CN107661512A - A kind of MnO2Wrap up the nano particle and preparation method and application of poly-dopamine - Google Patents
A kind of MnO2Wrap up the nano particle and preparation method and application of poly-dopamine Download PDFInfo
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- CN107661512A CN107661512A CN201711008869.0A CN201711008869A CN107661512A CN 107661512 A CN107661512 A CN 107661512A CN 201711008869 A CN201711008869 A CN 201711008869A CN 107661512 A CN107661512 A CN 107661512A
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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
- A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
- A61K49/18—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes
- A61K49/1818—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes particles, e.g. uncoated or non-functionalised microparticles or nanoparticles
- A61K49/1821—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes particles, e.g. uncoated or non-functionalised microparticles or nanoparticles coated or functionalised microparticles or nanoparticles
- A61K49/1824—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes particles, e.g. uncoated or non-functionalised microparticles or nanoparticles coated or functionalised microparticles or nanoparticles coated or functionalised nanoparticles
- A61K49/1878—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes particles, e.g. uncoated or non-functionalised microparticles or nanoparticles coated or functionalised microparticles or nanoparticles coated or functionalised nanoparticles the nanoparticle having a magnetically inert core and a (super)(para)magnetic coating
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- 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
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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
- A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
- A61K49/08—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by the carrier
- A61K49/10—Organic compounds
- A61K49/12—Macromolecular compounds
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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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/51—Nanocapsules; Nanoparticles
- A61K9/5107—Excipients; Inactive ingredients
- A61K9/5115—Inorganic compounds
Abstract
The invention discloses a kind of MnO2Wrap up the nano particle and preparation method and application of poly-dopamine, the nano particle is the poly-dopamine nanoparticle for aoxidizing auto polymerization in the basic conditions by dopamine hydrochloride as photo-thermal core, manganese dioxide is by in-situ reducing in poly-dopamine nanoparticle surface, a kind of core-shell structure of formation.The nano particle has photo-thermal effect and acid-sensitive magnetic resonance imaging function.The invention has the advantages that tumor tissues and normal structure can be distinguished more accurately, more accurate guidance is provided for clinical cancer therapy, while the material also has thermo-optical property, can realize the diagnosis and treatment integration of tumour.
Description
Technical field
The invention belongs to function nano material and its preparing technical field, and in particular to it is a kind of it is new can be in acid condition
It is lower produce magnetic resonance radiography performance and available for tumor thermal therapy core-shell structure function nano material preparation.This is received
Rice material has acid-sensitive magnetic resonance imaging performance, and has good photothermal deformation effect, can use the photo-thermal therapy of tumour.
Background technology
Tumour is one of current maximum killer for threatening human life and health, and its morbidity and mortality is also constantly being climbed
Rise.Almost 22% new cases and 27% cancer mortality case appear in China in the whole world, in face of such severe situation, essence
Accurate effective cancer diagnosis and treatment means are particularly important.The oncotherapy mode clinically commonly used at present is cut for operation
Remove, chemotherapy, radiotherapy, but due to that can not accurately distinguish tumor region and normal region, thus can normal tissue bring injury.
The diagnosis and treatment integration mode for producing therapeutic effect simultaneously therefore, it is possible to precise positioning tumor region has good prospect.
Spatial and temporal resolution and outstanding soft tissue contrast ability of the magnetic resonance imaging (MRI) due to its superelevation, and non-electrical
The routine clinical non-invasive diagnosing instrument used is had developed into the advantages that harmless to human body from radiation.However, magnetic resonance into
As sensitivity is relatively low, it is therefore desirable to which contrast agent improves contrast in tissue.Current clinical contrast agent is organic molecule gadolinium
Agent（Such as magnevist）, regrettably, this small molecule contrast preparation has very short blood halflife, it is necessary to heavy dose of use,
In the presence of potential Toxicity of Kidney.At present, the inorganic nano contrast agent with magnetic resonance radiography ability causes grinding extensively for educational circles
Study carefully, more accurately distinguish tumor tissues and normal structure, there is huge meaning in clinical guidance oncotherapy.
Photo-thermal therapy technology is as a kind of new ideas of cancer therapy, the organic photoactive molecular with photothermal conversion ability
Or inorganic nano material can be converted into heat under near infrared light and play a variety of antitumor actions, including heating ablation is made
With, overcome chemotherapy resistance to act on and suppress the effect such as metastases.It is mostly some organic light to be presently available for tumor photo-thermal preparation
Sensitive molecule or some inorganic material, but the shortcomings that certain all be present, for example organic photoactive molecular has very short blood halflife
And be unable to selective enrichment in knurl area, inorganic material there is also biocompatibility it is bad the shortcomings of, these shortcomings constrain existing
There is the application of photo-thermal preparation.
The content of the invention
A kind of MnO that the purpose of the present invention is in view of the shortcomings of the prior art and provided2Wrap up the nanometer of poly-dopamine
Grain and preparation method and application, its nano particle utilize the photothermal deformation performance of poly-dopamine, produced under near infrared light
Heat killing tumor cell, be decomposed into acid condition using manganese dioxide the bivalent manganese with magnetic resonance radiography performance from
Son, specific imaging is carried out to tumor locus.
Realizing the concrete technical scheme of the object of the invention is：
A kind of MnO2Wrap up poly-dopamine nano particle, feature be the nano particle be by monomer dopamine in the basic conditions
The poly-dopamine nanoparticle that oxidation auto polymerization obtains is as kernel, potassium permanganate in the solution containing poly-dopamine nano particle
Its surface is that manganese dioxide wraps up poly-dopamine nanoparticle as shell by in-situ reducing, forms the nano particle of core shell structure；
The particle diameter of the poly-dopamine nanoparticle is 80-120nm；In 1W/cm2, under 808nm laser irradiation, concentration is 1mg/mL's
1-15 DEG C of heating in poly-dopamine nanoparticle aqueous solution 1-5min；Manganese dioxide layer is 2-5nm；In neutral conditions, titanium dioxide
Stable state is presented in manganese, and manganese is+4 valencys, and without magnetic resonance radiography performance, in acid condition, manganese dioxide is dissociated into+divalent,
Formed with good magnetic resonance radiography, the manganese ion of+divalent is a kind of metal ion for magnetic resonance radiography.
A kind of preparation method of above-mentioned nano particle, this method include step in detail below：
（1）Dopamine hydrochloride is dissolved in deionized water, 45-55 DEG C of water-bath 10-20min, it is 1mol/L to rapidly join concentration
Sodium hydrate aqueous solution, 45-50 DEG C of open stirring 4-5h, centrifuge and produce poly-dopamine（Polydopamine,PDA）Receive
The grain of rice；Wherein, bar amine hydrochlorate, deionized water, 1mol/L sodium hydrate aqueous solution mass ratio are：150-180mg:70-
100g:600-800mg；
（2）Obtained poly-dopamine nanoparticle is scattered in deionized water, adjusts system pH=6-7 with watery hydrochloric acid, ultrasound adds
Enter potassium permanganate, 35-55 DEG C, magnetic agitation 2-8h, centrifuge the poly-dopamine for producing manganese dioxide parcel（PDA@MnO2）
Nano particle, wherein, poly-dopamine nanoparticle, deionized water, potassium permanganate mass ratio are：20-40mg:20-50g:10-
20mg。
A kind of application of above-mentioned nano particle in tumour magnetic resonance imaging and photo-thermal therapy medicine is prepared.
The poly-dopamine nanoparticle of the present invention is obtained by the alkaline oxygenated auto polymerization of monomer dopamine hydrochloride, and described is poly-
Dopamine nanoparticle is kernel, and because its surface carries the amido and hydroxyl of reproducibility, potassium permanganate is gone back on its surface by original position
Originally it was manganese dioxide, and formed the poly-dopamine of manganese dioxide parcel（PDA@MnO2）Nano particle, the nano particle have acidity
Specific magnetic resonance imaging and light thermal property.
Beneficial effects of the present invention：
The manganese dioxide of the poly-dopamine nano particle, in neutral conditions surface of the manganese dioxide parcel of the present invention, stabilization is not
Dissociation, without magnetic resonance radiography performance, in acid condition, the manganese dioxide dissociation generation+divalent manganese ion on surface has magnetic
Resonate radiography performance, is compared with existing magnetic resonance contrast agent, present invention utilizes material, and performance can occur in acid condition
The characteristics of change, it can more accurately distinguish the tumor region and normal structure of subacidity.The poly-dopamine nanoparticle of kernel
A kind of organic molecule is polymerized, and has good biocompatibility and light thermal property, is that 808nm is closely red in wavelength
Under outer laser irradiation, photo-thermal effect is produced, kills cancer cell.The structure design is a kind of controlling for preferably tumour diagnosis and treatment integration
Treatment scheme.
Brief description of the drawings
Fig. 1 is PDA@MnO2Transmission electron microscope photo（Scale is 100nm）With manganese, the element mapping photo figures of oxygen；
Fig. 2 is PDA@MnO2It is hydrated grain-size graph；
Fig. 3 is PDA and PDA@MnO2UV-visible spectrum；
Fig. 4 is the PDA@MnO of PBS solution and various concentrations2808nm 1W/cm2 irradiation under heating curve in 5min
Figure；
Fig. 5 is the PDA@MnO under condition of different pH2Magnetic resonance T1 weighted imaging figures；
Fig. 6 is the PDA MnO made according to Fig. 52Magnetic resonance T1 weighting relaxation rate；
Fig. 7 is the 4T1 cellular uptake PDA@MnO of Laser Scanning Confocal Microscope shooting2Image；
The cell survival rate chart that Fig. 8 is measured by mtt assay.
Embodiment
In order to be better understood from the present invention, below by embodiment, the present invention is furture elucidated, but present invention is not
It is limited only to following instance.
Embodiment 1
Poly-dopamine（PDA）The preparation of nanoparticle：
（1）180mg dopamine hydrochlorides are dissolved in 90mL water, 50 DEG C of water-bath 20min, it is 1mol/ to rapidly join 760 μ L concentration
L sodium hydrate aqueous solution, 50 DEG C of open stirring 5h；
（2）Above-mentioned system 15000rpm is centrifuged into 10min, abandons supernatant, by precipitation ultrasonic disperse in water, 15000rpm centrifugations
10min, it is repeated 3 times, produces poly-dopamine（Polydopamine, PDA）Nanoparticle.
Embodiment 2
The poly-dopamine of manganese dioxide parcel（PDA@MnO2）The preparation of nano particle：
（1）20mgPDA nanoparticles are taken to be scattered in 20mL water, it is neutral to adjust the system with 0.1mol/L watery hydrochloric acid；
（2）Take 20mg potassium permanganate, be dissolved in 5mL water, be slowly added dropwise under ultrasound condition into（1）In system；
（3）Will（2）40 DEG C of water-baths of system, magnetic agitation 4h；
（4）Above-mentioned system 15000rpm is centrifuged into 10min, abandons supernatant, by precipitation ultrasonic disperse in water, 15000rpm centrifugations
10min, it is repeated 3 times, produces the poly-dopamine of manganese dioxide parcel（PDA@MnO2）Nano particle.
Embodiment 3
The transmission electron microscope of material characterizes：
Refering to Fig. 1, by 1mg/L PDA@MnO2Sample aqueous solution is dropped on copper mesh, treats that sample is completely dried, for transmitted electron
Microscope characterizes.A is the transmission electron microscope photo of PDA nano particles in figure, it can be seen that grain diameter is in 100nm or so；B is
PDA@MnO2Transmission electron microscope photo, it can be seen that material surface restores 2-5nm MnO2Layer, in single dispersing；Scheme C, D, E points
Not Wei the white fields of element mapping, manganese element, oxygen element photo, manganese element, oxygen element are contained in display material surface.
Embodiment 4
The hydration diameter characterization of material：
Refering to Fig. 2, by 1mg/L PDA@MnO2Sample aqueous solution ultrasound is uniform, with Malvern laser particle analyzer determination sample
It is hydrated particle size（DLS）And distribution, it can be seen that material is uniformly dispersed in aqueous, particle diameter is mainly distributed on
80-120nm sections.
Embodiment 5
The ultraviolet-visible spectrum analysis of material：
Refering to Fig. 3, PDA, PDA@MnO2Ultraviolet-visible spectrum.
Embodiment 6
The aqueous solution heating curve of material：
Refering to Fig. 4, l mL PBS, 0.5mg/mL PDA@MnO are taken respectively2、1mg/mL PDA@MnO2In test tube, 1W/cm is used2
808nm near-infrareds irradiation 5min, temperature-rise period is recorded by thermal imaging camera, and draws heating curve.
Embodiment 7
The acid magnetic resonance imaging performance characterization of material：
With the PBS of pH=7.4 or pH=6 by PDA@MnO2Mother liquor 0.25mM（The substance withdrawl syndrome of manganese element）Equal proportion
Dilution 5 times, 2 times are diluted every time, stand the magnetic resonance T1 weighted imagings of measurement material after 4h, such as Fig. 5.And T1 relaxation is made respectively
Rate image, such as Fig. 6, in r1=0.128 of the material of pH=7.4, in r1=4.2 of the material of pH=6, the results showed that PDA@MnO2With acid
Property condition enhancing magnetic resonance radiography performance.
Embodiment 8
The cellular uptake experiment of material：
Take 2mg PDA@MnO2The 5mL aqueous solution and 1mg fluorescein isothiocynates（FITC）0.5mL stirs 12h, and centrifugation washing is
Fluorescent dye FITC PDA@MnO must be loaded2.It is resuspended in 10mL complete mediums（DMEM+10%FBS+1%S/P）It is standby.
By the 4T1 cells that density is 7*103/mL, take cell suspension 1mL to add and be copolymerized in burnt ware, 37 DEG C, 5%CO2、
Under saturated humidity, with nutrient solution is changed after complete medium culture 24h, the PDA MnO for being loaded with FITC are added2（200μg/mL）
Continue to cultivate 2h, remove nutrient solution, with PBS cell 3 times, cell 15min is fixed with 4% paraformaldehyde, contaminated with DAPI thin
Karyon 10min, and use PBS.By intake situation of the confocal microscopy cell to nano particle, as shown in fig. 7,
A figures are blue-fluorescence（DAPI）Passage, B figures are green fluorescence（FITC）Passage, C figures are the superposition of above-mentioned two fluorescence channel.
As shown in FIG., nucleus is dyed to blueness, and green fluorescence is filled with cytoplasm, illustrates that material can be effectively by 4T1 cells
Intake.
Embodiment 9
The photo-thermal cell killing experiment of material：
96 orifice plates are taken to add 100 μ L 4T1 cell suspensions per hole（1*104 cell）, after cultivating 24 hours, add different
The PDA@MnO of concentration2, every kind of two groups of concentration setting, respectively irradiation group and non-irradiation group, continue culture 24 hours, irradiation group
Use 1W/cm2808nm near-infrareds irradiate 5 minutes, non-irradiation group does not process, then carry out MTT cell survival rate analyses.Knot
For fruit as shown in figure 8, irradiation group cell is not that obvious death does not occur, this surfacing does not have obvious cytotoxicity in itself,
With the raising of material concentration, more and more obvious death occurs irradiation group for cell, and this surfacing has good photo-thermal effect
Fruit, there is the oncotherapy effect that can be expected.
Claims (3)
- A kind of 1. MnO2Wrap up the nano particle of poly-dopamine, it is characterised in that the nano particle is in alkalescence by monomer dopamine Under the conditions of the obtained poly-dopamine nanoparticle of oxidation auto polymerization as kernel, potassium permanganate containing poly-dopamine nano particle Its surface is that manganese dioxide wraps up poly-dopamine nanoparticle as shell by in-situ reducing in solution, forms the nanometer of core shell structure Particle；The particle diameter of the poly-dopamine nanoparticle is 80-120nm；In 1W/cm 2, under 808nm laser irradiation, concentration 1mg/ 1-15 DEG C of heating in mL poly-dopamine nanoparticle aqueous solution 1-5min；Manganese dioxide layer is 2-5nm；In neutral conditions, two Stable state is presented in manganese oxide, and manganese is+4 valencys, and without magnetic resonance radiography performance, in acid condition, manganese dioxide is dissociated into+ Divalent, the manganese ion of+divalent are the metal ions for magnetic resonance radiography.
- 2. the preparation method of nano particle described in a kind of claim 1, it is characterised in that this method includes step in detail below：（1）Dopamine hydrochloride is dissolved in deionized water, 45-55 DEG C of water-bath 10-20min, it is 1mol/L to rapidly join concentration Sodium hydrate aqueous solution, 45-50 DEG C of open stirring 4-5h, centrifuge and produce poly-dopamine nanoparticle；Wherein, bar amine hydrochloric acid Salt, deionized water, 1mol/L sodium hydrate aqueous solution mass ratio are：150-180mg:70-100g:600-800mg；（2）Obtained poly-dopamine nanoparticle is scattered in deionized water, adjusts system pH=6-7 with watery hydrochloric acid, ultrasound adds Enter potassium permanganate, 35-55 DEG C, magnetic agitation 2-8h, centrifuge the poly-dopamine for producing manganese dioxide parcel（PDA@MnO2） Nano particle, wherein, poly-dopamine nanoparticle, deionized water, potassium permanganate mass ratio are：20-40mg:20-50g:10- 20mg。
- A kind of 3. application of the nano particle in tumour magnetic resonance imaging and photo-thermal therapy medicine is prepared described in claim 1.
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| CN108434462A (en) * | 2018-03-13 | 2018-08-24 | 中山大学 | A kind of multifunctional nano diagnosis and treatment agent and the preparation method and application thereof of mesoporous poly-dopamine load manganese carbonyl |
| CN108721645A (en) * | 2018-06-05 | 2018-11-02 | 北京化工大学 | A kind of composite nano materials of multifunctional targeted cell mitochondrial and preparation method thereof and application as antitumor drug |
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| CN109364245A (en) * | 2018-09-04 | 2019-02-22 | 中山大学 | A kind of poly-dopamine nanometer diagnosis and treatment agent and preparation method thereof |
| CN110237275A (en) * | 2019-05-23 | 2019-09-17 | 深圳大学 | A kind of nanometer of diagnosis and treatment agent and preparation method thereof, application |
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