CN106588996B - 酞菁芳基钌配合物及其制备方法和用途 - Google Patents
酞菁芳基钌配合物及其制备方法和用途 Download PDFInfo
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- CN106588996B CN106588996B CN201610950339.7A CN201610950339A CN106588996B CN 106588996 B CN106588996 B CN 106588996B CN 201610950339 A CN201610950339 A CN 201610950339A CN 106588996 B CN106588996 B CN 106588996B
- Authority
- CN
- China
- Prior art keywords
- phthalocyanine
- compound
- formula
- aryl ruthenium
- ruthenium complex
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000012327 Ruthenium complex Substances 0.000 title claims abstract description 22
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229960000935 dehydrated alcohol Drugs 0.000 claims abstract description 12
- YKFLAYDHMOASIY-UHFFFAOYSA-N γ-terpinene Chemical compound CC(C)C1=CCC(C)=CC1 YKFLAYDHMOASIY-UHFFFAOYSA-N 0.000 claims abstract description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000010992 reflux Methods 0.000 claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 7
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims abstract description 6
- 229910000024 caesium carbonate Inorganic materials 0.000 claims abstract description 6
- 239000013078 crystal Substances 0.000 claims abstract description 5
- 229910019891 RuCl3 Inorganic materials 0.000 claims abstract description 3
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 claims abstract description 3
- 229910009112 xH2O Inorganic materials 0.000 claims abstract description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims description 5
- 238000001556 precipitation Methods 0.000 claims description 5
- 229910052707 ruthenium Inorganic materials 0.000 claims description 5
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- -1 phthalocyanine aryl ruthenium complexes Chemical class 0.000 abstract description 10
- 230000008020 evaporation Effects 0.000 abstract 1
- 238000001704 evaporation Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 6
- 206010028980 Neoplasm Diseases 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- 201000011510 cancer Diseases 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 230000000259 anti-tumor effect Effects 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 206010034133 Pathogen resistance Diseases 0.000 description 2
- 206010034972 Photosensitivity reaction Diseases 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 208000007578 phototoxic dermatitis Diseases 0.000 description 2
- 231100000018 phototoxicity Toxicity 0.000 description 2
- 150000004032 porphyrins Chemical class 0.000 description 2
- 210000004881 tumor cell Anatomy 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 102000002322 Egg Proteins Human genes 0.000 description 1
- 108010000912 Egg Proteins Proteins 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 206010033128 Ovarian cancer Diseases 0.000 description 1
- 206010061535 Ovarian neoplasm Diseases 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000000118 anti-neoplastic effect Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000002895 emetic Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 231100000417 nephrotoxicity Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 210000004681 ovum Anatomy 0.000 description 1
- 210000000578 peripheral nerve Anatomy 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- C07F15/0046—Ruthenium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Abstract
Description
细胞株 | A2780(避光) | A2780(光照) |
IC<sub>50</sub>(μmol/mL) | 7.3±1.1 | 1.3±0.2 |
Claims (6)
Priority Applications (1)
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CN201610950339.7A CN106588996B (zh) | 2016-10-26 | 2016-10-26 | 酞菁芳基钌配合物及其制备方法和用途 |
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CN201610950339.7A CN106588996B (zh) | 2016-10-26 | 2016-10-26 | 酞菁芳基钌配合物及其制备方法和用途 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN106588996A CN106588996A (zh) | 2017-04-26 |
CN106588996B true CN106588996B (zh) | 2019-02-22 |
Family
ID=58589634
Family Applications (1)
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CN201610950339.7A Active CN106588996B (zh) | 2016-10-26 | 2016-10-26 | 酞菁芳基钌配合物及其制备方法和用途 |
Country Status (1)
Country | Link |
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CN (1) | CN106588996B (zh) |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008090526A1 (en) * | 2007-01-26 | 2008-07-31 | Universite De Neuchatel | Organometallic compounds |
CN101851256A (zh) * | 2010-04-30 | 2010-10-06 | 广东药学院 | 一种以柔性碳链联接的钌(ⅱ)卟啉配合物及其制备方法和应用 |
-
2016
- 2016-10-26 CN CN201610950339.7A patent/CN106588996B/zh active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008090526A1 (en) * | 2007-01-26 | 2008-07-31 | Universite De Neuchatel | Organometallic compounds |
CN101851256A (zh) * | 2010-04-30 | 2010-10-06 | 广东药学院 | 一种以柔性碳链联接的钌(ⅱ)卟啉配合物及其制备方法和应用 |
Non-Patent Citations (1)
Title |
---|
Tagging (Arene)ruthenium(II) Anticancer Complexes with Fluorescent Labels;Fabio Zobi et al;《Eur. J. Inorg. Chem.》;20070503;第2783-2796页 |
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CN106588996A (zh) | 2017-04-26 |
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Address after: Mingxiu Road East of Nanning city the Guangxi Zhuang Autonomous Region 530001 Guangxi Teachers Education University No. 175 Patentee after: NANNING NORMAL University Address before: Mingxiu Road East of Nanning city the Guangxi Zhuang Autonomous Region 530001 Guangxi Teachers Education University No. 175 Patentee before: Guangxi Normal University |
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Effective date of registration: 20191118 Address after: 210000 No.1, Xiushan Middle Road, Lishui Economic Development Zone, Nanjing City, Jiangsu Province Patentee after: NANJING ADVANCED BIOMATERIALS AND PROCESS EQUIPMENT RESEARCH INSTITUTE Co.,Ltd. Address before: Mingxiu Road East of Nanning city the Guangxi Zhuang Autonomous Region 530001 Guangxi Teachers Education University No. 175 Patentee before: Nanning Normal University |
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