CN107714724A - A kind of carbon point as antineoplastic and its preparation method and application - Google Patents
A kind of carbon point as antineoplastic and its preparation method and application Download PDFInfo
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- CN107714724A CN107714724A CN201710957649.6A CN201710957649A CN107714724A CN 107714724 A CN107714724 A CN 107714724A CN 201710957649 A CN201710957649 A CN 201710957649A CN 107714724 A CN107714724 A CN 107714724A
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- carbon point
- arginine
- antineoplastic
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- ethylenediamine
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- 229910052799 carbon Inorganic materials 0.000 title claims abstract description 40
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 title claims abstract description 39
- 230000000118 anti-neoplastic effect Effects 0.000 title claims abstract description 21
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 239000004475 Arginine Substances 0.000 claims abstract description 16
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims abstract description 16
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000004090 dissolution Methods 0.000 claims abstract description 3
- 239000002246 antineoplastic agent Substances 0.000 claims description 2
- 229940034982 antineoplastic agent Drugs 0.000 claims description 2
- 206010028980 Neoplasm Diseases 0.000 abstract description 16
- 201000011510 cancer Diseases 0.000 abstract description 16
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract description 9
- 239000003814 drug Substances 0.000 abstract description 6
- 230000000694 effects Effects 0.000 abstract description 6
- 238000000799 fluorescence microscopy Methods 0.000 abstract description 6
- 210000004027 cell Anatomy 0.000 description 18
- AHJXFZUFIJNOAR-WCCKRBBISA-N [C].N[C@@H](CCCNC(N)=N)C(=O)O Chemical compound [C].N[C@@H](CCCNC(N)=N)C(=O)O AHJXFZUFIJNOAR-WCCKRBBISA-N 0.000 description 17
- 235000014852 L-arginine Nutrition 0.000 description 11
- 235000009697 arginine Nutrition 0.000 description 10
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 9
- 229930064664 L-arginine Natural products 0.000 description 9
- 238000000034 method Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 210000004881 tumor cell Anatomy 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000003745 diagnosis Methods 0.000 description 3
- 230000012202 endocytosis Effects 0.000 description 3
- 230000005284 excitation Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000004083 survival effect Effects 0.000 description 3
- 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 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000001576 FEMA 2977 Substances 0.000 description 2
- -1 L-arginine urea carbon Chemical compound 0.000 description 2
- 150000008535 L-arginines Chemical class 0.000 description 2
- 230000031018 biological processes and functions Effects 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 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 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000002189 fluorescence spectrum Methods 0.000 description 2
- 238000003384 imaging method Methods 0.000 description 2
- 230000010354 integration Effects 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000006862 quantum yield reaction Methods 0.000 description 2
- 229960003110 quinine sulfate Drugs 0.000 description 2
- 229910021642 ultra pure water Inorganic materials 0.000 description 2
- 239000012498 ultrapure water Substances 0.000 description 2
- 208000005718 Stomach Neoplasms Diseases 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 150000002171 ethylene diamines Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 206010017758 gastric cancer Diseases 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 231100000225 lethality Toxicity 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000002086 nanomaterial Substances 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000012798 spherical particle Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 201000011549 stomach cancer Diseases 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/44—Elemental carbon, e.g. charcoal, carbon black
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
- A61K31/198—Alpha-amino acids, e.g. alanine or edetic acid [EDTA]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- 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
- A61K49/0089—Particulate, powder, adsorbate, bead, sphere
- A61K49/0091—Microparticle, microcapsule, microbubble, microsphere, microbead, i.e. having a size or diameter higher or equal to 1 micrometer
- A61K49/0093—Nanoparticle, nanocapsule, nanobubble, nanosphere, nanobead, i.e. having a size or diameter smaller than 1 micrometer, e.g. polymeric nanoparticle
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
- A61K9/145—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with organic compounds
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- Bioinformatics & Cheminformatics (AREA)
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Abstract
The present invention relates to a kind of carbon point as antineoplastic and its preparation method and application.Using arginine as carbon source, it is completely dissolved with water, adds appropriate ethylenediamine, ultrasonic dissolution, microwave, which heats, produces target product carbon point.Due to inherently having hydrogen peroxide in cancer cell in organism, so carbon point prepared by the present invention can be used for treating cancer.It can not only fluorescence imaging but also have the characteristics that good biocompatibility, NO burst sizes it is more, effect circulation time it is long, medicine stability is good, cheap and easy to get.
Description
Technical field
The invention belongs to fluorescent nano material and biomedical sector, and in particular to a kind of carbon as antineoplastic
Point and its preparation method and application.
Background technology
NO is a kind of extremely unstable Biological Free Radicals, and molecule is small, simple in construction, is gas under normal temperature, is slightly soluble in water, tool
Have fat-soluble, be distributed widely in organism in each tissue, it is a kind of new bio messenger molecule.And adjusted in the heart, the cerebrovascular
Section, nerve, immunological regulation etc. have highly important biological action.Therefore, by the most attention of people.It is not required to
Any intervening mechanism is wanted quickly to be spread by biomembrane, by information transmission caused by a cell to the cell around it
In, NO biological action and its study on mechanism are in the ascendant, and its discovery indicates inorganic molecule in medical domain
Research Prospects.
In modern biomedical, research finds hydrogen peroxide in tumour cell be present.If it is therefore contemplated that by toward carefully
Arginic method is added in born of the same parents, may be implemented in and NO is produced in tumour cell, so as to kill tumour cell.Although however, smart ammonia
Acid can discharge NO with hydroperoxidation, but its burst size is not very big, and arginine belongs to large biological molecule, in body
Interior to be played a role into the cell by osmosis entrance, inefficient, this also limits its practical application to a certain degree.
The content of the invention
The purpose of the present invention is improved for deficiency existing for existing arginine reaction generation NO technology, will
Arginine, which is made carbon point and imparts its fluorescence property, can carry out fluorescence imaging.And after improveing NO yield it is bigger and can be direct
Entering cell by endocytosis improves efficiency.
To achieve these goals, the technical solution adopted by the present invention is：A kind of carbon point as antineoplastic, prepare
Method comprises the following steps：Using arginine as carbon source, it is completely dissolved with water, adds appropriate ethylenediamine, ultrasonic dissolution, microwave adds
Heat produces target product carbon point.
A kind of above-mentioned carbon point as antineoplastic, described arginine are L arginine.
A kind of above-mentioned carbon point as antineoplastic, in molar ratio, ethylenediamine:Arginine=(1:2)-(1:4)；It is excellent
Choosing, ethylenediamine:Arginine=1:2.
A kind of above-mentioned carbon point as antineoplastic, microwave power 750W, heat time 4min.
Above-mentioned carbon point is alone or is blended in the application prepared in antineoplastic with other antineoplastics.
Carbon point prepared by the present invention with hydrogen peroxide effect in cancer cell by producing NO to kill cancer cell.Carbon point is
Using carbon atom as skeleton structure, size is less than 20nm, has the spherical nano particle of fluorescence property.The invention provides one
Kind can produce NO carbon point with hydroperoxidation, can be used as antineoplastic.The medicine be one not through transpassivation or
Modified carbon point.The fluorescent carbon point can be that it can give birth to the hydroperoxidation in cancer cell as the reason for treating cancer medicine
Into NO, and when the NO contents in cancer cell are higher than 1 μM with regard to that can play a part of killing cancer cell.In addition, the carbon point has
Fluorescence property can realize the diagnosis and treatment integration to cancer.
The beneficial effects of the invention are as follows：
1st, carbon point prepared by the present invention, particle diameter 1-5nm, and be equally distributed spherical particle, carbon point surface does not pass through
Transpassivation or modification, carbon point does not have toxicity, therefore can be used for biomedical sector, is made by itself and hydrogen peroxide in cancer cell
Can effective treating cancer with release NO.
2nd, the antineoplastic based on carbon point of the invention not only can with fluorescence imaging, but also with good biocompatibility,
The features such as NO burst sizes are more, effect circulation time is long, medicine stability is good.Such as in terms of bio-imaging：This fluorescent carbon point is made
With fluorescence imaging and then it can realize that the diagnosis and treatment of cancer are integrated in organism for antineoplastic.In addition, it can also pass through
Endocytosis, which enters cells play effect, makes its therapeutic effect more preferable；Its preparation method technique is simple, easily operated, prepares cost
It is low, it is easy to spread.
3rd, it is of the invention, arginine is made into carbon point, intracellular Fluorescence imaging can be realized and caused NO amounts are bigger, more
Be advantageous to its killing tumor cell.In addition, osmosis effect of the endocytosis of carbon point than arginine in biological cell in itself
Rate is higher, and this is also more conducive to the performance of drug effect.Carbon point prepared by the present invention can as antineoplastic in biomedicine should
With.
Brief description of the drawings
Fig. 1 is the transmission electron microscope imaging of L-arginine carbon point.
Fig. 2 is fluorescence spectrum of the L-arginine carbon point in a length of 370nm of optimum excitation wave.
Fig. 3 is 24 hours L-arginine carbon points and arginic NO release profiles.
Fig. 4 is the cell experiment result of L-arginine carbon point.
Embodiment
The present invention is further described below by way of non-limiting example.
Embodiment 1
11.5mmol L-arginines are weighed respectively, are separately added into 5.7mmol urea and 5.7mmol ethylenediamines, are dissolved in 15mL
In ultra-pure water, after being completely dissolved, the 750W in micro-wave oven, heating is taken out after 4 minutes, respectively obtains L-arginine urea carbon point
And L-arginine ethylenediamine carbon point (LACD) (URCD).
URCD and LACD are respectively added in 90mL pH=6.5 PBS cushioning liquid and dissolved.Take 80mL above-mentioned molten respectively again
Liquid after solution, it is each to add 100 μ L H2O2.Two systems are measured respectively with Griess reagents reacts releasing for NO in 15 hours solution
To one's heart's content condition.As a result it is as shown in table 5.
Table 5
| React 15 hours NO burst sizes (μM) | |
| LACD | 6.5 |
| URCD | 6.3 |
Table 5 be LACD and URCD respectively with H2O2React the statistical result of 15 hours NO burst sizes.LACD ratios as seen from Table 5
The NO amounts of URCD releases are more.The NO amounts that release measures LACD releases for 15 hours are 6.5 μM, and the NO amounts of URCD releases are 6.3 μM.
So preferred ethylenediamine of the present invention.
Embodiment 2
Weigh 2g L-arginines and be dissolved in 15mL with 0.173g, 0.230g, 0.345g, 0.690g, 1.38g ethylenediamine respectively
(ratio of the amount of the material of ethylenediamine and L-arginine is respectively 1 in ultra-pure water:4,1:3,1:2,1:1,2:1), in micro-wave oven
750W takes out after heating 4 minutes, obtains the L-arginine carbon point (LACD) of different ratio.
Five kinds of LACD are dissolved in 40mL pH=6.5 PBS cushioning liquid respectively by more than, then respectively take 20mL again, then divide
200 μ L H are not added thereto2O2Reaction 12 hours.It is measured respectively with Griess reagents reacts 12 hours NO burst size, knot
Fruit is as shown in table 6.
Table 6
| The amount ratio of ethylenediamine and L-arginine material | React 12 hours NO burst sizes (μM) |
| 1:4 | 24.68 |
| 1:3 | 23.46 |
| 1:2 | 28.44 |
| 1:1 | 6.74 |
| 2:1 | 8.28 |
As seen from Table 6, ethylenediamine and the ratio of the amount of L-arginine material are 1:The NO amounts discharged when 2 are most, and burst size is
28.44μM。
The L-arginine carbon point of embodiment 3
2g (11.5mmol) L-arginine is weighed, 0.345g (5.7mmol), is dissolved in 15mL ultra-pure waters, after being completely dissolved,
The 750W in micro-wave oven, heating are taken out after 4 minutes, obtain L-arginine carbon point (LACD).
The L-arginine carbon point (LACD) of preparation is subjected to electron-microscope scanning, as a result as shown in figure 1, it can be seen from figure 1 that preparing
L-arginine carbon point (LACD) average grain diameter is 3nm, and is evenly distributed, into equally distributed spheric granules.
The application of the L-arginine carbon point of embodiment 4
The L-arginine carbon point prepared in embodiment 3 is diluted with water near colourless, be fitted into cuvette, with fluorescence light
Spectrometer measures the carbon point a length of 370nm of optimum excitation wave, is then that 370nm adjusts carbon dots solution in wavelength with ultraviolet specrophotometer
Absorbance to 0.1.Just it is that its is measured at 370nm is glimmering in excitation wavelength with the carbon dots solution of this concentration with sepectrophotofluorometer
Light spectrum, it is identical with this that quinine sulfate fluorescence spectrum measures method, as a result as shown in Fig. 2 due to quinine sulfate standard items quantum
Yield is 54%, so by integrating as can be seen from Figure 2, the quantum yield of L-arginine carbon point (LACD) is 6.88%.
The L-arginine carbon point extracorporeal simulating experiment of embodiment 5
The L-arginine carbon point (LACD) and L-arginine that are prepared in 0.89g embodiments 3 are respectively added into 80mLpH respectively
It is each to add 100 μ L H in=6.5 PBS cushioning liquid2O2, constant temperature stirs at 37 DEG C.Two are measured respectively with Griess reagents
NO release conditions in individual system different time solution.As a result it is as shown in Figure 3.
Fig. 3 is reaction generation NO kinetic release curves.The NO amounts that LACD is discharged than L-arginine as seen from Figure 3 are more
It is more.The NO amounts that release in vitro measures LACD releases for 24 hours are 13.38 μM, and the NO amounts of L-arginine release are 11.12 μM.
The L-arginine carbon point cell experiment of embodiment 6
Take respectively L-arginine carbon point (LACD) prepared by 0.5,1,10,20,50,100,200mg/mL embodiment 3 and
The μ L of L-arginine solution 100 are cultivated 48 hours altogether with BGC823 stomach cancer cells, measure cell survival rate, as a result as shown in Figure 4.From
The visible LACD of Fig. 4 have higher lethality to cancer cell than L-arginine.When drug concentration is 20mg/mL, LACD makes cancer thin
Born of the same parents' survival rate is reduced to 43.1%, and L-arginine carbon point can make cell survival rate bring up to 148.6% on the contrary.
As fully visible, from the point of view of preparation process, method of the invention, low in raw material price, method is simple and easy, and need not
Complicated reaction condition, and carbon point prepared by the present invention can be used for treating cancer.It can not only fluorescence imaging but also
Have the characteristics that good biocompatibility, NO burst sizes are more, effect circulation time is long, medicine stability is good, cheap and easy to get.In view of this
A little outstanding performances, this New Type of Carbon point are expected to carry out application study in the diagnosis and treatment integration field of cancer.
Claims (6)
1. a kind of carbon point as antineoplastic, it is characterised in that preparation method comprises the following steps：Carbon is used as using arginine
Source, it is completely dissolved with water, adds appropriate ethylenediamine, ultrasonic dissolution, microwave, which heats, produces target product carbon point.
2. a kind of carbon point as antineoplastic according to claim 1, it is characterised in that described arginine is L
Arginine.
A kind of 3. carbon point as antineoplastic according to claim 1, it is characterised in that in molar ratio, ethylenediamine:
Arginine=(1:2)-(1:4).
A kind of 4. carbon point as antineoplastic according to claim 3, it is characterised in that in molar ratio, ethylenediamine:
Arginine=1:2.
A kind of 5. carbon point as antineoplastic according to claim 1, it is characterised in that microwave power 750W,
Heat time 4min.
6. the carbon point described in claim any one of 1-4 is alone or is blended in and is prepared in antineoplastic with other antineoplastics
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| CN113548656A (en) * | 2020-06-16 | 2021-10-26 | 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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Cited By (7)
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| CN113548656A (en) * | 2020-06-16 | 2021-10-26 | 哈尔滨成程生命与物质研究所 | Carbon dots with anticancer bioactivity and preparation method thereof |
| 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 |
| CN112546223A (en) * | 2020-12-22 | 2021-03-26 | 福州大学 | Photocatalyst for treating hypoxia tumor nitric oxide and preparation method thereof |
| CN112546223B (en) * | 2020-12-22 | 2022-01-18 | 福州大学 | Photocatalyst for treating hypoxia tumor nitric oxide and preparation method thereof |
| CN112442362A (en) * | 2021-01-22 | 2021-03-05 | 暨南大学 | High-nitric oxide-loading fluorescent carbon dot and preparation method and application thereof |
| CN115252596A (en) * | 2022-07-27 | 2022-11-01 | 辽宁大学 | Manganese dioxide modified carbon quantum dot composite nano-microsphere and preparation method and application thereof |
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