CN103494793B - 3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene is preparing the application in angiogenesis promoting medicine - Google Patents
3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene is preparing the application in angiogenesis promoting medicine Download PDFInfo
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Abstract
The invention discloses a kind of 3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene is preparing the application in angiogenesis promoting medicine.Wherein 3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene is 40 ~ 80 μMs preparing the valid density applied in angiogenesis promoting medicine.The present invention generates test experience by mice Matrigel vascular embolization in chick chorioallantoic membrane angiogenesis test experience in angiogenesis test experience, body in scuffing migration experiment, extracorporeal blood vessel generation test experience, halfbody and body, sufficient proof 3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene is external in vivo all can Angiogensis effectively.Demonstrate 3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene has very large application and development prospect preparing in Angiogensis and treatment ischemic diseases medicine.
Description
Technical field
The present invention relates to a kind of application of resveratrol methoxy derivatives, especially relate to a kind of 3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene is preparing the application in angiogenesis promoting medicine.
Background technology
3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene structural formula is:
3,4,5,3 ', 4 ', the molecular formula of 5 '-hexa methoxy trans stilbene is C
20h
24o
6, molecular weight is 360.4, and character is off-white color crystalline powder.3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene is also called E-3,4,5,3', 4', 5'-hexa methoxy stilbene.
Resveratrol, chemical name is Resvertrol, belongs to natural polyphenol compounds.Large quantity research confirms: resveratrol has multiple pharmacodynamics effect as effects such as antitumor, defying age, antiinflammatory, nerve and cardiovascular protections.But resveratrol character is unstable, and bioavailability is low, in vivo very easily by metabolism and discharge, limit its pharmacologic activity.In recent years, the many Verakanol derivatives of people's chemosynthesis, research finds that most of Verakanol derivative is all better than resveratrol in stability, pharmacologically active and targeting further.
According to retrieval, there is relevant patent literature about resveratrol and derivant thereof at present.Such as: 1, application number is 201010591625.1, name is called the patent of invention of " new medical use of resveratrol and derivant thereof ", which disclose resveratrol and derivant (RV01 thereof, RV02, RV32) at the novelty teabag of the preparation periphery immunologic hypofunction health food that causes of anti-excessive drinking and pharmaceutical preparations.2, application number is 200610134004.4, name is called the application for a patent for invention of " Verakanol derivative and its production and use ", which disclose respectively with 3,5-dialkoxy-4 '-hydroxy stibene, hydroxy benzaldehyde be that compound (I) prepared by raw material, simple for process.Its pharmaceutically acceptable alkali and officinal salt have good prevention and treatment to various diseases such as tumor, cardiovascular disease, inflammation, its officinal salt, activity is obviously better than resveratrol and Pterostilbene, and salify can improve the stability of resveratrol and Pterostilbene and can improve its pharmacokinetic parameter.3, application number is 201010590982.6, name is called " a kind of Verakanol derivative and its preparation method and application ", which disclose a kind of derivant and 2-pi-allyl-5-[(E)-2-(3-pi-allyl-4-hydroxy phenyl) vinyl] benzene-1,3-diphenol has the architectural feature similar to resveratrol, and its anti-tumor activity is obvious raising compared with resveratrol; Can the growth of inhibition tumor cell significantly, can have a wide range of applications preparing on antitumor drug.
At present, people are to the hexamethyl derivant 3,4,5,3 ', 4 ' of resveratrol, and the research of 5 '-hexa methoxy trans stilbene is still rare.Through authoritative institution's Access point, 3,4,5,3 ', 4 ', the effect of 5 '-hexa methoxy trans stilbene in Angiogensis and relevant pharmacological research thereof are applied, and there is not been reported both at home and abroad at present.
Summary of the invention
The technical problem to be solved in the present invention is: for the deficiencies in the prior art part, and the invention provides a kind of 3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene is preparing the application in angiogenesis promoting medicine.
In order to solve the problem, the technical solution used in the present invention:
The invention provides a kind of 3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene is preparing the application in angiogenesis promoting medicine.
According to above-mentioned 3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene is preparing the application in angiogenesis promoting medicine, and described 3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene is 40 ~ 80 μMs (unit μM refers to a μm ol/L) preparing the valid density applied in angiogenesis promoting medicine.
experiment proves:
Below in conjunction with pharmacological evaluation and the result of 3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene, illustrate 3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene is preparing the effect in angiogenesis promoting medicine.
The preparation of vascular endothelial cell: cultivate vascular endothelial cell in conventional manner, choose growth conditions good and to be in the vascular endothelial cell of exponential phase for subsequent use.
In conjunction with the method for Celluar and Molecular Biology, test as follows, to observe 3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene is on the impact of angiogenesis.
Experiment 1, scuffing migration experiment detection 3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene is on the impact of migration of vascular endothelial cells:
Vascular endothelial cell is inoculated in 24 porocyte culture plates, treats that cell grows to Fusion Strain, at the standardized cut in bottom, center, hole, solvent control group is set: the dimethyl sulfoxide (DMSO) adding 80 μMs processes cell 24 or 48 hours; Experimental group: add 5 ~ 80 μMs 3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene processes cell 24 or 48 hours respectively.With inverted phase contrast microscope observation of cell transition state and computation migration distance.
Experimental result show: 40 ~ 80 μMs 3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene process vascular endothelial cell 24 hours, 10 ~ 80 μMs 3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene process vascular endothelial cell 48 hours, obvious induction of vascular endothelial cell migration.Wherein, 40 ~ 80 μMs 3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene process vascular endothelial cell 48 hours, promotes migration of vascular endothelial cells (referring to attached Fig. 1 and 2) extremely significantly.
Experiment 2, extracorporeal blood vessel generate and detect:
Vascular endothelial cell is inoculated in and is coated with in the 96 porocyte culture plates of Matrigel, after cell attachment, solvent control group is set: the dimethyl sulfoxide (DMSO) adding 80 μMs processes cell 12 hours; Experimental group: add 40 or 80 μMs 3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene processes cell 12 hours respectively.The angiogenesis situation of vascular endothelial cell on Matrigel is observed with inverted phase contrast microscope.Compared with matched group, 3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene significantly promotes that vascular endothelial cell forms the capillary structure of tube chamber shape on Matrigel, and branch point increases.
Experimental result shows: extracorporeal blood vessel generate detect in, 40 or 80 μMs 3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene significantly can promote that vascular endothelial cell becomes blood vessel (referring to accompanying drawing 3).
In experiment 3, halfbody, angiogenesis detects:
Random selecting 6-8 week age Wistar rat, be divided into three groups, often organize 10.Get its thoracic aorta under aseptic condition, be cut into the arterial ring of about 1mm, be positioned over and be coated with in the 96 porocyte culture plates of Matrigel, then wrap by arterial ring with 60 μ LMatrigel.Solvent control group is set: the dimethyl sulfoxide (DMSO) adding 80 μMs processes arterial ring 7 days; Experimental group: add 40 or 80 μMs 3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene processes arterial ring 7 days respectively.Arterial ring new vessels branch situation is observed with inverted phase contrast microscope.Compared with matched group, 3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene significantly increases new vessels number of branches and length around arterial ring.
Experimental result shows: in halfbody angiogenesis detect in, 40 or 80 μMs 3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene significantly can promote arterial ring peripheral vessels new life (referring to accompanying drawing 4).
In experiment 4, body, chick chorioallantoic membrane angiogenesis detects:
Choose the egg of normal fertilization, be divided into three groups, often organize 20.Solvent control group is set: the filter membrane sheet being soaked with 50 μ L, concentration is 80 μMs of DMSO is placed on chick chorioallantoic membrane surface; Experimental group: by being soaked with 50 μ L, concentration is 3,4,5,3 ', 4 ' of 40 μMs or 80 μMs, and the filter membrane sheet of 5 '-hexa methoxy trans stilbene is placed on chick chorioallantoic membrane surface, seals afterwards with Parafilm; Egg is put into 37 DEG C, in the constant incubator of relative humidity 80%, hatch 3 days.After hatching end, there is the chick chorioallantoic membrane 20 minutes of filter membrane by 4% paraformaldehyde fixed placement, observe and take pictures and count.Compared with matched group, load 3,4,5,3 ', 4 ', on the filter membrane sheet of 5 '-hexa methoxy trans stilbene, new vessels is intensive dendroid bifurcated, the multistage minute blood vessel of outside branch.
Experimental result show: in vivo angiogenesis detect in, 40 or 80 μMs 3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene significantly can promote chick chorioallantoic membrane angiogenesis (referring to accompanying drawing 5 and 6).
In experiment 5, body, mice Matrigel vascular embolization generates and detects:
The C57BL/6 mice in 8 week age of random selecting, is divided into three groups, often organizes 10; In 500 μ LMatrigel, add 3,4,5,3 ', 4 ' under 4 DEG C of environment, 5 '-hexa methoxy trans stilbene, make its final concentration be 40 μMs or 80 μMs, be set to experimental group.Choosing final concentration is that the DMSO of 80 μMs is set to matched group.The Matrigel mixed solution that 500 μ L prepare is injected into mice subcutaneous.Normal raising 7 days, takes out the Matrigel thromboembolism that it is subcutaneous, takes pictures.The transparent shape of matched group Matrigel thromboembolism, represents and does not have or extremely a small amount of angiogenesis; And the Matrigel thromboembolism that 40 ~ 80 μMs 3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene adds is in secretly blood red, and include a lot of new vessels.
Experimental result show: in vivo angiogenesis detect in, 40 or 80 μMs 3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene obviously can promote the angiogenesis in mice Matrigel thromboembolism (referring to accompanying drawing 7).
Above-mentioned experimental data statistical procedures:
Result represents with mean+SD.Warp
tinspection,
psignificant difference is considered as during <0.05.
By above-mentioned experiment and result thereof, can draw the following conclusions:
3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene concentration 40 or 80 μMs time, external in vivo all can Angiogensis effectively.Demonstrate 3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene has very large application and development prospect preparing in Angiogensis and treatment ischemic diseases medicine.
Experiment of the present invention and result thereof demonstrate 3,4,5,3 ', 4 ', and 5 '-hexa methoxy trans stilbene promotes there is remarkable effect in angiogenesis drug in preparation, for preparing angiogenesis promoting medicine and novel ischemic diseases drug development provides tempting prospect.
Accompanying drawing explanation
Fig. 1: be solvent control group and 3,4,5 under inverted phase contrast microscope, 3 ', 4 ', the aspect graph of 5 '-hexa methoxy trans stilbene experimental group process migration of vascular endothelial cells after 0,24 and 48 hour.
In Fig. 1: A(0 hour), G(24 hour), M(48 hour) be solvent control group; B(0 hour), H(24 hour), N(48 hour) be 5 μMs 3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene experimental group; C(0 hour), I(24 hour), O(48 hour) be 10 μMs 3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene experimental group; D(0 hour), J(24 hour), P(48 hour) be 20 μMs 3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene experimental group; E(0 hour), K(24 hour), Q(48 hour) be 40 μMs 3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene experimental group; F(0 hour), L(24 hour), R(48 hour) be 80 μMs 3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene experimental group.
Fig. 2: be migration of vascular endothelial cells rate.
Fig. 3: be under inverted phase contrast microscope, in the 96 porocyte culture plates being covered with Matrigel, solvent control group and 3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene experimental group vascular endothelial cell after 12h becomes the aspect graph of blood vessel.
In Fig. 3: A(12 hour) be solvent control group; B(12 hour) be 40 μMs 3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene experimental group; C(12 hour) be 80 μMs 3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene experimental group.
Fig. 4: be under inverted phase contrast microscope, solvent control group and 3,4,5,3 ', 4 ', the aspect graph of 5 '-hexa methoxy trans stilbene experimental group angeogenesis in rat aorta ring.
In Fig. 4: A is solvent control group; B is 40 μMs 3,4,5,3 ', 4 ', and 5 '-hexa methoxy trans stilbene experimental group; C is 80 μMs 3,4,5,3 ', 4 ', and 5 '-hexa methoxy trans stilbene experimental group.
Fig. 5: the solvent control group and 3,4,5 being digital camera shooting, 3 ', 4 ', the chick chorioallantoic membrane of 5 '-hexa methoxy trans stilbene experimental group process, detects the aspect graph of its new vessels.
In Fig. 5: A is solvent control group; B is 40 μMs 3,4,5,3 ', 4 ', and 5 '-hexa methoxy trans stilbene experimental group; C is 80 μMs 3,4,5,3 ', 4 ', and 5 '-hexa methoxy trans stilbene experimental group.
Fig. 6: chick chorioallantoic membrane angiogenesis number statistical figure.
Fig. 7: the solvent control group and 3,4,5 being digital camera shooting, 3 ', 4 ', the subcutaneous Matrigel thromboembolism of mice of 5 '-hexa methoxy trans stilbene experimental group process, observes the aspect graph of wherein new vessels.
In Fig. 7: A is solvent control group; B is 40 μMs 3,4,5,3 ', 4 ', and 5 '-hexa methoxy trans stilbene experimental group; C is 80 μMs 3,4,5,3 ', 4 ', and 5 '-hexa methoxy trans stilbene experimental group.
specific embodiments:
Following examples are only and further illustrate the present invention, do not limit content of the present invention.
Embodiment 1:3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene is preparing the application in angiogenesis promoting medicine:
The preparation of vascular endothelial cell: cultivate vascular endothelial cell in conventional manner, choose growth conditions good and to be in the vascular endothelial cell of exponential phase for subsequent use.
Vascular endothelial cell is inoculated in 24 porocyte culture plates, add 1mLMCDB131 cell culture fluid respectively, treat that cell grows to Fusion Strain, the standardized cut of centre bottom hole, inhale the old culture fluid abandoned in each hole, 1 × PBS(phosphate buffer) clean one time, respectively to adding the DMSO(matched group that concentration is 80 μMs in each hole) and 5, 10, 20, 40, 80 μMs 3, 4, 5, 3 ', 4 ', 5 '-hexa methoxy trans stilbene (experimental group) processes 24 and 48 hours, migration of vascular endothelial cells form is observed and computation migration distance with inverted phase contrast microscope.
Experimental result show: 40 ~ 80 μMs 3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene process vascular endothelial cell 24 hours, 10 ~ 80 μMs 3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene process vascular endothelial cell 48 hours, obvious induction of vascular endothelial cell migration.Wherein, 40 ~ 80 μMs 3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene process vascular endothelial cell 48 hours, promotes migration of vascular endothelial cells (referring to attached Fig. 1 and 2) extremely significantly.
Embodiment 2:3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene promotes the application in angiogenesis drug in preparation:
The preparation of vascular endothelial cell: cultivate vascular endothelial cell in conventional manner, choose growth conditions good and to be in the vascular endothelial cell of exponential phase for subsequent use.
Matrigel not containing somatomedin in 96 porocyte culture plates of 4 DEG C of pre-coolings, every hole adds 30 μ L, plate is placed in 37 DEG C of incubators 1 hour, Matrigel is fully solidified.By vascular endothelial cell with 4 × 10
4density be inoculated in bag by the 96 culture hole Tissue Culture Plates of good Matrigel, be placed in 37 DEG C, CO
21 hour is hatched in incubator.After cell attachment, the every hole of matched group adds the DMSO of 100 μ L concentration 80 μMs, and the every hole of experimental group adds 3,4,5,3 ', 4 ' of 100 μ L concentration 40 μMs or 80 μMs, 5 '-hexa methoxy trans stilbene process 12 hours.The one-tenth blood vessel situation of vascular endothelial cell on Matrigel is observed under inverted phase contrast microscope.
Experimental result shows: during angiogenesis detects in vitro, 40 or 80 μMs 33,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene has significant short vascular endothelial cell and becomes blood vessel function (referring to accompanying drawing 3).
Embodiment 3:3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene promotes the application in angiogenesis drug in preparation:
Matrigel not containing somatomedin in 96 porocyte culture plates of 4 DEG C of pre-coolings, every hole adds 30 μ L, Tissue Culture Plate is placed in 37 DEG C, CO
2incubator 1 hour, makes Matrigel fully solidify.Random selecting 6-8 week age Wistar rat, be divided into three groups, often organize 10.Get its thoracic aorta under aseptic condition, clean up with 1 × PBS, be cut into the arterial ring of about 1mm, be positioned over and be coated with in the 96 porocyte culture plates of Matrigel, then wrap up arterial ring with 60 μ LMatrigel, Tissue Culture Plate is placed in 37 DEG C, CO
2incubator 1 hour, makes Matrigel solidify, fixing arterial ring.The every hole of matched group adds the DMSO of 100 μ L concentration 80 μMs, and the every hole of experimental group adds 3,4,5,3 ', 4 ' of 100 μ L concentration 40 μMs or 80 μMs, the process of 5 '-hexa methoxy trans stilbene, within every two days, changes a fresh medium, coprocessing 7 days.Process terminates rear inverted phase contrast microscope and observes new vessels branch situation around arterial ring.
Experimental result shows: in halfbody angiogenesis detect in, 40 or 80 μMs 3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene significantly can promote arterial ring peripheral vessels new life (referring to accompanying drawing 4).
Embodiment 4:3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene promotes the application in angiogenesis drug in preparation:
Choose the egg of normal fertilization, be divided into three groups, often organize 20.After being sterilized by egg, be placed in 37 DEG C, hatch 4 days in the incubator of relative humidity 80%, between incubation period, tip one end of egg is placed downwards, and by rotational wobble slight for egg several times.After hatching end, a duck eye is opened in the air bag face of egg, eggshell and egg film is carefully peeled off with tweezers, by being soaked with 50 μ L, concentration is the DMSO(solvent control group of 80 μMs) and be soaked with 50 μ L, concentration is 40 μMs or 80 μMs 3,4,5,3 ', the filter membrane sheet of 4 ', 5 '-hexa methoxy trans stilbene (experimental group) is placed on chick chorioallantoic membrane surface, and the position residing for filter membrane is as far as possible away from the one-level trunk of chick chorioallantoic membrane.Seal with Parafilm.Then egg is put into 37 DEG C, the constant incubator of relative humidity 80% hatches 3 days, after hatching end, open air chamber, expose the chick chorioallantoic membrane after process, fix 20 minutes with 4% paraformaldehyde, digital camera is taken pictures and is counted the new vessels on filter membrane sheet.
Experimental result show: in vivo angiogenesis detect in, 40 or 80 μMs 3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene significantly can promote chick chorioallantoic membrane angiogenesis (referring to accompanying drawing 5 and 6).
Embodiment 5:3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene promotes the application in angiogenesis drug in preparation:
The C57BL/6 mice in 8 week age of random selecting, is divided into three groups, often organizes 10.In 500 μ LMatrigel, add 3,4,5,3 ', 4 ' under 4 DEG C of environment, 5 '-hexa methoxy trans stilbene, make its final concentration be 40 μMs or 80 μMs, be set to experimental group.Choosing final concentration is that the DMSO of 80 μMs is set to matched group.With 1ml disposable syringe, the Matrigel mixed solution that 500 μ L prepare is injected into mouse web portion subcutaneous.The Matrigel of injection solidifies in Mice Body.Normal raising mice 7 days, take out the Matrigel thromboembolism that it is subcutaneous, digital camera is taken pictures.
Experimental result show: in vivo angiogenesis detect in, 40 or 80 μMs 3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene significantly can promote the angiogenesis in mice Matrigel thromboembolism (referring to accompanying drawing 7).
Can be proved by experimental conditions and concrete performance, 3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene has significant effect preparing in angiogenesis promoting medicine, 3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene can be applied preparing in angiogenesis promoting medicine.
Claims (1)
1. one kind 3,4,5,3 ', 4 ', 5 '-hexa methoxy trans stilbene is preparing the application in angiogenesis promoting medicine.
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| WO2007002973A2 (en) * | 2005-07-04 | 2007-01-11 | Medizinische Universität Wien | Use of stilbene derivatives for the production of medicaments for the treatment of solid tumours |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2007002973A2 (en) * | 2005-07-04 | 2007-01-11 | Medizinische Universität Wien | Use of stilbene derivatives for the production of medicaments for the treatment of solid tumours |
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| Resveratrol analogues as selective cyclooxygenase-2 inhibitors: synthesis and structure–activity relationship;Marek Murias, et al;《Bioorganic & Medicinal Chemistry》;20040911(第12期);5571–5578 * |
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