CN104815337A - Preparation method and antitumor activity of PEG-modified magnetic graphene oxide (GO) - Google Patents

Preparation method and antitumor activity of PEG-modified magnetic graphene oxide (GO) Download PDF

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CN104815337A
CN104815337A CN201510242930.2A CN201510242930A CN104815337A CN 104815337 A CN104815337 A CN 104815337A CN 201510242930 A CN201510242930 A CN 201510242930A CN 104815337 A CN104815337 A CN 104815337A
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peg
dox
magnetic
composite material
preparation
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陈卫红
郑秀文
甄国荣
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Linyi University
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Linyi University
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Abstract

The invention relates to a multifunctional nanoparticle capable of diagnosing and treating tumors. A magnetic graphene oxide (GO) nanomaterial with favorable biocompatibility is prepared under an EDC condensation condition through mixing a magnetic carboxylated Fe3O4 nanoparticle water solution and an aminated PEG-modified magnetic GO water solution at normal temperature and normal pressure. An anti-cancer drug adriamycin (DOX) with a water-insoluble aromatic structure is loaded on Fe3O4-PEG-GO under a pi-pi stacking action, so that a magnetic Fe3O4-PEG-GO/DOX nanoparticle integrated with tumor resistance, imaging and biocompatibility is prepared. The tumor treating effect of the anti-cancer drug is researched by combining MRI and other detecting means, the treating effect of the anti-cancer drug for the tumors is obtained, and a novel method and approach are provided for establishing a novel platform for diagnosing and treating the tumors by using a nanodrug.

Description

The preparation of the magnetic oxygenated Graphene that a kind of PEG modifies and anti-tumor activity thereof
Technical field
The present invention relates to nano material preparation and biologic applications field thereof, particularly a kind of have tumor magnetic targeted, T2 mode imaging, the material preparation method of oncotherapy and application thereof.
Background technology
Diagnostics (Theranostics), refers to that, by integrated for a Diagnosis and Treat material system, in the past few years, the research of this emerging biomedical sector obtains increasing extensive concern.Superparamagnetism Fe 3o 4nanoparticle itself, as conventional T2 magnetic resonance imaging contrast agent, also may be used for thermotherapy and pharmaceutical carrier, is one of optimum carrier building nanometer diagnosis and treatment platform.Fe 3o 4magnetic nano-particle presents higher relaxation rate with the existence of the form of three-dimensional aggregates than the magnetic nano-particle of monodispersity, thus can improve MRI imaging effect.Graphene oxide (GO) is prepared through chemical oxidation, ultrasonic stripping by graphite, and it contains a large amount of oxygen-content active groups, as carbonyl, carboxyl, hydroxyl and epoxy radicals etc.Epoxy radicals and hydroxyl base are mainly positioned on the basal plane of GO, and carbonyl and carboxyl are then distributed in the edge of GO usually.The existence of these oxy radicals makes GO have good biocompatibility and aqueous stability, and is easy to functional modification.The sp2 delocalised electron system of graphene oxide and oxy radical architectural characteristic make it can by chemical bond, π-π interacts, and the effect of the non-covalent bond such as ionic bond and hydrogen bond realizes the loading of chemotherapeutics or gene.Based on this, we are by the method for covalent coupling, by the Fe of carboxyl modified 3o 4magnetic nano-particle is connected to GO surface, defines Fe 3o 4the aggregation of nanoparticle, this magnetic composite has good biocompatibility, the more important thing is, with monodispersed Fe 3o 4nanoparticle is compared, and the former has the higher MRI T2 relaxation time, can effectively improve MRI imaging effect.The preparation of the composite of GO and magnetic nano-particle in recent years and the development of its applied research in the field such as materials chemistry, biomedicine are rapidly.Magnetic/functionalized GO composite has the target drug-carrying of magnetic mediation because of it, and MRI etc. apply and get most of the attention.With monodispersed Fe 3o 4nanoparticle is compared, and is assembled in the Fe on GO surface 3o 4nanoparticle T2 relaxation rate significantly improves, and is conducive to improving biological MRI imaging effect.GO is upper containing a large amount of oxygen-content active groups, therefore has good biocompatibility and aqueous stability.Meanwhile, GO specific surface area is huge, has the residual aroma system destroyed not yet completely in oxidizing process, makes it show superpower absorbability to water-fast aromatics drug molecule, considers Fe 3o 4the These characteristics of nanoparticle and graphene oxide, we design, have synthesized Fe 3o 4nanoparticle-graphene oxide (Fe 3o 4-GO) compound system, object utilizes the controlled loading antitumor drug of GO, and meanwhile, the magnetic targeted utilizing magnetic nano-particle to realize this multifunctional drug system transports and biological MRI imaging function.
Summary of the invention
Technical problem to be solved by this invention is to provide a kind of specificity diagnosis and treatment function nano particle and preparation method thereof realizing magnetic targeted, the diagnosis of T2 mode imaging, oncotherapy, and the method is simple to operate, reaction condition is gentle, Fe 3o 4nanoparticle-graphene oxide (Fe 3o 4-GO) compound system antitumous effect is good, and there is target tumor function, and there is the characteristic of T2 mode imaging.
The preparation of the magnetic oxygenated Graphene that a kind of PEG of the present invention modifies and anti-tumor activity thereof, DOX is coupled to composite material surface by π-π adsorption by described composite, the diagnosis and treatment function with biocompatibility of synthetic composite material collection targeting, image-forming diagnose and treatment one.
A kind of preparation method with the composite of imaging function of the present invention, comprising:
Select 75 mL Fe 3o 4the hexane solution of magnetic nano-particle, the acetone soln (1.5 mg DMSA/mL) of 75 mL DMSA and 0.188 mL triethylamine join in 250 mL there-necked flasks, 4 h are stirred under 60 DEG C of water-baths, then 50 mL ethanol are added, ultrasonic 30 min, carry out Magneto separate, removing supernatant stays precipitation, repeats Magneto separate secondary.Tetramethylammonium hydroxide with 25% adjusts pH value to be 10, and dialyse 24 h, finally with hydrochloric acid, its pH is adjusted to neutrality.
The PEG of GO modifies and is summarized as follows: get GO-COOH 1 mL (1 mg mL -1), after ultrasonic 30 min, add the PEG aqueous solution 1 mL(10 mg mL of two ends with amino -1), more ultrasonic 30 min, under stirring at room temperature, add EDC 0.5 mL(10 mg mL -1), continue stirring 2 h, again add EDC 1 mL(10 mg mL -1), continue stirring 10 h.Centrifugal 1 h of 13 000 rpm, discards precipitation, by the super filter tube ultrafiltration of supernatant with 100 kDa.By GO-PEG three the water ultrasonic disperse retained.
DMSA-Fe 3o 4nanoparticle aqueous solution (0.5 mg mL -1) adjust pH value to be 8.0 with triethylamine, add 120 mg EDC and PEG-GO aqueous solution (1.79 mg mL -1), stirred at ambient temperature 16 h, then 13 000 rpm are centrifugal, by three water washings precipitation, in triplicate, can obtain using Fe 3o 4magnetic nano-particle-GO composite (Fe 3o 4-PEG-GO).
By anticancer drugs, doxorubicin (Doxorubicin, DOX) and Fe 3o 4-PEG-GO mixes, and make GO adsorb amycin 24 h, then utilize bag filter (molecular cut off 8 000 ~ 14 000) to dialyse, dialysis solution is the PBS of pH 7, and dialyse 48 h, changes liquid once therebetween every 12 h, obtained Fe 3o 4-PEG-GO/DOX magnetic nanometer composite material.
A kind of method with the anti-tumor activity experiment of the composite of imaging function:
(1) WST cell inhibitory effect assay kit is utilized to assess nano material to the toxicity of cell.When cell grows to 50-60% in 96 orifice plates, add not commensurability Fe 3o 4-PEG-GO/DOX magnetic nanometer composite material.After hatching 24 h, WST-1 is added in sample well and control wells (non-plus nano material), after hatching 2 h, is recorded in the absorption value at 490 nm places by microplate reader in 37 DEG C of cell culture incubators.The relative survival rate of cell equals (OD450 sample/OD450 contrast) × 100%.
Fe described in described step (1) 3o 4in-PEG-GO/DOX magnetic nanometer composite material, DOX concentration is 0.25,0.5,1,2 μ g/ml.
In described step (1), the pH value of PBS buffer solution is 7.
Step (2) Fe 3o 4-PEG-GO/DOX magnetic nanometer composite material and tumor cell hatch 24 h, and supernatant PBS washes three times, and collecting cell adds nuclear magnetic tube, carry out cell MRI imaging.
Fe described in described step (2) 3o 4in-PEG-GO/DOX magnetic nanometer composite material, Fe concentration is 2.5,5,10,20,40 μ g/ml.
Beneficial effect
(1) the present invention is by multi-step synthetic method, synthesis Fe 3o 4-PEG-GO/DOX magnetic nanometer composite material, preparation method is simple to operate, experiment condition is gentle;
(2) the present invention utilizes EDC chemical condensation to react, by amidized PEG derivant covalent coupling to GO nano material, then by carboxylated Fe 3o 4with amidized GO covalent coupling, prepare Fe 3o 4-PEG-GO composite, finally loads to Fe by cancer therapy drug 3o 4-PEG-GO composite, prepares the diagnosis and treatment function nano probe of collection magnetic targeted, image-forming diagnose and chemotherapy one;
(3) in the present invention from cell hierarchical research Fe 3o 4-PEG-GO/DOX magnetic nanometer composite material diagnosis and treatment probe, to the feasibility of cancer target, imaging and treatment, selectivity and specificity, improves the recall rate of minimal disease, obtains the visual information of oncotherapy and therapeutic evaluation.
Accompanying drawing explanation
Fig. 1 is the Fe of preparation 3o 4the TEM figure of nano material.
Fig. 2 is the Fe of preparation 3o 4the TEM figure of-PEG-GO nano material.
Fig. 3 is the infared spectrum of the PEG-GO nano material of preparation.
Fig. 4 is the Fe of preparation 3o 4the ultravioletvisible absorption collection of illustrative plates of-PEG-GO/DOX nano material.
Fig. 5 is the Fe of gained 3o 4-PEG-GO/DOX nano material is to the WST cytotoxicity testing result figure of tumor cell.
Fig. 6 is the Fe of gained 3o 4-PEG-GO/DOX nano material is to the MRI testing result figure of tumor cell.
Detailed description of the invention
Below in conjunction with specific embodiment, set forth the present invention further.Should be understood that these embodiments are only not used in for illustration of the present invention to limit the scope of the invention.In addition should be understood that those skilled in the art can make various changes or modifications the present invention, and these equivalent form of values fall within the application's appended claims equally and limited after the content of having read the present invention's instruction
Scope.
Embodiment 1
(1) 75 mL 10 nm Fe are selected 3o 4(Fig. 1 is Fe to magnetic nano-particle hexane solution 3o 4the TEM of magnetic nano-particle), the acetone soln (1.5 mg DMSA/mL) of 75 mL DMSA and 0.188 mL triethylamine join in 250 mL there-necked flasks, 4 h are stirred under 60 DEG C of water-baths, then 50 mL ethanol are added, ultrasonic 30 min, carry out Magneto separate, removing supernatant stays precipitation, repeats Magneto separate secondary.Tetramethylammonium hydroxide with 25% adjusts pH value to be 10, and dialyse 24 h, finally with the hydrochloric acid of 1 M, its pH is adjusted to neutrality;
(2) GO-COOH 1 mL (1 mg mL is got -1), after ultrasonic 30 min, add the PEG aqueous solution 1 mL(10 mg mL of two ends with amino -1), more ultrasonic 30 min, under stirring at room temperature, add EDC 0.5 mL(10 mg mL -1), continue stirring 2 h, again add EDC 1 mL(10 mg mL -1), continue stirring 10 h.Centrifugal 1 h of 13 000 rpm, discards precipitation, by the super filter tube ultrafiltration of supernatant with 100 kDa.By GO-PEG three the water ultrasonic disperse retained.The GO that GO and PEG utilizing infrared spectrum characterization prepared modifies, by spectrum contrast prove PEG to GO successfully carried out modify (Fig. 3).At 2918 cm in the infrared spectrum of GO-PEG -1with 2874 cm -1all there is obviously peak in place, is attributed to the stretching vibration of methylene, because GO is originally not obvious in this place's absworption peak, so the peak of this methylene derives from PEG.In addition, in the infrared spectrum of GO-PEG, 1460 cm -1there is an obvious peak at place, and this peak belongs to the stretching vibration of amido link.
Embodiment 2
(1) DMSA-Fe 3o 4nanoparticle aqueous solution (0.5 mg mL -1) adjust pH value to be 8.0 with triethylamine, add 120 mg EDC and PEG-GO aqueous solution (1.79 mg mL -1), stirred at ambient temperature 16 h, then 13 000 rpm are centrifugal, by three water washings precipitation, in triplicate, can obtain using Fe 3o 4magnetic nano-particle-GO composite (Fe 3o 4-PEG-GO).As shown in Figure 2, the size of GO is the tens very thin laminated structures arriving hundreds of nanometers, and magnetic nano-particle is more connected on GO lamella edge, and defines aggregation;
(2) by anticancer drugs, doxorubicin (Doxorubicin, DOX) and Fe 3o 4-PEG-GO mixes, and make GO adsorb amycin 24 h, then utilize bag filter (molecular cut off 8 000 ~ 14 000) to dialyse, dialysis solution is the PBS of pH 7, and dialyse 48 h, changes liquid once therebetween every 12 h, obtained Fe 3o 4-PEG-GO/DOX magnetic nanometer composite material;
(3) by the mode of physical absorption, DOX is adsorbed onto Fe 3o 4on-PEG-GO magnetic nanometer composite material.Carry out UV Vis Spectroscopic Characterization to it, result as shown in Figure 4.DOX has obvious absworption peak, Fe at 490 nm places 3o 4also the absorption band of DOX has been there is in-PEG-GO after adsorbing DOX, but the obvious red shift of maximum absorption band, show that amycin is successfully loaded into Fe 3o 4on-PEG-GO.
Embodiment 3
(1) in 96 porocyte culture plates, cultivate HeLa cell, every porocyte density is approximately 5000, at CO 2concentration is cultivate 24 h in 37 DEG C of incubators of 5%;
(2) remove supernatant, adding containing concentration of iron in each hole is respectively 0.25 μ g mL -1, 0.5 μ g mL -1, 1 μ g mL -1, 2 μ g mL -1fe 3o 4fresh 1640 cell culture fluids (every hole repeats 3) of 100 μ L of-PEG-GO/DOX magnetic nanometer composite material, hatch 24 h;
(3) every hole adds the WST solution of 10 μ L, puts in 37 DEG C of cell culture incubators and hatches 2 h, uses microplate reader to detect the ultraviolet absorption value in each hole at 490 nm places;
(4) Fe 3o 4-PEG-GO/DOX magnetic nanometer composite material is analyzed as shown in Figure 5 the WST of cell.Fe 3o 4-PEG-GO/DOX magnetic nanometer composite material is 20 μ g mL in iron content concentration -1time, namely the concentration of amycin is 1 μ g mL -1time, to HeLa cell, there is overt toxicity, when concentration of iron reaches 40 μ g mL -1, the concentration of amycin is 2 μ g mL -1time, the relative survival rate of cell is 76%, there is significant difference, demonstrates composite and has certain kill capability to tumor cell.
Embodiment 4
(1) in 6 porocyte culture plates, cultivate HeLa cell, every porocyte density is approximately 1 × 10 6individual cell, and the culture fluid supplying every hole 2 mL, at CO 2concentration is cultivate 24 h in 37 DEG C of incubators of 5%;
(2) remove supernatant, adding containing concentration of iron in hole is respectively 2.5 μ g mL -1, 5 μ g mL -1, 10 μ g mL -1, 20 μ g mL -1, 40 μ g mL -1fe 3o 4the fresh culture of 2 mL of-PEG-GO/DOX magnetic nanometer composite material, hatches 24 h;
(3) supernatant culture fluid is removed, and with containing 1640 cell culture fluids of 10% hyclone, by the cell harvesting in 6 orifice plate, 2 holes in 1.5 mL centrifuge tubes, centrifugal collecting cell, three times are washed with PBS, collecting cell adds nuclear magnetic tube use, and 1% agarose solidifies, and carries out cell MRI imaging;
(4) MRI imaging device used is 11.7 T Bruker micro2.5 micro-MRI system, adopt multi-slice multi-echo sequence (MSME), image is the T2 weighting image of its correspondence, experiment parameter: TR=2500 ms, matrix=128 × 128, FOV=20 × 20 cm, slice thickness=1 mm;
(5) result as shown in Figure 6.Can find, after magnetic Nano material and HeLa cell incubation, when material concentration of iron is 10 μ g/mL, good cell MRI imaging can be obtained.

Claims (7)

1. one kind has tumor magnetic targeted, T2 mode imaging, chemotherapeutical Fe 3o 4-PEG-GO/DOX nano composite material, is characterized in that: in order to increase its water solublity, by EDC chemistry in the amidized PEG derivant of GO surface bond, obtains GO-PEG.
2. get GO-COOH aqueous solution, add the PEG aqueous solution of two ends with amino, more ultrasonic 30 min, under stirring at room temperature, add EDC, continue stirring 2 h, again add EDC, continue stirring 10 h.
Centrifugal 1 h of 3.13 000 rpm, discards precipitation, by the super filter tube ultrafiltration of supernatant with 100 kDa.
4. one kind has tumor magnetic targeted, T2 mode imaging, chemotherapeutical Fe as described in claim 1 3o 4the preparation method of-PEG-GO/DOX nano composite material, is characterized in that: select 10 nm Fe 3o 4the hexane solution of magnetic nano-particle adds the acetone soln containing DMSA, and stir 4 h under 60 DEG C of water-baths, then add the ethanol of 2 times of volumes, ultrasonic 30 min, carry out Magneto separate, and removing supernatant stays precipitation, repetitive operation 2 times.
5. according to the one described in claim 2, there is tumor magnetic targeted, T2 mode imaging, chemotherapeutical Fe 3o 4the preparation method of-PEG-GO/DOX nano composite material, is characterized in that: DMSA-Fe 3o 4nanoparticle aqueous solution adds EDC and GO-PEG aqueous solution, stirred at ambient temperature 16 h, and then 13 000 rpm are centrifugal, by three water washings precipitation, in triplicate.
6. according to the one described in claim 3, there is tumor magnetic targeted, T2 mode imaging, chemotherapeutical Fe 3o 4the preparation method of-PEG-GO/DOX nano composite material, is characterized in that: by anticancer drugs, doxorubicin DOX and Fe 3o 4-PEG-GO mixes, and makes GO adsorb amycin 24 h, the DOX that then dialysis removing is excessive.
7. a kind of Fe with tumor magnetic targeted, T2 mode imaging, oncotherapy according to claim 4 3o 4-PEG-GO/DOX nano composite material is as the application in antineoplastic drug carrier.
CN201510242930.2A 2015-05-14 2015-05-14 Preparation method and antitumor activity of PEG-modified magnetic graphene oxide (GO) Pending CN104815337A (en)

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Cited By (5)

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CN106908502A (en) * 2017-03-27 2017-06-30 电子科技大学 The preparation method of the glucose sensor enzyme electrode of carbon-coated magnetic ferrite modification
CN107050453A (en) * 2017-06-13 2017-08-18 广西医科大学 Magnetic Nano targeted oxidative graphene pharmaceutical carrier and its preparation method and application
CN108295255A (en) * 2018-01-31 2018-07-20 武汉大学 A kind of drug loaded magnetic graphene multifunctional composite and preparation method thereof
CN109603750A (en) * 2018-12-27 2019-04-12 曲阜师范大学 One kind includes Fe3O4The preparation method of the plural gel adsorbed film of-GQDs
CN113577294A (en) * 2021-07-28 2021-11-02 苏州市美霖达生物科技有限公司 Preparation method of neodymium iron boron magnetic material/graphene composite drug-loaded carrier material

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106908502A (en) * 2017-03-27 2017-06-30 电子科技大学 The preparation method of the glucose sensor enzyme electrode of carbon-coated magnetic ferrite modification
CN106908502B (en) * 2017-03-27 2019-03-01 电子科技大学 The preparation method of the glucose sensor enzyme electrode of carbon-coated magnetic ferrite modification
CN107050453A (en) * 2017-06-13 2017-08-18 广西医科大学 Magnetic Nano targeted oxidative graphene pharmaceutical carrier and its preparation method and application
CN108295255A (en) * 2018-01-31 2018-07-20 武汉大学 A kind of drug loaded magnetic graphene multifunctional composite and preparation method thereof
CN109603750A (en) * 2018-12-27 2019-04-12 曲阜师范大学 One kind includes Fe3O4The preparation method of the plural gel adsorbed film of-GQDs
CN109603750B (en) * 2018-12-27 2021-11-16 曲阜师范大学 Containing Fe3O4Preparation method of-GQDs composite gel adsorption film
CN113577294A (en) * 2021-07-28 2021-11-02 苏州市美霖达生物科技有限公司 Preparation method of neodymium iron boron magnetic material/graphene composite drug-loaded carrier material

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Application publication date: 20150805