CN103142457A - Resveratrol nanometer-preparation preparation method - Google Patents
Resveratrol nanometer-preparation preparation method Download PDFInfo
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- CN103142457A CN103142457A CN2013100181375A CN201310018137A CN103142457A CN 103142457 A CN103142457 A CN 103142457A CN 2013100181375 A CN2013100181375 A CN 2013100181375A CN 201310018137 A CN201310018137 A CN 201310018137A CN 103142457 A CN103142457 A CN 103142457A
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Abstract
The invention discloses a resveratrol nanometer-preparation preparation method. The method includes a first step of utilizing a certain amount of organic solvent to fully dissolve a certain percentage of resveratrol and polyethylene glycol derivatives, a second step of dripping a certain number of surface active agents to a certain amount of deionized water, a third step of dripping resveratrol and organic solvent mixed liquor into the deionized water at a fixed dripping speed at the appropriate rotational speed, and a fourth step of enabling reaction to be continued for a certain time after dripping is completed and finally obtaining resveratrol water-soluble nanometer preparation when the organic solvent is dried through rotation. The resveratrol nanometer-preparation preparation method is simple in conditions and procedures. The resveratrol nanometer preparation through the method has the advantages of being small in particle size, high in drug loading capacity, good in monodispersity and stability, free of toxic and side effects and high in safety, and has a remarkable result in treatment of acute enteritis.
Description
Technical field
The present invention relates to a kind of preparation method of resveratrol nanometer formulation.
Background technology
Resveratrol is polyphenol compound, be mainly derived from the rhizome extract of polygonaceae plant Rhizoma Polygoni Cuspidati (Polygonum cuspidatum Sieb.et Zucc), it is a kind of natural antioxidant, can reduce blood viscosity, anti-platelet clotting and vasodilation keep unblocked blood flowing, but the generation of prophylaxis of cancer and development, has atherosclerosis and coronary heart disease, ischemic heart desease, the preventive and therapeutic effect of hyperlipidemia.
The nineties in 20th century; the Chinese science and technology worker deepens continuously to the research of resveratrol; and disclose its pharmacological action: suppress the improper cohesion of platelet; prevention myocardial infarction, cerebral embolism; the anoxia heart there is protective effect; can play the overweight people and control and antiobesity action, the cardiac output that burn or hemorrhagic shock are caused descends efficient recovery is arranged, and can the expansion artery blood vessel and improve microcirculation.Jayafilake etc. studies show that trans-resveratrol and cis-resveratrol. all have active anticancer, and its reason is the activity that they can Profilin matter-tyrosine kinase.The research groups such as Jang further point out, resveratrol has larger anti-cancer active in i.e. initial, the enhancement of 3 stages that cancer occurs and evolution, and 3 stages are occured cancer have and suppress and even reverse effect: one, suppress initiation.Reduce free radical and form, induce II phase medicine to increase for enzyme, the effect of antagonism dioxin; Two, suppress the enhancement effect.Suppress cyclooxygenase (COX), suppress catalase; Three effects of holding back the development.Anticancer propagation, inducing cancer cell differentiation, cancer cell specific induction of apoptosis.Resveratrol is expected the inhibitor as tyrosine protein kinase PTK, and many medical researches find that resveratrol all has obvious inhibitory action to Several Kinds of Malignancy cells such as breast carcinoma, gastric cancer, colon cancer, carcinoma of prostate, leukemia, ovarian cancer, skin carcinomas.
Carry by gastrointestinal tract in order to make any curative drug molecular substance, enter blood and final intracorporeal organ and the cell of arriving, described drug molecule must be soluble at the aqueous phase of intestinal juice, if do not dissolve or dissolubility lower, drug molecule will pass through gastrointestinal tract as block dust; And resveratrol is almost insoluble in water, and peroral administration animal pharmaceuticals dynamics research has proved that the bioavailability of resveratrol is extremely low.Therefore, improve clinically resveratrol water solublity or bioavailability and seem very necessary.
At present, most of patent about resveratrol relates to that it extracts with the preparation aspect, and only have small part to relate to the preparation method of resveratrol nanometer formulation, and as: Chinese invention patent " a kind of immobilized enzyme converting giant knotweed materials improves the method for Resveratrol content " (CN201010022075.1) discloses a kind of method that immobilized enzyme converting giant knotweed materials improves Resveratrol content; Chinese invention patent " the resveratrol preparation that biological activity improves " (CN200980152936.3) discloses the water miscible method of raising resveratrol, and described preparation can be used for treating cancer at interior morbid state; Chinese invention patent " a kind of preparation technology of water-soluble resveratrol particle and goods thereof and application " (CN200810154556.0) discloses a kind of method for preparing the higher resveratrol particle of water solublity; Chinese invention patent " PEG, mPEG chemical modification and prepare the method for water-soluble resveratrol prodrug " (CN201010199655.8) discloses a kind of PEG, mPEG chemical modification and has prepared the method for water-soluble resveratrol prodrug; Chinese invention patent " a kind of resveratrol nanometer formulation and preparation method thereof " (CN201010592579.7) discloses a kind of method of utilizing oils to prepare the resveratrol nanometer formulation.Yet there are no relevant report and the present invention prepares the technique of resveratrol nanometer formulation, especially resveratrol does not yet have similar report in the patent aspect the acute enteritis treatment.
Summary of the invention
The present invention aims to provide a kind of preparation method of resveratrol nanometer formulation, and it is high that the resveratrol nanometer formulation that the method is prepared has a drug loading, good stability, treatment acute enteritis effect outstanding feature.
For reaching above purpose, the present invention takes following technical scheme to be achieved.
1. the preparation method of a resveratrol nanometer formulation, is characterized in that, comprises the steps:
(1) take the resveratrol of 1-15mg and the polyethyleneglycol derivative of 1-30mg, be dissolved in the 1-5ml organic solvent, and under 100HZ ultrasonic 2-8 minute, mixed liquor formed; Described polyethyleneglycol derivative is HOOC-PEG-COOH, MPEG-OH, H
3N-PEG-NH
3, H-[OCHCH
3CO]
nAny one in-OH; Described organic solvent is any one in methanol, acetone, ether, ethanol;
(2) deionized water of weighing 1-30ml adds surfactant by mass volume ratio at 1: 5000, and mixing speed is 40-80r/min; At 25 ℃ of-65 ℃ of temperature, drip mixed liquor so that dripping of 0.001-0.1ml/s is fast in deionized water; After dropwising, reduce rotating speed, continue to stir 90-240min; Described surfactant is any one in SE-10, TWEEN20, NP-6 (OP-6), PEG-200.
2. the preparation method of a kind of resveratrol nanometer formulation according to claim 1, is characterized in that, described polyethyleneglycol derivative is HOOC-PEG-COOH, MPEG-OH, H
3N-PEG-NH
3, H-[OCHCH
3CO]
nAny one in-OH.
3. the preparation method of a kind of resveratrol nanometer formulation according to claim 1, is characterized in that, described organic solvent is any one in methanol, acetone, ether, ethanol.
4. the preparation method of a kind of resveratrol nanometer formulation according to claim 1, is characterized in that, the mass volume ratio of described resveratrol, polyethyleneglycol derivative and deionized water is 1: 1: 1-3: 2: 2.
5. the preparation method of a kind of resveratrol nanometer formulation according to claim 1, is characterized in that, described in step (2), rotating speed is 0.001-0.1ml/s.
In such scheme, described polyethyleneglycol derivative is HOOC-PEG-COOH, MPEG-OH, H
3N-PEG-NH
3, H-[OCHCH
3CO]
nAny one in-OH; Described organic solvent is any one in methanol, acetone, ether, ethanol; The mass volume ratio of described resveratrol, polyethyleneglycol derivative and deionized water is 1: 1: 1-3: 2: 2; Described in step (2), rotating speed is 0.001-0.01ml/s.
The preparation method of a kind of resveratrol nanometer formulation of the present invention has following obvious effect: the little and particle size range narrowly distributing of (1) preparation particle diameter; (2) preparation stability and monodispersity are good; (3) long (3) the preparation drug loading of preparation effective drug duration is up to 98%, and bioavailability is high, has the effect of obvious treatment enteritis.
Description of drawings
The present invention is described in further detail below in conjunction with accompanying drawing table and embodiment.
Fig. 1 is particle size distribution figure and the transmission electron microscope picture of the prepared resveratrol nanometer formulation of example 1 of the present invention, the resveratrol nanometer formulation form homogeneous that makes of the present invention as seen from the figure, and particle diameter is little, and particle size distribution range is narrow, and monodispersity is good.
Fig. 2 is the Zeta potential figure of the prepared resveratrol nanometer formulation of example 3 of the present invention, and the resveratrol nanometer formulation monodispersity that makes of the present invention is good as seen from the figure.
Fig. 3 is that the prepared resveratrol nanometer formulation of example 8 of the present invention is at external drug release curve, the release of the resveratrol nanometer formulation that makes of the present invention is slow as seen from the figure, satisfy the requirement of vivo medicine-feeding fully, this nanometer formulation has good stability simultaneously, and the amount of leakage of placing 30 days is very low.
Fig. 4 be the prepared resveratrol nanometer formulation of example 9 of the present invention to the degree of impairment of intestinal, A is normal intestinal tissue; Acute enteritis intestinal tissue after the administration of B resveratrol; C is the intestinal tissue after the administration of resveratrol nanometer formulation, and as seen from the figure, resveratrol is through after changing administering mode, and the treatment of acute enteritis is had obvious effect.
The specific embodiment
In order to make purpose of the present invention, technical scheme and advantage clearer, below in conjunction with drawings and Examples, the present invention is further elaborated.Should be appreciated that specific embodiment described herein only in order to explain the present invention, is not intended to limit the present invention.
Embodiment 1
With precision balance weighing 1mg resveratrol and 1mgHOOC-PEG-COOH, be dissolved in 1ml methanol, under 100HZ ultrasonic 2 minutes, form mixed liquor; With graduated cylinder weighing 1ml deionized water, and add 0.0005ml surfactant SE-10 in deionized water, stir with the rotating speed of 40r/min; Stir after 5 minutes, under 25 ℃, drip mixed liquor so that dripping of 0.01ml/s is fast in deionized water; After dropwising, mixed solution is the light oyster white glue; Reacted 60 minutes, and revolved and steam and remove methanol, namely obtain the resveratrol nanometer formulation, glue is creamy white.
With precision balance weighing 5mg resveratrol and 10mgMPEG-OH, be dissolved in 2ml acetone, under 100HZ ultrasonic 4 minutes, form mixed liquor; With graduated cylinder weighing 10ml deionized water, and add 0.005ml surfactant Tween20 in deionized water, stir with the rotating speed of 50r/min; Stir after 5 minutes, under 30 ℃, drip mixed liquor so that dripping of 0.001ml/s is fast in deionized water; After dropwising, mixed solution is the light oyster white glue; Reacted 180 minutes, and revolved and steam and remove acetone, namely obtain the resveratrol nanometer formulation, glue is creamy white.
Embodiment 3
With precision balance weighing 5mg resveratrol and 5mg H
3N-PEG-NH
3, be dissolved in the 2ml ether, under 100HZ ultrasonic 4 minutes, form mixed liquor; With graduated cylinder weighing 10ml deionized water, and add 0.005ml Surfactant PEG-200 in deionized water, stir with the rotating speed of 60r/min; Stir after 5 minutes, under 35 ℃, drip mixed liquor so that dripping of 0.01ml/s is fast in deionized water; Reacted 120 minutes, and revolved and steam and remove ether, namely obtain the resveratrol nanometer formulation, glue is creamy white.
Embodiment 4
With precision balance weighing 10mg resveratrol and 5mgH-[OCHCH
3CO]
n-OH is dissolved in 4ml ethanol, under 100HZ ultrasonic 5 minutes, forms mixed liquor; With graduated cylinder weighing 5ml deionized water, and add 0.0001ml surfactant NP-6 (OP-6) in deionized water, stir with the rotating speed of 70r/min; Stir after 5 minutes, under 40 ℃, drip mixed liquor so that dripping of 0.01ml/s is fast in deionized water; After dropwising, mixed solution is the light oyster white glue; Reacted 90 minutes, and revolved and steam and remove ethanol, namely obtain the resveratrol nanometer formulation, glue is creamy white
With precision balance weighing 5mg resveratrol and 10mgMPEG-OH, be dissolved in 2ml acetone, under 100HZ ultrasonic 4 minutes, form mixed liquor; With graduated cylinder weighing 10ml deionized water, and add 0.005ml surfactant Tween20 in deionized water, stir with the rotating speed of 80r/min; Stir after 5 minutes, under 45 ℃, rotating speed is down to 40r/min, drips mixed liquor so that dripping of 0.001ml/s is fast in deionized water; After dropwising, mixed solution is the light oyster white glue; Reacted 240 minutes, and revolved and steam and remove acetone, namely obtain the resveratrol nanometer formulation, glue is creamy white.
Table 1 is the Stability Observation table of the prepared resveratrol nanometer formulation of example 5 of the present invention, and the resveratrol nanometer formulation particle diameter and the drug leakage amount temporal evolution that make of the present invention is very little as seen from table, has good stability.
Table 1
Embodiment 6
With precision balance weighing 10mg resveratrol and 10mgHOOC-PEG-COOH, be dissolved in 5ml methanol, under 100HZ ultrasonic 8 minutes, form mixed liquor; With graduated cylinder weighing 5ml deionized water, and add 0.0001ml Surfactant PEG-200 in deionized water, stir with the rotating speed of 80r/min; Stir after 5 minutes, under 50 ℃, rotating speed is down to 50r/min, drips mixed liquor so that dripping of 0.1ml/s is fast in deionized water; Reacted 120 minutes, and revolved and steam and remove methanol, namely obtain the resveratrol nanometer formulation, glue is creamy white.
Embodiment 7
With precision balance weighing 5mg resveratrol and 10mg H
3N-PEG-NH
3, be dissolved in the 2ml ether, under 100HZ ultrasonic 4 minutes, form mixed liquor; With graduated cylinder weighing 10ml deionized water, and add 0.005ml surfactant SE-10 in deionized water, stir with the rotating speed of 50r/min; Stir after 5 minutes, under 55 ℃, drip mixed liquor so that dripping of 0.001ml/s is fast in deionized water; After dropwising, mixed solution is the light oyster white glue; Reacted 240 minutes, and revolved and steam and remove ether, namely obtain the resveratrol nanometer formulation, glue is creamy white.
Embodiment 8
With precision balance weighing 15mg resveratrol and 30mgMPEG-OH, be dissolved in 5ml acetone, under 100HZ ultrasonic 8 minutes, form mixed liquor; With graduated cylinder weighing 30ml deionized water, and add 0.01ml surfactant Tween20 in deionized water, stir with the rotating speed of 50r/min; Stir after 5 minutes, under 60 ℃, drip mixed liquor so that dripping of 0.01ml/s is fast in deionized water; After dropwising, mixed solution is the light oyster white glue; Reacted 240 minutes, and revolved and steam and remove acetone, namely obtain the resveratrol nanometer formulation, glue is creamy white.
Embodiment 9
With precision balance weighing 15mg resveratrol and 10mgMPEG-OH, be dissolved in 5ml ethanol, under 100HZ ultrasonic 8 minutes, form mixed liquor; With graduated cylinder weighing 10ml deionized water, and add 0.005ml surfactant Tween20 in deionized water, stir with the rotating speed of 60r/min; Stir after 5 minutes, under 65 ℃, drip mixed liquor so that dripping of 0.1ml/s is fast in deionized water; After dropwising, mixed solution is the light oyster white glue; Reacted 120 minutes, and revolved and steam and remove ethanol, namely obtain the resveratrol nanometer formulation, glue is creamy white.
The resveratrol nanometer formulation of preparation waits and characterizes with Particle Size Analyzer, transmission electron microscope, zeta potential instrument, HE dyeing, and experimental result shows: the resveratrol nanometer formulation particle diameter of preparing is little, form homogeneous, monodispersity and having good stability; Drug loading is up to 98%, and effective drug duration is long in vivo, and bioavailability is high.And the resveratrol nanometer formulation of preparation has been carried out pharmacological evaluation: set up 20 of acute enteritis mouse models, gavage is after 30 days continuously, put to death mice, through pathological section, experimental result shows that the resveratrol nanometer formulation treatment acute enteritis effect of preparation is remarkable.
The above is only preferred embodiment of the present invention, not in order to limiting the present invention, all any modifications of doing within the spirit and principles in the present invention, is equal to and replaces and improvement etc., within all should being included in protection scope of the present invention.
Claims (7)
1. the preparation method of a resveratrol nanometer formulation, is characterized in that, comprises the steps:
(1) take the resveratrol of 1-15mg and the polyethyleneglycol derivative of 1-30mg, be dissolved in the 1-5ml organic solvent, and under 100HZ ultrasonic 2-8 minute, mixed liquor formed;
(2) deionized water of weighing 1-30ml, add surfactant, and mixing speed is 40-80r/min; At 25 ℃ of-65 ℃ of temperature, drip mixed liquor so that dripping of 0.001-0.1ml/s is fast in deionized water; After dropwising, reduce rotating speed, continue to stir 90-240min.
2. the preparation method of resveratrol nanometer formulation according to claim 1, is characterized in that, described in step (1), polyethyleneglycol derivative is HOOC-PEG-COOH, MPEG-OH, H
3N-PEG-NH
3, H-[OCHCH
3CO]
nAny one in-OH.
3. the preparation method of resveratrol nanometer formulation according to claim 1, is characterized in that, organic solvent described in step (1) is any one in methanol, acetone, ether, ethanol.
4. the preparation method of resveratrol nanometer formulation according to claim 1, is characterized in that, step adds surfactant by mass volume ratio in (2) at 1: 5000.
5. the preparation method of resveratrol nanometer formulation according to claim 1, is characterized in that, surfactant described in step (2) is any one in SE-10, TWEEN20, NP-6 (OP-6), PEG-200.
6. the preparation method of resveratrol nanometer formulation according to claim 1, is characterized in that, the mass volume ratio of described resveratrol, polyethyleneglycol derivative and deionized water is 1: 1: 1-3: 2: 2.
7. the preparation method of resveratrol nanometer formulation according to claim 1, is characterized in that, described in step (2), rotating speed is 0.001-0.1ml/s.
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Cited By (5)
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|---|---|---|---|---|
| CN103690487A (en) * | 2013-12-17 | 2014-04-02 | 武汉工程大学 | Carrier-free micro-nano resveratrol medicament and preparation and application thereof |
| CN103734742A (en) * | 2014-01-24 | 2014-04-23 | 上海理工大学 | Polyphenols-hordein nanoparticle and preparation method thereof |
| CN106924270A (en) * | 2017-03-10 | 2017-07-07 | 中山万汉制药有限公司 | A kind of pharmaceutical composition with weight losing function containing orlistat |
| CN107496181A (en) * | 2017-10-20 | 2017-12-22 | 上海家化联合股份有限公司 | Solubilizing systems containing resveratrol |
| CN108219091A (en) * | 2018-01-11 | 2018-06-29 | 吉林大学 | It is a kind of to increase the method and the resin nano ball of solubility in resveratrol water by preparing resveratrol/formaldehyde resin nanosphere |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103690487A (en) * | 2013-12-17 | 2014-04-02 | 武汉工程大学 | Carrier-free micro-nano resveratrol medicament and preparation and application thereof |
| CN103734742A (en) * | 2014-01-24 | 2014-04-23 | 上海理工大学 | Polyphenols-hordein nanoparticle and preparation method thereof |
| CN106924270A (en) * | 2017-03-10 | 2017-07-07 | 中山万汉制药有限公司 | A kind of pharmaceutical composition with weight losing function containing orlistat |
| CN107496181A (en) * | 2017-10-20 | 2017-12-22 | 上海家化联合股份有限公司 | Solubilizing systems containing resveratrol |
| CN108219091A (en) * | 2018-01-11 | 2018-06-29 | 吉林大学 | It is a kind of to increase the method and the resin nano ball of solubility in resveratrol water by preparing resveratrol/formaldehyde resin nanosphere |
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