CN1907494A - Polybutylcyanoacrylate nano-granule with resolubity, its application and use thereof - Google Patents
Polybutylcyanoacrylate nano-granule with resolubity, its application and use thereof Download PDFInfo
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Abstract
The invention relates to a double soluble polycyanoimide acrylate nanometer particle, which is formed by polycyanoimide acrylate, DEAE-Dextran, Dextran-70, amylaceum and mannite, while the mass percentages of said components are polycyanoimide acrylate at 2.0-16.3%, DEAE-Dextran at 1.9-8.8%, Dextran-70 at 3.3-19.0%, amylaceum at 30.3-79.6% and mannite at 8.3-52.8%. And the invention also provides a relative preparation, which uses polycyanoimide acrylate as raw material, and uses the polymerization emulsion method to prepare the polycyanoimide acrylate nanometer particle, with added protective agent, to cool and dry to obtain the product. The invention can be double dissolved completely, as the carrier of nucleinic acid, to avoid degrade DNA enzyme, improve the cell extract rate, and target cancer cell.
Description
Affiliated technical field
This method belongs to the homopolymer with one or more unsaturated aliphatic based compounds or the technical field of compositions of copolymer, is specifically related to a kind of polybutylcyanoacrylate nanoparticle and technology of preparing thereof.
Background technology
Gene therapy is the focus of present pharmacy and medical domain research, and exonuclease treatment is one of key areas wherein, but nucleic acid enter in the body after easily by DNA enzymatic degradation in the body, and the cell uptake rate is low, is difficult to reach ideal therapeutic effect.The polybutylcyanoacrylate nanoparticle is the ideal carrier of nucleic acid, has the DNA of preventing enzymatic degradation, improves the cell uptake rate, suppresses characteristics such as tumor cell.The paper " preparation of poly-alkyl-alfa-cyanoacrylate nanoparticles genophore and the in vitro study of relevant nature " that the Zhang Yangde that " contemporary Chinese medical journal " 2004 the 14th the 1st phase of volume publishes etc. writes and Andreas.Zimmer writes and at " Methods " 1999; 18; a kind of method that adopts emulsion polymerization method to prepare the polybutylcyanoacrylate nanoparticle is disclosed among " the Antisense Oligonucleotide Deliverywith Polyhexylcyanoacrylate Nanoparticles as Carriers. " that delivers on the 286-295; this method is: in the hydrochloric acid solution of 50ml (pH 2.0); add 0.2g DEAE-Dextran (diethylamino ethyl-glucosan) and 0.3gDextran-60 (glucosan-60); slowly add the own ester monomer of alpha-cyanoacrylate then, 20 ℃ are stirred 24h down.But the product that adopts this method to make, its solution is not suitable for long preservation, and room temperature is placed coagulation is easily taken place, and goes mouldy, and generally adopts low-temp storage, uses and preserve equal inconvenience; The dried product that adopts lyophilization and heating means to obtain, can not water during use etc. medium redissolve, phenomenons such as adhesion often appear, lost the character of original nano_scale particle, it can't be used as nucleic acid carrier.Therefore, seek a kind of new method and prepare polybutylcyanoacrylate nanoparticle dry product, it not only can at room temperature be preserved for a long time, and after medium such as water redissolves, can keep the preceding character of polybutylcyanoacrylate nanoparticle drying, be suitable for being used for gene therapy, just become the object of those skilled in the art's researchs as nucleic acid carrier.
Summary of the invention
The object of the present invention is to provide a kind of preparation method of the polybutylcyanoacrylate nanoparticle freeze-dried products that redissolves, freeze-dried products can either long-term storage, again can be at water, can redissolve fully in normal saline or other waters, adhesion phenomenon can be do not occurred, the cell uptake rate can be improved in use.Provide this product to be used for the purposes of gene therapy as nucleic acid carrier simultaneously.
Technical solution of the present invention is as follows.
A kind of solubility polybutylcyanoacrylate nanoparticle, it is characterized in that, mainly be made up of polybutylcyanoacrylate, DEAE-Dextran, Dextran-70, glucose and mannitol, the mass percent of each component is polybutylcyanoacrylate 2.0～16.3%, DEAE-Dextran 1.9～8.8%, Dextran-70 3.3～19.0%, glucose 30.3～79.6%, mannitol 8.3～52.8%.Wherein, polybutylcyanoacrylate is a kind of in paracyanogen base acrylic acid methyl ester., paracyanogen base ethyl acrylate, paracyanogen base butyl acrylate or the Poly(hexyl-2-cyanoacrylate).
The method for preparing above-mentioned solubility polybutylcyanoacrylate nanoparticle may further comprise the steps:
With DEAE-Dextran, Dextran-70, cyanoacrylate monomer is a raw material, with glucose and mannitol is protective agent, according to 0.9～1.5: 1.5～3.5 mass ratio takes by weighing totally 2～4.5 parts of DEAE-Dextran and Dextran-70, it is dissolved in 80～250 parts of pH is in 1.5～2.5 the hydrochloric acid solution, under stirring condition, to 1～3 part of above-mentioned mixed solution and dripping cyanoacrylate monomer, after dropwising, continue to stir 3～8h, add 10～25 parts of glucoses then, 3～15 parts in mannitol, stir 10～30min, get polybutylcyanoacrylate nanoparticle suspension, wherein, cyanoacrylate monomer is the methyl 2-cyanoacrylate monomer, the cyanacrylate monomer, a kind of in the own ester monomer of Tisuacryl monomer and alpha-cyanoacrylate;
Above-mentioned suspension is put into freezing chamber pre-freeze 1～5h of-30～-50 ℃, and pre-freeze is finished, and takes out the pre-freeze sample, put into freezer dryer fast and carry out lyophilization, remove moisture, promptly make solubility polybutylcyanoacrylate nanoparticle freeze-dried products, its particle diameter is 120～180nm.
In use, it is a certain amount of to get the above-mentioned Poly(methyl cyanoacrylate) nano-granule freeze-dried powder that makes, and adds ultra-pure water and redissolves in right amount, becomes the nanoparticle suspension, and nanoparticle concentration is 180～230mg/L; It is a certain amount of to get nucleic acid, adds ultra-pure water and makes into nucleic acid solution, and nucleic acid concentration is 15～25mg/L.Get the above-mentioned nanoparticle suspension and the nucleic acid solution of equivalent respectively, the vortex mixing promptly gets the nucleic acid nano grain.
The solubility polybutylcyanoacrylate nanoparticle freeze-dried products that adopts said method to make; after media such as water redissolve; has nanometer particle character; can be used as nucleic acid carrier and be used for gene therapy; nucleic acid is played a protective role; prevent the DNA enzymatic degradation, improve the cell uptake rate, reach the purpose that suppresses tumor cell, treatment disease.
Compared with prior art, the invention has the advantages that:
1. solved the problem that to redissolve after such product dried of prior art for preparing.Adopt the resulting dry product of polybutylcyanoacrylate nanoparticle of technology preparation provided by the invention, after media such as water redissolve, the character of nanoparticle before keeping dry, it is regular to have form, and size is even, characteristics such as surperficial Zeta electric potential height.
2. the freeze-dried products of gained of the present invention carries nucleic acid efficient height, carries the nucleic acid ability before and after redissolving and does not reduce, and good stability can long preservation under the room temperature.
Description of drawings
Fig. 1 takes in the nucleic acid nano burl for laser co-focusing fluorescence microscope cell and really schemes.
Fig. 2 is that laser co-focusing fluorescence microscope cell is taken in free nucleic acid figure as a result.
Fig. 3 is the agarose gel electrophoresis analysis chart, and wherein the 1-6 sample is the sample behind the enzyme action, and 1 '-6 ' is the control sample of corresponding not enzyme action.
Embodiment 9 is seen in the explanation of accompanying drawing implication.
The specific embodiment
Below in conjunction with embodiment the present invention is further described, but is not limited to the following example.
Embodiment 1
Take by weighing 1.2 parts of DEAE-Dextran, 3.0 parts of Dextran-70, it is dissolved in pH is in 250 parts of hydrochloric acid solutions of 2.0, under stirring condition, to 1.6 parts of methyl 2-cyanoacrylate monomers of above-mentioned mixed solution and dripping, after dropwising, continue to stir 6h, add 25 parts of glucoses then, 10 parts in mannitol, stir 15min, promptly get paracyanogen base acrylic acid methyl ester. nanoparticle suspension; Under-40 ℃ low temperature, carry out the about 5h of pre-freeze, take out after finishing pre-freeze, put into freezer dryer rapidly and carry out lyophilization, remove fully, promptly get solubility paracyanogen base acrylic acid methyl ester. nanoparticle freeze-dried products, be white in color up to moisture, loose block.
The redissolution method: in use, it is a certain amount of to get the above-mentioned Poly(methyl cyanoacrylate) nano-granule freeze-dried powder that makes, and adds ultra-pure water and redissolves in right amount, becomes the nanoparticle suspension;
Leading indicator before and after table 1 paracyanogen base acrylic acid methyl ester. nanoparticle redissolves
| Sample | Particle diameter (nm) | Zeta electric potential (mv) | Carry the nucleic acid amount |
| Before the drying | 136.8 | 32.6 | 79.36μg/mg |
| After the redissolution | 135.9 | 31.8 | 78.98μg/mg |
Embodiment 2
Take by weighing 1.2 parts of DEAE-Dextran, 2.4 parts of Dextran-70, it is dissolved in pH is in 250 parts of hydrochloric acid solutions of 2.5, under stirring condition,, after dropwising, continue to stir 6h to the methyl 2-cyanoacrylate monomer of 2.3 parts of above-mentioned mixed solution and dripping, add 25 parts of glucoses then, 10 parts in mannitol stirs 15min, promptly gets paracyanogen base acrylic acid methyl ester. nanoparticle suspension; Under-40 ℃ low temperature, carry out the about 5h of pre-freeze, take out after finishing pre-freeze, put into freezer dryer rapidly and carry out lyophilization, remove fully, promptly get and freeze solubility paracyanogen base acrylic acid methyl ester. nanoparticle freeze-dried products, be white in color up to moisture, loose block.
The redissolution method is with embodiment 1.
Leading indicator before and after table 2 paracyanogen base acrylic acid methyl ester. nanoparticle redissolves
| Sample | Particle diameter (nm) | Zeta electric potential (mv) | Carry the nucleic acid amount |
| Before the drying | 145.6 | 34.2 | 81.6μg/mg |
| After the redissolution | 146.2 | 33.9 | 82.2μg/mg |
Embodiment 3
Take by weighing 1.5 parts of DEAE-Dextran, 1.5 parts of Dextran-70, it is dissolved in 100 parts of pH is in 2.2 the hydrochloric acid solution, under stirring condition,, after dropwising, continue to stir 4h to 2.6 parts of cyanacrylate monomers of above-mentioned mixed solution and dripping, add 20 parts of glucoses then, 15 parts in mannitol stirs 20min, promptly gets paracyanogen base ethyl acrylate nanoparticle suspension; Under-40 ℃ low temperature, carry out the about 5h of pre-freeze, take out after finishing pre-freeze, put into freezer dryer rapidly and carry out lyophilization, remove fully, promptly get solubility paracyanogen base ethyl acrylate nanoparticle freeze-dried products, be white in color up to moisture, loose block.
The redissolution method is with embodiment 1.
Leading indicator before and after table 3 paracyanogen base ethyl acrylate nanoparticle redissolves
| Sample | Particle diameter (nm) | Zeta electric potential (mv) | Carry the nucleic acid amount |
| Before the drying | 153.2 | 36.5 | 68.8μg/mg |
| After the redissolution | 153.8 | 35.9 | 67.6μg/mg |
Embodiment 4
Take by weighing 0.9 part of DEAE-Dextran, 1.5 parts of Dextran-70, it is dissolved in pH is in 120 parts of hydrochloric acid solutions of 2.3, under stirring condition,, after dropwising, continue to stir 8h to 1.2 parts of cyanacrylate monomers of above-mentioned mixed solution and dripping, add 15 parts of glucoses then, 10 parts in mannitol stirs 20min, promptly gets paracyanogen base ethyl acrylate nanoparticle suspension; Under-40 ℃ low temperature, carry out the about 5h of pre-freeze, take out after finishing pre-freeze, put into freezer dryer rapidly and carry out lyophilization, remove fully, promptly get solubility paracyanogen base ethyl acrylate nanoparticle freeze-dried products, be white in color up to moisture, loose block.
The redissolution method is with embodiment 1.
Leading indicator before and after table 4 paracyanogen base ethyl acrylate nanoparticle redissolves
| Sample | Particle diameter (nm) | Zeta electric potential (mv) | Carry the nucleic acid amount |
| Before the drying | 140.5 | 33.7 | 70.2μg/mg |
| After the redissolution | 142.2 | 32.3 | 71.3μg/mg |
Embodiment 5
Take by weighing 1.2 parts of DEAE-Dextran, 1.8 parts of Dextran-70, it is dissolved in 200 parts of pH is in 1.6 the hydrochloric acid solution, under stirring condition,, after dropwising, continue to stir 4h to the Tisuacryl monomer of 1.9 parts of above-mentioned mixed solution and dripping, add 25 parts of glucoses then, 12 parts in mannitol stirs 30min, promptly gets paracyanogen base butyl acrylate nanoparticle suspension; Under-40 ℃ low temperature, carry out the about 5h of pre-freeze, take out after finishing pre-freeze, put into freezer dryer rapidly and carry out lyophilization, remove fully, promptly get solubility paracyanogen base butyl acrylate nanoparticle freeze-dried products, be white in color up to moisture, loose block.
The redissolution method is with embodiment 1.
Leading indicator before and after table 5 paracyanogen base butyl acrylate nanoparticle redissolves
| Sample | Particle diameter (nm) | Zeta electric potential (mv) | Carry the nucleic acid amount |
| Before the drying | 145.6 | 35.7 | 85.9μg/mg |
| After the redissolution | 151.5 | 36.1 | 85.3μg/mg |
Embodiment 6
Take by weighing 1.2 parts of DEAE-Dextran, 2.4 parts of Dextran-70, it is dissolved in 180 parts of pH is in 1.6 the ml hydrochloric acid solution, under stirring condition,, after dropwising, continue to stir 4h to the Tisuacryl monomer of 1.6 parts of above-mentioned mixed solution and dripping, add 25 parts of glucoses then, 12 parts in mannitol stirs 30min, promptly gets paracyanogen base butyl acrylate nanoparticle suspension; Under-40 ℃ low temperature, carry out the about 5h of pre-freeze, take out after finishing pre-freeze, put into freezer dryer rapidly and carry out lyophilization, remove fully, promptly get solubility paracyanogen base butyl acrylate nanoparticle freeze-dried products, be white in color up to moisture, loose block.
The redissolution method is with embodiment 1.
Leading indicator before and after table 6 paracyanogen base butyl acrylate nanoparticle redissolves
| Sample | Particle diameter (nm) | Zeta electric potential (mv) | Carry the nucleic acid amount |
| Before the drying | 123.5 | 33.7 | 81.6μg/mg |
| After the redissolution | 125.9 | 32.3 | 80.8μg/mg |
Embodiment 7
Take by weighing 1.0 parts of DEAE-Dextran, 3.2 parts of Dextran-70, it is dissolved in 140 parts of pH is in 2.5 the hydrochloric acid solution, under stirring condition,, after dropwising, continue to stir 3h to the own ester monomer of the alpha-cyanoacrylate of 2.0 parts of above-mentioned mixed solution and dripping, add 20 parts of glucoses then, 6 parts in mannitol stirs 20min, promptly gets Poly(hexyl-2-cyanoacrylate) nanoparticle suspension; Under-50 ℃ low temperature, carry out the about 3h of pre-freeze, take out after finishing pre-freeze, put into freezer dryer rapidly and carry out lyophilization, remove fully up to moisture, dry product, be white in color, loose block.
The redissolution method is with embodiment 1.
Leading indicator before and after table 7 Poly(hexyl-2-cyanoacrylate) nanoparticle redissolves
| Sample | Particle diameter (nm) | Zeta electric potential (mv) | Carry the nucleic acid amount |
| Before the drying | 171.7 | 39.5 | 80.1μg/mg |
| After the redissolution | 169.5 | 38.1 | 79.6μg/mg |
Embodiment 8
Take by weighing 1.0 parts of DEAE-Dextran, 1.8 parts of Dextran-70, it is dissolved in 150 parts of pH is in 2.5 the hydrochloric acid solution, under stirring condition,, after dropwising, continue to stir 3h to the own ester monomer of the alpha-cyanoacrylate of above-mentioned mixed solution and dripping 1.8, add 16 parts of glucoses then, 4 parts in mannitol stirs 20min, promptly gets Poly(hexyl-2-cyanoacrylate) nanoparticle suspension; Under-45 ℃ low temperature, carry out the about 4h of pre-freeze, take out after finishing pre-freeze, put into freezer dryer rapidly and carry out lyophilization, remove fully up to moisture, dry product, be white in color, loose block.
The redissolution method is with embodiment 1.
Leading indicator before and after table 8 Poly(hexyl-2-cyanoacrylate) nanoparticle redissolves
| Sample | Particle diameter (nm) | Zeta electric potential (mv) | Carry the nucleic acid amount |
| Before the drying | 165.3 | 37.5 | 78.6μg/mg |
| After the redissolution | 166.2 | 36.9 | 78.3μg/mg |
Embodiment 9
The Poly(methyl cyanoacrylate) nano-granule freeze-dried powder of getting above-mentioned preparation freezes a certain amount of, adds ultra-pure water or normal saline or other pure water redissolve in right amount, and the concentration that makes nanoparticle is 200mg/L; It is a certain amount of to get nucleic acid, adds ultra-pure water and makes into 20mg/L.Get the above-mentioned nanoparticle suspension and the nucleic acid solution of equivalent respectively, vortex mixing 20min promptly gets the nucleic acid nano grain.
On 96 orifice plates, inoculate the A549 cell by 5 * 103/ holes.Inhale behind the 24h and abandon old culture medium, add new culture medium 50 μ L, above-mentioned gained nucleic acid nano grain is joined in the cell culture medium, and guarantee that total amount of liquid reaches 100 μ L in each holes of 96 orifice plates, and every hole inner nucleotide total amount concentration is 16 μ mol/L.Draw an amount of point of cell culture fluid on wave carrier piece with dropper behind the 30min, use the laser co-focusing fluorescence microscope.Accompanying drawing 1,2 shows: the nucleic acid nano grain is compared with free nucleic acid, cell intake showed increased.
Get a certain amount of nucleic acid nano grain and nucleic acid, add an amount of DNase respectively, mixing, the agarose gel electrophoresis analysis is carried out in 37 ℃ of waters bath with thermostatic control 30 minutes then.
Table 9 gel electrophoresis analysis experiment table
| Experiment numbers | 1 | 2 | 3 | 4 | 5 | 6 |
| DEAE-Dextran-NP(g/L) | 0.0 | 19.6 | 3.92 | 1.96 | 0.784 | 0.392 |
| ODN(mg/L) | 20 | 40 | 40 | 40 | 40 | 40 |
| Sampling amount (μ l) | 44.5 | 45 | 45 | 45 | 45 | 45 |
| DNase I addition (μ l) | 0.5 | 1 | 1 | 1 | 1 | 1 |
| 10 * DNase I Buffer addition (μ l) | 5 | 5 | 5 | 5 | 5 | 5 |
As can be seen from Figure 3, enzyme action reference substance 1 ' 4 ' 5 ' 6 ' the bright wisp band do not occur to positive extreme direction, and these bright wisp bands are free ODNs band; Enzyme action reference substance 2 ' 3 ' 4 ' 5 ' band do not occur at the initial point place, and these are the fluorescence that the ODNs on the nanoparticle is sent in conjunction with the back.Sample band do not occur in positive extreme direction behind the enzyme action, shows that free ODNs decomposes; There is similar result at negative pole direction and initial point place with corresponding reference substance, and this shows that DEAE-Dextran-NP can effectively suppress the enzymolysis of nuclease to ODNs, has the better protect effect to ODNs.
Claims (5)
1. solubility polybutylcyanoacrylate nanoparticle, it is characterized in that: mainly be made up of polybutylcyanoacrylate, DEAE-Dextran, Dextran-70, glucose and mannitol, the mass percent of each component is polybutylcyanoacrylate 2.0～16.3%, DEAE-Dextran 1.9～8.8%, Dextran-70 3.3～19.0%, glucose 30.3～79.6%, mannitol 8.3～52.8%.
2. described according to claim 1, it is characterized in that: said polybutylcyanoacrylate is a kind of in paracyanogen base acrylic acid methyl ester., paracyanogen base ethyl acrylate, paracyanogen base butyl acrylate or the Poly(hexyl-2-cyanoacrylate).
3. the preparation method of a solubility polybutylcyanoacrylate nanoparticle as claimed in claim 1, it is characterized in that: with glucose and mannitol is protective agent,
A. according to 0.9～1.5: 1.5～3.5 mass ratio takes by weighing totally 2～4.5 parts of DEAE-Dextran and Dextran-70; it is dissolved in 80～250 parts of pH is in 1.5～2.5 the hydrochloric acid solution; under stirring condition; to 1～3 part of above-mentioned mixed solution and dripping cyanoacrylate monomer, after dropwising, continue to stir 3～8h; add 10～25 parts of glucoses, 3～15 parts in mannitol then; stir 10～30min, get polybutylcyanoacrylate nanoparticle suspension
B. above-mentioned suspension is put into freezing chamber pre-freeze 1～5h of-30～-50 ℃, moisture is removed in lyophilization then, promptly gets product.
4. according to the preparation method of the described solubility polybutylcyanoacrylate of claim 3 nanoparticle, it is characterized in that: cyanoacrylate monomer is the methyl 2-cyanoacrylate monomer, the cyanacrylate monomer, a kind of in the own ester monomer of Tisuacryl monomer and alpha-cyanoacrylate.
5. the solubility polybutylcyanoacrylate nanoparticle that makes according to said method; it is characterized in that: solubility polybutylcyanoacrylate nanoparticle can be used as nucleic acid carrier and is used for gene therapy; nucleic acid is played a protective role; prevent the DNA enzymatic degradation; improve the cell uptake rate, reach the purpose that suppresses tumor cell.
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| CN110357994A (en) * | 2018-04-11 | 2019-10-22 | 北京化工大学 | A kind of preparation method of polybutylcyanoacrylate |
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| FR2841137B1 (en) * | 2002-06-20 | 2004-08-13 | Bioalliance Pharma | VECTORIZATION SYSTEM COMPRISING HOMOGENEOUS SIZE NANOPARTICLES OF AT LEAST ONE POLYMER AND AT LEAST ONE POSITIVELY CHARGED POLYSACCHARIDE |
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| CN110357994B (en) * | 2018-04-11 | 2020-11-20 | 北京化工大学 | Preparation method of polycyanoacrylate |
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