CN106833629B - 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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- CN106833629B CN106833629B CN201710006129.7A CN201710006129A CN106833629B CN 106833629 B CN106833629 B CN 106833629B CN 201710006129 A CN201710006129 A CN 201710006129A CN 106833629 B CN106833629 B CN 106833629B
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- fluorescent carbon
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 title claims abstract description 67
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- 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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- 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
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- 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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Abstract
The invention discloses a kind of Mitochondrially targeted fluorescent carbon point and its preparation method and application, the fluorescent carbon point mainly be made of the raw material of following weight ratio: 1-20 part of chitosan, 1-10 part of ethylenediamine and with 1-10 part of dimercaptosuccinic acid.And using chitosan, ethylenediamine and dimercaptosuccinic acid as raw material, the carbon dots with excellent photoluminescent property have been made using one step of hydro-thermal method.Compared with the existing technology, the carbon dots, which are not only able to realize, stablizes (bleach-resistant) imaging to the quick, free of cleaning of mammalian cell mitochondria, long-time, light, it is alternatively arranged as carrier and anticancer drug orientation is delivered to mitochondria, to realize the neoplasm targeted therapy based on mitochondria.In addition, the carbon dots also have the advantages that preparation cost is low, water dispersible is good, cytotoxicity is low etc., 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 points and its preparation method and application, belong to Bio-Nano-Materials
Technical field.
Background technique
Either in mammal normal cell either sick cell, mitochondria is all deep with its unique effect
The vital movement for affecting cell, generation and cell energy supply, the production of the calcium signal of cell interior and free radical such as ATP
Raw, Apoptosis regulation and the stable state etc. for maintaining cell interior environment.Since mitochondria has emphatically cell metabolism
The meaning wanted, dysfunction and the diseases such as diabetes, tumour, Parkinson's disease and Alzheimer's disease of mitochondria are sent out
It opens up closely related.Therefore to the observation of quantity, the pattern of mitochondria 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 sensibility, 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 develop corresponding line grain
Body fluorescence probe is current research hotspot.The mitochondria fluorescence probe being commercialized now mainly includes Rhodamine 123, has 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 can produce strong fluorescence signal and endure favor to the fullest extent, but they there is also many disadvantages such as
Complicated, expensive, the poor and photostability of water solubility is poor etc. is synthesized, to limit their application to a certain extent.
At the same time, the Targeted cancer therapy for being positioned at mitochondria is the new approaches of current treating cancer.This is because needle
Mitochondria extremely important for cell activities can effectively be destroyed to the drug of mitochondria to improve drug and kill cancer
The efficiency of cell.Develop mitochondria targeted drug, most common method is to utilize Mitochondrially targeted ligand such as triphenylphosphine (TPP)
Covalent modification is carried out to drug, to assign drug Mitochondrially targeted ability.But since the ligand is more toxic, and its
Itself do not have photoluminescent property, therefore must also usually introduce other fluorescent molecules in the process of modification and just be able to achieve to drug
Fluorescent tracing, but other molecules introduced can reduce the Mitochondrially targeted property of drug after modification.These disadvantages also become this and match
Body is for realizing the Mitochondrially targeted bottleneck transported of drug.Described in synthesis, develops one kind and be provided simultaneously with fluorescence probe and drug
The Mitochondrially targeted molecule of carrier dual function or the importance of nano particle are self-evident.
Summary of the invention
Goal of the invention: in view of the above technical problems, the present invention provides a kind of fluorescent carbon points, and utilize polyamines base chemical combination
Object 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 solution: the present invention provides a kind of Mitochondrially targeted fluorescent carbon points, mainly by following weight ratio
Raw material be made:
1-20 part of chitosan, 1-10 part of ethylenediamine and with 1-10 part of dimercaptosuccinic acid.
It is preferred that the Mitochondrially targeted fluorescent carbon point is mainly made of the raw material of following weight ratio:
1 part of chitosan, 1-10 part of ethylenediamine and with 1-10 part of dimercaptosuccinic acid.
It is preferred that the Mitochondrially targeted fluorescent carbon point is mainly made of the raw material of following weight ratio:
20 parts of chitosan, 1-10 part of ethylenediamine and with 1-10 part of dimercaptosuccinic acid.
It is preferred that the molecular weight of chitosan is in 10kDa-1000kDa.
The present invention also provides the Mitochondrially targeted fluorescent carbon point preparation methods, comprising the following steps: by chitosan, second
Diamines and mixed liquor is made with dimercaptosuccinic acid, certain time is then reacted under hydrothermal condition, cool down, filters or be centrifuged up to institute
State the solution of targeting fluorescent carbon point.
It is preferred that, comprising the following steps:
(1) weigh chitosan, ethylenediamine and and dimercaptosuccinic acid, wherein chitosan dissolves by heating in dilute hydrochloric acid solution,
Ethylenediamine is added with dimercaptosuccinic acid then and is mixed into chitosan solution, and mixed liquor is added in hydrothermal reaction kettle；
(2) it is cooled to room temperature in hydrothermal reaction kettle with 160-200 DEG C of 12-48h of reaction, filters or be centrifuged up to described
Target the solution of fluorescent carbon point.
The present invention also provides the Mitochondrially targeted fluorescent carbon points as the application in mitochondria fluorescence probe,
And the Mitochondrially targeted fluorescent carbon point is as the application in Mitochondrially targeted anti-cancer medicament carrier.
Carbon dots are prepared due to it simply, with fluorescence radiation ability, the property that size is small, good water solubility and bio-toxicity are low
Matter and be widely used in many fields, such as bio-imaging, biological monitoring and pharmaceutical carrier.Carbon dots prepared by the present invention, it is first
The secondary ability for realizing the mitochondria imaging to mammalian cell, and the ability of its anti-light bleaching is much higher than conventional organic point
Sub- dyestuff.Compared to the mitochondria imaging agents of commercialization, the carbon dots that we synthesize are due to preparing simple, good water solubility, safety
Property it is good, low in cost, be better able to promote the use of, and be expected to replace commercialization mitochondria fluorescence probe.Simultaneously as carbon dots
There is can be by physically or chemically having acted on including functional groups, the carbon dots such as amino, carboxyl, sulfydryl and hydroxyls on surface
Effect load anticancer drug realizes the targeted drug treatment for being positioned at mitochondria.The present invention will expand fluorescent carbon point in biomedicine
The application in field.
The present invention utilizes hydrothermal synthesis method one for the first time using the mixture of chitosan, ethylenediamine and dimercaptosuccinic acid as carbon source
It is low and with mitochondria fluorescence imaging and Mitochondrially targeted carry the new of medicine function that at low cost, good water solubility, bio-toxicity is made in step
Type fluorescent carbon point.It is carried out relatively using the quinine sulfate solution (quantum yield 54%) being dissolved in 0.1M sulfuric acid as standard items
Quantum yield test, it has been found that the carbon dots fluorescence quantum yield is 12%, and can be sent out respectively under different excitation wavelengths
Blue, green and red fluorescence out.The carbon dots being prepared are also equipped with the ability of the mitochondria imaging to mammalian cell,
The ability of its anti-light bleaching is much higher than conventional organic molecule dyestuff.Simultaneously as there is include amino, carboxylic on carbon dots surface
The functional groups such as base, sulfydryl and hydroxyl can be realized by physically or chemically used load drug based on Mitochondrially targeted medicine
Object transports, this will further widen carbon dots in the application of field of biomedicine.
Technical effect: compared with the existing technology, present invention has the advantage that
(1) excellent Mitochondrially targeted imaging performance: it has the targeted imaging of mammalian cell mitochondria pervasive
Property, can be realized under the concentration of 100 μ g/mL to include with pneumonocyte (AT II) and liver cell (L02) are representative normal group
Knit cell and with macrophage (Raw264.7) for the human immunocyte of representative and with breast cancer cell (MCF-7), liver cancer
Cell (HepG2) and cervical cancer cell (HeLa) are the mitochondria imaging of the cancer cell of representative, while its imaging can be achieved to exempt from clearly
It washes, brings huge simplicity for fluorescence imaging operation；
(2) by covalent effect, anticancer drug, obtained carbon dots-can excellent Mitochondrially targeted load medicine function: be connected
Drug composite still maintains the Mitochondrially targeted property of carbon dots itself, so as to realize the treatment of cancer for being positioned at mitochondria
And it therefore can greatly improve the anticancer therapeutic of drug.
(3) excellent photoluminescent property: obtained carbon dots fluorescence intensity is big, and fluorescence excitation spectrum and emission spectrum distribution are equal
It is very wide, to greatly widen its application range to mammalian cell mitochondria image checking.As pharmaceutical carrier
When, the fluorescence of carbon dots itself can assign the characteristic of drug molecule fluorescent tracing, provide possibility to study the location mechanism of drug；
(4) excellent anti-light bleaching power: the carbon dots are not easy by photobleaching under laser irradiation, and photostability is much higher than
Conventional organic dye molecule such as Rhodamine 123 and MitoTracker series dyes etc., therefore may be implemented continuous for a long time
Imaging；
(5) higher biocompatibility: testing through Cytotoxic evaluation, the fluorescent carbon point in the concentration of 0.5mg/mL,
It remains unchanged to the toxicity of normal pneumonocyte and breast cancer cell very low, remains 80% or so or more survival rate, i.e. carbon dots
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 suitble to mitochondria imaging and the Mitochondrially targeted application for carrying medicine in aqueous biosystem.
(7) preparation method of the present invention is simple, raw material is cheap and easy to get, a large amount of preparations can be achieved.
Detailed description of the invention
Fig. 1 is to prepare the synthesis schematic diagram of fluorescent carbon point using the mixture of chitosan, ethylenediamine, dimercaptosuccinic acid；
Fig. 2 is transmission electron microscope (TEM) figure of fluorescent carbon point produced by the present invention；
Fig. 3 is the UV-visible absorption spectrum of fluorescent carbon point produced by the present invention；
Fig. 4 is the fluorescence emission spectrogram of compound of fluorescent carbon point produced by the present invention；
Fig. 5 is fluorescent carbon point produced by the present invention for MCF-7 imaging effect figure；
Fig. 6 is the fluorescent carbon point of the invention obtained for different cell mitochondrial imaging effect figures；
Fig. 7 is toxicity assessment result figure of the fluorescent carbon point produced by the present invention for different cells；
Fig. 8 is that fluorescent carbon point produced by the present invention connects photosensitizer Bengal rose red (RB) obtained material (CDs-RB) afterwards
Transmission electron microscope figure；
Fig. 9 is that fluorescent carbon point produced by the present invention connects photosensitizer Bengal rose red (RB) obtained material (CDs-RB) afterwards
With the UV-visible absorption spectrum of carbon dots and RB；
Figure 10 is that fluorescent carbon point produced by the present invention connects photosensitizer Bengal rose red (RB) obtained material (CDs- afterwards
RB) with the fluorescence emission spectrogram of compound of carbon dots and RB；
Figure 11 is that fluorescent carbon point produced by the present invention connects photosensitizer Bengal rose red (RB) obtained material (CDs- afterwards
RB) to the mitochondria imaging effect figure of MCF-7 cell；
Figure 12 be fluorescent carbon point produced by the present invention connect photosensitizer Bengal rose red (RB) afterwards obtained material to MCF-7
The phototherapy effect figure of cell.
Specific embodiment
With reference to the accompanying drawing and specific example, the present invention is furture elucidated, it should be understood that these examples are merely to illustrate this hair
Bright rather than limit the scope of the invention, after the present invention has been read, those skilled in the art are to of the invention various etc.
The modification of valence form falls within the application range as defined in the appended claims.
Molecular weight of chitosan used is in 10kDa-1000kDa in following embodiment.
Embodiment 1
The preparation of the present embodiment fluorescent carbon point, comprising the following steps:
(1) preparation of raw material: weighing chitosan, dimercaptosuccinic acid and ethylenediamine, makes its mass ratio 5:2:1, and three is complete
Fully dissolved is mixed well and is transferred in hydrothermal reaction kettle after dilute hydrochloric acid solution；
(2) it reacts: in hydrothermal reaction kettle for 24 hours with 180 DEG C of reactions, forming carbon dots solution；
(3) it purifies: being centrifuged or filter up to target fluorescent carbon dots solution.
The schematic diagram of the reaction is shown in Fig. 1, and the transmission electron microscope result of preparation 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 excitation of preparation gained fluorescent carbon point
Spectrum is shown in Fig. 4.
Embodiment 2 to 9
The preparation step of 2 fluorescent carbon point of embodiment is same as Example 1, only chitosan, dimercaptosuccinic acid in step (1)
It is 1:1:1 with ethylenediamine three's mass ratio.
The preparation step of 3 fluorescent carbon point of embodiment is same as Example 1, only chitosan, dimercaptosuccinic acid in step (1)
It is 1:1:10 with ethylenediamine three's mass ratio.
The preparation step of 4 fluorescent carbon point of embodiment is same as Example 1, only chitosan, dimercaptosuccinic acid in step (1)
It is 1:10:1 with ethylenediamine three's mass ratio.
The preparation step of 5 fluorescent carbon point of embodiment is same as Example 1, only chitosan, dimercaptosuccinic acid in step (1)
It is 1:10:10 with ethylenediamine three's mass ratio.
The preparation step of 6 fluorescent carbon point of embodiment is same as Example 1, only chitosan, dimercaptosuccinic acid in step (1)
It is 20:1:1 with ethylenediamine three's mass ratio.
The preparation step of 7 fluorescent carbon point of embodiment is same as Example 1, only chitosan, dimercaptosuccinic acid in step (1)
It is 20:1:10 with ethylenediamine three's mass ratio.
The preparation step of 8 fluorescent carbon point of embodiment is same as Example 1, only chitosan, dimercaptosuccinic acid in step (1)
It is 20:10:1 with ethylenediamine three's mass ratio.
The preparation step of 9 fluorescent carbon point of embodiment is same as Example 1, only chitosan, dimercaptosuccinic acid in step (1)
It is 2:1:1 with ethylenediamine three's mass ratio.
Embodiment 10 to 11
The preparation step of 10 fluorescent carbon point of embodiment is same as Example 1, only in step (2), reaction condition are as follows:
48h is reacted at 160 DEG C.
The preparation step of 11 fluorescent carbon point of embodiment is same as Example 1, only in step (2), reaction condition are as follows:
12h is reacted at 200 DEG C.
Embodiment 12
Imaging effect of the fluorescent carbon point obtained by testing example 1 to MCF-7 cell, the method is as follows:
(1) cell culture: recovery MCF-7 cell, in 37 DEG C, 5%CO in RPMI-1640 complete medium2In environment
Culture, when cell density it is long to 80% or so when, digest and pass through Flow cytometry with pancreatin, make in finally each hole carefully
Born of the same parents' quantity is 5 × 104A/mL, still in 37 DEG C, 5%CO2It is cultivated for 24 hours 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 dots obtained in embodiment 1
Solution mixing, makes 200 μ g/mL of carbon dots concentration in mixed liquor.Then, it is cleaned cell 2-3 times, is added with phosphate buffer (PBS)
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
It supports base and cleans cell, remove the dye molecule to dissociate in solution.
(3) confocal fluorescent microscopic imaging observation: use laser that wavelength is 488nm, 552nm and 638nm as excitation
Light, wherein carbon dots emit green fluorescence through 488nm laser excitation, and mitochondrial dye is red glimmering through 638nm laser excitation transmitting
Light and endoplasmic reticulum dyestuff, golgiosome dyestuff and lysosome dyestuff are through 552nm excitation-emission red fluorescence.Consider above-mentioned dyestuff with
There are certain overlappings for the fluorescent emission of carbon dots itself, therefore each total dye is protected by controlling shooting condition when single dyeing
From different organelle dyestuffs colour contamination phenomenon will not occur for card carbon dots under corresponding shooting condition, to guarantee the accurate of experimental result
Property.
Fluorescence imaging result is shown in Fig. 5.As seen from the figure, the green fluorescence of carbon dots and the red fluorescence of mitochondrial dye overlap
Together, show the mitochondria that there is the two the property of common location namely carbon dots can specifically be targeted to MCF-7 cell, realization pair
The dyeing of mitochondria.
Embodiment 13
Fluorescent carbon point obtained by testing example 1 is to HeLa, HepG2, the line of AT II, L02 and Raw264.7 cell
Plastochondria imaging effect, method is identical as embodiment 12, and wherein organelle dyestuff only selects mitochondrial dye to carry out and carbon dots
Dye altogether.As a result such as Fig. 6.As seen from the figure, carbon dots obtained by embodiment 1 to above-mentioned five kinds of cells all have it is excellent it is Mitochondrially targeted at
The performance of picture.
Embodiment 14
The cytotoxicity of fluorescent carbon point obtained by testing example 1, steps are as follows: select normal pneumonocyte (ATII) and
Breast cancer cell (MCF-7), with 5 × 104A/mL cell suspension is respectively 0,10,20,50,100,200,500 with concentration,
After the fluorescent carbon point of 1000 μ g/mL is incubated for for 24 hours, fluorescent carbon point is surveyed to the poison of two kinds of cells using MTT detection method using microplate reader
Property.As a result see Fig. 7.The experimental results showed that fluorescent carbon point is at working concentration (100 μ g/mL) or more (200,500 μ g/mL),
Normal cell and cancer cell have 80% or more survival rate, illustrate that the fluorescent carbon point material has good bio-compatible
Property.
Embodiment 15
Fluorescent carbon point obtained by testing example 1 (CDs) is connected chemically with Bengal rose red (RB's), that is, is prepared
CDs-RB, method are as follows.
(1) RB is dissolved in dimethylformamide (DMF), with dicyclohexylcarbodiimide (DCC) and I-hydroxybenzotriazole
(HoBt) it is activated 4 hours according to the mass ratio of the material of 1:6:6 in room temperature.
(2) RB and carbon dots after will be activated be reacted at room temperature 12 hours according to the mass ratio of 1:10.
(3) it is dialysed 2 days in dimethyl sulfoxide (DMSO) and the mixture of water with the bag filter that molecular weight is 1000.This is anti-
The transmission electron microscope figure of gained CDs-RB is answered to 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 partial size is 30nm or so, glimmering at 418nm
There is the emission peak of carbon dots and the emission peak of RB in light emitting, it was demonstrated that the successful synthesis of CD-RB, and exist between carbon dots and RB
Certain fluorescence resonance energy transfer phenomenon causes it that can inspire the emission peak of RB at 418nm.
Embodiment 16
For CDs-RB obtained by testing example 15 to the Mitochondrially targeted characteristic of MCF-7, method is identical as embodiment 13.
The result is shown in Figure 11.As seen from the figure, CDs-RB obtained by embodiment 15 is emitted under 488nm exciting light green fluorescence with
MitoTracker excites emitted feux rouges to essentially coincide at 638nm, illustrates that CDs-RB can be selectively targeted in mitochondria
In, successfully maintain the targeting property of carbon dots itself.
Embodiment 17
The MCF-7 phototherapy effect of CDs-RB obtained by testing example 15 and RB, method are as follows:
(1) cell culture: recovery MCF-7 cell, in 37 DEG C, 5%CO in RPMI-1640 complete medium2In environment
Culture, when cell density it is long to 80% or so when, Flow cytometry is digested and passed through with pancreatin, when making final kind of 96 orifice plate
Cell quantity is 5 × 104A/mL, still in 37 DEG C, 5%CO2It is cultivated for 24 hours in environment.
(2) cell phototherapy: preparing RB solution and CDs-RB solution in RPMI-1640 complete medium, keeps the two final
The RB concentration contained is 5 μ g/mL.Cell then is cleaned with cell PBS again, is separately added into the RB and CDs- of the 100 above-mentioned preparations of μ L
RB solution is in corresponding hole, in 37 DEG C, 5%CO230min is cultivated in environment.Then cleaned with RPMI-1640 complete medium
2-3 times.Irradiate 5min respectively under varying strength (0,10,20,30,40,50mW) with 532nm laser, be then transferred to 37 DEG C,
5%CO2Continue to cultivate 4h in environment.
(3) cell survival rate detects: preparing 5mg/mL thiazolyl blue (MTT), and 10 μ L are added in each cell hole and prepare
5mg/mL MTT solution, cultivate 4h in 37 DEG C, 5%CO2 environment.The culture solution in each hole is then poured out, it is each to be added
150 μ L DMSO finally measure the absorbance at 492nm with microplate reader.The 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 group 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 group is in 50mW intensity
Laser irradiation under, cell survival rate still be up to 90% or more, illustrate that the light power curative effect of RB itself is very poor.The above experiment card
Application potential of the CDs-RB on the light power anticancer therapy of targetted mitochondria is illustrated.
Claims (8)
1. a kind of Mitochondrially targeted fluorescent carbon point, which is characterized in that it is made of the raw material of following weight ratio:
1-20 part of chitosan, 1-10 part of ethylenediamine and 1-10 part of dimercaptosuccinic acid；
Mixed liquor is made by chitosan, ethylenediamine and with dimercaptosuccinic acid, certain time is then reacted under hydrothermal condition, cools down,
It filters or is centrifuged up to the solution of the targeting fluorescent carbon point.
2. Mitochondrially targeted fluorescent carbon point according to claim 1, which is characterized in that it is by following weight ratio
Raw material is made:
1 part of chitosan, 1-10 part of ethylenediamine and 1-10 part of dimercaptosuccinic acid.
3. Mitochondrially targeted fluorescent carbon point according to claim 1, which is characterized in that it is by following weight ratio
Raw material is made:
20 parts of chitosan, 1-10 part of ethylenediamine and 1-10 part of dimercaptosuccinic acid.
4. Mitochondrially targeted fluorescent carbon point according to claim 1, which is characterized in that the molecular weight of chitosan exists
10kDa-1000kDa。
5. the described in any item Mitochondrially targeted fluorescent carbon point preparation methods of claim 1-4, which is characterized in that including following step
It is rapid: mixed liquor is made by chitosan, ethylenediamine and with dimercaptosuccinic acid, certain time is then reacted under hydrothermal condition, cools down, mistake
It filters or is centrifuged up to the solution of the targeting fluorescent carbon point.
6. Mitochondrially targeted fluorescent carbon point preparation method described in claim 5, which comprises the following steps:
(1) weigh chitosan, ethylenediamine and and dimercaptosuccinic acid, wherein chitosan dissolves by heating in dilute hydrochloric acid solution, then
Ethylenediamine is added with dimercaptosuccinic acid and is mixed into chitosan solution, and mixed liquor is added in hydrothermal reaction kettle；
(2) it is cooled to room temperature in hydrothermal reaction kettle with 160-200 DEG C of 12-48h of reaction, filters or be centrifuged up to the targeting
The solution of fluorescent carbon point.
7. the described in any item Mitochondrially targeted fluorescent carbon points of claim 1-4 are as the application in mitochondria fluorescence probe.
8. the described in any item Mitochondrially targeted fluorescent carbon points of claim 1-4 are in as Mitochondrially targeted anti-cancer medicament carrier
Application.
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| CN110161005B (en) * | 2019-05-24 | 2021-08-27 | 郑州大学 | Fluorescent carbon dot for detecting cell activity, preparation method and application thereof |
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| CN113548656B (en) * | 2020-06-16 | 2023-02-21 | 哈尔滨成程生命与物质研究所 | Carbon dots with anticancer bioactivity and preparation method thereof |
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| CN115340867B (en) * | 2022-08-30 | 2023-10-31 | 东南大学 | Preparation method of green fluorescent carbon dots GB-CDs and Fe in detection mitochondria 3+ And the use of ATP |
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