CN106749344A - 双黄酮‑铜配合物及其制备方法和应用 - Google Patents
双黄酮‑铜配合物及其制备方法和应用 Download PDFInfo
- Publication number
- CN106749344A CN106749344A CN201710097599.9A CN201710097599A CN106749344A CN 106749344 A CN106749344 A CN 106749344A CN 201710097599 A CN201710097599 A CN 201710097599A CN 106749344 A CN106749344 A CN 106749344A
- Authority
- CN
- China
- Prior art keywords
- biflavone
- ame
- copper complex
- copper
- preparing
- 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.)
- Granted
Links
- -1 Biflavone copper complex Chemical class 0.000 title abstract description 8
- 238000002360 preparation method Methods 0.000 title abstract description 5
- 238000000034 method Methods 0.000 claims abstract description 15
- 230000003064 anti-oxidating effect Effects 0.000 claims abstract description 10
- 239000003814 drug Substances 0.000 claims abstract description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 97
- 239000010949 copper Substances 0.000 claims description 58
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 45
- 239000000243 solution Substances 0.000 claims description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 32
- 238000006243 chemical reaction Methods 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 238000001556 precipitation Methods 0.000 claims description 12
- 150000002500 ions Chemical class 0.000 claims description 10
- UFJORDZSBNSRQT-UHFFFAOYSA-N 3-(4-oxo-2-phenylchromen-3-yl)-2-phenylchromen-4-one Chemical compound O1C2=CC=CC=C2C(=O)C(C=2C(C3=CC=CC=C3OC=2C=2C=CC=CC=2)=O)=C1C1=CC=CC=C1 UFJORDZSBNSRQT-UHFFFAOYSA-N 0.000 claims description 9
- 238000005406 washing Methods 0.000 claims description 9
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 8
- 238000004108 freeze drying Methods 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 claims description 6
- 238000001953 recrystallisation Methods 0.000 claims description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 5
- 229910052802 copper Inorganic materials 0.000 claims description 5
- 229910002651 NO3 Inorganic materials 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 2
- 230000000118 anti-neoplastic effect Effects 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 238000001291 vacuum drying Methods 0.000 claims description 2
- 244000050510 Cunninghamia lanceolata Species 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims 1
- HITDPRAEYNISJU-UHFFFAOYSA-N amenthoflavone Natural products Oc1ccc(cc1)C2=COc3c(C2=O)c(O)cc(O)c3c4cc(ccc4O)C5=COc6cc(O)cc(O)c6C5=O HITDPRAEYNISJU-UHFFFAOYSA-N 0.000 abstract description 21
- HVSKSWBOHPRSBD-UHFFFAOYSA-N amentoflavone Natural products Oc1ccc(cc1)C2=CC(=O)c3c(O)cc(O)c(c3O2)c4cc(ccc4O)C5=COc6cc(O)cc(O)c6C5=O HVSKSWBOHPRSBD-UHFFFAOYSA-N 0.000 abstract description 21
- NQJGJBLOXXIGHL-UHFFFAOYSA-N podocarpusflavone A Natural products COc1ccc(cc1)C2=CC(=O)c3c(O)cc(O)c(c3O2)c4cc(ccc4O)C5=COc6cc(O)cc(O)c6C5=O NQJGJBLOXXIGHL-UHFFFAOYSA-N 0.000 abstract description 21
- YUSWMAULDXZHPY-UHFFFAOYSA-N amentoflavone Chemical compound C1=CC(O)=CC=C1C1=CC(=O)C2=C(O)C=C(O)C(C=3C(=CC=C(C=3)C=3OC4=CC(O)=CC(O)=C4C(=O)C=3)O)=C2O1 YUSWMAULDXZHPY-UHFFFAOYSA-N 0.000 abstract description 17
- 230000000259 anti-tumor effect Effects 0.000 abstract description 17
- 230000000694 effects Effects 0.000 abstract description 16
- OHDRQQURAXLVGJ-HLVWOLMTSA-N azane;(2e)-3-ethyl-2-[(e)-(3-ethyl-6-sulfo-1,3-benzothiazol-2-ylidene)hydrazinylidene]-1,3-benzothiazole-6-sulfonic acid Chemical compound [NH4+].[NH4+].S/1C2=CC(S([O-])(=O)=O)=CC=C2N(CC)C\1=N/N=C1/SC2=CC(S([O-])(=O)=O)=CC=C2N1CC OHDRQQURAXLVGJ-HLVWOLMTSA-N 0.000 abstract description 15
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 abstract description 7
- 238000003556 assay Methods 0.000 abstract description 7
- 230000015572 biosynthetic process Effects 0.000 abstract description 6
- 238000002329 infrared spectrum Methods 0.000 abstract description 4
- 238000007540 photo-reduction reaction Methods 0.000 abstract description 4
- 229910001431 copper ion Inorganic materials 0.000 abstract description 2
- 238000001819 mass spectrum Methods 0.000 abstract description 2
- 150000004699 copper complex Chemical class 0.000 abstract 2
- 238000004847 absorption spectroscopy Methods 0.000 abstract 1
- 210000004027 cell Anatomy 0.000 description 19
- 238000011160 research Methods 0.000 description 12
- 239000000523 sample Substances 0.000 description 11
- REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 description 8
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- 238000005303 weighing Methods 0.000 description 8
- MPTQRFCYZCXJFQ-UHFFFAOYSA-L copper(II) chloride dihydrate Chemical compound O.O.[Cl-].[Cl-].[Cu+2] MPTQRFCYZCXJFQ-UHFFFAOYSA-L 0.000 description 7
- ZVOLCUVKHLEPEV-UHFFFAOYSA-N Quercetagetin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=C(O)C(O)=C(O)C=C2O1 ZVOLCUVKHLEPEV-UHFFFAOYSA-N 0.000 description 5
- HWTZYBCRDDUBJY-UHFFFAOYSA-N Rhynchosin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=CC(O)=C(O)C=C2O1 HWTZYBCRDDUBJY-UHFFFAOYSA-N 0.000 description 5
- 238000002835 absorbance Methods 0.000 description 5
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- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 230000007246 mechanism Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229960001285 quercetin Drugs 0.000 description 5
- 235000005875 quercetin Nutrition 0.000 description 5
- 150000005837 radical ions Chemical class 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 230000002000 scavenging effect Effects 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 108020004414 DNA Proteins 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 230000003078 antioxidant effect Effects 0.000 description 4
- 235000006708 antioxidants Nutrition 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 210000001541 thymus gland Anatomy 0.000 description 4
- 206010008342 Cervix carcinoma Diseases 0.000 description 3
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- 201000010881 cervical cancer Diseases 0.000 description 3
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 description 3
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
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- 230000007704 transition Effects 0.000 description 3
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 2
- 206010006187 Breast cancer Diseases 0.000 description 2
- 208000026310 Breast neoplasm Diseases 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
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- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- SXTLQDJHRPXDSB-UHFFFAOYSA-N copper;dinitrate;trihydrate Chemical compound O.O.O.[Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O SXTLQDJHRPXDSB-UHFFFAOYSA-N 0.000 description 2
- HHEAADYXPMHMCT-UHFFFAOYSA-N dpph Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1[N]N(C=1C=CC=CC=1)C1=CC=CC=C1 HHEAADYXPMHMCT-UHFFFAOYSA-N 0.000 description 2
- 206010073071 hepatocellular carcinoma Diseases 0.000 description 2
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000009830 intercalation Methods 0.000 description 2
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- 238000004949 mass spectrometry Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000002547 new drug Substances 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate group Chemical group [N+](=O)([O-])[O-] NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
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- 239000012224 working solution Substances 0.000 description 2
- 206010005003 Bladder cancer Diseases 0.000 description 1
- SLWXPQIUBGMMGO-UHFFFAOYSA-N C1(=CC=CC=C1)O.C1(=CC=CC=C1)O.C1=CC=CC=C1.C1(=CC=CC=C1)O Chemical group C1(=CC=CC=C1)O.C1(=CC=CC=C1)O.C1=CC=CC=C1.C1(=CC=CC=C1)O SLWXPQIUBGMMGO-UHFFFAOYSA-N 0.000 description 1
- 241000370738 Chlorion Species 0.000 description 1
- 241000218631 Coniferophyta Species 0.000 description 1
- 229910002480 Cu-O Inorganic materials 0.000 description 1
- 230000005778 DNA damage Effects 0.000 description 1
- 231100000277 DNA damage Toxicity 0.000 description 1
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- SQGLUEWZRKIEGS-UHFFFAOYSA-N Ginkgetin Natural products C1=CC(OC)=CC=C1C1=CC(=O)C2=C(O)C=C(OC)C(C=3C(=CC=C(C=3)C=3OC4=CC(O)=CC(O)=C4C(=O)C=3)O)=C2O1 SQGLUEWZRKIEGS-UHFFFAOYSA-N 0.000 description 1
- 235000011201 Ginkgo Nutrition 0.000 description 1
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- 235000008100 Ginkgo biloba Nutrition 0.000 description 1
- 101000741788 Homo sapiens Peroxisome proliferator-activated receptor alpha Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
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- 102000005741 Metalloproteases Human genes 0.000 description 1
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- 241000967211 Selaginella sinensis Species 0.000 description 1
- 241000967218 Selaginella tamariscina Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 description 1
- 102000044209 Tumor Suppressor Genes Human genes 0.000 description 1
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- AZHSSKPUVBVXLK-UHFFFAOYSA-N ethane-1,1-diol Chemical compound CC(O)O AZHSSKPUVBVXLK-UHFFFAOYSA-N 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 210000002950 fibroblast Anatomy 0.000 description 1
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- 235000011949 flavones Nutrition 0.000 description 1
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- AIFCFBUSLAEIBR-UHFFFAOYSA-N ginkgetin Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C(C=1)=CC=C(OC)C=1C1=C(O)C=C(O)C(C(C=2)=O)=C1OC=2C1=CC=C(O)C=C1 AIFCFBUSLAEIBR-UHFFFAOYSA-N 0.000 description 1
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- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 description 1
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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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Toxicology (AREA)
- Biochemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (10)
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201710097599.9A CN106749344B (zh) | 2017-02-22 | 2017-02-22 | 双黄酮-铜配合物及其制备方法和应用 |
US16/487,845 US10815252B2 (en) | 2017-02-22 | 2018-02-13 | Biflavone-copper complex, preparation method and application thereof |
PCT/CN2018/076736 WO2018153330A1 (zh) | 2017-02-22 | 2018-02-13 | 双黄酮-铜配合物及其制备方法和应用 |
Applications Claiming Priority (1)
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CN201710097599.9A CN106749344B (zh) | 2017-02-22 | 2017-02-22 | 双黄酮-铜配合物及其制备方法和应用 |
Publications (2)
Publication Number | Publication Date |
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CN106749344A true CN106749344A (zh) | 2017-05-31 |
CN106749344B CN106749344B (zh) | 2018-12-25 |
Family
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Family Applications (1)
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CN201710097599.9A Expired - Fee Related CN106749344B (zh) | 2017-02-22 | 2017-02-22 | 双黄酮-铜配合物及其制备方法和应用 |
Country Status (3)
Country | Link |
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US (1) | US10815252B2 (zh) |
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Cited By (5)
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CN107698609A (zh) * | 2017-09-15 | 2018-02-16 | 广西师范大学 | 基于人血清白蛋白ib亚域合成抗肿瘤金属前药的方法及应用 |
WO2018153330A1 (zh) * | 2017-02-22 | 2018-08-30 | 南京林业大学 | 双黄酮-铜配合物及其制备方法和应用 |
WO2018153328A1 (zh) * | 2017-02-22 | 2018-08-30 | 南京林业大学 | 双黄酮-铁配合物及其制备方法和应用 |
CN110372768A (zh) * | 2019-07-02 | 2019-10-25 | 华南农业大学 | 地奥司明-铜配合物及其制备方法和应用 |
CN114015068A (zh) * | 2021-11-23 | 2022-02-08 | 中国医学科学院生物医学工程研究所 | 一种基于黄芩素与铜离子配位的花状mof材料及其制备方法和应用 |
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CN113666948B (zh) * | 2021-09-28 | 2023-12-05 | 广西师范大学 | 三联吡啶铜配合物及其合成方法和应用 |
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CN101857583A (zh) * | 2009-04-08 | 2010-10-13 | 温州医学院 | 异黄酮类金属配合物制备方法及抗肿瘤医药用途 |
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WO2018153330A1 (zh) * | 2017-02-22 | 2018-08-30 | 南京林业大学 | 双黄酮-铜配合物及其制备方法和应用 |
WO2018153328A1 (zh) * | 2017-02-22 | 2018-08-30 | 南京林业大学 | 双黄酮-铁配合物及其制备方法和应用 |
US10815252B2 (en) | 2017-02-22 | 2020-10-27 | Nanjing Forestry University | Biflavone-copper complex, preparation method and application thereof |
US10889606B2 (en) | 2017-02-22 | 2021-01-12 | Nanjing Forestry University | Biflavone-iron complex, preparation method and application thereof |
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CN107698609B (zh) * | 2017-09-15 | 2020-01-31 | 广西师范大学 | 基于人血清白蛋白ib亚域合成抗肿瘤金属前药的方法及应用 |
CN110372768A (zh) * | 2019-07-02 | 2019-10-25 | 华南农业大学 | 地奥司明-铜配合物及其制备方法和应用 |
CN110372768B (zh) * | 2019-07-02 | 2021-04-23 | 华南农业大学 | 地奥司明-铜配合物及其制备方法和应用 |
CN114015068A (zh) * | 2021-11-23 | 2022-02-08 | 中国医学科学院生物医学工程研究所 | 一种基于黄芩素与铜离子配位的花状mof材料及其制备方法和应用 |
CN114015068B (zh) * | 2021-11-23 | 2023-02-10 | 中国医学科学院生物医学工程研究所 | 一种基于黄芩素与铜离子配位的花状mof材料及其制备方法和应用 |
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US10815252B2 (en) | 2020-10-27 |
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