CN108498483A - 一种pH/还原响应性聚氨基酸两性离子纳米颗粒的制备方法 - Google Patents
一种pH/还原响应性聚氨基酸两性离子纳米颗粒的制备方法 Download PDFInfo
- Publication number
- CN108498483A CN108498483A CN201810432125.XA CN201810432125A CN108498483A CN 108498483 A CN108498483 A CN 108498483A CN 201810432125 A CN201810432125 A CN 201810432125A CN 108498483 A CN108498483 A CN 108498483A
- Authority
- CN
- China
- Prior art keywords
- amphoteric ion
- nano particle
- polyaminoacid
- benzyl
- cystamine
- 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
- 239000002105 nanoparticle Substances 0.000 title claims abstract description 61
- 230000004044 response Effects 0.000 title claims abstract description 33
- 229920001308 poly(aminoacid) Polymers 0.000 title claims abstract description 22
- 230000009467 reduction Effects 0.000 title claims abstract description 22
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 229920000642 polymer Polymers 0.000 claims abstract description 16
- 239000004472 Lysine Substances 0.000 claims abstract description 15
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims abstract description 12
- 150000001412 amines Chemical class 0.000 claims abstract description 12
- OOTFVKOQINZBBF-UHFFFAOYSA-N cystamine Chemical compound CCSSCCN OOTFVKOQINZBBF-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229940099500 cystamine Drugs 0.000 claims abstract description 12
- DHQUQYYPAWHGAR-UHFFFAOYSA-N dibenzyl 2-aminopentanedioate Chemical compound C=1C=CC=CC=1COC(=O)C(N)CCC(=O)OCC1=CC=CC=C1 DHQUQYYPAWHGAR-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000007151 ring opening polymerisation reaction Methods 0.000 claims abstract description 10
- 150000002500 ions Chemical class 0.000 claims description 36
- 239000003814 drug Substances 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 239000013067 intermediate product Substances 0.000 claims description 10
- NULDEVQACXJZLL-UHFFFAOYSA-N 2-(2-aminoethyldisulfanyl)ethylazanium;chloride Chemical compound Cl.NCCSSCCN NULDEVQACXJZLL-UHFFFAOYSA-N 0.000 claims description 9
- 229940079593 drug Drugs 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 239000003999 initiator Substances 0.000 claims description 6
- 239000011230 binding agent Substances 0.000 claims description 5
- 238000000502 dialysis Methods 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- -1 n- heptyl Chemical group 0.000 claims description 5
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 4
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical class CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 claims description 2
- 238000004132 cross linking Methods 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims 2
- 230000000996 additive effect Effects 0.000 claims 2
- 230000035484 reaction time Effects 0.000 claims 2
- 150000001413 amino acids Chemical class 0.000 claims 1
- HFXKQSZZZPGLKQ-UHFFFAOYSA-N cyclopentamine Chemical compound CNC(C)CC1CCCC1 HFXKQSZZZPGLKQ-UHFFFAOYSA-N 0.000 claims 1
- 229960003263 cyclopentamine Drugs 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 abstract description 8
- 201000011510 cancer Diseases 0.000 abstract description 6
- 239000002246 antineoplastic agent Substances 0.000 abstract description 4
- 229940041181 antineoplastic drug Drugs 0.000 abstract description 4
- 238000010521 absorption reaction Methods 0.000 abstract description 3
- 235000018102 proteins Nutrition 0.000 abstract description 3
- 102000004169 proteins and genes Human genes 0.000 abstract description 3
- 108090000623 proteins and genes Proteins 0.000 abstract description 3
- 239000003519 biomedical and dental material Substances 0.000 abstract description 2
- 238000000746 purification Methods 0.000 abstract description 2
- ATCFYQUZTYQTJN-AXDSSHIGSA-N (2s)-2-amino-4-benzylpentanedioic acid Chemical compound OC(=O)[C@@H](N)CC(C(O)=O)CC1=CC=CC=C1 ATCFYQUZTYQTJN-AXDSSHIGSA-N 0.000 abstract 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 235000018977 lysine Nutrition 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 108010020346 Polyglutamic Acid Proteins 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 229920002643 polyglutamic acid Polymers 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 6
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 235000019766 L-Lysine Nutrition 0.000 description 5
- 238000011068 loading method Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000005540 biological transmission Effects 0.000 description 4
- 238000004108 freeze drying Methods 0.000 description 4
- 230000002209 hydrophobic effect Effects 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 235000013339 cereals Nutrition 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
- 229960003180 glutathione Drugs 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 229910021642 ultra pure water Inorganic materials 0.000 description 3
- 239000012498 ultrapure water Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 108010024636 Glutathione Proteins 0.000 description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
- 150000008545 L-lysines Chemical class 0.000 description 2
- 229930012538 Paclitaxel Natural products 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 108010039918 Polylysine Proteins 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229940009456 adriamycin Drugs 0.000 description 2
- 238000011938 amidation process Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 230000004087 circulation Effects 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 230000036571 hydration Effects 0.000 description 2
- 238000006703 hydration reaction Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 238000003760 magnetic stirring Methods 0.000 description 2
- 229960001592 paclitaxel Drugs 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920000656 polylysine Polymers 0.000 description 2
- 239000002954 polymerization reaction product Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000012673 precipitation polymerization Methods 0.000 description 2
- 150000003220 pyrenes Chemical class 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 2
- 210000004881 tumor cell Anatomy 0.000 description 2
- DWNBOPVKNPVNQG-LURJTMIESA-N (2s)-4-hydroxy-2-(propylamino)butanoic acid Chemical compound CCCN[C@H](C(O)=O)CCO DWNBOPVKNPVNQG-LURJTMIESA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical class CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- LEVWYRKDKASIDU-QWWZWVQMSA-N D-cystine Chemical compound OC(=O)[C@H](N)CSSC[C@@H](N)C(O)=O LEVWYRKDKASIDU-QWWZWVQMSA-N 0.000 description 1
- 238000006957 Michael reaction Methods 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 150000003938 benzyl alcohols Chemical class 0.000 description 1
- 229920002988 biodegradable polymer Polymers 0.000 description 1
- 239000004621 biodegradable polymer Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 210000001124 body fluid Anatomy 0.000 description 1
- 239000010839 body fluid Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229960003067 cystine Drugs 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229960004679 doxorubicin Drugs 0.000 description 1
- 210000003038 endothelium Anatomy 0.000 description 1
- 235000020776 essential amino acid Nutrition 0.000 description 1
- 239000003797 essential amino acid Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229960002989 glutamic acid Drugs 0.000 description 1
- 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 description 1
- 239000012535 impurity Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000002540 macrophage Anatomy 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 210000000865 mononuclear phagocyte system Anatomy 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 231100001083 no cytotoxicity Toxicity 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000012667 polymer degradation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000001338 self-assembly Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/51—Nanocapsules; Nanoparticles
- A61K9/5107—Excipients; Inactive ingredients
- A61K9/513—Organic macromolecular compounds; Dendrimers
- A61K9/5146—Organic macromolecular compounds; Dendrimers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyamines, polyanhydrides
-
- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/337—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having four-membered rings, e.g. taxol
-
- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/351—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom not condensed with another ring
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
- A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
- A61K31/704—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/51—Nanocapsules; Nanoparticles
- A61K9/5192—Processes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- Biomedical Technology (AREA)
- Nanotechnology (AREA)
- Optics & Photonics (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Polyamides (AREA)
- Medicinal Preparation (AREA)
Abstract
Description
Claims (10)
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201810432125.XA CN108498483B (zh) | 2018-05-08 | 2018-05-08 | 一种pH/还原响应性聚氨基酸两性离子纳米颗粒的制备方法 |
US16/494,993 US10933028B2 (en) | 2018-05-08 | 2018-12-03 | Method of preparing pH/reduction responsive polyamino acid zwitterionic nanoparticles |
PCT/CN2018/118862 WO2019214219A1 (zh) | 2018-05-08 | 2018-12-03 | 一种pH/还原响应性聚氨基酸两性离子纳米颗粒的制备方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201810432125.XA CN108498483B (zh) | 2018-05-08 | 2018-05-08 | 一种pH/还原响应性聚氨基酸两性离子纳米颗粒的制备方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN108498483A true CN108498483A (zh) | 2018-09-07 |
CN108498483B CN108498483B (zh) | 2020-10-09 |
Family
ID=63399881
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201810432125.XA Active CN108498483B (zh) | 2018-05-08 | 2018-05-08 | 一种pH/还原响应性聚氨基酸两性离子纳米颗粒的制备方法 |
Country Status (3)
Country | Link |
---|---|
US (1) | US10933028B2 (zh) |
CN (1) | CN108498483B (zh) |
WO (1) | WO2019214219A1 (zh) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2019214219A1 (zh) * | 2018-05-08 | 2019-11-14 | 江南大学 | 一种pH/还原响应性聚氨基酸两性离子纳米颗粒的制备方法 |
CN110713596A (zh) * | 2019-11-08 | 2020-01-21 | 西北师范大学 | 肿瘤无导管栓塞用pH-还原双响应高分子栓塞剂及其合成 |
CN114181269A (zh) * | 2021-12-10 | 2022-03-15 | 安徽工业大学 | 一种含有硫醚键的半乳糖基化脂化物及其合成方法 |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113045746B (zh) * | 2021-04-30 | 2022-05-27 | 北京化工大学 | 一种水杨酸o-羧酸酐开环聚合诱导合成自组装纳米体的方法 |
CN113456611A (zh) * | 2021-06-11 | 2021-10-01 | 淮阴工学院 | 一种双响应快速控释的纳米载体及所构成的纳米药物制备方法 |
CN114524932A (zh) * | 2022-02-16 | 2022-05-24 | 宁德师范学院 | 双亲性三嵌段聚氨基酸共聚物、中间体、制备及应用 |
CN114957647B (zh) * | 2022-04-07 | 2024-03-19 | 合肥工业大学 | 一种可变形双重响应性高载药量聚前药纳米载体的制备方法 |
CN115518197B (zh) * | 2022-07-25 | 2024-03-19 | 上海大学 | 用于骨缺损修复的聚氨基酸纳米纤维开口中空微载体、其制备方法及其应用 |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008109483A1 (en) * | 2007-03-02 | 2008-09-12 | The Board Of Trustees Of The University Of Illinois | Particulate drug delivery |
CN102875733A (zh) * | 2012-10-25 | 2013-01-16 | 西安科技大学 | 具有仿细胞外层膜结构的纳米颗粒及其制备方法 |
CN103976949A (zh) * | 2014-04-30 | 2014-08-13 | 成都市绿科华通科技有限公司 | 一种智能抗癌症高分子药物体系构建 |
CN105820334A (zh) * | 2016-05-19 | 2016-08-03 | 江南大学 | 一种基于氨基酸的聚两性离子纳米颗粒的制备方法 |
CN106727307A (zh) * | 2016-12-12 | 2017-05-31 | 江苏师范大学 | 一种还原敏感纳米胶束的制备及应用 |
CN107556438A (zh) * | 2017-10-18 | 2018-01-09 | 西南民族大学 | 多重响应性交联聚合物及载药纳米胶束和它们的制备方法 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BR0315194A (pt) * | 2002-10-31 | 2005-08-23 | Umd Inc | Composições terapêuticas para liberação de droga para a, e através da, cobertura epitelial |
CN104491871B (zh) | 2014-12-02 | 2017-03-29 | 江南大学 | 一种基于聚谷氨酸和胱胺的pH与还原敏感性的纳米微凝胶 |
CN105001442B (zh) | 2015-08-20 | 2017-10-13 | 西南交通大学 | 一种微孔自发泡制备多孔水凝胶的方法 |
CN108498483B (zh) * | 2018-05-08 | 2020-10-09 | 江南大学 | 一种pH/还原响应性聚氨基酸两性离子纳米颗粒的制备方法 |
-
2018
- 2018-05-08 CN CN201810432125.XA patent/CN108498483B/zh active Active
- 2018-12-03 US US16/494,993 patent/US10933028B2/en active Active
- 2018-12-03 WO PCT/CN2018/118862 patent/WO2019214219A1/zh active Application Filing
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008109483A1 (en) * | 2007-03-02 | 2008-09-12 | The Board Of Trustees Of The University Of Illinois | Particulate drug delivery |
CN102875733A (zh) * | 2012-10-25 | 2013-01-16 | 西安科技大学 | 具有仿细胞外层膜结构的纳米颗粒及其制备方法 |
CN103976949A (zh) * | 2014-04-30 | 2014-08-13 | 成都市绿科华通科技有限公司 | 一种智能抗癌症高分子药物体系构建 |
CN105820334A (zh) * | 2016-05-19 | 2016-08-03 | 江南大学 | 一种基于氨基酸的聚两性离子纳米颗粒的制备方法 |
CN106727307A (zh) * | 2016-12-12 | 2017-05-31 | 江苏师范大学 | 一种还原敏感纳米胶束的制备及应用 |
CN107556438A (zh) * | 2017-10-18 | 2018-01-09 | 西南民族大学 | 多重响应性交联聚合物及载药纳米胶束和它们的制备方法 |
Non-Patent Citations (5)
Title |
---|
BING DENG ET AL.: ""Reduction-sensitive polymeric nanocarriers in cancer therapy: a comprehensive review"", 《NANOSCALE》 * |
LEI LIU ET AL.: ""Synthesis strategies for disulfide bond-containing polymerbased drug delivery system for reduction-responsive controlled release"", 《FRONT. MATER. SCI.》 * |
LIPING ZHANG ET AL.: ""Studies on the preparation and controlled release of redox/pH-responsive zwitterionic nanoparticles based on poly-L-glutamic acid and cystamine"", 《JOURNAL OF BIOMATERIALS SCIENCE, POLYMER EDITION》 * |
吴鲁艳: ""pH/还原响应性两性离子纳米颗粒的制备及药物控释研究"", 《中国优秀硕士学位论文全文数据库(电子期刊)》 * |
段鹏雪: ""生物可降解环境响应聚合物的制备及性能研究"", 《中国优秀硕士学位论文全文数据库(电子期刊)》 * |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2019214219A1 (zh) * | 2018-05-08 | 2019-11-14 | 江南大学 | 一种pH/还原响应性聚氨基酸两性离子纳米颗粒的制备方法 |
US10933028B2 (en) | 2018-05-08 | 2021-03-02 | Jiangnan University | Method of preparing pH/reduction responsive polyamino acid zwitterionic nanoparticles |
CN110713596A (zh) * | 2019-11-08 | 2020-01-21 | 西北师范大学 | 肿瘤无导管栓塞用pH-还原双响应高分子栓塞剂及其合成 |
CN110713596B (zh) * | 2019-11-08 | 2022-04-29 | 西北师范大学 | 肿瘤无导管栓塞用pH-还原双响应高分子栓塞剂及其合成 |
CN114181269A (zh) * | 2021-12-10 | 2022-03-15 | 安徽工业大学 | 一种含有硫醚键的半乳糖基化脂化物及其合成方法 |
CN114181269B (zh) * | 2021-12-10 | 2023-09-29 | 安徽工业大学 | 一种含有硫醚键的半乳糖基化脂化物及其合成方法 |
Also Published As
Publication number | Publication date |
---|---|
CN108498483B (zh) | 2020-10-09 |
US10933028B2 (en) | 2021-03-02 |
WO2019214219A1 (zh) | 2019-11-14 |
US20200281865A1 (en) | 2020-09-10 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN108498483A (zh) | 一种pH/还原响应性聚氨基酸两性离子纳米颗粒的制备方法 | |
Aiping et al. | Synthesis and characterization of N-succinyl-chitosan and its self-assembly of nanospheres | |
CN107550921B (zh) | 一种纳米颗粒-高分子可注射复合水凝胶双载药体系及其制备方法 | |
Kim et al. | Poly (ethylene glycol)-containing hydrogels for oral protein delivery applications | |
Sang et al. | Preparation of pH/redox dual responsive polymeric micelles with enhanced stability and drug controlled release | |
US10632071B2 (en) | Preparation method for charge reversal and reversibly crosslinked redox-sensitive nanomicelles | |
Fan et al. | Multi-responsive polypeptide hydrogels derived from N-carboxyanhydride terpolymerizations for delivery of nonsteroidal anti-inflammatory drugs | |
CN105251013B (zh) | 一种具有氧化还原响应性可降解水溶性抗肿瘤聚合物前药及其制备方法 | |
CN104311821B (zh) | 一种具有双重响应性聚合物载药纳米胶束的制备 | |
Yin et al. | Itaconic acid grafted carboxymethyl chitosan and its nanoparticles: Preparation, characterization and evaluation | |
CN109438707B (zh) | 一种用于抗肿瘤药物递送的聚二硫苏糖醇纳米体系及其制备方法和应用 | |
Liu et al. | Preparation and characterization of glutaraldehyde cross-linked O-carboxymethylchitosan microspheres for controlled delivery of pazufloxacin mesilate | |
WO2008007092A1 (en) | Composition | |
CN111621024B (zh) | 快速氧化/还原双重响应性含双硒键的嵌段共聚物的制备方法 | |
Soleimani et al. | Photodegradable poly (ester amide) s for indirect light-triggered release of paclitaxel | |
Michailova et al. | Nanoparticles formed from PNIPAM-g-PEO copolymers in the presence of indomethacin | |
Baruah et al. | Novel non-mulberry silk fibroin nanoparticles with enhanced activity as potential candidate in nanocarrier mediated delivery system | |
Singhal et al. | Stimulus responsive soy-protein based hydrogels through grafting HEMA for biomedical applications | |
CN111407740A (zh) | 一种超声可激活释放药物的白蛋白纳米粒子、其制备方法及应用 | |
CN111592634B (zh) | 一种光还原自降解高分子及其制备方法和应用 | |
Alam et al. | Synthesis, characterization, drug solubility enhancement, and drug release study of poly (methacrylic acid-graft-simvastatin) | |
CN110386890B (zh) | 一种基于胱氨酰胺衍生物的载药纳米水凝胶及其制备方法 | |
CN114409607B (zh) | 一种含有硫醚基团的n-羧基环内酸酐及其制备方法和应用 | |
US8796234B2 (en) | Crosslinking branched molecule through thiol-disulfide exchange to form hydrogel | |
Pourjavadi et al. | Synthesis and characterization of stimuli responsive micelles from chitosan, starch, and alginate based on graft copolymers with polylactide-poly (methacrylic acid) and polylactide-poly [2 (dimethyl amino) ethyl methacrylate] side chains |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant | ||
TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20231109 Address after: Floor 2, Building 22, Yard 1, Jinghai Fifth Road, Tongzhou District, Beijing, 101100 Patentee after: BEIJING ABACE BIOTECHNOLOGY Co.,Ltd. Address before: 1800 No. 214122 Jiangsu city of Wuxi Province Li Lake Avenue Patentee before: Jiangnan University |
|
TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20231122 Address after: Floor 2, Building 22, Yard 1, Jinghai Fifth Road, Tongzhou District, Beijing, 101100 Patentee after: BEIJING ABACE BIOTECHNOLOGY Co.,Ltd. Patentee after: Anhui Zhangwen Pharmaceutical Co.,Ltd. Address before: Floor 2, Building 22, Yard 1, Jinghai Fifth Road, Tongzhou District, Beijing, 101100 Patentee before: BEIJING ABACE BIOTECHNOLOGY Co.,Ltd. |