CN108414393A - A method of measuring entrapment efficiency of liposome - Google Patents
A method of measuring entrapment efficiency of liposome Download PDFInfo
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- CN108414393A CN108414393A CN201810604773.9A CN201810604773A CN108414393A CN 108414393 A CN108414393 A CN 108414393A CN 201810604773 A CN201810604773 A CN 201810604773A CN 108414393 A CN108414393 A CN 108414393A
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- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N5/00—Analysing materials by weighing, e.g. weighing small particles separated from a gas or liquid
- G01N5/04—Analysing materials by weighing, e.g. weighing small particles separated from a gas or liquid by removing a component, e.g. by evaporation, and weighing the remainder
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Abstract
The invention discloses a kind of method measuring entrapment efficiency of liposome, had an effect using gel macromolecular and the liposome of oppositely charged to realize the measurement of encapsulation rate, the method includes the steps：（1）Measure the current potential of liposome；（2）According to the current potential surveyed, the gel of opposite charge therewith is selected, the gel of oppositely charged is added in liposome, after positive and negative charge neutralizes, formed bulky grain, centrifuge, stand, obtain supernatant and precipitation；（3）After taking precipitation, addition solvent that gel is made to dissolve, centrifugation is added organic solvent, so that liposome membrane is dissolved, release medicine out, measure the dose of encapsulating；（4）According to the dose of encapsulating, computational envelope rate.The present invention is had an effect with liposome using the gel of oppositely charged to realize the measurement of encapsulation rate, overcomes free drug in the prior art and entrapped drug separating degree is poor, the problem of measurement result inaccuracy.This method accuracy is high, reproducible, is suitble to promote and apply.
Description
Technical field
The invention belongs to pharmaceutical preparation and biotechnologies, and in particular to a kind of side measuring entrapment efficiency of liposome
Method.
Background technology
Liposome is a kind of novel pharmaceutical carrier, is a kind of bilayer structure of similar biofilm structure, lipid film
Mainly it is made of phosphatide that is natural or synthesizing.Different tissue and thin can be delivered to liposome by liposomal encapsulated drug
Born of the same parents are released medicine by destroying liposome membrane, target administration tissue.There is liposome targeting, biodegradable, nothing to exempt from
Epidemic focus improves the features such as medicine stability.At present evaluation liposome index include form with particles size and distribution, encapsulation rate,
Release in vitro etc., wherein encapsulation rate are one of the important indicators of liposome quality evaluation.
The measurement of liposome encapsulation is typically first to detach drug containing liposome with free drug, then passes through other methods
Directly or indirectly calculate its concentration.There are many ways to measuring encapsulation rate, including dialysis, supercentrifugation, gel filtration chromatography
Method, ion-exchange-resin process, ultrafiltration membrance filter method etc..Dialysis utilizes semi-permeable membrane molecular size difference, and the method is simple, repeats
Property it is good, but take it is longer, need to consume compared with multimedium, easily cause drug leakage.Supercentrifugation utilizes free drug and drug containing lipid
The gravity difference of body is detached, but this method cost is higher, and the time is longer, poor reproducibility, and reason may be due to centrifuging
In journey a part of small liposome lose or liposome in drug leakage lose.Gel filtration chromatography method is using liposome and to dissociate
The difference of drug relative molecular mass carries out detaching chromatographic column used being agarose Gel column and sephadex column, but exists
Elution time is long, volume is big, drug concentration is low etc..The mechanism of cation exchange resin processes is to be based on ion exchange, as long as i.e. object
Matter surface can be ion exchanged resin and be captured by ion exchange with the presence of tradable ion, therefore either free medicine
Object or drug crystalline substance or liposome fragment, can be detached by absorption with drug containing liposome.Ultrafiltration membrance filter method utilizes free
Drug can be by filter membrane, and drug containing liposome is trapped on filter membrane to detach free drug and liposome.The method filtration time
Length, filter membrane volume are big, drug concentration is not high.
In addition, when measuring liposome encapsulation, no matter centrifuges or filter, obtained solution is all more muddy, causes to tie
Fruit has very big error, influences the accuracy of result.
Invention content
In order to overcome the above-mentioned deficiencies of the prior art, the primary purpose of the present invention is that providing a kind of measurement liposome medicament
The method of encapsulation rate, this method is had an effect using the gel of oppositely charged with liposome to realize the measurement of encapsulation rate, accurate
Exactness is high, reproducible.
The present invention is achieved through the following technical solutions：
One of scheme proposed by the present invention：A method of entrapment efficiency of liposome is measured, the gel of oppositely charged is utilized
It is had an effect with liposome to realize the measurement of encapsulation rate, described method includes following steps：
（1）Measure the current potential of liposome；
（2）According to the current potential surveyed, the gel of opposite charge therewith is selected, the gel of oppositely charged is added to liposome
In,
After positive and negative charge neutralizes, bulky grain is formed, centrifugation obtains supernatant and precipitation；
（3）After taking precipitation, addition solvent that gel is made to dissolve, centrifugation is added organic solvent, so that liposome membrane is dissolved, by drug
It releases, measures the dose of encapsulating；
（4）According to the dose of encapsulating, direct computational envelope rate.
The gel of oppositely charged is added according to the current potential of liposome in the present invention in liposome（The electrification total amount of gel
It is identical as the charge number of liposome）, gel macromolecular and the liposome of oppositely charged are had an effect, due to the phase of positive and negative charge
It mutually combines, forms the particle of bigger, while reducing electrostatic charge, be more prone to assemble, through centrifugation, after liposome fully precipitates,
Organic solvent solubilizing lipids body film is added, the drug being encapsulated in liposome is released completely, realizes free drug and packet
Envelope drug is kept completely separate, and directly can quickly and accurately be surveyed according to the dose of encapsulating to measure the dose inside being encapsulated in
Make the encapsulation rate of liposome（EE%）, calculation formula is as follows：
EE% = WEncapsulating/ WAlways
Wherein, WEncapsulatingTo be encapsulated in the medication amount in liposome；
WAlwaysFor the drug total amount of addition.
Preferably, step（2）In, the rotating speed of the centrifugation is the rpm of 1000 rpm~10000, centrifugation time 5min~30
min。
The liposome of the present invention can be prepared according to this field customary preparation methods（Such as injection method）, in liposome preparation
In the process, according to the difference of used phospholipid material, positively charged liposome and electronegative liposome can be obtained, according to
The current potential surveyed can select electronegative gel if it is positively charged liposome；If it is negatively charged liposome
Positively charged gel can be selected, so that positive and negative charge neutralizes, forms the particle of bigger.
Preferably, the electronegative gel include chondroitin sulfate, hyaluronic acid, methylcellulose, ethyl cellulose,
The mixing of one or more of carboxymethyl cellulose, methylol third class cellulose or carbopol class；The positively charged gel
Including chitosan, cellulose nitrate ester, poly-l-lysine or the quaternary ammonium salt of synthesis polymer substance（Such as quaternary
Cationic polyvinyl alcohol, polymethacrylamide ethyl-benzyl-alkyl dimethyl ammonium chloride etc.）One or more of mixing.
Step（3）In, in precipitation, solvent is first added, it is therefore an objective to so that gel is dissolved, add organic solvent, make lipid
Body film dissolves, to release the drug being encapsulated in liposome completely.The solvent is gel dissolving solvent, according to
The property of gel is selected from the mixing of one or more of water, acetic acid etc.；The organic solvent is ethyl alcohol, chloroform, ether, first
The mixing of one or more of alcohol, acetone, n-hexane or aromatic hydrocarbon.
The two of scheme proposed by the present invention：
A method of entrapment efficiency of liposome is measured, is had an effect using gel and the liposome of oppositely charged to realize
The measurement of encapsulation rate, described method includes following steps：
（1）Measure the current potential of liposome；
（2）According to the current potential surveyed, the gel of opposite charge therewith is selected, the gel of oppositely charged is added to liposome
In,
After positive and negative charge neutralizes, bulky grain is formed, centrifugation obtains supernatant and precipitation；
（3）Supernatant is taken, non-encapsulated dose is measured；
（4）According to non-encapsulated dose, indirect computational envelope rate.
The gel of oppositely charged is added according to the current potential of liposome in the present invention in liposome（The electrification total amount of gel
It is identical as the charge number of liposome）, gel macromolecular and the liposome of oppositely charged are had an effect, due to the phase of positive and negative charge
It mutually combines, forms the particle of bigger, while reducing electrostatic charge, be more prone to assemble, through centrifugation, supernatant is very transparent, contains
There is non-encapsulated free drug, non-encapsulated dose is measured by ultraviolet or high-efficient liquid phase technique, according to non-encapsulated dose, indirectly
Determine the encapsulation rate of liposome（EE%）, calculation formula is as follows：
EE% = （WAlways-WIt does not encapsulate）/ WAlways
Wherein, WIt does not encapsulateNot to be encapsulated in the medication amount in liposome；
WAlwaysFor the drug total amount of addition.
Preferably, step（2）In, the rotating speed of the centrifugation is the rpm of 1000 rpm~10000, centrifugation time 5min~30
min。
Preferably, the gel includes positively charged gel and electronegative gel, and the electronegative gel includes sulphur
Aching and limp ossein, hyaluronic acid, methylcellulose, ethyl cellulose, carboxymethyl cellulose, methylol third class cellulose or carbopol
The mixing of one or more of class；The positively charged gel includes chitosan, cellulose nitrate ester, poly-l-lysine
Or the mixing of one or more of quaternary ammonium salt polymer substance of synthesis.
Compared with prior art, the present invention having the advantages that：
The present invention is had an effect with liposome using the gel of oppositely charged to realize the measurement of encapsulation rate, and existing skill is overcome
Free drug and entrapped drug separating degree are poor in art, the problem of measurement result inaccuracy.This method accuracy is high, reproducible,
It is suitble to promote and apply.
Specific implementation mode
It is further illustrated the present invention below by specific implementation mode, following embodiment is the specific embodiment party of the present invention
Formula, but embodiments of the present invention are not limited by following embodiments.
Embodiment 1：Paeonol soybean lipids body
A method of entrapment efficiency of liposome is measured, is had an effect using gel and the liposome of oppositely charged to realize
The measurement of encapsulation rate, described method includes following steps：
（1）The Paeonol soybean lipids bulk potential that measurement soybean lecithin, cholesterol etc. are prepared by injection method, it is negatively charged；
（2）According to the current potential surveyed, positively charged chitosan is selected, positively charged chitosan is added to Paeonol soybean
Fat
In plastid, bulky grain is formed, in 8000 rpm after positive and negative charge neutralization with the principle of phase coagulation using in positive and negative charge
10 min of lower centrifugation stand, obtain supernatant and precipitation；
（3）Precipitation is taken, is first dissolved chitosan with acetic acid, is centrifuged, ethyl alcohol, which is added, in precipitation makes liposome membrane dissolve, and drug is released
It releases, the dose W encapsulated using Syrups by HPLCEncapsulating；
（4）According to the dose of encapsulating, according to the direct computational envelope rate of formula：EE% = WEncapsulating/ WAlways。
Encapsulation rate and the rate of recovery, measurement result such as the following table 1 institute are measured to the Paeonol soybean lipids body of different lot numbers
Show：
Table 1：Direct Determination result
| Lot number | 20180316 | 20180318 | 20180320 |
| Encapsulation rate | 50.2% | 51.1% | 50.6% |
| The rate of recovery | 100.9% | 98.7% | 99.5% |
Embodiment 2：Paeonol soybean lipids body
A method of entrapment efficiency of liposome is measured, is had an effect using gel and the liposome of oppositely charged to realize
The measurement of encapsulation rate, described method includes following steps：
（1）The Paeonol soybean lipids bulk potential that measurement soybean lecithin, cholesterol etc. are prepared by injection method, it is negatively charged；
（2）According to the current potential surveyed, positively charged chitosan is selected, positively charged chitosan is added to Paeonol soybean
Fat
In plastid, bulky grain is formed, in 8000 rpm after positive and negative charge neutralization with the principle of phase coagulation using in positive and negative charge
10 min of lower centrifugation stand, obtain supernatant and precipitation；
（3）Supernatant is taken, using the non-encapsulated dose W of Syrups by HPLCIt does not encapsulate；
（4）According to non-encapsulated dose, according to the indirect computational envelope rate of formula：EE% = （WAlways-WIt does not encapsulate）/ WAlways。
Encapsulation rate and the rate of recovery, measurement result such as the following table 2 institute are measured to the Paeonol soybean lipids body of different lot numbers
Show：
Table 2：Indirect Determination result
| Lot number | 20180316 | 20180318 | 20180320 |
| Encapsulation rate | 50.1% | 51.1% | 50.7% |
| The rate of recovery | 100.6% | 98.5% | 99.6% |
The data that both indirect method and direct method obtain it can be seen from Tables 1 and 2 result are almost the same, poor without statistics
It is different.Moreover, the free dose in supernatant is close with drug total amount plus the dose encapsulated in liposome, further illustrates and use
The method of the gel determination liposome encapsulation of opposite charges is accurate, is suitble to promote and apply.
Embodiment 3：Docetaxel DSPE-PEG (2000)-maleimide liposomes
A method of entrapment efficiency of liposome is measured, is had an effect using gel and the liposome of oppositely charged to realize
The measurement of encapsulation rate, described method includes following steps：
（1）It is prepared into liposome in pH7.4 buffer solutions according to DOTAP and DSPE-PEG (2000)-maleimide different proportions,
The current potential of liposome is measured, it is positively charged；
（2）According to the current potential surveyed, electronegative chondroitin is selected, negatively charged chondroitin is added in liposome, profit
With in positive and negative charge and the principle of phase coagulation, after positive and negative charge neutralizes, bulky grain is formed, 15 are centrifuged under 6000 rpm
Min stands, obtains supernatant and precipitation；
（3）Precipitation is taken, be dissolved in water chondroitin, and centrifugation, ethyl alcohol or chloroform, which is added, in precipitation makes liposome membrane dissolve, and drug is released
It releases, measures the dose W of encapsulatingEncapsulating；
（4）According to the dose of encapsulating, according to formula computational envelope rate：EE% = WEncapsulating/ WAlways。
To Docetaxel DSPE-PEG (2000)-maleimide liposomes of different lot numbers be measured encapsulation rate and
The rate of recovery,
Measurement result is as shown in table 3 below：
Table 3：Measurement result
| Lot number | 20180411 | 20180417 | 20180425 |
| Encapsulation rate | 56.8% | 59.0% | 57.2% |
| The rate of recovery | 98.4% | 99.1% | 99.4% |
Comparative example 1 measures the encapsulation rate of Paeonol soybean lipids body using gel filtration chromatography method
Using sephadex column chromatography（With reference to CN200510033324.6）To the Paeonol soybean lipids body of identical lot number
It is measured, measurement result is as shown in table 4 below：
4 measurement result of table
| Lot number | 20180316 | 20180318 | 20180320 |
| Encapsulation rate | 48.8% | 42.5% | 53.7% |
| The rate of recovery | 90.4% | 94.1% | 97.8% |
The method application molecular sieve principle, needs by pre-processing, filling column, sample-adding, elution and receipts it can be seen from 4 result of table
The process of the regeneration and recycling of collection, gel, separation Paeonol soybean lipids body and free Paeonol, complicated for operation, the time is long,
Cause result error big in the presence of the reasons such as incomplete are eluted.
Claims (8)
1. a kind of method measuring entrapment efficiency of liposome, which is characterized in that utilize the gel and liposome of oppositely charged
It has an effect to realize the measurement of encapsulation rate, described method includes following steps：
（1）Measure the current potential of liposome；
（2）According to the current potential surveyed, the gel of opposite charge therewith is selected, the gel of oppositely charged is added to liposome
In,
After positive and negative charge neutralizes, bulky grain is formed, centrifugation obtains supernatant and precipitation；
（3）After taking precipitation, addition solvent that gel is made to dissolve, centrifugation is added organic solvent, so that liposome membrane is dissolved, by drug
It releases, measures the dose of encapsulating；
（4）According to the dose of encapsulating, direct computational envelope rate.
2. a kind of method measuring entrapment efficiency of liposome according to claim 1, which is characterized in that step（2）In,
1000 rpm of rotating speed~10000rpm of the centrifugation, centrifugation time 5min~30 min.
3. a kind of method measuring entrapment efficiency of liposome according to claim 1, which is characterized in that step（2）In,
The gel includes positively charged gel and electronegative gel, and the electronegative gel includes chondroitin sulfate, thoroughly
One kind in bright matter acid, methylcellulose, ethyl cellulose, carboxymethyl cellulose, methylol third class cellulose or carbopol class
Or several mixing；The positively charged gel includes chitosan, cellulose nitrate ester, poly-l-lysine or the season of synthesis
The mixing of one or more of ammonium salt family macromolecule substance.
4. a kind of method measuring entrapment efficiency of liposome according to claim 1, which is characterized in that step（3）In,
The organic solvent is the mixing of one or more of ethyl alcohol, chloroform, ether, methanol, acetone, n-hexane or aromatic hydrocarbon.
5. a kind of method measuring entrapment efficiency of liposome according to claim 1, which is characterized in that step（3）In,
The solvent is gel dissolving solvent, and the mixing of one or more of water, acetic acid is selected from according to the property of gel.
6. a kind of method measuring entrapment efficiency of liposome, which is characterized in that utilize the gel and liposome of oppositely charged
It has an effect to realize the measurement of encapsulation rate, described method includes following steps：
（1）Measure the current potential of liposome；
（2）According to the current potential surveyed, the gel of opposite charge therewith is selected, the gel of oppositely charged is added to liposome
In,
After positive and negative charge neutralizes, bulky grain is formed, centrifugation obtains supernatant and precipitation；
（3）Supernatant is taken, non-encapsulated dose is measured；
（4）According to non-encapsulated dose, indirect computational envelope rate.
7. a kind of method measuring entrapment efficiency of liposome according to claim 6, which is characterized in that step（2）In,
1000 rpm of rotating speed~10000rpm of the centrifugation, centrifugation time 5min~30 min.
8. a kind of method measuring entrapment efficiency of liposome according to claim 6, which is characterized in that step（2）In,
The gel includes positively charged gel and electronegative gel, and the electronegative gel includes chondroitin sulfate, hyalomitome
Acid, methylcellulose, ethyl cellulose, carboxymethyl cellulose, methylol third class cellulose or one kind or several in carbopol class
The mixing of kind；The positively charged gel includes chitosan, cellulose nitrate ester, poly-l-lysine or the quaternary ammonium salt of synthesis
The mixing of one or more of family macromolecule substance.
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Cited By (2)
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| CN113358836A (en) * | 2021-04-30 | 2021-09-07 | 北京诺康达医药科技股份有限公司 | Method for measuring encapsulation efficiency of drug-loaded fat emulsion |
| CN115436515A (en) * | 2022-09-05 | 2022-12-06 | 石家庄四药有限公司 | Detection method for entrapment rate of miboplatin liposome |
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Application publication date: 20180817 |