CN106474488A - A kind of superfine fibre film of load trimethyl chitosan chloride-polyethylene glycol-REDV/ nucleic acid and preparation method thereof - Google Patents
A kind of superfine fibre film of load trimethyl chitosan chloride-polyethylene glycol-REDV/ nucleic acid and preparation method thereof Download PDFInfo
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- CN106474488A CN106474488A CN201510534443.3A CN201510534443A CN106474488A CN 106474488 A CN106474488 A CN 106474488A CN 201510534443 A CN201510534443 A CN 201510534443A CN 106474488 A CN106474488 A CN 106474488A
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Abstract
The present invention relates to a kind of superfine fibre film of load trimethyl chitosan chloride polyethylene glycol REDV/ nucleic acid and preparation method.The superfine fibre film of load trimethyl chitosan chloride polyethylene glycol REDV/ nucleic acid, superfine nano tunica fibrosa is by the superfine fibre of a diameter of 300nm 900nm, with the trimethyl chitosan chloride polyethylene glycol REDV/ nucleic acid particle for containing intrastitial a diameter of below 100nm, 20 200 μm of composite membrane is formed.Trimethyl chitosan chloride polyethylene glycol REDV/ nucleic acid gel is introduced by fiber by emulsion electrospinning; the TMC PEG REDV/miRNA particle for discharging has the effect of target vascular therapy endothelial cell; trimethyl chitosan chloride polyethylene glycol REDV can realize the perfect cladding to miRNA; to protect the activity of miRNA, it is possible to control the rate of release of miRNA.
Description
Technical field
The present invention relates to a kind of superfine fibre film of load trimethyl chitosan chloride-polyethylene glycol-REDV/ nucleic acid and
Preparation method, belongs to organizational project and situ drug control release biomaterials art.
Background technology
Superfine nano tunica fibrosa has higher specific surface area, is commonly used for tissue engineering bracket.Biological degradability poly- third
Lactide copolymers such as polyethylene glycol-b- poly- (lactide-co- 6-caprolactone) (PELCL), poly- (lactide-co-glycolide)
(PLGA) etc., good biocompatibility, good mechanical performance.The PELCL prepared using electrospinning process is ultra-fine
Fiber electrospinning film, can be with analog cell epimatrix structure, can be used as the timbering material of tissue reconstruction.
SiRNA and miRNA is as the important regulating and controlling person of gene expression, rapid and high with specificity height, effect
The advantages of effect, in treatment tumour and vascular diseases, important positive role is played, paid close attention to by widely (Muthiah M,
Park I,Cho C.Nanoparticle-mediated delivery of therapeutic genes:focus on miRNA
therapeutics.Expert Opin.Drug Deliv 2013,10(9),1259-1273).SiRNA and miRNA itself
The degraded of nuclease is susceptible to, therefore research has the carrier compared with high transfection efficiency, carries gene and reach focus portion
Position and play gene effect very necessary.Using the polyethylene glycol containing double terminal functionality, can will be tri-methylated
Shitosan is connected with the polypeptide RVG with Brain targeting function, forms trimethyl chitin-grafting-polyethylene glycol
- RVG, contribute to realizing nucleic acid drug by blood-brain barrier and brain active targeting positioning (Jiang Tongying, Wang Siling,
Gao Yikun. a kind of trimethyl chitin-grafting-polyethylene glycol/nucleic acid Brain targeting micella and preparation method thereof .CN
103182087B,2015).On the other hand, the poly- (6-caprolactone-co- second that Rujitanaroj etc. is prepared by emulsion electrospinning
Base ethene phosphate) superfine fibre, nucleic acid can be directly loaded in nanofiber the realizing controlled-release in situ for realizing nucleic acid
Put, contribute to reparation (Rujitanaroj P, Jao B, Yang J, Wang F, the Anderson of long period regulation sufferer part
JM,Wang J,Chew SY.Controlling fibrous capsule formation through long-term
down-regulation of collagen type I(COL1A1)expression by nanofiber-mediated siRNA
gene silencing.Acta Biomaterialia,2013,9(1):4513-4524).But, due to nucleic acid pole in vivo
Degradable, it is highly important with certain activity after therefore protection nucleic acid is discharged by fiber.
Content of the invention
It is an object of the invention to provide a kind of load trimethyl chitosan chloride-polyethylene glycol-REDV/ nucleic acid is ultra-fine
Tunica fibrosa and preparation method, three in the superfine fibre film of the trimethyl chitosan chloride-polyethylene glycol-REDV/ nucleic acid
The activity of the nucleic acid release that the shitosan-polyethylene glycol-REDV that methylates is contained is higher.
The present invention is to be realized by the following technical scheme：Load trimethyl chitosan chloride-polyethylene glycol-REDV/
The superfine fibre film of nucleic acid, it is characterised in that the superfine nano tunica fibrosa is by the ultra-fine fibre of a diameter of 300nm-900nm
Dimension, and the trimethyl chitosan chloride-polyethylene glycol-REDV/ nucleic acid grain for containing intrastitial a diameter of below 100nm
Son, the thickness of formation are 20-200 μm of composite membrane.
Wherein superfine nano fiber is handed over poly- third by the trimethyl chitosan chloride-polyethylene glycol-REDV comprising nucleic acid
Ester copolymer is according to 1:(155-625) mass ratio composition, wherein per milligram of trimethyl chitosan chloride-polyethylene glycol
The amount that-REDV contains nucleic acid is 0.04-0.08mg.
The polylactide co polymer includes polyethylene glycol-b- poly- (lactide-co-caprolactone) or poly- (lactide-co- second
Lactide).
The nucleic acid is miRNA.
The number-average molecular weight of polyethylene glycol-b- poly- (lactide-co- 6-caprolactone) is (5-12) × 104, wherein lactide and
The mol ratio of 6-caprolactone is 3:1.
The number-average molecular weight of poly- (lactide-co-glycolide) is (5-12) × 104, wherein lactide and glycolide mole
Than for 3:1.
The preparation method of the superfine fibre film of above-mentioned load trimethyl chitosan chloride-polyethylene glycol-REDV/ nucleic acid, its are special
Levy and be to include procedure below：
(1) trimethyl of the water compound concentration for 4-10mg/mL is processed using pyrocarbonic acid diethyl ester (DEPC) under room temperature
Change shitosan-grafting-polyethylene glycol-REDV copolymer solution and mix standing with the nucleic acid of concentration 0.3-0.4mg/mL
20-40min, obtains trimethyl chitosan chloride-grafting-polyethylene glycol-REDV/ nucleic acid particle；
(2) with trimethyl chitosan chloride-grafting-polyethylene glycol that TE buffer concentration is 2-6.5mg/mL
- REDV/ nucleic acid particle is used as aqueous phase solution；
(3) poly- (lactide-co- 6-caprolactone) of polyethylene glycol-b- or poly- (lactide-co-glycolide) be dissolved in chloroform and
N,N-dimethylformamide is with volume ratio as 8:In 2 mixed solvent, the solution of concentration 50-200mg/mL is configured to
As oil-phase solution；
(4) will be 1 by volume by step (2) gained aqueous phase solution and step (3) gained oil-phase solution:(15-26), mix
30-60min, and the F127 by oil phase volume gauge addition 6-12mg/mL is closed, after obtaining homogeneous phase, carries out emulsion electricity
Spin,
Emulsion electrospinning condition is：The flow of mixed solution is 0.02-0.l mL/h, and the voltage of electrospinning is 14-19kV, connects
It is 13-20cm to receive distance, obtains the load trimethyl chitosan chloride-grafting-polyethylene glycol of 20-200 μ m thick
The superfine fibre film of-REDV/ nucleic acid.
Trimethyl chitosan chloride-grafting-polyethylene glycol-REDV (TMC-PEG-REDV) in preparation process (1)
Copolymer, its preparation method are comprised the following steps：
1) trimethyl chitosan chloride of deionized water difference compound concentration 10mg/mL and concentration 10-50 under room temperature
Two thiopyridines of neighbour of mg/mL-polyethylene glycol-succinimide acetic acid esters, mix reaction 3-10h and prepare front three
The adjacent two thiopyridines copolymer of base shitosan-grafting-polyethylene glycol-；
2) deionized water distinguishes the trimethyl chitosan chloride-grafting-polyethylene glycol-neighbour two of compound concentration 5mg/mL
Thiopyridines copolymer and the REDV of concentration 0.25-0.5mg/mL, mix reaction 2-6h and are obtained
TMC-PEG-REDV copolymer；
The weight average molecular weight of the shitosan is 50 × 104；The number-average molecular weight of polyethylene glycol is 3-5 × 103；
It is an advantage of the current invention that, by emulsion electrospinning by trimethyl chitosan chloride-polyethylene glycol-REDV/ nucleic acid gel
Fiber is introduced, preparation process is simple, the TMC-PEG-REDV/miRNA particle for discharging has targeting
The effect of vascular endothelial cell, the trimethyl chitosan chloride-poly- second in the polylactide co polymer superfine nano tunica fibrosa
Glycol-REDV can realize the perfect cladding to miRNA, to protect the activity of miRNA, it is possible to control
The rate of release of miRNA, and it is equally applicable to containing and discharge to other nucleic acid such as DNA, siRNA.
Description of the drawings
Fig. 1 is that the electric spinning superfine of the load trimethyl chitosan chloride-polyethylene glycol-REDV/ nucleic acid obtained by embodiment 1 is fine
Dimension film scanning electron micrograph；
Fig. 2 is that the electric spinning superfine of the load trimethyl chitosan chloride-polyethylene glycol-REDV/ nucleic acid obtained by embodiment 1 is received
Rice fiber transmission electron microscope photo.
Specific embodiment
Technical scheme is further described below by case study on implementation, following case study on implementation be to this
Further illustrating for invention, is not intended to limit the scope of application of the present invention.
Embodiment 1：
In the there-necked flask equipped with magnetic agitation, by 1g shitosan5.6 are added to 2.4g sodium iodide
ML mass fraction is in 15% mixed solution of NaOH and 40mL METHYLPYRROLIDONE, and adds 6
ML iodomethane, back flow reaction 45min at 60 DEG C.Add 15%NaOH solution and the 3mL of 5.6mL
Iodomethane, stirring reaction 45min.Add 40mL ethanol to carry out terminating reaction afterwards, product is filtered and used second
Ether is washed.Finally, product is dissolved in 40mL mass fraction for, in 10%NaCl solution, stirring 3h.Product makes
Deionized water dialysis 72h, is lyophilized and obtains trimethyl chitosan chloride (TMC).Take the TMC and 60mg of 20mg
Two thiopyridines of neighbour-polyethylene glycol-succinimide acetic acid estersAdd 2mL deionized water conduct
Solvent, reacts 6h at room temperature, and product dialysed using deionized water, be finally lyophilized obtain trimethyl chitosan chloride-
Grafting-polyethylene glycol-adjacent two thiopyridines copolymer.Trimethyl chitosan chloride-grafting-polyethylene glycol-neighbour in 10mg
In two thiopyridines copolymers and 0.8mg REDV-Cys small peptide, add the deionized water of 2mL and react 2h.Do not join
Plus the small peptide of reaction passes through centrifugal ultrafiltration removing of dialysing, TMC-PEG-REDV copolymer is obtained.
60 μ g of above-mentioned copolymer is mixed with 4 μ g of miRNA, and the 12 μ L of water after adding DEPC to process, room temperature stand
30min, obtains TMC-PEG-REDV/ nucleic acid nanoparticles, adds 8 μ L TE buffer solutions as aqueous phase solution.
Weigh 40mg PELCL (LA:CL=3:1,) and the F127 of 4mg be dissolved in 0.4mL chloroform and 0.1
As oil-phase solution in the mixed solvent of mL N,N-dimethylformamide.By water phase and oil-phase solution mixing 40min.
Emulsion electro-spinning process is:The flow of mixed solution is 0.04mL/h, and the electrospinning voltages of high-voltage DC power supply output are 15
KV, spinneret are 14cm with the reception distance of the aluminium foil being grounded, collect the superfine fibre of a diameter of 300-700nm
Pile up the tunica fibrosa for obtaining 20-200 μ m-thick.Load trimethyl chitosan chloride-polyethylene glycol obtained by this sample
The electric-woven super-fine fiber film scanning electron micrograph of-REDV/ nucleic acid as shown in Figure 1, obtained load trimethyl
Change electric spinning superfine nanofiber transmission electron microscope photo such as Fig. 2 institute of shitosan-polyethylene glycol-REDV/ nucleic acid
Show.This sample discharged activity miRNA 0.2 μ g/mg of totally 0.02 scholar (with respect to film weight) at the 28th day.
Embodiment 2：
Embodiment 1 is obtained TMC 20mg and adjacent two thiopyridines-polyethylene glycol-succinimide acetic acid esters100mg, adds 2mL deionized water as solvent, reacts 10h at room temperature.Product makes
Deionized water is dialysed, and is lyophilized and obtains trimethyl chitosan chloride-grafting-polyethylene glycol-adjacent two thiopyridines copolymer.?
Trimethyl chitosan chloride-grafting-the polyethylene glycol of 10mg-adjacent two thiopyridines copolymer and 1mg REDV-Cys small peptide
In, add the deionized water of 2mL and react 6h.The small peptide for not participating in reaction passes through centrifugal ultrafiltration removing of dialysing,
Prepared TMC-PEG-REDV copolymer.
60 μ g of above-mentioned copolymer is mixed with 4.5 μ g of miRNA, and the 15 μ L of water after adding DEPC to process, room temperature stand
20min, obtains TMC-PEG-REDV/ nucleic acid nanoparticles, adds 18 μ L of TE buffer solution, as aqueous phase solution.
Weigh 100mg PELCL (LA:CL=3:1,) and the F127 of 3mg be dissolved in 0.4mL chloroform and 0.1
As oil-phase solution in the mixed solvent of mL N,N-dimethylformamide.By water phase and oil-phase solution mixing 60min.
Emulsion electro-spinning process is:The flow of mixed solution is 0.02mL/h, and the electrospinning voltages of high-voltage DC power supply output are 14
KV, spinneret are 18cm with the reception distance of the aluminium foil being grounded, collect the superfine fibre of a diameter of 300-700nm
Pile up the tunica fibrosa for obtaining 20-200 μ m-thick.
Embodiment 3：
Embodiment 1 is obtained TMC 20mg and adjacent two thiopyridines-polyethylene glycol-succinimide acetic acid esters20mg, adds the mixing of 2mL deionized water, reacts 3h at room temperature.Product using go from
Sub- water dialysis, is lyophilized and obtains trimethyl chitosan chloride-grafting-polyethylene glycol-adjacent two thiopyridines copolymer.The three of 10mg
Methylate in shitosan-grafting-polyethylene glycol-adjacent two thiopyridines copolymer and 0.5mg REDV-Cys small peptide, add
The deionized water of 2mL simultaneously reacts 3h.The small peptide for not participating in reaction passes through centrifugal ultrafiltration removing of dialysing, and is obtained
TMC-PEG-REDV copolymer.
20 μ g of above-mentioned copolymer 1 is mixed with 4.8 μ g of miRNA, and the 12 μ L of water after adding DEPC to process, room temperature are quiet
40min is put, obtains TMC-PEG-REDV/ nucleic acid nanoparticles.7.2 μ L of TE buffer solution is added as water phase
Solution.Weigh 25mg PELCL ((LA:CL=3:1,) and the F127 of 6mg be dissolved in 0.4mL chlorine
As oil-phase solution in the mixed solvent of imitative and 0.1mL N,N-dimethylformamide.Water phase and oil-phase solution are mixed
30min.Emulsion electro-spinning process is:The flow of mixed solution is 1mL/h, the electrospinning voltages of high-voltage DC power supply output
For 17kV, spinneret is 15cm with the reception distance of the aluminium foil being grounded, collects the super of a diameter of 300-700nm
The tunica fibrosa for obtaining 20-200 μ m-thick piled up by fine fibre.
Embodiment 4
Embodiment 1 is obtained TMC 20mg and adjacent two thiopyridines-polyethylene glycol-succinimide acetic acid esters60mg mixes, and adds 2mL deionized water, reacts 6h at room temperature, and product is using going
Ionized water is dialysed, and is lyophilized and obtains trimethyl chitosan chloride-grafting-polyethylene glycol-adjacent two thiopyridines copolymer.In 10mg
Trimethyl chitosan chloride-grafting-polyethylene glycol-adjacent two thiopyridines copolymer and 0.8mg REDV-Cys small peptide in,
Add 2mL deionized water reaction 2h.The small peptide for not participating in reaction passes through centrifugal ultrafiltration removing of dialysing, and is obtained
TMC-PEG-REDV.
60 μ g of above-mentioned copolymer is mixed with 4 μ g of miRNA, and the 12 μ L of water after adding DEPC to process, room temperature stand
30min, obtains TMC-PEG-REDV/ nucleic acid nanoparticles.8 μ L of TE buffer solution is added, as aqueous phase solution.
Weigh 40mg PLGA ((LA:GA=3:1,) and the F127 of 4mg be dissolved in 0.4mL chloroform and 0.1
As oil-phase solution in the mixed solvent of mL N,N-dimethylformamide.By water phase and oil-phase solution mixing 40min.
Emulsion electro-spinning process is:The flow of mixed solution is 0.06mL/h, and the electrospinning voltages of high-voltage DC power supply output are 19
KV, spinneret are 20cm with the reception distance of the aluminium foil being grounded, collect the superfine fibre of a diameter of 300-700nm
Pile up the tunica fibrosa for obtaining 20-200 μ m-thick.
Disclosed by the invention a kind of load trimethyl chitosan chloride-polyethylene glycol-REDV/ nucleic acid superfine fibre film and
Preparation method, the superfine fibre film are made up of the superfine fibre of a diameter of 300nm-900nm, wherein superfine fibre by
(polyethylene glycol-b- is poly-, and (third hands over trimethyl chitosan chloride-polyethylene glycol-REDV/ nucleic acid particle with polylactide co polymer
Ester-co- 6-caprolactone) or poly- (lactide-co-glycolide)) constitute.Its preparation process includes:Prepare tri-methylated shell to gather
Sugar-polyethylene glycol-REDV copolymer；By trimethyl chitosan chloride-polyethylene glycol-REDV and miRNA in DEPC
Aqueous phase solution is incorporated as in the water of process again；Polylactide co polymer is dissolved in chloroform and N, N- dimethyl formyl
As oil-phase solution in the mixed solvent of amine；Obtained homogeneous to aqueous phase solution and oil-phase solution mixing by crossing emulsion electrospinning
To superfine fibre film.Preparation process is simple, containing load trimethyl chitosan chloride-poly- second in obtained superfine fibre film
Glycol-REDV/miRNA particle；The particle for discharging has the effect of target vascular therapy endothelial cell；Tri-methylated
Shitosan-polyethylene glycol-REDV and miRNA is combined, to protect the activity of miRNA, it is possible to control miRNA
Rate of release, and be equally applicable to containing and discharge to its nucleic acid such as DNA and siRNA.
Claims (8)
1. a kind of load trimethyl chitosan chloride-polyethylene glycol-REDV/ nucleic acid superfine fibre film, it is characterised in that this surpass
Thin nano fibrous membrane is by the superfine fibre of a diameter of 300nm-900nm, and contains intrastitial a diameter of 100nm
Following trimethyl chitosan chloride-polyethylene glycol-REDV/ nucleic acid particle, the thickness of formation are 20-200 μm answer
Close film.
2. superfine fibre film as claimed in claim 1, it is characterized in that described superfine nano fiber be by comprising nucleic acid
Trimethyl chitosan chloride-polyethylene glycol-REDV and polylactide co polymer are according to 1:(155-625) mass ratio composition；
The amount that wherein per milligram of trimethyl chitosan chloride-polyethylene glycol-REDV contains nucleic acid is 0.04-0.08mg.
3. superfine fibre film as claimed in claim 2, is characterized in that described polylactide co polymer is polyethylene glycol-b-
Poly- (lactide-co- 6-caprolactone) or poly- (lactide-co-glycolide).
4. superfine fibre film as claimed in claim 3, it is characterized in that described polyethylene glycol-b- poly- (lactide-co- ε-oneself
Lactone) number-average molecular weight be (5-12) × 104, the mol ratio of wherein lactide and 6-caprolactone is 3:1.
5. superfine fibre film as claimed in claim 3, is characterized in that the number of described poly- (lactide-co-glycolide) is divided equally
Son amount is (5-12) × 104, the mol ratio of wherein lactide and glycolide is 3:1.
6. superfine fibre film as claimed in claim 1, is characterized in that described nucleic acid is miRNA.
7. described in claim 1 load trimethyl chitosan chloride-polyethylene glycol-REDV/ nucleic acid superfine fibre film system
Preparation Method, it is characterised in that including procedure below：
(1) trimethyl chitosan chloride-poly- second two that water distinguishes compound concentration 4-10mg/mL is processed with DEPC under room temperature
Alcohol-REDV and the nucleic acid of concentration 0.3-0.4mg/mL, mixing standing 20-40min, obtain trimethyl chitosan chloride
- polyethylene glycol-REDV/ nucleic acid particle；
(2) TE buffer trimethyl chitosan chloride-polyethylene glycol-REDV/ nucleic acid particle concentration 2-6.5 is used
Mg/mL is used as aqueous phase solution；
(3) polylactide co polymer is dissolved in chloroform and N,N-dimethylformamide with volume ratio as 8:In 2 mixed solvent,
The solution of concentration 50-200mg/mL is configured to as oil-phase solution；
(4) will be 1 by volume by step (2) gained aqueous phase solution and step (3) gained oil-phase solution:(15-25), mix
30-60min, and the F127 of 6-12mg/mL is incorporated as by oil phase volume gauge, emulsion electricity is carried out after obtaining homogeneous phase
Spin, obtain 20-200 μ m thick loads the ultra-fine of trimethyl chitosan chloride-polyethylene glycol-REDV/ nucleic acid particle
Tunica fibrosa.
8. preparation method according to claim 7, it is characterised in that emulsion electrospinning condition is：The flow of mixed solution
For 0.02-0.1mL/h, the voltage of electrospinning is 14-19kV, and it is 13-20cm to receive distance.
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| CN108721699A (en) * | 2018-04-11 | 2018-11-02 | 天津大学 | A kind of the double-layer artificial blood vessel electrospinning material and preparation method of load miRNAs |
| CN109913977A (en) * | 2019-03-15 | 2019-06-21 | 中国科学院长春应用化学研究所 | A kind of nucleic acid gel fiber and preparation method thereof |
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| CN107551318A (en) * | 2017-07-06 | 2018-01-09 | 天津大学 | Contain the polylactide tunica fibrosa and preparation method of poly- (L lysines) the VAPG/ nucleic acid complexes of glucan g |
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| CN108619569A (en) * | 2018-04-11 | 2018-10-09 | 天津大学 | Three-layer artificial blood vessel electrospinning membrane loaded with micro nucleic acid and preparation method and application thereof |
| CN108721699A (en) * | 2018-04-11 | 2018-11-02 | 天津大学 | A kind of the double-layer artificial blood vessel electrospinning material and preparation method of load miRNAs |
| CN109913977A (en) * | 2019-03-15 | 2019-06-21 | 中国科学院长春应用化学研究所 | A kind of nucleic acid gel fiber and preparation method thereof |
| CN115885987A (en) * | 2022-09-08 | 2023-04-04 | 河南大学 | Targeted nano-carrier, preparation method and application thereof, targeted drug-loading nano-carrier and preparation method thereof |
| CN115885987B (en) * | 2022-09-08 | 2024-06-11 | 河南大学 | Targeting nano-carrier, preparation method and application thereof, targeting drug-loaded nano-carrier and preparation method thereof |
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