CN102861053B - Application of Houttuynoid D in leukemia treating medicine - Google Patents
Application of Houttuynoid D in leukemia treating medicine Download PDFInfo
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- CN102861053B CN102861053B CN201210418103.0A CN201210418103A CN102861053B CN 102861053 B CN102861053 B CN 102861053B CN 201210418103 A CN201210418103 A CN 201210418103A CN 102861053 B CN102861053 B CN 102861053B
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- 239000003814 drug Substances 0.000 title claims abstract description 16
- ROCYDQPSKYPRJK-KXDBBDCJSA-N 2-[3,4-dihydroxy-2-(2-oxoundecyl)phenyl]-5,7-dihydroxy-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one Chemical compound CCCCCCCCCC(=O)CC1=C(O)C(O)=CC=C1C1=C(O[C@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)C(=O)C2=C(O)C=C(O)C=C2O1 ROCYDQPSKYPRJK-KXDBBDCJSA-N 0.000 title abstract description 62
- 150000001875 compounds Chemical class 0.000 claims description 12
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
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- 206010000830 Acute leukaemia Diseases 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical group [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
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- 210000001519 tissue Anatomy 0.000 description 2
- KZDCMKVLEYCGQX-UDPGNSCCSA-N 2-(diethylamino)ethyl 4-aminobenzoate;(2s,5r,6r)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;hydrate Chemical compound O.CCN(CC)CCOC(=O)C1=CC=C(N)C=C1.N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 KZDCMKVLEYCGQX-UDPGNSCCSA-N 0.000 description 1
- 208000036762 Acute promyelocytic leukaemia Diseases 0.000 description 1
- 208000032843 Hemorrhage Diseases 0.000 description 1
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
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- -1 Tetramethyl azo azoles salt Chemical class 0.000 description 1
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- 229960001008 heparin sodium Drugs 0.000 description 1
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- MYFATKRONKHHQL-UHFFFAOYSA-N rhodamine 123 Chemical compound [Cl-].COC(=O)C1=CC=CC=C1C1=C2C=CC(=[NH2+])C=C2OC2=CC(N)=CC=C21 MYFATKRONKHHQL-UHFFFAOYSA-N 0.000 description 1
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention relates to application of Houttuynoid D in a leukemia treating medicine, which belongs to the medicine field. The invention relates to the application of Houttuynoid D in preparing the leukemia treating medicine, application of Houttuynoid D in preparing leukemia cell proliferation inhibiting medicine, and application of Houttuynoid D in preparing a medicine for inducing leukemia cell apoptosis. Houttuynoid D can treat leukemia through inhibiting leukemia cell proliferation and inducing leukemia cell apoptosis. The application of Houttuynoid D in preparing the leukemia treating medicine, which is provided by the invention, is disclosed for the first time, and because the skeleton type belongs to brand-new skeleton type, the inhibiting activity of Houttuynoid D to leukemia cells is extremely strong.
Description
Technical field
The present invention relates to the purposes of Houttuynoid D, relate in particular to the application of Houttuynoid D in preparation treatment leukemia medicament.
Background technology
Acute leukemia is the unusual clone's property malignant disease of a class hematopoietic stem cell.Leukaemia among its clone loses the ability of further differentiation and maturation and is stuck in cytocerastic different phase.The a large amount of hypertrophy of leukaemia are gathered and are soaked into other organs and tissue in bone marrow and other hemopoietic tissue, and normal hematopoiesis is suppressed, clinical manifestation be anemia, hemorrhage, infect and each organ soaks into symptom.According to statistics, leukemia accounts for about 3% of tumor total incidence, is modal a kind of malignant tumor among child and the youth.Leukemic sickness rate is in countries in the world, and Europe and North America sickness rate are the highest, and its mortality rate is 3.2-7.4/10 ten thousand populations.The medicine that searching can prevent and treat acute leukemia seems very urgent.
The compound H outtuynoid D that the present invention relates to is one and delivered (Chen in 2012, S. D. et al., 2012. Houttuynoid D_E, Anti-Herpes Simplex Virus Active Flavonoids with Novel Skeletons from Houttuynia cordata. Organic Letters 14 (7), 1772 – 1775.) new framework compound, this chemical compound has brand-new framework types, present purposes only relates to anti-herpes simplex virus activity (Chen, S. D. et al., 2012. Houttuynoid D_E, Anti-Herpes Simplex Virus Active Flavonoids with Novel Skeletons from Houttuynia cordata. Organic Letters 14 (7), 1772 – 1775.), belong to open first for the purposes in preparation treatment leukemia medicament that the present invention relates to, because framework types belongs to brand-new framework types, and its biological activity for leukaemia's cytotoxicity and apoptosis induction is unexpectedly strong, there is not the possibility that is provided any enlightenment by other chemical compounds, possess outstanding substantive distinguishing features, be used for leukemic control simultaneously and obviously have obvious improvement.
Summary of the invention
The invention provides the application of a kind of Houttuynoid D in the leukemic medicine of preparation treatment, to increase the application of Houttuynoid D in medicine.
The application of Houttuynoid D in the leukemic medicine of preparation treatment.
Houttuynoid D comes leukemia is treated by suppressing leukaemia's (HL-60 cell) propagation and inducing leukemia cell (HL-60 cell) apoptosis.
Described compound H outtuynoid D structure is shown in formula I:
Formula I
The purposes of the Houttuynoid D that the present invention relates in preparation treatment leukemia medicament belongs to open first, and because framework types belongs to brand-new framework types, and its biological activity for leukaemia's cytotoxicity and apoptosis induction is unexpectedly strong, there is not the possibility that is provided any enlightenment by other chemical compounds, possess outstanding substantive distinguishing features, be used for leukemic control simultaneously and obviously have obvious improvement.
The specific embodiment
The preparation method of compound H outtuynoid D involved in the present invention is referring to document (Chen, S. D. et al., 2012. Houttuynoid D_E, Anti-Herpes Simplex Virus Active Flavonoids with Novel Skeletons from Houttuynia cordata. Organic Letters 14 (7), 1772 – 1775.).
The present invention is further detailed explanation by the following examples, but protection scope of the present invention is not subjected to any restriction of specific embodiment, but limited by claim.
Embodiment 1: the preparation of compound H outtuynoid D tablet involved in the present invention:
Get 20 and digest compound Houttuynoid D, add conventional adjuvant 180 grams of preparation tablet, mixing, conventional tablet machine are made 1000.
Embodiment 2: the preparation of compound H outtuynoid D capsule involved in the present invention:
Get 20 and digest compound Houttuynoid D, add conventional adjuvant such as starch 180 grams of preparation capsule, mixing is encapsulatedly made 1000.
Further specify its pharmaceutically active below by pharmacodynamic experiment.
The test example: Houttuynoid D suppresses the HL-60 cell proliferation and induces the HL-60 apoptosis
1 material and method
1.1 material RPMI1640 culture medium is purchased the company in Gibco; Tetramethyl azo azoles salt (MTT), rhodamine 123 are Sigma company product; Caspase-3,9 spectrophotography detection kit are available from the biological company limited of the triumphant base in Nanjing; Other chemical reagent are homemade analytical pure.
1.2 cell culture people promyelocytic leukemia cell strain HL-60 purchases the Shanghai cell biological institute in the Chinese Academy of Sciences, is incubated in the RPMI1640 culture fluid that contains 10% hyclone penicillin 100 kU/L, streptomycin 100 mg/L, 37 ℃, 5%CO
2, to cultivate in the saturated humidity incubator, the trophophase cell of taking the logarithm experimentizes.
1.3 the separation of human peripheral blood single nucleus cell (PBMC)
The healthy donor venous blood of aseptic collection, anticoagulant heparin (every milliliter of whole blood adds the 200U/ml heparin sodium aqua of 0.1ml), PBS etc. times of dilute bloods, 1:4 adds the human lymphocyte separating medium, the centrifugal 20min of 2000 rpm collects serum-free RPMI-1640 culture medium 1500 rpm10min centrifuge washings 2 times of milky white layer back, obtains mononuclearcell, the trypan blue exclusion rate is greater than 95%, is resuspended in the RPMI-1640 culture medium of 10% FCS standby.
1.4 the influence of the HL-60 cell of Houttuynoid D and human PBMC's growth
Inoculation HL-60 cell and human PBMC and 96 orifice plates, every hole 2 * 10
4Individual cell (100ul).37 ℃, 5% CO
2After cultivating 24h under the condition, experimental group once adds the Houttuynoid D of 0.625,1.25,2.5,5.0,10.0 ug/mL, continues to cultivate respectively 24,48, behind the 72h, stops cultivating, and establishes the matched group that only adds culture fluid, and each dosage group is established 4 multiple holes.4h before experiment finishes, every hole adds 20ul MTT solution (5g/L), continue to hatch 4h, stop cultivating, the careful suction abandoned supernatant, every hole adds 150 uL DMSO, concussion 10min selects 570 nm wavelength, measures each hole absorbance (A) value at automatic enzyme connection detector, repeated experiments 3 times, and calculate its growth inhibition ratio (CI).CI=(negative control group A value-experimental group A value)/negative control group A value * 100%.
1.5 flow cytometry is measured apoptosis rate
That collects that 0,2.5,5.0,10.0 ug/mL Houttuynoid D handle 48h respectively organizes cell, PBS washing 2 times, and 70% ethanol that adds pre-cooling is in-20 ℃ of fixing 24h, add 200 uL PI dye liquors behind the centrifuge washing, 50 ul RNA enzymes, 4 ℃ of lucifuges are placed 20 min, the centrifugal 5min of 1500 rpm.Adjusting cell concentration is 1 * 10
5Individual/ml ~ 1 * 10
6Individual/ml, the up flow type cell instrument is analyzed, and excitation source is argon laser, and excitation wavelength is 488 nm.
1.6 this experimental result of statistical analysis applied statistics is analyzed
Software SPSS13.0 handles, and all experimental results adopt x ± s to represent, relatively adopt one factor analysis of variance between group.
2 results
2.1 the influence of the HL-60 cell of Houttuynoid D and PBMC growth
Matched group HL-60 cell active growth, through the Houttuynoid D of 0.625,1.25,2.5,5.0,10.0 ug/mL handle 24,48, behind the 72h, the growth of HL-60 cell is slowing down in various degree all, and be time, concentration dependent.Under same concentrations, cultivate almost unrestraint effect of the 72h human PBMC of Houttuynoid D, with the HL-60 cell significant difference (P＜0.05) (seeing Table 1) is arranged relatively.
The influence of the HL-60 cell proliferation of table 1 Houttuynoid D (x ± s, n=4)
Compare * p＜0.05 * * p＜0.01 with 24h; Compare with 48h
△P＜0.05
△ △P＜0.01; Compare with 72h
▲P＜0.05
▲ ▲P＜0.01
2.2 Flow cytometry HL-60 apoptosis
Behind the Houttuynoid D effect 48h of HL-60 cell and variable concentrations, through flow cytometry analysis, the result shows G
1All occurred the apoptotic hypodiploid of representative peak before the phase peak, along with Houttuynoid D concentration lift-rising height, the HL-60 apoptosis rate raises, wherein 10.0 ug/mL in the finite concentration scope
Houttuynoid D effect 48h apoptosis rate reaches (29.34 ± 2.07) %(table 2).
Behind the table 2 Houttuynoid D effect 48h to the influence of HL-60 apoptosis rate (x ± s, n=3)
Compare * p＜0.05, * * p＜0.01 with negative control group
Conclusion: Houttuynoid D can suppress leukaemia's (HL-60 cell) propagation and inducing leukemia cell (HL-60 cell) apoptosis, therefore, can be used for leukemia is treated.
Claims (1)
1.Houttuynoid the application of D in preparation treatment leukemia medicament, described compound H outtuynoid D structure as
Formula IShown in:
Formula I.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0556720A1 (en) * | 1992-02-14 | 1993-08-25 | Kyowa Hakko Kogyo Co., Ltd. | 5-Aminoflavone derivatives |
| CN1709885A (en) * | 2005-06-07 | 2005-12-21 | 山东大学 | Total flavone glycoside extract of Radix scutellariae, Rodix scutellariae monomer flavone glycoside, its preparation and use |
| CN101137639A (en) * | 2005-03-11 | 2008-03-05 | 霍华德弗洛里生理医学实验研究所 | Flavonoid compounds and uses thereof |
| WO2010112510A1 (en) * | 2009-03-31 | 2010-10-07 | Nestec S.A. | Use of flavonoids to increase the bioavailability of hesperetin |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20120046237A1 (en) * | 1998-04-08 | 2012-02-23 | Theoharides Theoharis C | Compositions for protection against superficial vasodilator flush syndrome, and methods of use |
-
2012
- 2012-10-27 CN CN201210418103.0A patent/CN102861053B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0556720A1 (en) * | 1992-02-14 | 1993-08-25 | Kyowa Hakko Kogyo Co., Ltd. | 5-Aminoflavone derivatives |
| CN101137639A (en) * | 2005-03-11 | 2008-03-05 | 霍华德弗洛里生理医学实验研究所 | Flavonoid compounds and uses thereof |
| CN1709885A (en) * | 2005-06-07 | 2005-12-21 | 山东大学 | Total flavone glycoside extract of Radix scutellariae, Rodix scutellariae monomer flavone glycoside, its preparation and use |
| WO2010112510A1 (en) * | 2009-03-31 | 2010-10-07 | Nestec S.A. | Use of flavonoids to increase the bioavailability of hesperetin |
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