JP6588917B2 - 生細胞への適用のためのプロ基質 - Google Patents

生細胞への適用のためのプロ基質 Download PDF

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JP6588917B2
JP6588917B2 JP2016549241A JP2016549241A JP6588917B2 JP 6588917 B2 JP6588917 B2 JP 6588917B2 JP 2016549241 A JP2016549241 A JP 2016549241A JP 2016549241 A JP2016549241 A JP 2016549241A JP 6588917 B2 JP6588917 B2 JP 6588917B2
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compound
group
cell
protein
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JP2017506622A5 (enExample
JP2017506622A (ja
Inventor
ウェンフイ チョウ
ウェンフイ チョウ
ブロック ビンコフスキー
ブロック ビンコフスキー
フイ ワン
フイ ワン
ブレーデン バトラー
ブレーデン バトラー
トーマス マヒライド
トーマス マヒライド
キース ウッド
キース ウッド
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Promega Corp
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Promega Corp
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    • GPHYSICS
    • G01MEASURING; TESTING
    • G01NINVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/53Immunoassay; Biospecific binding assay; Materials therefor
    • G01N33/536Immunoassay; Biospecific binding assay; Materials therefor with immune complex formed in liquid phase
    • G01N33/542Immunoassay; Biospecific binding assay; Materials therefor with immune complex formed in liquid phase with steric inhibition or signal modification, e.g. fluorescent quenching
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D487/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02Heterocyclic 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
    • C07D487/04Ortho-condensed systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K5/00Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06Dipeptides
    • C07K5/06104Dipeptides with the first amino acid being acidic
    • C07K5/06113Asp- or Asn-amino acid
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K5/00Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/08Tripeptides
    • C07K5/0819Tripeptides with the first amino acid being acidic
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K5/00Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/10Tetrapeptides
    • C07K5/1021Tetrapeptides with the first amino acid being acidic
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12QMEASURING 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
    • C12Q1/00Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
    • C12Q1/66Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving luciferase
    • GPHYSICS
    • G01MEASURING; TESTING
    • G01NINVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/68Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving proteins, peptides or amino acids
    • G01N33/6803General methods of protein analysis not limited to specific proteins or families of proteins
    • G01N33/6845Methods of identifying protein-protein interactions in protein mixtures

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Immunology (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Medicinal Chemistry (AREA)
  • Biophysics (AREA)
  • Hematology (AREA)
  • Biomedical Technology (AREA)
  • Urology & Nephrology (AREA)
  • Physics & Mathematics (AREA)
  • Genetics & Genomics (AREA)
  • Biotechnology (AREA)
  • Microbiology (AREA)
  • Analytical Chemistry (AREA)
  • Pathology (AREA)
  • Food Science & Technology (AREA)
  • General Physics & Mathematics (AREA)
  • Cell Biology (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Bioinformatics & Computational Biology (AREA)
  • General Engineering & Computer Science (AREA)
  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
  • Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
  • Enzymes And Modification Thereof (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
JP2016549241A 2014-01-29 2015-01-29 生細胞への適用のためのプロ基質 Active JP6588917B2 (ja)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201461933210P 2014-01-29 2014-01-29
US61/933,210 2014-01-29
PCT/US2015/013504 WO2015116806A1 (en) 2014-01-29 2015-01-29 Pro-substrates for live cell applications

Publications (3)

Publication Number Publication Date
JP2017506622A JP2017506622A (ja) 2017-03-09
JP2017506622A5 JP2017506622A5 (enExample) 2018-03-08
JP6588917B2 true JP6588917B2 (ja) 2019-10-09

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JP2016549241A Active JP6588917B2 (ja) 2014-01-29 2015-01-29 生細胞への適用のためのプロ基質

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US (1) US9927430B2 (enExample)
EP (1) EP3099691B1 (enExample)
JP (1) JP6588917B2 (enExample)
WO (1) WO2015116806A1 (enExample)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9927430B2 (en) 2014-01-29 2018-03-27 Promega Corporation Pro-substrates for live cell applications
WO2015116867A1 (en) 2014-01-29 2015-08-06 Promega Corporation Quinone-masked probes as labeling reagents for cell uptake measurements
US10513694B2 (en) 2015-06-25 2019-12-24 Promega Corporation Thienopyrrole compounds and uses thereof
JP7092677B2 (ja) 2016-02-15 2022-06-28 プロメガ コーポレイション セレンテラジン類似体
JP6978492B2 (ja) * 2016-09-09 2021-12-08 プロメガ コーポレイションPromega Corporation 二重保護されたプロセレンテラジン基質
JP7139330B2 (ja) 2016-12-01 2022-09-20 プロメガ コーポレイション 細胞不透過性セレンテラジンアナログ
WO2018125992A1 (en) 2016-12-28 2018-07-05 Promega Corporation Functionalized nanoluc inhibitors
EP3395803A1 (en) * 2017-04-28 2018-10-31 Institut Pasteur Imidazopyrazine derivatives, process for preparation thereof, and their uses as luciferins
JP7419260B2 (ja) 2018-05-01 2024-01-22 プロメガ コーポレイション NanoLuc自殺基質としてのセレンテラジン化合物
WO2019232384A1 (en) 2018-06-01 2019-12-05 Promega Corporation Inhibitors of oplophorus luciferase-derived bioluminescent complexes
BR112021006298A2 (pt) 2018-10-03 2021-07-06 Promega Corp composições e métodos para estabilizar coelenterazina e análogos e derivados da mesma
JP7599074B2 (ja) 2019-04-16 2024-12-13 マックス-プランク-ゲゼルシャフト ツール フェルデルンク デル ヴィッセンシャフテン エー.ファウ. 円順列変異ハロアルカントランスフェラーゼ融合分子
EP3816180A1 (en) 2019-10-31 2021-05-05 Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. Circularly permutated haloalkane transferase fusion molecules

Family Cites Families (65)

* Cited by examiner, † Cited by third party
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
US5683888A (en) 1989-07-22 1997-11-04 University Of Wales College Of Medicine Modified bioluminescent proteins and their use
ES2301160T3 (es) 1994-01-03 2008-06-16 Promega Corporation Luciferasas mutantes.
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
AU707243B2 (en) 1995-01-20 1999-07-08 Promega Corporation Mutant luciferases
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
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
US6429286B1 (en) 1997-04-16 2002-08-06 Juridical Foundation The Chemo-Sero-Therapeutic Research Institute Immunoregulatory molecules for costimulatory signal transduction
US6602677B1 (en) 1997-09-19 2003-08-05 Promega Corporation Thermostable luciferases and methods of production
WO1999014336A2 (en) 1997-09-19 1999-03-25 Promega Corporation Thermostable luciferases and methods of production
GB9823468D0 (en) 1998-10-28 1998-12-23 Secr Defence Novel enzyme
ATE374820T1 (de) 1999-10-26 2007-10-15 Secr Defence Mutantenluciferase
GB9925161D0 (en) 1999-10-26 1999-12-22 Secr Defence Novel enzyme
DE60142761D1 (de) 2000-04-26 2010-09-23 Chisso Corp Oplophorus Luciferase
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
CA2474695A1 (en) 2002-02-01 2003-08-14 Promega Corporation Bioluminescent protease assay
AU2003267245C1 (en) 2002-09-20 2008-05-29 Promega Corporation Luminescence-based methods and probes for measuring cytochrome P450 activity
EP1413584B1 (en) 2002-10-21 2005-03-02 AXXAM S.r.l. Photoprotein with improved bioluminescence
AU2003300008B2 (en) 2002-12-23 2007-04-05 Promega Corporation Improved luciferase-based assays
DE10303265A1 (de) 2003-01-28 2004-07-29 Roche Diagnostics Gmbh Fluorimetrische Bestimmung von Analyten durch ein intramolekulares Quencher-Fluorophor-Konjugat
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
EP1594962B1 (en) 2003-01-31 2014-08-27 Promega Corporation Covalent tethering of functional groups to proteins
AU2004210982B2 (en) 2003-02-12 2008-12-18 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
US7922891B2 (en) 2003-05-23 2011-04-12 Arizona Board Of Regents Methods for detection and quantification of analytes
WO2005038029A2 (en) 2003-10-10 2005-04-28 Promega Corporation Luciferase biosensor
ATE443070T1 (de) 2004-01-08 2009-10-15 Univ Zuerich Metallkomplexe mit vitamin b12 als 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
EP2395358B1 (en) 2004-07-30 2017-03-29 Promega Corporation Covalent tethering of functional groups to proteins
US7425436B2 (en) 2004-07-30 2008-09-16 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
US7728118B2 (en) 2004-09-17 2010-06-01 Promega Corporation Synthetic nucleic acid molecule compositions and methods of preparation
EP2272973B1 (en) 2005-05-31 2015-05-27 Promega Corporation Luminogenic and fluorogenic compounds and methods to detect molecules or conditions
EP1935986B1 (en) 2005-05-31 2014-04-16 Promega Corporation Luminogenic and fluorogenic compounds and methods to detect molecules or conditions
KR20080039431A (ko) 2005-08-17 2008-05-07 예다 리서치 앤드 디벨럽먼트 캄파니 리미티드 생물학적으로 활성인 혈청 파라옥소나제의 수준을 구하기위한 방법 및 조성물
EP2004813B1 (en) 2006-04-03 2015-06-03 Promega Corporation Permuted and nonpermuted luciferase biosensors binding cyclic nucleotides
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
US20080248511A1 (en) 2007-03-26 2008-10-09 Promega Corporation Methods to quench light from optical reactions
WO2009061413A2 (en) 2007-11-05 2009-05-14 Promega Corporation Hybrid fusion reporter and uses thereof
EP2281046B1 (en) 2008-05-19 2012-01-25 Promega Corporation LUCIFERASE BIOSENSORS FOR cAMP
JP5753083B2 (ja) 2008-07-22 2015-07-22 プロメガ コーポレイションPromega Corporation Adp検出に基づく発光ホスホトランスフェラーゼまたはatpヒドロラーゼのアッセイ法
TWI354101B (en) 2008-08-19 2011-12-11 Univ Nat Taipei Technology Fluorimetric indicator for biosensing and manufact
DK2456864T3 (en) 2009-05-01 2015-12-21 Promega Corp SYNTHETIC OPLOPHORUS luciferases WITH IMPROVED LIGHT MISSION
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
WO2011146390A2 (en) * 2010-05-17 2011-11-24 The Regents Of The University Of California Compositions and methods for in vivo imaging
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
US8632992B2 (en) 2010-09-10 2014-01-21 Promega Corporation Methods for assaying enzyme activities
PT2635583E (pt) 2010-11-02 2015-09-11 Promega Corp Derivados da coelenterazina e métodos de utilização da mesma
US8669103B2 (en) 2010-11-02 2014-03-11 Promega Corporation Oplophorus-derived luciferases, novel coelenterazine substrates, and methods of use
EP2751089B1 (en) 2011-09-02 2018-11-14 Promega Corporation Compounds and methods for assaying redox state of metabolically active cells and methods for measuring nad(p)/nad(p)h
EP2900833B1 (en) * 2012-09-26 2018-05-30 Promega Corporation Real-time monitoring
US9927430B2 (en) 2014-01-29 2018-03-27 Promega Corporation Pro-substrates for live cell applications
WO2015116867A1 (en) 2014-01-29 2015-08-06 Promega Corporation Quinone-masked probes as labeling reagents for cell uptake measurements

Also Published As

Publication number Publication date
WO2015116806A1 (en) 2015-08-06
US9927430B2 (en) 2018-03-27
US20150212078A1 (en) 2015-07-30
EP3099691B1 (en) 2019-11-20
EP3099691A1 (en) 2016-12-07
JP2017506622A (ja) 2017-03-09

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