JP2013544242A5 - - Google Patents
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- JP2013544242A5 JP2013544242A5 JP2013537779A JP2013537779A JP2013544242A5 JP 2013544242 A5 JP2013544242 A5 JP 2013544242A5 JP 2013537779 A JP2013537779 A JP 2013537779A JP 2013537779 A JP2013537779 A JP 2013537779A JP 2013544242 A5 JP2013544242 A5 JP 2013544242A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- compound according
- sample
- detecting
- independently
- 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.)
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- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 27
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 102000004190 Enzymes Human genes 0.000 claims description 12
- 108090000790 Enzymes Proteins 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 238000004020 luminiscence type Methods 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000003107 substituted aryl group Chemical group 0.000 claims description 9
- 150000001413 amino acids Chemical class 0.000 claims description 5
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 5
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims description 2
- 238000001727 in vivo Methods 0.000 claims description 2
- 239000000758 substrate Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 230000009261 transgenic effect Effects 0.000 claims description 2
- 229910004013 NO 2 Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 150000001720 carbohydrates Chemical class 0.000 description 7
- 235000000346 sugar Nutrition 0.000 description 4
- 150000008163 sugars Chemical class 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical group CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 235000021309 simple sugar Nutrition 0.000 description 2
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- UGJBHEZMOKVTIM-UHFFFAOYSA-N N-formylglycine Chemical compound OC(=O)CNC=O UGJBHEZMOKVTIM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- IAJILQKETJEXLJ-QTBDOELSSA-N aldehydo-D-glucuronic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-QTBDOELSSA-N 0.000 description 1
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229940097043 glucuronic acid Drugs 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 150000002772 monosaccharides Chemical group 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40941310P | 2010-11-02 | 2010-11-02 | |
| US61/409,413 | 2010-11-02 | ||
| PCT/US2011/058924 WO2012061477A1 (en) | 2010-11-02 | 2011-11-02 | Coelenterazine derivatives and methods of using same |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013544242A JP2013544242A (ja) | 2013-12-12 |
| JP2013544242A5 true JP2013544242A5 (enExample) | 2016-11-10 |
| JP6040157B2 JP6040157B2 (ja) | 2016-12-07 |
Family
ID=44999921
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013537779A Active JP6040157B2 (ja) | 2010-11-02 | 2011-11-02 | セレンテラジン誘導体およびその使用方法 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US9487520B2 (enExample) |
| EP (1) | EP2635583B1 (enExample) |
| JP (1) | JP6040157B2 (enExample) |
| KR (1) | KR101968475B1 (enExample) |
| CN (1) | CN103180324A (enExample) |
| AU (1) | AU2011323455B2 (enExample) |
| BR (1) | BR112013010484B1 (enExample) |
| CA (1) | CA2815381C (enExample) |
| DK (1) | DK2635583T3 (enExample) |
| ES (1) | ES2543913T3 (enExample) |
| IL (1) | IL225869A (enExample) |
| PL (1) | PL2635583T3 (enExample) |
| PT (1) | PT2635583E (enExample) |
| SG (1) | SG189494A1 (enExample) |
| WO (1) | WO2012061477A1 (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2635583B1 (en) | 2010-11-02 | 2015-06-03 | Promega Corporation | Coelenterazine derivatives and methods of using same |
| AU2011323418B2 (en) | 2010-11-02 | 2017-07-27 | Promega Corporation | Novel coelenterazine substrates and methods of use |
| WO2013033515A1 (en) * | 2011-09-02 | 2013-03-07 | Promega Corporation | Compounds and methods for assaying redox state of metabolically active cells and methods for measuring nad(p)/nad(p)h |
| WO2014052653A1 (en) | 2012-09-26 | 2014-04-03 | Promega Corporation | Real-time monitoring |
| CN105407723A (zh) | 2013-03-15 | 2016-03-16 | G1治疗公司 | 高效的抗赘生剂和抗增生剂 |
| WO2014144326A1 (en) | 2013-03-15 | 2014-09-18 | G1 Therapeutics, Inc. | Transient protection of normal cells during chemotherapy |
| JP6270127B2 (ja) * | 2014-01-17 | 2018-01-31 | 国立研究開発法人物質・材料研究機構 | ニコチンアデニンジヌクレオチド誘導体を検出する方法 |
| US9927430B2 (en) | 2014-01-29 | 2018-03-27 | Promega Corporation | Pro-substrates for live cell applications |
| JP6703484B2 (ja) * | 2014-01-29 | 2020-06-03 | プロメガ コーポレイションＰｒｏｍｅｇａ Ｃｏｒｐｏｒａｔｉｏｎ | 細胞による取り込み測定のための、標識用試薬としての、キノンでマスクされたプローブ |
| EP3313846B1 (en) | 2015-06-25 | 2020-05-06 | Promega Corporation | Thienopyrrole compounds and uses thereof as inhibitors of oplophorus-derived luciferases |
| US9924073B2 (en) * | 2016-02-15 | 2018-03-20 | Promega Corporation | Substituted imidazo[1,2-a]pyrazines as luciferase substrates and preparation method thereof |
| EP3490991B1 (en) | 2016-07-28 | 2021-01-06 | Promega Corporation | Coelenterazine analogues |
| US10316070B2 (en) | 2016-09-09 | 2019-06-11 | Promega Corporation | Dual protected pro-coelenterazine substrates |
| JP7200102B2 (ja) | 2016-11-01 | 2023-01-06 | プロメガ コーポレイション | エネルギー受容体に係留されたセレンテラジン類縁体 |
| DK3548492T5 (en) | 2016-12-01 | 2024-08-05 | Promega Corp | Cell impermeable coelenterazine analogues |
| JP7161475B2 (ja) | 2016-12-28 | 2022-10-26 | プロメガ コーポレイション | 官能化ｎａｎｏｌｕｃ阻害剤 |
| EP3395803A1 (en) * | 2017-04-28 | 2018-10-31 | Institut Pasteur | Imidazopyrazine derivatives, process for preparation thereof, and their uses as luciferins |
| WO2019213119A1 (en) | 2018-05-01 | 2019-11-07 | Promega Corporation | Coelenterazine compounds as nanoluc suicide substrates |
| US11390599B2 (en) | 2018-06-01 | 2022-07-19 | Promega Corporation | Inhibitors of oplophorus luciferase-derived bioluminescent complexes |
| KR102114088B1 (ko) * | 2018-09-10 | 2020-06-17 | (주)신우에이엔티 | 웨이퍼 세정용 나노 버블 분사 구조 |
| CN119955899A (zh) | 2018-10-03 | 2025-05-09 | 普洛麦格公司 | 用于稳定腔肠素及其类似物和衍生物的组合物、方法和试剂盒 |
| BR112022010153A2 (pt) | 2019-11-27 | 2022-08-09 | Promega Corp | Peptídeos, ácido nucleico, polipeptídeo, composição, complexo bioluminescente, métodos, dipeptídeo, sistema e kit |
| EP4073512B1 (en) | 2019-12-10 | 2025-11-12 | Promega Corporation | Compositions and methods for bioluminescent detection using multifunctional probes |
Family Cites Families (73)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3477549D1 (en) | 1983-08-17 | 1989-05-11 | Allied Signal Inc | Gas generator and method of generating gas |
| JP3012274B2 (ja) * | 1989-03-22 | 2000-02-21 | 日本臓器製薬株式会社 | 新規ルシフェリン誘導体 |
| US5683888A (en) | 1989-07-22 | 1997-11-04 | University Of Wales College Of Medicine | Modified bioluminescent proteins and their use |
| US5368484A (en) | 1992-05-22 | 1994-11-29 | Atari Games Corp. | Vehicle simulator with realistic operating feedback |
| DE69535744T2 (de) | 1994-01-03 | 2009-07-02 | Promega Corp., Madison | Mutierte luziferasen |
| US6387675B1 (en) | 1994-01-03 | 2002-05-14 | Promega Corporation | Mutant luciferases |
| GB9501170D0 (en) | 1994-03-23 | 1995-03-08 | Secr Defence | Luciferases |
| JP3648763B2 (ja) * | 1994-08-23 | 2005-05-18 | 日本油脂株式会社 | ウミホタルルシフェリン誘導体および糖加水分解酵素の定量方法 |
| GB9417593D0 (en) | 1994-09-01 | 1994-10-19 | Secr Defence | Luciferase labelling method |
| US5670356A (en) | 1994-12-12 | 1997-09-23 | Promega Corporation | Modified luciferase |
| JP4342608B2 (ja) | 1995-01-20 | 2009-10-14 | スリーエム イノベイティブ プロパティーズ カンパニー | 突然変異体ルシフェラーゼ |
| JPH08294397A (ja) | 1995-04-27 | 1996-11-12 | Nippon Oil & Fats Co Ltd | 免疫学的活性物質の測定方法 |
| US6522361B2 (en) | 1996-03-08 | 2003-02-18 | Sony Corporation | Electronic apparatus having the function of displaying the battery residual quantity and method for displaying the battery residual quantity |
| JP4026876B2 (ja) * | 1996-09-05 | 2007-12-26 | 日本食品化工株式会社 | 発光性シクロデキストリン誘導体及びその製造方法 |
| US5998204A (en) | 1997-03-14 | 1999-12-07 | The Regents Of The University Of California | Fluorescent protein sensors for detection of analytes |
| GB9707486D0 (en) | 1997-04-11 | 1997-05-28 | Secr Defence | Enzyme assays |
| WO1998046739A1 (fr) | 1997-04-16 | 1998-10-22 | Juridical Foundation The Chemo-Sero-Therapeutic Research Institute | Molecules immunomodulatrices et leur procede de production |
| US6602677B1 (en) | 1997-09-19 | 2003-08-05 | Promega Corporation | Thermostable luciferases and methods of production |
| JP4537573B2 (ja) | 1997-09-19 | 2010-09-01 | プロメガ・コーポレイシヨン | 熱安定ルシフェラーゼと生産方法 |
| GB9823468D0 (en) | 1998-10-28 | 1998-12-23 | Secr Defence | Novel enzyme |
| JP3694181B2 (ja) | 1999-01-05 | 2005-09-14 | キッコーマン株式会社 | 変異型ルシフェラーゼ、変異型ルシフェラーゼ遺伝子、新規な組み換え体ｄｎａ及び変異型ルシフェラーゼの製造法 |
| GB9925161D0 (en) | 1999-10-26 | 1999-12-22 | Secr Defence | Novel enzyme |
| EP1224294B1 (en) | 1999-10-26 | 2007-10-03 | The Secretary of State for Defence | Mutant luciferase |
| US20010046687A1 (en) | 2000-03-31 | 2001-11-29 | Dicesare Joseph L. | Method for the enhancement of luminescence intensity from a reaction between adenosine triphosphate (ATP) and a luciferase/luciferin reactant system |
| EP1156103B1 (en) | 2000-04-26 | 2010-08-11 | Chisso Corporation | Oplophorus luciferase |
| JP4613441B2 (ja) | 2000-04-26 | 2011-01-19 | チッソ株式会社 | 新規ルシフェラーゼおよび発光蛋白質 |
| US7118878B1 (en) | 2000-06-09 | 2006-10-10 | Promega Corporation | Method for increasing luminescence assay sensitivity |
| US7879540B1 (en) | 2000-08-24 | 2011-02-01 | Promega Corporation | Synthetic nucleic acid molecule compositions and methods of preparation |
| WO2002022854A2 (en) | 2000-09-13 | 2002-03-21 | Merck Patent Gmbh | Method for the detection and measurement of biomass |
| US7268229B2 (en) | 2001-11-02 | 2007-09-11 | Promega Corporation | Compounds to co-localize luminophores with luminescent proteins |
| EP1472238B1 (en) | 2002-02-01 | 2012-07-04 | Promega Corporation | Bioluminescent protease assay |
| ATE513838T1 (de) | 2002-09-20 | 2011-07-15 | Promega Corp | Auf lumineszenz basierende verfahren und sonden zur messung der cytochrom-p450-aktivität |
| ES2237643T3 (es) * | 2002-10-21 | 2005-08-01 | Axxam S.R.L. | Fotoproteina con bioluminiscencia mejorada. |
| JP4485470B2 (ja) | 2002-12-23 | 2010-06-23 | プロメガ コーポレイション | ルシフェラーゼ酵素活性を保護するための方法及びキット |
| DE10303265A1 (de) | 2003-01-28 | 2004-07-29 | Roche Diagnostics Gmbh | Fluorimetrische Bestimmung von Analyten durch ein intramolekulares Quencher-Fluorophor-Konjugat |
| EP1594962B1 (en) | 2003-01-31 | 2014-08-27 | Promega Corporation | Covalent tethering of functional groups to proteins |
| US7429472B2 (en) | 2003-01-31 | 2008-09-30 | Promega Corporation | Method of immobilizing a protein or molecule via a mutant dehalogenase that is bound to an immobilized dehalogenase substrate and linked directly or indirectly to the protein or molecule |
| EP1592805A1 (en) | 2003-02-12 | 2005-11-09 | Promega Corporation | Methods and kits for dual enzymatic assays whereby light is quenched from luminescent reactions |
| US20040178545A1 (en) | 2003-03-14 | 2004-09-16 | Cates Larry E. | System for optically analyzing a molten metal bath |
| EP2298902B1 (en) | 2003-10-10 | 2015-04-22 | Promega Corporation | Luciferase biosensor |
| WO2005068483A1 (en) | 2004-01-08 | 2005-07-28 | Universität Zürich | Metal complexes having vitamin b12 as a ligand |
| US7416854B2 (en) * | 2004-01-22 | 2008-08-26 | Promega Corporation | Luminogenic and nonluminogenic multiplex assay |
| US7553632B2 (en) | 2004-01-22 | 2009-06-30 | Promega Corporation | Luminogenic and nonluminogenic multiplex assay |
| EP3179252B1 (en) | 2004-07-30 | 2018-11-14 | Promega Corporation | Covalent tethering of functional groups to proteins and substrates therefor |
| US20070087400A1 (en) | 2004-07-30 | 2007-04-19 | Aldis Darzins | Covalent tethering of functional groups to proteins and substrates therefor |
| US7425436B2 (en) | 2004-07-30 | 2008-09-16 | Promega Corporation | Covalent tethering of functional groups to proteins and substrates therefor |
| US7728118B2 (en) | 2004-09-17 | 2010-06-01 | Promega Corporation | Synthetic nucleic acid molecule compositions and methods of preparation |
| JP4453528B2 (ja) * | 2004-10-26 | 2010-04-21 | 東京化成工業株式会社 | 新規化学発光試薬 |
| EP1700865A1 (en) | 2005-03-11 | 2006-09-13 | AXXAM S.r.l. | Photoproteins with enhanced bioluminescence and their use as intracellular calcium indicators |
| JP4639904B2 (ja) | 2005-03-30 | 2011-02-23 | チッソ株式会社 | 蛍光活性を有するルシフェラーゼの活性増強方法 |
| JP3844082B2 (ja) | 2005-04-08 | 2006-11-08 | キッコーマン株式会社 | 耐熱性ホタルルシフェラーゼ、耐熱性ホタルルシフェラーゼ遺伝子、新規な組み換え体ｄｎａ及び耐熱性ホタルルシフェラーゼの製造法 |
| EP1935986B1 (en) | 2005-05-31 | 2014-04-16 | Promega Corporation | Luminogenic and fluorogenic compounds and methods to detect molecules or conditions |
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| MX2008002123A (es) * | 2005-08-17 | 2008-04-17 | Yeda Res & Dev | Metodos y composiciones para determinar un nivel de paraoxonasa de suero biologicamente activa. |
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| JP5684984B2 (ja) | 2006-04-03 | 2015-03-18 | プロメガ コーポレイションＰｒｏｍｅｇａ Ｃｏｒｐｏｒａｔｉｏｎ | 順列置換及び非順列置換ルシフェラーゼバイオセンサー |
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| CA2667697A1 (en) | 2006-10-30 | 2008-05-08 | Promega Corporation | Mutant hydrolase proteins with enhanced kinetics and functional expression |
| WO2008086035A2 (en) | 2007-01-10 | 2008-07-17 | Promega Corporation | Split mutant hydrolase fusion reporter and uses thereof |
| WO2008118445A1 (en) | 2007-03-26 | 2008-10-02 | Promega Corporation | Methods to quench light from optical reactions |
| EP2215227A2 (en) | 2007-11-05 | 2010-08-11 | Promega Corporation | Hybrid fusion reporter and uses thereof |
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| TWI354101B (en) | 2008-08-19 | 2011-12-11 | Univ Nat Taipei Technology | Fluorimetric indicator for biosensing and manufact |
| EP2420573A1 (en) | 2009-04-17 | 2012-02-22 | National Institute of Advanced Industrial Science And Technology | Stable artificial bioluminescent enzyme having super-high brightness |
| KR101665352B1 (ko) | 2009-05-01 | 2016-10-12 | 프로메가 코포레이션 | 광 출력이 향상된 합성 오플로포러스 루시퍼라제 |
| WO2011038219A1 (en) | 2009-09-24 | 2011-03-31 | Promega Corporation | Proteases having improved stability, solubility and activity |
| EP2569423B1 (en) | 2010-05-11 | 2015-12-02 | Promega Corporation | Mutant protease biosensors with enhanced detection characteristics |
| EP2611929B1 (en) | 2010-09-01 | 2016-01-13 | Promega Corporation | Oxidized glutathione assay |
| US9284188B2 (en) | 2010-09-03 | 2016-03-15 | The Regents Of The University Of California | Cytosolic delivery of materials with endosome-disrupting colloids |
| EP2635583B1 (en) | 2010-11-02 | 2015-06-03 | Promega Corporation | Coelenterazine derivatives and methods of using same |
| AU2011323418B2 (en) | 2010-11-02 | 2017-07-27 | Promega Corporation | Novel coelenterazine substrates and methods of use |
| WO2013033515A1 (en) | 2011-09-02 | 2013-03-07 | Promega Corporation | Compounds and methods for assaying redox state of metabolically active cells and methods for measuring nad(p)/nad(p)h |
-
2011
- 2011-11-02 EP EP11785217.8A patent/EP2635583B1/en active Active
- 2011-11-02 KR KR1020137014031A patent/KR101968475B1/ko active Active
- 2011-11-02 AU AU2011323455A patent/AU2011323455B2/en active Active
- 2011-11-02 ES ES11785217.8T patent/ES2543913T3/es active Active
- 2011-11-02 CA CA2815381A patent/CA2815381C/en active Active
- 2011-11-02 WO PCT/US2011/058924 patent/WO2012061477A1/en not_active Ceased
- 2011-11-02 PL PL11785217T patent/PL2635583T3/pl unknown
- 2011-11-02 PT PT117852178T patent/PT2635583E/pt unknown
- 2011-11-02 JP JP2013537779A patent/JP6040157B2/ja active Active
- 2011-11-02 CN CN201180052806XA patent/CN103180324A/zh active Pending
- 2011-11-02 DK DK11785217.8T patent/DK2635583T3/en active
- 2011-11-02 BR BR112013010484A patent/BR112013010484B1/pt active IP Right Grant
- 2011-11-02 US US13/287,519 patent/US9487520B2/en active Active
- 2011-11-02 SG SG2013030317A patent/SG189494A1/en unknown
-
2013
- 2013-04-21 IL IL225869A patent/IL225869A/en active IP Right Grant
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