CN109498818A - A kind of pH sensitive liposome and preparation method thereof generating NO - Google Patents
A kind of pH sensitive liposome and preparation method thereof generating NO Download PDFInfo
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Abstract
The invention discloses a kind of pH sensitive liposomes and preparation method thereof for generating NO, it is that pH sensitive polymer PEG-PLL-DMA is coated on surface of liposome by electrostatic interaction, and hydrophily NO donor is loaded in intraliposomal aqueous phase, hydrophobic anticancer drug is contained by phospholipid bilayer, to construct the liposome that there is tumor tissues microenvironment pH sensibility and NO can be generated in tumour cell.
Description
Technical field
The invention belongs to biomedical material technologies, and in particular to a kind of pH sensitive liposome and its system for generating NO
Preparation Method.
Background technique
The generation of tumor multidrug-resistance is the major reason of oncotherapy failure.Drug resistance machine about tumour cell
System, viewpoint popular at present are the drug effluxes that P- glycoprotein (P-gp) is mediated.NO is a kind of gas molecule courier,
Key effect is played in various physiology courses.Importantly, NO can lower the expression of P-gp, so that it is swollen to play reverse
The effect of tumor multidrug resistance.It is reported that NO donor can be produced in tumour cell by stimulations such as enzyme, acidity, redox, light
Raw NO, but NO donor there are physiological stabilities poor, shortage targeting and tissue specificity, drug treating time are too short etc. asks
Topic, to limit its application as P-gp inhibitor.
Liposome is a kind of bilayer structure vesica being made of phosphatide, with good biocompatibility and biology
Availability can contain fat-soluble and water-soluble Medicine small molecule simultaneously.PH sensitive liposomes can be in tumor tissues or swollen
Drug release is inspired under the condition of acidic pH of oncocyte.The present invention combines the polymerization with tumor microenvironment (pH=6.5) pH sensitivity
Object PEG-PLL-DMA and NO donor can spontaneous generation NO the characteristics of, building can produce the pH sensitive liposome of NO, make it have
Charge overturning and the characteristic of spontaneous generation NO can occur in tumor tissues microenvironment, improve curative effect.
Summary of the invention
The purpose of the present invention is to provide a kind of pH sensitive liposomes for generating NO, and the liposome is in tumor tissues microenvironment
Intake of the charge overturning to promote tumour cell to liposome can occur, and NO can be generated simultaneously, with the medicine for inhibiting P-gp to mediate
Beyond the region of objective existence row, reverse multiple drug resistance of tumor.
To achieve the above object, the present invention adopts the following technical scheme:
A kind of pH sensitive liposome generating NO, contains cholesterol (Chol), hydrogenated soybean ovum in the phospholipid layer of the liposome
Phosphatide (HSPC), 1,2- distearyl acid -3- phosphatidyl-ethanolamine-polyethylene glycol 2000 (DSPE-PEG2000), (2,3- dioleoyl
Base-propyl)-trimethylamine (DOTAP) and hydrophobic anticancer drug, hydrophily NO donor has been contained in inner aqueous phase, and by quiet
PH sensitive polymer polyethylene glycol lysine-dimethyl maleic anhydride (PEG-PLL-DMA) is coated on lipid by electro ultrafiltration
Body surface face.
Wherein, HSPC, Chol, DSPE-PEG2000, DOTAP and hydrophobic anticancer drug molar ratio be 12:1:1:
(0.3~10):(0.1~5).The hydrophobic anticancer drug is in taxol, Docetaxel, camptothecine and vincristine
Any one.
HSPC, DOTAP and DSPE-PEG2000Quality sum and hydrophily NO donor used mass ratio be 10:1 ~
120:1.The hydrophily NO donor is diethylenetriamines NO nucleophilic complex (DETA NONOate), poly- nonyl dianhydride NO nucleophilic
Any one in reagent (PAPA NONOate) and spermine nitrogen oxidation adduct (Spermine NONOate).
HSPC, DOTAP and DSPE-PEG2000Quality sum and PEG-PLL-DMA used mass ratio be 1:1 ~ 1:
30。
It is described generate NO pH sensitive liposome preparation method the following steps are included:
(1) by HSPC, Chol, DSPE-PEG2000, DOTAP and hydrophobic anticancer drug be dissolved in chloroformic solution；
(2) chloroformic solution is removed by rotary evaporation, obtains uniform film material；
(3) after the PBS buffer solution elution with pH=8.0 containing 0.5 ~ 3 mM hydrophily NO donor, then ultrasonic cell-break is used
Instrument is ultrasonically treated 5-20 min under conditions of power is 100 ~ 400 W, contains NO donor and anti-tumor drug to be formed
Liposome；
(4) PEG-PLL-DMA is added, the h of 5 min ~ 8 is stirred at room temperature to get the pH sensitive liposome for generating NO.
Remarkable advantage of the invention is: the present invention is loaded with anti-altogether using pH sensitive polymer PEG-PLL-DMA cladding
The cationic-liposome of tumour medicine and NO donor makes gained pH sensitive liposome that charge can occur in tumor tissues microenvironment
Overturning, the intake in favor of tumour cell to liposome；After reaching tumour cell, the NO donor in intraliposomal aqueous phase is contained
Can spontaneous generation NO, not only can inhibit the drug efflux of P-gp mediation, and but also the permeability of liposome membrane can be improved, enhancing is contained in rouge
The anti-tumor drug of plastid phospholipid bilayer interlayer improves curative effect in the enrichment of tumour cell.
Detailed description of the invention
Fig. 1 is potential diagram of the pH sensitive liposome of generation NO prepared by embodiment 1 in the PBS of different pH value.
Specific embodiment
In order to make content of the present invention easily facilitate understanding, With reference to embodiment to of the present invention
Technical solution is described further, but the present invention is not limited only to this.
A kind of embodiment 1: preparation method for the pH sensitive liposome generating NO
(1) by Chol 2.01 mg, HSPC 47.03 mg, DSPE-PEG2000 13.75 mg, DOTAP 7.0 mg and taxols
4.05 mg are dissolved in 30 mL chloroformic solutions；
(2) Rotary Evaporators are utilized, 4 h are rotated with the revolving speed of 100 r/min at room temperature, obtain uniform film material；
(3) thin using ultrasonic wave after the PBS buffer solution elution with 6.78 mL, pH=8.0 containing 2.2 mM DETA NONOate
Born of the same parents are crushed instrument and are ultrasonically treated 10 min under conditions of power is 300 W, contain NO donor and anti-tumor drug to be formed
Liposome；
(4) with HSPC, DOTAP and DSPE-PEG2000Quality sum and PEG-PLL-DMA mass ratio be 1:6 be added
1 h is stirred at room temperature to get the pH sensitive liposome of NO is generated in PEG-PLL-DMA.
A kind of embodiment 2: preparation method for the pH sensitive liposome generating NO
(1) by Chol 2.01 mg, HSPC 47.03 mg, DSPE-PEG2000 13.75 mg, DOTAP 15.05 mg and Japanese yews
4.05 mg of alcohol is dissolved in 30 mL chloroformic solutions；
(2) Rotary Evaporators are utilized, 4 h are rotated with the revolving speed of 100 r/min at room temperature, obtain uniform film material；
(3) with after the PBS buffer solution elution containing 1.375 mM DETA NONOate of 7.58 mL, pH=8.0, ultrasound is utilized
Wave cell crushing instrument is ultrasonically treated 10 min under conditions of power is 300 W, has contained NO donor and antineoplastic to be formed
The liposome of object；
(4) with HSPC, DOTAP and DSPE-PEG2000Quality sum and PEG-PLL-DMA mass ratio be 1:30 be added
1 h is stirred at room temperature to get the pH sensitive liposome of NO is generated in PEG-PLL-DMA.
Embodiment 3: the potential measurement of the pH sensitive liposome of NO is generated
The pH sensitive liposome of generation NO prepared by embodiment 1 is diluted to by the PBS solution that pH=7.4,6.5 and 5.0 are respectively adopted
Concentration is 400 μ g/mL, measures its Zeta potential with Malvern laser particle analyzer, the result is shown in Figure 1.
As shown in Figure 1, in the PBS solution of pH=7.4, the Zeta potential of liposome is negative electrical charge；In pH=6.5 and 5.0
PBS solution in, charge overturning, which occurs, for liposome becomes positive charge, illustrates that prepared liposome has pH sensibility.
Embodiment 4: the extracorporeal releasing experiment of the pH sensitive liposome of NO is generated
In the case where meeting sink conditions, the PBS solution of liposome pH=8.0 prepared by 275 mL embodiments 1 is diluted to
1 mL, then immerses the PBS solution of 40 pH=7.4 mL, 6.5,5.0 respectively, and 37 DEG C, discharged under the conditions of 100 r/min；
0.5 mL release liquid is taken out respectively at preset time point (1,2,4,8,12,24,48,72,96,120 h), is supplemented simultaneously
The fresh PBS solution of equivalent；Drug is detected at 227 nm wavelength using HPLC after the appropriate dilution in acetonitrile of the release liquid of taking-up
Burst size calculates the preparation of taxol.
Experimental result is shown, when discharging 120 h, in the solution of pH=7.4, is generated the pH sensitive liposome of NO and is not wrapped
The burst size of taxol in the liposome of NO is carried all 30% or so；In the solution of pH=6.5, the pH sensitive liposome of NO is generated
The burst size of middle taxol increases to 70%, and the burst size of taxol is still below 53% in the liposome of unentrapped NO；In pH=5.0
Solution in, the burst size for generating taxol in the pH sensitive liposome of NO is up to 90%, taxol in the liposome of unentrapped NO
Burst size about 70%, the NO that result above further proves that the NO donor contained in liposome generates in acid condition can be bright
The aobvious release for promoting taxol in liposome.
The foregoing is merely presently preferred embodiments of the present invention, all equivalent changes done according to scope of the present invention patent with
Modification, is all covered by the present invention.
Claims (7)
1. a kind of pH sensitive liposome for generating NO, it is characterised in that: contain Chol, HSPC, DSPE- in liposomal phospholipids layer
PEG2000, DOTAP and hydrophobic anticancer drug, contained hydrophily NO donor in inner aqueous phase, and by electrostatic interaction by pH
Sensitive polymer PEG-PLL-DMA is coated on surface of liposome.
2. the pH sensitive liposome according to claim 1 for generating NO, it is characterised in that: HSPC, Chol, DSPE-
PEG2000, DOTAP and hydrophobic anticancer drug molar ratio be 12:1:1:(0.3 ~ 10): (0.1 ~ 5).
3. the pH sensitive liposome according to claim 1 or 2 for generating NO, it is characterised in that: the hydrophobicity is antitumor
Drug is any one in taxol, Docetaxel, camptothecine and vincristine.
4. the pH sensitive liposome according to claim 1 for generating NO, it is characterised in that: HSPC, DOTAP and DSPE-
PEG2000Quality sum and hydrophily NO donor used mass ratio be 10:1 ~ 120:1；
HSPC, DOTAP and DSPE-PEG2000Quality sum and PEG-PLL-DMA used mass ratio be 1:1 ~ 1:30.
5. the pH sensitive liposome according to claim 1 for generating NO, it is characterised in that: the hydrophily NO donor is
Any one in DETA NONOate, PAPA NONOate and Spermine NONOate.
6. a kind of method of the pH sensitive liposome of the generation NO prepared as described in claim 1-5 any one, feature exist
In: the following steps are included:
(1) by HSPC, Chol, DSPE-PEG2000, DOTAP and hydrophobic anticancer drug be dissolved in chloroformic solution；
(2) chloroformic solution is removed by rotary evaporation, obtains uniform film material；
(3) after being eluted with the PBS buffer solution of pH=8.0 NO containing hydrophily donor, then ultrasonic cell disruption instrument ultrasound 5- is used
20 min；
(4) PEG-PLL-DMA is added, the h of 5 min ~ 8 is stirred at room temperature to get the pH sensitive liposome for generating NO.
7. generating the preparation method of the pH sensitive liposome of NO according to claim 6, it is characterised in that: close in step (3)
The concentration of aqueous NO donor is 0.5 ~ 3 mM；Ultrasonic power is 100 ~ 400 W.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110179754A (en) * | 2019-06-12 | 2019-08-30 | 福州大学 | With redox responsiveness and the multi-functional liposome of tissue infiltration can be enhanced |
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2018
- 2018-05-25 CN CN201810515180.5A patent/CN109498818B/en not_active Expired - Fee Related
Patent Citations (5)
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|---|---|---|---|---|
| CN101001623A (en) * | 2004-06-10 | 2007-07-18 | 日本化药株式会社 | Anticancer effect enhancer |
| CN101766570A (en) * | 2010-01-18 | 2010-07-07 | 武汉大学 | PH-sensitive precursor cation nanometer liposome of target tumour cell and preparation method thereof |
| CN106177987A (en) * | 2016-08-17 | 2016-12-07 | 上海交通大学 | Little molecule macromolecule conjugates self assembly drug-loading nanoparticles and preparation method thereof |
| CN107049953A (en) * | 2017-06-05 | 2017-08-18 | 福州大学 | A kind of pH/ near infrared lights response bubble liposome and preparation method thereof |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110179754A (en) * | 2019-06-12 | 2019-08-30 | 福州大学 | With redox responsiveness and the multi-functional liposome of tissue infiltration can be enhanced |
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