CN101711740A - Method for preparing targeted curcumin nanoparticles for treating ulcerative colitis - Google Patents
Method for preparing targeted curcumin nanoparticles for treating ulcerative colitis Download PDFInfo
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Abstract
The invention discloses a prescription of targeted curcumin-polylactic acid-hydroxyacetic acid copolymer (PLGA) nanoparticles for treating ulcerative colitis and a preparation process thereof. The prescription uses the targeting characteristic of the nanoparticles to an inflammatory part to reduce a medicament administration dosage and side effect and improve treatment effect. The preparation process comprises the following steps: taking a biodegradable material PLGA as a carrier material, polyvinyl alcohol as an emulsifier and 2 to 5 percent cane sugar as a freeze-drying protective agent, adding PEG 6000 into a water phase, and preparing the curcumin-PLGA nanoparticles by an emulsion-solvent volatilization method. The prescription process is optimized by taking the grain sizes of the nanoparticles and a medicament-loading rate as indexes. The prepared nanoparticles are round or elliptic and uniform in the size, have a mean grain size of 20 to 800nm and the medicament-loading rate of 10 to 20 percent, reduce dumping effect and have obviously better treatment effect on an animal pattern than a 5-aminosalicylic acid control group.
Description
Technical field
The invention belongs to medical technical field, be specifically related to a kind of preparation method of targeted curcumin nanoparticles for treating ulcerative colitis, curcumin-PLGA nanoparticle with the preparation of the present invention preparation, particle diameter is 200～800nm, carrying drug ratio is 10%～20%, envelop rate is 50-80%, and the lyophilizing formability is good, redissolution meets medicinal requirements.
Background technology
Rhizoma Curcumae Longae is the dry rhizome of Zingiberaceae curcuma Rhizoma Curcumae Longae (Curcuma longa L.).Curcumin (curcumin) is one of main active of Rhizoma Curcumae Longae, pigment, food additive and flavoring agent have been widely used as, have antitumor, antiinflammatory, antioxidation, antibiotic, alleviate effects such as drug toxicity and blood fat reducing, and its toxicity is very low, the LD50 of mice is greater than 2g/kg.
The curcumin molecular formula is C
21H
20O
6.Curcumin is a polyphenol compound with B-diketone structure, because tautomerization is an enol-type structure, has acidity, and the pKa value of three acid protons is respectively 8.38,9.88 and 10.51.Curcumin is dissolved in methanol, ethanol, propylene glycol; Be slightly soluble in water, unstable in neutral pH, decompose generation Resina Ferulae acyl methane, ferulic acid and vanillin.
Curcumin is extensive as the use prospect of medicine, has big difficulty but himself exist many limiting factors that it is promoted the use of.The water solublity of curcumin under acid and neutrallty condition is low, the high speed decomposition under alkali condition and in organic solvent easily by light degradation.The most outstanding in multifactor to show as its dissolubility in water very little all, and dissolution rate is slow, thereby causes bioavailability poor.
PLGA is a kind of good biocompatibility, biodegradable, safety good, physicochemical property is excellent pharmaceutical macromolecular material, is used for easy-to-use material in the adjuvant of medicament slow release preparation and the human body; This material is degraded to lactic acid and the hydroxyacetic acid that has in the human body earlier after entering human body, further is degraded to carbon dioxide again and water excretes, and is harmless.PLGA degradation rate in vivo can be regulated by the content and the ordering of hydroxyacetic acid in its molecule.
Summary of the invention
The objective of the invention is to propose a kind of Nano medication of curcumin system based on the emulsion-solvent evaporation method preparation, at the water insoluble and labile defective of curcumin, by being wrapped in, curcumin makes nanoparticle in the degradable polymer, thereby improve the hydrophobic property of curcumin, prolong curcumin stop and action time in vivo, improve the bioavailability of curcumin, strengthen targeting type the ulcerative colitis position.
Retrieve Chinese patent (application number: adopt acetone or acrylic acid ester to make solvent 200610125179.9) and prepared curcumin PLGA nanoparticle, wherein carrying drug ratio is 2.68%～4.5%, envelop rate is 18%～50%, the present invention is through repetition test, adopt dichloromethane to make solvent and prepared curcumin PLGA nanoparticle, the nanoparticle carrying drug ratio that obtains is 10.0%-15.0%, envelop rate is 50-80%, carrying drug ratio and envelop rate all improve greatly, significant improvement is arranged on preparation technology, can fulfilling medicinal requirements.
And Chinese patent (application number: adopted direct cryodesiccated method 200610125179.9), we are through discovering, directly the nanoparticle that obtains of lyophilization has and is difficult to again dispersive defective, and adding 2% sucrose can well improve.
The present invention is by the following technical solutions:
The main preparation process of curcumin nanoparticles is as follows:
(1) according to the theoretical carrying drug ratio of the polymer supported curcumin nano microgranule that will prepare, curcumin and PLGA are dissolved in the organic solvent altogether, the required organic facies of preparation of must writing out a prescription, wherein curcumin and PLGA ratio are 1: 1-1: 10;
(2) prepare certain density PVA (1%-5%) aqueous solution, and, get water to wherein adding a certain amount of additives;
(3) step 1 prepared organic is added the prepared water of step 2 under the shearing force of high-speed stirred, ultrasonic behind the stirring 3min with probe type ultrasonic cell pulverization instrument, get emulsion;
(4) the prepared emulsion of step 3 is volatilized under the state that stirs organic solvent, treat organic solvent volatilization fully after, earlier with centrifugal insoluble impurity, the centrifugal collection curcumin nano of the reuse 18000rpm microgranule removed of 3000rpm.
(5) add an amount of freeze drying protectant in the product that step 4 is collected, lyophilization promptly obtains curcumin PLGA nanoparticle.
PLGA of the present invention, its molecular weight are 20000-40000 dalton, PLA: the PGA ratio is 50: 50-75: 25, and organic solvent is a dichloromethane, and volume is 1mL-10mL, and PLGA concentration is 5%-50%.
Water volume of the present invention is 10mL-100mL, and PVA concentration is 1%-5%, and additives mainly contain NaCl, PEG1000 or PEG6000, and content is 0.05%-5%.
The mixing speed that the present invention adopts is 5000rpm-20000rpm, and mixing time is 1min-10min.
The supersonic cell crusher that the present invention adopts, ultrasonic power is 200-600W, ultrasonic number of times is 60-240 time.
The freeze drying protectant that the present invention adopts is lactose or sucrose, and content is 0.5%-10%.
The degradable polymer supported curcumin nano microgranule of the present invention's preparation is spherical regular nanoparticle, good dispersion in emulsion, and the curcumin nanoparticles of the present invention's preparation has higher carrying drug ratio, is fit to the bigger medicine of this type of dosage.And prominent the releasing of medicine obtained certain improvement behind the adding additives.Nanoparticle behind the adding freeze drying protectant, lyophilizing is redissolved functional, and particle diameter and distribution there is no too big change.The pharmacokinetics data show in the rat body, are prepared into the effectively prolong half-life behind the nanoparticle.
Specific embodiment
Below the present invention is further elaborated by instantiation, and % represents the gram number of the solute that solution 100mL is contained in the following example.
Preparation embodiment 1: the preparation of curcumin PLGA nanoparticle
The prescription of table 1 curcumin PLGA nanoparticle is formed
Preparation method:
With the PLGA of above-mentioned recipe quantity and curcumin be dissolved in altogether in the dichloromethane organic facies, the PVA solution of preparation is water, pour organic facies into aqueous phase, after 15000rpm stirs 2-3min, place probe type ultrasonic cell pulverization instrument, ultrasonic 60-240 time of 400W, take out then and carry out the centrifugal 10000rpm-20000rpm of low-temperature and high-speed, collect curcumin PLGA nanoparticle (Fig. 1), again carry out lyophilization after disperseing with the sucrose solution of 2%-10%, promptly obtain curcumin PLGA nanoparticle (Fig. 2).
Preparation embodiment 2: the particle size determination of nanoparticle
Measure the particle diameter and the distribution of nanoparticle with laser particle size analyzer.The particle diameter that records is 409 ± 11nm, for effective diameter is normal distribution.
Preparation embodiment 3: the mensuration of nanoparticle carrying drug ratio
Take by weighing the lyophilized powder of nanoparticle, add amount of acetone it is dissolved, survey the content of curcumin in the 425nm place, calculate the carrying drug ratio and the envelop rate of nanoparticle.
The carrying drug ratio and the envelop rate of table 2 curcumin PLGA nanoparticle
Preparation embodiment 4: the release in vitro of nanoparticle
Precision takes by weighing nano-granule freeze-dried powder (containing freeze drying protectant) in the brown bottle of 250mL respectively; add 150mL and contain hydrochloric acid (pH value the is 1.2) solution of 0.3% Tween 80; in 37 ℃ of constant temperature vibrations; at the accurate 5mL that takes out of official hour; cross 0.8 μ m microporous filter membrane; measure the concentration of curcumin in the 425nm place, calculate release percentage ratio.Add the release medium of equal volume simultaneously.Add additives PEG6000 in order to adjustment release, half an hour is prominent releases by about 78% and is reduced to about 48%, but the carrying drug ratio of nanoparticle also is reduced to 10.67% by 15.78% simultaneously, sees accompanying drawing for details.
Preparation embodiment 5: rat pharmacokinetics experiment
Get 12 of SD male rats, between body weight 270～330g, be divided into 2 groups, press 10mgkg
-1Dosage, tail vein injection curcumin solution and curcumin nanoparticles suspensoid.After administration 3,5,10,15,30,45,60min gets blood, measures curcumin content (accompanying drawing four) in the blood plasma.
The pharmacokinetic data available of rat shows, tissue distribution taken place after being prepared into nanoparticle, and prolonged the medicine holdup time in vivo.
Preparation embodiment 6: the pharmacodynamics evaluation of curcumin nanoparticles
Kunming mouse was freely drunk 5% dextran sulfate sodium (DSS) solution 7 days, set up the acute colitis model.In the beginning administration in second day that modeling begins, the normal control group is irritated stomach with normal saline every day, and positive controls is according to 100mgkg
-1Dosage give the 5-aminosalicylic acid suspension once a day, curcumin suspension group is according to 100mgkg
-1Dosage give the curcumin suspension once a day; Curcumin nanoparticles is with high, normal, basic three dosage group (100mgkg
-1, 50mgkg
-1, 30mgkg
-1).Estimate its targeting and pharmacodynamics with the variation of stool character, disease activity index (DAI), pathology index (HI), nuclear factor (NF-κ B-p65) and the measurement result of myeloperoxidase (MPO) (MPO).
Result of implementation, nearly 2 of normal control group mice loose stool occurred in second day after administration, had 4 yellow green or light yellow loose stool or half loose stool to occur on the 3rd day, and loose stool appearred in whole mices in the 4th day, and 3 mice anus band blood are arranged, all have 3 mice anus band blood during observation at least.Administration group mice situation then takes an evident turn for the better, and wherein mostly is yellow green half loose stool, with positive controls and nanoparticle high dose group the best, has only yellow green half loose stool again, and no loose stool occurs.
The DAI value of 5-aminosalicylic acid group and nanoparticle high dose group approaches normal group, shows that the nanoparticle of 5-aminosalicylic acid and high dose is comparatively obvious to the therapeutic effect of ulcerative colitis.The HI scoring of nanoparticle high dose group is starkly lower than each group, and near normal group, positive controls is taken second place.Inflammatory factor IL-1 β mRNA in nuclear factor (NF)-the kB inhibitor curcumin the is adjustable IBD Muridae model and the expression of IL-10mRNA show that curcumin might be the targeted drug of a kind of ergastic IBD.Curcumin is prepared into after the nanoparticle, and the accumulating of inflammation part, curcumin nanoparticles has certain therapeutic effect to ulcerative colitis by nanoparticle.The rising of MPO is an important symbol of ulcerative colitis, the therapeutic effect of nanoparticle high dose group obviously is better than other administration groups, and compared significant difference (p＜0.05) with the curcumin suspension, proved that nanoparticle is accumulated in inflammation part, certain targeting has been arranged.
Description of drawings
The particle size distribution figure of accompanying drawing 1 curcumin PLGA nanoparticle
The particle size distribution figure of the curcumin PLGA nanoparticle that redissolves after accompanying drawing 2 lyophilizing
Accompanying drawing 3 adds the release in vitro figure behind the NaCl
Accompanying drawing 4 curcumin solution and curcumin PLGA nanoparticle are at the intravital blood drug level-time diagram of rat
Abscissa: time, vertical coordinate: blood drug level (ng/ml)
Accompanying drawing 5 adds the release in vitro figure behind the PEG6000
Abscissa: time, vertical coordinate: cumulative release percentage rate %.
Claims (10)
1. a ulcer is thought the preparation method of colitis targeted curcumin nanoparticles, it is characterized in that with emulsifying-solvent evaporation method preparation, and doing the drug loading that solvent obtains through the comparative optimization dichloromethane is 10%～20%.
2. curcumin nanoparticles according to claim 1 is characterized in that the PLGA molecular weight is 20000～40000 dalton, preferred 20000 dalton, and PLA: the PGA ratio is 50: 50.
3. the preparation method of the described controlled release microparticles of Nano medication of curcumin of claim 1 is characterized in that, preparation process is as follows:
Step 1, according to the theoretical drug loading of the polymer supported curcumin nano microgranule that will prepare, curcumin and PLGA are dissolved in the organic solvent altogether the required organic facies of preparation of must writing out a prescription.
Step 2, the certain density PVA aqueous solution of preparation, and, get water to wherein adding a certain amount of additives.
Step 3, step 1 prepared organic is added the prepared water of step 2 under the shearing force of high-speed stirred, stirs, ultrasonic with probe type ultrasonic cell pulverization instrument, emulsion.
Step 4, with the prepared emulsion of step 3 organic solvent that under the state that stirs, volatilizees, treat organic solvent volatilization fully after, first low-speed centrifugal is removed insoluble impurity, again the high speed centrifugation collecting precipitation.
Step 5, add an amount of freeze drying protectant in the product that step 4 is collected, lyophilization promptly obtains curcumin PLGA nanoparticle.
4. the curcumin nanoparticles described in claim 3 is characterized in that organic solvent is a dichloromethane, and volume is 1mL-10mL.
5. the curcumin nanoparticles described in claim 3 is characterized in that PLGA concentration is 5%-50%.
6. the curcumin nanoparticles described in claim 3 is characterized in that PVA concentration is 1%-5%.
7. the curcumin nanoparticles described in claim 3 is characterized in that the water volume is 10mL-100mL.
8. the curcumin nanoparticles described in claim 3 is characterized in that water adds additives with adjustment release, mainly is to reduce prominent releasing, and additives mainly contain NaCl, PEG1000 or PEG6000, and content is 0.05%-5%.
9. the curcumin nanoparticles described in claim 3 is characterized in that mixing speed is 5000rpm-20000rpm, and mixing time is 1min-10min; Ultrasonic use supersonic cell crusher, ultrasonic power is 200-600W, ultrasonic number of times is 60-240 time.
10. the curcumin nanoparticles described in claim 3 is characterized in that nanoparticle adds freeze drying protectant before lyophilizing, adds lactose or sucrose, and content is 0.5%-10%.
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Cited By (15)
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| CN102008454A (en) * | 2010-12-03 | 2011-04-13 | 上海交通大学 | Daidzein-entrapped PLGA nanoparticles and preparation method thereof |
| CN102283812A (en) * | 2010-06-17 | 2011-12-21 | 江西中医学院 | Nanoparticle preparation for treating brain diseases |
| CN102600063A (en) * | 2011-06-09 | 2012-07-25 | 天津大学 | Method for preparing curcumin micelle with high medicine loading |
| CN103054809A (en) * | 2011-12-22 | 2013-04-24 | 苏州雷纳药物研发有限公司 | Curcumin-particle-containing sustained-release microsphere with high medicament loading capacity as well as preparation method and application thereof |
| CN103446057A (en) * | 2013-09-05 | 2013-12-18 | 常州市第一人民医院 | Oral curcumin nano-granule and preparation method thereof |
| CN103768012A (en) * | 2013-12-24 | 2014-05-07 | 浙江凯胜科技有限公司 | Method for preparing curcumin lipid nano-particle suspension or nano-particles |
| CN103908444A (en) * | 2014-02-25 | 2014-07-09 | 广西医科大学 | Application of curcumin in preparation of drug used for resisting colitis |
| US8962032B2 (en) | 2009-12-17 | 2015-02-24 | The Queen's University Of Belfast | Modulator |
| CN105816883A (en) * | 2016-02-03 | 2016-08-03 | 华南师范大学 | Probiotics folic acid targeting carrier carrying anti-cancer medicament curcumin and preparation method thereof |
| CN106038512A (en) * | 2016-06-15 | 2016-10-26 | 华侨大学 | Layer-by-layer self-assembly nano-carrier and preparation method thereof |
| CN107595804A (en) * | 2017-11-03 | 2018-01-19 | 西南大学 | A kind of preparation method and applications of the new bowl-shape particle of load medicine |
| CN112245414A (en) * | 2020-10-15 | 2021-01-22 | 四川大学华西医院 | Application of curcumin or its drug-carrying system in preparation of drugs for treating penile erectile dysfunction |
| WO2022085028A1 (en) * | 2020-10-21 | 2022-04-28 | Central Council For Research In Homoeopathy | Nano curcumin homeopathic formulation for treatment of malaria |
| CN115227682A (en) * | 2022-07-25 | 2022-10-25 | 天津市医药科学研究所(天津市医药与健康研究中心) | Preparation method of powder inhalation for targeted small-airway sustained-release delivery of COPD (chronic obstructive pulmonary disease) therapeutic drug |
| CN116139089A (en) * | 2022-12-29 | 2023-05-23 | 广东医科大学 | Nanometer preparation of chitosan and nanometer traditional Chinese medicine, and preparation method and application thereof |
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Cited By (22)
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| US8962032B2 (en) | 2009-12-17 | 2015-02-24 | The Queen's University Of Belfast | Modulator |
| CN102283812B (en) * | 2010-06-17 | 2015-01-28 | 江西中医学院 | Nanoparticle preparation for treating brain diseases |
| CN102283812A (en) * | 2010-06-17 | 2011-12-21 | 江西中医学院 | Nanoparticle preparation for treating brain diseases |
| CN102008454B (en) * | 2010-12-03 | 2012-07-04 | 上海交通大学 | Daidzein-entrapped PLGA nanoparticles and preparation method thereof |
| CN102008454A (en) * | 2010-12-03 | 2011-04-13 | 上海交通大学 | Daidzein-entrapped PLGA nanoparticles and preparation method thereof |
| CN102600063A (en) * | 2011-06-09 | 2012-07-25 | 天津大学 | Method for preparing curcumin micelle with high medicine loading |
| CN103054809A (en) * | 2011-12-22 | 2013-04-24 | 苏州雷纳药物研发有限公司 | Curcumin-particle-containing sustained-release microsphere with high medicament loading capacity as well as preparation method and application thereof |
| CN103446057A (en) * | 2013-09-05 | 2013-12-18 | 常州市第一人民医院 | Oral curcumin nano-granule and preparation method thereof |
| CN103446057B (en) * | 2013-09-05 | 2014-12-31 | 常州市第一人民医院 | Oral curcumin nano-granule and preparation method thereof |
| CN103768012A (en) * | 2013-12-24 | 2014-05-07 | 浙江凯胜科技有限公司 | Method for preparing curcumin lipid nano-particle suspension or nano-particles |
| CN103768012B (en) * | 2013-12-24 | 2016-02-03 | 浙江凯胜科技有限公司 | The preparation method of a kind of curcumin lipid nanoparticle suspension or nanoparticle |
| CN103908444A (en) * | 2014-02-25 | 2014-07-09 | 广西医科大学 | Application of curcumin in preparation of drug used for resisting colitis |
| CN105816883A (en) * | 2016-02-03 | 2016-08-03 | 华南师范大学 | Probiotics folic acid targeting carrier carrying anti-cancer medicament curcumin and preparation method thereof |
| CN105816883B (en) * | 2016-02-03 | 2018-12-14 | 华南师范大学 | A kind of probiotics folate-targeted carrier and preparation method thereof loading anticancer drug curcumin |
| CN106038512B (en) * | 2016-06-15 | 2019-06-04 | 华侨大学 | A kind of LBL self-assembly nano-carrier and preparation method thereof |
| CN106038512A (en) * | 2016-06-15 | 2016-10-26 | 华侨大学 | Layer-by-layer self-assembly nano-carrier and preparation method thereof |
| CN107595804A (en) * | 2017-11-03 | 2018-01-19 | 西南大学 | A kind of preparation method and applications of the new bowl-shape particle of load medicine |
| CN112245414A (en) * | 2020-10-15 | 2021-01-22 | 四川大学华西医院 | Application of curcumin or its drug-carrying system in preparation of drugs for treating penile erectile dysfunction |
| WO2022085028A1 (en) * | 2020-10-21 | 2022-04-28 | Central Council For Research In Homoeopathy | Nano curcumin homeopathic formulation for treatment of malaria |
| CN115227682A (en) * | 2022-07-25 | 2022-10-25 | 天津市医药科学研究所(天津市医药与健康研究中心) | Preparation method of powder inhalation for targeted small-airway sustained-release delivery of COPD (chronic obstructive pulmonary disease) therapeutic drug |
| CN115227682B (en) * | 2022-07-25 | 2023-12-22 | 天津市医药科学研究所(天津市医药与健康研究中心) | Preparation method of powder aerosol for targeted small-airway slow-release delivery of COPD (chronic obstructive pulmonary disease) therapeutic drug |
| CN116139089A (en) * | 2022-12-29 | 2023-05-23 | 广东医科大学 | Nanometer preparation of chitosan and nanometer traditional Chinese medicine, and preparation method and application thereof |
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Application publication date: 20100526 |