CN109432072A - A kind of disulfiram-metal organic frame compound and its preparation method and application - Google Patents
A kind of disulfiram-metal organic frame compound and its preparation method and application Download PDFInfo
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- CN109432072A CN109432072A CN201811653591.7A CN201811653591A CN109432072A CN 109432072 A CN109432072 A CN 109432072A CN 201811653591 A CN201811653591 A CN 201811653591A CN 109432072 A CN109432072 A CN 109432072A
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- A61K31/145—Amines having sulfur, e.g. thiurams (>N—C(S)—S—C(S)—N< and >N—C(S)—S—S—C(S)—N<), Sulfinylamines (—N=SO), Sulfonylamines (—N=SO2)
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Abstract
The invention discloses a kind of disulfiram-metal organic frame compound and its preparation method and application, the disulfiram-metal organic frame compound includes the component of following parts by weight: 1~3000 part of disulfiram, 1~600 part of zinc salt and 1~6000 part of imidazolyl derivatives.The present invention is experimentally confirmed, disulfiram-the metal organic frame compound can effectively inhibit tumor cell proliferation under the conditions of low dosage, and antitumous effect is substantially better than DSF, and effective dose is low, the toxic side effect of DSF initiation is effectively reduced, the treatment cost of patient is also reduced.Meanwhile the structural stability at physiological condition (pH7.4) is good, it can accelerated release in vitro DSF at tumor microenvironment (pH5.0~pH6.5).
Description
Technical field
The present invention relates to a kind of compound more particularly to a kind of disulfiram-metal organic frame compound and its preparation sides
Method and application.
Background technique
Malignant tumour has become the major disease for threatening human health, wherein breast cancer is that the current whole world is most common
Female malignant, and the first cause of global female cancer death.In recent years, with to tumor biological behavior and molecule
The further investigation of mechanism has emerged many new treatment means such as targeted therapy, immunization therapy, so that tumor patient
Life cycle achieves biggish raising.Nevertheless, above-mentioned treatment method effect is still not ideal enough.Therefore, researcher tastes
Examination has turned one's attention to the inexpensive and with anti-tumor activity drug of the past approved, as disulfiram (disulfiram,
DSF).Disulfiram (disulfiram, DSF) also known as disulfiram are a kind of dithiocarbamates for being able to suppress alcohol acetaldehyde dehydrogenase
Formates drug can cause alcohol metabolism product acetaldehyde to accumulate in vivo, and wine-head is made to generate the detest to alcohol and be used for abstinence from alcohol
Treatment.There are also antitumor actions in addition to having abstinence from alcohol effect by researcher's discovered in recent years DSF, and DSF can kill a variety of in vivo and in vitro
Tumour cell, including the carcinoma of the rectum, melanoma, glioma, breast cancer and prostate cancer etc..Currently, the dosage form of DSF is with oral
Based on tablet, needing to take larger dose can be only achieved effective antitumour effect, but will lead to patient and be easy to appear disulfiram
The side effects such as sample reaction.Therefore, disulfiram how is improved in the therapeutic effect of anti-tumor aspect, dosage is reduced, to drop
Less toxic side effect has become a crucial problem.
Metal-organic framework material (MOFs) is developed in recent years to be led to by organic ligand and metal ion or cluster
The hybrid inorganic-organic materials with molecule inner pore for crossing coordinate bond formation, are forward position and the hot spot of materialogy research.Zeolite
Imidazate framework material (ZIF-8) is one kind of MOFs, and it is excellent to have that preparation condition is mild, porosity is high and thermal stability is good etc.
Point.
The present invention is found through experiments that, DSF and ZIF-8 can generate synergistic function, compound in anti-tumor aspect
Drug effect on antitumor will be significantly better than DSF, and dosage can be effectively reduced, to reduce DSF bring toxic side effect.
Summary of the invention
It is an object of the invention to solve above-mentioned shortcoming and defect existing in the prior art, a kind of disulfiram-gold is provided
Belong to organic frame compound (referred to as " DSF-ZIF-8 "), the antitumous effect of the DSF-ZIF-8 is significant, and dosage is low, greatly
Reduce disulfiram bring toxic side effect greatly, reduces the treatment cost of patient.
To reach its purpose, the technical scheme adopted by the invention is as follows: a kind of disulfiram-metal organic frame compound,
It includes the component of following parts by weight: 1~3000 part of disulfiram, 1~600 part of zinc salt and 1~6000 part of imidazolyl derivatives.
The present invention is found through experiments that, in the DSF-ZIF-8, ZIF-8 can be generated in anti-tumor aspect with DSF and be cooperateed with increasing
Effect effect, so that the antitumor drug effect of the DSF-ZIF-8 is significantly better than DSF, greatly reduces in tumor therapeutic procedure
Dosage, thus reduce DSF initiation toxic side effect, also reduce the treatment cost of patient.
Preferably, the disulfiram-metal organic frame compound includes the component of following parts by weight: disulfiram 100~
600 parts, 50~100 parts of zinc salt and 50~200 parts of imidazolyl derivatives.The present invention pass through experimental studies have found that, disulfiram, zinc salt
It can be affected to the disulfiram carrying drug ratio in DSF-ZIF-8 with the proportion of imidazolyl derivatives three.It is made with said ratio
DSF-ZIF-8 disulfiram carrying drug ratio it is higher, there is significant antitumous effect, and preparation cost is lower, therefore, the present invention
Using above-mentioned formula as optimization formula of the invention.
Preferably, the imidazolyl derivatives include: 2-methylimidazole, 2- imidazole formaldehyde, 4- imidazole formaldehyde, 2- sulfydryl miaow
The bromo- 1H- imidazoles of azoles, 2- nitroimidazole, 2- cyanoimidazole, 2-, 4-methylimidazole, 5- methylimidazole, 4- nitroimidazole, 5- nitro
At least one of imidazoles, 4,5- dicyano imidazole, 2- hydroxy methylimidazole, 2,4,5- tribromoimidazole.
Preferably, the zinc salt includes Zinc diacetate dihydrate, zinc acetate, zinc nitrate, at least one in zinc nitrate hexahydrate
Kind.
Preferably, the preparation method of the disulfiram-metal organic frame compound, include the following steps: by disulfiram,
N is added in zinc salt and imidazolyl derivatives, and (N, the usage amount of N '-dimethyl formamide is can make for dissolution in N '-dimethyl formamide
Each component degree of being dissolved as), 12h is stirred at room temperature, reaction product is collected by centrifugation, finally with isometric N, N '-dimethyl formyl
Amine and methanol respectively wash three times reaction product.
Preferably, the dosage form of the disulfiram-metal organic frame compound includes implant, suspension, emulsion, injection
Dosage form in agent or other pharmacies.
The present invention is found through experiments that, when the administration concentration of the DSF-ZIF-8 reaches 2.56~6.4 μm of ol/L, i.e., pair
Cancer cell multiplication has significant inhibiting effect.
The present invention also provides application of the disulfiram-metal organic frame compound in anti-tumor drug.
The present invention also provides the disulfiram-metal organic frame compound answering in the drug for the treatment of breast cancer
With.
The present invention also provides a kind of anti-tumor drugs, multiple containing disulfiram-metal organic frame of the present invention
Close object.
The present invention also provides a kind of drugs for treating breast cancer, organic containing disulfiram-metal of the present invention
Frame compound.
Compared with prior art, the beneficial effects of the present invention are:
1, the present invention is experimentally confirmed, and the DSF-ZIF-8 can effectively inhibit tumour cell under the conditions of low dosage
Proliferation, antitumous effect are substantially better than DSF.
2, the effective dose of the DSF-ZIF-8 is low, effectively reduces the toxic side effect of DSF initiation, also reduces patient
Treatment cost.
3, at physiological condition (pH7.4), the structural stability of the DSF-ZIF-8 is good, and in tumor microenvironment
Under (pH5.0~pH6.5), the DSF-ZIF-8 can accelerated release in vitro DSF.
Detailed description of the invention
Fig. 1 is the physicochemical characterization figure of the product of the embodiment of the present invention 1；(A is the X-ray powder diffraction figure of DSF-ZIF-8
Spectrum, B are the transmission electron microscope map of DSF-ZIF-8, and C is DSF-ZIF-8's1H-NMR map, the FT-IR that D is DSF-ZIF-8 scheme
Spectrum)
Fig. 2 is the result of cell proliferation experiment；
Fig. 3 is the result of cell apoptosis assay.
Specific embodiment
To better illustrate the object, technical solutions and advantages of the present invention, the present invention passes through the following example furtherly
Drug effect of the bright DSF-ZIF-8 in anti-tumor aspect.It should be understood that the embodiment of the present invention is merely to illustrate technology effect of the invention
Fruit, protection scope and is not intended to limit the present invention.In embodiment, method therefor is conventional method unless otherwise instructed.
Embodiment 1
The present embodiment 1 provides a kind of disulfiram-metal organic frame compound (DSF-ZIF-8), by following parts by weight
Group be grouped as: 350 parts of disulfiram, 75 parts of Zinc diacetate dihydrate and 125 parts of 2-methylimidazole.
The preparation method of the DSF-ZIF-8 includes the following steps: disulfiram, Zinc diacetate dihydrate and 2- methyl miaow
N is added in azoles, dissolves (N, the usage amount of N '-dimethyl formamide is can make each component degree of being dissolved as) in N '-dimethyl formamide,
12h is stirred at room temperature, reaction product is collected by centrifugation, and finally with isometric N, N '-dimethyl formamide and methanol wash respectively
Reaction product is three times.
Embodiment 2
The present embodiment 2 provides a kind of disulfiram-metal organic frame compound (DSF-ZIF-8), by following parts by weight
Group be grouped as: 200 parts of disulfiram, 60 parts of zinc acetate and 80 parts of 4-methylimidazole.Preparation method is referring to embodiment 1.
Embodiment 3
The present embodiment 3 provides a kind of disulfiram-metal organic frame compound (DSF-ZIF-8), by following parts by weight
Group be grouped as: 100 parts of disulfiram, 50 parts of zinc nitrate hexahydrate and 60 parts of 5- methylimidazole.Preparation method is referring to embodiment 1.
Embodiment 4
The present embodiment 4 provides a kind of disulfiram-metal organic frame compound (DSF-ZIF-8), by following parts by weight
Group be grouped as: 150 parts of 500 parts of disulfiram, 85 parts of Zinc diacetate dihydrate and the bromo- 1H- imidazoles of 2-.Preparation method is referring to embodiment
1。
Embodiment 5
The present embodiment 5 provides a kind of disulfiram-metal organic frame compound (DSF-ZIF-8), by following parts by weight
Group be grouped as: 600 parts of disulfiram, 100 parts of zinc acetate and 200 parts of 2- imidazole formaldehyde.Preparation method is referring to embodiment 1.
Embodiment 6
The present embodiment 6 provides a kind of disulfiram-metal organic frame compound (DSF-ZIF-8), by following parts by weight
Group be grouped as: 1000 parts of disulfiram, 200 parts of Zinc diacetate dihydrate and 1000 parts of 2- mercaptoimidazole.Preparation method is referring to implementation
Example 1.
Embodiment 7
The present embodiment 7 provides a kind of disulfiram-metal organic frame compound (DSF-ZIF-8), by following parts by weight
Group be grouped as: 2000 parts of disulfiram, 300 parts of Zinc diacetate dihydrate and 2000 parts of 2- cyanoimidazole.Preparation method is referring to implementation
Example 1.
Embodiment 8
The present embodiment 8 provides a kind of disulfiram-metal organic frame compound (DSF-ZIF-8), by following parts by weight
Group be grouped as: 3000 parts of disulfiram, 400 parts of zinc nitrate and 3000 parts of 2,4,5- tribromoimidazole.Preparation method is referring to embodiment
1。
Embodiment 9
The present embodiment 9 provides a kind of disulfiram-metal organic frame compound (DSF-ZIF-8), by following parts by weight
Group be grouped as: 3000 parts of disulfiram, 500 parts of zinc acetate and 5000 parts of 2- hydroxy methylimidazole.Preparation method is referring to embodiment 1.
Embodiment 10
The present embodiment 10 provides a kind of disulfiram-metal organic frame compound (DSF-ZIF-8), by following parts by weight
Group be grouped as: 3000 parts of disulfiram, 600 parts of zinc nitrate hexahydrate and 6000 parts of 4,5- dicyano imidazole.Preparation method reference
Embodiment 1.
Embodiment 11
The present embodiment 11 provides a kind of disulfiram-metal organic frame compound (DSF-ZIF-8), by following parts by weight
Group be grouped as: 1 part of disulfiram, 1 part of zinc nitrate and 1 part of 5- nitroimidazole.Preparation method is referring to embodiment 1.
One, the physicochemical characterization experiment of DSF-ZIF-8
Using X-ray powder diffraction, transmission electron microscope,1H-NMR and FT-IR ties the reaction product of embodiment 1
Structure characterization, shown in the result is shown in Figure 1.
In Fig. 1, A is the X-ray powder diffraction collection of DSF-ZIF-8, consistent with the crystal form of standard ZIF-8, illustrates to synthesize
Substance still has ZIF-8 crystal structure；
In Fig. 1, B is the transmission electron microscope map of DSF-ZIF-8, it can be seen that the polyhedral structure of synthetic is clear,
The size of grain is 100~150nm；
In Fig. 1, C is DSF-ZIF-8's1H-NMR map, the methyl peak that δ 2.5 is, δ 7.4 are the peak-CH=CH-, δ
12.4 be the peak-NH-, is illustrated in product with the presence of 2-methylimidazole；δ 1.2 is CH3- CH2Middle methyl peak, δ 3.9 are CH3?
CH2Methylene peak illustrates in product with the presence of disulfiram；
In Fig. 1, D is the FT-IR map of DSF-ZIF-8,1608cm-1、1739cm-1The peak at place is respectively that C=C, C=N inhale
Peak is received, is illustrated in product with the presence of 2-methylimidazole；569cm-1、1278cm-1The peak at place is respectively S-S, C-S absorption peak, explanation
With the presence of disulfiram in product.
Fig. 1's the results show that the product of embodiment 1 is the substance DSF-ZIF-8 containing disulfiram and ZIF-8.
Two, cell proliferation experiment
Cell proliferation experiment is carried out using human breast cancer cell MDA-MB-231.Respectively to be produced made from DSF and embodiment 1
Object administration, is labeled as DSF group and example 1 group, and administration concentration is respectively 0 μm of ol/L, 0.4096 μm of ol/L, 1.024 μm of ol/L,
2.56 μm of ol/L, 6.4 μm of ol/L, 16 μm of ol/L (drug concentration of example 1 group is the disulfiram concentration contained by it).With
Absorbance value after MTT colorimetric determination is administered 48 hours at 570nm wavelength, and calculate cell survival rate.As a result such as table 1 and figure
Shown in 2.
Table 1
| DSF concentration (umol/L) | 0.00 | 0.41 | 1.02 | 2.56 | 6.40 | 16.00 |
| DSF group proliferation rate (%) | 100.00 | 105.82 | 98.54 | 89.26 | 40.23 | 13.52 |
| Example 1 group appreciation rate (%) | 100.00 | 79.22 | 78.47 | 3.32 | 3.23 | 2.97 |
It can be seen that from the result of table 1 and Fig. 2, when drug concentration is 2.56 μm of ol/L and 6.4 μm of ol/L, DSF-ZIF-8 group
Cell proliferation rate be significantly lower than DSF group cell proliferation rate.Show the drug effect of DSF-ZIF-8 of the invention on antitumor
It is significantly better than DSF.
Three, cell apoptosis assay
Cell proliferation experiment is carried out using human breast cancer cell MDA-MB-231.Respectively to be produced made from DSF and embodiment 1
Object administration, labeled as control group (CTRL), DSF group, ZIF-8 group and example 1 group (DSF-ZIF-8).Administration concentration is respectively as follows:
Control group (CTRL) 0 μm of ol/L, DSF group DSF concentration is 4 μm of ol/L, and example 1 group DSF concentration is 4 μm of ol/L, ZIF-8 group
The concentration of ZIF-8 is equal to the concentration of ZIF-8 in example 1 group.After administration for 24 hours, dyed with Annexin-V-Fluo/PI kit
(being operated by kit operation instruction), is detected with flow cytometer and counts apoptosis rate.As a result as shown in Figure 3.
In Fig. 3, in the apoptosis result of each group, Q2 quadrant and Q4 quadrant are apoptotic cell.It is found through statistics, example 1 group
(DSF-ZIF-8) apoptosis ratio is apparently higher than other groups.Show that the drug effect of DSF-ZIF-8 of the invention on antitumor will be shown
It writes and is better than DSF.
Finally, it should be noted that the above embodiments are merely illustrative of the technical solutions of the present invention rather than protects to the present invention
The limitation of range is protected, although the invention is described in detail with reference to the preferred embodiments, those skilled in the art should
Understand, it can be with modification or equivalent replacement of the technical solution of the present invention are made, without departing from the essence of technical solution of the present invention
And range.
Claims (10)
1. a kind of disulfiram-metal organic frame compound, which is characterized in that the component including following parts by weight: disulfiram 1~
3000 parts, 1~600 part of zinc salt and 1~6000 part of imidazolyl derivatives.
2. disulfiram-metal organic frame compound as described in claim 1, which is characterized in that including following parts by weight
Component: 100~600 parts of disulfiram, 50~100 parts of zinc salt and 50~200 parts of imidazolyl derivatives.
3. disulfiram-metal organic frame compound as claimed in claim 1 or 2, which is characterized in that the imidazole radicals is derivative
Object includes: 2-methylimidazole, 2- imidazole formaldehyde, 4- imidazole formaldehyde, 2- mercaptoimidazole, 2- nitroimidazole, 2- cyanoimidazole, 2-
Bromo- 1H- imidazoles, 4-methylimidazole, 5- methylimidazole, 4- nitroimidazole, 5- nitroimidazole, 4,5- dicyano imidazole, 2- hydroxyl first
At least one of base imidazoles, 2,4,5- tribromoimidazole.
4. disulfiram-metal organic frame compound as claimed in claim 1 or 2, which is characterized in that the zinc salt includes two
It is hydrated at least one of zinc acetate, zinc acetate, zinc nitrate, zinc nitrate hexahydrate.
5. such as the preparation method of the described in any item disulfiram-metal organic frame compounds of Claims 1 to 4, feature exists
In including the following steps: disulfiram, zinc salt and imidazolyl derivatives N is added, dissolve in N '-dimethyl formamide, at room temperature
12h is stirred, reaction product is collected by centrifugation, finally with isometric N, N '-dimethyl formamide and methanol are respectively to reaction product
Washing is three times.
6. such as the described in any item disulfiram-metal organic frame compounds of Claims 1 to 4, which is characterized in that double sulphur
Logical sequence-metal organic frame compound dosage form includes the dosage form in implant, suspension, emulsion, injection or other pharmacies.
7. such as described in any item disulfiram-metal organic frame compound the answering in anti-tumor drug of Claims 1 to 4
With.
8. if the described in any item disulfiram-metal organic frame compounds of Claims 1 to 4 are in the drug for the treatment of breast cancer
Application.
9. a kind of anti-tumor drug, which is characterized in that organic containing such as described in any item disulfiram-metals of Claims 1 to 4
Frame compound.
10. a kind of drug for treating breast cancer, which is characterized in that containing such as the described in any item disulfirams-of Claims 1 to 4
Metal organic frame compound.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110693883A (en) * | 2019-11-21 | 2020-01-17 | 安徽医科大学第一附属医院 | Preparation method and application of rapamycin-entrapped zinc-organic framework drug delivery system |
| CN116549418A (en) * | 2023-03-31 | 2023-08-08 | 南通大学 | Nanoparticle for resisting postoperative infection and recurrence of gastric cancer as well as preparation method and application thereof |
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Application publication date: 20190308 |
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