CN106833629A - A kind of Mitochondrially targeted fluorescent carbon point and its preparation method and application - Google Patents
A kind of Mitochondrially targeted fluorescent carbon point and its preparation method and application Download PDFInfo
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- CN106833629A CN106833629A CN201710006129.7A CN201710006129A CN106833629A CN 106833629 A CN106833629 A CN 106833629A CN 201710006129 A CN201710006129 A CN 201710006129A CN 106833629 A CN106833629 A CN 106833629A
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- carbon point
- fluorescent carbon
- mitochondrially targeted
- shitosan
- ethylenediamine
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 title claims abstract description 98
- 229910052799 carbon Inorganic materials 0.000 title claims abstract description 98
- 238000002360 preparation method Methods 0.000 title claims abstract description 24
- 239000003814 drug Substances 0.000 claims abstract description 25
- ACTRVOBWPAIOHC-UHFFFAOYSA-N succimer Chemical compound OC(=O)C(S)C(S)C(O)=O ACTRVOBWPAIOHC-UHFFFAOYSA-N 0.000 claims abstract description 25
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims abstract description 24
- 210000003470 mitochondria Anatomy 0.000 claims abstract description 24
- 239000002994 raw material Substances 0.000 claims abstract description 10
- 238000001027 hydrothermal synthesis Methods 0.000 claims abstract description 9
- 239000000523 sample Substances 0.000 claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 229920001661 Chitosan Polymers 0.000 claims description 5
- 239000012467 final product Substances 0.000 claims description 5
- 230000008685 targeting Effects 0.000 claims description 5
- 238000005119 centrifugation Methods 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 230000001093 anti-cancer Effects 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 238000003384 imaging method Methods 0.000 abstract description 18
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 8
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- 238000011275 oncology therapy Methods 0.000 abstract description 4
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- 238000012360 testing method Methods 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 201000011510 cancer Diseases 0.000 description 6
- 239000000463 material Substances 0.000 description 6
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- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- 206010006187 Breast cancer Diseases 0.000 description 3
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- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- 108010019160 Pancreatin Proteins 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
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- 229940055695 pancreatin Drugs 0.000 description 2
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- TUFFYSFVSYUHPA-UHFFFAOYSA-M rhodamine 123 Chemical compound [Cl-].COC(=O)C1=CC=CC=C1C1=C(C=CC(N)=C2)C2=[O+]C2=C1C=CC(N)=C2 TUFFYSFVSYUHPA-UHFFFAOYSA-M 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- AKYHKWQPZHDOBW-UHFFFAOYSA-N (5-ethenyl-1-azabicyclo[2.2.2]octan-7-yl)-(6-methoxyquinolin-4-yl)methanol Chemical compound OS(O)(=O)=O.C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 AKYHKWQPZHDOBW-UHFFFAOYSA-N 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 206010008342 Cervix carcinoma Diseases 0.000 description 1
- 239000001576 FEMA 2977 Substances 0.000 description 1
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
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- 239000006285 cell suspension Substances 0.000 description 1
- 230000019522 cellular metabolic process Effects 0.000 description 1
- 201000010881 cervical cancer Diseases 0.000 description 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
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- 238000011161 development Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
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- 238000002284 excitation--emission spectrum Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000002866 fluorescence resonance energy transfer Methods 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 239000012216 imaging agent Substances 0.000 description 1
- 201000007270 liver cancer Diseases 0.000 description 1
- 210000005229 liver cell Anatomy 0.000 description 1
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- 210000002540 macrophage Anatomy 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
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- 238000012544 monitoring process Methods 0.000 description 1
- 239000002086 nanomaterial Substances 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
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- 229910052760 oxygen Inorganic materials 0.000 description 1
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- 239000002245 particle Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 238000002428 photodynamic therapy Methods 0.000 description 1
- 238000007626 photothermal therapy Methods 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229960003110 quinine sulfate Drugs 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
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- 238000002560 therapeutic procedure Methods 0.000 description 1
- IMRYETFJNLKUHK-UHFFFAOYSA-N traseolide Chemical compound CC1=C(C(C)=O)C=C2C(C(C)C)C(C)C(C)(C)C2=C1 IMRYETFJNLKUHK-UHFFFAOYSA-N 0.000 description 1
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/08—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials
- C09K11/65—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing carbon
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/001—Preparation for luminescence or biological staining
- A61K49/0013—Luminescence
- A61K49/0017—Fluorescence in vivo
- A61K49/0019—Fluorescence in vivo characterised by the fluorescent group, e.g. oligomeric, polymeric or dendritic molecules
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- A61K49/00—Preparations for testing in vivo
- A61K49/001—Preparation for luminescence or biological staining
- A61K49/0063—Preparation for luminescence or biological staining characterised by a special physical or galenical form, e.g. emulsions, microspheres
- A61K49/0069—Preparation for luminescence or biological staining characterised by a special physical or galenical form, e.g. emulsions, microspheres the agent being in a particular physical galenical form
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Abstract
The invention discloses a kind of Mitochondrially targeted fluorescent carbon point and its preparation method and application, the fluorescent carbon point is mainly and is made up of the raw material of following weight ratio：1-20 part of shitosan, 1-10 part of ethylenediamine and with 1-10 part of dimercaptosuccinic acid.And with shitosan, ethylenediamine and dimercaptosuccinic acid as raw material, the carbon point with excellent photoluminescent property is obtained using the step of hydro-thermal method one.Relative to prior art, the carbon point is not only able to realize quick, No clean, long-time, light stabilization (bleach-resistant) imaging mitochondrial to mammalian cell, it is alternatively arranged as carrier and cancer therapy drug orientation is delivered to mitochondria, so as to realizes based on mitochondrial neoplasm targeted therapy.Additionally, the carbon point also has, and preparation cost is low, water dispersible is good, the low advantage of cytotoxicity, it is expected to replace now widely used commercialization mitochondria fluorescence probe.
Description
Technical field
The invention discloses a kind of Mitochondrially targeted fluorescent carbon point and its preparation method and application, belong to Bio-Nano-Materials
Technical field.
Background technology
Either in mammal normal cell or sick cell, mitochondria is all deep with the effect of its uniqueness
Affect the vital movement of cell, such as product of the generation of ATP and cell energy supply, the Calcium Signal of cell interior and free radical
Stable state of the raw, regulation and control of Apoptosis and maintenance cell interior environment etc..Because mitochondria has emphatically to cell metabolism
The diseases such as the meaning wanted, mitochondrial dysfunction and diabetes, tumour, Parkinson's disease and alzheimer disease are sent out
Exhibition is closely related.Therefore to the observation of mitochondrial quantity, pattern etc. and the state and vital movement for finding out cell are studied
It is most important.Further, since mitochondria to active oxygen and heat sensitiveness, mitochondria also become cancer photodynamic therapy and
The important target of photo-thermal therapy.
On the other hand, fluorescence colour is to realize the main method of mitochondria imaging, therefore develops corresponding line grain
Body fluorescence probe is current study hotspot.The mitochondria fluorescence probe of present commercialization is mainly including Rhodamine 123, with line
The green fluorescent protein (mito-GFP) and MitoTracker series dyes of grain targeting property.These dyestuffs are because its height is special
Different Mitochondrially targeted characteristic and strong fluorescence signal can be produced and favor is endured to the fullest extent, but they there is also many shortcomings such as
Synthesis is complicated, expensive, the poor and photostability of water solubility is poor etc., so as to limit their application to a certain extent.
At the same time, the new approaches that mitochondrial Targeted cancer therapy is current treating cancer are positioned at.Because pin
Mitochondrial medicine can effectively be destroyed and kill cancer so as to improve medicine for the extremely important mitochondria of cell activities
The efficiency of cell.Development mitochondria targeted drug, most common method is using Mitochondrially targeted part such as triphenylphosphine (TPP)
Covalent modification is carried out to medicine, so as to assign medicine Mitochondrially targeted ability.But, because the part toxicity is larger, and its
Itself not possessing photoluminescent property, therefore must also generally introduce other fluorescence molecules in the process modified could realize to medicine
Fluorescent tracing, but other molecules for introducing can reduce the Mitochondrially targeted property of medicine after modification.These shortcomings also become this and match somebody with somebody
Body is used to realize the Mitochondrially targeted bottleneck for transporting of medicine.It is comprehensive described, develop one kind and be provided simultaneously with fluorescence probe and medicine
The Mitochondrially targeted molecule of carrier dual-use function or the importance of nano particle are self-evident.
The content of the invention
Goal of the invention：For above-mentioned technical problem, the invention provides a kind of fluorescent carbon point, and many amido chemical combination are utilized
Thing and multi-carboxy compound, and by hydrothermal synthesis method, the method for preparing the fluorescent carbon point；And the online grain of fluorescent carbon point
Application in terms of body imaging and Mitochondrially targeted drug carrying ability.
Technical scheme：The invention provides a kind of Mitochondrially targeted fluorescent carbon point, it is mainly by following weight ratio
Raw material be made：
1-20 part of shitosan, 1-10 part of ethylenediamine and with 1-10 part of dimercaptosuccinic acid.
It is preferred that, described Mitochondrially targeted fluorescent carbon point is mainly and is made up of the raw material of following weight ratio：
1 part of shitosan, 1-10 part of ethylenediamine and with 1-10 part of dimercaptosuccinic acid.
It is preferred that, described Mitochondrially targeted fluorescent carbon point is mainly and is made up of the raw material of following weight ratio：
20 parts of shitosan, 1-10 part of ethylenediamine and with 1-10 part of dimercaptosuccinic acid.
It is preferred that, the chitosan molecule amount is in 10kDa-1000kDa.
Present invention also offers the Mitochondrially targeted fluorescent carbon point preparation method, comprise the following steps：By shitosan, second
Diamines and mixed liquor is made with dimercaptosuccinic acid, then reacts certain hour under hydrothermal condition, lowered the temperature, filtering or centrifugation obtain final product institute
State the solution of targeting fluorescent carbon point.
It is preferred that, comprise the following steps：
(1) weigh shitosan, ethylenediamine and and dimercaptosuccinic acid, wherein shitosan heating for dissolving in dilute hydrochloric acid solution,
Ethylenediamine and dimercaptosuccinic acid are then added into chitosan solution mixing, and mixed liquor is added in hydrothermal reaction kettle；
(2) with 160-200 DEG C of 12-48h of reaction in hydrothermal reaction kettle, after being down to room temperature, filter or be centrifuged described in obtaining final product
Target the solution of fluorescent carbon point.
Present invention also offers application of the described Mitochondrially targeted fluorescent carbon point in as mitochondria fluorescence probe,
And application of the Mitochondrially targeted fluorescent carbon point in as Mitochondrially targeted anti-cancer medicament carrier.
Carbon point is prepared simply, with fluorescence radiation ability, small size, good water solubility and the low property of bio-toxicity due to it
Matter and be widely used in many fields, such as bio-imaging, biological monitoring and pharmaceutical carrier.Carbon point prepared by the present invention, it is first
The secondary ability realized to the mitochondria imaging of mammalian cell, and the ability of its anti-light bleaching is far above conventional organic point
Sub- dyestuff.Compared to the mitochondria imaging agents of commercialization, the carbon point that we synthesize is due to preparing simple, good water solubility, safety
Property it is good, with low cost, be better able to promote the use of, and be expected to replace commercialization mitochondria fluorescence probe.Simultaneously as carbon point
Surface is existed including amino, carboxyl, sulfydryl and functional group etc. hydroxyl, and the carbon point can be by physically or chemically having acted on
Effect load cancer therapy drug, realization is positioned at mitochondrial targeted drug treatment.The present invention will expand fluorescent carbon point in biomedicine
The application in field.
Present invention mixture first with shitosan, ethylenediamine and dimercaptosuccinic acid as carbon source, using hydrothermal synthesis method one
It is low and new with mitochondria fluorescence imaging and Mitochondrially targeted load medicine function that step is obtained low cost, good water solubility, bio-toxicity
Type fluorescent carbon point.Carried out relatively as standard items using the quinine sulfate solution (quantum yield is 54%) that is dissolved in 0.1M sulfuric acid
Quantum yield is tested, it has been found that the carbon point fluorescence quantum yield is 12%, and can be sent out respectively under different excitation wavelengths
Go out the fluorescence of blue, green and red.The carbon point for preparing is also equipped with the ability to the mitochondria imaging of mammalian cell,
The ability of its anti-light bleaching is far above conventional organic molecule dyestuff.Simultaneously as carbon point surface is existed including amino, carboxylic
The functional groups such as base, sulfydryl and hydroxyl, can realize being based on Mitochondrially targeted medicine by physically or chemically used load medicine
Thing is transported, and this will further widen application of the carbon point in biomedical sector.
Technique effect：Relative to prior art, the present invention has the advantage that：
(1) excellent Mitochondrially targeted imaging performance：It has pervasive to the mitochondrial targeted imaging of mammalian cell
Property, just can be realized under the concentration of 100 μ g/mL to including with pneumonocyte (AT II) and normal group of the liver cell (L02) as representative
Knit cell and the human immunocyte with macrophage (Raw264.7) as representative and with breast cancer cell (MCF-7), liver cancer
The mitochondria imaging of cell (HepG2) and cancer cell that cervical cancer cell (HeLa) is representative, at the same its imaging be capable of achieving to exempt from it is clear
Wash, be that fluorescence imaging operation brings huge simplicity；
(2) excellent Mitochondrially targeted load medicine function：By covalent effect, cancer therapy drug can be connected, resulting carbon point-
Drug composite remains in that carbon point Mitochondrially targeted property in itself, such that it is able to realize being positioned at mitochondrial treatment of cancer
And therefore can be greatly enhanced the anticancer therapeutic of medicine.
(3) excellent photoluminescent property：Obtained carbon point fluorescence intensity is big, and fluorescence excitation spectrum and emission spectrum distribution are equal
It is very wide, so as to greatly widen its range of application to mammalian cell mitochondria image checking.As pharmaceutical carrier
When, carbon point fluorescence in itself can assign the characteristic of drug molecule fluorescent tracing, for the location mechanism for studying medicine provides possibility；
(4) excellent anti-light bleaching power：The carbon point is difficult by photobleaching under laser irradiation, and its photostability is far above
Conventional organic dye molecule such as Rhodamine 123 and MitoTracker series dyes etc., therefore can realize continuous for a long time
Imaging；
(5) biocompatibility higher：Through Cytotoxic evaluation test, the fluorescent carbon point in the concentration of 0.5mg/mL,
The toxicity of normal pneumonocyte and breast cancer cell is remained unchanged very low, remain the survival rate of 80% or so and the above, i.e. carbon point
The property of itself can't cause very strong murder by poisoning to cell, show good biocompatibility；
(6) good water dispersible and stability.Obtained fluorescent carbon point has good water dispersible and stability,
It is adapted to mitochondria imaging and the Mitochondrially targeted application for carrying medicine in aqueous living things system.
(7) preparation method of the present invention is simple, raw material is cheap and easy to get, be capable of achieving a large amount of preparation.
Brief description of the drawings
Fig. 1 is to prepare the synthesis schematic diagram of fluorescent carbon point using the mixture of shitosan, ethylenediamine, dimercaptosuccinic acid；
Fig. 2 is transmission electron microscope (TEM) figure of fluorescent carbon point obtained in the present invention；
Fig. 3 is the UV-visible absorption spectrum of fluorescent carbon point obtained in the present invention；
Fig. 4 is the fluorescence emission spectrogram of compound of fluorescent carbon point obtained in the present invention；
Fig. 5 is the obtained fluorescent carbon point of the present invention for MCF-7 imaging effect figures；
Fig. 6 is the fluorescent carbon point for obtaining of the invention for different cell mitochondrial imaging effect figures；
Fig. 7 is toxicity assessment result figure of the fluorescent carbon point obtained in the present invention for different cells；
Fig. 8 connects sensitising agent RB (RB) gained material (CDs-RB) afterwards for the obtained fluorescent carbon point of the present invention
Transmission electron microscope figure；
Fig. 9 connects sensitising agent RB (RB) gained material (CDs-RB) afterwards for the obtained fluorescent carbon point of the present invention
With carbon point and the UV-visible absorption spectrum of RB；
Figure 10 connects sensitising agent RB (RB) gained material (CDs- afterwards for the obtained fluorescent carbon point of the present invention
RB) with carbon point and the fluorescence emission spectrogram of compound of RB；
Figure 11 connects sensitising agent RB (RB) gained material (CDs- afterwards for the obtained fluorescent carbon point of the present invention
RB) to the mitochondria imaging effect figure of MCF-7 cells；
Figure 12 connects sensitising agent RB (RB) gains confrontation MCF-7 afterwards for the obtained fluorescent carbon point of the present invention
The phototherapy effect figure of cell.
Specific embodiment
Below in conjunction with the accompanying drawings and instantiation, the present invention is furture elucidated, it should be understood that these examples are merely to illustrate this hair
Bright rather than limitation the scope of the present invention, after the present invention has been read, those skilled in the art are to of the invention various etc.
The modification of valency form falls within the application appended claims limited range.
Chitosan molecule amount used is in 10kDa-1000kDa in following examples.
Embodiment 1
The preparation of the present embodiment fluorescent carbon point, comprises the following steps：
(1) preparation of raw material：Shitosan, dimercaptosuccinic acid and ethylenediamine are weighed, makes its mass ratio be 5:2:1, three is complete
CL after dilute hydrochloric acid solution in fully mixing and being transferred to hydrothermal reaction kettle；
(2) react：With 180 DEG C of reaction 24h in hydrothermal reaction kettle, carbon dots solution is formed；
(3) purify：Centrifugation or filtering obtain final product target fluorescent carbon dots solution.
The schematic diagram of the reaction is shown in Fig. 1, and the transmission electron microscope result for preparing gained fluorescent carbon point is shown in Fig. 2, prepares institute
Ultraviolet-the visible absorption spectra for obtaining fluorescent carbon point is shown in Fig. 3, the fluorescent emission under the different wave length of fluorescent carbon point is excited obtained by preparation
Spectrum is shown in Fig. 4.
Embodiment 2 to 9
The preparation process of the fluorescent carbon point of embodiment 2 is same as Example 1, simply shitosan, dimercaptosuccinic acid in step (1)
It is 1 with ethylenediamine three mass ratio:1:1.
The preparation process of the fluorescent carbon point of embodiment 3 is same as Example 1, simply shitosan, dimercaptosuccinic acid in step (1)
It is 1 with ethylenediamine three mass ratio:1:10.
The preparation process of the fluorescent carbon point of embodiment 4 is same as Example 1, simply shitosan, dimercaptosuccinic acid in step (1)
It is 1 with ethylenediamine three mass ratio:10:1.
The preparation process of the fluorescent carbon point of embodiment 5 is same as Example 1, simply shitosan, dimercaptosuccinic acid in step (1)
It is 1 with ethylenediamine three mass ratio:10:10.
The preparation process of the fluorescent carbon point of embodiment 6 is same as Example 1, simply shitosan, dimercaptosuccinic acid in step (1)
It is 20 with ethylenediamine three mass ratio:1:1.
The preparation process of the fluorescent carbon point of embodiment 7 is same as Example 1, simply shitosan, dimercaptosuccinic acid in step (1)
It is 20 with ethylenediamine three mass ratio:1:10.
The preparation process of the fluorescent carbon point of embodiment 8 is same as Example 1, simply shitosan, dimercaptosuccinic acid in step (1)
It is 20 with ethylenediamine three mass ratio:10:1.
The preparation process of the fluorescent carbon point of embodiment 9 is same as Example 1, simply shitosan, dimercaptosuccinic acid in step (1)
It is 2 with ethylenediamine three mass ratio:1:1.
Embodiment 10 to 11
The preparation process of the fluorescent carbon point of embodiment 10 is same as Example 1, and simply in step (2), reaction condition is：
48h is reacted at 160 DEG C.
The preparation process of the fluorescent carbon point of embodiment 11 is same as Example 1, and simply in step (2), reaction condition is：
12h is reacted at 200 DEG C.
Embodiment 12
Fluorescent carbon point obtained by testing example 1 is to the imaging effect of MCF-7 cells, and method is as follows：
(1) cell culture：Recovery MCF-7 cells, in 37 DEG C, 5%CO in RPMI-1640 complete mediums2In environment
Culture, whne cell density it is long to 80% or so when, digested with pancreatin and by Flow cytometry, make thin in final each hole
Born of the same parents' quantity is 5 × 104Individual/mL, still in 37 DEG C, 5%CO224h is cultivated in environment.
(2) cell dyeing：Mitochondrial dye (MitoTracker), endoplasmic reticulum dyestuff (ER Tracker), height are prepared respectively
Dictyosome dyestuff (Golgi Tracker) and lysosome dyestuff (LysoTracker), with carbon point obtained in embodiment 1
Solution mixes, and carbon point concentration is 200 μ g/mL in making mixed liquor.Then, cell is cleaned 2-3 times with phosphate buffer (PBS), plus
Enter the mixing dye liquor that 200 μ L have been prepared, in 37 DEG C, 5%CO230min is incubated in environment altogether.Finally trained completely with RPMI-1640
Base cleaning cell is supported, the dye molecule dissociated in solution is removed.
(3) confocal fluorescent microscope imaging observation：With the laser that wavelength is 488nm, 552nm and 638nm as exciting
Light, wherein carbon point are through 488nm laser excitation transmitting green fluorescences, and mitochondrial dye is red glimmering through 638nm laser excitations transmitting
Light and endoplasmic reticulum dyestuff, golgiosome dyestuff and lysosome dyestuff are through 552nm excitation-emission red fluorescences.Consider above-mentioned dyestuff with
There is certain overlap in carbon point fluorescent emission in itself, therefore shooting condition of each common dye by controlling during single dyeing, protect
Card carbon point under corresponding shooting condition will not occur colour contamination phenomenon from different organelle dyestuffs, to ensure the accurate of experimental result
Property.
Fluorescence imaging result is shown in Fig. 5.As seen from the figure, the green fluorescence of carbon point is overlapped with the red fluorescence of mitochondrial dye
Together, show that the two has the property of common location, namely carbon point can specifically be targeted to the mitochondria of MCF-7 cells, it is right to realize
Mitochondrial dyeing.
Embodiment 13
Fluorescent carbon point obtained by testing example 1 is to HeLa, the line of HepG2, AT II, L02 and Raw264.7 cell
Plastochondria imaging effect, its method is identical with embodiment 12, and wherein organelle dyestuff only selects the mitochondrial dye to carry out and carbon point
Contaminate altogether.Result such as Fig. 6.As seen from the figure, carbon point obtained by embodiment 1 above-mentioned five kinds of cells are respectively provided with it is excellent it is Mitochondrially targeted into
The performance of picture.
Embodiment 14
The cytotoxicity of the fluorescent carbon point obtained by testing example 1, step is as follows：Select normal pneumonocyte (ATII) and
Breast cancer cell (MCF-7), with 5 × 104Individual/mL cell suspensions are respectively 0,10,20,50,100,200,500 with concentration,
After the fluorescent carbon point of 1000 μ g/mL is incubated 24h, fluorescent carbon point is surveyed to two kinds of poison of cell using MTT detection methods using ELIASA
Property.Result is shown in Fig. 7.Test result indicate that fluorescent carbon point is in working concentration (100 μ g/mL) and (200,500 μ g/mL) above,
Normal cell and cancer cell have the survival rate of 80% and the above, illustrate that the fluorescent carbon point material has good bio-compatible
Property.
Embodiment 15
Fluorescent carbon point (CDs) obtained by testing example 1 is connected chemically with RB (RB's), that is, prepare
CDs-RB, method is as follows.
(1) RB is dissolved in dimethylformamide (DMF), with dicyclohexylcarbodiimide (DCC) and I-hydroxybenzotriazole
(HoBt) according to 1:6:The amount ratio of 6 material is activated 4 hours in room temperature.
(2) RB after will be activated is with carbon o'clock according to 1:10 quality was than room temperature reaction 12 hours.
(3) dialysed 2 days in dimethyl sulfoxide (DMSO) (DMSO) and the mixture of water with the bag filter that molecular weight is 1000.This is anti-
Should the transmission electron microscope figure of gained CDs-RB see Fig. 8, ultraviolet-visible absorption spectra is shown in Fig. 9, fluorescence emission spectrum (with
347nm is excitation wavelength) see Figure 10.As seen from the figure, obtained CDs-RB particle diameters are 30nm or so, and it is glimmering at 418nm
Light transmitting occurs in that the emission peak of carbon point and the emission peak of RB, it was demonstrated that exist between the successful synthesis of CD-RB, and carbon point and RB
Certain FRET phenomenon, the emission peak for causing it that RB can be inspired at 418nm.
Embodiment 16
CDs-RB obtained by testing example 15 is to the Mitochondrially targeted characteristics of MCF-7, and its method is identical with embodiment 13.
Result is shown in Figure 11.As seen from the figure, CDs-RB obtained by embodiment 15 is launched under 488nm exciting lights green fluorescence with
MitoTracker excites launched feux rouges to essentially coincide at 638nm, illustrates that CDs-RB can be selectively targeted in mitochondria
In, successfully maintain carbon point targeting property in itself.
Embodiment 17
The MCF-7 phototherapy effects of the CDs-RB and RB obtained by testing example 15, its method is as follows：
(1) cell culture：Recovery MCF-7 cells, in 37 DEG C, 5%CO in RPMI-1640 complete mediums2In environment
Culture, whne cell density it is long to 80% or so when, digested with pancreatin and by Flow cytometry, when making finally to plant 96 orifice plate
Cell quantity is 5 × 104Individual/mL, still in 37 DEG C, 5%CO224h is cultivated in environment.
(2) cell phototherapy：RB solution and CDs-RB solution are prepared in RPMI-1640 complete mediums, makes both final
The RB concentration for containing is 5 μ g/mL.Cell PBS cells are then used again, are separately added into the RB and CDs- of the 100 above-mentioned preparations of μ L
RB solution in corresponding hole, in 37 DEG C, 5%CO230min is cultivated in environment.Then cleaned with RPMI-1640 complete mediums
2-3 times.5min is irradiated with 532nm laser respectively under varying strength (0,10,20,30,40,50mW), be then transferred to 37 DEG C,
5%CO2Continue to cultivate 4h in environment.
(3) cell survival rate detection：5mg/mL tetrazolium bromides (MTT) is prepared, and adds 10 μ L to prepare in each cell hole
5mg/mL MTT solution, cultivate 4h in 37 DEG C, 5%CO2 environment.The nutrient solution in each hole is then poured out, it is each to add
150 μ L DMSO, finally measure the absorbance at 492nm with ELIASA.Result is shown in Figure 12.
As shown in figure 12, under the intensity of illumination of 30mW, the cell survival rate of CDs-RB groups is very low, 20% or so.This
Illustrate that most cells are dead under the optical dynamic therapy effect of RB.In contrast, even if the cell of RB groups is in 50mW intensity
Laser irradiation under, its cell survival rate still up to more than 90%, illustrate that RB light power curative effects in itself are very poor.Experiment above is demonstrate,proved
Understand application potentials of the CDs-RB on the light power anticancer therapy of targetted mitochondria.
Claims (8)
1. a kind of Mitochondrially targeted fluorescent carbon point, it is characterised in that it is mainly and is made up of the raw material of following weight ratio：
1-10 part of 1-20 part of shitosan, 1-10 part of ethylenediamine and dimercaptosuccinic acid.
2. Mitochondrially targeted fluorescent carbon point according to claim 1, it is characterised in that it is mainly by following weight part ratio
The raw material of example is made：
1-10 part of 1 part of shitosan, 1-10 part of ethylenediamine and dimercaptosuccinic acid.
3. Mitochondrially targeted fluorescent carbon point according to claim 1, it is characterised in that it is mainly by following weight part ratio
The raw material of example is made：
1-10 part of 20 parts of shitosan, 1-10 part of ethylenediamine and dimercaptosuccinic acid.
4. Mitochondrially targeted fluorescent carbon point according to claim 1, it is characterised in that the chitosan molecule amount exists
10kDa-1000kDa。
5. the Mitochondrially targeted fluorescent carbon point preparation method described in any one of claim 1-4, it is characterised in that including following step
Suddenly：Mixed liquor is made by shitosan, ethylenediamine and with dimercaptosuccinic acid, then certain hour is reacted under hydrothermal condition, lowered the temperature, mistake
Filter or centrifugation obtain final product the solution of the targeting fluorescent carbon point.
6. the Mitochondrially targeted fluorescent carbon point preparation method described in claim 5, it is characterised in that comprise the following steps：
(1) weigh shitosan, ethylenediamine and and dimercaptosuccinic acid, wherein shitosan heating for dissolving in dilute hydrochloric acid solution, then
Ethylenediamine and dimercaptosuccinic acid are added into chitosan solution mixing, and mixed liquor is added in hydrothermal reaction kettle；
(2) with 160-200 DEG C of 12-48h of reaction in hydrothermal reaction kettle, after being down to room temperature, filtering or centrifugation obtain final product the targeting
The solution of fluorescent carbon point.
7. application of the Mitochondrially targeted fluorescent carbon point described in any one of claim 1-4 in as mitochondria fluorescence probe.
8. the Mitochondrially targeted fluorescent carbon point described in any one of claim 1-4 is in as Mitochondrially targeted anti-cancer medicament carrier
Application.
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