CN1438225A - Ginger-yellow pigment metal-ion complex, its preparation method and use - Google Patents
Ginger-yellow pigment metal-ion complex, its preparation method and use Download PDFInfo
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- CN1438225A CN1438225A CN 03113973 CN03113973A CN1438225A CN 1438225 A CN1438225 A CN 1438225A CN 03113973 CN03113973 CN 03113973 CN 03113973 A CN03113973 A CN 03113973A CN 1438225 A CN1438225 A CN 1438225A
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Abstract
The invention discloses a turmeric pigment-metal ion complex made by reaction of turmeric pigment and metal salt in any one or mixed solvent of alcohol solvent and acetone. It also discloses the making method and the application of making drugs to cure tumor or hepatitis. It can largely improve the water-solubility and stability of the turmeric pigment and be made into many solvents such as oral preparation and injection, etc.
Description
Affiliated technical field
The present invention relates to a kind of turmeric yellow metal ion match, the invention still further relates to the preparation method and the purposes of described turmeric yellow metal ion match simultaneously.
Background technology
Turmeric yellow is to extract a kind of natural pigment that obtains from Chinese medicine turmeric, root tuber of aromatic turmeric, curcuma zedoary etc., mainly contain curcumine (Curcumin), demethoxycurcumin (demethoxycurcumin), three kinds of compositions of bisdemethoxycurcumin (bisdemethoxycurcumin), widespread use in food, makeup, medicine.A large amount of pharmacological researches show, turmeric yellow has lipopenicillinase, anti-cancer and cancer-preventing, cholagogic, anti-inflammatory, anti-radiation, multiple pharmacological effect such as anti-oxidant, antibiotic.Because turmeric yellow and ingredient curcumine thereof, demethoxycurcumin, bisdemethoxycurcumin are fat-soluble cpds, very little, the poor stability of solubleness in water, aspect medicinal, oral preparations and external preparation are only arranged, do not have still at present that water-soluble height, good stability, onset are rapid, the turmeric yellow of high bioavailability and preparation thereof injection particularly, limited turmeric yellow further application clinically.
Summary of the invention
The purpose of this invention is to provide a kind of turmeric yellow metal ion match with anticancer antihepatitic activity, its water-soluble height, good stability, clinical effectiveness is rapid, bioavailability is high.
Another object of the present invention provides the preparation method of above-mentioned turmeric yellow metal ion match, and this method technological process is simple, and product yield is big.
The present invention also aims to provide the application of this turmeric yellow metal ion match in the medicine for preparing anticancer and treatment hepatitis, the particularly application in medicines such as preparation treatment leukemia, liver cancer, cancer of the stomach, hepatitis B.
Turmeric yellow metal ion match provided by the invention is reacted in any one or two kinds of mixed solvents in alcoholic solvent, acetone by turmeric yellow and metal-salt and to make.
The preparation method of turmeric yellow metal ion match provided by the invention may further comprise the steps:
(1) with any one or two kinds of mixed solvents dissolving turmeric yellows in the alcoholic solvent, acetone, be heated to 40～50 ℃ and be incubated 1～2 hour, obtain turmeric yellow solution;
(2) add in the above-mentioned turmeric yellow solution after metal-salt being dissolved in alcohol solution, mixing, insulation reaction with basic solution adjust pH to 7～10, left standstill after 2～4 hours, and the leaching precipitation washes with water earlier, uses methanol wash again, must precipitate;
(3) step (2) is obtained be deposited in 60～90 ℃ down dry, promptly make turmeric yellow metal ion match of the present invention.
Turmeric yellow of the present invention is one or more in curcumine, demethoxycurcumin, the bisdemethoxycurcumin; Described alcoholic solvent is methyl alcohol, ethanol or both mixtures; Described metal-salt is basic metal, alkaline-earth metal or transition metal salt, is preferably calcium chloride, Repone K, zinc chloride, cupric chloride or cobalt chloride, and the weight ratio of metal-salt and turmeric yellow is 1: 2～10; Described basic solution is ammoniacal liquor or sodium hydroxide solution.
Turmeric yellow or curcumine, demethoxycurcumin, bisdemethoxycurcumin can extract from Chinese medicine turmeric, root tuber of aromatic turmeric, curcuma zedoary and obtain, and also can synthesize or obtain with other method.The turmeric yellow that the present invention uses is pressed powder, and wherein turmeric yellow content is higher than 90%.
Turmeric yellow metal ion match of the present invention is applied in treatment cancer and hepatitis aspect, can be mixed with medicament with one or more pharmaceutically acceptable carriers (pharmaceutical excipient).
Above-mentioned pharmaceutically acceptable carrier (pharmaceutical excipient) is meant the pharmaceutical excipient of pharmaceutical field routine, for example: thinner, vehicle and water etc., weighting agent such as starch, dextrin, sucrose, N.F,USP MANNITOL, lactose, Microcrystalline Cellulose etc.; Tackiness agent such as derivatived cellulose, alginate, gelatin and polyvinylpyrrolidone; Wetting agent such as glycerine; Disintegrating agent such as methyl starch sodium, hydroxypropylcellulose, cross-linked carboxymethyl cellulose, agar, lime carbonate and sodium bicarbonate; Absorption enhancer such as quaternary ammonium compound; Tensio-active agent such as cetyl alcohol, tween 80, sodium lauryl sulphate; Absorption carrier such as kaolin and soap clay; Lubricant such as talcum powder, calcium stearate and magnesium, micropowder silica gel and polyoxyethylene glycol etc.In medicament, can also contain other assistant agent such as flavouring agent, sweeting agent etc. in addition.
Turmeric yellow metal ion match medicament of the present invention can be applied to the patient by the mode of oral, rectum or administered parenterally.Be used for when oral, can be made into conventional solid preparation such as tablet, capsule, pulvis, granule etc., make liquid preparation such as water or oil-suspending agent or other liquid preparation such as syrup, mixture, elixir etc.; When being used for administered parenterally, can be made into solution, powder pin, water or the oiliness suspension agent etc. of injection.The preferred form of the present invention is powder pin, injection liquid and tablet, coated tablet, capsule, granule, mixture.
Turmeric yellow metal ion match medicament of the present invention can be according to the conventional production method preparation of pharmaceutical field.This turmeric yellow metal ion match is mixed with one or more pharmaceutical excipients, be made into required formulation then.
Turmeric yellow metal ion match of the present invention has the good curing effect to cancers such as leukemia, liver cancer, cancer of the stomach and hepatitis; Simultaneously because the water-soluble increase of turmeric yellow metal ion match, not only be suitable for preparing various formulations such as onset is rapid, bioavailability is high injection, and water miscible increase itself also promoted the medicine absorption in vivo, thereby curative effect is increased, and bioavailability improves.
The usage quantity of turmeric yellow metal ion match of the present invention and medicament thereof can be according to variations such as the type of route of administration, patient age, body weight, the disease of being treated and severity, it can be 1～500mg/kg body weight that its per daily dose calculates with the turmeric yellow metal ion match, preferred 2～450mg/kg body weight.Can use by one or many.
Turmeric yellow metal ion match of the present invention and medicament thereof are applied to treat cancer and hepatitis, and anticancer and antihepatitic activity is definite, rapid-action, effect is better than turmeric yellow, has no adverse reaction.
The present invention is further illustrated below by embodiment.
Embodiment 1
The preparation of turmeric yellow calcium composition
Get turmeric yellow 20g, with the dissolving of 1000ml ethanol acetone (volume ratio 4: 1) mixing solutions, insulation 2h is standby down in 40～50 ℃.Other takes by weighing Calcium Chloride Powder Anhydrous 5g, is dissolved in the 100ml ethanol standby; The calcium chloride ethanolic soln is added in the turmeric yellow mixing solutions, and insulation reaction 2～3h regulates above-mentioned solution PH to 7～8, standing over night with ammoniacal liquor; Filtering separation turmeric yellow calcium composition precipitation, dry under 70～80 ℃ after washing with alcohol, promptly make turmeric yellow calcium composition of the present invention.
Embodiment 2
The preparation of turmeric yellow copper complex
Get turmeric yellow 25g, with the dissolving of 1000ml ethanol acetone (volume ratio 3: 1) mixing solutions, insulation 4h is standby down in 50 ℃.Other takes by weighing cupric chloride 6g, is dissolved in the 150ml ethanol standby; The cupric chloride ethanolic soln is added in the turmeric yellow mixing solutions, and insulation reaction 4h regulates above-mentioned solution PH to 8 with ammoniacal liquor, leaves standstill 24h; Filtering separation turmeric yellow copper complex precipitation, dry under 70～80 ℃ after washing with alcohol, promptly make turmeric yellow copper complex of the present invention.
Embodiment 3
The preparation of turmeric yellow calcium composition powder injection
Turmeric yellow calcium composition 100g
N.F,USP MANNITOL 100g
PVPk30 20g
Meglumine 30g
Water for injection adds to 5000ml
Get meglumine, N.F,USP MANNITOL, PVPK30, add injection water 4500ml, the heated and stirred dissolving continues to heat.When temperature rises to 65 ℃, add the turmeric yellow calcium composition, insulation is stirred, until whole dissolvings.Be cooled to room temperature, transfer pH to 8.0, adjust volume, use 0.65 μ m and 0.22 μ m filtering with microporous membrane respectively, get clear and bright filtrate to 5000ml with 10% citric acid.Under aseptic condition, can is (5ml/ bottle) in sterilized 7ml cillin bottle, lyophilize, and freeze-drying finishes back tamponade, gland, promptly gets 1000 bottles of turmeric yellow calcium composition lyophilized injectable powders of the present invention.
Embodiment 4
The preparation of turmeric yellow calcium composition injection liquid liquid
Turmeric yellow calcium composition 50g
Tween-80 2ml
Sodium bisulfite 3g
Water for injection adds to 1000ml
Get turmeric yellow calcium composition and sodium bisulfite, add injection water 700ml and make dissolving, transfer pH6～8 with 10% sodium hydroxide, use the ultra-filtration membrane ultrafiltration, filtrate is added water for injection to 1000ml, transfer pH to 6～8 again, add tween-80, filter embedding with 0.22 μ m microporous membrane, circulation vapor sterilization 45min, promptly.
Embodiment 5
The preparation of turmeric yellow calcium composition capsule
Turmeric yellow calcium composition 50g
Dextrin 210g
Xylo-Mucine 30g
Magnesium Stearate 10g
Get turmeric yellow calcium composition, dextrin, Xylo-Mucine, Magnesium Stearate and mix, cross 80 mesh sieves,,, irritate in capsule, promptly with whole of 60 mesh sieves with dry granulation mechanism grain.
Above embodiment is only for the present invention is further illustrated, and scope of the present invention is not subjected to the restriction of illustrated embodiment.
The present invention is to provide a kind of novel treatment cancer and the medicine of hepatitis---turmeric yellow metal complexes and medicament thereof, for proving its anticancer effect, the turmeric yellow calcium composition (hereinafter to be referred as JHC) for preparing by the method that provides in the foregoing description 1 is provided the inventor, carried out pharmacodynamics test, the research situation is as follows:
JHC antitumor action 1. materials and method: 1.1 medicine JHC; Cyclophosphamide Injection, Zhejiang Haizheng Pharmaceutical Co company limited, lot number 990606; 1.2 mainly test agent bromination dimethylthiazole tetrazole (MTT), RPMI1640, U.S. Qmresco company product, DMSO, homemade analytical pure, calf serum, Hangzhou folium ilicis chinensis bio-engineering corporation product.1.3 cell strain HL
60Cell is available from Inst. of Hematology, Chinese Academy of Medical Sciences; The tumour cell that human large intestine cancer LoVo goes down to posterity in this laboratory and cultivates.1.4 the animal Kunming mouse is provided by No.1 Military Medical Univ.'s Experimental Animal Center, the DBA/2 mouse is provided by Institute of Experimental Animals, Chinese Academy of Medical Sciences.2. 2.1 couples of HL of test method and result
60The effect of cell strain
The HL60 cell cultures of exponential phase of growth is in the RPMI-1640 that contains 10% calf serum.Get above-mentioned cell during experiment, it is diluted to 2 ~ 3 * 10
4Cell/ml is inoculated in 96 well culture plates with 8 application of sample rifles under the magnetic agitation condition, and every hole 190 μ l place 37 ℃, 5%CO
2In the incubator, after cultivation 24h treated cell attachment, each hole of experimental group added the JHC solution of 10 μ l different concns respectively, every dosage group 8 holes; The concentration of Western medicine positive control medicine group Cy is 10 μ g/ml, Western medicine positive control medicine 8 holes; Physiological saline control wells 8 holes are established in every batch of experiment simultaneously.After cultivating 48h, it is 5mg/mL MTT 20 μ l that every hole adds concentration, continue to cultivate 4h, discard substratum then, add 150 μ l DMSO and fully dissolve 10min, 8 application of sample rifles pipette DMSO solution and are added in another brand-new well plates, press mtt assay is measured each hole of 570nm in microplate reader optical density(OD) (A) value, and inhibiting rate is calculated as follows:
Inhibiting rate (%)=(1-dosing hole average A value/control wells average A value) * 100%
Half-inhibition concentration (the IC of medicine
50) press the calculating of Logit method with CBAS pharmacology software.
1 visible JHC has obvious restraining effect to the HL60 cell by following table, and the inhibiting rate between 2.40-10.0 μ g/ml is respectively 26.6-93.7%, to the IC of HL60
50Be 3.54 μ g/ml.
Table 1:JHC is to HL
60The cell inhibiting effect
JHC (μ g/ml) log10 dose (X) N A value inhibiting rate (%)
10.0 1.000 8 0.192±0.009 83.7
7.0 0.845 8 0.234±0.017 79.4
4.9 0.690 8 0.212±0.060 82.0
3.43 0.533 8 0.500±0.070 57.6
2.40 0.380 8 0.866±0.096 26.6
Cy(15μg/ml) 1 8 0.101±0.020 91.4
Solvent/8 1.180 ± 0.508 0.00
Regression equation: LOG (I/ (100-I))=0.1038+0.0089*Log (D)
Relation conefficient: r=0.883 IC
50=3.54 μ g/ml
2.2JHC cytotoxicity to people's cancer of the stomach SGC-7901 cell of vitro culture
The SGC-7901 cell cultures of exponential phase of growth is diluted to 4～5 * 10 with it in the RPMI-1640 that contains 10% calf serum
3Cell/mL is inoculated in 96 well culture plates with 8 application of sample rifles under the magnetic agitation condition, and every hole 190 μ L place 37 ℃, 5%CO
2In the incubator, after cultivation 24h treated cell attachment, it was the JHC normal saline solution of 1.8 μ g/mL that each hole of experimental group adds 10 μ L concentration respectively; The concentration of positive control medicine group Cy is 15 μ g/mL; The physiological saline control wells is established in every batch of experiment simultaneously.After each organizes administration, respectively after continuing to cultivate 24h, JHC, Cy positive control and solvent control group are respectively got 8 holes, it is 5mg/mL MTT 20 μ L that every hole adds concentration, continues to cultivate 4h, discards substratum then, add 150 μ L DMSO and fully dissolve 10min, 8 application of sample rifles pipette DMSO solution and are added in another brand-new well plates, press mtt assay is measured each hole of 570nm in microplate reader optical density(OD) (A) value, and inhibiting rate is calculated as follows:
Inhibiting rate (%)=(1-dosing hole average A value/control wells average A value) * 100%
1 visible JHC has obvious restraining effect to the SGC-7901 cell by following table, and the inhibiting rate between 2.40-10.0 μ g/ml is respectively 26.6-93.7%, to the IC of SGC-7901
50Be 1.45 μ g/ml.
Table 2 JHC is to the effect of human large intestine cancer Lovo cell inhibiting
JHC log10 dose N OD value is killed and wounded percentage
(μg/ml) (X) (％)
10.0 1.000 8 0.206±0.017 75.3
7.0 0.845 8 0.229±0.018 72.5
4.9 0.690 8 0.284±0.027 65.9
3.43 0.533 8 0.429±0.025 48.6
2.40 0.380 8 0.685±0.040 17.9
Cy(15.0μg/ml) 1 8 0.016±0.008 98.1
Solvent control/8 0.834 ± 0.250 0.00
Regression equation: LOG (I/ (100-I))=0.1536+0.0096*Log (D)
Relation conefficient: r=0.924 IC
50=1.45 μ g/ml
2.3.JHC inhibition test to lotus H22 liver cancer mouse
Aseptic the go down to posterity H22 rat liver cancer cell of 5～7d of intraperitoneal of getting shakes all with the physiological saline dilution vibration of 37 ℃ of preheatings, and transfers cell count 3 * 10
7/ ml, it is subcutaneous to be inoculated in kunming mice right upper extremity armpit, every mouse subcutaneous injection 0.2ml.Every batch of experiment has generally been inoculated in 0.5h.Behind the mouse inoculation tumour 24h, be divided into model group, JHC80,40,20 at random, mg/kg group, endoxan 50mg/kg group, 18～20 every group, male and female half and half.Other get 10 (male and female half and half) not the mouse of inoculated tumour as the blank group.Mouse administration, body weight record, execution, tumour is peeled off and calculate tumour inhibiting rate.
Inhibiting rate (%)=(model group knurl weight-administration group knurl is heavy) * 100%/model group knurl is heavy
Experiment repeats once.
By following table 3-1,2 as seen, twice test-results and model group relatively, JHC has the obvious suppression effect to H22 liver cancer subcutaneous transplantation mouse tumor, and is dose-effect relationship.The basic, normal, high dosage of JHC abdominal injection group is 23.5-60.4% to H22 liver cancer transplanted tumor tumour inhibiting rate.
Table 3-1.JHC is to the influence (test 1) of H22 liver cancer cell mouse subcutaneous transplanting knurl tumour inhibiting rate
Heavy (g) tumour inhibiting rate (%) of the average knurl of group dosage (mg/kg) number
Model-20 1.724 ± 0.65-
JHC low dosage (ip) 20 18 1.318 ± 0.42 23.5
Dosage among the JHC (ip) 40 17 0.911 ± 0.61
*47.2
JHC high dosage (ip) 80 19 0.682 ± 0.34
*60.4
Cyclophosphamide Injection 50 19 0.951 ± 0.54
*44.8
Compare with model group,
*P＜0.05;
*P＜0.01;
Table 3-2.JHC is to the influence (test 2) of H22 liver cancer cell mouse subcutaneous transplanting knurl tumour inhibiting rate
Heavy (g) tumour inhibiting rate (%) of the average knurl of the routine number of group dosage (mg/kg)
Model-19 1.558 ± 0.56-
JHC low dosage (ip) 20 18 1.121 ± 0.65 28.0
Dosage among the JHC (ip) 40 20 0.886 ± 0.45
*43.1
JHC high dosage (ip) 80 19 0.675 ± 0.44
*55.4
Cyclophosphamide Injection 50 18 0.810 ± 0.49
*48.0
Compare with model group,
*P＜0.05;
*P＜0.01
2.4.JHC to the influence of mouse survival time of L1210 ascitic tumor
Aseptic the go down to posterity L1210 tumour cell of 5～7d of intraperitoneal of getting shakes all with the physiological saline dilution vibration of 37 ℃ of preheatings, and transfers cell count 2.0 * 10
7/ m1 is inoculated in the kunming mice intraperitoneal, every mouse peritoneal injection 0.2ml (4 * 10
6Individual cell).Every batch of experiment has generally been inoculated in 0.5h.Behind the mouse inoculation tumour 24h, be divided into model group, JHC80,40,20 at random, mg/kg group, endoxan 50mg/kg group, 20 every group, male and female half and half.Other get 10 (male and female half and half) not the mouse of inoculated tumour as the blank group.From second day of inoculated tumour, every mouse tail vein injection is 0.1ml/10g (iv), and blank group and model group give equivalent physiological saline, and 1 time/day, totally 10 days.Mouse claims body weight every other day one time, and on the same day of not weighing, dosage is by body weight administration the day before yesterday.
Write down the dead mouse number every day, the mouse survival surpasses 30 days and calculated by 30 days.And calculate the mouse increase in life span as follows:
Mouse increase in life span=(administration group mouse on average survive fate-model group mouse on average survive fate) * 100%/model group fate of on average surviving
Experiment repeats 1 time.
Mouse peritoneal inoculation L
1210Behind the cell, model group mouse dead in the 7th～12 day mostly (see Table 6 1～3).Removing the minority mouse can survive for 20 (can survive extremely individually surpasses 30 days, surpasses 30 days and calculates by 30 days) beyond the highest heavens.Compare with model group, the JHC of each dosage and Cy all can prolong the mouse survival time.Show that JHC has good preventive and therapeutic effect to L1210.
Table 4-1.JHC is to the influence of mouse survival time of L1210 ascitic tumor (test 1)
The routine number survival time of group dosage (mg/kg) (my god) increase in life span (%)
Model-19 8.9 ± 41.2-
JHC low dosage 20 20 12.2 ± 1.9 37.1
Dosage 40 19 13.7 ± 3.7 among the JHC
*53.9
JHC high dosage 80 20 15.2 ± 4.2
*70.8
Cyclophosphamide Injection 50 18 13.5 ± 3.9
*51.7
Compare with model group,
*P＜0.05;
*P＜0.01.
Table 4-2.JHC is to the influence of mouse survival time of L1210 ascitic tumor (test 2)
Heavy (g) tumour inhibiting rate (%) of the average knurl of the routine number of group dosage (mg/kg)
Model-20 9.4+1.6-
JHC low dosage 20 18 12.8 ± 2.2
*36.2
Dosage 40 19 14.2 ± 4.0 among the JHC
*43.6
JHC high dosage 80 20 15.8 ± 4.7
*61.2
Cyclophosphamide Injection 50 20 14.4 ± 3.9
*53.2
Compare with model group,
*P＜0.05;
*P＜0.01.
Conclusion: by observing external influence to leukemia HL60 cell and cancer of the stomach SGC-7901 cell, the result shows that JHC can obviously suppress the growth of HL60 and SGC-7901, and IC50 is respectively 3.54 μ g/ml and 1.45 μ g/ml.By observing in the body the influence of SGC-7901 and leukemia L1210, the result shows that JHC has obvious restraining effect to these two kinds of tumours.
Claims (9)
1, a kind of turmeric yellow metal ion match is characterized in that by turmeric yellow and metal-salt reacting in any one or two kinds of mixed solvents in alcoholic solvent, acetone and makes.
2, turmeric yellow metal ion match according to claim 1 is characterized in that described turmeric yellow is one or more in curcumine, demethoxycurcumin, the bisdemethoxycurcumin.
3, turmeric yellow metal ion match according to claim 1 is characterized in that described alcoholic solvent is methyl alcohol, ethanol or both mixtures.
4, turmeric yellow metal ion match according to claim 1 is characterized in that described metal-salt is basic metal, alkaline-earth metal or transition metal salt.
5, turmeric yellow metal ion match according to claim 4 is characterized in that described metal-salt is calcium chloride, Repone K, zinc chloride, cupric chloride or cobalt chloride.
6, the preparation method of the described turmeric yellow metal ion match of claim 1 may further comprise the steps:
(1) with any one or two kinds of mixed solvents dissolving turmeric yellows in the alcoholic solvent, acetone, be heated to 40～50 ℃ and be incubated 1～2 hour, obtain turmeric yellow solution;
(2) add in the above-mentioned turmeric yellow solution after metal-salt being dissolved in alcohol solution, mixing, insulation reaction with basic solution adjust pH to 7～10, left standstill after 2～4 hours, and the leaching precipitation washes with water earlier, uses methanol wash again, must precipitate;
(3) step (2) is obtained be deposited in 60～90 ℃ down dry, promptly make turmeric yellow metal ion match of the present invention.
7, the preparation method of turmeric yellow metal ion match according to claim 6, the weight ratio that it is characterized in that metal-salt and turmeric yellow is 1: 2～10.
8, the preparation method of turmeric yellow metal ion match according to claim 6 is characterized in that the described basic solution of step (2) is ammoniacal liquor or sodium hydroxide solution.
9, the application of the described turmeric yellow metal ion match of claim 1 in preparation treatment tumour or hepatitis medicament.
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|---|---|---|---|---|
| CN101205234B (en) * | 2007-12-14 | 2010-12-29 | 中山大学 | Curcumin-zinc compound as well as solid dispersion preparation and uses thereof |
| CN103054006A (en) * | 2012-12-25 | 2013-04-24 | 上海染料研究所有限公司 | Preparation method of high concentration water-solubility curcumine |
| CN103319508A (en) * | 2013-07-09 | 2013-09-25 | 长春市力诚必成新药科技开发有限责任公司 | Cellular structural supramolecular compound with drug molecule serving as ligand and preparation method of cellular structural supramolecular compound |
| CN105315143A (en) * | 2015-10-16 | 2016-02-10 | 苏州大学 | Method for improving water solubility of curcumin and solution photostability |
| WO2016044297A3 (en) * | 2014-09-15 | 2016-05-12 | Vizuri Health Sciences Llc | Polyphenol/flavonoid compositions and methods of formulating oral hygienic products |
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2003
- 2003-03-21 CN CN 03113973 patent/CN1438225A/en active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101205234B (en) * | 2007-12-14 | 2010-12-29 | 中山大学 | Curcumin-zinc compound as well as solid dispersion preparation and uses thereof |
| CN103054006A (en) * | 2012-12-25 | 2013-04-24 | 上海染料研究所有限公司 | Preparation method of high concentration water-solubility curcumine |
| CN103319508B (en) * | 2013-07-09 | 2016-06-08 | 长春市力诚必成新药科技开发有限责任公司 | A kind of be part with drug molecule microcellular structure super molecular compound and preparation method thereof |
| CN103319508A (en) * | 2013-07-09 | 2013-09-25 | 长春市力诚必成新药科技开发有限责任公司 | Cellular structural supramolecular compound with drug molecule serving as ligand and preparation method of cellular structural supramolecular compound |
| WO2016044297A3 (en) * | 2014-09-15 | 2016-05-12 | Vizuri Health Sciences Llc | Polyphenol/flavonoid compositions and methods of formulating oral hygienic products |
| CN105315143B (en) * | 2015-10-16 | 2017-06-16 | 苏州大学 | A kind of method for improving curcumin water solubility and solution photostability |
| CN105315143A (en) * | 2015-10-16 | 2016-02-10 | 苏州大学 | Method for improving water solubility of curcumin and solution photostability |
| WO2017103946A2 (en) | 2015-12-16 | 2017-06-22 | Parachur Vivek Anand | Tri-molecular complex of natural compounds |
| WO2017103946A3 (en) * | 2015-12-16 | 2017-07-27 | Parachur Vivek Anand | Tri-molecular complex of natural compounds |
| CN108366974A (en) * | 2015-12-16 | 2018-08-03 | 维韦克·阿南德·帕拉库尔 | Trimolecular complexes of natural compounds |
| JP2018537456A (en) * | 2015-12-16 | 2018-12-20 | アナンド パラチュル，ヴィヴェク | Trimolecular complex of natural compounds |
| AU2016373576B2 (en) * | 2015-12-16 | 2022-06-02 | Vivek Anand PARACHUR | Tri-molecular complex of natural compounds |
| US11696900B2 (en) | 2015-12-16 | 2023-07-11 | Olene Life Sciences Private Limited | Tri-molecular complex of natural compounds |
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