CN109985247A - A kind of preparation method of the hybridized metal organic framework compounds for drug release - Google Patents
A kind of preparation method of the hybridized metal organic framework compounds for drug release Download PDFInfo
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- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
- A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
- A61K31/704—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin
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- 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
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
- A61K47/545—Heterocyclic compounds
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Abstract
The present invention provides a kind of preparation methods of hybridized metal organic framework compounds for drug release.The present invention realizes the synthesis of zeolite imidazole skeleton -8 (ZIF-8) and the loading of poly-dopamine (PDA), adriamycin (DOX) by one-step method in-situ polymerization, and metal organic framework-poly-dopamine-adriamycin hybridized metal organic framework compounds are made.PDA and DOX is encapsulated in ZIF-8 crystal, realizes the drug release and photo-thermal therapy and chemotherapy combined of pH and Near-infrared Double response, has excellent pH Drug controlled release performance, enhance the efficiency of disease treatment.
Description
Technical field
The invention belongs to porous material preparation and drug controlled release technologies fields, more particularly to one kind to be used for drug release
Hybridized metal organic framework compounds preparation method.
Background technique
Metal organic framework compound (Metal-Organic Frameworks), abbreviation MOFs also become coordination polymerization
Object is the one kind being interconnected to form by organic ligand and central metallic ions or central metal cluster by coordinate bond self assembly
Porous material with periodic structure.When the size reduction of metal organic framework compound is to nanoscale, compared to existing
Pharmaceutical carrier, nano level metal organic frame compound have lot of advantages, if the Nomenclature Composition and Structure of Complexes is adjustable, have higher ratio
Surface and specific volume, drug delivered payload capability is strong, has good biodegradable properties and excellent biocompatibility.
Photo-thermal therapy utilizes the unique photothermal conversion ability of optothermal material, and then at the energy of near infrared light conversion tumour
Amount of localized heat directly kill tumour cell.Poly-dopamine (PDA) nano particle is strong due to its good biological degradability and relatively
Near infrared absorption ability make it possible to as excellent photo-thermal therapy agent.
The metal organic framework that zeolite imidazole skeleton -8 (ZIF-8) is made of zinc ion and 2-methylimidazole quinoline ligand
Object is closed, there is excellent biocompatibility, be the Potential Vector of anticancer drug.Due to the effect of protonation, zinc ion and imidazoles
Coordination between ion can be dissociated in pH5.0-6.0.Therefore, its conduct in acid tumor microenvironment (pH5.7-7.8)
Drug storage and delivery vector have quick pH response release, while keeping stablizing under normal physiological conditions.
CN201610061310.3 discloses a kind of preparation method of light-operated drug release metal organic framework compound, this
Invention utilizes azo ligands, and acetic acid and zirconium chloride are dissolved in n,N-Dimethylformamide and obtain metal organic frame, then
It introduces drug and beta cyclodextrin is prepared.Beta cyclodextrin can combine to receive system not with trans- azo in the present invention
Without release when environmental stimuli, only after receiving ultraviolet irradiation or amantadine is added, discharge, i.e., it is prepared by the present invention
Metal organic framework compound can be realized controllable drug release.
But be first to synthesize metal organic framework compound from the point of view of the mode that its drug loads, by drug molecule
It is loaded into the duct of metal organic framework compound, then coated high molecular β ring in metal organic framework compound surface is pasted again
Smart shell, this first to prepare-rear to load-the mode preparation process coated again is complicated, and production process often will cause drug target
Waste, high production cost.
Summary of the invention
To solve technical problem present in above-mentioned background technique, the present invention provides a kind of hydridization for drug release
The preparation method of metal organic framework compound.The present invention realizes the (ZIF- of zeolite imidazole skeleton -8 by one-step method in-situ polymerization
8) metal organic framework-poly-dopamine-adriamycin is made in the loading of synthesis and poly-dopamine (PDA), adriamycin (DOX)
Hybridized metal organic framework compounds.
To achieve the goals above, the invention provides the following technical scheme:
A kind of preparation method of the hybridized metal organic framework compounds for drug release, which is characterized in that steps are as follows:
(1) adriamycin is dissolved in deionized water, solution A is made in stirring and dissolving；
(2) zinc nitrate is dissolved in deionized water, solution B is made in stirring and dissolving；
(3) Dopamine hydrochloride is dissolved in ethanol water, polyvinylpyrrolidone is added, solution C is made in stirring and dissolving；
(4) 2-methylimidazole is dissolved in deionized water, solution D is made in stirring and dissolving；
(5) under room temperature, solution A is uniformly mixed with solution C, is added slowly in solution B, stirred evenly；
(6) under room temperature, solution D is added dropwise in step (5) resulting solution with syringe, with trihydroxy methyl amino
It is 8.5, after being stirred to react 24-32 hours that aminomethane buffer, which adjusts pH value, and centrifuge separation must precipitate, as crude product；
(7) it three times, then with ethanol water is impregnated 12-16 hours, is relaundered 3 times using ethanol water washing crude product,
Centrifuge separation, by crystal at room temperature vacuum freeze drying to get hybridized metal organic framework compounds.
Preferably, the zinc nitrate, 2-methylimidazole, adriamycin, Dopamine hydrochloride molar ratio be zinc nitrate: 2- methyl
Imidazoles: adriamycin: Dopamine hydrochloride 1:0.5-1:0.5-0.8:0.5-0.7.
Preferably, the drug release that the hybridized metal of the drug release is pH, Near-infrared Double responds.
Preferably, the partial size of the hybridized metal organic framework compounds is 200-400nm.
Preferably, the step (3) is identical with concentration of alcohol in the ethanol water in step (7), the concentration of alcohol
For 40-50 mass %.
Another object of the present invention is to provide a kind of preparation of hybridized metal organic framework compounds for drug release
The hybridized metal organic framework compounds of method preparation.
The beneficial effects of the present invention are:
1, the present invention realizes the synthesis and poly-dopamine of zeolite imidazole skeleton -8 (ZIF-8) by one-step method in-situ polymerization
(PDA), metal organic framework-poly-dopamine-adriamycin hybridized metal organic backbone chemical combination is made in the loading of adriamycin (DOX)
Object.One-step method preparation process is simple, not will cause the waste of drug target, and production cost is low, is easy to industrialization.
2, hybridized metal organic framework compounds produced by the present invention, by photo-thermal therapy agent PDA and anticancer drug DOX
Heterozygosis is encapsulated in ZIF-8 crystal simultaneously, realizes drug release and photo-thermal therapy and the change of pH and Near-infrared Double response
Joint is treated, there is excellent pH Drug controlled release performance, enhance the efficiency of disease treatment.
3, in hybridized metal organic framework compounds produced by the present invention, the unique microstructure of ZIF-8, DOX and PDA,
Interaction between ZTF-8, the coordinate bond cooperation among the chemical group (such as amino and carbonyl) and complex of DOX between Zn
With existing π-π interacts between the two by DOX and PDA, keeps hybridized metal organic framework compounds obtained with higher
The load capacity of anticancer drug DOX.After tested, the partial size of hybridized metal organic framework compounds obtained 200-400nm it
Between, obtain nanoscale hybridized metal organic framework compounds.
Specific embodiment
Below with reference to embodiment, the present invention is described in further detail, to enable those skilled in the art referring to explanation
Book content can be implemented accordingly.The specific embodiment described in the following embodiments is only used as the specific embodiment of the invention
Exemplary illustration, and be not meant to limit the scope of the invention.
Embodiment 1
A kind of preparation method of the hybridized metal organic framework compounds for drug release, steps are as follows:
(1) adriamycin is dissolved in deionized water, solution A is made in stirring and dissolving；
(2) zinc nitrate is dissolved in deionized water, solution B is made in stirring and dissolving；
(3) Dopamine hydrochloride is dissolved in the ethanol water of 40 mass %, polyvinylpyrrolidone is added, stirring and dissolving is made
Solution C；
(4) 2-methylimidazole is dissolved in deionized water, solution D is made in stirring and dissolving；
(5) under room temperature, solution A is uniformly mixed with solution C, is added slowly in solution B, stirred evenly；
(6) under room temperature, solution D is added dropwise in step (5) resulting solution with syringe, with trihydroxy methyl amino
It is 8.5, after being stirred to react 24 hours that aminomethane buffer, which adjusts pH value, and centrifuge separation must precipitate, as crude product；
(7) three times using the ethanol water washing crude product of 40 mass %, it is small then with the ethanol water of 40 mass % to impregnate 12
When, relaunder 3 times, be centrifugated, by crystal at room temperature vacuum freeze drying to get hybridized metal organic backbone chemical combination
Object；
Wherein, the zinc nitrate, 2-methylimidazole, adriamycin, Dopamine hydrochloride molar ratio be zinc nitrate: 2-methylimidazole:
Adriamycin: Dopamine hydrochloride 1:0.5:0.5:0.5.
Embodiment 2
A kind of preparation method of the hybridized metal organic framework compounds for drug release, steps are as follows:
(1) adriamycin is dissolved in deionized water, solution A is made in stirring and dissolving；
(2) zinc nitrate is dissolved in deionized water, solution B is made in stirring and dissolving；
(3) Dopamine hydrochloride is dissolved in the ethanol water of 45 mass %, polyvinylpyrrolidone is added, stirring and dissolving is made
Solution C；
(4) 2-methylimidazole is dissolved in deionized water, solution D is made in stirring and dissolving；
(5) under room temperature, solution A is uniformly mixed with solution C, is added slowly in solution B, stirred evenly；
(6) under room temperature, solution D is added dropwise in step (5) resulting solution with syringe, with trihydroxy methyl amino
It is 8.5, after being stirred to react 28 hours that aminomethane buffer, which adjusts pH value, and centrifuge separation must precipitate, as crude product；
(7) three times using the ethanol water washing crude product of 45 mass %, it is small then with the ethanol water of 45 mass % to impregnate 14
When, relaunder 3 times, be centrifugated, by crystal at room temperature vacuum freeze drying to get hybridized metal organic backbone chemical combination
Object；
Wherein, the zinc nitrate, 2-methylimidazole, adriamycin, Dopamine hydrochloride molar ratio be zinc nitrate: 2-methylimidazole:
Adriamycin: Dopamine hydrochloride 1:0.7:0.6:0.6.
Embodiment 3
A kind of preparation method of the hybridized metal organic framework compounds for drug release, steps are as follows:
(1) adriamycin is dissolved in deionized water, solution A is made in stirring and dissolving；
(2) zinc nitrate is dissolved in deionized water, solution B is made in stirring and dissolving；
(3) Dopamine hydrochloride is dissolved in the ethanol water of 50 mass %, polyvinylpyrrolidone is added, stirring and dissolving is made
Solution C；
(4) 2-methylimidazole is dissolved in deionized water, solution D is made in stirring and dissolving；
(5) under room temperature, solution A is uniformly mixed with solution C, is added slowly in solution B, stirred evenly；
(6) under room temperature, solution D is added dropwise in step (5) resulting solution with syringe, with trihydroxy methyl amino
It is 8.5, after being stirred to react 32 hours that aminomethane buffer, which adjusts pH value, and centrifuge separation must precipitate, as crude product；
(7) three times using the ethanol water washing crude product of 50 mass %, it is small then with the ethanol water of 50 mass % to impregnate 16
When, relaunder 3 times, be centrifugated, by crystal at room temperature vacuum freeze drying to get hybridized metal organic backbone chemical combination
Object；
Wherein, the zinc nitrate, 2-methylimidazole, adriamycin, Dopamine hydrochloride molar ratio be zinc nitrate: 2-methylimidazole:
Adriamycin: Dopamine hydrochloride 1:1:0.8:0.7.
Comparative example 1
Preparation method is same as Example 1, is distinguished as substituting Dopamine hydrochloride with the deionized water of equivalent.
Comparative example 2
Preparation method is same as Example 1, is distinguished as substituting adriamycin with the deionized water of equivalent.
Experimental example
One, infrared response performance test
Hybridized metal organic framework compounds prepared by embodiment 1 are configured to the compound solution of series of concentrations with deionized water
(0,0.05,0.1 and 0.2mg/mL), with 808nm laser (1.6W/cm2) irradiation each solution 10 minutes, record is warm at intervals of two minutes
Degree variation.Test result such as table 1.
1 infrared response performance test of table
| Compound solution concentration/mg/mL | 0min | 2min | 4min | 6min | 8min | 10min |
| 0 | 25 | 25.7 | 26.5 | 27.4 | 28.1 | 29.5 |
| 0.05 | 25 | 28.3 | 33.2 | 38.5 | 43.4 | 46.8 |
| 0.1 | 25 | 29.4 | 35.1 | 40.8 | 48.5 | 55.6 |
| 0.2 | 25 | 31.5 | 37.7 | 45.2 | 56.7 | 68.4 |
Show the hybridized metal organic framework compounds for respectively preparing the embodiment of various concentration 1 according to the test result of table 1
Aqueous solution is placed under the irradiation of 808nm infrared light (1.6W/cm2).As the irradiation time increases, solution temperature increases, and
With the increase of compound concentration, temperature increase rate is accelerated.Under comparing, the temperature of control group deionized water is improved only
4.5℃.It is found that photothermal conversion has occurred in the hybridized metal organic framework compounds of preparation, there is preferable photothermal conversion performance.
Two, pH response release test
Hybridized metal organic framework compounds prepared by embodiment 1 are configured to the water that DOX concentration is 2mg/mL with deionized water
Solution is divided into 5 parts, and adjusting pH value respectively using phosphate buffer solution is 5.0,6.0,7.0,8.0,9.0, at 37.5 DEG C
Release experiment is carried out, after 40 hours, centrifuging and taking supernatant tests absorbance by ultraviolet-uisible spectrophotometer, calculates DOX and releases
Put percentage.Test result such as table 2:
2 pH of table response release test
| PH value | 5.0 | 6.0 | 7.0 | 8.0 | 9.0 |
| DOX discharges percentage | 85 | 78 | 40 | 24 | 15 |
Show the reduction with solution ph according to the test result of table 2, DOX discharges percentage and increases, in pH value by 7.0 drops
When to 6.0, DOX discharges percentage and increases obvious, and the hybridized metal organic framework compounds for illustrating prepared by embodiment 1 show pH
Sensitive DOX release characteristics have excellent pH Drug controlled release performance.
Three, the photo-thermal of cell-chemotherapy combined treatment test
It is divided into 7 groups using mouse mastopathy cell, according to training status, respectively with 1 × 104The concentration in every hole is inoculated into 96 orifice plates
In, 37.5 DEG C of cultivation temperature, carbon dioxide content 10%.In culture medium separately plus 9% fetal calf serum and 100units/mL
Penicillin, the streptomysin of 100g/mL, culture 24 hours after, be separately added into a series of DOX concentration gradients (0mg/mL,
0.05mg/mL, 0.1mg/mL, 0.15mg/mL, 0.2mg/mL) DOX, DOX-ZIF-8, PDA- ZIF-8, DOX- PDA-
ZIF-8 continues culture 24 hours.Mouse mastopathy cell survival rate is examined using the MTT method (MTT) of standard
It surveys.Wherein, first group is blank control group, and second group is DOX group (aqueous solution containing DOX), and third group is DOX- ZIF-8 group
(the hybridized metal organic framework compounds prepared containing comparative example 1), the 4th group (is made for infrared group of PDA- ZIF-8 containing comparative example 2
Standby hybridized metal organic framework compounds, with 808nm laser (1.6W/cm2) irradiation 5min), the 5th group is DOX- PDA-
Infrared group of ZIF-8 is (containing hybridized metal organic framework compounds prepared by embodiment 1, with 808nm laser (1.6W/cm2) irradiation
5min), it (containing hybridized metal organic framework compounds prepared by embodiment 2, is used for infrared group of DOX- PDA-ZIF-8 for the 6th group
808nm laser (1.6W/cm2) irradiation 5min), the 7th group (prepares miscellaneous for infrared group of DOX- PDA-ZIF-8 containing embodiment 3
Change metal organic framework compound, with 808nm laser (1.6W/cm2) irradiation 5min).Test result such as table 3:
The photo-thermal of 3 cell of table-chemotherapy combined treatment test
| Group | 0mg/mL | 0.05mg/mL | 0.1mg/mL | 0.15mg/mL | 0.2mg/mL |
| First group | 100% | 100% | 100% | 100% | 100% |
| Second group | 100% | 90% | 82% | 75% | 35% |
| Third group | 100% | 92% | 85% | 70% | 33% |
| 4th group | 100% | 95% | 88% | 79% | 45% |
| 5th group | 100% | 62% | 45% | 32% | 11% |
| 6th group | 100% | 65% | 51% | 36% | 15% |
| 7th group | 100% | 64% | 50% | 33% | 14% |
Show the increase with DOX concentration according to the test result of table 3, mouse mastopathy cell survival rate gradually decreases.It compares
In individual chemotherapy group (second group, third group) or individual photo-thermal therapy group (the 4th group), photo-thermal-chemotherapy combined treatment group
(the 5th group, the 6th group, the 7th group) corresponding mouse mastopathy cell survival rate reduction is more significant, reduces speed faster, explanation
The hybridized metal organic framework compounds of embodiment 1-3 preparation, which can be significantly increased, kills ability to mouse mastopathy cell, shows
Photo-thermal-chemotherapy combined treatment can cooperate with enhancing treatment of cancer effect.
Finally it should be noted that the above specific embodiment is only used to illustrate the technical scheme of the present invention rather than limits,
Although being described the invention in detail referring to preferred embodiment, those skilled in the art should understand that, it can be right
Technical solution of the present invention is modified or equivalent replacement, without departing from the spirit and scope of the technical solution of the present invention, it is equal because
Cover in scope of the presently claimed invention.
Claims (6)
1. a kind of preparation method of the hybridized metal organic framework compounds for drug release, which is characterized in that steps are as follows:
(1) adriamycin is dissolved in deionized water, solution A is made in stirring and dissolving；
(2) zinc nitrate is dissolved in deionized water, solution B is made in stirring and dissolving；
(3) Dopamine hydrochloride is dissolved in ethanol water, polyvinylpyrrolidone is added, solution C is made in stirring and dissolving；
(4) 2-methylimidazole is dissolved in deionized water, solution D is made in stirring and dissolving；
(5) under room temperature, solution A is uniformly mixed with solution C, is added slowly in solution B, stirred evenly；
(6) under room temperature, solution D is added dropwise in step (5) resulting solution with syringe, with trihydroxy methyl amino
It is 8.5, after being stirred to react 24-32 hours that aminomethane buffer, which adjusts pH value, and centrifuge separation must precipitate, as crude product；
(7) it three times, then with ethanol water is impregnated 12-16 hours, is relaundered 3 times using ethanol water washing crude product,
Centrifuge separation, by crystal at room temperature vacuum freeze drying to get hybridized metal organic framework compounds.
2. the preparation method of the hybridized metal organic framework compounds according to claim 1 for drug release, special
Sign is: the zinc nitrate, 2-methylimidazole, adriamycin, Dopamine hydrochloride molar ratio be zinc nitrate: 2-methylimidazole: Ah
Mycin: Dopamine hydrochloride 1:0.5-1:0.5-0.8:0.5-0.7.
3. the preparation method of the hybridized metal organic framework compounds according to claim 1 or 2 for drug release,
It is characterized in that, the drug release that the hybridized metal of the drug release is pH, Near-infrared Double responds.
4. the preparation method of the hybridized metal organic framework compounds according to claim 1 or 2 for drug release,
It is characterized in that, the partial size of the hybridized metal organic framework compounds is 200-400nm.
5. the preparation method of the hybridized metal organic framework compounds according to claim 1 or 2 for drug release,
It is characterized in that, the step (3) is identical with concentration of alcohol in the ethanol water in step (7), and the concentration of alcohol is 40-50
Quality %.
6. a kind of system of the hybridized metal organic framework compounds according to claim 1-5 for drug release
The hybridized metal organic framework compounds of Preparation Method preparation.
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