CN105267206A - Application of ShizukaolD in preparing medicine for inhibiting clone formation of hepatoma carcinoma cells - Google Patents
Application of ShizukaolD in preparing medicine for inhibiting clone formation of hepatoma carcinoma cells Download PDFInfo
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- CN105267206A CN105267206A CN201410315148.4A CN201410315148A CN105267206A CN 105267206 A CN105267206 A CN 105267206A CN 201410315148 A CN201410315148 A CN 201410315148A CN 105267206 A CN105267206 A CN 105267206A
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Abstract
The invention belongs to the fields of chemical industry and medicines, and relates to an application of ShizukaolD in preparing an anti-tumor medicine. The invention provides the application of ShizukaolD in preparing the anti-hepatoma medicine, wherein the anti-hepatoma medicine is the medicine for inhibiting or delaying the clone formation of the hepatoma carcinoma cells. ShizukaolD is added into a culture solution of the hepatoma carcinoma cells, so that the clone formation of the hepatoma carcinoma cells can be obviously reduced. ShizukaolD belongs to a natural product, is high in bioavailability and stable in property, and has a clinical use value. The small molecule compound provided by the invention can be developed as the novel anti-hepatoma medicine or the auxiliary component thereof, is obvious in the tumor suppression effect, and is environmentally friendly and pollution-free, and thus a novel path and means are provided for treating and curing tumour.
Description
Technical field
The invention belongs to chemical field and field of medicaments, relate to shizukaol D and preparing the application in medicines resistant to liver cancer.
Background technology
Characters of Primary Malignant Tumors of Liver originates from epithelium or the mesenchymal tissue of liver, and the former is called primary hepatocarcinoma, is that China is occurred frequently, very harmful malignant tumor.Secondary cases or title secondary liver cancer mean that the malignant tumor of the multiple organ origin of whole body is invaded to liver.Generally be more common in the hepatic metastases of the organ malignant tumours such as stomach, biliary tract, pancreas, Colon and rectum, ovary, uterus, lung, mammary gland.
Liver is the maximum parenchymatous organ of human body, bears all kinds of important metabolic function of human body, and therefore, liver is once occur that malignant tumor will cause not and the serious consequence of life.Again because liver has abundant supply of blood flow, as in close relations in postcava, portal vein, biliary system etc. with the important feature of human body; Liver malignancy incidence of occult, invasive growth is quick, its treatment very difficulty.
At present, Therapeutic Method comprises operation, hepatic artery ligation, hepatic arterial chemoembolization, radio frequency, freezing, laser, microwave and the method such as chemotherapy and radiotherapy.Biotherapeutics, traditional Chinese medical herbal treatment hepatocarcinoma also more application.The treatment of current hepatocarcinoma headed by operation, this is because the side effect of radiation and chemotherapy.Many Chemotherapeutic Drugs On Normal cells also have lethal effect, cause patient's self immune system to receive comparatively macrolesion over the course for the treatment of.The medicine phoenix feathers and unicorn horns that side effect is less, therefore finds the important topic that new candidate compound is prevention of hcc and treatment.
Herba chloranthi japonici is herb or the root and rhizome of Chloranthaceae plant Herba chloranthi japonici (ChloranthusJaponicusSieb).Sesquiterpenoids is a compounds important in Chloranthaceae plant, in whole Chloranthaceae plant, all have distribution, has antiinflammatory spasmolytic, suppresses the biological activitys such as microorganism.Obtain half its skeleton of terpenoid complex structure in Herba chloranthi japonici and can be divided into a few types such as eudesmane type, ring eudesmane-type, germacrane, acorane type, they have the various ways such as lactone, ketone, alcohol, polymer simultaneously.
Herba chloranthi japonici Herb hyoscine, has effect of damp eliminating cold expelling, promoting blood circulation and stopping pain, dissipating blood stasis removing toxic substances.Folk remedy has many records about Herba chloranthi japonici, can treat the diseases such as furuncle, scabies, innominate toxic swelling, venom, mastitis as Herba chloranthi japonici external application.
The nineteen nineties such as Kawabata have isolated 1 dimer compound be polymerized by 2 ring eucalyptus globulus type sesquiterpene lactoness first from Herba chloranthi japonici, called after Herba chloranthi japonici alcohol A (shizukaolA), be separated from Herba chloranthi japonici in 1992 and obtain 3 dimer compounds be polymerized by 2 ring eucalyptus globulus type sesquiterpene lactoness, called after shizukaol B-D (shizukaolB-D).
Application number is 200910095051.6, the applying date is 20091013, name is called the preparation method illustrating shizukaol D in the Chinese invention patent application of " onoseriolide Dimerized sesquiterpenoids; its preparation method and the application in pharmacy thereof ", and show that shizukaol D obviously can increase the consumption of L6 grape cell sugar, point out it can promote the effect of insulin, promote picked-up and the transhipment of sugar.
Shizukaol D, English ShizukaolD, CASNo.:142279-42-3 by name.Shizukaol D is natural product, and bioavailability is higher, character is more stable, has Clinical practice and is worth.That studies the chemistry and biology of this compounds along with people gos deep into, and its molecular mechanism of action will be progressively clear and definite, and this will promote modifying for chemical structure and the structure activity study of this compounds further, and contribute to the medical value improving this compounds.
Summary of the invention
The object of this invention is to provide the new pharmaceutical usage of shizukaol D.
The invention provides shizukaol D and preparing the application in medicines resistant to liver cancer, especially shizukaol D suppresses the application in the medicine of hepatoma carcinoma cell Clone formation in preparation.
Foundation in the present invention: usually, Cell colonies assay and cell inoculation survival rate, cellular activities adherent after representing inoculating cell also forms the quantity of clone; Cell after adherent is not necessarily each can breed and be formed clone, and the cell forming clone must be the adherent cell with there being proliferation activity.Cloning efficiency reflection cell colony dependency and multiplication capacity two important characters.
Medicine of the present invention makes injection or tablet.
Described tumor derives from smmc-7721, SK-hep1, HepG2, QGY, Hep3B or FOCUS cell.
In the present invention, the medicine of described suppression hepatoma carcinoma cell Clone formation can be the compositions of shizukaol D and other treatment liver-cancer medicine.Such as, described other treatment liver-cancer medicine is BAY 43-9006.
On the other hand, shizukaol D is added in the culture fluid of the tumor cell of In vitro culture, the propagation of enough obvious inhibition tumor cells and Clone formation.
Wherein, in the culture fluid of the tumor cell of In vitro culture, the drug level of the shizukaol D added is greater than 0 and is less than 50 μm of ol/L.
Generally speaking, the final concentration adding shizukaol D is 1-100 μM.Such as, 1-5 μM, 1-10 μM, 5-10 μM, 1-20 μM, 5-30 μM, 1-60 μM, 5-90 μM, 10-40 μM, 1-50 μM, 5-60 μM, 15-25 μM, 5-50 μM, 15-60 μM, 25-40 μM, 5-40 μM, etc.Preferably, the drug level of shizukaol D is less than 20 μm of ol/L.
The hepatoma carcinoma cell adopted in one embodiment of the present of invention is SMMC-7721 cell.
The hepatoma carcinoma cell adopted in another embodiment is Focus cell.
Micromolecular compound of the present invention can adopt the preparation method of various routine to prepare.Such as, the method for artificial chemistry synthesis is adopted.
For shizukaol D of the present invention, can by itself and suitable pharmaceutically acceptable carrier coupling.This kind of pharmaceutical composition contains the compound and pharmaceutically acceptable carrier or excipient for the treatment of effective dose.This kind of carrier comprises (but being not limited to): saline, buffer, glucose, water, glycerol, ethanol and combination thereof.Pharmaceutical preparation should match with administering mode.Shizukaol D of the present invention can be made into injection form, such as, be prepared by conventional method with normal saline or the aqueous solution containing glucose and other adjuvant.The pharmaceutical composition of such as Tablet and Capsula and so on, is prepared by conventional method.Pharmaceutical composition such as injection, solution, Tablet and Capsula should aseptically manufacture.The dosage of active component is treatment effective dose, such as every day about 1 microgram/kg body weight-Yue 5 mg/kg body weight.In addition, shizukaol D of the present invention also can use together with other treatment agent.
When shizukaol D of the present invention is used as medicine, the shizukaol D for the treatment of effective dose can be applied to mammal, wherein this treatment effective dose is usually at least about 10 micrograms/kg body weight, and be in most of the cases no more than about 8 mg/kg body weight, preferably this dosage is about 10 micrograms/kg body weight-Yue 1 mg/kg body weight.Certainly, concrete dosage also should consider the factor such as route of administration, patient health situation, and these are all within skilled practitioners skill.
The invention provides shizukaol D and preparing the application in antitumor drug, especially preparation suppresses the medicine of hepatoma carcinoma cell Clone formation.Tumor be exception due to cell proliferation and differentiation, Infiltration and metastasis is another feature of tumor, and experimental result growth curve of the present invention shows, shizukaol D can the propagation of inhibition tumor cell.Clone forming Test result shows, and after dosing, the negative control group clone number that tumor cell SMMC-7721 and FOCUS cell do not add shizukaol D obviously declines, and the clonality of the obvious T suppression cell of shizukaol D energy is described.Shizukaol D has the adherent of T suppression cell and multiplication capacity, and the existence reducing hepatoma carcinoma cell is active, can as the lead compound of Hepatoma therapy medicine.
Micromolecular compound shizukaol D of the present invention is natural product, tumor killing effect is obvious, can the obviously propagation of inhibition tumor cell and Clone formation, environmental protection, side effect is less, can be used as new antitumor drug or its auxiliary element is developed, for treatment with cure tumor and provide new approach and means.
Accompanying drawing explanation
Fig. 1 is focus cell clonal formation result figure,
Wherein, the final concentration of numeral and dosing in figure, unit is micro-rub (μm ol/L),
The focus cell of shizukaol D process after 48 hours, compared with the matched group of non-dosing, cell clonal formation obviously reduces.Along with the increase of drug level, number of cell clones progressively declines, and illustrates that shizukaol D suppresses FOCUS cell clonal formation to have concentration dependent.
Fig. 2 and Fig. 3 is the cell clonal formation result figure of SMMC-7721,
Wherein, the final concentration of numeral and dosing in figure, unit is micro-rub (μm ol/L).1000 SMMC-7721 cells inoculated by the every ware of Fig. 2, and 500 SMMC-7721 cells inoculated by the every ware of Fig. 3;
Compared with the matched group of non-dosing, the SMMC-7721 cell of shizukaol D process after 48 hours, Clone formation obviously reduces, and has concentration dependent.
Detailed description of the invention
The experimental technique adopted in test of the present invention:
1. cell recovery
1) from liquid nitrogen container, take out cryopreservation tube, directly drop in 37 DEG C of warm water, and shake makes it melt as early as possible frequently.
2) from 37 DEG C of water-baths, take out cryopreservation tube, with suction pipe sucking-off cell suspension, inject centrifuge tube and add more than 10 times culture fluid, low-speed centrifugal after mixing, abandons supernatant, then repeats to wash once with culture fluid.
3), after suitably diluting with culture fluid, inoculated and cultured bottle, be placed on 37 DEG C of incubator quiescent culture, next day changes culture fluid, continues to cultivate.Go down to posterity when being cultured to finite concentration.SMMC-7721 and FOCUS cell culture, containing in the DMEM high glucose medium of 10% hyclone, contains 100U/ml penicillin and 100 μ g/ml streptomycins in culture medium.
2. passage is cultivated
Every day observation of cell growth situation, when cell grow in culture bottle about 90% converge time go down to posterity, about went down to posterity once every 2-4 days.One bottle goes down to posterity into three bottles, or a 25cm
2go down to posterity in a 75cm
2culture bottle in.Method:
1) with 1 × phosphate buffer washed cell once.
2) add the digestion of 2-3ml trypsinization liquid, be placed in 37 DEG C of incubator numbers minute.Pat Tissue Culture Flask with hands, make cell separation.
3) trypsinization is stopped with the suitable culture medium of the Gibico hyclone containing 10-15%.Cell is sub-packed in new culture bottle, continues to cultivate.
3. cell cryopreservation
1) get the cell tryptase protease digestion being cultured to exponential phase, to be collected in centrifuge tube and to count, centrifugal.
2) reject trypsin and old culture fluid, add the frozen culture fluid (containing 10%DMSO, 40%DMEM and 50%Gibico hyclone) configured, in cryopreserving liquid, the ultimate density of cell is 0.5-1 × 10
7/ ml.Blowing and beating gently with suction pipe makes cell even, and be then distributed in aseptic cryopreservation tube, often pipe adds 1-1.5ml.
3) cryopreservation tube is put into freezing storing box and put-80 DEG C of quick-freezings, move in liquid nitrogen container after 5 hours and preserve.
4. medicine prepares:
Shizukaol D is dissolved in DMSO (dimethyl sulfoxide), and the mother solution being mixed with 100mM or 50mM is for subsequent use.
Shizukaol D, English ShizukaolD, CASNo.:142279-42-3 by name.
Its structural formula is as follows:
Embodiment 1MTS method measures shizukaol D to the growth inhibited effect of hepatoma carcinoma cell
HepG2 (purchased from ATCC) 3 × 10
3/ hole is seeded to 96 orifice plates, cultivate within 24 hours, make it adherent after add shizukaol D (purchased from western power Pharmaceutical), if 6 Concentraton gradient, each concentration establishes 3 multiple holes.Cell, at 37 DEG C, is cultivated after 72 hours under 5%CO2 condition, is outwelled culture fluid, measure cell survival rate with MTS test kit (Promega company).
Method of testing is: cell serum-free medium is washed one time, adds the MTS chromophoric solution (add 2ml solution 1 and 100 μ l solution 2 in 10ml serum-free medium, fully mix) prepared in advance according to the amount of 100 μ l/well.Do not have the hole of cell to be set to this bottom outlet by one, the bias light in order to calibration solution absorbs.Cell is put into cell culture incubator and continues cultivation 2 ~ 4 hours, then absorbance value (reference wavelength 630-700nm is read by microplate reader, measure wavelength 490nm), calculate cell survival rate, to measure the numerical value of hole absorbance value/control wells absorbance value as cell survival rate.According to cell survival rate, calculate shizukaol D to the IC50 value of HepG2 cell.
IC50 refers to the concentration of a suppressed half inhibitor.Here the concentration that HepG2 cell quantity is a half shizukaol D of contrast is.The calculating of IC50 generally needs the dosage effect of mensuration more than 5, then obtains function calculating by curve fitting and obtain.
Result: the IC50 value of shizukaol D to HepG2 cell is 25.40 μMs.
Use the same method test SMMC-7721 cell (purchased from Chinese Academy of Sciences's cell bank), and the IC50 value of result shizukaol D to SMMC-7721 cell is about 15.17 μMs.
Use the same method test Sk-hep1 cell (purchased from Chinese Academy of Sciences's cell bank), and the IC50 value of result shizukaol D to Sk-hep1 cell is about 11.50 μMs.
Use the same method test QGY cell (purchased from ATCC), and the IC50 value of result shizukaol D to QGY cell is about 16.10 μMs.
Use the same method test Focus cell (purchased from Chinese Academy of Sciences's cell bank), and the IC50 value of result shizukaol D to Focus cell is about 5.70 μMs.
Embodiment 2 shizukaol D is on the impact of hepatoma carcinoma cell cloning efficiency
Experimental procedure:
1, to take the logarithm each group of cell of trophophase, blow and beat into individual cells with 0.25% trypsinization respectively, and cell suspension is for subsequent use in the DMEM culture fluid of 10% hyclone.
2, cell suspension is made gradient multiple dilutions, often organize cell and inoculate respectively in the ware containing the pre-temperature culture fluid of 3.6cm diameter 37 DEG C with the Graded Density of every ware 500,1000,200 cells respectively, and rotate gently, make cell dispersal even.
3. after cell attachment, add the shizukaol D that final concentration is respectively 10.00 μMs, 5.00 μMs, 2.50 μMs, 1.25 μMs and 0.63 μM, with the DMSO of 0.01% volume ratio (containing same volume DMSO with 10.00 μMs of shizukaol Ds) for negative control.After hatching 48 hours, be changed to normal incubation medium.Put 37 DEG C, cultivate 10-14 days in the cell culture incubator of 5%CO2 and saturated humidity.
4, often observing, when there is macroscopic clone in culture dish, stopping cultivating.Abandoning supernatant, carefully embathes 2 times with PBS.Add 4% paraformaldehyde fixed cell 5mL and fix 15 minutes.Then remove fixative, add appropriate GIMSA application dyeing liquor dye 10 ~ 30 minutes, then slowly wash away dyeing liquor with flowing water, air drying.
5, plate be inverted and superpose the transparent film that is with grid, with the naked eye directly counting clone, or being greater than clone's number of 50 cells at microscope (low power lens) counting.Finally calculate cloning efficiency.
Cloning efficiency=(clone's number/inoculating cell number) × 100%.
As shown in Figure 1-Figure 3, compared with the control, after dosing, number of cell clones obviously reduces result.This illustrates that shizukaol D can suppress the adherent and Colony forming ability of FOCUS and 7721 cells.
More specifically, focus cell in shizukaol D process after 48 hours, compared with the matched group of non-dosing, cell clonal formation number obviously reduces, along with the increase of drug level, number of cell clones progressively declines, and illustrates that shizukaol D suppresses FOCUS cell clonal formation to have concentration dependent.
SMMC-7721 cell is in shizukaol D process after 48 hours, and compared with the matched group of non-dosing, cell clonal formation number obviously reduces.Along with the increase of drug level, number of cell clones declines rapidly, when drug level reaches 10 μMs, almost can't see the formation of cell clone.Every ware inoculation 500 or 1000 cells, although the final number of cell clones formed is different, along with drug level increases, number of cell clones downward trend is identical, illustrates that shizukaol D suppresses SMMC-7721 cell clonal formation to have concentration dependent.
Claims (9)
1. the shizukaol D of following structural formula suppresses the application in the medicine of hepatoma carcinoma cell Clone formation in preparation,
2. apply as claimed in claim 1, it is characterized in that, described medicine makes injection or tablet.
3. apply as claimed in claim 1, it is characterized in that, described hepatoma carcinoma cell comes from smmc-7721 cell.
4. apply as claimed in claim 1, it is characterized in that, described hepatoma carcinoma cell comes from FOCUS cell.
5. apply as claimed in claim 1, it is characterized in that, described medicine is the compositions of shizukaol D and other treatment liver-cancer medicine.
6. apply as claimed in claim 1, it is characterized in that, the compositions be made up of is added in the culture fluid of adherent hepatoma carcinoma cell of In vitro culture, suppress the Clone formation of this adherent hepatoma carcinoma cell shizukaol D and other treatment liver-cancer medicine.
7. apply as claimed in claim 1, it is characterized in that, shizukaol D is added in the culture fluid of adherent hepatoma carcinoma cell of In vitro culture, suppress the Clone formation of this adherent hepatoma carcinoma cell.
8. application as claimed in claims 6 or 7, it is characterized in that, the drug level of shizukaol D is greater than 0 and is less than 50 μm of ol/L.
9. apply as claimed in claim 8, it is characterized in that, the drug level of shizukaol D is less than 20 μm of ol/L.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101671346A (en) * | 2009-10-13 | 2010-03-17 | 中国科学院昆明植物研究所 | Lindenrane-type dimerization sesquiterpenoids, preparation method and applications thereof in pharmacy |
| CN103127062A (en) * | 2011-11-28 | 2013-06-05 | 复旦大学 | Application of 13'-acetyl silver grass alcohol C in manufacturing of antineoplastic drugs |
| CN103127061A (en) * | 2011-11-28 | 2013-06-05 | 复旦大学 | Medicine application of chloranthus japonicus alcohol M |
| CN103127063A (en) * | 2011-11-28 | 2013-06-05 | 复旦大学 | Application of chloranthus japonicus alcohol F in preparation of antitumor drugs |
| CN103127060A (en) * | 2011-11-28 | 2013-06-05 | 复旦大学 | Application of chloranthus japonicus alcohol D in preparation of antitumor drugs |
-
2014
- 2014-07-03 CN CN201410315148.4A patent/CN105267206A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101671346A (en) * | 2009-10-13 | 2010-03-17 | 中国科学院昆明植物研究所 | Lindenrane-type dimerization sesquiterpenoids, preparation method and applications thereof in pharmacy |
| CN103127062A (en) * | 2011-11-28 | 2013-06-05 | 复旦大学 | Application of 13'-acetyl silver grass alcohol C in manufacturing of antineoplastic drugs |
| CN103127061A (en) * | 2011-11-28 | 2013-06-05 | 复旦大学 | Medicine application of chloranthus japonicus alcohol M |
| CN103127063A (en) * | 2011-11-28 | 2013-06-05 | 复旦大学 | Application of chloranthus japonicus alcohol F in preparation of antitumor drugs |
| CN103127060A (en) * | 2011-11-28 | 2013-06-05 | 复旦大学 | Application of chloranthus japonicus alcohol D in preparation of antitumor drugs |
Non-Patent Citations (3)
| Title |
|---|
| RONGKUAN HU等: "Shizukaol D Isolated from Chloranthus japonicas Inhibits AMPK-Dependent Lipid Content in Hepatic Cells by Inducing Mitochondrial Dysfunction", 《PLOS ONE》 * |
| XIN-HUI RAN等: "Chloramultiols A-F, Lindenane-Type Sesquiterpenoid Dimers from Chloranthus multistachys", 《J. NAT. PROD.》 * |
| ZHA-JUN ZHAN等: "Natural disesquiterpenoids", 《NAT. PROD. REP.》 * |
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