CN106367065B - The preparation method and its usage of copper, nitrogen-doped carbon quantum dot with dual light treatment effect and fluorescence imaging - Google Patents
The preparation method and its usage of copper, nitrogen-doped carbon quantum dot with dual light treatment effect and fluorescence imaging Download PDFInfo
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- CN106367065B CN106367065B CN201610735226.5A CN201610735226A CN106367065B CN 106367065 B CN106367065 B CN 106367065B CN 201610735226 A CN201610735226 A CN 201610735226A CN 106367065 B CN106367065 B CN 106367065B
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 title claims abstract description 32
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 229910052802 copper Inorganic materials 0.000 title claims abstract description 24
- 239000010949 copper Substances 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 230000000694 effects Effects 0.000 title claims abstract description 14
- 238000000799 fluorescence microscopy Methods 0.000 title claims abstract description 13
- 230000009977 dual effect Effects 0.000 title claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- 235000019301 disodium ethylene diamine tetraacetate Nutrition 0.000 claims abstract description 9
- MPTQRFCYZCXJFQ-UHFFFAOYSA-L copper(II) chloride dihydrate Chemical compound O.O.[Cl-].[Cl-].[Cu+2] MPTQRFCYZCXJFQ-UHFFFAOYSA-L 0.000 claims abstract description 8
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 claims abstract description 7
- 239000003109 Disodium ethylene diamine tetraacetate Substances 0.000 claims abstract description 6
- 238000000502 dialysis Methods 0.000 claims description 11
- 239000000706 filtrate Substances 0.000 claims description 7
- 238000001027 hydrothermal synthesis Methods 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 229910001431 copper ion Inorganic materials 0.000 claims description 2
- 238000004108 freeze drying Methods 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 239000000047 product Substances 0.000 claims description 2
- 239000006228 supernatant Substances 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 abstract description 9
- 238000002560 therapeutic procedure Methods 0.000 abstract description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 8
- 229910052760 oxygen Inorganic materials 0.000 abstract description 8
- 239000001301 oxygen Substances 0.000 abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 7
- 238000010521 absorption reaction Methods 0.000 abstract description 3
- 238000007626 photothermal therapy Methods 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- 238000003384 imaging method Methods 0.000 abstract description 2
- 208000017983 photosensitivity disease Diseases 0.000 abstract description 2
- 231100000434 photosensitization Toxicity 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 30
- 238000010438 heat treatment Methods 0.000 description 6
- 206010028980 Neoplasm Diseases 0.000 description 4
- ZKSVYBRJSMBDMV-UHFFFAOYSA-N 1,3-diphenyl-2-benzofuran Chemical compound C1=CC=CC=C1C1=C2C=CC=CC2=C(C=2C=CC=CC=2)O1 ZKSVYBRJSMBDMV-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000007710 freezing Methods 0.000 description 3
- 230000008014 freezing Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- 239000003643 water by type Substances 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 238000009738 saturating Methods 0.000 description 2
- 235000003140 Panax quinquefolius Nutrition 0.000 description 1
- 240000005373 Panax quinquefolius Species 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000029918 bioluminescence Effects 0.000 description 1
- 238000005415 bioluminescence Methods 0.000 description 1
- 239000003575 carbonaceous material Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 229940124274 edetate disodium Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 208000021760 high fever Diseases 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000001699 photocatalysis Effects 0.000 description 1
- 238000007146 photocatalysis Methods 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 239000002096 quantum dot Substances 0.000 description 1
- 239000003642 reactive oxygen metabolite Substances 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- 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
- A61K41/00—Medicinal preparations obtained by treating materials with wave energy or particle radiation ; Therapies using these preparations
- A61K41/0052—Thermotherapy; Hyperthermia; Magnetic induction; Induction heating therapy
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K41/00—Medicinal preparations obtained by treating materials with wave energy or particle radiation ; Therapies using these preparations
- A61K41/0057—Photodynamic therapy with a photosensitizer, i.e. agent able to produce reactive oxygen species upon exposure to light or radiation, e.g. UV or visible light; photocleavage of nucleic acids with an agent
-
- 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
- A61K49/0019—Fluorescence in vivo characterised by the fluorescent group, e.g. oligomeric, polymeric or dendritic molecules
-
- 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
- A61K49/0065—Preparation for luminescence or biological staining characterised by a special physical or galenical form, e.g. emulsions, microspheres the luminescent/fluorescent agent having itself a special physical form, e.g. gold nanoparticle
- A61K49/0067—Preparation for luminescence or biological staining characterised by a special physical or galenical form, e.g. emulsions, microspheres the luminescent/fluorescent agent having itself a special physical form, e.g. gold nanoparticle quantum dots, fluorescent nanocrystals
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y40/00—Manufacture or treatment of nanostructures
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- C—CHEMISTRY; METALLURGY
- 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
- C09K11/0883—Arsenides; Nitrides; Phosphides
Abstract
The present invention discloses a kind of copper with dual light treatment effect and fluorescence imaging, the preparation method and its usage of nitrogen-doped carbon quantum dot, the carbon quantum dot prepared can emit blue-fluorescence, while can realize the effect of photo-thermal, optical dynamic therapy and fluorescence imaging.The preparation method is using the carbon quantum dot of disodium EDTA, the copper that Copper dichloride dihydrate is prepared as raw material, N doping.Raw material of the present invention is cheap and easy to get, prepare it is simple, and products obtained therefrom have good biocompatibility and water solubility, can emit blue-fluorescence, infrared and near infrared region have absorption and with preferable photothermal conversion efficiency, have photosensitization and active oxygen can be generated under the irradiation of near infrared light and be used for optical dynamic therapy.The carbon quantum dot of copper, N doping prepared by the present invention has broad application prospects in photo-thermal therapy, optical dynamic therapy, bio-imaging etc..
Description
Technical field
It is specifically a kind of that there is dual light treatment effect the present invention relates to photo-thermal, optical dynamic therapy and fluorescence imaging material
And the preparation method and its usage of the copper of fluorescence imaging, nitrogen-doped carbon quantum dot.
Background technology
Carbon quantum dot was found by the scientist of Clemson University of the U.S. for the first time in 2004, with traditional semiconductor quantum
Point compare, carbon quantum dot have many advantages, such as shine it is more stable, be easier to functionalization and preferably water solubility.Carbon quantum dot remains
The advantages that small toxicity of carbon material, good biocompatibility, makes it in the side such as cell Cheng Xiang ﹑ Sheng object Chuan Gan ﹑ pharmaceutical carriers, photocatalysis
Face possesses great application prospect.Some can be obtained with novel capabilities by adulterating the elements such as nitrogen, sulphur to carbon quantum dot
Carbon quantum dot.It is controlled as the Wang Pengfei of Chinese Academy of Sciences's physics in 2015 and chemical technology research institute reports one kind and can be used for photo-thermal
The sulfur doping carbon quantum dot for the treatment of.Metallic element copper has stronger absorption near infrared region, is expected to realize under near infrared light
Photothermal conversion.The carbon quantum dot rare report at present of copper, N doping, and yet there are no the carbon quantum dot use about copper, N doping
In the research of photo-thermal, optical dynamic therapy.
Invention content
The object of the present invention is to provide a kind of copper can be used in photo-thermal, optical dynamic therapy and fluorescence imaging, nitrogen-doped carbons
Quantum dot can be good at launching stable blue-fluorescence, photo-thermal temperature rise effect can be realized under near infrared light
With light power effect.It can realize the function of photo-thermal, optical dynamic therapy and fluorescence imaging.
The preparation method of a kind of copper with dual light treatment effect and fluorescence imaging, nitrogen-doped carbon quantum dot, is with second
Edetate disodium is carbon source, chelates copper ion, copper, nitrogen-doped carbon quantum dot, preparation method are prepared by hydro-thermal method
Include the following steps：
(1) disodium EDTA, Copper dichloride dihydrate solution are uniformly mixed, obtain mixed liquor, it is spare；
(2) acquired solution filters, and takes filtrate；
(3) hydrothermal reaction kettle reaction is added in gained supernatant, and green solution is obtained after cooling；
(4) it filters, dialysis；
(5) acquired solution is freeze-dried, and is obtained green solid, as product, is kept in dark place.
The molar ratio of disodium EDTA described in step 1) and Copper dichloride dihydrate is 1:1, when mixing
Between be 6-8 h.
Solution described in step 2) filters, and takes filtrate, is by step 1）Gained mixed liquor filters, and takes blue clarification in upper layer saturating
Bright solution.
Reaction condition described in step 3) is 150 DEG C of 3 h of reaction, continues to increase the temperature to 200 DEG C of 3 h of reaction.
It is filtered described in step 4), dialyses, be by step 3）Gained green solution filters, and it is saturating to obtain clear green solutions
Analysis.
It is freeze-dried described in step 5), is by step 4）The solution freeze-drying dialysed, is kept in dark place.
The present invention experiments have shown that：The carbon quantum dot of copper, N doping obtained by above-mentioned preparation is configured to a concentration of 0.5 mg/
The aqueous solution of mL, 1 mg/mL and 2 mg/mL, with 808 nm laser（1W）Irradiation, with the temperature of thermal infrared imager recording solution with
The variation of light application time.The carbon quantum dot solution of three concentration has photo-thermal effect, and concentration dependent is presented.When concentration reaches
It when 1 mg/mL, can heat up under the irradiation of 808 nm laser 31.3 DEG C, it was demonstrated that copper of the invention, nitrogen-doped carbon quantum dot energy
Enough it is applied to photo-thermal therapy.
Active oxygen detection reagent DPBF is added, in near-infrared in the solution that carbon quantum dot obtained by above-mentioned preparation is configured to
Or infrared laser（808 nm）Irradiation under carry out ultraviolet test, with the increase of light application time, DPBF is at 418 nm
Characteristic absorption peak is gradually reduced, this is because caused by DPBF is aoxidized under conditions of active oxygen by active oxygen, experimental result is said
Bright, copper, the nitrogen-doped carbon quantum dot of synthesis have photosensitization, have photodynamic effect under the irradiation of light.
By under the irradiation of the ultraviolet lamp of 365 nm we can significantly see the carbon quantum of the copper of synthesis, N doping
Point can launch stable blue-fluorescence, can apply it to bioluminescence imaging.
Copper of the present invention, nitrogen-doped carbon quantum dot, can be presented photo-thermal, light power effect simultaneously under the irradiation of infrared light,
And have good photo and thermal stability, water solubility and biocompatibility, it is used for the photo-thermal therapy and optical dynamic therapy of tumour, foreground to be wide
It is wealthy, under laser irradiation, luminous energy can be converted to thermal energy, generate high fever, kill cancer cell；Photosensitizer can under laser irradiation
It generates active oxygen and then kills cancer cell to improve the reactive oxygen species of tumor tissues.Under the ultraviolet light of 365 nm
Stable blue-fluorescence can be emitted for fluorescence imaging.
Use condition of the copper, nitrogen-doped carbon quantum dot of the present invention in above-mentioned purposes application, can be according to this field
Known method determines.
It is an advantage of the invention that：（1）Synthetic method is simple, raw material is cheap and easy to get.（2）Copper, the nitrogen-doped carbon quantum of synthesis
Point is provided simultaneously with photo-thermal, optical dynamic therapy effect and fluorescence imaging effect.（3）There are good photo and thermal stability, water solubility and life
Object compatibility.
Specific implementation mode
Principles and features of the present invention are described with reference to embodiments, the given examples are served only to explain the present invention,
It is not intended to limit the scope of the present invention.
Embodiment 1：
1. weighing 3.72 g disodium EDTAs and 1.70 g Copper dichloride dihydrates, 200 mL secondary waters are added
Stirring 6-8 hours.
2. rear blue solution filtering will be stirred to react, blue clear transparent solutions are obtained.
It is reacted 3. solution is added in 25 mL hydrothermal reaction kettles, is warming up to 150 DEG C and reacts 3 hours, be continuously heating to 200 DEG C
Reaction 3 hours, cooled to room temperature obtains green solution.
4. green solution is transferred to beaker, filtrate is dialysed 48 hours, and the molecular cut off of dialysis is 500-1000.
5. liquid freezing is dried after dialysis, obtained green solid is copper, nitrogen-doped carbon quantum dot, is kept in dark place.
The carbon quantum dot of preparation is redissolved in water, is still green solution, having under 365 nm ultraviolet lamps can emit
Blue-fluorescence, and can realize photo-thermal heating under near infrared light and generate active oxygen.
Embodiment 2：
1. weighing 3.72 g disodium EDTAs and 1.70 g Copper dichloride dihydrates, 150 mL secondary waters are added
Stirring 6-8 hours.
2. rear blue solution filtering will be stirred to react, blue clear transparent solutions are obtained.
It is reacted 3. solution is added in 25 mL hydrothermal reaction kettles, is warming up to 150 DEG C and reacts 3 hours, be continuously heating to 200 DEG C
Reaction 3 hours, cooled to room temperature obtains green solution.
4. green solution is transferred to beaker, filtrate is dialysed 48 hours, and the molecular cut off of dialysis is 500-1000.
5. liquid freezing is dried after dialysis, obtained green solid is copper, nitrogen-doped carbon quantum dot, is kept in dark place.
The carbon quantum dot of preparation is redissolved in water, is still green solution, having under 365 nm ultraviolet lamps can emit
Blue-fluorescence, and can realize photo-thermal heating under near infrared light and generate active oxygen.
Embodiment 3：
1. weighing 3.72 g disodium EDTAs and 1.70 g Copper dichloride dihydrates, 250 mL secondary waters are added
Stirring 6-8 hours.
2. rear blue solution filtering will be stirred to react, blue clear transparent solutions are obtained.
It is reacted 3. solution is added in 25 mL hydrothermal reaction kettles, is warming up to 150 DEG C and reacts 3 hours, be continuously heating to 200 DEG C
Reaction 3 hours, cooled to room temperature obtains green solution.
4. green solution is transferred to beaker, filtrate is dialysed 48 hours, and the molecular cut off of dialysis is 500-1000.
5. liquid freezing is dried after dialysis, obtained green solid is copper, nitrogen-doped carbon quantum dot, is kept in dark place.
The carbon quantum dot of preparation is redissolved in water, is still green solution, having under 365 nm ultraviolet lamps can emit
Blue-fluorescence, and can realize photo-thermal heating under near infrared light and generate active oxygen.
Claims (7)
1. the preparation method of a kind of copper with dual light treatment effect and fluorescence imaging, nitrogen-doped carbon quantum dot, feature exist
In using disodium ethylene diamine tetraacetate as carbon source, chelating copper ion is prepared, preparation methods steps include by hydro-thermal method：
(1) disodium EDTA, Copper dichloride dihydrate solution are uniformly mixed, obtain mixed liquor, it is spare；
(2) acquired solution filters, and takes filtrate；
(3) hydrothermal reaction kettle reaction is added in gained supernatant, and green solution is obtained after cooling；
(4) it filters, dialysis；
(5) acquired solution is freeze-dried, and is obtained green solid, as product, is kept in dark place.
2. according to the method described in claim 1, it is characterized in that, disodium EDTA described in step 1) and two
The molar ratio of Hydrated copper chloride is 1:1, the mixing time is 6-8 h.
3. according to the method described in claim 1, it is characterized in that, the filtering of solution described in step 2), takes filtrate, is by step
1）Gained mixed liquor filters, and takes upper layer blue clear transparent solutions.
4. according to the method described in claim 1, it is characterized in that, reaction condition described in step 3) is 150 DEG C of reactions 3
H continues to increase the temperature to 200 DEG C of 3 h of reaction.
5. according to the method described in claim 1, it is characterized in that, being filtered described in step 4), dialysis, is by step 3）Gained
Green solution filters, and obtains clear green solutions dialysis.
6. it is by step 4 according to the method described in claim 1, it is characterized in that, be freeze-dried described in step 5)）Dialysis
The solution freeze-drying crossed, is kept in dark place.
7. the copper of the preparation described in one of claim 1-6, nitrogen-doped carbon quantum dot are applied in fluorescence imaging.
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| CN108165268B (en) * | 2018-01-19 | 2020-12-08 | 北京服装学院 | Preparation of copper ion doped carbon quantum dot, obtained carbon quantum dot and application |
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| CN110151995B (en) * | 2019-06-20 | 2021-10-15 | 广西师范大学 | Targeted copper-doped carbon dot and preparation method and application thereof |
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| CN114988392A (en) * | 2021-02-26 | 2022-09-02 | 临沂市中心医院(临沂市沂水中心医院) | Preparation method of carbon quantum dots with photothermal and photodynamic therapy effects |
| CN115849348B (en) * | 2022-09-16 | 2024-03-15 | 宁波大学 | Nitrogen-copper doped graphene quantum dot, application and device |
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