CN1985802A - Cnidiadin emulsion and its preparing method and application - Google Patents
Cnidiadin emulsion and its preparing method and application Download PDFInfo
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- CN1985802A CN1985802A CNA2006101242126A CN200610124212A CN1985802A CN 1985802 A CN1985802 A CN 1985802A CN A2006101242126 A CNA2006101242126 A CN A2006101242126A CN 200610124212 A CN200610124212 A CN 200610124212A CN 1985802 A CN1985802 A CN 1985802A
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- emulsion
- cnidiadin
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- osthole
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Abstract
The present invention discloses a kind of cnidiadin emulsion, and features that the cnidiadin emulsion is one kind of oil-in-water emulsion containing cnidiadin 0.6-10 wt%, emulsifier 0.5-15 wt%, co-emulsifier 0.01-1.0 wt%, oil phase dispersing medium 10-30 wt%, osmotic regulator 1-3 wt% and water for the rest. The cnidiadin emulsion may be prepared in different processes without using organic solvent, and contains cnidiadin of 6-100 mg/ml. It has great medicine carrying amount, no side effect of organic solvent and high medicine stability, and may be further prepared into different preparations for treating malignant tumor.
Description
Technical field
The present invention relates to the pharmaceutical product field, be specifically related to a kind ofly contain five-membered ring, only the preparation of an oxygen atom as the heterocyclic compound of ring hetero atom, particularly a kind of Emulsion arranged.
Background technology
Osthole (Osthol) has another name called osthole, and its chemistry 7-methoxyl group-8 isopentenyl coumadin by name is a kind of coumarin kind compound that at first extracts from samphire.Its structural formula is:
Studies show that, the osthole pharmacologically active is extensive, have effects such as raise immunity, osteoporosis, antiviral, mutation, the effect of plan phytoestrogen sample, antimutagenic, antitumor, particularly its powerful anti-tumor activity points out this chemical compound having broad prospects aspect the clinical treatment of malignant tumor, thereby is subjected to the common concern of this area.
State Intellectual Property Office discloses an application for a patent for invention on January 12nd, 2005 and " has extracted the technology and the pharmaceutical preparation thereof of total coumarins and monomer component from Fructus Cnidii " (application number 200410010743.3), and this application discloses the method that osthole is prepared into various preparations; Disclosed an application for a patent for invention " high purity cnidicin and preparation method thereof and be the drug regimen of active component with this chemical compound " (application number 200510014590.4) on January 25th, 2006, it is the preparation of drug combination method of active component with the osthole that this application discloses.Because osthole is fat-soluble strong, water-soluble hardly, disclosed osthole preparation of above-mentioned application or pharmaceutical composition, it all is the adjuvant preparation with the oleaginous base, the medicine drug loading of its preparation is lower, also is not easy to be absorbed by the body, and makes the drug effect of osthole be not in full use.
Summary of the invention
The technical problem to be solved in the present invention is to improve dissolubility and the stability of osthole in preparation, and then improves the drug loading and the drug targeting of its preparation.
The technical scheme that the present invention solves the problems of the technologies described above is:
A kind of Cnidiadin emulsion, this Emulsion is a kind of oil-in-water emulsion, contains mass percent and be 0.6～10% osthole, 0.5～15% emulsifying agent, 0.01～1.0% co-emulsifier, 10～30% oil phase disperse medium, 1～3% osmotic pressure regulator, all the other are water.
Described emulsifying agent can be the compound emulsifying agent of one or more combination in any in arabic gum, gelatin, cholesterol, tragcanth, tween, span, peregal, nonyl phenol polyethenoxy ether, sucrose fatty acid ester, tristerin, glyceryl monostearate, sodium lauryl sulphate, methylcellulose, Kaolin, magnesium stearate, the glycerol tristearate; Described emulsifying agent can also be natural phospholipid, natural phospholipid hydride or synthetic phospholipid.
Described co-emulsifier can be enuatrol, oleic acid, propylene glycol, PEG or PVP.
Described osmotic pressure regulator can be a glycerol.
Described pH value regulator can be sodium hydroxide, phosphoric acid, potassium dihydrogen phosphate or sodium dihydrogen phosphate.
Described oil phase disperse medium can be vegetable oil such as soybean oil, olive oil, safflower oil, Semen Maydis oil or medium chain triglycerides, can also be the triglyceride of ethanol, liquid paraffin or synthetic.
Above-mentioned emulsifying agent and oil phase disperse medium are the kinds that preparation Emulsion of the present invention can be selected, but because different dosage forms has different requirements to emulsifying agent with the oil phase disperse medium, those skilled in the art can be selected according to prepared dosage form, as be prepared into injectable emulsion, optional vegetable oil of oil phase dispersate or ethanol.
Cnidiadin emulsion of the present invention can be common breast, submicron emulsion or emulsion, wherein:
The preparation method of the common breast of described osthole is:
Emulsifying agent, the co-emulsifier of getting formula ratio join in the suitable quantity of water, stir, and form water, and the osthole of getting formula ratio is dissolved in the oil phase disperse medium and forms oil phase; Oil phase is added dropwise to aqueous phase, and the dropping process constantly stirs, and adding entry to osthole concentration at last is 6～100mg/ml.
The preparation method of described osthole submicron emulsion is:
Co-emulsifier, osmotic pressure regulator and the water of formula ratio are stirred into uniform mixture, form water.Osthole and 0.5～15% phospholipid emulsifying agent, 10-30% oil phase disperse medium form oil phase under nitrogen current (0.1-2MPa) protection; be heated to 60 ℃; oil phase is mixed with into thick breast with water; the pH value that adds pH value regulator adjusting Emulsion is 6.0-9.0; it is up to specification to change thick breast over to the extremely newborn for several times grain that circulates in the high pressure dispersing emulsification machine; filter, adding entry to osthole concentration at last is 6～100mg/ml.
The preparation method of described osthole emulsion is:
Get 0.1～1.0% emulsifying agent, the co-emulsifier of formula ratio and water mix the formation water, get in osthole, 0.2～1.0% emulsifying agent adding oil phase disperse medium and form oil phase; Under agitation water is splashed in the oil phase, high-speed stirred gets colostrum; Other gets 0.2～1.0% emulsifying agent and water mixes the outer water of formation, and above-mentioned colostrum is under agitation slowly splashed into outer water, and up to specification to quality through high-speed stirred, adding entry to osthole concentration at last is 6～100mg/ml.
Osthole is insoluble in water, but in soybean oil, midchain oil, Fructus Canarii albi wet goods fatty oil, fine solubility is arranged, the above-mentioned fatty oil solubilized osthole of per 100 grams is up to 20～50 grams, can reach 6～100mg and the every milliliter Emulsion of Emulsion of the present invention contains osthole, the bigger range of choice is arranged aspect dosage; Emulsion of the present invention need not introduced organic solvent (as ethanol or Polyethylene Glycol) and can improve drug loading greatly and realize intravenous injection, can avoid the side effect of organic solvent simultaneously yet; Osthole belongs to lactone structure, facile hydrolysis and oxidation, be prepared into the pastille lipomul after, most of drug distribution is avoided directly contacting with water at oil phase or oil-water interfaces, this buffer action has improved medicine stability greatly.
Cnidiadin emulsion of the present invention can be used for preparing the various preparations for the treatment of malignancy disease, and as oral liquid, tablet, capsule, submicron emulsion type Cnidiadin emulsion can be used for preparing injection.
To prove the effect that the present invention has by zoopery and embodiment below.
Below the used Cnidiadin emulsion of experiment is preparation example 3 described Emulsions.
1, extracorporeal anti-tumor cell (HepG2, LOVO, MCF-7, A549, K562, SGC-7901) test:
Adopt the RPMI-1640 culture fluid, add 15% newborn calf serum (FCS, 56 ℃ of deactivation 30min), transfer pH to about 7.2 with the Hepes buffer, HepG2 (human liver cancer cell), LOVO (human colon cancer cell), MCF-7 (human breast cancer cell), A549 (human lung adenocarcinoma cell), K562 (human leukemia cell), SGC-7901 (gastric carcinoma cells) cell strain are made into the individual cells suspension respectively, at 37 ℃ of saturated humidities, 5%CO
2Cultivate in the incubator, stand-by.Take the logarithm the above various cells of trophophase respectively with after 0.25% trypsin and the 0.02%EDTA digestion, be diluted to concentration 4～5 * 10 with above-mentioned culture fluid
4/ ml is inoculated in 96 orifice plates, and every hole adds 190 μ l.Establish solvent control and blank simultaneously, each dosage is established 3 parallel holes, conventional cultivate 24h after, what add various dose is subjected to reagent thing 10 μ l, at 37 ℃ of saturated humidities, 5%CO
2After cultivating 72h in the incubator, every hole adds MTT solution (with the normal saline preparation, 0.2 μ m microporous filter membrane filters) 10 μ l (5mg/ml), behind the vibration mixing, continues to cultivate 4h in the incubator.Abandoning supernatant, every hole add 150 μ l dimethyl sulfoxide, and the micro oscillator vibration behind about 1h, is surveyed its OD value with microplate reader at 570nm wavelength place, calculates suppression ratio, asks IC
50, deduct blank during mensuration.Calculate cytotoxicity by following formula:
Cytotoxicity=(1-experimental group absorbance/matched group absorbance) * 100%.
The results are shown in Table 1.As shown in table 1, Emulsion of the present invention all has inhibitory action to kinds of tumor cells.
Table 1 medicine of the present invention is to the inhibitory action (%) of different tumor cell lines
| Group | Dosage (mg/ml) | Suppression ratio (%) | |||||
| HepG2 | LOVO | MCF-7 | A549 | K562 | SGC-7901 | ||
| Blank group | - | ||||||
| 5-FU | 0.05 | 62.14** | 62.81** | 63.25** | 62.54** | 65.41** | 65.19** |
| Cnidiadin emulsion | 0.35 | 68.23** | 67.54** | 68.06** | 71.02** | 66.74** | 70.06** |
| 0.175 | 47.41** | 43.82** | 47.87** | 48.76** | 44.84** | 48.18** | |
| 0.0875 | 29.75** | 27.71** | 26.17** | 28.54** | 32.38** | 24.61** | |
Annotate: compare * P＜0.05, * * P＜0.01 with the blank group.
2, anti-tumor in vivo effect
Get and be inoculated in about 7～10 days S180 tumor cell ascites in kunming mice abdominal cavity, aseptic condition is operation down, and according to the normal saline of cell concentration adding equivalent, (the optimum cell number is 1～2 * 10 to be mixed with tumor cell suspension
7/ ml), it is subcutaneous to be inoculated in allogeneic mice left hind liquid, male body weight 18～22g, and female 17～21g, same sex is all used in each experiment, every injected in mice 0.2ml or irritate stomach 0.3ml/10g.Oncocyte is inoculated the 2nd day, mice is weighed, and random packet, and one group of 10 mice begins to test medication, negative control solvent (ip normal saline 0.2ml/d), positive control drug (10mg fluorouracil/Kg mice body weight), successive administration 10 days.To the 11st day, animal was weighed, and cutd open the tumor of getting each treated animal, weighed, and added up the tumour inhibiting rate of each treated animal at last.Experimental result and statistical result see Table 2.As shown in table 2, Emulsion of the present invention has anti-tumor in vivo effect preferably.
The heavy suppression ratio of tumor=(it is heavy that the average tumor of average tumor weight/matched group is organized in the 1-treatment) * 100%
Table 2 medicine of the present invention heavily reaches the influence of body weight to S180 tumor-bearing mice tumor
| Group | Dosage (mg/kg) | Body weight (g) | Tumor heavy (g) | Tumour inhibiting rate (%) | |
| Before the administration | After the administration | ||||
| Blank group | - | 19.9±0.8 | 30.2±4.4 | 1.24±0.31 | - |
| The 5-Fu group | 10 | 18.6±1.0 | 31.5±2.1 | 0.23±0.13 | 81.45 |
| Cnidiadin emulsion | 0.75 | 19.1±0.6 | 31.4±5.4 | 0.63±0.21 | 49.19 |
| 1.5 | 19.8±1.1 | 30.9±2.5 | 0.49±0.16 | 60.48 | |
| 3.0 | 19.5±0.9 | 31.4±3.4 | 0.37±0.18 | 70.16 | |
The specific embodiment
Preparation example
Example 1: common newborn type
| Prescription | |||
| Osthole | 100g | Fabaceous lecithin | 12g |
| Glycerol | 25g | Peregal | 75g |
| Refining Oleum Glycines | 200g | ||
| Adding distil water is to 1000ml | |||
With fabaceous lecithin, the glycerol of recipe quantity and be preheated to 80 ℃ an amount of water for injection and mix, change over to and organize in the pulper, change with per minute 20000 and stirred 3 minutes, 3 times repeatedly,, become colostrum until the fabaceous lecithin homodisperse; (2) osthole and the peregal with recipe quantity is dissolved in the refining Oleum Glycines, is heated to 80 ℃, adds to then in the above-mentioned dispersion liquid, changes over to and organizes in the pulper, and change with per minute 20000 and stir 3min, 3 times repeatedly, until the oil phase homodisperse; (3) get above-mentioned colostrum and add the water for injection that is preheated to 80 ℃ and make and reach full dose, be transferred in the high pressure dispersing emulsification machine, homogenize 3 times promptly gets the dense breast of osthole, and particle diameter is in 1～100 mu m range, and gained Emulsion osthole content is 100mg/ml.
Example 2: submicron emulsion type
| Prescription | |||
| Osthole | 50g | Lecithin | 6g |
| Glycerol | 25g | Oleum Arachidis hypogaeae semen | 100g |
| Tween 80 | 20g | ||
| Adding distil water is to 1000ml | |||
The lecithin of recipe quantity is put into high speed organize pulper, glycerol adding and 30ml water for injection, under nitrogen current, making uniform phospholipid dispersion liquid, this dispersion liquid is changed in the two step high pressure dispersing emulsification machines, add the Oleum Arachidis hypogaeae semen that is dissolved with recipe quantity osthole and Tween 80 again, under nitrogen current, filter bottling, Zha Gai under nitrogen current with No. 4 incipient fusion glass sand hourglasses.Through 90 ℃ of preheatings,, dash 60 ℃ of hot water coolings again through 121 ℃ of sterilizations 15 minutes.Get the milky osthole submicron emulsion of particle diameter below 1 μ m, gained Emulsion osthole content is 50mg/ml.
Example 3: emulsion type
| Prescription | |||
| Osthole | 10g | Liquid paraffin | 20g |
| Glyceryl monostearate | 25g | PVP | 10g |
| Tween 80 | 20g | Gelatin | 5g |
| Adding distil water is to 1000ml | |||
Get in recipe quantity osthole, monoester acid glyceride, the Tween80 adding liquid paraffin, heating and melting is as oil phase; Get gelatin solution as water, under agitation water is splashed in the oil phase, high-speed stirred a few hours promptly get the w/o type colostrum; Monoester acid glyceride, Tween80 and PVP solution are added distilled water as outer water, the new system colostrum is under agitation slowly splashed into outer water, through a few hours high-speed stirred (20000r/min), promptly get W/O/W type osthole emulsion, particle diameter is below 50 μ m, and gained Emulsion osthole content is 10mg/ml.
Application examples
Example 1: oral liquid
Get preparation example 1 described Cnidiadin emulsion (1000ml), fill becomes 100, sterilization, and every 10ml, containing osthole in every is 1.0 grams.
Example 2: tablet
Get preparation example 1 described Cnidiadin emulsion (1000ml), get 1000g dextrin and 4000g starch mixing, add Cnidiadin emulsion then, mix homogeneously, granulate,, cross sieve No. five, mixing in 60～80 ℃ of oven dry, tabletting is made 10000 altogether, and every contains osthole 10mg.
Example 3: capsule
Get preparation example 1 described Cnidiadin emulsion (1000ml), get 1000g dextrin and 4000g starch mixing, add Cnidiadin emulsion then, mix homogeneously, granulate,, cross sieve No. seven in 60～80 ℃ of oven dry, encapsulated, make 10000 altogether, every contains osthole 10mg.
Example 4: injection
Get preparation example 2 described Cnidiadin emulsions (1000ml), be distributed into 10 bottles, every bottle of 100ml, sterilization, every bottle of Cnidiadin emulsion injection contains osthole 5.0g.
Claims (10)
1, a kind of Cnidiadin emulsion, this Emulsion is a kind of oil-in-water emulsion, contains mass percent and be 0.6～10% osthole, 0.5～15% emulsifying agent, 0.01～1.0% co-emulsifier, 10～30% oil phase disperse medium, 1～3% osmotic pressure regulator, all the other are water.
2, Cnidiadin emulsion according to claim 1 is characterized in that described emulsifying agent is the compound emulsifying agent of one or more combination in any in arabic gum, gelatin, cholesterol, tragcanth, tween, span, peregal, nonyl phenol polyethenoxy ether, sucrose fatty acid ester, tristerin, glyceryl monostearate, sodium lauryl sulphate, methylcellulose, Kaolin, magnesium stearate, the glycerol tristearate; Or natural phospholipid, natural phospholipid hydride or synthetic phospholipid.
3,, it is characterized in that described co-emulsifier is enuatrol, oleic acid, propylene glycol, PEG or PVP according to the described Cnidiadin emulsion of claim 1.
4,, it is characterized in that described osmotic pressure regulator is a glycerol according to the described Cnidiadin emulsion of claim 1.
5,, it is characterized in that described pH value regulator is sodium hydroxide, phosphoric acid, potassium dihydrogen phosphate or sodium dihydrogen phosphate according to the described Cnidiadin emulsion of claim 1.
6,, it is characterized in that described oil phase disperse medium is the triglyceride of soybean oil, olive oil, safflower oil, Semen Maydis oil, medium chain triglycerides, ethanol, liquid paraffin or synthetic according to the described Cnidiadin emulsion of claim 1.
7, the preparation method of the described Cnidiadin emulsion of one of claim 1 to 6, this method is made up of following steps: emulsifying agent, the co-emulsifier of getting formula ratio join in the suitable quantity of water, stir, form water, the osthole of getting formula ratio is dissolved in the oil phase disperse medium and forms oil phase; Oil phase is added dropwise to aqueous phase, and the dropping process constantly stirs, and adding entry to osthole concentration at last is 6～100mg/ml, obtains the plain edition Cnidiadin emulsion.
8, the preparation method of the described Cnidiadin emulsion of one of claim 1 to 6, this method is made up of following steps: co-emulsifier, osmotic pressure regulator and the water of formula ratio are stirred into uniform mixture, form water.Osthole and 0.5～15% phospholipid emulsifying agent, 10-30% oil phase disperse medium form oil phase under the protection of 0.1-2MPa nitrogen current; be heated to 60 ℃; oil phase is mixed with into thick breast with water; the pH value that adds pH value regulator adjusting Emulsion is 6.0-9.0; it is up to specification to change thick breast over to the extremely newborn for several times grain that circulates in the high pressure dispersing emulsification machine; filter, adding entry to osthole concentration at last is 6～100mg/ml, obtains submicron emulsion type Cnidiadin emulsion.
9, the preparation method of the described Cnidiadin emulsion of one of claim 1 to 6, this method is made up of following steps: get 0.1～1.0% emulsifying agent, the co-emulsifier of formula ratio and water mix the formation water, get in osthole, 0.2～1.0% emulsifying agent adding oil phase disperse medium and form oil phase; Under agitation water is splashed in the oil phase, high-speed stirred gets colostrum; Other gets 0.2～1.0% emulsifying agent and water mixes the outer water of formation, and above-mentioned colostrum is under agitation slowly splashed into outer water, and up to specification to quality through high-speed stirred, adding entry to osthole concentration at last is 6～100mg/ml, obtains emulsion type Cnidiadin emulsion.
10, the application of the described Cnidiadin emulsion of one of claim 1 to 6 in preparation treatment malignancy disease medicine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2006101242126A CN1985802A (en) | 2006-12-14 | 2006-12-14 | Cnidiadin emulsion and its preparing method and application |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2006101242126A CN1985802A (en) | 2006-12-14 | 2006-12-14 | Cnidiadin emulsion and its preparing method and application |
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| CN1985802A true CN1985802A (en) | 2007-06-27 |
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|---|---|---|---|
| CNA2006101242126A Pending CN1985802A (en) | 2006-12-14 | 2006-12-14 | Cnidiadin emulsion and its preparing method and application |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102000026A (en) * | 2010-10-25 | 2011-04-06 | 徐州医学院 | Naproxen orally-taken micro-emulsion preparation and preparation method thereof |
| CN102335131A (en) * | 2011-10-10 | 2012-02-01 | 山西仁源堂药业有限公司 | Osthole micro emulsion, osthole micro emulsion sustained-release patch and preparation method thereof |
| CN103651359A (en) * | 2013-11-26 | 2014-03-26 | 武汉天惠生物工程有限公司 | Osthole biotic pesticide |
| CN109700762A (en) * | 2018-04-27 | 2019-05-03 | 西南大学 | A kind of mixing Osthole foaming microemulsion and preparation process |
| CN115024359A (en) * | 2022-06-21 | 2022-09-09 | 武汉安慧生物科技有限公司 | Fresh-keeping composition, fresh-keeping agent, preparation method and application of fresh-keeping agent, and fresh-keeping method |
-
2006
- 2006-12-14 CN CNA2006101242126A patent/CN1985802A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102000026A (en) * | 2010-10-25 | 2011-04-06 | 徐州医学院 | Naproxen orally-taken micro-emulsion preparation and preparation method thereof |
| CN102335131A (en) * | 2011-10-10 | 2012-02-01 | 山西仁源堂药业有限公司 | Osthole micro emulsion, osthole micro emulsion sustained-release patch and preparation method thereof |
| CN103651359A (en) * | 2013-11-26 | 2014-03-26 | 武汉天惠生物工程有限公司 | Osthole biotic pesticide |
| CN103651359B (en) * | 2013-11-26 | 2015-09-23 | 武汉天惠生物工程有限公司 | Osthole biotic pesticide |
| CN109700762A (en) * | 2018-04-27 | 2019-05-03 | 西南大学 | A kind of mixing Osthole foaming microemulsion and preparation process |
| CN115024359A (en) * | 2022-06-21 | 2022-09-09 | 武汉安慧生物科技有限公司 | Fresh-keeping composition, fresh-keeping agent, preparation method and application of fresh-keeping agent, and fresh-keeping method |
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Open date: 20070627 |