CN107955042A - 具有抗癌活性的铂类配合物、制备方法及应用 - Google Patents
具有抗癌活性的铂类配合物、制备方法及应用 Download PDFInfo
- Publication number
- CN107955042A CN107955042A CN201711182952.XA CN201711182952A CN107955042A CN 107955042 A CN107955042 A CN 107955042A CN 201711182952 A CN201711182952 A CN 201711182952A CN 107955042 A CN107955042 A CN 107955042A
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- Prior art keywords
- platinum
- platinum complexes
- cancer
- antitumor
- antitumor platinum
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- 150000003057 platinum Chemical class 0.000 title claims abstract description 16
- 230000001093 anti-cancer Effects 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 36
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 21
- 230000000259 anti-tumor effect Effects 0.000 claims abstract description 16
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 4
- 229960001756 oxaliplatin Drugs 0.000 claims description 10
- DWAFYCQODLXJNR-BNTLRKBRSA-L oxaliplatin Chemical compound O1C(=O)C(=O)O[Pt]11N[C@@H]2CCCC[C@H]2N1 DWAFYCQODLXJNR-BNTLRKBRSA-L 0.000 claims description 9
- 206010028980 Neoplasm Diseases 0.000 claims description 6
- 201000011510 cancer Diseases 0.000 claims description 6
- 229960004562 carboplatin Drugs 0.000 claims description 5
- 208000010507 Adenocarcinoma of Lung Diseases 0.000 claims description 4
- 190000032366 Miboplatin Chemical compound 0.000 claims description 4
- XJXKGUZINMNEDK-GPJOBVNKSA-L [(4r,5r)-5-(aminomethyl)-2-propan-2-yl-1,3-dioxolan-4-yl]methanamine;platinum(2+);propanedioate Chemical compound [Pt+2].[O-]C(=O)CC([O-])=O.CC(C)C1O[C@H](CN)[C@@H](CN)O1 XJXKGUZINMNEDK-GPJOBVNKSA-L 0.000 claims description 4
- XSMVECZRZBFTIZ-UHFFFAOYSA-M [2-(aminomethyl)cyclobutyl]methanamine;2-oxidopropanoate;platinum(4+) Chemical compound [Pt+4].CC([O-])C([O-])=O.NCC1CCC1CN XSMVECZRZBFTIZ-UHFFFAOYSA-M 0.000 claims description 4
- 229960004316 cisplatin Drugs 0.000 claims description 4
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims description 4
- 229950006835 eptaplatin Drugs 0.000 claims description 4
- 229950008991 lobaplatin Drugs 0.000 claims description 4
- 229950002777 miboplatin Drugs 0.000 claims description 4
- 229950007221 nedaplatin Drugs 0.000 claims description 4
- IIMIOEBMYPRQGU-UHFFFAOYSA-L picoplatin Chemical compound N.[Cl-].[Cl-].[Pt+2].CC1=CC=CC=N1 IIMIOEBMYPRQGU-UHFFFAOYSA-L 0.000 claims description 4
- 229950005566 picoplatin Drugs 0.000 claims description 4
- 206010006187 Breast cancer Diseases 0.000 claims description 3
- 208000026310 Breast neoplasm Diseases 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims description 2
- 201000010881 cervical cancer Diseases 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 210000004907 gland Anatomy 0.000 claims description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 201000007270 liver cancer Diseases 0.000 claims description 2
- 208000014018 liver neoplasm Diseases 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 190000005734 Nedaplatin Chemical compound 0.000 claims 2
- 190000008236 carboplatin Chemical compound 0.000 claims 2
- 210000004027 cell Anatomy 0.000 abstract description 13
- 239000003814 drug Substances 0.000 abstract description 11
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 abstract description 8
- 229940079593 drug Drugs 0.000 abstract description 4
- 229940074391 gallic acid Drugs 0.000 abstract description 4
- 235000004515 gallic acid Nutrition 0.000 abstract description 4
- 230000000118 anti-neoplastic effect Effects 0.000 abstract description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 239000003446 ligand Substances 0.000 abstract 1
- 210000004881 tumor cell Anatomy 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 229940045985 antineoplastic platinum compound Drugs 0.000 description 3
- YAYRGNWWLMLWJE-UHFFFAOYSA-L carboplatin Chemical compound O=C1O[Pt](N)(N)OC(=O)C11CCC1 YAYRGNWWLMLWJE-UHFFFAOYSA-L 0.000 description 3
- -1 hydroxyl oxaliplatin Chemical compound 0.000 description 3
- 150000003058 platinum compounds Chemical class 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 239000002246 antineoplastic agent Substances 0.000 description 2
- 229940041181 antineoplastic drug Drugs 0.000 description 2
- GRHLMSBCOPRFNA-UHFFFAOYSA-M azanide 2-oxidoacetate platinum(4+) Chemical compound N[Pt]1(N)OCC(=O)O1 GRHLMSBCOPRFNA-UHFFFAOYSA-M 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 201000005249 lung adenocarcinoma Diseases 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000011275 oncology therapy Methods 0.000 description 2
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- 206010029350 Neurotoxicity Diseases 0.000 description 1
- 206010033109 Ototoxicity Diseases 0.000 description 1
- 239000012980 RPMI-1640 medium Substances 0.000 description 1
- 235000014220 Rhus chinensis Nutrition 0.000 description 1
- 240000003152 Rhus chinensis Species 0.000 description 1
- 206010044221 Toxic encephalopathy Diseases 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 150000007942 carboxylates Chemical group 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 210000002421 cell wall Anatomy 0.000 description 1
- 208000019065 cervical carcinoma Diseases 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000005034 decoration Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229940000406 drug candidate Drugs 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- PKHMTIRCAFTBDS-UHFFFAOYSA-N hexanoyl hexanoate Chemical compound CCCCCC(=O)OC(=O)CCCCC PKHMTIRCAFTBDS-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 231100000417 nephrotoxicity Toxicity 0.000 description 1
- 231100000228 neurotoxicity Toxicity 0.000 description 1
- 230000007135 neurotoxicity Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- RAFYDKXYXRZODZ-UHFFFAOYSA-N octanoyl octanoate Chemical compound CCCCCCCC(=O)OC(=O)CCCCCCC RAFYDKXYXRZODZ-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229940126701 oral medication Drugs 0.000 description 1
- 231100000262 ototoxicity Toxicity 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0086—Platinum compounds
- C07F15/0093—Platinum compounds without a metal-carbon linkage
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (8)
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CN201711182952.XA CN107955042B (zh) | 2017-11-23 | 2017-11-23 | 具有抗癌活性的铂类配合物、制备方法及应用 |
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CN201711182952.XA CN107955042B (zh) | 2017-11-23 | 2017-11-23 | 具有抗癌活性的铂类配合物、制备方法及应用 |
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CN107955042A true CN107955042A (zh) | 2018-04-24 |
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110950915A (zh) * | 2019-12-24 | 2020-04-03 | 玉林师范学院 | 一种新型大黄酸类-铂(iv)前体抗癌配合物及其合成方法与应用 |
CN111303211A (zh) * | 2018-12-12 | 2020-06-19 | 天津医科大学 | 一种褪黑素-铂(iv)配合物、其制备方法及应用 |
CN111973754A (zh) * | 2019-05-21 | 2020-11-24 | 杭州磐田生物技术有限公司 | 含药物纳米颗粒及其制备方法和应用 |
CN113402565A (zh) * | 2021-06-16 | 2021-09-17 | 中国人民解放军空军军医大学 | 一类含有泊沙康唑的四价铂配合物、制备方法及其应用 |
CN114605475A (zh) * | 2022-02-18 | 2022-06-10 | 昆明贵金属研究所 | 轴向含有3-溴丙酮酸配体的口服Pt(Ⅳ)抗癌前药 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0328274A1 (en) * | 1988-02-02 | 1989-08-16 | Johnson Matthey, Inc., | Pt (IV) complexes |
CN102603805A (zh) * | 2012-02-14 | 2012-07-25 | 昆明贵研药业有限公司 | 具有抗肿瘤活性的铂(ii)配合物及其制备方法 |
CN105622673A (zh) * | 2016-01-25 | 2016-06-01 | 南开大学 | 具有抗癌活性的糖基化四价铂类化合物、制备方法及应用 |
-
2017
- 2017-11-23 CN CN201711182952.XA patent/CN107955042B/zh active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0328274A1 (en) * | 1988-02-02 | 1989-08-16 | Johnson Matthey, Inc., | Pt (IV) complexes |
CN102603805A (zh) * | 2012-02-14 | 2012-07-25 | 昆明贵研药业有限公司 | 具有抗肿瘤活性的铂(ii)配合物及其制备方法 |
CN105622673A (zh) * | 2016-01-25 | 2016-06-01 | 南开大学 | 具有抗癌活性的糖基化四价铂类化合物、制备方法及应用 |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111303211A (zh) * | 2018-12-12 | 2020-06-19 | 天津医科大学 | 一种褪黑素-铂(iv)配合物、其制备方法及应用 |
CN111303211B (zh) * | 2018-12-12 | 2022-08-12 | 天津医科大学 | 一种褪黑素-铂(iv)配合物、其制备方法及应用 |
CN111973754A (zh) * | 2019-05-21 | 2020-11-24 | 杭州磐田生物技术有限公司 | 含药物纳米颗粒及其制备方法和应用 |
CN110950915A (zh) * | 2019-12-24 | 2020-04-03 | 玉林师范学院 | 一种新型大黄酸类-铂(iv)前体抗癌配合物及其合成方法与应用 |
CN110950915B (zh) * | 2019-12-24 | 2022-07-22 | 玉林师范学院 | 一种新型大黄酸类-铂(iv)前体抗癌配合物及其合成方法与应用 |
CN113402565A (zh) * | 2021-06-16 | 2021-09-17 | 中国人民解放军空军军医大学 | 一类含有泊沙康唑的四价铂配合物、制备方法及其应用 |
CN113402565B (zh) * | 2021-06-16 | 2023-07-28 | 中国人民解放军空军军医大学 | 一类含有泊沙康唑的四价铂配合物、制备方法及其应用 |
CN114605475A (zh) * | 2022-02-18 | 2022-06-10 | 昆明贵金属研究所 | 轴向含有3-溴丙酮酸配体的口服Pt(Ⅳ)抗癌前药 |
WO2023155688A1 (zh) * | 2022-02-18 | 2023-08-24 | 云南贵金属实验室有限公司 | 轴向含有3-溴丙酮酸配体的口服Pt(Ⅳ)抗癌前药 |
CN114605475B (zh) * | 2022-02-18 | 2024-02-02 | 云南贵金属实验室有限公司 | 轴向含有3-溴丙酮酸配体的口服Pt(Ⅳ)抗癌前药 |
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