CN104587495A - MRI (magnetic resonance imaging)-guided targeted photo-thermal agent and preparation method of chemotherapeutic system of MRI-guided targeted photo-thermal agent - Google Patents
MRI (magnetic resonance imaging)-guided targeted photo-thermal agent and preparation method of chemotherapeutic system of MRI-guided targeted photo-thermal agent Download PDFInfo
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- CN104587495A CN104587495A CN201410854285.5A CN201410854285A CN104587495A CN 104587495 A CN104587495 A CN 104587495A CN 201410854285 A CN201410854285 A CN 201410854285A CN 104587495 A CN104587495 A CN 104587495A
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Abstract
The invention relates to a MRI (magnetic resonance imaging)-guided targeted photo-thermal agent and a preparation method of a chemotherapeutic system of the MRI-guided targeted photo-thermal agent. The method comprises the following steps: by using a hydrothermal method, preparing superparamagnetic ferroferric oxide nano-particles on PEI modified MoS2 in an in-situ preparation mode, thus obtaining a PEI modified MoS2 nano composite; preparing polyethylene glycol coupled targeting molecules by using EDC chemical; by using an EDC chemical, connecting polyethylene glycol with the targeting molecules to the PEI modified MoS2 nano composite in a covalent linkage mode; and through physical adsorption, loading a micromolecular anti-tumor drug on a carrier. The method disclosed by the invention is easy to operate and simple in step, and the prepared multi-functional MoS2 nano composite is good in biological compatibility, can be specifically gathered at tumor sites so as to effectively kill tumor cells, and can effectively integrate early diagnosis and late treatment so as to realize the integration of diagnosis and treatment of cancer treatment.
Description
Technical field
The invention belongs to the preparation field of targeting photo-thermal agent, particularly the preparation method of a kind of mri guided targeting photo-thermal agent and chemotherapy system thereof.
Background technology
Photo-thermal therapy refers to the absorbent utilizing and have photo-thermal converting function, near infrared light is converted into heat energy, local temperature is raised, cause a kind for the treatment of means of malignant cell necrosis.As a kind of technology of cancer treatment emerging in recent years, the advantage that photo-thermal therapy has the traditional treatment means such as many chemotherapy, radiotherapy incomparable, as little in invasive, few side effects, treatment are quick and convenient etc.Although many inorganic optothermal materials are developed successively, the defects such as it is difficult to modify, biocompatibility and poor chemical stability strongly limit its further application at biomedical sector.MoS
2nanometer sheet has been proved has higher mass extinction coefficient than nanometer reduced graphene, has extremely tempting prospect in photo-thermal therapy field.But, by the MoS that chemical stripping legal system is standby
2although nanometer sheet can stable dispersion in aqueous phase, it is very easily sedimentation in physiological conditions.Therefore, with the Organic substance of good biocompatibility to MoS
2nanometer sheet is modified, and improves its chemical stability and biocompatibility, has substantial meaning to it in the application of field of cancer.In addition, there are some researches show, be combined by photo-thermal therapy with other therapies, building double mode therapy system effectively can improve anticancer therapeutic, and multi-mode treatment has become a main trend of field of cancer.
Summary of the invention
Technical problem to be solved by this invention is to provide the preparation method of a kind of mri guided targeting photo-thermal agent and chemotherapy system thereof, cheaper starting materials of the present invention is easy to get, easy to operate, step is simple, and reaction all completes in aqueous phase, realize friendly process prepared by material, to biomedical material and important.
The preparation method of a kind of mri guided targeting photo-thermal agent of the present invention, comprising:
(1) polymine PEI is added molybdenum bisuphide MoS
2in nanometer sheet aqueous solution, at 40-80 DEG C of back flow reaction 12-24h, obtain the MoS that PEI modifies
2nanometer sheet; Wherein the mass ratio of polymine PEI and molybdenum disulfide nano sheet is 0.2-0.8g:100-500mg;
(2) by Iron dichloride tetrahydrate FeCl
24H
2o is soluble in water, adds ammonia under stirring condition, stirs, obtains solution, then joins the MoS that PEI modifies
2in nanometer sheet aqueous solution, carry out hydro-thermal reaction, reaction temperature is 120-200 DEG C, and the response time is 5 ~ 12h, washing, obtains the MoS that PEI modifies
2nano-complex PEI-Fe
3o
4-MoS
2; The wherein MoS of Iron dichloride tetrahydrate, ammonia, PEI modification
2the ratio of nanometer sheet is 0.3-0.8g:1.5-6ml:0.1 ~ 0.5g;
(3) add in solvent by targeted molecular, 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride EDC, N-hydroxysuccinimide NHS, dissolve, stir-activating, obtains activated solution, then activated solution is added drop-wise to NH
2in-PEG-COOH solution, stirring reaction 1-3d, dialysis, lyophilization, obtains the targeted molecular of polyethylene glycol conjugation; Wherein the mol ratio of targeted molecular, EDC, NHS is 1:0.6 ~ 0.8:0.4 ~ 0.6; NH
2-PEG-COOH is about 1:0.1 ~ 0.5 with the mass ratio of targeted molecular;
(4) by the targeted molecular of above-mentioned polyethylene glycol conjugation, 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride EDC, N-hydroxysuccinimide NHS, be dissolved in deionized water, stir, then add PEI-Fe
3o
4-MoS
2aqueous solution, room temperature reaction 0.5-1d, centrifugal, dialysis, to obtain final product; The wherein targeted molecular of polyethylene glycol conjugation, EDC, NHS, PEI-Fe
3o
4-MoS
2mass ratio be about 10:(1 ~ 2): (3 ~ 5): (1 ~ 4);
In described step (1), the weight average molecular weight of polymine PEI is 15000 ~ 25000.
After adding ammonia in described step (2), stir 5-15min.
In described step (3), targeted molecular is the one in folic acid, rgd peptide, antibody.
NH in described step (3)
2the molecular weight of-PEG-COOH is 2000-4000, has both-end active function groups.
In described step (3), the stir-activating time is 1-3h.
In described step (3), solvent is dimethyl sulfoxide DMSO; NH
2the solvent of-PEG-COOH solution is dimethyl sulfoxide DMSO.
The preparation method of a kind of mri guided targeting photo-thermal-chemotherapy system of the present invention, by the mri guided targeting photo-thermal agent based on molybdenum disulfide nano sheet, pass through physical absorption, load small-molecule drug, obtain the targeting photo-thermal diagnosis and treatment agent of medicine carrying, namely based on the mri guided targeting photo-thermal-chemotherapy system of molybdenum disulfide nano sheet.
Described small-molecule drug is one or more in doxorubicin hydrochloride, hydroxy camptothecin, curcumin.
The targeting photo-thermal diagnosis and treatment agent of described medicine carrying is as the application of the double mode treatment integration of cancer diagnosis.
Molybdenum bisuphide MoS
2nanometer sheet, for be prepared by chemical stripping method, is specially: under nitrogen protection, is that the n-BuLi hexane solution of 1-2M adds containing 0.2-0.6gMoS by 5mL concentration
2in the reaction tube of powder, under room temperature, 800rpm stirs 2 days, reaction terminates rear employing filtered on buchner funnel, filtering residue is rinsed to remove excessive n-BuLi with the normal hexane of 100mL, use 300mL deionized water rinsing subsequently, a certain amount of deionized water of products therefrom is washed till in beaker, after ultrasonic disperse 1h, namely obtains MoS
2nanometer sheet.
The nanometer sheet that the present invention selects low-molecular-weight PEI standby to chemical stripping legal system is modified, and prepare SPIO wherein, bio-toxicity is reduced by PEG coupling target polypeptide, final load small molecule anticancer drug, constructs mri guided targeting photo-thermal-chemotherapy system.
For improving MoS in the present invention
2the chemical stability of nanometer sheet, utilizes hyperbranched macromolecular polyethylene imine beautify aqueous phase MoS
2nanometer sheet, can stable existence in physiological conditions; SPIO is prepared, for nuclear magnetic resonance at the special construction situ of polyethyleneimine: amine molecule; For reducing amino too much on polyethyleneimine: amine molecule to organic toxicity, to modify it with the peg molecule of amino and carboxyl difunctionality dough, and on Polyethylene Glycol coupling targeted molecular (rgd peptide), with back loading small molecule anticancer drug, construct by mri guided targeting photo-thermal-chemotherapy system.
beneficial effect
(1) cheaper starting materials of the present invention is easy to get, easy to operate, and step is simple, and reaction all completes in aqueous phase, and realize friendly process prepared by material, this is most important to bio-medical material; Obtained multi-functional MoS
2nano-complex biocompatibility is good, can at tumor locus specific accumulation, effective killing tumor cell, and effectively in earlier stage can diagnose and integrate with anaphase, realizes the diagnosis and treatment integration for the treatment of of cancer;
(2) the present invention MoS used
2nanometer sheet has very high photothermal conversion efficiency, and in physiological conditions can stable circulation after modifying, and this efficiently solves MoS
2difficulty in biologic applications process;
(3) the targeting diagnosis and treatment agent that the present invention obtains can realize double mode treatment, and have Synergistic anti-cancer effect, anticancer therapeutic is expected to significantly improve;
(4) the targeting diagnosis and treatment agent that the present invention obtains effectively can realize magnetic resonance radiography, for treatment of cancer provides diagnosis in early stage and later stage monitoring dual-use function, realizes the diagnosis and treatment integration for the treatment of of cancer.
Accompanying drawing explanation
Fig. 1 is MoS prepared by embodiment 1
2the transmission electron microscope photo of nanometer sheet;
Fig. 2 is the transmission electron microscope photo of molybdenum disulfide nano complex after the in-situ preparation ferriferrous oxide nano-particle of embodiment 1 preparation; Fig. 3 is the magnetic absorption performance photo of molybendum disulfide complexes prepared by example 1; Wherein A is for before absorption, and B is for after absorption.
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 limited range equally after the content of having read the present invention's instruction.
Embodiment 1
(1), under nitrogen protection, be that the n-BuLi hexane solution of 1.6M adds containing 0.5gMoS by 5mL concentration
2in the reaction tube of powder, under room temperature, 800rpm stirs 2 days, reaction terminates rear employing filtered on buchner funnel, filtering residue is rinsed to remove excessive n-BuLi with the normal hexane of 100mL, use 300mL deionized water rinsing subsequently, a certain amount of deionized water of products therefrom is washed till in beaker, after ultrasonic disperse 1h, namely obtains MoS
2nanometer sheet;
(2) recorded the concentration of MoS2 aqueous solution by ICP-AES after, get the aqueous solution containing 100mg MoS2 nanometer sheet, add the PEI that 0.2g molecular weight is 25000 wherein, put into 60 DEG C of oil bath pan backflow 24h after stirred at ambient temperature 1h, obtain the MoS that PEI modifies
2nanometer sheet;
(3) 0.3g FeCl is got
24H
2o is dissolved in 3.5mL water, adds 1.5mL ammonia wherein under vigorous stirring, then after stirring 10min, this solution is joined the MoS that 20mL PEI modifies
2in nanometer sheet, stir and transfer in 40mL reactor, react 12h at 130 DEG C after, collected by centrifugation product, after washing three times, is scattered in 20mL deionized water again with deionized water, obtains the magnetic MoS that PEI modifies
2nano-complex;
(4) 17.65mg rgd peptide, 6.90mg EDC and 4.14mg NHS are in a reaction bulb, add 5mL DMSO and make it dissolve completely, and stir-activating 3h.Get 40mg NH
2-PEG-COOH is dissolved in 5mL DMSO.Then the solution (5mL) of above-mentioned activation is dropwise joined NH
2in the DMSO solution (5mL) of-PEG-COOH, stirring reaction three days.To dialyse in distilled water 3d (6 times, 2L/ time) with the bag filter that molecular cut off is 1000, removing by-product and impurity, namely obtain product by after product C OOH-PEG-RGD lyophilization;
(5) get the NHS of EDC and 3.11mg of 15mg step (4) obtained PEG-RGD, 5.18mg, be dissolved in 5mL deionized water for stirring 3h, in reactant liquor, then add the PEI-Fe of 10mL
3o
4-MoS
2aqueous solution, reacts 1d under room temperature, collected after centrifugation product, and dialysis 3 days removing impurity after dispersion in deionized water, obtained PEI modifies the targeting photo-thermal therapy system with nuclear magnetic resonance function.
(6) compound concentration is the doxorubicin hydrochloride aqueous solution of 1mg/mL, get 10mL step (5) products therefrom to mix with 10mL doxorubicin hydrochloride aqueous solution, carry out centrifugal with ultra-filtration centrifuge tube after stirring 1d, cleaning is attached to the drug molecule on surface, collected product is mri guided targeting photo-thermal-chemotherapeutant, the cancer target that can be used for guided by magnetic resonance to the double mode treatment of photo-thermal-chemotherapy.
Claims (9)
1. a preparation method for mri guided targeting photo-thermal agent, comprising:
(1) polymine PEI is added molybdenum bisuphide MoS
2in nanometer sheet aqueous solution, at 40-80 DEG C of back flow reaction 12-24h, obtain the MoS that PEI modifies
2nanometer sheet; Wherein the mass ratio of polymine PEI and molybdenum disulfide nano sheet is 0.2-0.8g:100-500mg;
(2) by Iron dichloride tetrahydrate FeCl
24H
2o is soluble in water, adds ammonia under stirring condition, stirs, obtains solution, then joins the MoS that PEI modifies
2in nanometer sheet aqueous solution, carry out hydro-thermal reaction, reaction temperature is 120-200 DEG C, and the response time is 5-12h, washing, obtains the MoS that PEI modifies
2nano-complex PEI-Fe
3o
4-MoS
2; The wherein MoS of Iron dichloride tetrahydrate, ammonia, PEI modification
2the ratio of nanometer sheet is 0.3 ~ 0.8g:1.5 ~ 6ml:0.1 ~ 0.5g;
(3) add in solvent by targeted molecular, 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride EDC, N-hydroxysuccinimide NHS, dissolve, stir-activating, obtains activated solution, then activated solution is added drop-wise to NH
2in-PEG-COOH solution, stirring reaction 1-3d, dialysis, lyophilization, obtains the targeted molecular of polyethylene glycol conjugation; Wherein the mol ratio of targeted molecular, EDC, NHS is 1:0.6 ~ 0.8:0.4 ~ 0.6, NH
2-PEG-COOH is 1:0.1 ~ 0.5 with the mass ratio of targeted molecular;
(4) by the targeted molecular of above-mentioned polyethylene glycol conjugation, 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride EDC, N-hydroxysuccinimide NHS, be dissolved in deionized water, stir, then add PEI-Fe
3o
4-MoS
2aqueous solution, room temperature reaction 0.5-1d, centrifugal, dialysis, to obtain final product; The wherein targeted molecular of polyethylene glycol conjugation, EDC, NHS, PEI-Fe
3o
4-MoS
2mass ratio be about 10:(1 ~ 2): (3 ~ 5): (1 ~ 4).
2. the preparation method of a kind of mri guided targeting photo-thermal agent according to claim 1, is characterized in that: in described step (1), the weight average molecular weight of polymine PEI is 15000 ~ 25000.
3. the preparation method of a kind of mri guided targeting photo-thermal agent according to claim 1, is characterized in that: after adding ammonia in described step (2), stirs 5-15min.
4. the preparation method of a kind of mri guided targeting photo-thermal agent according to claim 1, is characterized in that: in described step (3), targeted molecular is the one in folic acid, rgd peptide, antibody.
5. the preparation method of a kind of mri guided targeting photo-thermal agent according to claim 1, is characterized in that: NH in described step (3)
2the molecular weight of-PEG-COOH is 2000-4000.
6. the preparation method of a kind of mri guided targeting photo-thermal agent according to claim 1, is characterized in that: in described step (3), the stir-activating time is 1-3h.
7. the preparation method of a kind of mri guided targeting photo-thermal agent according to claim 1, is characterized in that: in described step (3), solvent is dimethyl sulfoxide DMSO; NH
2the solvent of-PEG-COOH solution is dimethyl sulfoxide DMSO.
8. the preparation method of mri guided targeting photo-thermal-chemotherapy system, it is characterized in that: by the mri guided targeting photo-thermal agent prepared as claimed in claim 1, pass through physical absorption, load small-molecule drug, obtains the mri guided targeting photo-thermal-chemotherapy system based on molybdenum disulfide nano sheet.
9. the preparation method of a kind of mri guided targeting photo-thermal-chemotherapy system according to claim 8, is characterized in that: described small-molecule drug is one or more in doxorubicin hydrochloride, hydroxy camptothecin, curcumin.
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| CN106806898A (en) * | 2015-12-01 | 2017-06-09 | 河北工程大学 | A kind of magnetic/functionalized molybdenum bisuphide pharmaceutical carrier of folate-targeted and preparation method thereof |
| CN106806897A (en) * | 2015-12-01 | 2017-06-09 | 河北工程大学 | A kind of magnetic/functionalized tungsten disulfide pharmaceutical carrier of folate-targeted and preparation method thereof |
| CN107243082A (en) * | 2017-05-24 | 2017-10-13 | 深圳先进技术研究院 | Molybdenum disulfide indocyanine green Nano composite granules and its preparation method and application |
| CN107456577A (en) * | 2017-08-15 | 2017-12-12 | 湖北大学 | A kind of preparation method of double-mode magnetic resonance guiding photo-thermal diagnosis agent |
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| CN113101366A (en) * | 2021-04-08 | 2021-07-13 | 东南大学 | Molybdenum disulfide-based material with photo-thermal and photo-dynamic properties and preparation method thereof |
| CN113262308A (en) * | 2021-04-07 | 2021-08-17 | 桂林医学院 | Folic acid receptor mediated paclitaxel and hydroxycamptothecine superparamagnetic iron oxide nanoparticle and preparation method and application thereof |
| CN113730574A (en) * | 2020-05-29 | 2021-12-03 | 中国科学院宁波工业技术研究院慈溪生物医学工程研究所 | Composite nano material, preparation method and application |
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| CN107243082A (en) * | 2017-05-24 | 2017-10-13 | 深圳先进技术研究院 | Molybdenum disulfide indocyanine green Nano composite granules and its preparation method and application |
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| CN113730574A (en) * | 2020-05-29 | 2021-12-03 | 中国科学院宁波工业技术研究院慈溪生物医学工程研究所 | Composite nano material, preparation method and application |
| CN113730574B (en) * | 2020-05-29 | 2024-04-16 | 中国科学院宁波工业技术研究院慈溪生物医学工程研究所 | Composite nano material, preparation method and application |
| CN113262308A (en) * | 2021-04-07 | 2021-08-17 | 桂林医学院 | Folic acid receptor mediated paclitaxel and hydroxycamptothecine superparamagnetic iron oxide nanoparticle and preparation method and application thereof |
| CN113101366A (en) * | 2021-04-08 | 2021-07-13 | 东南大学 | Molybdenum disulfide-based material with photo-thermal and photo-dynamic properties and preparation method thereof |
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