RU2016144055A - Конъюгаты лекарственного средства с наночастицами - Google Patents
Конъюгаты лекарственного средства с наночастицами Download PDFInfo
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- RU2016144055A RU2016144055A RU2016144055A RU2016144055A RU2016144055A RU 2016144055 A RU2016144055 A RU 2016144055A RU 2016144055 A RU2016144055 A RU 2016144055A RU 2016144055 A RU2016144055 A RU 2016144055A RU 2016144055 A RU2016144055 A RU 2016144055A
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/001—Preparation for luminescence or biological staining
- A61K49/0063—Preparation for luminescence or biological staining characterised by a special physical or galenical form, e.g. emulsions, microspheres
- A61K49/0069—Preparation for luminescence or biological staining characterised by a special physical or galenical form, e.g. emulsions, microspheres the agent being in a particular physical galenical form
- A61K49/0089—Particulate, powder, adsorbate, bead, sphere
- A61K49/0091—Microparticle, microcapsule, microbubble, microsphere, microbead, i.e. having a size or diameter higher or equal to 1 micrometer
- A61K49/0093—Nanoparticle, nanocapsule, nanobubble, nanosphere, nanobead, i.e. having a size or diameter smaller than 1 micrometer, e.g. polymeric nanoparticle
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/69—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6921—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit the form being a particulate, a powder, an adsorbate, a bead or a sphere
- A61K47/6923—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit the form being a particulate, a powder, an adsorbate, a bead or a sphere the form being an inorganic particle, e.g. ceramic particles, silica particles, ferrite or synsorb
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- 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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
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- 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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
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- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/56—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
- A61K47/59—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyureas or polyurethanes
- A61K47/60—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyureas or polyurethanes the organic macromolecular compound being a polyoxyalkylene oligomer, polymer or dendrimer, e.g. PEG, PPG, PEO or polyglycerol
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- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/62—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being a protein, peptide or polyamino acid
- A61K47/64—Drug-peptide, drug-protein or drug-polyamino acid conjugates, i.e. the modifying agent being a peptide, protein or polyamino acid which is covalently bonded or complexed to a therapeutically active agent
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- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/62—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being a protein, peptide or polyamino acid
- A61K47/65—Peptidic linkers, binders or spacers, e.g. peptidic enzyme-labile linkers
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/69—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6921—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit the form being a particulate, a powder, an adsorbate, a bead or a sphere
- A61K47/6927—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit the form being a particulate, a powder, an adsorbate, a bead or a sphere the form being a solid microparticle having no hollow or gas-filled cores
- A61K47/6929—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit the form being a particulate, a powder, an adsorbate, a bead or a sphere the form being a solid microparticle having no hollow or gas-filled cores the form being a nanoparticle, e.g. an immuno-nanoparticle
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/69—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6921—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit the form being a particulate, a powder, an adsorbate, a bead or a sphere
- A61K47/6927—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit the form being a particulate, a powder, an adsorbate, a bead or a sphere the form being a solid microparticle having no hollow or gas-filled cores
- A61K47/6929—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit the form being a particulate, a powder, an adsorbate, a bead or a sphere the form being a solid microparticle having no hollow or gas-filled cores the form being a nanoparticle, e.g. an immuno-nanoparticle
- A61K47/6931—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit the form being a particulate, a powder, an adsorbate, a bead or a sphere the form being a solid microparticle having no hollow or gas-filled cores the form being a nanoparticle, e.g. an immuno-nanoparticle the material constituting the nanoparticle being a polymer
- A61K47/6935—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit the form being a particulate, a powder, an adsorbate, a bead or a sphere the form being a solid microparticle having no hollow or gas-filled cores the form being a nanoparticle, e.g. an immuno-nanoparticle the material constituting the nanoparticle being a polymer the polymer being obtained otherwise than by reactions involving carbon to carbon unsaturated bonds, e.g. polyesters, polyamides or polyglycerol
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- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/12—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by a special physical form, e.g. emulsion, microcapsules, liposomes, characterized by a special physical form, e.g. emulsions, dispersions, microcapsules
- A61K51/1241—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by a special physical form, e.g. emulsion, microcapsules, liposomes, characterized by a special physical form, e.g. emulsions, dispersions, microcapsules particles, powders, lyophilizates, adsorbates, e.g. polymers or resins for adsorption or ion-exchange resins
- A61K51/1244—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by a special physical form, e.g. emulsion, microcapsules, liposomes, characterized by a special physical form, e.g. emulsions, dispersions, microcapsules particles, powders, lyophilizates, adsorbates, e.g. polymers or resins for adsorption or ion-exchange resins microparticles or nanoparticles, e.g. polymeric nanoparticles
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- A61P35/00—Antineoplastic agents
Claims (29)
1. Конъюгат лекарственного средства с наночастицами (NDC), включающий
наночастицу;
линкерный фрагмент; и
фрагмент лекарственного средства,
в котором наночастица покрыта органическим полимером, и
в котором фрагмент лекарственного средства и линкерный фрагмент образуют расщепляемую конструкцию линкер-лекарственное средство, которая ковалентно связана с наночастицей.
2. Конъюгат по п. 1, отличающийся тем, что указанная наночастица имеет диаметр в диапазоне от 1 нм до 25 нм.
3. Конъюгат по п. 1 или 2, отличающийся тем, что указанный фрагмент лекарственного средства содержит дазатиниб или гефитиниб, включая любые их аналоги.
4. Конъюгат по п. 1 или 2, отличающийся тем, что указанное среднее соотношение фрагмента лекарственного средства и наночастиц находится в диапазоне от 1 до 20.
5. Конъюгат по п. 1, отличающийся тем, что линкерный фрагмент содержит одну или более аминокислот.
6. Конъюгат по п. 2, отличающийся тем, что линкерный фрагмент содержит (амино-(спейсер)x)y-пептид или (спейсер)z-пептид,
где спейсер содержит от 2 до 50 атомов,
где x представляет собой целое число от 1 до 5,
где y представляет собой целое число от 1 до 5,
где z представляет собой целое число от 5 до 15, и
где линкерный фрагмент содержит разлагаемый фрагмент между линкерным фрагментом и фрагментом лекарственного средства.
7. Конъюгат по любому из пп. 1-6, отличающийся тем, что указанный линкерный фрагмент позволяет отщепление фрагмента лекарственного средства в присутствии протеазы.
8. Конъюгат по любому из пп. 1-7, отличающийся тем, что линкерный фрагмент содержит спейсер между пептидом и фрагментом лекарственного средства.
9. Конъюгат по п. 8, отличающийся тем, что указанный спейсер содержит полиэтиленгликоль (ПЭГ), ПЭГ2, пара-аминобензилоксикарбамат (РАВС).
10. Конъюгат по любому из пп. 1-9, дополнительно содержащий флуоресцентное соединение.
11. Конъюгат по любому из пп. 1-10, дополнительно содержащий радиоактивную метку.
12. Конъюгат по любому из пп. 1-11, отличающийся тем, что линкерный фрагмент способен подвергаться гидролизу на С-конце при связывании с протеазой, таким образом высвобождая фрагмент лекарственного средства из наночастицы.
13. Конъюгат по любому из пп. 1-12, отличающийся тем, что фрагмент лекарственного средства содержит ингибитор рецепторной тирозинкиназы (RTK).
14. Конъюгат по любому из пп. 1-13, дополнительно содержащий от 1 до 20 нацеливаемых фрагментов, при этом нацеливаемые фрагменты связываются с рецепторами на опухолевых клетках.
15. Конъюгат по п. 14, отличающийся тем, что указанные нацеливаемые фрагменты содержат циклическую аргинилглициласпарагиновую кислоту (cRGD).
16. Конъюгат по п. 13, отличающийся тем, что указанный конъюгат лекарственного средства с наночастицами (NDC) является лечебно-диагностическим средством.
17. Конъюгат по любому из пп. 11-16, отличающийся тем, что флуоресцентное соединение представляет собой Cy5.5.
18. Конъюгат по любому из пп. 11-17, отличающийся тем, что фрагмент лекарственного средства присоединен к радиоактивной метке.
19. Конъюгат по любому из пп. 1-18, отличающийся тем, что наночастица дополнительно содержит ядро на основе диоксида кремния и оболочку из диоксида кремния вокруг по меньшей мере части ядра.
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
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US201462004738P | 2014-05-29 | 2014-05-29 | |
US62/004,738 | 2014-05-29 | ||
US201462094923P | 2014-12-19 | 2014-12-19 | |
US62/094,923 | 2014-12-19 | ||
PCT/US2015/032565 WO2015183882A1 (en) | 2014-05-29 | 2015-05-27 | Nanoparticle drug conjugates |
Publications (1)
Publication Number | Publication Date |
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RU2016144055A true RU2016144055A (ru) | 2018-07-02 |
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RU2016144055A RU2016144055A (ru) | 2014-05-29 | 2015-05-27 | Конъюгаты лекарственного средства с наночастицами |
Country Status (13)
Country | Link |
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US (3) | US10111963B2 (ru) |
EP (2) | EP3148591B1 (ru) |
JP (1) | JP6573633B2 (ru) |
KR (2) | KR102051038B1 (ru) |
CN (2) | CN113082225A (ru) |
AU (1) | AU2015267200B2 (ru) |
BR (1) | BR112016027624A8 (ru) |
CA (2) | CA2947895C (ru) |
DK (1) | DK3148591T3 (ru) |
ES (1) | ES2788865T3 (ru) |
PL (1) | PL3148591T3 (ru) |
RU (1) | RU2016144055A (ru) |
WO (1) | WO2015183882A1 (ru) |
Families Citing this family (16)
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ES2639310T3 (es) | 2009-07-02 | 2017-10-26 | Sloan-Kettering Institute For Cancer Research | Nanopartículas fluorescentes basadas en sílice |
AU2014232907B2 (en) | 2013-03-15 | 2017-12-21 | Cornell University | Multimodal silica-based nanoparticles |
CN106455979A (zh) | 2013-12-31 | 2017-02-22 | 纪念斯隆-凯特琳癌症中心 | 用于荧光源实时多通道成像的系统、方法和设备 |
US10111963B2 (en) | 2014-05-29 | 2018-10-30 | Memorial Sloan Kettering Cancer Center | Nanoparticle drug conjugates |
AU2015362663B2 (en) | 2014-12-15 | 2020-07-09 | Cornell University | Cyclic peptides with enhanced nerve-binding selectivity, nanoparticles bound with said cyclic peptides, and use of same for real-time in vivo nerve tissue imaging |
EP3302568B1 (en) | 2015-05-29 | 2023-12-06 | Memorial Sloan Kettering Cancer Center | Methods of treatment using ultrasmall nanoparticles to induce cell death of nutrient-deprived cancer cells via ferroptosis |
US20210220494A1 (en) | 2016-04-29 | 2021-07-22 | Memorial Sloan Kettering Cancer Center | Compositions and methods for targeted particle penetration, distribution, and response in malignant brain tumors |
JP2019530485A (ja) | 2016-07-07 | 2019-10-24 | メモリアル スローン ケタリング キャンサー センター | 粒子駆動型、知識ベースかつ予測的がんラジオゲノミクスのためのイメージングシステムおよび方法 |
AU2018271781A1 (en) * | 2017-05-25 | 2019-12-12 | Cornell University | Ultrasmall nanoparticles labeled with Zirconium-89 and methods thereof |
US20210145985A1 (en) | 2017-06-23 | 2021-05-20 | Memorial Sloan Kettering Cancer Center | Method of imaging in vivo tissues using nanoparticles comprising a reference dye and a sensor dye |
RU2679075C1 (ru) * | 2017-11-09 | 2019-02-05 | Федеральное бюджетное учреждение науки "Государственный научный центр вирусологии и биотехнологии "Вектор" Федеральной службы по надзору в сфере защиты прав потребителей и благополучия человека (ФБУН ГНЦ ВБ "Вектор" Роспотребнадзора) | Конъюгат люминесцентных наночастиц диоксида кремния с рекомбинантными однодоменными нано - моноантителами C7b ламы, способными специфически взаимодействовать с рекомбинантным белком HER2/neu - аналогом природного рецептора эпидермального фактора роста EGFR/ERBB клеток человека |
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US10485881B2 (en) | 2019-11-26 |
CN106659797B (zh) | 2021-04-27 |
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BR112016027624A8 (pt) | 2021-07-20 |
JP6573633B2 (ja) | 2019-09-11 |
CA2947895A1 (en) | 2015-12-03 |
CN113082225A (zh) | 2021-07-09 |
CA2947895C (en) | 2023-08-08 |
EP3148591A1 (en) | 2017-04-05 |
US20200289668A1 (en) | 2020-09-17 |
KR102231672B1 (ko) | 2021-03-24 |
US20190070310A1 (en) | 2019-03-07 |
EP3693026A1 (en) | 2020-08-12 |
US10111963B2 (en) | 2018-10-30 |
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