CN109608501A - A kind of cis-platinum probe system, preparation method and application - Google Patents
A kind of cis-platinum probe system, preparation method and application Download PDFInfo
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- CN109608501A CN109608501A CN201811517596.7A CN201811517596A CN109608501A CN 109608501 A CN109608501 A CN 109608501A CN 201811517596 A CN201811517596 A CN 201811517596A CN 109608501 A CN109608501 A CN 109608501A
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 title claims abstract description 60
- 229910052697 platinum Inorganic materials 0.000 title claims abstract description 46
- 239000000523 sample Substances 0.000 title claims abstract description 34
- 238000002360 preparation method Methods 0.000 title claims description 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 29
- 239000002122 magnetic nanoparticle Substances 0.000 claims description 28
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 14
- 239000002105 nanoparticle Substances 0.000 claims description 14
- 125000003368 amide group Chemical group 0.000 claims description 13
- 125000001118 alkylidene group Chemical group 0.000 claims description 12
- 102000004169 proteins and genes Human genes 0.000 claims description 12
- 108090000623 proteins and genes Proteins 0.000 claims description 12
- 238000012650 click reaction Methods 0.000 claims description 9
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 8
- -1 amino Alkane Chemical class 0.000 claims description 8
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 claims description 8
- TZRXHJWUDPFEEY-UHFFFAOYSA-N Pentaerythritol Tetranitrate Chemical compound [O-][N+](=O)OCC(CO[N+]([O-])=O)(CO[N+]([O-])=O)CO[N+]([O-])=O TZRXHJWUDPFEEY-UHFFFAOYSA-N 0.000 claims description 7
- 239000012460 protein solution Substances 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 229940125904 compound 1 Drugs 0.000 claims description 6
- 229940125782 compound 2 Drugs 0.000 claims description 6
- 229940126214 compound 3 Drugs 0.000 claims description 6
- 229940125898 compound 5 Drugs 0.000 claims description 6
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- UYBWIEGTWASWSR-UHFFFAOYSA-N 1,3-diaminopropan-2-ol Chemical compound NCC(O)CN UYBWIEGTWASWSR-UHFFFAOYSA-N 0.000 claims description 4
- 239000012359 Methanesulfonyl chloride Substances 0.000 claims description 4
- 150000001540 azides Chemical class 0.000 claims description 4
- 238000000975 co-precipitation Methods 0.000 claims description 4
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims description 4
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 claims description 3
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000012675 alcoholic extract Substances 0.000 claims description 3
- 238000011938 amidation process Methods 0.000 claims description 3
- 238000010668 complexation reaction Methods 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 238000003328 mesylation reaction Methods 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 239000001294 propane Substances 0.000 claims description 3
- 125000006239 protecting group Chemical group 0.000 claims description 3
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 2
- UORVCLMRJXCDCP-UHFFFAOYSA-N propynoic acid Chemical compound OC(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-N 0.000 claims description 2
- 240000007594 Oryza sativa Species 0.000 claims 1
- 235000007164 Oryza sativa Nutrition 0.000 claims 1
- 235000009566 rice Nutrition 0.000 claims 1
- 102000014914 Carrier Proteins Human genes 0.000 abstract description 5
- 108091008324 binding proteins Proteins 0.000 abstract description 5
- 230000006872 improvement Effects 0.000 abstract description 4
- 239000003814 drug Substances 0.000 abstract description 3
- 230000010534 mechanism of action Effects 0.000 abstract description 3
- 239000002246 antineoplastic agent Substances 0.000 abstract description 2
- 229940041181 antineoplastic drug Drugs 0.000 abstract description 2
- 229940079593 drug Drugs 0.000 abstract description 2
- 229910052751 metal Inorganic materials 0.000 abstract description 2
- 239000002184 metal Substances 0.000 abstract description 2
- 238000011160 research Methods 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 description 23
- 239000000047 product Substances 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 238000012986 modification Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- WTFXARWRTYJXII-UHFFFAOYSA-N iron(2+);iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[Fe+2].[Fe+3].[Fe+3] WTFXARWRTYJXII-UHFFFAOYSA-N 0.000 description 5
- 230000004048 modification Effects 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000002539 nanocarrier Substances 0.000 description 3
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- RTDVRZNXXMNDSC-UHFFFAOYSA-N 2-azidopropan-1-amine Chemical compound NCC(C)N=[N+]=[N-] RTDVRZNXXMNDSC-UHFFFAOYSA-N 0.000 description 2
- WAGMYTXJRVPMGW-UHFFFAOYSA-N 4-azidobutanoic acid Chemical compound OC(=O)CCCN=[N+]=[N-] WAGMYTXJRVPMGW-UHFFFAOYSA-N 0.000 description 2
- 101150075065 Atox1 gene Proteins 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 2
- 229960004316 cisplatin Drugs 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000010183 spectrum analysis Methods 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- 210000004885 white matter Anatomy 0.000 description 2
- VJFMSYZSFUWQPZ-BIPCEHGGSA-N 4-[(r)-[(2s,4s,5r)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-hydroxymethyl]quinolin-6-ol Chemical compound C1=C(O)C=C2C([C@H]([C@H]3N4CC[C@H]([C@H](C4)C=C)C3)O)=CC=NC2=C1 VJFMSYZSFUWQPZ-BIPCEHGGSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 101710153593 Albumin A Proteins 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 238000009010 Bradford assay Methods 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 102100036576 Coiled-coil domain-containing protein 174 Human genes 0.000 description 1
- 102000020856 Copper Transport Proteins Human genes 0.000 description 1
- 108091004554 Copper Transport Proteins Proteins 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 101710196315 High affinity copper uptake protein 1 Proteins 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229910021577 Iron(II) chloride Inorganic materials 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 238000003800 Staudinger reaction Methods 0.000 description 1
- AFCIMSXHQSIHQW-UHFFFAOYSA-N [O].[P] Chemical compound [O].[P] AFCIMSXHQSIHQW-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229940124650 anti-cancer therapies Drugs 0.000 description 1
- 238000011319 anticancer therapy Methods 0.000 description 1
- 230000006907 apoptotic process Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 231100000693 bioaccumulation Toxicity 0.000 description 1
- 238000012742 biochemical analysis Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- VJFMSYZSFUWQPZ-UHFFFAOYSA-N demethyl quinine Natural products C1=C(O)C=C2C(C(C3N4CCC(C(C4)C=C)C3)O)=CC=NC2=C1 VJFMSYZSFUWQPZ-UHFFFAOYSA-N 0.000 description 1
- 150000002012 dioxanes Chemical class 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 238000003810 ethyl acetate extraction Methods 0.000 description 1
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 230000005389 magnetism Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N n-propyl alcohol Natural products CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 230000017260 vegetative to reproductive phase transition of meristem Effects 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/14—Extraction; Separation; Purification
-
- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Analytical Chemistry (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Peptides Or Proteins (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The present invention provides a kind of cis-platinum probe systems, have structure shown in formula I.It is that one kind can obtain the metal probe system for analyzing platinum binding protein group by fast enriching from cell, has pushed the research of platinum binding protein group, be further appreciated that the mechanism of action of platinum-containing anticancer drug, made theoretical basis for drug improvement.
Description
Technical field
The present invention relates to biochemical analysis technical field more particularly to a kind of cis-platinum probe system, preparation method and answer
With.
Background technique
In anti-cancer therapies, chemotherapy is that one kind common are effect treatment means, and wherein platinum medicine is for particular cancer
Disease has good therapeutic effect, such as oophoroma, has obtained extensive research.Then there is disagreement about its mechanism of action, is broadly divided into two
Seed type, a kind of viewpoint thinks can to go directly after cisplatin hydrolysis activation nucleus and Irreversible binding occurs for DNA, destroys its space
Structure causes unrepairable to damage, and leads to Apoptosis；And another viewpoint then thinks the process and egg of cis-platinum generation effect
White matter is related, such as the white CTR1 of copper transport protein.In order to study albumen relevant to cisplatin effect process, platinum binding protein group is
Necessary means.
Summary of the invention
In view of this, the technical problem to be solved in the present invention is that provide a kind of cis-platinum probe system, preparation method with
And application, proteomic assays can be used for by fast enriching albumen from cell.
In order to solve the above technical problems, the present invention provides a kind of cis-platinum probe systems, have structure shown in formula I:
Wherein, M is amido modified magnetic nano-particle, and is connect by imino group with carbonyl.
The present invention is to the type of the magnetic nano-particle and is not particularly limited, preferably magnetic ferric oxide nano particles.
Preferably, the partial size of the nanoparticle is 20~30nm.The partial size of the amido modified magnetic nano-particle
Preferably 100~200nm.
R1For the alkylidene of C1~C5, the more preferably alkylidene of C1~C3, in some embodiments of the invention,
R1For methylene, ethylidene or propylidene.
R2For singly-bound or the alkylidene of C1~C5, the more preferably alkylidene of singly-bound or C1~C3, of the invention some
In specific embodiment, R2For singly-bound, methylene, ethylidene or propylidene.
In some embodiments of the invention, the cis-platinum probe system has structure shown in I-a of formula:
Or structure shown in the formula I can be indicated to flowering structure formula:
Wherein,
Indicate amido modified magnetic nano-particle.
It is above-mentionedOnly schematic diagram, it is amido modified that amino only represents magnetic nano-particle surface, and
Do not represent specific amino number, the present invention for amino quantity and be not particularly limited.
The present invention provides the preparation methods of above-mentioned cis-platinum probe system, comprising the following steps:
Cis-Platinum compound shown in modified magnetic nanoparticle shown in formula II and formula III carries out click-reaction, obtains formula I
Shown cis-platinum probe system；
Wherein, M, R1、R2Range is same as above, and details are not described herein.
Preferably, modified magnetic nanoparticle shown in the formula II is prepared in accordance with the following methods:
A) coprecipitation prepares magnetic nanoparticle；
B) magnetic nanoparticle is modified using ethyl orthosilicate and 3- aminopropyl triethoxysilane, obtains amino
The nanoparticle of modification；
C) amido modified nanoparticle is reacted with C4~C8 acetylenic acid, obtains modified magnetic nanoparticle shown in formula II
Son.
Preferably, cis-Platinum compound shown in the formula III is prepared in accordance with the following methods:
A) amino of 1,3-diamino-2-propanol is protected using di-tert-butyl dicarbonate, obtains compound 1；
B) Mesylation is carried out using alcoholic extract hydroxyl group of the mesyl chloride to compound 1, obtains tertbutyloxycarbonyl protection amino
1,3- diamino -2- methylsulphur propyl propionate, is denoted as compound 2；
C) Azide is carried out to compound 2 using sodium azide, obtains 1, the 3- diamino-of tertbutyloxycarbonyl protection amino
2- azido propane, is denoted as compound 3；
D) the nitrine yl amino of compound 3 is handled, obtains 1, the 3- diamino -2- ammonia of tertbutyloxycarbonyl protection amino
Base propane is denoted as compound 4；
E) compound 4 and C2~C7 nitrine carboxylic acid are subjected to amidation process, obtain the folded of tertbutyloxycarbonyl protection amino
Nitrogen compound is denoted as compound 5；
F) amino protecting group for removing compound 5, obtains compound 6；
G) compound 6 and Pt compound carry out complexation reaction, obtain cis-Platinum compound shown in formula III.
In some embodiments of the invention, work as R1、R2It is ethylidene, i.e., cis-Platinum compound has I-a structure of formula
When, preparation method preferably includes following steps:
Modified magnetic nanoparticle shown in II-a of formula carries out click-reaction with cis-Platinum compound shown in III-a of formula, obtains
Cis-platinum probe system shown in I-a of formula；
Wherein, it is preferred that modified magnetic nanoparticle shown in the II-a of formula is prepared in accordance with the following methods:
A) coprecipitation prepares magnetic nanoparticle；
B) magnetic nanoparticle is modified using ethyl orthosilicate and 3- aminopropyl triethoxysilane, obtains amino
The nanoparticle of modification；
C) amido modified nanoparticle is reacted with pentinoic acid, obtains modified magnetic nanoparticle shown in II-a of formula
Son.
Preferably, cis-Platinum compound shown in the III-a of formula is prepared in accordance with the following methods:
A) amino of 1,3-diamino-2-propanol is protected using di-tert-butyl dicarbonate, obtains compound 1；
B) Mesylation is carried out using alcoholic extract hydroxyl group of the mesyl chloride to compound 1, obtains tertbutyloxycarbonyl protection amino
1,3- diamino -2- methylsulphur propyl propionate, is denoted as compound 2；
C) Azide is carried out to compound 2 using sodium azide, obtains 1, the 3- diamino-of tertbutyloxycarbonyl protection amino
2- azido propane, is denoted as compound 3；
D) the nitrine yl amino of compound 3 is handled, obtains 1, the 3- diamino -2- ammonia of tertbutyloxycarbonyl protection amino
Base propane is denoted as compound 4；
E) compound 4 and nitrine butyric acid are subjected to amidation process, obtain 1, the 3- diamino of tertbutyloxycarbonyl protection amino
Base -2- (4- azido) butyryl propylamine, is denoted as compound 5；
F) amino protecting group for removing compound 5, obtains 1,3- diamino -2- (4- azido) butyryl propylamine, being denoted as
Close object 6；
G) compound 6 and Pt compound carry out complexation reaction, obtain cis-Platinum compound shown in III-a of formula.
The cis-platinum probe body prepared the present invention provides above-mentioned cis-platinum probe system or above-mentioned preparation method ties up to egg with enriched
Application in white.
Above-mentioned cis-platinum probe system can further apply proteomic assays field.
During being enriched with to albumen, the present invention can be first by cis-Platinum compound and protein shown in above-mentioned formula III
Solution mixing, Pt ion and protein binding, are then added modified magnetic nanoparticle shown in formula II, folded with cis-Platinum compound
Nitrogen base carries out click-reaction, and then is enriched with to albumen.
The present invention can also first carry out cis-Platinum compound shown in modified magnetic nanoparticle shown in formula II and formula III
Click-reaction obtains cis-platinum probe system shown in formula I, then mixes with protein solution, be enriched with to albumen.
Specifically, the present invention provides a kind of methods of protein enrichment, comprising the following steps:
Cis-Platinum compound shown in formula III is reacted with protein solution mixing, and modified magnetic shown in formula II is then added
Property nanoparticle, carry out click-reaction with the azido of cis-Platinum compound, and then be enriched with to albumen；
The present invention also provides a kind of methods of protein enrichment, comprising the following steps:
Cis-platinum probe system shown in formula I is reacted with protein solution mixing, is enriched with to albumen；
Wherein, M, R1、R2Range is same as above, and details are not described herein.
In above-mentioned protein solution, albumen can for it is well known to those skilled in the art can with the albumen in conjunction with cis-platinum,
Such as cuprein Atox1, the present invention is to this and is not particularly limited.
Compared with prior art, the present invention provides a kind of cis-platinum probe systems, have structure shown in formula I.It is a kind of energy
Enough fast enrichings from cell obtain the metal probe system of analysis platinum binding protein group, have pushed grinding for platinum binding protein group
Study carefully, be further appreciated that the mechanism of action of platinum-containing anticancer drug, makees theoretical basis for drug improvement.
Detailed description of the invention
Fig. 1 is the hydrogen nuclear magnetic resonance spectrogram for 1, the 3- diamino -2- aminopropane that product IV tertbutyloxycarbonyl protects amino；
Fig. 2 is the infrared absorption pattern of 4- azido butyric acid；
Fig. 3 is the mass spectral analysis map of product VII cis-Platinum compound；
Fig. 4 is the transmission electron microscope picture of superparamag-netic iron oxide；
Fig. 5 is protein-cis-platinum probe-nanoparticle vector compound structural schematic diagram in the present invention.
Specific embodiment
In order to further illustrate the present invention, below with reference to embodiment to cis-platinum probe system provided by the invention, its preparation
Method and application are described in detail.
The preparation of 1 cis-Platinum compound of embodiment
A) 1,3-diamino-2-propanol, di-tert-butyl dicarbonate, potassium carbonate are put into reaction according to mass ratio 1:5:4
In solvent, reaction dissolvent is tetrahydrofuran, water volume ratio 1:1, and reaction condition is normal temperature and pressure stirring 12 hours, after reaction
Three times using isometric ethyl acetate extraction.This reaction is phase transfer reaction, and obtained product I is to be protected by t-butoxycarbonyl
- 2 propyl alcohol of 1,3- diamino.
B) above-mentioned product I is mixed with freshly prepd mesyl chloride according to the mass ratio of the material 1:3 in methylene chloride
Suitable triethylamine is then added in (ice-water bath), and then magneton is stirred to react 4 hours.After reaction, by product saturation food
Salt water washing 2 times, then with 5% sodium bicarbonate solution wash three times, retain lower layer's organic solvent layer (methylene chloride density compared with
Greatly), anhydrous magnesium sulfate is dry, retains filtrate after suction filtration, moves to Rotary Evaporators removal methylene chloride, obtains product
II --- 1, the 3- diamino -2- methylsulphur propyl propionate of tertbutyloxycarbonyl protection amino.
C) above-mentioned product II and sodium azide are added to n,N-Dimethylformamide according to the ratio of the amount 1:1.2 of substance
(DMF) it in, under the conditions of 80 DEG C, is stirred to react 12 hours.After reaction, it is transferred in cold deionized water and stops reaction,
It is extracted in two times with isometric ethyl acetate again, retains upper organic layer.Product is washed twice with saturated salt solution, is used
Anhydrous magnesium sulfate is dry, filters to obtain filtrate after dry, removes solvent with Rotary Evaporators, obtains yellow solid.By yellow solid
It is recrystallized with hexamethylene, obtains 1, the 3- diamino -2- azido propane of product III tertbutyloxycarbonyl protection amino.
D) above-mentioned product III and triphenyl phosphorus are dissolved in four according to the mass ratio of the material 1:1.2 (staudinger reaction)
In hydrogen furans, it is stirred to react under the conditions of 80 DEG C 6 hours.Reaction solution is adjusted to acid (pH is about 4), product is converted into ammonium salt,
With ethyl acetate washing reaction liquid, triphenylphosphine and triphen oxygen phosphorus in reaction solution are removed；Reaction solution is adjusted to alkalinity again, and (pH is about
For 10), product is fully converted to amino state at this time, extraction 2 times is carried out with isometric ethyl acetate, by extract liquor saturation food
Salt water washing 2 times, then be dried with anhydrous magnesium sulfate.Solution after drying is filtered, and is retained filtrate, is used Rotary Evaporators
Solvent is removed, the solid of white, i.e. 1, the 3- diamino -2- aminopropane of product IV tertbutyloxycarbonyl protection amino are obtained.
The hydrogen nuclear magnetic resonance spectrogram of 1, the 3- diamino -2- aminopropane of product IV tertbutyloxycarbonyl protection amino is shown in Fig. 1
It is shown.
E) above-mentioned product IV amide is carried out with freshly prepd nitrine butyric acid to react.Weigh the nitrine butyric acid of 1:7 mass ratio
2 are mixed in methylene chloride (DCM) with 1- (3- dimethylamino-propyl) -3- ethyl-carbodiimide hydrochloride (EDCHCl)
Hour.Above-mentioned product (the ratio between amount of product and nitrine butyric acid substance about 1:1.2) is added in reaction solution, is stirred under room temperature
12 hours.After reaction, reaction solution is washed twice with water, removes EDC.Lower organic layer is done with anhydrous magnesium sulfate
It is dry, filtrate is filtered to obtain after dry, transparent oily liquid is obtained with Rotary Evaporators removal solvent, is obtained in freeze drier white
1,3- diamino -2- (4- azido) butyryl propylamine of color solid, i.e. product V tertbutyloxycarbonyl protection amino.
The infrared absorption pattern of 4- azido butyric acid is as shown in Figure 2.
F) above-mentioned product V removes tertbutyloxycarbonyl protection in dioxanes (dioxane) solution of freshly prepd hydrogen chloride
Base.After reaction, dioxane and the tert-butyl alcohol are removed with Rotary Evaporators, the oily liquids of white is obtained, sufficiently after drying
Obtain white solid, i.e. product VI 1,3- diamino -2- (4- azido) butyryl propylamine.
G) by above-mentioned product VI and Pt (DMSO)2Cl2It is reacted according to the mass ratio of the material 1:1.Reaction process is first by above-mentioned production
Object is dissolved in anhydrous DMF, adds 1,8- diazabicylo, 11 carbon -7- alkene (DBU), is uniformly mixed, is added Pt
(DMSO)2Cl2, then reacted 48 hours under dark condition.After reaction, it is added suitable deionized water, cooling and standings,
Yellow solid is obtained after 24 hours, is washed drying, is obtained product VII cis-Platinum compound, structure is as shown in formula III:
The mass spectral analysis map of above-mentioned cis-Platinum compound is as shown in Figure 3.
The preparation of 2 superparamag-netic iron oxide of embodiment enrichment carrier
A) coprecipitation prepares superparamag-netic iron oxide
Weigh 2.7029g FeCl3·6H2O and 0.9941g FeCl2·4H2O (the ratio between amount of substance 2:1), then in circle
It is dissolved in the flask of bottom with the ethyl alcohol water mixed solution 50mL of 42mL:8mL, yellow mixed solution is warming up to 40 DEG C (constant temperature), used
10mL concentrated ammonia liquor is slowly added dropwise in constant pressure separatory funnel.After ammonium hydroxide completion of dropwise addition, continue to keep reaction 15 minutes, then be warming up to 75
DEG C, heat preservation curing 1 hour.The disperse system finally obtained stands cooling, is washed with water spare.(utilizing magnetic washing)
B) package modification
Superparamag-netic iron oxide prepared by previous step is evenly spread into the molten of 20mL ethanol/water (volume ratio 1:1)
In liquid, with sodium hydroxide and vinegar acid for adjusting pH to 10, purged 10 minutes with nitrogen, be discharged in gas.Disperse system is heated up
It to 85 DEG C, after temperature is constant, is successively slowly added to 500uL ethyl orthosilicate (TEOS), 200uL 3- aminopropyl-triethoxy silicon
Alkane (APTES) keeps high-speed stirred, continues 3 hours of isothermal reaction.After reaction, it is washed with water three times, redisperse to second
It is spare in alcohol.
C) alkynyl in the modification-modification of surface
First by pentinoic acid and EDCHCl in DCM according to 2 hours of the ratio between the amount of substance of 1:1.2 hybrid reaction, then
It is added above-mentioned by amido modified nano particle into DCM, and continues to be stirred to react 24 hours.After reaction, it utilizes
Magnetism separates modified nano particle, and is washed twice with water.
The transmission electron microscope picture of the superparamag-netic iron oxide of preparation is as shown in Figure 4, it can be seen that nano particle is in dispersion
State.
3 click-reaction of embodiment prepares cis-platinum probe system
Cis-Platinum compound prepared by embodiment 1 and modified Nano particle prepared by embodiment 2 are subjected to click-reaction, obtained
Cis-platinum probe system shown in formula I.
Embodiment 4
Known copper albumin A tox1 is that one kind can be with the albumen in conjunction with cis-platinum.It is expressed, is contained with Escherichia coli
The solution of Atox1 albumen, obtaining its concentration with Bradford method measurement is 0.132mg/mL.Cis-platinum prepared by embodiment 1
It closes object to put into protein solution, 37 degree reaction 2 hours lower, adds the alkynyl-modified magnetic nano oxygen of the preparation of embodiment 2
Change iron particle, is added after the completion of monovalence catalysed reaction of copper, nano-carrier is adsorbed on PE tube wall with magnet, then measure egg later
White matter solution, discovery protein concentration is too low (0.003mg/mL), belongs to the magnitude in error range.Therefore, protein is main
It is enriched in cis-platinum probe body to fasten, the bioaccumulation efficiency of protein is greater than 95%.
It is formed by protein-cis-platinum probe-nanoparticle vector compound structural schematic diagram as shown in Figure 5.
As it can be seen that the cis-platinum probe system protein enrichment rate with higher of the application preparation.
As can be seen from the above embodiments, cis-platinum probe system prepared by the present invention protein enrichment rate with higher.
The above description of the embodiment is only used to help understand the method for the present invention and its core ideas.It should be pointed out that pair
For those skilled in the art, without departing from the principle of the present invention, the present invention can also be carried out
Some improvements and modifications, these improvements and modifications also fall within the scope of protection of the claims of the present invention.
Claims (10)
1. a kind of cis-platinum probe system, which is characterized in that have structure shown in formula I:
Wherein, M is amido modified magnetic nano-particle, and is connect by imino group with carbonyl；
R1For the alkylidene of C1~C5；
R2For singly-bound or the alkylidene of C1~C5.
2. cis-platinum probe system according to claim 1, which is characterized in that the cis-platinum probe system has I-a institute of formula
Show structure:
3. cis-platinum probe system according to claim 1, which is characterized in that the magnetic nano-particle is magnetic iron oxide
Nanoparticle.
4. cis-platinum probe system according to claim 1, which is characterized in that the partial size of the magnetic nano-particle be 20~
30nm。
5. the preparation method of the described in any item cis-platinum probe systems of Claims 1 to 4, comprising the following steps:
Cis-Platinum compound shown in modified magnetic nanoparticle shown in formula II and formula III carries out click-reaction, obtains shown in formula I
Cis-platinum probe system；
Wherein, M is amido modified magnetic nano-particle, and is connect by imino group with carbonyl；
R1For the alkylidene of C1~C5；
R2For singly-bound or the alkylidene of C1~C5.
6. preparation method according to claim 5, which is characterized in that modified magnetic nanoparticle shown in the formula II is pressed
It is prepared according to following methods:
A) coprecipitation prepares magnetic nanoparticle；
B) magnetic nanoparticle is modified using ethyl orthosilicate and 3- aminopropyl triethoxysilane, is obtained amido modified
Nanoparticle；
C) amido modified nanoparticle is reacted with C4~C8 acetylenic acid, obtains modified magnetic nanoparticle shown in formula II.
7. preparation method according to claim 5, which is characterized in that cis-Platinum compound shown in the formula III is according to following
Method preparation:
A) amino of 1,3-diamino-2-propanol is protected using di-tert-butyl dicarbonate, obtains compound 1；
B) Mesylation is carried out using alcoholic extract hydroxyl group of the mesyl chloride to compound 1, obtains the 1,3- of tertbutyloxycarbonyl protection amino
Diamino -2- methylsulphur propyl propionate, is denoted as compound 2；
C) Azide is carried out to compound 2 using sodium azide, 1, the 3- diamino -2- for obtaining tertbutyloxycarbonyl protection amino is folded
Nitrogen base propane, is denoted as compound 3；
D) the nitrine yl amino of compound 3 is handled, obtains 1, the 3- diamino -2- aminopropan of tertbutyloxycarbonyl protection amino
Alkane is denoted as compound 4；
E) compound 4 and C2~C7 nitrine carboxylic acid are subjected to amidation process, obtain the Azide of tertbutyloxycarbonyl protection amino
Object is closed, compound 5 is denoted as；
F) amino protecting group for removing compound 5, obtains compound 6；
G) compound 6 and Pt compound carry out complexation reaction, obtain cis-Platinum compound shown in formula III.
8. the described in any item cis-platinum probe systems of Claims 1 to 4 or the described in any item preparation methods of claim 5~7
The cis-platinum probe body of preparation ties up to the application in rich protein.
9. a kind of method of protein enrichment, which comprises the following steps:
Cis-Platinum compound shown in formula III is reacted with protein solution mixing, and modified magnetic shown in formula II is then added and receives
Rice corpuscles carries out click-reaction with the azido of cis-Platinum compound, and then is enriched with to albumen；
Wherein, M is amido modified magnetic nano-particle, and is connect by imino group with carbonyl；
R1For the alkylidene of C1~C5；
R2For singly-bound or the alkylidene of C1~C5.
10. a kind of method of protein enrichment, which comprises the following steps:
Cis-platinum probe system shown in formula I is reacted with protein solution mixing, is enriched with to albumen；
Wherein, M is amido modified magnetic nano-particle, and is connect by imino group with carbonyl；
R1For the alkylidene of C1~C5；
R2For singly-bound or the alkylidene of C1~C5.
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| CN111875611A (en) * | 2020-05-21 | 2020-11-03 | 湖南师范大学 | Fluorescent probe for reduction and activation of anticancer platinum prodrug and preparation method and application thereof |
| CN112094302A (en) * | 2020-11-05 | 2020-12-18 | 江苏申基生物科技有限公司 | Intracellular cisplatin detection probe and preparation method thereof |
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| CN101819838A (en) * | 2010-03-02 | 2010-09-01 | 中国科学院上海应用物理研究所 | Alkynyl-modified magnetic nano-particle module, amino acid compound-modified magnetic nano-particles, preparation method and application thereof |
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| CN111875611A (en) * | 2020-05-21 | 2020-11-03 | 湖南师范大学 | Fluorescent probe for reduction and activation of anticancer platinum prodrug and preparation method and application thereof |
| CN112094302A (en) * | 2020-11-05 | 2020-12-18 | 江苏申基生物科技有限公司 | Intracellular cisplatin detection probe and preparation method thereof |
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