CN101838289A - 使用放射性同位素标示亲油性盐的用于线粒体机能障碍的非侵入性诊断显像技术 - Google Patents
使用放射性同位素标示亲油性盐的用于线粒体机能障碍的非侵入性诊断显像技术 Download PDFInfo
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| US20100111867A1 (en) * | 2007-02-16 | 2010-05-06 | The University Of Sydney | Carborane-phosphonium compounds and their use in boron neutron capture therapy and imaging |
| EP1990310A1 (en) * | 2007-04-23 | 2008-11-12 | Trasis S.A. | Method for the preparation of reactive 18F fluoride, and for the labeling of radiotracers, using a modified non-ionic solid support and without any evaporation step |
| WO2008151003A2 (en) * | 2007-05-30 | 2008-12-11 | Children's Medical Center Corporation | Novel fluorine-18 labeled rhodamine derivatives for myocardial perfusion imaging with positron emission tomography |
| US9717896B2 (en) | 2007-12-18 | 2017-08-01 | Gearbox, Llc | Treatment indications informed by a priori implant information |
| US8636670B2 (en) | 2008-05-13 | 2014-01-28 | The Invention Science Fund I, Llc | Circulatory monitoring systems and methods |
| US20090287120A1 (en) | 2007-12-18 | 2009-11-19 | Searete Llc, A Limited Liability Corporation Of The State Of Delaware | Circulatory monitoring systems and methods |
| US8388936B2 (en) * | 2008-02-22 | 2013-03-05 | Mcw Research Foundation, Inc. | In vivo mitochondrial labeling using positively-charged nitroxide enhanced and gadolinium chelate enhanced magnetic resonance imaging |
| US8388931B2 (en) * | 2008-02-29 | 2013-03-05 | Marcos Lopez | 99m Tc-labeled triphenylphosphonium derivative contrasting agents and molecular probes for early detection and imaging of breast tumors |
| KR101616139B1 (ko) | 2008-02-29 | 2016-04-27 | 랜티우스 메디컬 이메징, 인크. | 관류 영상화를 포함하는 용도를 위한 조영제 |
| EP3231804B1 (en) | 2008-03-21 | 2021-03-03 | The General Hospital Corporation | Compounds and compositions for the detection and treatment of alzheimer's disease and related disorders |
| JP5539962B2 (ja) | 2008-04-25 | 2014-07-02 | ノースウェスタン、ユニバーシティ | コレステロールを隔離するのに適したナノ構造体 |
| JP5322527B2 (ja) * | 2008-07-17 | 2013-10-23 | 浜松ホトニクス株式会社 | アポトーシスの検出に適した化合物 |
| DK2419096T3 (da) | 2009-04-15 | 2020-02-03 | Lantheus Medical Imaging Inc | Stabilisering af radiofarmaceutiske sammensætninger under anvendelse af ascorbinsyre |
| WO2011003591A1 (en) | 2009-07-10 | 2011-01-13 | Bayer Schering Pharma Aktiengesellschaft | Usage of low to medium-pressure liquid chromatography for the purification of radiotracers |
| MX348958B (es) | 2010-02-08 | 2017-07-04 | Lantheus Medical Imaging Inc | Métodos y aparatos para sintetizar agentes formadores de imagen e intermedios de estos. |
| GB201005624D0 (en) * | 2010-04-01 | 2010-05-19 | Medical Res Council | Probe |
| KR101172157B1 (ko) | 2010-05-27 | 2012-08-07 | 전남대학교산학협력단 | 미토콘드리아 영상을 위한 방사성 약물의 제조 방법 |
| US9205156B2 (en) | 2010-05-27 | 2015-12-08 | Hadasit Medical Research Services & Development Limited | Molecular imaging agents |
| AU2013203000B9 (en) | 2012-08-10 | 2017-02-02 | Lantheus Medical Imaging, Inc. | Compositions, methods, and systems for the synthesis and use of imaging agents |
| CN102898470B (zh) * | 2012-11-02 | 2014-12-10 | 北京师范大学 | 一类新型有机膦化合物及其制备方法和应用 |
| EP3076918A4 (en) | 2013-12-03 | 2017-06-07 | Northwestern University | Liposomal particles, methods of making same and uses thereof |
| CN107002081A (zh) | 2014-10-06 | 2017-08-01 | 埃克西奎雷股份有限公司 | 抗tnf化合物 |
| US20180030074A1 (en) * | 2014-11-05 | 2018-02-01 | Shozo Furumoto | Phosphonium compound and production method therefor |
| CN107233585B (zh) * | 2017-06-09 | 2021-01-22 | 四川大学华西医院 | 黄连素或其衍生物在制备心肌灌注显像剂中的用途 |
| KR20200028997A (ko) | 2017-07-13 | 2020-03-17 | 노오쓰웨스턴 유니버시티 | 올리고뉴클레오타이드-작용화된 금속-유기 프레임워크 나노입자를 제조하는 일반적이고 직접적인 방법 |
| PL239871B1 (pl) * | 2018-09-05 | 2022-01-24 | Synektik Spolka Akcyjna | Znakowany radioizotopem związek czwartorzędowej soli amoniowej wielopierścieniowej aminy aromatycznej, zastosowanie znakowanego radioizotopem związku w metodzie diagnostycznej pozytonowej tomografii emisyjnej, a także kompozycja farmaceutyczna zawierająca znakowany radioizotopem związek czwartorzędowej soli amoniowej wielopierścieniowej aminy aromatycznej |
| CN110577478A (zh) * | 2018-10-25 | 2019-12-17 | 南方医科大学南方医院 | 一种正电子探针及其制备方法与应用 |
| WO2021055814A1 (en) * | 2019-09-18 | 2021-03-25 | The Regents Of The University Of California | Positron emission tomography guided delivery of mitochondral complex i inhibitors |
| US12319711B2 (en) | 2019-09-20 | 2025-06-03 | Northwestern University | Spherical nucleic acids with tailored and active protein coronae |
| US12378560B2 (en) | 2019-10-29 | 2025-08-05 | Northwestern University | Sequence multiplicity within spherical nucleic acids |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4446123A (en) * | 1982-10-13 | 1984-05-01 | Hahnemann University | Process of radioimaging the myocardium of mammals utilizing radiolabeled lipophilic cations |
| JP3992923B2 (ja) | 1997-09-03 | 2007-10-17 | イムノメディクス， インコーポレイテッド | Ｆ−１８陽電子放出トモグラフィー用のタン白及びペプチドのフッ素化方法 |
| JPH11295494A (ja) | 1998-04-08 | 1999-10-29 | Nippon Meji Physics Kk | ［ｆ−１８］−フッ化物イオンの製造方法 |
| WO2001082864A2 (en) * | 2000-04-28 | 2001-11-08 | Duke University | 18f-labeled choline analogs |
| EP1174771B1 (en) * | 2000-06-21 | 2008-06-11 | Canon Kabushiki Kaisha | Electrophotographic photosensitive member, process cartridge and electrophotographic apparatus |
| TWI266634B (en) * | 2002-02-06 | 2006-11-21 | Univ Johns Hopkins | Non-invasive diagnostic imaging technology for mitochondria dysfunction using radiolabeled lipophilic salts |
| US7515953B2 (en) | 2002-08-01 | 2009-04-07 | The Johns Hopkins University | Techniques for identifying molecular structures and treating cell types lining a body lumen using fluorescence |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| TWI611795B (zh) * | 2016-07-18 | 2018-01-21 | 許百靈 | 多針孔單光子ｓｐｅｃｔ心肌血流絕對定量方法與用途 |
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| CA2474142A1 (en) | 2003-08-14 |
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| US20040033197A1 (en) | 2004-02-19 |
| CA2474142C (en) | 2013-02-05 |
| TW200307524A (en) | 2003-12-16 |
| JP4530665B2 (ja) | 2010-08-25 |
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