CN102440985A - Application of bixanthone compound FLBG-1108 or its medicinal salt in preparing anticancer medicaments - Google Patents
Application of bixanthone compound FLBG-1108 or its medicinal salt in preparing anticancer medicaments Download PDFInfo
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Abstract
The invention discloses application of a bixanthone compound FLBG-1108 or its medicinal salt in preparing anticancer medicaments. The invention, by means of experiments, finds that the bixanthone compound FLBG-1108 has an obvious inhibition effect on propagation of human non-small cell lung cancer H520, A549, H549, 1299, human breast cancer cell MCF7, human prostatic cancer cell PC3, LNcaP, DU145, as well as human intestinal cancer cell SW480 and HT-2P, can selectively inhibit the propagation of the human lung cancer cell H520, and presents good time and concentration dependence. After 48h of action, the IC50 value is 2.90 micrometers, which shows no cytotoxicity to a normal kidney epidermal cell. Further, the bixanthone compound FLBG-1108 is found to play an effective role in inducing apoptosis of the lung cancer cell H520, preventing propagation of cancer cells but showing no toxicity, and can specifically block the cell cycle of the lung cancer cell H520 in S stage, thus inhibiting the propagation of cancer cells. Therefore, the bixanthone compound FLBG-1108 can be developed into novel candidate medicaments with an anticancer effect, especially an anti-lung cancer effect.
Description
Technical field:
The invention belongs to the medical compounds field, diketone (bixanthone) compounds FLBG-1108 or its pharmaceutical salts of being specifically related to a kind of natural plants source are preparing cancer therapy drug, the especially application in the preparation anti-lung-cancer medicament.
Background technology:
In recent years, cancer progressively rises becomes the second largest disease that threatens the human life.In many cancers, the sickness rate of pulmonary carcinoma is high always, and is the trend that rises year by year.At present be used to treat the broad-spectrum anti-cancer drug that is mostly of pulmonary carcinoma clinically, belong to cytotoxin class medicine mostly, as the cyclophosphamide that passes through to influence cancerous cell dna structure and function, cisplatin, mitomycin, podophyllotoxin derivative etc.; Through the transcription and the synthetic anthracene nucleus medicament of prevention RNA of interfere with cancer cells RNA, like doxorubicin; Also has plant source cancer therapy drug, like vinblastine and paclitaxel etc. through proteinic synthetic and function of anticancer.Yet in this numerous cancer therapy drug, it is but very rare to have optionally a cancer therapy drug.And the broad-spectrum anti-cancer drug that uses at present has toxicity, side effect in various degree, in the process of chemotherapy, causes patient body weakness, alopecia, vomiting, gastrointestinal upset, and nervous system disease etc.
The plant source medicine shows peculiar biological activity with its complicated and diversified structure, in clinical use, has above the ordinary performance.From natural plants, seeking to have better bioactive natural product has been the confessed fact of biological educational circles and medicament research and development enterprise.Global scientist all in various degree from plant, seek the specially good effect plant amedica to all kinds of diseases, many unexpected discoveries and results are also arranged.This type of medicine is lower to human toxicity, and structure is peculiar, is to be difficult in the synthetic chemistry realize.Therefore, the screening cancer therapy drug has wide space from these natural products, and very big feasibility is also arranged.
The Xanthone compounds is that one type of ten minutes extensively is present in natural chemical compound, and comparatively outstanding with the Garcinia plant, this compounds has good antioxidation mostly, especially is celebrated with " Manggis " after the fruit that is rich in xanthone.Research indicates, biological activity such as that the xanthone compounds has is antibiotic, antiinflammatory, antiviral, and part of compounds is developed to depressor, medicines such as antithrombotic.The anticancer natural xanthone class medicine that has successfully found out at present has Gambogic acid, and antileukemie medicine Psorospermin, is the basis with the xanthone parent nucleus; Medicine synthetic and that derive out also comprises Thioxanthones, Epoxyxanthones, Acylxanthones; Bisxahnthones, Bisfuranoxanthones, Extended xanthones; Oxygenated xanthones, Imidazolyxanthones etc.
Diketone (bixanthone) compounds FLBG-1108; Its structure is suc as formula shown in (I); Be from 90% ethanol extraction of medicinal plants south of the Five Ridges Cortex Garciniae (Garcinia oblongifolia Champ) bark, to separate to obtain, molecular weight is 652, purity >=97%.Its chemical constitution employing nuclear magnetic resonance, NMR (
1H NMR,
13C NMR, HSQC, HMBC NOESY), high resolution mass spectrum modern spectroscopic techniques such as (HRESI-MS) identifies, and compares affirmation with the spectrum data of the chemical compound Griffipavixanthone of existing bibliographical information.South of the Five Ridges Cortex Garciniae bark picks up from Zhaoqing Dinghu Hill, Guangdong Province, identifies that by Xian Hu botanical garden professor Chen Tao of the Shenzhen Chinese Academy of Sciences sample preservation is in BIAO and BEN shop, Xian Hu botanical garden (N.2008100801).List of references: Yuan-Jian Xu, Shu-Geng Cao, Xiao-Hua Wu, Yee-Hing Lai; B.H.K.Tan, J.T.Pereira, S.H.Goh; Ganapathi Venkatraman, Leslie J.Harrison, and Keng-Yeow Sim.Griffipavixanthone; A novel cytotoxic bixanthone from garcinia griffithii and G.pavifolia.Tetrahedron letters, 1998,39:9103-9106.
Formula (I)
Summary of the invention:
First purpose of the present invention provides suc as formula diketone (bixanthone) compounds FLBG-1108 shown in (I) or the application of its pharmaceutical salts in the preparation cancer therapy drug.
The present invention is through the anti tumor activity in vitro screening; Proof diketone (bixanthone) compounds FLBG-1108 is to people's nonsmall-cell lung cancer H520, A549, H549,1299; Human breast cancer cell MCF7; Human Prostate Cancer Cells PC3, LNcaP, DU145, the propagation of people's colon-cancer cell SW480, HT-2P has the obvious suppression effect.To human lung carcinoma cell H520, Human Prostate Cancer Cells DU145 and LNCaP, people's colon-cancer cell SW480 and HT-29, human breast cancer cell MCF-7 has good inhibitory effect, its half-inhibition concentration (IC
50Value) between 2.9～6.7 μ M, and not obvious to the inhibited proliferation of human liver cancer cell HepG2.Diketone (bixanthone) compounds FLBG-1108 optionally suppresses the propagation of human lung carcinoma cell H520, and demonstrates time and concentration dependent preferably, the IC of effect 48h
50Value is 2.90 μ M, and this concentration does not show cytotoxicity to normal kidney epidermis cell.Further detect apoptosis through two methods of dying, experimental result proves, is respectively 3.125,6.25 in administration concentration, and during 12.5 μ M, FLBG-1108 can effectively induce the apoptosis of lung carcinoma cell H520, stops cancer cell multiplication, and does not show toxicity.Simultaneously, the cell cycle experimental result shows that FLBG-1108 can block in the S phase by specific cell cycle with lung carcinoma cell H520, has suppressed the propagation of cancerous cell.Show by The above results; Diketone (bixanthone) compounds FLBG-1108 has the effect that selectivity suppresses proliferation of lung cancer cells; And this effect realizes that with the blocking-up cell cycle it is strong to have a selectivity through apoptosis-induced, and antitumaous effect is clear and definite; The characteristic that toxic and side effects is little, can develop becomes the candidate new medicine with effect of anti-lung cancer.
Therefore diketone of the present invention (bixanthone) compounds FLBG-1108 or its pharmaceutical salts can be applicable to prepare cancer therapy drug, especially anti-lung-cancer medicament.
Second purpose of the present invention provides a kind of cancer therapy drug, and it contains the diketone as active component (bixanthone) compounds FLBG-1108 or its pharmaceutical salts of effective dose.This cancer therapy drug can be pure compound FLBG-1108 or its pharmaceutical salts, perhaps is the pharmaceutical composition that compound F 17-hydroxy-corticosterone LBG-1108 or its pharmaceutical salts and pharmaceutically acceptable carrier or other pharmacologically active chemical compounds are formed.
Described cancer therapy drug can be made into the pharmacy acceptable forms, like tablet, pill, capsule, granule, solution, suspensoid or Emulsion.
Diketone of the present invention (bixanthone) compounds FLBG-1108 can suppress the propagation of multiple cancerous cell; Particularly has selectivity and suppress the effect of proliferation of lung cancer cells, and this effect realizes with the blocking-up cell cycle through apoptosis-induced that it is strong to have a selectivity; Antitumaous effect is clear and definite; The characteristic that toxic and side effects is little can be developed to become and has antitumaous effect, especially the candidate new medicine of effect of anti-lung cancer.
Description of drawings
Fig. 1 is FLBG-1108 extracorporeal suppression tumor cell and normal kidney epidermal cell proliferation experimental result;
Fig. 2 is time and the concentration curve that FLBG-1108 suppresses lung carcinoma cell H520 propagation;
Fig. 3 is that FLBG-1108 induces lung carcinoma cell H520 apoptosis figure;
Fig. 4 is that the cell cycle of FLBG-1108 control lung carcinoma cell H520 is in the S phase.
The specific embodiment:
For further illustrating value and significance of the present invention, below in conjunction with embodiment the present invention is done further explanation, but be not limitation of the present invention.
One, the preparation of diketone (bixanthone) compounds FLBG-1108
The bark (4kg) of south of the Five Ridges Cortex Garciniae (Garcinia oblongifolia Champ) is dried the back pulverizing in 60 ℃ of baking ovens; Using the 20L volume fraction is 90% ethanol water lixiviate at normal temperatures 2 times; Each 48 hours, merge ethanol extract and concentrating under reduced pressure and get always thick extracted extract 300g.Gained extractum makes into suspension with the 1000mL water dissolution, extracts respectively 4 times with isopyknic petroleum ether and ethyl acetate successively again.Get the 110g of ethyl acetate portion behind the combined ethyl acetate extract concentrating under reduced pressure.Ethyl acetate extraction portion is through normal pressure silica gel (200-300 order) column chromatogram chromatography; With the chloroform-methanol is eluant, carries out gradient elution in 95: 5 to 60: 40 from volume ratio, detects with thin layer chromatography to merge same composition; Used developing solvent was followed successively by volume ratio chloroform-acetone 3: 1; And chloroform-methanol 10: 1, chloroform-methanol-water 100: 11: 1, and chloroform-methanol-water 100: 23: 3.Detect the merging same composition with thin layer chromatography; The available successively chloroform of obtained component-acetone volume ratio is 3: 1, and the chloroform-methanol volume ratio is 10: 1, and chloroform-methanol-water volume ratio is 100: 11: 1; Chloroform-methanol-water 100: 23: 3 launches, and is divided into four each and every one components.In thin layer chromatography, can use chloroform-methanol-water volume ratio is 100: 23: 3: the unfolded component of solution system; Through reverse phase silica gel (75 μ) column chromatography; 75% methanol-water eluting; Get white powder chemical compound 1 (65mg), this chemical compound identifies that through structural analysis its spectroscopy data are following: molecular formula is C
36H
28O
12, ESIMS:m/z 653 [M+H]
+, 675 [M+Na]
+, 651 [M-H]
- 1H NMR (400MHz) and
13C NMR (100MHz) data are seen table 1, with list of references Yuan-Jian Xu, Shu-Geng Cao, Xiao-Hua Wu; Yee-Hing Lai, B.H.K.Tan, J.T.Pereira; S.H.Goh, Ganapathi Venkatraman, Leslie J.Harrison; And Keng-Yeow Sim.Griffipavixanthone, a novel cytotoxic bixanthone from garcinia griffithii and G.pavifolia.Tetrahedron letters, 1998; The data consistent of 39:9103-9106 identifies that thus its structure suc as formula shown in (I), is diketone (bixanthone) compounds FLBG-1108 (griffipavixanthone).
Formula (I)
Table 1.FLBG-1108's
1H with
13C NMR data
Two, the activity of diketone (bixanthone) compounds FLBG-1108
Embodiment 1:
The anti-tumor activity of diketone (bixanthone) compounds FLBG-1108
The present invention adopts the experiment of cell in vitro poison, through detecting the survival rate behind the FLBG-1108 of variable concentrations effect 48h in the isolated culture human cancer cell, measures the anti-tumor activity of compound F 17-hydroxy-corticosterone LBG-1108.
The tumor cell line of choosing has: people's nonsmall-cell lung cancer H520, A549, H549,1299, human liver cancer cell HepG2, human breast cancer cell MCF7, Human Prostate Cancer Cells PC3, LNcaP, DU145, people's colon-cancer cell SW480, HT-2P.Adopt mtt assay (list of references Mosmann T.Rapid colorimetric assay for cellular growth and survival-application to proliferation and cytotoxicity assays.J Immunol Methods; 1983; 65 (1-2), the survival rate (or mortality rate) of 55-63.) measuring every kind of tumor cell is 50% o'clock 503nhibiting concentration IC
50Normal cell selects for use people's kidney epidermis cell HKC-8 to compare.
Under 590nm, measure the OD value in each hole with ELIASA.
Inhibition rate of tumor cell (%)=[1-(dosing group OD value/cell matched group OD value)] * 100%
With the suppression ratio is vertical coordinate, and the logarithm lgC of drug level is the abscissa mapping, calculates IC
50Value.
FLBG-1108 is to the half-inhibition concentration (IC of each tumor cell line
50, μ M) and as shown in table 2.Table 2 data show; Diketone of the present invention (bixanthone) compounds FLBG-1108 has the obvious suppression effect to the propagation of 10 kinds of human cancer cell strains being measured; To human lung carcinoma cell H520, Human Prostate Cancer Cells DU145 and LNCaP, people's colon-cancer cell SW480 and HT-29; Human breast cancer cell MCF-7 has good inhibitory effect, its half-inhibition concentration (IC
50Value) between 2.9～6.7 μ M, and not obvious to the inhibited proliferation of human liver cancer cell HepG2.Select for use the normal kidney epidermis cell of people to measure FLBG-1108 to Normocellular cytotoxicity, the result shows that this chemical compound is to the weak (IC of Normocellular cytotoxicity
50=18.1 μ M), under effective inhibition concentration, normal cell is not shown cytotoxicity, prove that this chemical compound is safety, low toxicity cancerous cell.The MTT active anticancer is the result show, FLBG-1108 is the strongest to human lung carcinoma cell H520 inhibition of proliferation activity, its IC
50Value is 2.9 μ M.
The cell in vitro cytotoxic activity experimental result (IC of table 2:FLBG-1108
50μ M)
Annotate :-expression IC
50＞25 μ M;--expression can't be measured the result, promotes growth of cancer cells.
Embodiment 2
The selectivity cancer suppressing action of diketone (bixanthone) compounds FLBG-1108
Method of testing (MTT) is similar with embodiment 1; Adopt same human cancer cell strain and normal kidney epidermis cell, the administration concentration of FLBG-1108 is set at 3.125,6.25; 12.5 three Concentraton gradient of μ M are with the survival rate of measuring cell behind the various mixing with cells cultivation 48h.
Further adopt three Concentraton gradient (3.125,6.25,12.5 μ M) to measure the selective inhibitory of FLBG-1108 to various cancerous cell, the result is as shown in Figure 1.Diketone (bixanthone) compounds FLBG-1108 is for the human lung carcinoma cell H520 that measures; H549,1299, the propagation of A549 all shows inhibitory action; But human lung carcinoma cell H520 is shown the obvious selectivity inhibitory action; Under three kinds of activities, its suppression ratio strengthens along with the increase of activity gradually, and its inhibition degree obviously is better than the effect to other cancerous cell.
Diketone (bixanthone) compounds FLBG-1108 suppresses the dose-effect relationship of lung carcinoma cell H520 growth
Method is similar with embodiment 1, mainly adopts human lung carcinoma cell line H520 to measure, and administration concentration is set at 0.34,0.78; 1.56,3.12,6.25,12.5; 25.0 seven Concentraton gradient of μ M, medicine and cancerous cell H520 Mixed culture 24h, 48h measures the survival rate of cancerous cell respectively behind the 72h.
The dose-effect relationship of the inhibition lung carcinoma cell H520 growth of FLBG-1108 is as shown in Figure 2; When the result shows diketone (bixanthone) compounds FLBG-1108 to lung carcinoma cell H520 effect 24h; Suppress activity a little less than; And it suppresses active obviously enhancing at effect 48h with after 72h hour, demonstrates good concentration and time-dependent effect.Especially after acting on 48h and 72h, lung carcinoma cell H520 inhibition of proliferation there is good linear relationship.
Embodiment 4
Diketone (bixanthone) compounds FLBG-1108 induces lung carcinoma cell H520 apoptosis
Adopt the two methods of dying of Annexin V-PE/7AAD to measure FLBG-1108 and induce lung carcinoma cell H520 apoptosis.Concrete grammar is: (25cm in H520 cell inoculation to 6 orifice plate that upgrowth situation is good
2), after cell culture spends the night, abandon culture fluid, add the culture fluid that contains variable concentrations (3.12,6.25,12.5 μ M) FLBG-1108 and continue in incubator, to cultivate 24h.Add 0.25% trypsinization liquid peptic cell then; Collect all cells and culture fluid, 4 ℃, centrifugal 5 minutes of 1000rpm; Abandon supernatant; Cell precipitation is resuspended in the 400 μ L buffer (Binding Buffer) (containing Annexin V-PE and 7-AAD), and lucifuge dyeing 15min adopts cells were tested by flow cytometry (FACS cytometry) then.
Explain: Annexin V-PE is the early apoptosis that is used for detecting cell.The cell that is in early apoptosis is dyeed by PE, and behind the entering flow cytometer, painted cell appears at the 4th in the image (Q4) and second (Q2) quadrant.7-AAD is the apoptosis and dead cell in late period that is used for detecting cell.Be in late period apoptosis or dead cell dyeed by 7-AAD, get into flow cytometer after, painted cell appears in the image (Q1) and second (Q2) quadrant of winning.The numeral that each quadrant of flow cytometer image shows is the percent (%) that the cell number that is in this quadrant accounts for all cells.
The two detection apoptosis experimental results of dying of Annexin V-PE/7AAD are as shown in Figure 3; The result proves; Diketone (bixanthone) compounds FLBG-1108 can effectively induce lung carcinoma cell H520 apoptosis; Under three activities, the viable apoptotic cell ratio rises to 11.9% from 4.1% of matched group (not dosing), has increased nearly three times; Late period, the apoptotic cells number was increased to 4.0%, also nearly three times of rising ratio from 1.3%.And the dead cell data do not have obvious variation, 5.5%～5.0%.Proved the apoptosis that FLBG-1108 can effectively induce lung carcinoma cell H520 thus, final anticancer propagation, toxicity is very little.
Embodiment 5
Diketone (bixanthone) compounds FLBG-1108 blocking-up lung carcinoma cell H520 cell cycle
Adopt the two methods of dying of PI/7AAD to measure the influence of FLBG-1108 to lung carcinoma cell H520 cell cycle.Concrete grammar is: (25cm in H520 cell inoculation to 6 orifice plate that upgrowth situation is good
2), after cell culture spends the night, abandon culture fluid, add the culture fluid that contains variable concentrations (3.12,6.25,12.5 μ M) FLBG-1108 and continue in incubator, to cultivate 24h.0.25% trypsinization liquid peptic cell is collected all cells and culture fluid, and 4 ℃, centrifugal 5 minutes of 1000rpm abandons supernatant, and cell precipitation is resuspended among 70% the ice ethanol 500 μ L, and fixed cell spends the night.Centrifugal 4 ℃; 1000rpm; Abandon ethanol liquid, the RNAse that with final concentration is 80 μ g/ml adds the PI that final concentration is 40 μ g/mL (propidium iodide) again at 37 ℃ of following peptic cell 30min; 4 ℃ of lucifuge dyeing 30min adopt flow cytometer (FACS cytometry) to measure the cell number that is in each cell cycle at last.
Explain: RNAse: be a kind of protease, be mainly used in degradation of rna, avoid the PI RNA that when dyeing DNA, also dyes simultaneously, cause the interference of experimental result.PI: be a kind of stain, can combine with the DNA of cell.Flow cytometer is distinguished the residing cell cycle of cell through the dna content that detects cell.
The cell cycle experimental result is as shown in Figure 4, and under three kinds of activities, FLBG-1108 can effectively block the cell cycle of lung carcinoma cell H520 in the S phase.Along with the increase of administration concentration, the cell number ratio of S phase is increased to 27.2% from 20.0%, and the cell number of corresponding G2/M phase then drops to 9.9% from 12.0%, shows that cell cycle significantly is stuck in the S phase.This also is a unexistent characteristic in the present clinical cancer therapy drug, in numerous cancer therapy drugs, belongs to great discovery.
Above embodiment only is used to explain technical scheme of the present invention, but not protection domain of the present invention is limited.
Claims (4)
1. diketone (bixanthone) the compounds FLBG-1108 shown in the formula (I) or its pharmaceutical salts application in the preparation cancer therapy drug
Formula (I).
2. application according to claim 1 is characterized in that, described cancer therapy drug is an anti-lung-cancer medicament.
3. a cancer therapy drug is characterized in that, it contains the diketone as active component (bixanthone) compounds FLBG-1108 or its pharmaceutical salts of effective dose.
4. cancer therapy drug according to claim 3 is characterized in that, this cancer therapy drug is tablet, pill, capsule, granule, solution, suspensoid or Emulsion.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20150038569A1 (en) * | 2013-08-02 | 2015-02-05 | Hong Kong Baptist University | Anti-cervical Cancer Compound and Method of Use Thereof |
| CN105434421A (en) * | 2014-05-29 | 2016-03-30 | 上海中医药大学 | Griffipavixanthone medical application |
-
2011
- 2011-10-28 CN CN2011103335431A patent/CN102440985A/en active Pending
Non-Patent Citations (4)
| Title |
|---|
| MANOSROI J, ET AL: "anti-proliferative activity of extrancts from Thai plants in Guttiferae and Schisandraceae families on human cancer cell lines", 《PHARMACEUTICAL BIOLOGY》 * |
| SHU-GENG CAO, ET AL: "novel cytotoxic polyprenylated xanthonoids from Garcinia gaudichaudii(Guttiferae)", 《TETRAHEDRON》 * |
| SOWEMIMO AA, ET AL: "toxicity and mutagenic activity of some selected nigerian plants", 《JOURNAL OF ETHNOPHARMACOLOGY》 * |
| YUAN-JIAN XU，ET AL.: "griffipavixanthone, a novel cytotoxic bixanthone from Garcinia griffithii and G.pavifolia", 《TETRAHEDRON LETTERS》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20150038569A1 (en) * | 2013-08-02 | 2015-02-05 | Hong Kong Baptist University | Anti-cervical Cancer Compound and Method of Use Thereof |
| US9339488B2 (en) * | 2013-08-02 | 2016-05-17 | Hong Kong Baptist University | Anti-cervical cancer compound and method of use thereof |
| CN105434421A (en) * | 2014-05-29 | 2016-03-30 | 上海中医药大学 | Griffipavixanthone medical application |
| CN105434421B (en) * | 2014-05-29 | 2018-01-05 | 上海中医药大学 | Griffipavixanthone medical usage |
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Application publication date: 20120509 |