CN115282155A - Application of diosgenin derivative in preparation of anti-cancer drugs - Google Patents
Application of diosgenin derivative in preparation of anti-cancer drugs Download PDFInfo
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- CN115282155A CN115282155A CN202210695500.6A CN202210695500A CN115282155A CN 115282155 A CN115282155 A CN 115282155A CN 202210695500 A CN202210695500 A CN 202210695500A CN 115282155 A CN115282155 A CN 115282155A
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- diosgenin
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- cancer drugs
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- WQLVFSAGQJTQCK-VKROHFNGSA-N diosgenin Chemical class O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CC[C@H](O)CC4=CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CO1 WQLVFSAGQJTQCK-VKROHFNGSA-N 0.000 title claims abstract description 27
- 239000002246 antineoplastic agent Substances 0.000 title claims abstract description 7
- 229940041181 antineoplastic drug Drugs 0.000 title claims abstract description 7
- 206010006187 Breast cancer Diseases 0.000 claims description 4
- 208000026310 Breast neoplasm Diseases 0.000 claims description 4
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 4
- 201000005202 lung cancer Diseases 0.000 claims description 4
- 208000020816 lung neoplasm Diseases 0.000 claims description 4
- 206010028980 Neoplasm Diseases 0.000 claims description 3
- AZXZUBZBLNFUPF-CLGLNXEMSA-N chembl1915879 Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CCC(=O)C=C4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CO1 AZXZUBZBLNFUPF-CLGLNXEMSA-N 0.000 claims description 3
- QEGQIJLALWETNE-CLGLNXEMSA-N (25r)-spirosta-1,4-dien-3-one Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)C=CC(=O)C=C4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CO1 QEGQIJLALWETNE-CLGLNXEMSA-N 0.000 claims description 2
- 201000011510 cancer Diseases 0.000 claims description 2
- AZXZUBZBLNFUPF-UHFFFAOYSA-N Tamogenone Natural products CC1C(C2(CCC3C4(C)CCC(=O)C=C4CCC3C2C2)C)C2OC11CCC(C)CO1 AZXZUBZBLNFUPF-UHFFFAOYSA-N 0.000 claims 2
- DWCSNWXARWMZTG-UHFFFAOYSA-N Trigonegenin A Natural products CC1C(C2(CCC3C4(C)CCC(O)C=C4CCC3C2C2)C)C2OC11CCC(C)CO1 DWCSNWXARWMZTG-UHFFFAOYSA-N 0.000 abstract description 10
- WQLVFSAGQJTQCK-UHFFFAOYSA-N diosgenin Natural products CC1C(C2(CCC3C4(C)CCC(O)CC4=CCC3C2C2)C)C2OC11CCC(C)CO1 WQLVFSAGQJTQCK-UHFFFAOYSA-N 0.000 abstract description 10
- 230000000259 anti-tumor effect Effects 0.000 abstract description 6
- 150000001875 compounds Chemical class 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 2
- 238000004113 cell culture Methods 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 235000004360 Dioscorea zingiberensis Nutrition 0.000 description 1
- 241001678283 Dioscorea zingiberensis Species 0.000 description 1
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 1
- 108010019160 Pancreatin Proteins 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000004115 adherent culture Methods 0.000 description 1
- 230000001464 adherent effect Effects 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000036983 biotransformation Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 231100000263 cytotoxicity test Toxicity 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 230000006806 disease prevention Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229940011871 estrogen Drugs 0.000 description 1
- 239000000262 estrogen Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012091 fetal bovine serum Substances 0.000 description 1
- 239000012737 fresh medium Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229940055695 pancreatin Drugs 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- -1 steroid compound Chemical class 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
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Classifications
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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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/14—Drugs for genital or sexual disorders; Contraceptives for lactation disorders, e.g. galactorrhoea
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Reproductive Health (AREA)
- Endocrinology (AREA)
- Pregnancy & Childbirth (AREA)
- Gynecology & Obstetrics (AREA)
- Epidemiology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention discloses an application of diosgenin derivatives in preparing anti-cancer drugs, wherein the diosgenin derivatives are diosgenin or 1-dehydrodiosgenin, and experimental research on a cell level shows that the diosgenin derivatives have a good anti-tumor effect.
Description
Technical Field
The invention belongs to the field of biotransformation and medicine, and relates to an application of diosgenin derivatives in preparing anticancer drugs.
Background
Diosgenin is a natural steroid compound, and mainly exists in rhizome of Dioscorea zingiberensis. In recent years, researchers find that diosgenin and its structural analogs and derivatives have various pharmacological activities, such as anti-tumor effect, estrogen effect, antagonistic effect on rheumatoid arthritis, and the like. However, diosgenin has the problem of low bioavailability, so obtaining diosgenin derivatives through structural modification is an important means for expanding the application range of diosgenin derivatives in disease prevention and treatment. Two diosgenin derivatives, identified as diosgenin and 1-dehydrodiosgenin, are currently obtained in our laboratory by microbial transformation techniques. Regarding the pharmacological activity studies of the above two compounds, at present, only the biological activity of diosgenin against malaria is reported, and 1-dehydrodiosgenin has not been reported yet.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provides the application of the diosgenin derivative in preparing the anti-cancer drugs.
The technical scheme of the invention is summarized as follows:
the use of diosgenin derivatives, which are diosgenin or 1-dehydrodiosgenin, in the preparation of anti-cancer drugs, wherein the diosgenin derivatives have a structure represented by formula I; the structural formula of the 1-dehydrodioscin is shown as a formula II:
the cancer is preferably lung cancer or breast cancer, and may be other cancers.
The invention has the advantages that:
the experimental study of cell level shows that the diosgenin derivative has good anti-tumor effect.
Drawings
Fig. 1 shows cytotoxicity test of diosgenin derivatives according to the present invention.
Detailed Description
Diosgenin (CAS: 512-04-9)
Diosgeninone CAS number: 6870-79-7
1-dehydrodiosgeninone CAS number: 2137-22-6
The present invention is described in further detail below with reference to specific examples. The present invention is not limited by the following examples.
Example 1
Experiments on the antitumor Activity of diosgenin and 1-dehydrodiosgenin.
And (3) cell culture: lung cancer cells (A549) and breast cancer cells (MCF-7) were cultured in DMEM complete medium (containing 10% fetal bovine serum, 100U/mL penicillin and 100U/mL streptomycin) (hereinafter referred to as medium). The conditions of the cell constant temperature incubator are as follows: 5% CO2, 37 ℃. When the cells are cultured until the bottom of the culture bottle is fully paved by 70-80%, the adherent cells are digested by pancreatin. Adding new culture medium after cell centrifugation, re-suspending, diluting, and adjusting density to 3 × 10 4 cells/mL were seeded in 96-well cell culture plates. After 24 hours of adherent culture of the above three cells, the medium was discarded, the fresh medium was replaced, different concentrations of diosgeninone (Compound I) and 1-dehydrodiosgeninone (Compound II) were added, and the culture was continued for 24 hours, and then 20. Mu.L of MTT (5 mg/mL) was added to each well and the culture was continued for 4 hours. Thereafter, the supernatant was removed, and the cells were washed 3 times with PBS, and then 100. Mu.L of DMSO was added to measure the OD value at an absorbance of 490 nm. Each group of 6 replicates. Cell survival (%) = (Ar/As) × 100%, ar is compound-treated group OD value; as: OD value of normal control group.
According to the above results (as shown in fig. 1A, 1B, 1C, and 1D), compound I and compound II have very potent antitumor activities against lung cancer and breast cancer, which show stronger antitumor activities than diosgenin.
Claims (2)
1. The application of diosgenin derivatives in preparing anticancer drugs is characterized in that the diosgenin derivatives are diosgenone or 1-dehydrodiosgenone, and the structure of the diosgenone is shown as formula I; the structural formula of the 1-dehydrodioscin is shown as a formula II:
2. the use according to claim 1, wherein said cancer is lung cancer or breast cancer.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210695500.6A CN115282155A (en) | 2022-06-20 | 2022-06-20 | Application of diosgenin derivative in preparation of anti-cancer drugs |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210695500.6A CN115282155A (en) | 2022-06-20 | 2022-06-20 | Application of diosgenin derivative in preparation of anti-cancer drugs |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN115282155A true CN115282155A (en) | 2022-11-04 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202210695500.6A Pending CN115282155A (en) | 2022-06-20 | 2022-06-20 | Application of diosgenin derivative in preparation of anti-cancer drugs |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN115282155A (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1506051A (en) * | 2002-12-10 | 2004-06-23 | 吉林天药科技股份有限公司 | Antitumor use of diosgenin |
| CN1850849A (en) * | 2006-05-30 | 2006-10-25 | 华东理工大学 | 25-hydroxy dioscin ketone, and its preparing method and use |
| CN102475710A (en) * | 2010-11-24 | 2012-05-30 | 东北师范大学 | Application of diosgenin and derivative thereof for preparing tumor chemotherapy sensitization medicines |
-
2022
- 2022-06-20 CN CN202210695500.6A patent/CN115282155A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1506051A (en) * | 2002-12-10 | 2004-06-23 | 吉林天药科技股份有限公司 | Antitumor use of diosgenin |
| CN1850849A (en) * | 2006-05-30 | 2006-10-25 | 华东理工大学 | 25-hydroxy dioscin ketone, and its preparing method and use |
| CN102475710A (en) * | 2010-11-24 | 2012-05-30 | 东北师范大学 | Application of diosgenin and derivative thereof for preparing tumor chemotherapy sensitization medicines |
Non-Patent Citations (1)
| Title |
|---|
| 陈雪莲;陶欣艺;王玮;王风清;魏东芝;: "薯蓣皂苷元及其维吉尼链霉菌IBL-14转化产物体外抑制人乳腺癌细胞Bcap37的作用研究", 华东理工大学学报(自然科学版), no. 03, pages 360 - 366 * |
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| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20221104 |
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| RJ01 | Rejection of invention patent application after publication |