CN110151995A - A kind of targeting Copper-cladding Aluminum Bar carbon dots and its preparation method and application - Google Patents
A kind of targeting Copper-cladding Aluminum Bar carbon dots and its preparation method and application Download PDFInfo
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- CN110151995A CN110151995A CN201910534162.6A CN201910534162A CN110151995A CN 110151995 A CN110151995 A CN 110151995A CN 201910534162 A CN201910534162 A CN 201910534162A CN 110151995 A CN110151995 A CN 110151995A
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Abstract
The present invention discloses a kind of targeting Copper-cladding Aluminum Bar carbon dots and its preparation method and application, and preparation method is that hyaluronic acid and polyethyleneimine are obtained N doping carbon dots through one step hydro thermal method, is then simply mixed to obtain Copper-cladding Aluminum Bar carbon dots with copper ion.Preparation method of the invention is simple, convenient, and materials safety is easy to get, and the Copper-cladding Aluminum Bar carbon dots cytotoxicity of preparation is small, good biocompatibility, has good dispersibility in aqueous solution, has good absorption in the near infrared region, has good photothermal conversion efficiency；With good photosensitization, under the irradiation of near infrared light, active oxygen is generated；And it is able to respond reduced glutathione, restore fluorescence imaging.Copper-cladding Aluminum Bar carbon dots prepared by the present invention can target photo-thermal, the optical dynamic therapy that response tumor microenvironment fluorescence imaging mediates, and have broad application prospects in field of cancer treatment.
Description
Technical field
The present invention relates to biological medicine Material Field, especially a kind of targeting Copper-cladding Aluminum Bar carbon dots and preparation method thereof and answer
With.
Background technique
Tumour light treatment includes photo-thermal therapy (Photothermal therapy, PTT) and optical dynamic therapy
(Photodynamic therapy, PDT).Photo-thermal therapy converts light energy into thermal energy by photothermal conversion agent and melts cancer cell,
Optical dynamic therapy, that is, light power reagent generates the cytotoxic active oxygen of tool under the irradiation of light, then kills cancer cell.Light
The particular advantages such as negligible with selective high, side effect and drug resistance due to it, systemic toxicity is low, and the surface of a wound is small are treated, at
For a kind of very promising novel cancer means.However, this emerging research field there is also some problems and not
Foot.Traditional photo-thermal therapy conversion agent is mainly gold nano-material and carbon nanomaterial, these nano materials generally have cost
It is high, preparation is complicated, there are biological safety hidden danger, photo and thermal stability and tumor-targeting are poor the deficiencies of, greatly limit
Nano material is stated in the practical application in the fields such as light treatment.Therefore, exploitation, which has, prepares simple, at low cost, stable structure, biology
The reliable and novel smooth diagnosis and treatment nano material with certain tumor-targeting of safety has closely become the research of domestic and foreign scholars
Hot spot, and just leading the research boom of a new round.
Carbon dots have excellent water dispersible, high photostability, intrinsic photism, good biocompatibility and easily
In characteristics such as synthesis, extensive concern is caused in field of biomedicine.Copper is as element abundant on the earth, than other your gold
Belong to cheap, copper-based nano preparation has biodegradability, can discharge important micro copper, maintains human health, Er Qietong
Based nano-material has excellent photostability, the surface for being easy to modify and good Photothermal characterisation, causes more and more
Concern.And among these, it using carbon dots and copper ion chela and is efficiently synthesized with multifunctionality by simple, economic method
Copper-based nano material becomes one of the research hotspot of contemporary technical field of material chemistry.
In recent years, the synthesis of multi-functional copper-based nano material achieves significant progress, and largely synthesizes copper-based
Nano material does not all carry out targeting sex modification, this make in application process copper-based nano material could not accurately reach cancer cell position
Set, there are blindness for light treatment process, meanwhile, in relation to Copper-cladding Aluminum Bar carbon dots response tumor microenvironment fluorescence imaging mediate photo-thermal,
Optical dynamic therapy has not been reported.
CN109777408A " a kind of high-fluorescence quantum yield N doping carbon dots and its preparation method and application ", this method with
Citric acid and glutamine are raw material, are only used for Silver detection by N doping carbon dots prepared by microwave method.
CN108822838A " preparation method and application of Copper-cladding Aluminum Bar carbon quantum dot ", this method, which utilizes, has saturation schiff bases
Planar structure Na [Cu (EDTA)] is that the carbon source and doping metals of doping metals carbon quantum dot are transformed into after thermal decomposition process
The Copper-cladding Aluminum Bar carbon quantum dot with graphite-structure of cupric coordination, the quantum dot have high fluorescent yield, kill to Escherichia coli
Bacterium rate is up to 100%.
Therefore, a kind of Copper-cladding Aluminum Bar carbon dots with active targeting are prepared, and it is especially heavy to study its tumour light diagnosis and treatment performance
It wants.
Summary of the invention
The object of the present invention is to provide a kind of targeting Copper-cladding Aluminum Bar carbon dots and its preparation method and application, this method operations
Simply, at low cost, be conducive to the industrialization promotion of Copper-cladding Aluminum Bar carbon dots.
A kind of preparation method of targeting Copper-cladding Aluminum Bar carbon dots of the present invention, comprising the following steps:
S1. it weighs a certain amount of hyaluronic acid and polyethyleneimine is dissolved in distilled water, stir evenly spare；
S2. above-mentioned solution is placed in reaction kettle, carries out hydro-thermal reaction；
S3. by liquid 220 μm of aperture filtering with microporous membrane obtained by hydro-thermal method, N doping carbon dots aqueous solution is obtained；
S4. N doping carbon dots aqueous solution and copper ion are mixed, it is dry after dialysis, obtain final product.
In step S1, hyaluronic acid, the mass ratio of polyethyleneimine and distilled water is 1:2:200.
In step S2, hydrothermal temperature is 180 DEG C, and the reaction time is 6 h.
In step S4, the mass ratio of N doping carbon dots aqueous solution and copper ion is 45:256, and the concentration of copper ion is
0.1mol/L, 72 h of cellulose dialysis bag dialysis that bag filter is 500-1000 with molecular cut off.
It is a further object to provide the Copper-cladding Aluminum Bar carbon dots with targeting being prepared by the above method.
The Copper-cladding Aluminum Bar carbon dots being prepared are studied, the Copper-cladding Aluminum Bar carbon dots that discovery is prepared using the method for the present invention, no
Only there is CD44 receptor target, additionally it is possible to respond tumor microenvironment and realize fluorescence imaging, can be used for preparing photo-thermal, light power is controlled
The material for the treatment of.
The present invention further discloses the Copper-cladding Aluminum Bar carbon dots using the method for the present invention preparation in response tumor microenvironment fluorescence
The application in the material of the photo-thermal, optical dynamic therapy that mediate is imaged.
The targeting Copper-cladding Aluminum Bar carbon dots photo-thermal, optical dynamic therapy material in as the indication of pharmaceutical carrier be
The highly expressed cell carcinoma tumor of CD44.
Further, when the drug is liquid preparation, targeting Copper-cladding Aluminum Bar carbon dots concentration is 200 ~ 400 μ g/ml.
The highly expressed cancer cell of CD44 includes the liver cancer tissue of mouse mastopathy cell, people, light when practical application
It is 5 ~ 10min according to the time.
Hyaluronic acid (hyaluronic acid, HA), a kind of acid mucopolysaccharide have good CD44 receptor target.
And there is most cancer cell CD44 to be overexpressed receptor.The method of the present invention is carbon source precursor using hyaluronic acid, using mild
Hydrothermal synthesis, be effectively retained HA residue so that Copper-cladding Aluminum Bar carbon dots have CD44 receptor target, and have transition metal copper
Distinctive light thermal property, this advantage will greatly enhance it in light diagnosis and treatment and the application of other field.
The invention has the advantages that the raw material sources that (1) this method prepares Copper-cladding Aluminum Bar carbon dots are abundant, cheaply, it is easy to get, and we
Method is simple, convenient, and preparation condition is simple；(2) the Copper-cladding Aluminum Bar carbon dots cytotoxicity being prepared by means of the present invention
It is small, there is good absorption in infrared and near infrared region, there is good photothermal conversion efficiency；In infrared or near infrared light irradiation
Under, active oxygen is generated, there is good photosensitization；In addition also there is good targeting；(3) it makes by means of the present invention
Standby obtained Copper-cladding Aluminum Bar carbon dots are able to respond tumor microenvironment and realize fluorescence imaging；(4) Copper-cladding Aluminum Bar carbon dots prepared by the present invention can
With photo-thermal, the optical dynamic therapy mediated for targeting response tumor microenvironment fluorescence imaging, have in field of cancer treatment wide
Application prospect.
Detailed description of the invention
Fig. 1 be embodiment Copper-cladding Aluminum Bar carbon dots aqueous solution and pure water with light application time comparison temperature variation.
Fig. 2 is the icp ms (ICP) that embodiment Copper-cladding Aluminum Bar carbon dots targeting enters different cells
Quantitative detection copper coin cellulose content figure.
Fig. 3 is that the Copper-cladding Aluminum Bar carbon dots of 1,3 diphenyl isobenzofuran (DPBF) detection embodiment are active under illumination condition
Oxygen generates figure.
Fig. 4 is that the aqueous solution of Copper-cladding Aluminum Bar carbon dots responds glutathione recovery fluorescence pattern.
Specific embodiment
The content of present invention is further described below with reference to embodiment, but is not limitation of the invention.
Prepare embodiment 1
The preparation of targeting Copper-cladding Aluminum Bar carbon dots, comprising the following steps:
S1. 100 mg hyaluronic acids and 200 mg polyethyleneimines are weighed, 20 ml distilled water are added, are stirred to dissolve completely
Transparent liquid；
S2. above-mentioned solution is placed in reaction kettle, carries out hydro-thermal reaction, hydrothermal temperature is 180 DEG C, and the reaction time is 6 h；
S3. by liquid 220 μm of aperture filtering with microporous membrane obtained by hydro-thermal method, N doping carbon dots aqueous solution is obtained；
S4. by 20 ml and 0.1 M of N doping carbon dots aqueous solution obtained by S3,20 ml copper ions are mixed, and use molecular cut off
For cellulose dialysis bag 72 h of dialysis of 500-1000, the aqueous solution of the carbon dots of Copper-cladding Aluminum Bar containing targeting is obtained, after freeze-drying, is obtained
To the targeting Copper-cladding Aluminum Bar carbon dots of solid.
Prepare embodiment 2
The preparation of targeting Copper-cladding Aluminum Bar carbon dots, comprising the following steps:
S1. 150 mg hyaluronic acids and 300 mg polyethyleneimines are weighed, 30 ml distilled water are added, are stirred to dissolve completely
Transparent liquid；
S2. above-mentioned solution is placed in reaction kettle, carries out hydro-thermal reaction, hydrothermal temperature is 180 DEG C, and the reaction time is 6 h；
S3. by liquid 220 μm of aperture filtering with microporous membrane obtained by hydro-thermal method, N doping carbon dots aqueous solution is obtained；
S4. by 20 ml and 0.1 M of N doping carbon dots aqueous solution obtained by S3,20 ml copper ions are mixed, and use molecular cut off
For cellulose dialysis bag 72 h of dialysis of 500-1000, the aqueous solution of the carbon dots of Copper-cladding Aluminum Bar containing targeting is obtained, after freeze-drying, is obtained
To the targeting Copper-cladding Aluminum Bar carbon dots of solid.
Prepare embodiment 3
The preparation of targeting Copper-cladding Aluminum Bar carbon dots, comprising the following steps:
S1. 200 mg hyaluronic acids and 400 mg polyethyleneimines are weighed, 40 ml distilled water are added, are stirred to dissolve completely
Transparent liquid；
S2. above-mentioned solution is placed in reaction kettle, carries out hydro-thermal reaction, hydrothermal temperature is 180 DEG C, and the reaction time is 6 h；
S3. by liquid 220 μm of aperture filtering with microporous membrane obtained by hydro-thermal method, N doping carbon dots aqueous solution is obtained；
S4. by 20 ml and 0.1 M of N doping carbon dots aqueous solution obtained by S3,20 ml copper ions are mixed, and use molecular cut off
For cellulose dialysis bag 72 h of dialysis of 500-1000, the aqueous solution of the carbon dots of Copper-cladding Aluminum Bar containing targeting is obtained, after freeze-drying, is obtained
To the targeting Copper-cladding Aluminum Bar carbon dots of solid.
Product prepared by above-described embodiment 1 ~ 3 can be well dispersed in aqueous solution, and can be stabilized.
Application Example 1
Above-described embodiment 1 ~ 3 is prepared into resulting targeting Copper-cladding Aluminum Bar carbon dots and is configured to various concentration aqueous solution (concentration of aqueous solution
For 100 μ g/ml -500 μ g/ml), with 650 nm laser (1W/cm-2) irradiation, with the temperature of thermal infrared imager recording solution with
The variation of light application time.Record the result is shown in Figure 1.
It can be seen from Fig. 1 that, when concentration is 400 μ g/ml, targeting Copper-cladding Aluminum Bar carbon dots are molten with the increase of light application time
The temperature of liquid significantly increases, and temperature is increased to 56 DEG C in 10 minutes, and pure water only increased under the conditions of same light is shone less than
1 DEG C, and concentration dependent is presented in the photo-thermal effect of targeting Copper-cladding Aluminum Bar carbon dots.Confirm that the targeting Copper-cladding Aluminum Bar carbon dots of preparation are answered
There is good photo-thermal effect for photo-thermal therapy.
Application Example 2
Above-described embodiment 1 ~ 3 is prepared into resulting targeting Copper-cladding Aluminum Bar carbon dots and is configured to the aqueous solution that concentration is 400 μ g/ml,
Different time sections are added to the highly expressed mouse mastopathy cell of the good CD44 of adhered state (4T1), cervical cancer cell
(HeLa) and the mouse of CD44 low expression is at culture different time in fiber normal cell (L929) cell, is incubated for, and then collects
Cell, and its intracellular copper coin cellulose content is analyzed using icp ms (ICP), analysis result is shown in
Fig. 2.
As seen from Figure 2, the Copper-cladding Aluminum Bar carbon dots of preparation have good targeting to the highly expressed cancer cell of CD44, into
Enter the L929 normal cell that intracellular amount is apparently higher than CD44 low expression.It is good to confirm that the targeting Copper-cladding Aluminum Bar carbon dots of preparation have
Good targeting.
Application Example 3
Above-described embodiment 1 ~ 3 is prepared into resulting targeting Copper-cladding Aluminum Bar carbon dots and is configured to the aqueous solution that concentration is 50 μ g/ml, is added
Enter active oxygen detection reagent DPBF, carries out ultraviolet test under the irradiation of 650 nm laser, test result is shown in Fig. 3.
As seen from Figure 3, with the increase of light application time, characteristic absorption peak of the DPBF at 418 nm is gradually reduced,
This is because caused by DPBF is aoxidized under conditions of active oxygen by active oxygen, the experiment results show that the targeting copper of synthesis is mixed
Miscellaneous carbon dots have photosensitization, have photodynamic effect under the irradiation of light.
Application Example 4
Above-described embodiment 1 ~ 3 is prepared into resulting targeting Copper-cladding Aluminum Bar carbon dots and is configured to the aqueous solution that concentration is 50 μ g/ml, by
A certain amount of reduced glutathione is gradually added, carries out fluorometric investigation, test result is shown in Fig. 4.
As seen from Figure 4, with the increase of reduced glutathione, fluorescence intensity of the Copper-cladding Aluminum Bar carbon dots at 450 nm
It gradually increases, this is because the copper ion in Copper-cladding Aluminum Bar carbon dots is by glutathione reduction, so that carbon dots reply fluorescence.Due to tumour
The contained glutathione of tissue is 2 ~ 10 times higher than normal tissue, therefore the targeting Copper-cladding Aluminum Bar carbon dots prepared have targeting response swollen
The function of tumor microenvironment fluorescence imaging.
Claims (9)
1. a kind of preparation method of targeting Copper-cladding Aluminum Bar carbon dots, it is characterised in that the following steps are included:
S1. it weighs a certain amount of hyaluronic acid and polyethyleneimine is dissolved in distilled water, stir evenly spare；
S2. above-mentioned solution is placed in reaction kettle, carries out hydro-thermal reaction；
S3. by liquid 220 μm of aperture filtering with microporous membrane obtained by hydro-thermal method, N doping carbon dots aqueous solution is obtained；
S4. N doping carbon dots aqueous solution and copper ion are mixed, it is dry after dialysis, obtain final product.
2. the preparation method of targeting Copper-cladding Aluminum Bar carbon dots according to claim 1, it is characterised in that: transparent in step S1
The mass ratio of matter acid, polyethyleneimine and distilled water is 1:2:200.
3. the preparation method of targeting Copper-cladding Aluminum Bar carbon dots according to claim 1, it is characterised in that: in step S2, hydro-thermal
Reaction temperature is 180 DEG C, and the reaction time is 6 h.
4. the preparation method of targeting Copper-cladding Aluminum Bar carbon dots according to claim 1, it is characterised in that: in step S4, nitrogen is mixed
The mass ratio of miscellaneous carbon dots aqueous solution and copper ion is 45:256, and the concentration of copper ion is 0.1mol/L, bag filter retention molecule
72 h of cellulose dialysis bag dialysis that amount is 500-1000.
5. the targeting Copper-cladding Aluminum Bar that the preparation method of the described in any item targeting Copper-cladding Aluminum Bar carbon dots of claim 1-4 is prepared
Carbon dots.
6. application of the targeting Copper-cladding Aluminum Bar carbon dots in the material for preparing photo-thermal, optical dynamic therapy described in claim 5.
7. the photo-thermal that targeting Copper-cladding Aluminum Bar carbon dots according to claim 5 are mediated in response tumor microenvironment fluorescence imaging,
Application in the material of optical dynamic therapy.
8. according to application described in claim 6 and 7, it is characterised in that: the targeting Copper-cladding Aluminum Bar carbon dots are in photo-thermal, light power
In the material for the treatment of as the indication of pharmaceutical carrier be the highly expressed cell carcinoma tumor of CD44.
9. application according to claim 8, it is characterised in that: when the drug is liquid preparation, targeting Copper-cladding Aluminum Bar carbon
Point concentration is 200-400 μ g/ml.
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| CN112998030A (en) * | 2021-03-05 | 2021-06-22 | 中国科学院宁波材料技术与工程研究所 | Application of copper-doped carbon dots in antibacterial product |
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| CN116836700A (en) * | 2023-06-29 | 2023-10-03 | 辽宁大学 | Preparation method of hyaluronic acid modified red light carbon dots HA-R-CDs and application of hyaluronic acid modified red light carbon dots HA-R-CDs in lung cancer cell targeted imaging |
| CN116836700B (en) * | 2023-06-29 | 2024-05-31 | 辽宁大学 | Preparation method of hyaluronic acid modified red light carbon dots HA-R-CDs and application of hyaluronic acid modified red light carbon dots HA-R-CDs in lung cancer cell targeted imaging |
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| CN116836700A (en) * | 2023-06-29 | 2023-10-03 | 辽宁大学 | Preparation method of hyaluronic acid modified red light carbon dots HA-R-CDs and application of hyaluronic acid modified red light carbon dots HA-R-CDs in lung cancer cell targeted imaging |
| CN116836700B (en) * | 2023-06-29 | 2024-05-31 | 辽宁大学 | Preparation method of hyaluronic acid modified red light carbon dots HA-R-CDs and application of hyaluronic acid modified red light carbon dots HA-R-CDs in lung cancer cell targeted imaging |
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