ES2979129T3 - Composiciones y métodos para la fluorescencia mejorada - Google Patents
Composiciones y métodos para la fluorescencia mejorada Download PDFInfo
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- ES2979129T3 ES2979129T3 ES17765041T ES17765041T ES2979129T3 ES 2979129 T3 ES2979129 T3 ES 2979129T3 ES 17765041 T ES17765041 T ES 17765041T ES 17765041 T ES17765041 T ES 17765041T ES 2979129 T3 ES2979129 T3 ES 2979129T3
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- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
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| WO2018045278A1 (en) * | 2016-09-01 | 2018-03-08 | Life Technologies Corporation | Compositions and methods for enhanced fluorescence |
| US11674901B2 (en) | 2017-06-16 | 2023-06-13 | Duke University | Resonator networks for improved label detection, computation, analyte sensing, and tunable random number generation |
| JP7403744B2 (ja) | 2017-10-05 | 2023-12-25 | ソニーグループ株式会社 | プログラマブルな樹枝状薬物 |
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| CN111836645A (zh) | 2017-11-16 | 2020-10-27 | 索尼公司 | 可编程的聚合药物 |
| US20190154669A1 (en) * | 2017-11-20 | 2019-05-23 | Vector Laboratories, Inc. | Methods and systems for species-on-species immunoassay detection |
| JP2021510698A (ja) | 2018-01-12 | 2021-04-30 | ソニー株式会社 | 生物学的に活性な化合物を含むホスホアルキルリボースポリマー |
| EP3737418B1 (en) | 2018-01-12 | 2024-02-28 | Sony Group Corporation | Polymers with rigid spacing groups comprising biologically active compounds |
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| WO2019182766A1 (en) | 2018-03-21 | 2019-09-26 | Sony Corporation | Polymeric tandem dyes with linker groups |
| WO2019191482A1 (en) | 2018-03-30 | 2019-10-03 | Becton, Dickinson And Company | Water-soluble polymeric dyes having pendant chromophores |
| WO2020006285A1 (en) | 2018-06-27 | 2020-01-02 | Sony Corporation | Polymeric dyes with linker groups comprising deoxyribose |
| CN109086566B (zh) * | 2018-07-12 | 2021-06-18 | 浙江工业大学 | 一种基于片段重采样的群体蛋白质结构预测方法 |
| JP2022533145A (ja) * | 2019-05-13 | 2022-07-21 | シャンハイ ポラリス バイオロジー カンパニー， リミテッド | 生体分子を標識するためのタグ |
| US20220229047A1 (en) * | 2019-06-20 | 2022-07-21 | Konica Minolta, Inc. | Linked body for fluorescent labeling agents |
| KR102718543B1 (ko) | 2019-09-26 | 2024-10-18 | 소니그룹주식회사 | 링커 그룹을 갖는 중합체성 탠덤 염료 |
| WO2021193682A1 (ja) * | 2020-03-25 | 2021-09-30 | 積水メディカル株式会社 | 免疫学的分析方法及び免疫学的分析試薬キット |
| CN113913404B (zh) * | 2020-07-10 | 2025-08-12 | 上海米然生物科技有限公司 | 一种荧光交联RNase H突变体缀合物及其应用 |
| US11408825B2 (en) | 2020-08-28 | 2022-08-09 | Hong Kong Applied Science and Technology Research Institute Company Limited | Forensic detector and the system thereof |
| US12203914B2 (en) | 2020-11-12 | 2025-01-21 | Sartorius Bioanalytical Instruments, Inc. | Viral clearance evaluation for biological medical product preparation processes |
| EP4256078A1 (en) | 2020-12-07 | 2023-10-11 | Sony Group Corporation | Spacing linker group design for brightness enhancement in dimeric or polymeric dyes |
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| US6972326B2 (en) | 2001-12-03 | 2005-12-06 | Molecular Probes, Inc. | Labeling of immobilized proteins using dipyrrometheneboron difluoride dyes |
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| US9127130B2 (en) | 2006-08-11 | 2015-09-08 | Starpharma Pty Ltd. | Polylysine dendrimer contrast agent |
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| WO2009078970A1 (en) * | 2007-12-14 | 2009-06-25 | Biotium, Inc. | Fluorescent compounds |
| EP3981819B1 (en) * | 2010-01-19 | 2024-02-28 | Sirigen II Limited | Novel reagents for directed biomarker signal amplification |
| JP5540964B2 (ja) | 2010-07-23 | 2014-07-02 | コニカミノルタ株式会社 | 蛍光標識剤、並びにこれを用いた結合体及びバイオアッセイ法 |
| US9448173B2 (en) | 2011-03-08 | 2016-09-20 | The Board Of Trustees Of The University Of Illinois | Dye-conjugated dendrimers |
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| US9670318B2 (en) | 2015-05-28 | 2017-06-06 | Miltenyi Biotec Gmbh | Bright fluorochromes based on multimerization of fluorescent dyes |
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| EP3507603C0 (en) | 2024-03-06 |
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