefore, to lysosome,
The observation and spike of size and pattern etc. are extremely important for the behavior and destiny for understanding cell.It is molten compared with other organelles
In acid (pH 4.5-5.0) in enzyme body, therefore realize that lysosome is imaged usually using the molecule of sour environment can be targetted.
Such as, 3- (2,4- dinitroaniline) -3 '-Amino-N-methyl di-n-propylamines (DAMP) are a kind of conventional lysosome targeted moleculars,
But because the molecule itself does not have fluorescence, it is therefore desirable to which lyase could be realized by being grafted fluorescence molecule on the primary amine group of the molecule
Body is imaged.Some fluorescence molecules (such as dimethyl diaminophenazine chloride and acridine orange) are although the imaging of lysosome can be realized, they also can simultaneously
To nucleic acid imaging acid in nucleus.The lysosome fluorescence probe of current commercialization is (such as Thermo Fisher companies
LysoTracker series dyes) there is preferable lysosome imaging effect, but its synthesis cost is higher, photostability is not good and molten
Enzyme body imaging time is short.Meanwhile, such fluorescence probe surface is without modification group, it is impossible to which it is further modified and applied.
Emerging fluorescent nano material is considered as the effective ways solved the above problems.For example, the organic fluorescence nanometer of the preparation such as Lin
Particle (PVP and BPVP) though can target cancer cell lysosome, can not realize normal cell lysosome imaging
(Org.Biomol.Chem.,2009,7,2036.).The fluorescence molecule FITC in gold nano grain surface modification such as Dekiwadia
With after the polypeptide that can target lysosome, realize the imaging (J.Pept.Sci., 2012,18,527.) to lysosome.But on
State method and all do not evaluate nano particle to the Cytolysosome imaging effect after fixation and permeabilization.In addition, seeing in real time for a long time
Physiological change important role of the lysosome behavior to research cell is surveyed, and the above method can not all realize living cells lysosome
Long-time imaging.Therefore, a kind of fluorescent nano particle of good performance of development is needed badly as long-time observes the glimmering of lysosome
Light probe, to realize the long-time imaging to living cells lysosome and be imaged to the lysosome of cell after fixation and permeabilization.
The content of the invention
The technical problem to be solved in the present invention is to provide a kind of fluorescence silicon nano dots (SiNDs), to realize ultra-long time, resistance to
Cleaning, resistance to fixation, the lysosome imaging of resistance to permeabilization, the cost for solving prior art presence are high, stability difference and imaging time
Short the problems such as.
The technical problem of the invention also to be solved is to provide the preparation method and application of the fluorescence silicon nano dots.
In order to solve the above technical problems, the technical solution adopted by the present invention is as follows：
A kind of fluorescence silicon nano dots, it includes the component of following mass fraction：
100 parts of soluble silane；
1~10 part of Bengal rose red.
Wherein, it is preferably as follows the component of mass fraction：
100 parts of soluble silane；
3 parts of Bengal rose red.
Wherein, described soluble silane is aminopropyl trimethoxysilane (APTMS), aminopropyl triethoxysilane
(APTES), 3- (2- aminoethylaminos) propyl trimethoxy silicane (DAMO), 3- [2- (2- aminoethylaminos) ethyl ammonia
Base] propyl trimethoxy silicane (AEEA) or γ-glycidyl ether oxygen propyl trimethoxy silicane (GPTMS), preferably 3- [2-
(2- aminoethylaminos) ethylamino] propyl trimethoxy silicane (AEEA).
The preparation method of above-mentioned fluorescence silicon nano dots, it comprises the following steps：
Take the Bengal rose red of formula ratio to be dissolved in ultra-pure water, reacted after the soluble silane for adding formula ratio；
After the completion of reaction, the reaction solution for being down to room temperature obtains the fluorescence silicon nano dots aqueous solution through dialysis.
Wherein,
Reaction temperature is 120~250 DEG C, preferably 160 DEG C；
Reaction time is 2~24h, preferably 3h；
Reaction unit is preferably hydrothermal reaction kettle.
Wherein, the molecular cut off of bag filter is 500-1000 used in dialysing.
Application of the above-mentioned fluorescence silicon nano dots in as lysosome fluorescence probe is also within protection scope of the present invention.
Application of the Bengal rose red in fluorescence silicon nano dots are prepared is also within protection scope of the present invention；Wherein,
The described fluorescence silicon nano dots that prepare refer to and soluble silane (preferably 3- [2- (2- aminoethylaminos) ethylamino] propyl group
Trimethoxy silane) prepared with reference to foregoing method.
In the present invention, Bengal rose red is not only to be used as coloring agent, but take part in the conjunction of fluorescence silicon point
Into its synthesis to fluorescence silicon point plays an important roll, and can not be replaced with other coloring agents.
Beneficial effect：
Compared with prior art, the present invention has following advantage：
(1) fluorescence quantum yield of superelevation：The fluorescence silicon nano dots quantum yield may be up to 100%, only 20 μ g/mL sample
Product concentration is achieved with excellent lysosome imaging effect；
(2) splendid lysosome specific target tropism：More than 98% is up to the lysosome probe common location rate of commercialization, and
Even and if the probe for a long time and cell incubation, still exist only in lysosome；
(3) the lysosome imaging of ultra-long time can be realized：The probe and cell incubation and after being washed through phosphate buffer,
Still have preferable lysosome imaging effect in 48h, and the lysosome probe of commercialization only have in 2h preferable lysosome into
As effect；
(4) there is excellent anti-light bleaching power：The silicon nano dots are difficult by photobleaching under laser irradiation, and its light is stable
Property be better than commercialization lysosome dyestuff, therefore can realize that long-time continuous imaging is observed；
(5) there is good resistance to cleaning, resistance to fixation, resistance to permeabilization ability：It is cleaned multiple times in cell, fixes, after permeabilization, the silicon
Nano dot remains to have preferable imaging effect to lysosome；
(6) there is preferable biocompatibility：Tested through Cytotoxic evaluation, the silicon nano dots are in 500 μ g/mL and following
Concentration when, the toxicity to cell is very low；And after being irradiated for a long time with laser, its cytotoxicity is still very low, it was demonstrated that the material
Material has good biocompatibility and relatively low phototoxicity；
(7) preparation method of the present invention is simple, raw material is cheap and easy to get, a large amount of prepare can be achieved.
Brief description of the drawings
Fig. 1 be embodiment 1 in superbright fluorescence silicon nano dots (SiNDs) are prepared with silane reagent AEEA and Bengal rose red
Schematic diagram；
The transmission electron microscope figure that Fig. 2 is obtained SiNDs in embodiment 1；
The particle diameter statistical results chart that Fig. 3 is obtained SiNDs in embodiment 1；
Ultraviolet-visible absorption spectra figure that Fig. 4 is obtained SiNDs in embodiment 1；
Fluorescence excitation and launching light spectrogram that Fig. 5 is obtained SiNDs in embodiment 1；
Fig. 6 is obtained dullness figures of the SiNDs in different pH environment at 650nm in embodiment 1；
Fig. 7 is incubated the lysosome imaging effect after different time for obtained SiNDs in embodiment 1 in A549 cells
Figure；
Green lysosome fluorescent dye LysoTracker Greens (LT-Green) and A549 cell of the Fig. 8 for commercialization
It is incubated the lysosome imaging effect figure after different time；
Red lysosome fluorescent dye LysoTracker Reds (LT-Red) and A549 cell incubation of the Fig. 9 for commercialization
Lysosome imaging effect figure after different time；
Figure 10 places different time sections after cleaning for obtained SiNDs and LT-Green and LT-Red in embodiment 1
Lysosome imaging effect compares figure；
The fluorescent stability that Figure 11 SiNDs and LT-Red made from embodiment 1 are irradiated after different time under laser
Compare figure；
Figure 12 is obtained SiNDs and LT-Green and LT-Red resistance to fixations and resistance in A549 cells in embodiment 1
Change effect and compare figure；
Figure 13 is obtained lysosome imaging effect figures of the SiNDs in different cell lines in embodiment 1；
Figure 14 SiNDs made from embodiment 1 are in A549 cells in the cytotoxicity figure under illumination and normal condition.
Embodiment
Embodiment 1
By taking AEEA as an example, fluorescence silicon nano dots are prepared, are comprised the following steps：
(1) weigh Bengal rose red and it is completely dissolved in ultra-pure water, add the AEEA of proper volume, make AEEA
Mass ratio with Bengal rose red is 100：3.The two is fully mixed and be transferred in hydrothermal reaction kettle；
(2) react：With 160 DEG C of reaction 3h in hydrothermal reaction kettle, silicon nano dots solution is formed；
(3) purify：Dialysis produces target superbright fluorescence silicon nano dots solution.
The schematic diagram of the reaction is shown in Fig. 1, and the SiNDs prepared transmission electron microscope result is shown in Fig. 2, its particle diameter point
Cloth statistical result is shown in Fig. 3, its ultraviolet-visible absorption spectra is shown in Fig. 4, and its fluorescence excitation-emission spectrum is shown in Fig. 5, and it is in different pH
Dullness in environment at 650nm is shown in Fig. 6.Respectively scheme more than, obtained SiNDs is in unifonn spherical, and particle diameter is substantially
2.5nm, its maximal ultraviolet absorption peak is located at 511nm and located, maximum excitation wavelength and maximum emission wavelength be respectively 511nm with
525nm.It is computed, the fluorescence quantum yield of the SiNDs may be up to 100%.Especially, as shown in Figure 6 the SiNDs in faintly acid
Easy aggregate and precipitate under environmental condition, this characteristic makes it cause particle aggregation in intracellular acidic lysosome is entered, so that real
Now prolonged lysosome imaging.
Embodiment 2
SiNDs obtained by testing example 1 is to the lysosome imaging effects of A549 cells, and method is as follows：
(1) cell culture：By A549 cells with 5 × 103The density in individual/hole will be planted in 96 orifice plates, in 37 DEG C, 5%CO2
24h is cultivated in environment；
(2) cell dyeing：Change the nutrient solution in each hole into fresh medium containing 20 g/mL SiNDs, in 37 DEG C,
5%CO2Cultivate after 2,4,18 and 24h, cleaned 2 times with phosphate buffer (PBS) respectively in environment.Then, it is red with commercialization
Color lysosome fluorescent dye (LT-Red) and nuclei dyeing color reagent (Hoechst 33342) are dyed 30 and 10 minutes respectively.Most
Afterwards, with PBS cell 2 times；
(3) confocal fluorescent microscope imaging is observed：With wavelength be 405,488 and 552nm laser is as exciting light,
The dyestuffs of Hoechst 33342 launch blue-fluorescence under 405nm excitations, and SiNDs is issued in 488nm excitations
Go out green fluorescence, LT-Red dyestuffs then take on a red color fluorescence under 552nm laser.
Lysosome is imaged and common location result is shown in Fig. 7.As seen from the figure, the SiNDs is distributed mainly on after entering cell
Point-like position, after being analyzed with red commercialization lysosome fluorescent dye (LT-Red) common location, it was demonstrated that the SiNDs is lighted
Region be lysosome, and up to 98% after being computed with lysosome dyestuff common location rate.Even if in addition, administration timing of drug is extended
Still stayed in 24h, the SiNDs in lysosome.Therefore, the ability for the SiNDs targeting lysosomes that the present invention is synthesized will not be with adding
The change of medicine time and it is different, embody its lysosome imaging stability.
Embodiment 3 and 4
The lysosome Green fluorescent dye (LT-Green) and red fluorescence dyestuff (LT-Red) of commercialization are tested to A549
The lysosome imaging effect of cell.
The operating process of embodiment 3 and 4 is substantially the same manner as Example 1, need to only change SiNDs in step (2) into 1LT-
Green and LT-Red cultivate 30min, 4h and 8h respectively.
Lysosome imaging effect is shown in Fig. 8 and 9.Observe Fig. 8 and Fig. 9 to understand, the change of administration timing of drug is to green lysosome
Fluorescent dye LT-Green influence is little, but the staining foci for changing LT-Red of high degree.Prolong with administration timing of drug
It is long that to 4h, LT-Red is transferred to the regions such as the cytoplasm and nuclear membrane in addition to lysosome, or even when 8h, some dyes
Material has been enter into nucleus.As can be seen here, for compared with LT-Red, the SiNDs that the present invention is synthesized is more suitable for tracking lyase for a long time
Body is imaged.
Embodiment 5
The lysosome imaging of SiNDs made from testing example 1 and the LT-Green and LT-Red of commercialization after cleaning
Stability, method is as follows：
(1) cell culture：Step (1) in the process and embodiment 2 is consistent；
(2) cell dyeing and cleaning：Nutrient solution in cell culture well is changed into containing SiNDs (20 μ g/mL), LT- respectively
Green (1 μM) and LT-Red (1 μM) fresh medium, corresponding aperture dyeing 2h, 30min and 30min.Through twice of PBS
Afterwards, in 37 DEG C, 5%CO2Dark surrounds in cultivate respectively after 0,1,2,4,12,24,36 and 48h, be placed in confocal fluorescent show
Micro- Microscopic observation；
(3) lysosome imaging effect is observed：Exciting light is used as with 488nm and 552nm laser.Wherein, SiNDs and LT-
Green sends green fluorescence under 488nm laser, and LT-Red launches red fluorescence under 552nm laser.
Fluorescence imaging result is shown in Figure 10.Knowable to the imaging results for contrasting three kinds of dyestuffs, the lysosome dyestuff LT- of commercialization
Green and LT-Red is in the once purged 2h of cell, and the fluorescence of the two is obviously reduced.It is visibly different to be, present invention system
Standby SiNDs still has very strong fluorescence in the once purged 48h of cell, thus can realize ultra-long time lysosome it is clear into
Picture.
Embodiment 6
The lysosome that SiNDs made from testing example 1 and the LT-Red of commercialization are irradiated after different time under laser
Fluorescence imaging stability.Method is as follows：
(1) cell culture：Step (1) in the process and embodiment 2 is consistent；
(2) cell dyeing：Nutrient solution in cell culture well is changed into containing SiNDs (20 μ g/mL) and LT-Red (1 μ respectively
M fresh medium), is dyed after 2h and 30min respectively, with twice of PBS cell；
(3) laser irradiates：Cell after dyeing is placed under 488nm laser and irradiates 0,0.5,1,3,5,10,15,20 respectively
After 30min, with the micro- sem observation of confocal fluorescent；
(4) fluorescent stability is observed：Exciting light is used as with 488nm and 552nm laser.Wherein, SiNDs is in 488nm laser
Under send green fluorescence, LT-Red launches red fluorescence under 552nm laser.
As seen from Figure 11, the fluorescence for irradiating LT-Red within 3min in laser substantially weakens, and SiNDs produced by the present invention
Then clearly lysosome imaging effect is still kept after irradiation 20min.The experiment confirms that SiNDs is imaged in anti-light bleach stable
The significant advantage of aspect.
Embodiment 7
The resistance to fixation of SiNDs and commercialization LT-Green and LT-Red made from testing example 1 and the ability of resistance to permeabilization.
Step is as follows：
(1) cell culture：Step (1) in the process and embodiment 2 is consistent；
(2) cell dyeing：Step (2) in the process and embodiment 5 unanimously, with containing SiNDs (20 μ g/mL), LT-
Green (1 μM) and LT-Red (1 μM) fresh medium dye 2h, 30min and 30min respectively.Cell after dyeing is placed in
The micro- Microscopic observation of confocal fluorescent；
(3) cell is fixed：Cell after dyeing was placed in the phosphate buffer containing 4% glutaraldehyde after 30 minutes, PBS is used
Cleaning 2 times, in the micro- Microscopic observation lysosome imaging results of confocal fluorescent；
(4) cell permeabilization：Cell is handled after fixing step, then with the phosphate buffer of the X-100 containing 0.1%Triton
10 minutes, finally with PBS cell 2 times, it is placed in the micro- Microscopic observation of confocal fluorescent.Confocal fluorescent is microscopical to be set
Step (3) in condition and embodiment 5 is consistent.
As shown in Figure 12, LT-Green and LT-Red be not suitable for through the fixed lysosome with the cell after permeabilization into
Picture, and lysosome image probe produced by the present invention has resistance to fixation and anti-permeabilization ability.
Embodiment 8
Lysosome imaging effects of the SiNDs made from testing example 1 in different cell lines, its operating procedure is with implementing
Example 2 is roughly the same, only into the A549 cells in embodiment 2 need to be changed to normal pneumonocyte AT II, breast cancer cell MCF-7 respectively
With macrophage Raw 264.7, dyeing time is changed to 2h.
Figure 13 shows that the SiNDs that the present invention is synthesized is respectively provided with excellent lysosome imaging capability in different cell lines.
Embodiment 9
Cytotoxicities of the SiNDs to A549 cells under dark condition and illumination condition made from testing example 1, it is grasped
Make step as follows：
(1) cell culture：Step (1) in the process and embodiment 2 is consistent；
(2) SiNDs processing：Nutrient solution in cell culture well is changed into the fresh cultured of the SiNDs containing various concentrations respectively
Liquid, SiNDs concentration gradient is：0,50,100,200,500 and 1000 μ g/mL, in 37 DEG C, 5%CO2In environment cultivate 24h it
Afterwards.Cell is divided into two groups, one group is placed under white light and irradiates 30min, and another group is then placed under dark surrounds.Then, by two groups
Cell is put in 37 DEG C, 5%CO24h is cultivated in environment；
(3) cytoactive detection：Cytotoxicity is detected by mtt assay.
Cell survival rate result such as Figure 14.As seen from the figure, though SiNDs at concentrations up to 200 μ g/mL, illumination and not only
More than 90% activity is kept according to the cell of group, the hypotoxicity for the SiNDs that the present invention is synthesized is embodied, becomes a kind of peace
Full lysosome imaging fluorescence probe.
Claims (7)
1. a kind of fluorescence silicon nano dots, it is characterised in that it includes the component of following mass fraction：
100 parts of soluble silane；
1~10 part of Bengal rose red.
2. fluorescence silicon nano dots according to claim 1, it is characterised in that described soluble silane is aminopropyl front three
TMOS, aminopropyl triethoxysilane, 3- (2- aminoethylaminos) propyl trimethoxy silicane, 3- [2- (2- amino second
Base amino) ethylamino] propyl trimethoxy silicane or γ-glycidyl ether oxygen propyl trimethoxy silicane.
3. the preparation method of the fluorescence silicon nano dots described in claim 1, it is characterised in that it comprises the following steps：
Take the Bengal rose red of formula ratio soluble in water, reacted after the soluble silane for adding formula ratio；Reaction is completed
Afterwards, the reaction solution for being down to room temperature obtains the fluorescence silicon nano dots aqueous solution through dialysis.
4. preparation method according to claim 3, it is characterised in that reaction temperature is 120~250 DEG C, and the reaction time is 2
~24h.
5. preparation method according to claim 3, it is characterised in that the molecular cut off of dialysis bag filter used is 500
~1000.
6. application of the fluorescence silicon nano dots in as lysosome fluorescence probe described in claim 1.
7. application of the Bengal rose red in fluorescence silicon nano dots are prepared.
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| CN111647400A (en) * | 2020-06-11 | 2020-09-11 | 吉林大学第一医院 | Preparation method of fluorescent organic silicon nano particles |
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| CN108844937B (en) * | 2018-08-07 | 2020-09-08 | 福建中医药大学 | Water-soluble fluorescent silicon dot and preparation method and application thereof |
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| CN111647400A (en) * | 2020-06-11 | 2020-09-11 | 吉林大学第一医院 | Preparation method of fluorescent organic silicon nano particles |
| CN113174255A (en) * | 2021-04-08 | 2021-07-27 | 华南农业大学 | Preparation method and application of water-soluble green fluorescent silanized carbon dots |
| CN114702954A (en) * | 2021-12-23 | 2022-07-05 | 郑州中科生物医学工程技术研究院 | Preparation method of fluorine-doped silicon quantum dots and application of fluorine-doped silicon quantum dots in detection of neo-carmine |
| CN114702954B (en) * | 2021-12-23 | 2023-09-05 | 郑州中科生物医学工程技术研究院 | Preparation method of fluorine-doped silicon quantum dot and application of fluorine-doped silicon quantum dot in detection of new carmine |
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