CA2462506C - Compositions, methods and kits pertaining to luminescent compounds - Google Patents
Compositions, methods and kits pertaining to luminescent compounds Download PDFInfo
- Publication number
- CA2462506C CA2462506C CA2462506A CA2462506A CA2462506C CA 2462506 C CA2462506 C CA 2462506C CA 2462506 A CA2462506 A CA 2462506A CA 2462506 A CA2462506 A CA 2462506A CA 2462506 C CA2462506 C CA 2462506C
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- Prior art keywords
- heteroalkyl
- alkyl
- aryl
- independently
- compound
- 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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- 239000000203 mixture Substances 0.000 title claims abstract description 59
- 238000000034 method Methods 0.000 title claims abstract description 55
- 150000001875 compounds Chemical class 0.000 title claims description 93
- YHIPILPTUVMWQT-UHFFFAOYSA-N Oplophorus luciferin Chemical class C1=CC(O)=CC=C1CC(C(N1C=C(N2)C=3C=CC(O)=CC=3)=O)=NC1=C2CC1=CC=CC=C1 YHIPILPTUVMWQT-UHFFFAOYSA-N 0.000 claims abstract description 120
- 108090000623 proteins and genes Proteins 0.000 claims abstract description 54
- 102000004169 proteins and genes Human genes 0.000 claims abstract description 51
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- 239000005089 Luciferase Substances 0.000 claims abstract description 30
- 230000002255 enzymatic effect Effects 0.000 claims abstract description 5
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 69
- 125000000217 alkyl group Chemical group 0.000 claims description 67
- 125000003118 aryl group Chemical group 0.000 claims description 63
- -1 acyloxymethyl ether Chemical compound 0.000 claims description 60
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- 238000004020 luminiscence type Methods 0.000 claims description 46
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- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 22
- 150000002148 esters Chemical class 0.000 claims description 20
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 13
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- CJIIERPDFZUYPI-UHFFFAOYSA-N oxidized Oplophorus luciferin Chemical compound C1=CC(O)=CC=C1CC(=O)NC1=NC=C(C=2C=CC(O)=CC=2)N=C1CC1=CC=CC=C1 CJIIERPDFZUYPI-UHFFFAOYSA-N 0.000 description 4
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- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
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- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 2
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- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
- G01N33/531—Production of immunochemical test materials
- G01N33/532—Production of labelled immunochemicals
- G01N33/533—Production of labelled immunochemicals with fluorescent label
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
- C12Q1/66—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving luciferase
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
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- Molecular Biology (AREA)
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- Biomedical Technology (AREA)
- General Physics & Mathematics (AREA)
- Biophysics (AREA)
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- Cell Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- Pathology (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Luminescent Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Farming Of Fish And Shellfish (AREA)
- Decoration By Transfer Pictures (AREA)
- Electroluminescent Light Sources (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/053,482 US7268229B2 (en) | 2001-11-02 | 2001-11-02 | Compounds to co-localize luminophores with luminescent proteins |
| US10/053,482 | 2001-11-02 | ||
| PCT/US2002/034972 WO2003040100A1 (en) | 2001-11-02 | 2002-11-01 | Compositions, methods and kits pertaining to luminescent compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2462506A1 CA2462506A1 (en) | 2003-05-15 |
| CA2462506C true CA2462506C (en) | 2010-04-06 |
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|---|---|---|---|
| CA2462506A Expired - Fee Related CA2462506C (en) | 2001-11-02 | 2002-11-01 | Compositions, methods and kits pertaining to luminescent compounds |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US7268229B2 (https=) |
| EP (2) | EP1894933B1 (https=) |
| JP (1) | JP4958388B2 (https=) |
| CN (2) | CN101440089A (https=) |
| AT (1) | ATE399784T1 (https=) |
| CA (1) | CA2462506C (https=) |
| DE (1) | DE60227408D1 (https=) |
| DK (1) | DK1451155T3 (https=) |
| ES (1) | ES2307829T3 (https=) |
| WO (1) | WO2003040100A1 (https=) |
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| EP1546162B1 (en) | 2002-09-20 | 2011-06-22 | Promega Corporation | Luminescence-based methods and probes for measuring cytochrome p450 activity |
| 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 |
| EP2272972A1 (en) | 2005-05-31 | 2011-01-12 | Promega Corporation | Luminogenic and fluorogenic compounds and methods to detect molecules or conditions |
| US7709468B2 (en) | 2005-09-02 | 2010-05-04 | Abbott Laboratories | Imidazo based heterocycles |
| JP2007081050A (ja) * | 2005-09-13 | 2007-03-29 | Fujifilm Corp | 有機電界発光素子 |
| JP4982737B2 (ja) * | 2006-03-23 | 2012-07-25 | 国立大学法人三重大学 | イミダゾキノキザリノン化学発光物質、その製造法、および発光分析法 |
| JP2007277097A (ja) * | 2006-04-03 | 2007-10-25 | Mie Univ | 発光化合物、発光方法、及びその製造方法 |
| US7709253B2 (en) * | 2006-08-04 | 2010-05-04 | The Board Of Trustees Of The Leland Stanford Junior University | Ligand-regulable transactivation systems, methods of use thereof, methods of detecting estrogen receptor ligands, and methods of differentiating estrogen receptor ligand agonists and antagonists |
| JP5844029B2 (ja) * | 2006-10-24 | 2016-01-13 | ジーン ストリーム ピーティーワイ エルティーディ | ルシフェラーゼシグナルを増強する組成物 |
| US20090075309A1 (en) * | 2007-09-06 | 2009-03-19 | Gambhir Sanjiv S | Bisdeoxycoelenterazine derivatives, methods of use, and BRET2 systems |
| EP2326953B1 (en) | 2008-07-22 | 2018-03-21 | Promega Corporation | Adp detection based luminescent phosphotransferase or atp hydrolase assay |
| US8288559B2 (en) | 2008-08-18 | 2012-10-16 | Promega Corporation | Luminogenic compounds and methods to detect cytochrome P450 3A enzymes |
| WO2010090319A1 (ja) | 2009-02-09 | 2010-08-12 | チッソ株式会社 | セレンテラジン類縁体及びその製造方法 |
| ES2795287T3 (es) | 2009-05-01 | 2020-11-23 | Promega Corp | Luciferasas de Oplophorus sintéticas con mayor emisión de luz |
| JP5605727B2 (ja) * | 2010-04-06 | 2014-10-15 | Ｊｎｃ株式会社 | セレンテラジン類縁体及びセレンテラミド類縁体 |
| SG185481A1 (en) | 2010-05-10 | 2012-12-28 | Univ California | Endoribonuclease compositions and methods of use thereof |
| CN103180324A (zh) * | 2010-11-02 | 2013-06-26 | 普罗美加公司 | 腔肠素衍生物及其使用方法 |
| SG10202103336SA (en) | 2010-11-02 | 2021-04-29 | Promega Corp | Novel coelenterazine substrates and methods of use |
| JP6067019B2 (ja) * | 2011-09-02 | 2017-01-25 | プロメガ コーポレイションＰｒｏｍｅｇａ Ｃｏｒｐｏｒａｔｉｏｎ | 代謝的に活性な細胞の酸化還元状態を評価するための化合物及び方法、ならびにｎａｄ（ｐ）／ｎａｄ（ｐ）ｈを測定するための方法 |
| JP6511720B2 (ja) | 2013-02-28 | 2019-05-15 | Jnc株式会社 | コドン最適化変異エビルシフェラーゼ遺伝子およびその使用方法 |
| JP6040846B2 (ja) | 2013-04-08 | 2016-12-07 | Jnc株式会社 | セレンテラジン類縁体 |
| JP6484987B2 (ja) | 2013-10-21 | 2019-03-20 | Jnc株式会社 | エビルシフェラーゼの触媒蛋白質の変異遺伝子とその使用法 |
| JP6442825B2 (ja) | 2013-12-26 | 2018-12-26 | Jnc株式会社 | エビルシフェラーゼの触媒蛋白質の変異遺伝子とその使用法 |
| US9790537B2 (en) | 2014-01-29 | 2017-10-17 | Promega Corporation | Quinone-masked probes as labeling reagents for cell uptake measurements |
| EP3099691B1 (en) | 2014-01-29 | 2019-11-20 | Promega Corporation | Pro-substrates for live cell applications |
| JP6265020B2 (ja) | 2014-04-16 | 2018-01-24 | Jnc株式会社 | エビルシフェラーゼの触媒蛋白質の変異遺伝子とその使用法 |
| US9732373B2 (en) * | 2014-09-11 | 2017-08-15 | Promega Corporation | Luciferase sequences utilizing infrared-emitting substrates to produce enhanced luminescence |
| JP6814132B2 (ja) | 2014-09-12 | 2021-01-13 | プロメガ コーポレイションＰｒｏｍｅｇａ Ｃｏｒｐｏｒａｔｉｏｎ | 内部タンパク質タグ |
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2001
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- 2002-11-01 CN CNA2008101694033A patent/CN101440089A/zh active Pending
- 2002-11-01 AT AT02802815T patent/ATE399784T1/de not_active IP Right Cessation
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- 2002-11-01 EP EP07025040.2A patent/EP1894933B1/en not_active Expired - Lifetime
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| ES2307829T3 (es) | 2008-12-01 |
| JP4958388B2 (ja) | 2012-06-20 |
| CA2462506A1 (en) | 2003-05-15 |
| CN101440089A (zh) | 2009-05-27 |
| EP1451155B1 (en) | 2008-07-02 |
| JP2005515977A (ja) | 2005-06-02 |
| EP1451155A1 (en) | 2004-09-01 |
| DK1451155T3 (da) | 2008-11-10 |
| EP1894933A3 (en) | 2008-03-26 |
| US7537912B2 (en) | 2009-05-26 |
| WO2003040100A1 (en) | 2003-05-15 |
| ATE399784T1 (de) | 2008-07-15 |
| EP1451155A4 (en) | 2006-03-01 |
| DE60227408D1 (de) | 2008-08-14 |
| EP1894933B1 (en) | 2013-07-03 |
| US20080050760A1 (en) | 2008-02-28 |
| US7268229B2 (en) | 2007-09-11 |
| EP1894933A2 (en) | 2008-03-05 |
| CN100439338C (zh) | 2008-12-03 |
| CN1612860A (zh) | 2005-05-04 |
| US20030153090A1 (en) | 2003-08-14 |
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