CN106806362A - Application of the dehydrogenation rush diphenol in antineoplastic sensitizer is prepared - Google Patents
Application of the dehydrogenation rush diphenol in antineoplastic sensitizer is prepared Download PDFInfo
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- CN106806362A CN106806362A CN201510869916.5A CN201510869916A CN106806362A CN 106806362 A CN106806362 A CN 106806362A CN 201510869916 A CN201510869916 A CN 201510869916A CN 106806362 A CN106806362 A CN 106806362A
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- rush
- diphenol
- dehydrogenation
- antineoplastic
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
- A61K31/05—Phenols
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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Abstract
The invention belongs to cell biology and field of medicaments, it is related to application of the dehydrogenation rush diphenol in antineoplastic sensitizer is prepared.Dehydrogenation rush diphenol is natural products, the effect with reversing multiple medicine resistance of tumor cells, can be as the reversal agent of tumor multi-medicine drug-resistant；Dehydrogenation rush diphenol also has increases the effect of tumor multi-medicine drug-resistant cells against neoplastic drug susceptibility, can be used as chemotherapeutic sensitizer.Present invention also offers the method that the pharmaceutical composition that antineoplastic and dehydrogenation rush diphenol are used in combination suppresses tumor multi-medicine drug-resistant cell propagation.Micromolecular compound dehydrogenation rush diphenol in the present invention is developed as new antineoplastic or its auxiliary element, and substantially, environmental protection will provide a kind of new approach and means to tumor killing effect to treat and curing tumour.
Description
Technical field
The invention belongs to cell biology and field of medicaments field, and in particular to the new application of dehydrogenation rush diphenol.This
Invention further relates to corresponding pharmaceutical composition and its application process.
Background technology
Tumour is body under the effect of various carcinogenic factors, and some cell of local organization loses right on gene level
The normal regulation of its growth, the abnormality for causing its clonal abnormality hyperplasia and being formed.The neoplastic disease number of cases of China is quite huge
Greatly, there is data to show and account for the 55% of whole world case load.
Influence of the benign tumour to body is smaller, is mainly shown as local compression and obstructive symptom.Malignant tumour is due to dividing
Change immature, growth very fast, infiltration destroys the 26S Proteasome Structure and Function of organ, and can shift, thus serious on body influence.Dislike
Property tumour can have heating, intractable pain in addition to it can cause local compression and the obstructive symptom similar to above-mentioned benign tumour, also,
Late period may occur in which seriously become thin, the state of weak, anaemia and cachexia.
The traditional Chinese medical science thinks that the cause of cancer is equilibrium between yin and yang in human body first, and histocyte is long-term in different carcinogenic factors
Under effect, cell mutation and cause.Cancerous tissue is also a part for human body in fact, only in this imbalance between YIN and YANG of people, five
Raw gram of row multiplies on the premise of insult changes, and the immunosurveillance system of human body can just lose monitoring to it, develop as one pleases.Chinese herbal medicine
Can with recuperating qi-blood, adjustment equilibrium between yin and yang, maintain normal vital signs and save one's life；To train correction gas, produce antibody, cleaning "
Malicious source " and effect a permanent cure.Thus, Chinese herbal medicine extract turns into treatment one important directions of tumour.
Dehydrogenation rush diphenol extracts from Chinese herbal medicine rush.Rush（Scientific name：Juncus effusus L）It is for many years
Raw herbaceous aquatic vegetation, subterranean stem is short, crawling property, and stalk is grown thickly uprightly, and cylindrical shape is solid, basal part of stem tool brown, and it is in scale to degenerate
Shape first sheathing leaf, spike, basidixed, in false side life shape on stem, it is in bulbous that base portion bract extends, and spends 2 pieces of squamellas of lower tool, perianth
6 pieces of sliver, 3 pieces of stamen, the difference of pistil stigma 3.Isabelline capsule, elliptical or oval shape, seed yellow is in obovate.Rush
Be also medicinal plant, the effect of its stem marrow or all herbal medicine have heat-clearing, clearing damp and promoting diuresis, can be used for gonorrhoea, oedema, it is vexed not
Sleep, larynx numbness, the disease such as wound.
Dehydrogenation rush diphenol belongs to natural products, and bioavilability is high, Nature comparison is stable, with Clinical practice valency
Value.Report is less in terms of the chemical constitution research of dehydrogenation rush diphenol at present, and the bioactivity research of system is less.With
People going deep into its chemistry and biology research, its molecular mechanism of action will progressively clearly, and this will further be promoted
The modifying for chemical structure and structure activity study of such compound, and it is favorably improved the medical value of rush.
The content of the invention
It is an object of the invention to provide the new medicinal usage of dehydrogenation rush diphenol.
It is an object of the invention to provide a kind of antineoplastic sensitizer.
On the one hand, the application the invention provides dehydrogenation rush diphenol in antineoplastic sensitizer is prepared.Wherein,
The English full name of dehydrogenation rush diphenol is dehydroeffusol, and its structure is as shown in Figure 1.
Described tumour includes carcinoma of mouth, breast cancer, liver cancer, lung cancer, cervical carcinoma, colon cancer or cancer of pancreas.
Described antineoplastic is vincristine, daunorubicin, taxol or 5 FU 5 fluorouracil.
Dehydrogenation rush diphenol can be as tumor multi-drug resistance reversal agents.
On the other hand, the invention provides a kind of antineoplastic pharmaceutical compositions, described antineoplastic pharmaceutical compositions have
Effect composition is antineoplastic and dehydrogenation rush diphenol.
Described antineoplastic is CCSA or cell cycle nonspecific agent (CCNSA).
Described antineoplastic is vincristine, daunorubicin, taxol or 5 FU 5 fluorouracil.
Present invention also offers a kind of method for suppressing tumor cell in vitro growing multiplication, i.e., in the culture medium of tumour cell
It is middle to add dehydrogenation rush diphenol and antineoplastic.
Wherein, the final concentration of 1-100 μm of ol/L of dehydrogenation rush diphenol is added.
Described tumour includes carcinoma of mouth, breast cancer, liver cancer, lung cancer, cervical carcinoma or cancer of pancreas.
When implementing the above method, dehydrogenation rush diphenol is first added, be subsequently adding antineoplastic.Can also add simultaneously
Dehydrogenation rush diphenol and antineoplastic.
The invention provides the new application of dehydrogenation rush diphenol, i.e. its answering in antineoplastic sensitizer is prepared
With.Dehydrogenation rush diphenol is natural products, the effect with reversing multiple medicine resistance of tumor cells, can be resistance to as tumour multiple medicine
The reversal agent of medicine；Dehydrogenation rush diphenol also has increases the effect of tumor multi-medicine drug-resistant cells against neoplastic drug susceptibility,
Can be used as chemotherapeutic sensitizer.Micromolecular compound dehydrogenation rush diphenol in the present invention is used as new antineoplastic
Or its auxiliary element is developed, tumor killing effect substantially, environmental protection, by for treat and cure tumour provide it is a kind of newly
Approach and means.
Brief description of the drawings
Fig. 1 is the structure of dehydrogenation rush diphenol.
Specific embodiment
The invention provides a kind of antineoplastic, the active component of described antineoplastic is dehydrogenation rush two
Phenol.Described tumour can be HCC, stomach cancer cell, cervical cancer cell or blood cell.
Micromolecular compound of the invention can be prepared using various conventional preparation methods.For example, using artificial chemistry
The method of synthesis.
Using micromolecular compound of the present invention, by various conventional screening assays, can filter out and dehydrogenation rush diphenol
The material for interacting, such as acceptor, inhibitor or antagonist.
The present invention and its inhibitor, antagonist etc., when (administration) is administered in treatment, it is possible to provide different effects.
Generally, these materials can be formulated in nontoxic, inert and pharmaceutically acceptable aqueous carrier medium, wherein pH is usual
About 5-8, preferably pH be about 6-8, pH value can be varied from the property for being formulated material and illness to be treated.
The pharmaceutical composition for preparing can be administered by conventional route, including（But it is not limited to）：Intramuscular, intraperitoneal,
Subcutaneous, intracutaneous or local administration.
By taking dehydrogenation rush diphenol of the invention as an example, it can be combined with suitable pharmaceutically acceptable carrier.
This kind of pharmaceutical composition contains the compound and pharmaceutically acceptable carrier or excipient of therapeutically effective amount.This kind of carrier includes
（But it is not limited to）：Salt solution, buffer solution, glucose, water, glycerine, ethanol, and combinations thereof.Pharmaceutical preparation should be with administering mode phase
Matching.Dehydrogenation rush diphenol of the invention can be made into injection form, for example with physiological saline or containing glucose and its
He is prepared the aqueous solution of assistant agent by conventional method.The pharmaceutical composition of such as tablet and capsule etc, can be by routine
Method is prepared.Pharmaceutical composition such as injection, solution, tablet and capsule are preferably aseptically manufactured.Active component is given
Dose is therapeutically effective amount, such as the daily mg/kg body weight of about 1 microgram/kg body weight-about 5.Additionally, dehydrogenation of the invention
Rush diphenol can also be used together with other therapeutic agents.Certainly, specific dosage is also contemplated that method of administration, patient health shape
The factors such as condition, within the scope of these are all skilled practitioners technical ability.
Experimental technique：
1. cell recovery
1) cryopreservation tube is taken out from liquid nitrogen container, in direct plungeing into 37 DEG C of warm water, and shake makes it melt as early as possible frequently.
2) take out cryopreservation tube from 37 DEG C of water-baths, with suction pipe suction out cell suspension, injection centrifuge tube and addition more than 10 times
Nutrient solution, low-speed centrifugal after mixing, abandons supernatant, repeats and is washed once with nutrient solution.
3) after suitably being diluted with nutrient solution, inoculated and cultured bottle is placed on 37 DEG C of incubator quiescent cultures, and next day changes culture
Liquid, continues to cultivate.Passed on when culture is to finite concentration.PANC-1 cell culture is containing 10% Gibico hyclones
In DMEM high glucose mediums；The cell culture such as K562, HGC, QGY, MCF-7, PC-3 are in 1640 cultures containing 10% hyclone
In base, SK-hep1, HeLa, HepG2, etc. cell culture in the DMEM high glucose mediums containing 10% hyclone, in culture medium
Penicillin containing 100U/ml and 100 μ g/ml streptomysins.
2. passage culture
The situation of daily observation of cell growth, passes on when when cell, length is converged to about 90% in blake bottle, is about passed every 2-4 days
In generation, is once.One bottle passes on into three bottles, or 25 cm2Pass in 75 cm2Blake bottle in.Method：
1) with 1 × phosphate buffer washed cell once.
2) digestion of 2-3ml pancreatin digestive juice is added, several minutes in 37 DEG C of incubators are placed in.Tissue Culture Flask is patted with hand,
Make cell separation.
3) terminate pancreatin with the suitable culture medium of the Gibico hyclones containing 10-15% to digest.Cell is sub-packed in newly
Blake bottle in, continue cultivate.
When suspension cell is passed on, centrifugation in centrifuge tube is collected directly from, abandons old culture medium.General one bottle passes on into three bottles
Ratio is sub-packed in new blake bottle, adds fresh culture to continue to cultivate.
3. cell cryopreservation
1) the cell Trypsin Induced of culture to exponential phase is taken, is collected in centrifuge tube and is counted, be centrifuged.
2) reject trypsase and old nutrient solution, what addition had been configured freezes nutrient solution (containing 10% DMSO, 40%
DMEM and 50% Gibico hyclones), the ultimate density of cell is 0.5- 1 × 10 in frozen stock solution7/ml.Gently blown with suction pipe
Beating makes cell uniform, is then distributed into aseptic cryopreservation tube, often pipe -1.5ml of Jia 1.
3) cryopreservation tube is put into freezing storing box and puts -80 DEG C of quick-frozen, preservations in immigration liquid nitrogen container after 5 hours.
4. experiment material
Medicine prepares：
Dehydrogenation rush diphenol is dissolved in DMSO (dimethyl sulfoxide (DMSO)), and the mother liquor for being configured to 100mM or 50mM is standby.
Dehydrogenation rush diphenol can be from Shanghai Zhen Zhun bio tech ltd（No. CAS:137319-34-7）Purchase.
The structure of dehydrogenation rush diphenol is as shown in Figure 1.
Verapamil（VPL）, vincristine (VCR) and adriamycin (ADR) be purchased from Roche chemical company, purity is both greater than
99%。
Cell derived:
Human oral cancer cell line KB and its drug-resistant cell strain KB/VCR are provided by Chinese Academy of Sciences's medicine, Breast cancer lines MCF-
7 and its drug-resistant cell strain MCF-7/ADR, human colon carcinoma HCT-8 and its drug-resistant cell strain HCT-8/VCR are purchased from Nanjing Kai Jisheng
Thing company.
Kit:
CCK-8 kits are purchased from colleague company.
CCK-8 is tested
KB and KB/VCR cells and MCF-7 and MCF-7/ADR cells are all inoculated into 96 orifice plates according to the density in 3500/ hole,
The ADR of various concentrations after 24 h, VCR, dehydrogenation rush diphenol and VCR and dehydrogenation rush diphenol one are reinstated containing 10% tire ox
α-the MEM of serum are added in each hole after preparing.After cultivating 48 h, nutrient solution is discarded, add 90 μ L to be free of serum per hole
Culture medium and 10 μ L CCK-8 reagents.After 37 DEG C of 2 h of reaction, ELIASA reads the light absorption value of 450 nm wavelength（OD450）.
By being calculated cell growth fraction of the medication group relative to control group.Blank group only adds culture medium to be not added with cell, compares
Group is to add the DMSO with medicine same volume, cell survival rate=（Experimental group OD450- blank groups OD450）/（Control group OD450-
Blank group OD450）.By IC50Value calculates resistance multiple again（Resistance Fold, RF）.
The IC of RF=drug-resistant cell strain50The IC of value/parental cell strain50Value.Each concentration sets 3 repeating holes, real
Test repetition 3 times.
All mdr cells grow 3 days before tying up to Cell suppression test in without pharmaceutical culture medium.Each numerical value is 3
Independent experiment result, IC50Represented in " means standard deviation " form.VCR, vincristine；ADR, daunorubicin；RF, resistance times
Number.
Embodiment 1
Experimental result：
KB/VCR and MCF-7/ADR are two kinds of conventional multidrug resistance cell strains, and in the present embodiment, both cells are also showed
Go out the characteristic of MDR.As shown in table 1, KB/VCR cells are respectively relative to KB cells to the resistance multiple of VCR and ADR
81.9 times and 94.4 times, and MCF-7/ADR cells are respectively 38.1 times compared to the resistance multiple to VCR and ADR with MCF-7 cells
With 20.9 times, display experiment mdr cell used has multidrug resistance, and MDR activity similar to the result of document report.
Half-inhibition concentration IC of the dehydrogenation rush diphenol to parental cell strain KB and MCF-750Respectively 223.1 μ Μ and
189.6 μ Μ, to the IC of drug-resistant cell strain KB/VCR and MCF-7/ADR50Respectively 232.7 μ Μ and 196.4 μ Μ, between the two
Without difference, multidrug resistance cell strain KB/VCR and MCF-7/ADR are not shown to compound dehydrogenation rush diphenol
Crossing drug resistant, illustrate that dehydrogenation rush diphenol can escape the multidrug resistance of mdr cell.Dehydrogenation rush diphenol is 20
Under the concentration of below μ Μ, cell growth can suppress the propagation of cell without obvious suppression under the concentration higher than 100 μ Μ.
Test result indicate that：Dehydrogenation rush diphenol can overcome the drug resistance of drug-resistant cell strain, and drug-resistant cell strain is to going
The sensitiveness of hydrogen rush diphenol is essentially identical.
Embodiment 2：CCK-8 methods detect reverse effect of the dehydrogenation rush diphenol to tumor cell multidrug resistance activity
KB/VCR, MCF-7/ADR and HCT-8/VCR cell are inoculated into 96 orifice plates according to the density in 3500/ hole, after 24 h not
Reinstated after the α-MEM containing 10% hyclone prepare with the VCR and dehydrogenation rush diphenol one of the VCR of concentration, and various concentrations
It is added in each hole.After cultivating 48 h, nutrient solution is discarded, with method in embodiment 1, survey resistance with CCK-8 kits thin
Born of the same parents' strain and its parental cell plot curve to the activity of VCR and VCR+ dehydrogenation rush diphenol.Each concentration sets 3 repetitions
Hole, experiment is repeated 3 times.
Experimental result：
KB/VCR cells are 81.9 times to the resistance multiple of VCR, and MCF-7/ADR is 20.9 times to the resistance multiple of ADR.Work as addition
After 10 μM of dehydrogenation rush diphenol, KB/VCR cells are made to increased 6.82 times to the sensitiveness of VCR, and ADR is to mdr cell
The sensitiveness of MCF-7/ADR increased 7.10 times.Dehydrogenation rush diphenol can reverse multiple drug resistance of tumor cell to chemotherapeutic
The drug resistance of thing.And this effect shows unobvious in parental cell.
Test result indicate that, dehydrogenation rush diphenol can be with reverse multiple drug resistance of tumor cell KB/VCR and MCF-7/ADR
Drug resistance, as the sensitizer of antineoplastic, or pharmaceutical composition can be made with antineoplastic.
The all documents referred in the present invention are all incorporated as reference in this application, independent just as each document
It is incorporated as with reference to such.In addition, it is to be understood that after above-mentioned instruction content of the invention has been read, those skilled in the art can
Made various changes or modifications with to the present invention, these equivalent form of values equally fall within the model that the application appended claims are limited
Enclose.
Claims (10)
1. application of the dehydrogenation rush diphenol in antineoplastic sensitizer is prepared.
2. application as claimed in claim 1, it is characterised in that dehydrogenation rush diphenol is tumor multi-drug resistance reversal agents.
3. application as claimed in claim 1, it is characterised in that described tumour includes carcinoma of mouth, nasopharyngeal carcinoma, breast cancer, liver
Cancer, lung cancer, cervical carcinoma, colon cancer or cancer of pancreas.
4. application as claimed in claim 1, it is characterised in that described antineoplastic is vincristine, daunorubicin, purple
China fir alcohol or 5 FU 5 fluorouracil.
5. a kind of antineoplastic pharmaceutical compositions, it is characterised in that the active ingredient of described antineoplastic pharmaceutical compositions is anti-swollen
Tumor medicine and dehydrogenation rush diphenol.
6. antineoplastic pharmaceutical compositions as claimed in claim 5, it is characterised in that described antineoplastic is the cell cycle
Specific drug or cell cycle nonspecific agent (CCNSA).
7. antineoplastic pharmaceutical compositions as claimed in claim 5, it is characterised in that described antineoplastic is new Changchun
Alkali, daunorubicin, taxol or 5 FU 5 fluorouracil.
8. it is a kind of suppress tumor cell in vitro growing multiplication method, it is characterised in that in the culture medium of tumour cell add
Dehydrogenation rush diphenol and antineoplastic.
9. method as claimed in claim 8, it is characterised in that described tumour includes carcinoma of mouth, breast cancer, nasopharyngeal carcinoma, liver
Cancer, lung cancer, cervical carcinoma or cancer of pancreas.
10. method as claimed in claim 8, it is characterised in that first add dehydrogenation rush diphenol, be subsequently adding antineoplastic
Thing.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510869916.5A CN106806362A (en) | 2015-12-02 | 2015-12-02 | Application of the dehydrogenation rush diphenol in antineoplastic sensitizer is prepared |
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| CN201510869916.5A CN106806362A (en) | 2015-12-02 | 2015-12-02 | Application of the dehydrogenation rush diphenol in antineoplastic sensitizer is prepared |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111246849A (en) * | 2017-10-19 | 2020-06-05 | 株式会社佐藤园 | Composition for enhancing learning and memory ability |
-
2015
- 2015-12-02 CN CN201510869916.5A patent/CN106806362A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111246849A (en) * | 2017-10-19 | 2020-06-05 | 株式会社佐藤园 | Composition for enhancing learning and memory ability |
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Application publication date: 20170609 |