CN106924243A - Application of the fraxinellone in antineoplastic sensitizer is prepared - Google Patents
Application of the fraxinellone in antineoplastic sensitizer is prepared Download PDFInfo
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- CN106924243A CN106924243A CN201511013918.0A CN201511013918A CN106924243A CN 106924243 A CN106924243 A CN 106924243A CN 201511013918 A CN201511013918 A CN 201511013918A CN 106924243 A CN106924243 A CN 106924243A
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- 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
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/365—Lactones
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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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/475—Quinolines; Isoquinolines having an indole ring, e.g. yohimbine, reserpine, strychnine, vinblastine
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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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
- A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
- A61K31/704—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin
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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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- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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Abstract
The invention belongs to cell biology and field of medicaments, She Ji application of the fraxinellone in antineoplastic sensitizer is prepared.Fraxinellone 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；Fraxinellone 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 antineoplastic He the pharmaceutical composition that fraxinellone is used in combination suppresses the method that tumor multi-medicine drug-resistant cell is bred.Small molecule compound fraxinellone 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, specifically, this invention She Ji the new application of fraxinellone.The present invention
Further relate 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.
The traditional Chinese medicine root bark of shaggy-fruited dittany is the dry root of rutaceae shaggy-fruited dittany (D ictamnusdasy carpus Turcz)
Skin, with wind-dispelling, eliminating dampness, heat-clearing, the effects such as removing toxic substances.It is anti-oxidant, disease-resistant that modern pharmacology research shows that the root bark of shaggy-fruited dittany has
The various active such as poison, antibacterium, anti-inflammatory, antitumor.Recent studies indicate that, the isolated fraxinellones, white from the root bark of shaggy-fruited dittany
Fresh alkali, obakunone are the main pharmacodynamics composition of the root bark of shaggy-fruited dittany, with various stronger bioactivity.Wherein, fraxinellones are used as one kind
New hepatosis treating medicine, with good protecting liver, lowering enzymes and suppression liver fibrosis isoreactivity, and lives with antibacterial, desinsection etc.
Property.
Zhu Danni etc. determines fraxinellone content in the white fresh hide of high effective liquid chromatography for measuring by HPLC（High performance liquid chromatography
Method determines Bai fresh hide Zhong fraxinellone contents, China Medicine University's journal, 1998,29 (4):319~320）.
Research both at home and abroad shows, He fraxinellone is main active material in dittany bark, it has and lures dictaminine to mite class
The effect of killing, has the function of Developing restraint to insect and has stronger cytotoxicity to 3 age mythimna separatas., former Chunlan etc. in 2005
Further Bao the insecticidal activity of fraxinellone（A kind of insecticidal activity of novel botanical pesticide ketone, plant protection, volume 31
5th phase).2009, former Chunlan etc. studied in detail to the extraction process of fraxinellone in dittany bark, obtained a kind of simple
Practical separating technology.Using industrial separation of this technique, fraxinellones yield up to 94.7%, Wei fraxinellone to provide one kind has
The method of effect（The 7th phase of volume 26, in July, 2009, the Study on extraction of property thing matter fraxinellone living, fine chemistry industry in dittany bark）.
Li Xiang etc. is also reported and the method for taking fraxinellone is put forward from the root bark of shaggy-fruited dittany（While Bei fraxinellones processed, dictamine, obakunone list from the root bark of shaggy-fruited dittany
The method of body, Sichuan University's journal (engineering science version), the No. 4 of V o.l 39）.
Fraxinellone is natural products, and bioavilability is high, Nature comparison is stable, with Clinical practice value.With people couple
What its chemistry and biology was studied gos deep into, and its molecular mechanism of action will progressively clearly, and this will further promote such chemical combination
The modifying for chemical structure and structure activity study of thing, and it is favorably improved the medical value of shaggy-fruited dittany.
The content of the invention
The new medicinal usage of purpose Shi Ti Gong fraxinellones of the invention.
It is an object of the invention to provide a kind of antineoplastic sensitizer.
On the one hand, application of the Ti Gong fraxinellones of the present invention in antineoplastic sensitizer is prepared.The wherein English of , fraxinellones
Full name is Fraxinellone, 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.
Fraxinellone 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 He fraxinellone.
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
Middle Jia Ru fraxinellones and antineoplastic.
Wherein, the final concentration of 1-100 μm of ol/L of Jia Ru fraxinellones.
Described tumour includes carcinoma of mouth, breast cancer, liver cancer, lung cancer, cervical carcinoma or cancer of pancreas.
When implementing the above method, first Jia Ru fraxinellones are subsequently adding antineoplastic.Jia Ru fraxinellones can also be swollen with anti-simultaneously
Tumor medicine.
The new application of Ti Gong fraxinellones of the present invention, i.e. its application in antineoplastic sensitizer is prepared.Fraxinellone is day
Right product, the effect with reversing multiple medicine resistance of tumor cells can be as the reversal agent of tumor multi-medicine drug-resistant；Fraxinellone also has
Increase the effect of tumor multi-medicine drug-resistant cells against neoplastic drug susceptibility, can be used as chemotherapeutic sensitizer.In the present invention
Small molecule compound fraxinellone developed as new antineoplastic or its auxiliary element, tumor killing effect substantially, green
Environmental protection, will provide a kind of new approach and means to treat and curing tumour.
Brief description of the drawings
The structure of the Wei fraxinellones of figure 1.
Specific embodiment
The invention provides a kind of antineoplastic, the active component Shi fraxinellones of described antineoplastic.Described is swollen
Knurl 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 phase interaction occurs with fraxinellone
Material, 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 this Fa Ming fraxinellones as an example, it can be combined with suitable pharmaceutically acceptable carrier.This kind of medicine group
Compound contains the compound and pharmaceutically acceptable carrier or excipient of therapeutically effective amount.This kind of carrier includes（But do not limit
In）：Salt solution, buffer solution, glucose, water, glycerine, ethanol, and combinations thereof.Pharmaceutical preparation should match with administering mode.This hair
Ming fraxinellones can be made into injection form, and for example the aqueous solution with physiological saline or containing glucose and other assistant agents is by normal
Rule method is prepared.The pharmaceutical composition of such as tablet and capsule etc, can be prepared by conventional method.Drug regimen
Thing such as injection, solution, tablet and capsule are preferably aseptically manufactured.The dosage of active component is therapeutically effective amount, for example
The daily mg/kg body weight of about 1 microgram/kg body weight-about 5.In addition, the fraxinellone of Ben Faming can also be together with other therapeutic agents
Use.Certainly, specific dosage is also contemplated that the factors such as method of administration, patient health situation, and these are all skilled practitioners technical ability models
Within enclosing.
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.MCF-7 cell culture is in the RPMI 1640 containing 10% hyclone
In culture medium, KB and KB/VCR cell culture is trained in the MEM containing 10% hyclone, 2mM glutamine and 1mM Sodium Pyruvates
Support in base, MCF-7/ADR cell culture is in the MEM containing 10% hyclone, 0.01mg/ml insulin and 1mM Sodium Pyruvates
In culture medium.Penicillin containing 100U/ml and 100 μ g/ml streptomysins in culture medium.
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：
Fraxinellone is dissolved in DMSO (dimethyl sulfoxide (DMSO)), and the mother liquor for being configured to 100mM or 50mM is standby.
Vincristine (VCR) and adriamycin (ADR) are purchased from Roche chemical company, and 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 is purchased from company of Nanjing Keygen Biotech.
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, fraxinellone and VCR and fraxinellone one are reinstated after the α-MEM containing 10% hyclone are prepared and added
To in each hole.After cultivating 48 h, nutrient solution is discarded, culture medium and 10 μ L CCK-8s of the 90 μ L without serum are added per hole
Reagent.After 37 DEG C of 2 h of reaction, ELIASA reads the light absorption value of 450 nm wavelength（OD450）.It is relative by being calculated medication group
In the cell growth fraction of control group.Blank group only adds culture medium to be not added with cell, and control group is to add and medicine same volume
DMSO, cell survival rate=（Experimental group OD450- blank groups OD450）/（Control group OD450- blank groups OD450）.By IC50Value
Resistance multiple is calculated 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 fraxinellone to parental cell strain KB and MCF-750Respectively 198.6 μ Μ and 191.2 μ Μ,
To the IC of drug-resistant cell strain KB/VCR and MCF-7/ADR50Respectively 264.2 μ Μ and 277.9 μ Μ are poor without conspicuousness between the two
Not, multidrug resistance cell strain KB/VCR and MCF-7/ADR does not show the crossing drug resistant to Hua He Wu fraxinellones, and Shuoing Ming fraxinellones can
To escape the multidrug resistance of mdr cell.Fraxinellone suppresses in 10 μ Μ and following concentration, cell growth without obvious,
The propagation of cell can be suppressed under concentration higher than 100 μ Μ.
Conclusion：Fraxinellone can overcome the drug resistance of drug-resistant cell strain, and the sensitiveness of drug-resistant cell strain Dui fraxinellones is essentially identical.
Embodiment 2：Reverse effect of the CCK-8 Fang methods Jian Ce fraxinellones 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 are prepared with the VCR and fraxinellone one of the VCR of concentration, and various concentrations and be added to each
Kong Zhong.After cultivating 48 h, nutrient solution is discarded, with method in embodiment 1, drug-resistant cell strain and its parent are surveyed with CCK-8 kits
This cell plots curve to the activity of VCR and VCR+ fraxinellones.Each concentration sets 3 repeating holes, and 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 μ M fraxinellones, make sensitiveness increase of the KB/VCR cells to VCR not notable, and ADR is to mdr cell MCF-7/ADR's
Sensitiveness increased 1.58 times.Fraxinellone can reverse multiple drug resistance of tumor cell to the drug resistance of chemotherapeutics.And this effect
Show unobvious in parental cell.
Conclusion：
Fraxinellone can be with the drug resistance of reverse multiple drug resistance of tumor cell KB/VCR and MCF-7/ADR, can be as antineoplastic
Sensitizer, or be made pharmaceutical composition 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 fraxinellone in antineoplastic is prepared, described Ying Yong Shi fraxinellones are in antineoplastic sensitizer is prepared
Using.
2. application as claimed in claim 1, it is characterized in that , fraxinellones are 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 is He fraxinellone.
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
Fraxinellone 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 Jia Ru fraxinellones, is subsequently adding antineoplastic.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201511013918.0A CN106924243A (en) | 2015-12-31 | 2015-12-31 | Application of the fraxinellone in antineoplastic sensitizer is prepared |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114259488A (en) * | 2022-01-27 | 2022-04-01 | 杭州师范大学 | Application of traditional Chinese medicine molecule fraxinellone in preparation of medicine for treating glioma |
-
2015
- 2015-12-31 CN CN201511013918.0A patent/CN106924243A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114259488A (en) * | 2022-01-27 | 2022-04-01 | 杭州师范大学 | Application of traditional Chinese medicine molecule fraxinellone in preparation of medicine for treating glioma |
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Application publication date: 20170707 |