CN108354932A - Applications of the flavone compound GL-V9 in preparing anti-leukemia medicine - Google Patents
Applications of the flavone compound GL-V9 in preparing anti-leukemia medicine Download PDFInfo
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- CN108354932A CN108354932A CN201810374848.9A CN201810374848A CN108354932A CN 108354932 A CN108354932 A CN 108354932A CN 201810374848 A CN201810374848 A CN 201810374848A CN 108354932 A CN108354932 A CN 108354932A
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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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/4025—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil not condensed and containing further heterocyclic rings, e.g. cromakalim
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
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Abstract
The invention belongs to pharmaceutical fields, disclose applications of the flavone compound GL V9 in preparing anti-leukemia medicine.Flavone compound GL V9 have the function of that acute myeloid leukemia cell is induced to dendritic cell to break up, can be used for preparing anti-leukemia medicine.
Description
Technical field
The invention belongs to pharmaceutical fields, are related to applications of the flavone compound GL-V9 in preparing anti-leukemia medicine.
Background technology
Compound GL-V9 is the derivative that structure optimization flavone compound is carried out to wogonin, by the natural products Chinese
Baicalein is synthesized through two-step reaction, first in acetone and K2CO3Reaction condition under pass through 1,4- dibromobutanes replace wogonin
Phenolic hydroxyl group on the positions C7, then the bromine in pyrrolidines substitution previous step product, finally obtains GL-V9.
Early-stage study proves that GL-V9 has extensive antitumor action, including promotes stomach cancer cell MGC -803 and people liver
The apoptosis of cancer cell HepG2, the invasion for inhibiting human breast cancer cell MDA-MB-231 and MCF-7 and transfer improve DSS inductions
Colitis and inhibit the relevant colon cancer of colitis.But without reported in literature its with antileukemie effect.
Invention content
The object of the present invention is to provide applications of the flavone compound GL-V9 in preparing anti-leukemia medicine.
The purpose of the present invention is what is realized by following technical proposal：
Applications of the flavone compound GL-V9 in preparing anti-leukemia medicine.
The leukaemia refers to acute myeloid leukemia.
The anti-leukocythemia refers to that GL-V9 induction acute myeloid leukemia cells (AML) divide to dendritic cell (DC)
Change.
GL-V9 inductions AML can raise the expression of CD83, CD80 and CD86, GL-V9 inductions to DC Differentiations in GL-V9
Phagocytic activity and GL-V9 after the DC differentiation of AML cells promote THP-1 cells to secrete IL-12.
Advantageous effect
The present invention significantly induces acute myeloid leukemia cell it has been investigated that flavone derivative GL-V9 has
(AML) potentiality broken up to dendritic cell (DC).By the form, phenotype and functional experiment of a series of DC, GL-V9's is anti-white
Blood disease acts on, and can be used for preparing anti-leukemia medicine.
Description of the drawings
Fig. 1 is GL-V9 structural formulas.
Fig. 2 is the influence of GL-V9 pairs of 3 kinds of AML cell strain DC sample specific surface antigens CD83/CD80/CD86 expression.
(Fig. 2A, Fig. 2 B, Fig. 2 C correspond to HL-60, U937 and THP-1 respectively)
Fig. 3 is the phagocytic activity after GL-V9 enhancing AML cell strain DC samples differentiation.
Fig. 4 is the secretion of interleukin under the THP-1 cells under GL-V9 effects are co-cultured with T cell.
Specific implementation mode
Effect example 1GL-V9 breaks up AML cell strain DC samples the influence of associated surface antigens
1, experiment material
1.1 reagent
(1)GL-V9(C24H27O5N, molecular weight：409.47) it is provided by China Medicine University, pale yellow powder, purity is more than
99%, using the preceding mother liquor that drug powder is formulated as to 0.02M concentration with dimethyl sulfoxide (DMSO), it is placed in -20 DEG C of preservations.Face use
It is preceding to be made into required concentration with the RPMI-1640 culture solutions containing 10% fetal calf serum.
(2) cell culture reagent
1. culture solution：RPMI-1640 culture mediums are purchased from GIBCO companies of the U.S..RPMI-1640 powder 10.39g is taken to be dissolved in
1000ml sterilizes in tri-distilled water, and 2.0g NaHCO are added3, with 1M hydrochloric acid tune pH value to 7.0, cylindric style filter, which is crossed, to be filtered out
Bacterium, packing, 4 DEG C of refrigerators preserve.Use the streptomysin of the preceding penicillin and 100U/ml that 100U/ml is added.
2. fetal calf serum：U.S.'s GIBCO Products.Inactivate 30min through 56 DEG C of water-baths, dispense and be stored in -20 DEG C it is low
In temperature refrigerator.
3. PBS buffer solution：Weigh NaCl 8.0g, KCl 0.20g, Na2HPO4·H2O 1.56g、KH2PO4 2.0g, it is molten
In 1000ml tri-distilled waters, high pressure sterilization, 4 DEG C of refrigerators preserve.
(3) cell differentiation detects related reagent
The anti-mouse CD83-APC of people, CD80-PE, CD86-FITC antibody is purchased from Miltenyi companies.
Bovine serum albumin(BSA) (Bovine Serum Albumin, BSA) is purchased from Roche companies of Switzerland.
1.2 laboratory apparatus
(1) YJ-875 types Medical purification workbench：Suzhou Decontamination Equipment Plant produces.
(2) 3111 type water-jacket typ CO2Incubator：U.S.'s Thermo electron Products.
(3) electronic balance：Beijing Sai Duolisi instrument systems Co., Ltd product.
(4) QIUJING blood counts version：Chinese Shanghai.
(5) LD4-2 generic centrifuges：Beijing Medical Centrifugal Machine Factory's product.
(6) YG-2000 types cylindric style filter：Satellite Medical Device Works Nv SA of Shaoxin City product.
(7) KY-111 types micro-air compressor：Satellite Medical Device Works Nv SA of Shaoxin City product.
(8) the desk-top high-speed refrigerated centrifuge of 5417R types：German Eppendorf Products.
(9) the pocket test pens of WP types pH：You Te instrument companies of U.S. product.
(10) Research types single track adjustable pipette：German Eppendorf Products.
(11) THZ-312 types Desk type constant-temperatureoscillator oscillator：The upper macro testing equipment Co., Ltd product of Nereid.
(12) flow cytometer：Becton Dickinson companies of the U.S..
1.3 cell strain
Human leukemia cell line U937, HL-60, THP1 are purchased from cell institute of the Shanghai Chinese Academy of Sciences.All cells are with containing
The RPMI1640 culture solution cultures of 100U/ml penicillin, 100mg/ml streptomysins and 10% fetal calf serum.
2, experimental method
Streaming surface antigen detects
As cell breaks up, cell membrane surface protein antigen also accordingly changes, these related eggs with differentiation
It is known as differentiation antigen in vain.It can more accurately judge that whether cell breaks up by detecting cell surface differentiation antigen.
Wherein, CD83 is the mark antigen of dendritic cell differentiation maturation, and CD80/CD86 is costimulating factor.GL-V9 acts on people AML
Cell line is collected cell after being incubated specified time and is counted, and each group cell is adjusted to same density (5 × 105A/ml), with containing
The nonspecific binding site on the PBS buffer solution closing cell surface of 0.5%BSA, is resuspended after centrifugation, and antibody is added, with immune
Fluorescence flow cytometry (FCM) counts the positive cell of fluorescent marker, and processing mode same as the warp of antibody is not added is handled
Cell compare, and make Isotype control.
3, experimental result
By natural products derivative GL-V9 (Fig. 1) in Flow Cytometry Assay different time to three kinds of AML cell lines
The variation of U937, HL-60, THP1 surface antigen.Experimental result shows (Fig. 2A, Fig. 2 B, Fig. 2 C), GL-V9 can raise HL-60,
The expression of the DC maturity symbol object CD83 and its costimulating factor CD80 and CD86 of tri- kinds of cells of U937 and THP-1, at the beginning of the result
Step confirms that the conclusion of DC samples differentiation occurs for GL-V9 induction AML cells.
Effect example 2：The influence of phagocytic activity after GL-V9 breaks up AML cell strain DC samples
1, experiment material
1.1 reagent
(1) drug
GL-V9(C24H27O5N, molecular weight：409.47) it is purchased from China Medicine University, pale yellow powder, purity is more than 99%,
Using the preceding mother liquor that drug powder is formulated as to 0.02M concentration with dimethyl sulfoxide (DMSO), it is placed in -20 DEG C of preservations.It uses before use
RPMI-1640 culture solutions containing 10% fetal calf serum are made into required concentration.
(2) cell culture reagent
Culture solution：RPMI1640 culture mediums are purchased from GIBCO companies of the U.S..RPMI1640 powder 10.39g is taken to be dissolved in
1000ml sterilizes in tri-distilled water, and 2.0g NaHCO are added3, with 1M hydrochloric acid tune pH value to 7.0, cylindric style filter, which is crossed, to be filtered out
Bacterium, packing, 4 DEG C of refrigerators preserve.Use the streptomysin of the preceding penicillin and 100U/ml that 100U/ml is added.
Fetal calf serum：U.S.'s GIBCO Products.30min is inactivated through 56 DEG C of water-baths, dispenses and is stored in -20 DEG C of low temperature
In refrigerator.
PBS buffer solution：Weigh NaCl 8.0g, KCl 0.20g, Na2HPO4·H2O 1.56g、KH2PO42.0g is dissolved in
In 1000ml tri-distilled waters, high pressure sterilization, 4 DEG C of refrigerators preserve.
(3) phagocytosis detection kit is purchased from Cayman companies.
1.2 laboratory apparatus
(1) YJ-875 types Medical purification workbench：Suzhou Decontamination Equipment Plant produces.
(2) 3111 type water-jacket typ CO2Incubator：U.S.'s Thermo electron Products.
(3) electronic balance：Beijing Sai Duolisi instrument systems Co., Ltd product.
(4) QIUJING blood counts version：Chinese Shanghai.
(5) LD4-2 generic centrifuges：Beijing Medical Centrifugal Machine Factory's product.
(6) YG-2000 types cylindric style filter：Satellite Medical Device Works Nv SA of Shaoxin City product.
(7) KY-111 types micro-air compressor：Satellite Medical Device Works Nv SA of Shaoxin City product.
(8) the desk-top high-speed refrigerated centrifuge of 5417R types：German Eppendorf Products.
(9) the pocket test pens of WP types pH：You Te instrument companies of U.S. product.
(10) Research types single track adjustable pipette：German Eppendorf Products.
(11) THZ-312 types Desk type constant-temperatureoscillator oscillator：The upper macro testing equipment Co., Ltd product of Nereid.
(12) flow cytometer：Becton Dickinson companies of the U.S..
1.3 cell strain
Human leukemia cell line U937, HL-60 are purchased from cell institute of the Shanghai Chinese Academy of Sciences.All cells are with containing 100U/
The RPMI1640 culture solution cultures of ml penicillin, 100mg/ml streptomysins and 10% fetal calf serum.
2, experimental method
Phagocytic activity detects
The dendritic cells of early stage have the ability of phagocytosis, GL-V9 can be judged to AML cell DC samples by detecting the ability
Function after differentiation.Gulping down after external GL-V9 induction AML cells DC breaks up is detected as probe using the PE rabbit-IgG marked
Bite ability.After the magnetic bead of the AML cells of in vitro culture and fluorescent marker is incubated specified time altogether, then it is thin with immunofluorescent flow
Born of the same parents measure art (FCM) and detect.
3, experimental result
As shown in figure 3, after GL-V9 effects 96h, the phagocytic activity of AML cell strains U937 and HL-60 significantly improve.Illustrate,
The DC cells that GL-V9 induction AML cell strains are divided into have the functionality of early stage.
Embodiment 3：To the shadow of secretion factor after the DC like cells of GL-V9 induction AML cells generations and T cell co-cultivation
It rings.
1, experiment material
1.1 reagent
(1) drug
GL-V9(C24H27O5N, molecular weight：409.47) it is purchased from China Medicine University, pale yellow powder, purity is more than 99%,
Using the preceding mother liquor that drug powder is formulated as to 0.02M concentration with dimethyl sulfoxide (DMSO), it is placed in -20 DEG C of preservations.It uses before use
RPMI-1640 culture solutions containing 10% fetal calf serum are made into required concentration
(2) cell culture reagent
Culture solution：RPMI-1640 culture mediums are purchased from GIBCO companies of the U.S..RPMI-1640 powder 10.39g is taken to be dissolved in
1000ml sterilizes in tri-distilled water, and 2.0g NaHCO are added3, with 1M hydrochloric acid tune pH value to 7.0, cylindric style filter, which is crossed, to be filtered out
Bacterium, packing, 4 DEG C of refrigerators preserve.Use the streptomysin of the preceding penicillin and 100U/ml that 100U/ml is added.
Fetal calf serum：U.S.'s GIBCO Products.30min is inactivated through 56 DEG C of water-baths, dispenses and is stored in -20 DEG C of low temperature
In refrigerator.
PBS buffer solution：Weigh NaCl 8.0g, KCl 0.20g, Na2HPO4·H2O 1.56g、KH2PO4 2.0g, are dissolved in
In 1000ml tri-distilled waters, high pressure sterilization, 4 DEG C of refrigerators preserve.
(3) lymphocyte separation medium, the brilliant U.S. Products in Nanjing.
(4) CD3-PE immunomagnetic beads are purchased from Miltenyi companies.
(5) IL-2, IL-12ELISA detection kit are purchased from doctor's moral company.
1.2 laboratory apparatus
(1) YJ-875 types Medical purification workbench：Suzhou Decontamination Equipment Plant produces.
(2) 3111 type water-jacket typ CO2Incubator：U.S.'s Thermo electron Products.
(3) electronic balance：Beijing Sai Duolisi instrument systems Co., Ltd product.
(4) LD4-2 generic centrifuges：Beijing Medical Centrifugal Machine Factory's product.
(5) Research types single track adjustable pipette：German Eppendorf Products.
(6) the desk-top high-speed refrigerated centrifuge of 5417R types：German Eppendorf Products.
(7) QIUJING blood cell counting plates：Chinese Shanghai refinement biochemical reagents Instrument Ltd. product.
(8) x-ray biology irradiation instrument：U.S.'s Gulmay Medical Products.
(9) magnetic frame：German Miltenyi companies.
1.3 cell strain
Human leukemia cell line THP-1 is purchased from cell institute of the Shanghai Chinese Academy of Sciences.People's primary T cells are purchased from people from Jiangsu Province
Hematology of people hospital.All cells are with penicillin containing 100U/ml, 100mg/ml streptomysins and 10% fetal calf serum
RPMI1640 culture solution cultures.
2, experimental method
2.1 lymphocyte separation mediums and CD3 immuno magnetic cell separation human T-cells
The density of various cells is different in human peripheral, and human red blood cells density is 1.093, and granulocyte 1.092, lymph is thin
Born of the same parents are 1.074 ± 0.001.The principle of density-gradient centrifugation method is mainly according to the difference of all kinds of haemocyte proportions, using than dense medium
Cell separating liquid between two class cell of Mr. Yu makes the haemocyte of certain weight proportion be distributed by corresponding density gradient centrifugal blood
In different free bands, to achieve the purpose that separation.2ml lymphocyte separation mediums will be added in sterile 10ml centrifuge tubes.
After venous blood in 2ml anticoagulant heparins pipe (or sodium citrate) is mixed well with equivalent serum free medium, with pipettor edge
Tube wall is slowly added dropwise on laminated fluid level, paying attention to keeping clear interface.2000rpm centrifuges 20min.It is divided into three after centrifugation in pipe
Layer has a white cloud and mist narrow band based on mononuclearcell in upper, middle level interface.Mononuclearcell includes lymphocyte
And monocyte.It is inserted into cloud and mist layer with capillary or suction nozzle, draws mononuclearcell.It is subsequently placed in another centrifuge tube.It is added 5
The free serum culture base fluid washing of times volume, turn upside down mixing for several times, and 1500rpm centrifuges 15min.Supernatant is abandoned, repeats and washes
Wash cell 1 time.After final centrifugation, supernatant is abandoned, supernatant exhausts as far as possible.1ml is added and contains 10% calf serum
Cell is resuspended in RPMI1640.Sorting use is carried out to T cell by the PE CD3 magnetic beads marked immediately after cell separator well.
2.2 enzyme-linked immunosorbent assay (ELISA method) detect the secretion that cell co-cultures interleukin in supernatant
Principle：This experiment is based on immunological response, by antigen, the specific reaction of antibody and enzyme to the efficient of substrate
Catalysis reaction is combined.The Avidin of sample, biotinylated antibody, HRP labels is sequentially added into the micropore of coated antibody,
With substrate TMB colour developings after thoroughly washing.TMB converts au bleu under the catalysis of peroxidase, and under the action of an acid
It is converted to final yellow.VEGF contents in the depth and sample of color are proportionate.It is surveyed under 450nm wavelength with microplate reader
Determine absorbance (OD values), calculates sample concentration.
Method：The DC cells that sorting T cell after purification is generated with GL-V9 inductions by designated ratio in 96 orifice plates altogether
After culture 5 days, centrifuging and taking supernatant.Its content is detected with humanized's IL-2 and IL-12ELISA kit of doctor's moral company.
3, experimental result
DC is combined with T cell can largely secrete IL-12, and activation T cell proliferation, induction CTL is generated, and it is immune to dominate TH1 types
Response is conducive to tumor clearance.The secretion level of IL-12 is the important indicator of DC functions.Under DC effects, the CD4+T of activation is thin
Born of the same parents and CD8+T cells can generate IL-2, and the latter is the growth factor of all T cell subgroups, and activating B cell can be promoted to increase
It grows, is the important factor for regulating and controlling immune response, also assists in antibody response, hematopoiesis and oncological surveillance.We are using ELISA experiments point
After not having detected the secretion level of the THP-1 cells IL-12 under GL-V9 effects and being co-cultured with CD3+T cells, T cell
The level of IL-2 is secreted, as shown in figure 4, significant increasing has occurred in the level of the THP-1 cells secretion IL-12 under GL-V9 effects
Add.In the state that THP-1 cells after GL-V9 effects are co-cultured with T cell, the level of IL-2 also goes out in cultivating system
Apparent increase is showed, this is consistent with flow cytometer detection result.
Example of formulations 1
GL-V9 10g are taken, injection (including freeze drying powder injection and aseptic subpackaged dry powder injection) appropriate auxiliary material is added, by note
It penetrates agent (including freeze drying powder injection and aseptic subpackaged dry powder injection) technique and is prepared into injection 1000ml.
Example of formulations 2
GL-V9 10g are taken, tablet (including slow-release tablet, matrix tablet, coating tablet, dispersible tablet etc.) appropriate auxiliary material is added, presses
Tablet (including slow-release tablet, matrix tablet, coating tablet, dispersible tablet etc.) technique prepares piece agent 1000.
Example of formulations 3
GL-V9 10g are taken, the appropriate auxiliary material of capsule is added, capsule 1000 is prepared by capsule technique.
Claims (6)
1. applications of the flavone compound GL-V9 in preparing anti-leukemia medicine.
2. application according to claim 1, it is characterised in that the leukaemia refers to acute myeloid leukemia.
3. application according to claim 1, it is characterised in that the anti-leukocythemia refers to that GL-V9 induction acute myeloids are white
Blood disease cell (AML) breaks up to dendritic cell (DC).
4. application according to claim 3, it is characterised in that GL-V9 induces AML to be raised to DC Differentiations in GL-V9
The expression of CD83, CD80 and CD86.
5. application according to claim 3, it is characterised in that GL-V9 induces AML to be induced to DC Differentiations in GL-V9
Phagocytic activity after the DC differentiation of AML cells.
6. application according to claim 3, it is characterised in that GL-V9 induces AML to promote to DC Differentiations in GL-V9
THP-1 cells secrete IL-12.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201810374848.9A CN108354932A (en) | 2018-04-24 | 2018-04-24 | Applications of the flavone compound GL-V9 in preparing anti-leukemia medicine |
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| CN201810374848.9A CN108354932A (en) | 2018-04-24 | 2018-04-24 | Applications of the flavone compound GL-V9 in preparing anti-leukemia medicine |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112891341A (en) * | 2021-02-07 | 2021-06-04 | 中国药科大学 | Application of GL-V9 and anthracycline antibiotics in preparation of leukemia treatment drug |
| CN113244230A (en) * | 2020-12-21 | 2021-08-13 | 中国药科大学 | Application of GL-V9 in preparation of anti-melanoma drugs |
| CN113786403A (en) * | 2020-12-07 | 2021-12-14 | 中国药科大学 | Application of GL-V9 in preparation of pancreatic cancer inhibition drug |
| CN115785048A (en) * | 2023-01-09 | 2023-03-14 | 山东大学 | GL-V9 crystal form and preparation method thereof |
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| CN101486703A (en) * | 2009-03-03 | 2009-07-22 | 中国药科大学 | Flavone compound with antineoplastic activity, preparation thereof and uses thereof |
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| CN101486703A (en) * | 2009-03-03 | 2009-07-22 | 中国药科大学 | Flavone compound with antineoplastic activity, preparation thereof and uses thereof |
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| YUE ZHAO,ET AL.: "Small molecule GL-V9 protects against colitisassociated colorectal cancer by limiting NLRP3 inflammasome through autophagy", 《ONCOIMMUNOLOGY》 * |
| 主编APOSTOLIA-MARIA TSIMBERIDOU等，主译赵维莅等: "《癌症转化医学研究中的靶向治疗》", 31 July 2017 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113786403A (en) * | 2020-12-07 | 2021-12-14 | 中国药科大学 | Application of GL-V9 in preparation of pancreatic cancer inhibition drug |
| CN113244230A (en) * | 2020-12-21 | 2021-08-13 | 中国药科大学 | Application of GL-V9 in preparation of anti-melanoma drugs |
| CN112891341A (en) * | 2021-02-07 | 2021-06-04 | 中国药科大学 | Application of GL-V9 and anthracycline antibiotics in preparation of leukemia treatment drug |
| CN115785048A (en) * | 2023-01-09 | 2023-03-14 | 山东大学 | GL-V9 crystal form and preparation method thereof |
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