CN116270641A - Application of camptothecine derivatives in preparation of medicines for treating bladder cancer - Google Patents
Application of camptothecine derivatives in preparation of medicines for treating bladder cancer Download PDFInfo
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- CN116270641A CN116270641A CN202310223632.3A CN202310223632A CN116270641A CN 116270641 A CN116270641 A CN 116270641A CN 202310223632 A CN202310223632 A CN 202310223632A CN 116270641 A CN116270641 A CN 116270641A
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- bladder cancer
- camptothecine
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- 206010005003 Bladder cancer Diseases 0.000 title claims abstract description 36
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 title claims abstract description 35
- 201000005112 urinary bladder cancer Diseases 0.000 title claims abstract description 35
- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical class C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 title claims abstract description 22
- 239000003814 drug Substances 0.000 title abstract description 13
- 229940079593 drug Drugs 0.000 title abstract description 10
- 239000002552 dosage form Substances 0.000 claims description 3
- 239000002775 capsule Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 239000008187 granular material Substances 0.000 claims description 2
- 238000002347 injection Methods 0.000 claims description 2
- 239000007924 injection Substances 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000007921 spray Substances 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- 239000003826 tablet Substances 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 3
- 239000003560 cancer drug Substances 0.000 claims 3
- 230000000694 effects Effects 0.000 abstract description 7
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 abstract description 6
- 229960004316 cisplatin Drugs 0.000 abstract description 6
- -1 camptothecine derivative compounds Chemical class 0.000 abstract description 2
- 230000005764 inhibitory process Effects 0.000 abstract description 2
- 230000002147 killing effect Effects 0.000 abstract description 2
- 238000005259 measurement Methods 0.000 abstract description 2
- 210000004027 cell Anatomy 0.000 description 18
- 206010028980 Neoplasm Diseases 0.000 description 6
- 239000012980 RPMI-1640 medium Substances 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 230000003833 cell viability Effects 0.000 description 3
- 238000002512 chemotherapy Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 230000010412 perfusion Effects 0.000 description 3
- IZTQOLKUZKXIRV-YRVFCXMDSA-N sincalide Chemical compound C([C@@H](C(=O)N[C@@H](CCSC)C(=O)NCC(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](N)CC(O)=O)C1=CC=C(OS(O)(=O)=O)C=C1 IZTQOLKUZKXIRV-YRVFCXMDSA-N 0.000 description 3
- 239000012224 working solution Substances 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 108010087230 Sincalide Proteins 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 238000010609 cell counting kit-8 assay Methods 0.000 description 2
- 238000002651 drug therapy Methods 0.000 description 2
- SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 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
- 238000011521 systemic chemotherapy Methods 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 241000759905 Camptotheca acuminata Species 0.000 description 1
- 102000003915 DNA Topoisomerases Human genes 0.000 description 1
- 108090000323 DNA Topoisomerases Proteins 0.000 description 1
- 230000007035 DNA breakage Effects 0.000 description 1
- 230000004543 DNA replication Effects 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
- 239000013543 active substance Substances 0.000 description 1
- 230000006907 apoptotic process Effects 0.000 description 1
- 239000007640 basal medium Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012091 fetal bovine serum Substances 0.000 description 1
- 229960005277 gemcitabine Drugs 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 229960004768 irinotecan Drugs 0.000 description 1
- UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 UWKQSNNFCGGAFS-XIFFEERXSA-N 0.000 description 1
- 230000036210 malignancy Effects 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
- 230000000306 recurrent effect Effects 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 229940126585 therapeutic drug Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 230000005909 tumor killing Effects 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
Classifications
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4745—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
Abstract
The invention discloses a novel pharmaceutical activity of camptothecine derivatives, namely an anti-bladder cancer activity, which is used for preparing a medicament for treating bladder cancer, and belongs to the field of medicines. In particular to the use in bladder cancer treatment. According to the measurement of the pharmaceutical activity in different bladder cancer cells, the result is compared with cisplatin which is a common drug for treating bladder cancer, and the result shows that the half Inhibition Concentration (IC) of 128 camptothecine derivative compounds related to the invention on bladder cancer cells 50 ) Is lower than or close to cisplatin, i.e. the killing ability of the camptothecine derivatives on bladder cancer cells is better than that of the camptothecine derivativesCisplatin or cisplatin-like, so the related camptothecin derivatives have good application prospects in the treatment of bladder cancer.
Description
Technical Field
The invention discloses a novel pharmaceutical activity of camptothecine derivatives, namely an anti-bladder cancer activity, which is used for preparing a medicine for treating bladder cancer, and belongs to the field of medicines.
Background
Bladder cancer is a common malignancy of the urinary system, and due to its highly recurrent nature, drug therapy, particularly chemo-drug therapy, is a particularly important feature in bladder cancer treatment. The chemotherapy of bladder cancer mainly includes bladder perfusion chemotherapy and systemic chemotherapy. The bladder perfusion chemotherapy is mainly used for postoperative bladder perfusion treatment of non-muscular-layer invasive bladder cancer so as to prevent tumor recurrence, but due to tumor heterogeneity, a certain proportion of tumors are insensitive to drugs so as to cause tumor recurrence. The standard therapeutic scheme of the systemic chemotherapy of bladder cancer is a cisplatin+gemcitabine (GC) scheme based on platinum, the overall response rate is 49%, but about half of cases still have unresponsiveness, and aiming at the situation that the sensitivity of different bladder cancer cells to the existing medicines is different, the development and the use of medicines with different action targets are necessary to increase the overall tumor response rate.
The camptothecine derivatives are compounds which are reconstructed based on active alkaloids-camptothecine extracted from the bark of traditional Chinese medicine camptotheca acuminata, have strong anti-tumor activity, and the anti-tumor effect mainly depends on the biological effect of topoisomerase I which is a key enzyme for preventing DNA replication in the nucleus in a ternary complex form, thereby causing the breakage of DNA replication fork and apoptosis. Some camptothecin derivatives represented by Irinotecan are widely used clinically as first-line therapeutic drugs, but are rarely used in bladder cancer at present, and the compounds of the invention have not been used in bladder cancer treatment.
Disclosure of Invention
The invention aims to provide an anti-bladder cancer activity of camptothecine derivatives, which is used for preparing medicines for treating bladder cancer
The anti-bladder cancer activity of 128 camptothecine derivative compounds on bladder cancer cells was specifically studied and analyzed by following experiments for the intervention of bladder cancer T24 and J82 cell lines, using the CCK-8 method to determine the cell viability of different concentrations of the intervening T24 and J82 cells.
The 128 camptothecin derivatives provided by the invention are dissolved and diluted into 10mM mother liquor by DMSO, and are subjected to gradient dilution into 8 mu M, 1.6 mu M, 0.32 mu M, 0.064 mu M, 0.0128 mu M, 0.00256 mu M, 0.000512 mu M, 0.0001024 mu M, 0.00002048 mu M and 0.000004096 mu M working solutions by taking RPMI-1640 complete culture medium as a solvent. Intervention on bladder cancer T24 and J82 cell lines, measurement of cell viability of different concentrations of the intervening T24 and J82 cells using CCK-8 method, calculation of the median Inhibitory Concentration (IC) of each derivative in different cells fitted to the calculation of cell viability 50 ) Value, IC 50 Lower represents less cell survival at the same concentration, i.e., greater killing of tumor cells.
The bladder cancer cell lines T24 and J82 used were each cultured using RPMI-1640 complete medium (RPMI-1640 basal medium, 10% fetal bovine serum, penicillin/streptomycin diabody) at 37℃under 5% carbon dioxide and saturated humidity.
Trypsinizing T24 and J82 cells growing in logarithmic phase and preparing single cell suspension by using RPMI-1640 complete medium, inoculating to 96-well plate at a density of 5000 cells/well after counting, adding 100ul of the working solution/well into the well plate after cell adherence, removing the culture solution after cell adherence, arranging 3 repeated wells in each group, removing the working solution after intervention for 72 hours, adding 100ul of RPMI-1640 basic medium containing 5% cck-8 reagent into each well, continuously culturing for 2 hours, measuring absorbance of each well by using an enzyme-labeled instrument at a wavelength of 450nm, and calculating cell inhibition rate and IC according to absorbance 50 . And compared with cisplatin which is a common drug for treating bladder cancer.
Each compound was tested in triplicate and the values are expressed as mean ± standard deviation. Structural formula of camptothecine derivative and IC in bladder cancer cells 50 See table 1.
TABLE 1 structural formulas of camptothecin derivatives and cisplatin and IC50 data in bladder cancer cells
The experimental results in table 1 show that the half Inhibitory Concentration (IC) of 128 camptothecin derivatives against bladder cancer cells 50 ) The camptothecine derivative has better killing ability to bladder cancer cells than or similar to cisplatin, so that the camptothecine derivative has good application prospect in the treatment of bladder cancer.
Based on the research results, camptothecin derivatives are taken as active substances, and pharmaceutically acceptable carriers and/or auxiliary materials are added according to pharmaceutically acceptable salts to prepare any pharmaceutically acceptable dosage form, such as any dosage form of tablets, sprays, granules, capsules, oral liquid, injection and suspension.
Claims (3)
1. The application of camptothecine derivatives as active ingredients in preparing anti-bladder cancer drugs is characterized in that: the structural formula of the camptothecin derivative is as follows:
2. the use of camptothecin derivatives according to claim 1 as active ingredient in the preparation of anti-bladder cancer drugs, characterized in that: the camptothecin derivative or the pharmaceutically acceptable salt thereof is added with pharmaceutically acceptable carriers and/or auxiliary materials to prepare any pharmaceutically acceptable dosage form.
3. The use of the camptothecine derivatives as claimed in claim 2 as active ingredients in the preparation of anti-bladder cancer drugs, characterized in that: the preparation is any one of tablets, sprays, granules, capsules, oral liquid, injection and suspension.
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311307355.0A CN117045655A (en) | 2023-03-09 | 2023-03-09 | Application of camptothecine derivatives in preparation of medicines for treating bladder cancer |
| CN202311307363.5A CN117462548A (en) | 2023-03-09 | 2023-03-09 | Application of camptothecine derivatives in preparation of medicines for treating bladder cancer |
| CN202311307313.7A CN117281809A (en) | 2023-03-09 | 2023-03-09 | Application of camptothecine derivatives in preparation of medicines for treating bladder cancer |
| CN202311307377.7A CN117599058A (en) | 2023-03-09 | 2023-03-09 | Application of camptothecine derivatives in preparation of medicines for treating bladder cancer |
| CN202311307372.4A CN117982501A (en) | 2023-03-09 | 2023-03-09 | Application of camptothecine derivatives in preparation of medicines for treating bladder cancer |
| CN202310223632.3A CN116270641A (en) | 2023-03-09 | 2023-03-09 | Application of camptothecine derivatives in preparation of medicines for treating bladder cancer |
| CN202311307296.7A CN117224543A (en) | 2023-03-09 | 2023-03-09 | Application of camptothecine derivatives in preparation of medicines for treating bladder cancer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310223632.3A CN116270641A (en) | 2023-03-09 | 2023-03-09 | Application of camptothecine derivatives in preparation of medicines for treating bladder cancer |
Related Child Applications (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202311307377.7A Division CN117599058A (en) | 2023-03-09 | 2023-03-09 | Application of camptothecine derivatives in preparation of medicines for treating bladder cancer |
| CN202311307296.7A Division CN117224543A (en) | 2023-03-09 | 2023-03-09 | Application of camptothecine derivatives in preparation of medicines for treating bladder cancer |
| CN202311307372.4A Division CN117982501A (en) | 2023-03-09 | 2023-03-09 | Application of camptothecine derivatives in preparation of medicines for treating bladder cancer |
| CN202311307363.5A Division CN117462548A (en) | 2023-03-09 | 2023-03-09 | Application of camptothecine derivatives in preparation of medicines for treating bladder cancer |
| CN202311307355.0A Division CN117045655A (en) | 2023-03-09 | 2023-03-09 | Application of camptothecine derivatives in preparation of medicines for treating bladder cancer |
| CN202311307313.7A Division CN117281809A (en) | 2023-03-09 | 2023-03-09 | Application of camptothecine derivatives in preparation of medicines for treating bladder cancer |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN116270641A true CN116270641A (en) | 2023-06-23 |
Family
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Family Applications (7)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202310223632.3A Pending CN116270641A (en) | 2023-03-09 | 2023-03-09 | Application of camptothecine derivatives in preparation of medicines for treating bladder cancer |
| CN202311307372.4A Pending CN117982501A (en) | 2023-03-09 | 2023-03-09 | Application of camptothecine derivatives in preparation of medicines for treating bladder cancer |
| CN202311307377.7A Pending CN117599058A (en) | 2023-03-09 | 2023-03-09 | Application of camptothecine derivatives in preparation of medicines for treating bladder cancer |
| CN202311307313.7A Pending CN117281809A (en) | 2023-03-09 | 2023-03-09 | Application of camptothecine derivatives in preparation of medicines for treating bladder cancer |
| CN202311307296.7A Pending CN117224543A (en) | 2023-03-09 | 2023-03-09 | Application of camptothecine derivatives in preparation of medicines for treating bladder cancer |
| CN202311307355.0A Pending CN117045655A (en) | 2023-03-09 | 2023-03-09 | Application of camptothecine derivatives in preparation of medicines for treating bladder cancer |
| CN202311307363.5A Pending CN117462548A (en) | 2023-03-09 | 2023-03-09 | Application of camptothecine derivatives in preparation of medicines for treating bladder cancer |
Family Applications After (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202311307372.4A Pending CN117982501A (en) | 2023-03-09 | 2023-03-09 | Application of camptothecine derivatives in preparation of medicines for treating bladder cancer |
| CN202311307377.7A Pending CN117599058A (en) | 2023-03-09 | 2023-03-09 | Application of camptothecine derivatives in preparation of medicines for treating bladder cancer |
| CN202311307313.7A Pending CN117281809A (en) | 2023-03-09 | 2023-03-09 | Application of camptothecine derivatives in preparation of medicines for treating bladder cancer |
| CN202311307296.7A Pending CN117224543A (en) | 2023-03-09 | 2023-03-09 | Application of camptothecine derivatives in preparation of medicines for treating bladder cancer |
| CN202311307355.0A Pending CN117045655A (en) | 2023-03-09 | 2023-03-09 | Application of camptothecine derivatives in preparation of medicines for treating bladder cancer |
| CN202311307363.5A Pending CN117462548A (en) | 2023-03-09 | 2023-03-09 | Application of camptothecine derivatives in preparation of medicines for treating bladder cancer |
Country Status (1)
| Country | Link |
|---|---|
| CN (7) | CN116270641A (en) |
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- 2023-03-09 CN CN202310223632.3A patent/CN116270641A/en active Pending
- 2023-03-09 CN CN202311307372.4A patent/CN117982501A/en active Pending
- 2023-03-09 CN CN202311307377.7A patent/CN117599058A/en active Pending
- 2023-03-09 CN CN202311307313.7A patent/CN117281809A/en active Pending
- 2023-03-09 CN CN202311307296.7A patent/CN117224543A/en active Pending
- 2023-03-09 CN CN202311307355.0A patent/CN117045655A/en active Pending
- 2023-03-09 CN CN202311307363.5A patent/CN117462548A/en active Pending
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Also Published As
| Publication number | Publication date |
|---|---|
| CN117462548A (en) | 2024-01-30 |
| CN117599058A (en) | 2024-02-27 |
| CN117224543A (en) | 2023-12-15 |
| CN117281809A (en) | 2023-12-26 |
| CN117982501A (en) | 2024-05-07 |
| CN117045655A (en) | 2023-11-14 |
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