CN105126125A - Zinc oxide-gadolinium-drug composite nanoparticle, and preparation method and application thereof - Google Patents
Zinc oxide-gadolinium-drug composite nanoparticle, and preparation method and application thereof Download PDFInfo
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- CN105126125A CN105126125A CN201510576839.4A CN201510576839A CN105126125A CN 105126125 A CN105126125 A CN 105126125A CN 201510576839 A CN201510576839 A CN 201510576839A CN 105126125 A CN105126125 A CN 105126125A
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Abstract
The invention belongs to the technical field of nanometer materials, and particularly relates to a zinc oxide-gadolinium-drug composite nanoparticle, and a preparation method and application thereof. The composite nanoparticle comprises a zinc oxide nanocrystal core, a polymer shell, gadolinium (III) ions modified by coordinate bonds and surface-loaded anti-cancer drug molecules, has high stability, luminescence property and magnetic relaxation rate and can be applied to cell and small animal fluorescence imaging, magnetic resonance imaging, mouse tumor treatment and the like. The preparation method includes coating a zinc oxide nanoparticle with a polymer through two copolymerization reactions, coordinating a large quantity of carboxyl groups carried by the polymer with the gadolinium (III) ions to magnetize the nanoparticle, and loading the drug molecules onto the surface of the nanoparticle. A nanoparticle drug loading platform has a good fluorescence-magnetic resonance imaging function, high drug loading rate and high release rate, is low in toxicity and is completely degraded in mouse bodies without residues, thereby having better biosecurity and medication specificity than anti-cancer drugs.
Description
Technical field
The invention belongs to technical field of nano material, be specifically related to a kind of zinc oxide-gadolinium-medicine composite nanoparticle and its preparation method and application integrating fluorescence imaging, nuclear magnetic resonance, cancer therapy drug load and release several functions.
Background technology
Cancer has become 21 century frequently-occurring disease and commonly encountered diseases, seriously threatens the healthy of the mankind and life.Although the embolic chemotherapy of conventional cancer can suppress the deterioration of cancer to a certain extent, inevitably injure normal cell and health tissues over the course for the treatment of, finally can destroy the immune system of patient.Nanotechnology and biomedical combination create nano-medicament carrier, this kind of new material can high-efficient carrier cancer therapy drug, the microenvironment of peritumoral tissues or the microenvironment of cancerous cell inside is utilized to carry out targeting ground release anti-cancer medicine, to avoid the injury to health tissues cell.Meanwhile, over the course for the treatment of by labelling technique as nuclear magnetic resonance, fluorescence imaging carry out real-time monitoring and can improve therapeutic effect.Therefore, multifunctional nano carrying platform obtains extensive and deep research recent years, this kind of platform can being insoluble in water, medicine that bio-toxicity is large renders to inside tumor cells exactly, demonstrates remarkable performance.But, conventional nano platform is as excessive in the material volume such as polymer microsphere and mesoporous silicon oxide is difficult to degraded excretion, nanoparticle containing heavy metal component also exists the poisoning risk of accumulation property as rare earth compound, and the nano drug-carrying platform developing biological safety high has substantial worth to practical application.
Zinc oxide is as a kind of material of safety non-toxic, be the safe material (FDA code 21CFR182.8991) of food and drug administration (FoodandDrugAdministration) certification, be widely used in the commodity such as sunscreen cream, skin anti-inflammatory ointment, baby diapers, deodorant underwear.Zinc oxide quantum dot as a kind of cheap and nano material of diverse in function, by chemosynthesis can its fluorescence property of modulation, strengthen its stability in living things system and safety.In past 10 years, large quantifier elimination proves that zinc oxide nano-particle has higher safety to biological cell and toy.In addition, Zinc oxide quantum dot has the feature of pH response, can decompose release anti-cancer medicine completely in inside tumor weakly acidic condition.Therefore, zinc oxide nano-particle is utilized not only to have as the medicine carrying shipping platform of cancer therapy drug natural in tumor tissues targeting selectivity, and not residual any harmful material, the fluorescence of Zinc oxide quantum dot self contributes to the monitoring to medicament transport dispose procedure.But, the fluorescence of Zinc oxide quantum dot is positioned at green-yellow light district, cannot penetrate living animal, introduces magnetic contrast medium, then can monitor the process of toy oncotherapy to zinc-oxide nano platform.
Summary of the invention
The object of this invention is to provide a kind of " zinc oxide-gadolinium-medicine " composite nanoparticle and its preparation method and application integrating fluorescence imaging, nuclear magnetic resonance, cancer therapy drug load and release several functions.
" zinc oxide-gadolinium-medicine " provided by the invention composite nanoparticle, is made up of anti-tumor drug molecule four part of zinc oxide nanocrystalline kernel, polymer shell, gadolinium (III) ion modified by coordinate bond, area load.Specifically prepared by following steps:
(1) organic zinc salt is hydrolyzed in organic solvent, generates the zinc oxide nano-particle of luminescence generated by light; Organic zinc salt is hydrolyzed in organic solvent, generates the zinc oxide nano-particle of luminescence generated by light; The zinc oxide nano-particle making this copolymer coated can stabilized illumination in aqueous solution, buffer solution, cell culture fluid and animal blood;
(2) Gadolinium trichloride is added in the zinc oxide nano-particle aqueous solution obtained to step (2), utilize carboxyls a large amount of on copolymer side chain and gadolinium (III) ion coordination, form stable " zinc oxide-gadolinium " composite nanoparticle, should " composite nanoparticle possesses excellent relaxation rate due to the magnetic of gadolinium and special Coordination Space structure;
(3) " zinc oxide-gadolinium " composite nanoparticle aqueous solution step (3) obtained, mix with cancer therapy drug (if amycin (DOX), gram azoles are for Buddhist nun, Ni Danibu, AZD9291 etc.), utilize the interaction between drug molecule and nanoparticle, comprise the modes such as hydrogen bond, coordination, Electrostatic Absorption, hydrophobic interaction, drug molecule is loaded to nanoparticle surface; The medicine of non-load in removing aqueous solution of repeatedly dialysing again, solution is concentrated, lyophilizing, obtains " zinc oxide-gadolinium-medicine " composite nanoparticle, for Powdered.
In step (1), organic zinc salt is hydrolyzed in organic solvent, the specific operation process (building-up process of Zinc oxide quantum dot) generating the zinc oxide nano-particle of luminescence generated by light is: the methacrylic acid zinc powder of 0.4-0.5 gram is placed in there-necked flask, add dehydrated alcohol as solvent, be heated to it and dissolve completely (lower than 90 degrees Celsius); Be cooled to after room temperature until it, add the azo isobutyronitrile (AIBN) of 0.05-0.07 gram and the PEGMEMA of 3.5-4 milliliter, under the effect of magnetic agitation, heating keeps backflow; After 5-15 minute, add the lithium hydroxide solution (0.14 mole often liter) of 20-30 milliliter and the azo isobutyronitrile (AIBN) of 0.05-0.07 gram; 0.5-1.5 hour is stirred in reflux state lower magnetic force; Be cooled to after room temperature until it, put into bag filter, dialyse more than 1 day in deionized water, obtain ZnO quantum dot.
In step (2), utilize carboxyls a large amount of on copolymer side chain and gadolinium (III) ion coordination, the specific operation process forming stable " zinc oxide-gadolinium " composite nanoparticle is: the aqueous solution (10 mM/ls) adding the Gd3+ of 2-3 milliliter in the aqueous solution of the Zinc oxide quantum dots of 10 milliliters (0.941 mg/litre), at room temperature stir and spend the night, in sodium citrate aqueous solution, dialysis is used for removing unreacted Gd3+ afterwards, dialyse more than 1 day in deionized water solution again, obtain ZnO-Gd nanoparticle.
" zinc oxide-gadolinium-medicine " composite nanoparticle that the present invention obtains, its diameter can regulate in 2 ~ 20 nanometer range, and luminous wavelength can modulation in 450 ~ 650 nanometer range, and quantum yield is more than 30%.On each particle, the par of gadolinium (III) ion is adjustable within the scope of 20 ~ 200, and its longitudinal relaxation rate changes in 20 ~ 80 every mM of scopes per second.Load capacity (by mass percentage) 0 ~ 20%(of cancer therapy drug preferably 1 ~ 20%) modulation in scope.
" zinc oxide-gadolinium-medicine " composite nanoparticle that the present invention obtains, as the fluorescence imaging in organism and nuclear magnetic resonance material, for the fluorescence imaging in organism and nuclear magnetic resonance.
" zinc oxide-gadolinium-medicine " composite nanoparticle that the present invention obtains, can be used as the pharmaceutical carrier of oncotherapy, is used for the treatment of tumor aspect.
" zinc oxide-gadolinium-medicine " composite nanoparticle that the present invention obtains, is dissolved in the buffer solution of different pH value, the feature release medicine utilizing zinc oxide nano-particle to decompose under mildly acidic conditions.When pH is in 7.0 ~ 8.0 scopes, this nanoparticle is highly stable; When pH is in 6.0 ~ 7.0 scopes, zinc oxide nano-particle slowly decomposes; When pH is in 5.0 ~ 6.0 scopes, zinc oxide nano-particle just can decompose the whole medicine of release completely in 24 hours, was a kind of pharmaceutical carrier of efficient pH response.In cancerous cell and animal tumor, pH is generally in 5.0 ~ 6.0 scopes, and therefore this " zinc oxide-gadolinium-medicine " composite nanoparticle possesses the function that selectivity kills tumor cell.
" zinc oxide-gadolinium-medicine " composite nanoparticle that the present invention proposes, can carry out fluorescence imaging analysis to various zooblast and mouse tumor.Due to the relaxation rate (higher more than 10 times than commercial " gadolinium-diethyl pentetic acid ") that it is outstanding, the mr imaging technique of longitudinal relaxation time (T1) weight can be utilized to carry out In vivo detection to mouse tumor.
" zinc oxide-gadolinium-medicine " composite nanoparticle that the present invention obtains, proves the experiment of the in vitro toxicity of multiple cancerous cell, and it kills the speed of cancerous cell and the efficiency cancer therapy drug apparently higher than same concentrations itself; Show the tracking results of mouse tumor injection experiment, the successful that its Tumor suppression grows is higher than the cancer therapy drug of same concentrations itself.
Accompanying drawing explanation
Fig. 1 is the high resolution transmission electron microscopy photo of the product of embodiment 1.As can be seen from Fig. 1, the diameter of nanoparticle is 3 nanometers.
The inverse of T2 that Fig. 2 is zinc oxide-gadolinium-amycin, zinc oxide-gadolinium, gadolinium (III) ion and gadolinium-diethyl pentetic acid aqueous solution record under 0.55 Tesla magnetic fields and the associated straight lines of gadolinium (III) ion concentration, the slope of fitting a straight line is then transverse relaxation rate.Can know from figure its transverse relaxation rate value of end product obtained in embodiment 1 be 64.63 every mM per second, be far longer than the relaxation rate of business gadolinium-diethyl pentetic acid, also namely show that this nanoparticle is extraordinary longitudinal relaxation time (T1) contrast agent.
Fig. 3 is the fluorescence imaging of product in mouse tumor inside and the photo of NMR (Nuclear Magnetic Resonance) imaging of embodiment 1.Can see clearly in the drawings, under the laser excitation of 530 nanometers, nanoparticle launches very strong fluorescence signal.And also can observe the enhancing of obvious magnetic resonance imaging signal at tumor locus, its signal is 4 times of the mouse tumor injecting normal saline.Product of the present invention can have potential application in conjunction with two kinds of different imaging modes in auxiliary treatment imaging.
Fig. 4 be product in embodiment 1 by intratumor injection in the tumor of mice, carry out the oncotherapy of mice.Can find out clearly from figure, but its tumor of mice growth of injecting the product in embodiment 1 is suppressed significantly, even its inhibition is more obvious.
Fig. 5 is preparation flow of the present invention diagram.
Detailed description of the invention
The invention is further illustrated by the following examples.
embodiment 1
(1) synthesis of zinc oxide (ZnO) quantum dot
The methacrylic acid zinc powder taking 0.47 gram is placed in there-necked flask, adds the dehydrated alcohol of 25 milliliters, is heated to 72 DEG C and dissolves completely to it.Be cooled to after room temperature until it, add the azo isobutyronitrile (AIBN) of 0.06 gram and the polyethylene glycol monomethyl ethermethacrylic acid esters (PEGMEMA) of 3.75 milliliters, under the effect of magnetic agitation, be heated to 72 DEG C; After 10min, add the lithium hydroxide solution (0.14 mol/L) of 25 milliliters and the azo isobutyronitrile (AIBN) of 0.06 gram.1 hour is stirred in 72 DEG C of lower magnetic forces.Be cooled to after room temperature until it, put into bag filter, dialyse 3 days in deionized water, obtain polymer-modified ZnO quantum dot.
(2) synthesis of zinc oxide-gadolinium nanoparticle
The Gadolinium trichloride aqueous solution (10 mM/ls) of 2.35 milliliters is added in the aqueous solution of the Zinc oxide quantum dot (0.941 mg/ml) of the polymethylacrylic acid monomethyl ethers modifications of 10 milliliters, at room temperature stir and spend the night, in sodium citrate aqueous solution, dialysis is used for removing unreacted gadolinium (III) ion for 4 hours afterwards, then dialysis obtains zinc oxide-gadolinium nanoparticle for 2 days in deionized water solution.
(3) synthesis of zinc oxide-gadolinium-adriamycin nano particle
In the aqueous solution of the zinc oxide of 20 milliliters-gadolinium nanoparticle, add the amycin aqueous solution of 2 milliliters, at room temperature stir and spend the night, color becomes purple from Chinese red, and dialysing with deionized water afterwards removes unreacted amycin in two days.
embodiment 2
Preparation method is identical with embodiment 1, but the Gadolinium trichloride (10 mM/ls) used in step (2) is 2.35 milliliters, and mixing time changes 15 days into, and other conditions are constant.Under these conditions, gadolinium (III) ion can carry out sufficient coordination with the carboxyl of zinc oxide surface, its longitudinal relaxation rate relaxation rate be 55.3 every mM per second.
embodiment 3
Preparation method is identical with embodiment 1, but the Gadolinium trichloride (10 mM/ls) used in step (2) is 1 milliliter, and other conditions are constant.Under these conditions, the Gd ion of zinc oxide surface is less, its longitudinal relaxation rate relaxation rate be 47.2 every mM per second.
embodiment 4
Preparation method is identical with embodiment 1, but the Gadolinium trichloride (10 mM/ls) used in step (2) is 2.7 milliliters, and other conditions are constant.Under these conditions, the Gd ion of zinc oxide surface is more, its longitudinal relaxation rate relaxation rate be 57.89 every mM per second.
embodiment 5
Preparation method is identical with embodiment 1, but the Gadolinium trichloride (10 mM/ls) used in step (2) is 0.17 milliliter, and other conditions are constant.Under these conditions, the Gd ion of zinc oxide surface is less, its longitudinal relaxation rate relaxation rate be 33.6 every mM per second.
embodiment 6
Take zinc methacrylate 0.235 gram, be dissolved in 20 milliliters of triethylene-glycols (TEG), be heated to 72oC under magnetic stirring and dissolve completely to it.Add triethylene-glycol (TEG) solution of the azo isobutyronitrile of 0.05 gram and the 2-amidoethyl methacrylate hydrochlorate of 20 milliliter of 0.05 mol/L after being cooled to room temperature, be heated to 65 DEG C and react 10 minutes at 65 DEG C.Triethylene-glycol (TEG) solution adding the azo isobutyronitrile of 0.05 gram and the LiOH of 20 milliliter of 0.1 mol/L afterwards again reacts 1 hour under 72oC.The solution obtained is transferred in bag filter after being cooled to room temperature, dialyses three days, namely obtains the zinc oxide nano-particle of surface containing carboxyl.Remaining condition is constant, the zinc-oxide nano pharmaceutical carrier finally obtained, its longitudinal relaxation rate relaxation rate be 51.4 every mM per second.
embodiment 7
Preparation method is identical with embodiment 6, and 2-amidoethyl methacrylate hydrochlorate is changed to Methacrylamide, and obtain the Zinc oxide quantum dot that same surface has carboxyl, other condition is constant.The zinc-oxide nano carrier of the nucleocapsid structure finally obtained.Its longitudinal relaxation rate relaxation rate be 43.7 every mM per second.
embodiment 8
Preparation method is identical with embodiment 1, but in step (3), amycin is replaced to gram azoles for Buddhist nun, the zinc-oxide nano carrier that finally obtains.Its longitudinal relaxation rate relaxation rate be 54.7 every mM per second.
embodiment 9
Preparation method is identical with embodiment 1, but in step (3), amycin is replaced to Ni Danibu, the zinc-oxide nano carrier finally obtained.Its longitudinal relaxation rate relaxation rate be 51.32 every mM per second.
embodiment 10
Preparation method is identical with embodiment 1, but in step (3), amycin is replaced to AZD9291, the zinc-oxide nano carrier finally obtained.Its longitudinal relaxation rate relaxation rate be 50.47 every mM per second.
Claims (8)
1. zinc oxide-gadolinium-medicine composite nanoparticle, is characterized in that, is made up of anti-tumor drug molecule four part of zinc oxide nanocrystalline kernel, polymer shell, gadolinium (III) ion modified by coordinate bond, area load.
2. zinc oxide-gadolinium-medicine composite nanoparticle according to claim 1, is characterized in that, diameter is in 2 ~ 20 nanometer range, and luminous wavelength is in 450 ~ 650 nanometer range, and quantum yield is more than 30%; On each particle, the par of gadolinium (III) ion is within the scope of 20 ~ 200, and its longitudinal relaxation rate changes in 20 ~ 80 every mM of scopes per second; The load capacity of cancer therapy drug is 1 ~ 20% by mass percentage.
3. zinc oxide-gadolinium-medicine composite nanoparticle according to claim 1, is characterized in that, described cancer therapy drug is that amycin, gram azoles are for Buddhist nun, Ni Danibu or AZD9291.
4. a preparation method for the zinc oxide-gadolinium-medicine composite nanoparticle as described in one of claim 1-3, is characterized in that concrete steps are:
(1) organic zinc salt is hydrolyzed in organic solvent, generates the zinc oxide nano-particle of luminescence generated by light; And the polymerization reaction on the solid surface caused by free radical forms " hydrophobe-hydrophile " copolymer shell at zinc oxide nano-particle, the zinc oxide nano-particle making this copolymer coated can stabilized illumination in aqueous solution, buffer solution, cell culture fluid and animal blood;
(2) add Gadolinium trichloride in the zinc oxide nano-particle aqueous solution obtained to step (2), utilize carboxyls a large amount of on copolymer side chain and gadolinium (III) ion coordination, form stable " zinc oxide-gadolinium " composite nanoparticle;
(3) " zinc oxide-gadolinium " composite nanoparticle aqueous solution step (3) obtained, mixes with cancer therapy drug, utilizes the interaction between drug molecule and composite nanoparticle, drug molecule is loaded to nanoparticle surface; Again through repeatedly dialysing, the medicine of non-load in removing aqueous solution, solution is concentrated, lyophilizing, obtains " zinc oxide-gadolinium-medicine " composite nanoparticle, for Powdered.
5. the preparation method of zinc oxide-gadolinium-medicine composite nanoparticle according to claim 4, is characterized in that:
In step (1), organic zinc salt is hydrolyzed in organic solvent, generation has " hydrophobe-hydrophile " copolymer shell and the specific operation process of the zinc oxide nano-particle of luminescence generated by light are: the methacrylic acid zinc powder of 0.4-0.5 gram is placed in there-necked flask, add dehydrated alcohol as solvent, be heated to it and dissolve completely; Be cooled to after room temperature until it, add the azo isobutyronitrile of 0.05-0.07 gram and the PEGMEMA of 3.5-4 milliliter, under the effect of magnetic agitation, heating keeps backflow; After 5-15 minute, add the lithium hydroxide solution of 20-30 milliliter 0.14 mole often liter and the azo isobutyronitrile of 0.05-0.07 gram; 0.5-1.5 hour is stirred in reflux state lower magnetic force; Be cooled to after room temperature until it, put into bag filter, dialyse more than 1 day in deionized water, obtain ZnO quantum dot.
6. the preparation method of zinc oxide-gadolinium-medicine composite nanoparticle according to claim 4, it is characterized in that: in step (2), utilize carboxyls a large amount of on copolymer side chain and gadolinium (III) ion coordination, the specific operation process forming stable " zinc oxide-gadolinium " composite nanoparticle is: the Gd adding 2-3 milliliter 10 mM/ls in the aqueous solution of the Zinc oxide quantum dot of 10 milliliter of 0.941 mg/litre
3+aqueous solution, at room temperature stir spend the night, afterwards in sodium citrate aqueous solution dialysis be used for removing unreacted Gd
3+, then dialyse more than 1 day in deionized water solution, obtain ZnO-Gd nanoparticle.
7. zinc oxide-gadolinium-medicine as claimed in claim 1 " composite nanoparticle, as the application of fluorescence imaging in vivo and nuclear magnetic resonance material.
8. zinc oxide-gadolinium-medicine as claimed in claim 1 " composite nanoparticle, as the application of anti-tumor medicine carrying agent.
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