CA2815381C - Coelenterazine derivatives and methods of using same - Google Patents

Coelenterazine derivatives and methods of using same Download PDF

Info

Publication number
CA2815381C
CA2815381C CA2815381A CA2815381A CA2815381C CA 2815381 C CA2815381 C CA 2815381C CA 2815381 A CA2815381 A CA 2815381A CA 2815381 A CA2815381 A CA 2815381A CA 2815381 C CA2815381 C CA 2815381C
Authority
CA
Canada
Prior art keywords
alkyl
coelenterazine
enzyme
substituted
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.)
Active
Application number
CA2815381A
Other languages
English (en)
French (fr)
Other versions
CA2815381A1 (en
Inventor
Dieter H. Klaubert
Poncho Meisenheimer
James Unch
Wenhui Zhou
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Promega Corp
Original Assignee
Promega Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Promega Corp filed Critical Promega Corp
Publication of CA2815381A1 publication Critical patent/CA2815381A1/en
Application granted granted Critical
Publication of CA2815381C publication Critical patent/CA2815381C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • C07H17/02Heterocyclic radicals containing only nitrogen as ring hetero atoms
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • Immunology (AREA)
  • Microbiology (AREA)
  • Analytical Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
  • Peptides Or Proteins (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Saccharide Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
CA2815381A 2010-11-02 2011-11-02 Coelenterazine derivatives and methods of using same Active CA2815381C (en)

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 (2)

Publication Number Publication Date
CA2815381A1 CA2815381A1 (en) 2012-05-10
CA2815381C true CA2815381C (en) 2019-03-19

Family

ID=44999921

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2815381A Active CA2815381C (en) 2010-11-02 2011-11-02 Coelenterazine derivatives and methods of using same

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)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2011323418B2 (en) * 2010-11-02 2017-07-27 Promega Corporation Novel coelenterazine substrates and methods of use
JP6040157B2 (ja) 2010-11-02 2016-12-07 プロメガ コーポレイションPromega Corporation セレンテラジン誘導体およびその使用方法
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
WO2014052653A1 (en) 2012-09-26 2014-04-03 Promega Corporation Real-time monitoring
EP2967050A4 (en) 2013-03-15 2016-09-28 G1 Therapeutics Inc HIGH-ACTIVE ANTINEOPLASTIC AND ANTIPROLIFERATIVE AGENTS
US9464092B2 (en) 2013-03-15 2016-10-11 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
WO2015116806A1 (en) * 2014-01-29 2015-08-06 Promega Corporation Pro-substrates for live cell applications
US9790537B2 (en) * 2014-01-29 2017-10-17 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
WO2017142852A1 (en) * 2016-02-15 2017-08-24 Promega Corporation Coelenterazine analogues
JP7212612B2 (ja) 2016-07-28 2023-01-25 プロメガ コーポレイション セレンテラジン類縁体
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
EP3535270B3 (en) 2016-11-01 2024-05-29 Promega Corporation Coelenterazine analogues tethered to energy acceptors
EP3548492B1 (en) * 2016-12-01 2023-07-05 Promega Corporation 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
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
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
EP3861128A2 (en) 2018-10-03 2021-08-11 Promega Corporation Compositions and methods for stabilizing coelenterazine and analogs and derivatives thereof
AU2020392245A1 (en) 2019-11-27 2022-06-23 Promega Corporation Multipartite luciferase peptides and polypeptides
US12061202B2 (en) 2019-12-10 2024-08-13 Promega Corporation Compositions and methods for bioluminescent detection using multifunctional probes

Family Cites Families (73)

* 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
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
WO1995018853A1 (en) 1994-01-03 1995-07-13 Promega Corporation Mutant luciferases
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
CA2210354C (en) 1995-01-20 2008-01-08 The Secretary Of State For Defence 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
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
EP1015601B1 (en) 1997-09-19 2015-01-07 Promega Corporation Thermostable luciferases and methods of production
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
JP5154724B2 (ja) 1999-10-26 2013-02-27 プロメガ コーポレイション 変異型ルシフェラーゼ
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
US20040096927A1 (en) 2000-09-13 2004-05-20 Chittock Roger Steward 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
EP2388254B1 (en) 2002-02-01 2016-08-10 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
DK1413584T3 (da) * 2002-10-21 2005-07-04 Axxam S R L Fotoprotein med forbedret bioluminescens
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
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
EP2341134B1 (en) 2003-01-31 2014-08-27 Promega Corporation Covalent tethering of functional groups to proteins
CA2515217A1 (en) 2003-02-12 2004-08-26 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
EP1673459B1 (en) 2003-10-10 2012-06-27 Promega Corporation Luciferase biosensor
KR20070010119A (ko) 2004-01-08 2007-01-22 유니베르시태트 취리히 리간드로서 비타민 b12를 갖는 금속 착체
US7553632B2 (en) 2004-01-22 2009-06-30 Promega Corporation Luminogenic and nonluminogenic multiplex assay
US7416854B2 (en) 2004-01-22 2008-08-26 Promega Corporation Luminogenic and nonluminogenic multiplex assay
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
EP2395358B1 (en) 2004-07-30 2017-03-29 Promega Corporation Covalent tethering of functional groups to proteins
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
EP2778234B1 (en) 2005-05-31 2017-09-27 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
US20090305239A1 (en) 2005-08-17 2009-12-10 Tawfik Dan S Methods and compositions for determing a level of biologically active serum paraoxonase
JP4999341B2 (ja) 2005-09-06 2012-08-15 株式会社バイオエネックス 変異型ホタルルシフェラーゼ、遺伝子、組換えベクター、形質転換体、及び変異型ホタルルシフェラーゼの製造方法
US9359635B2 (en) 2006-04-03 2016-06-07 Promega Corporation Permuted and nonpermuted luciferase biosensors
EP2087132B1 (en) 2006-10-24 2017-01-25 Gene Stream Pty Ltd. Luciferase signal enhancng compositions
EP2502990B1 (en) 2006-10-30 2015-07-22 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
US9045730B2 (en) 2008-05-19 2015-06-02 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
EP2420573A1 (en) 2009-04-17 2012-02-22 National Institute of Advanced Industrial Science And Technology Stable artificial bioluminescent enzyme having super-high brightness
BRPI1010019B1 (pt) 2009-05-01 2019-02-05 Promega Corp polipeptídeo de luciferase modificada, vetor e kit compreendendo os mesmos
WO2011038219A1 (en) 2009-09-24 2011-03-31 Promega Corporation Proteases having improved stability, solubility and activity
EP2990479B1 (en) 2010-05-11 2019-03-27 Promega Corporation Mutant protease biosensors with enhanced detection characteristics
US9816127B2 (en) 2010-09-01 2017-11-14 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
JP6040157B2 (ja) 2010-11-02 2016-12-07 プロメガ コーポレイションPromega Corporation セレンテラジン誘導体およびその使用方法
AU2011323418B2 (en) 2010-11-02 2017-07-27 Promega Corporation 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

Also Published As

Publication number Publication date
EP2635583B1 (en) 2015-06-03
SG189494A1 (en) 2013-05-31
KR20140003430A (ko) 2014-01-09
BR112013010484A2 (pt) 2016-07-05
CN103180324A (zh) 2013-06-26
KR101968475B1 (ko) 2019-04-15
AU2011323455B2 (en) 2017-07-27
PT2635583E (pt) 2015-09-11
EP2635583A1 (en) 2013-09-11
IL225869A0 (en) 2013-07-31
IL225869A (en) 2017-09-28
WO2012061477A1 (en) 2012-05-10
JP2013544242A (ja) 2013-12-12
AU2011323455A1 (en) 2013-05-30
JP6040157B2 (ja) 2016-12-07
US9487520B2 (en) 2016-11-08
US20120107849A1 (en) 2012-05-03
ES2543913T3 (es) 2015-08-25
BR112013010484B1 (pt) 2019-09-03
PL2635583T3 (pl) 2015-11-30
DK2635583T3 (en) 2015-08-03
CA2815381A1 (en) 2012-05-10

Similar Documents

Publication Publication Date Title
CA2815381C (en) Coelenterazine derivatives and methods of using same
Zou et al. A highly specific ratiometric two-photon fluorescent probe to detect dipeptidyl peptidase IV in plasma and living systems
JP6067019B2 (ja) 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
US9329184B2 (en) Fluorescent probe
JP5597200B2 (ja) ルミネッセンスを生じる化合物およびチトクロムp4503a酵素を検出するための方法
US9868977B2 (en) Red-shifted luciferins and methods of using same
CN116041315A (zh) 检测Vanin-1的化学发光探针及其制备方法与应用
JP6978492B2 (ja) 二重保護されたプロセレンテラジン基質
CN105712987A (zh) 人羧酸酯酶1的生物发光探针底物及其制备方法与应用
JP2018145126A (ja) カルボキシペプチダーゼ活性検出用蛍光プローブ
Takamura et al. A photoaffinity probe that targets folate-binding proteins
Sureshbabu et al. A facile one-pot synthesis of Nα-Z/Boc-protected S-linked 1, 3, 4-oxadiazole tethered peptidomimetics
Brynes et al. Potential antitumor agents via inhibitors of L‐asparagine synthetase: Substituted sulfonamides and sulfonyl hydrazides related to glutamine
Li et al. A bicyclic pentapeptide-based highly potent and selective pan-SIRT1/2/3 inhibitor harboring Nε-thioacetyl-lysine
Liu et al. Exploring boron applications in modern agriculture: A structure-activity relationship study of a novel series of multi-substitution benzoxaboroles for identification of potential fungicides
Guruvelli et al. Synthesis, Screening and Docking Analysis of Novel Benzimidazolium and Benzotriazolium Compounds as Potent Anti Tubercular Agents
Tsuji Biological and Synthetic Studies of Mitochondrial Respiratory Chain Inhibitors
Debono et al. Uncategorized Comments Off on ANIDULAFUNGIN
Katzka Synthesis of tetramic acids and investigation of their biological properties
WO2014170403A1 (en) Kinase inhibitors
JP2012020978A (ja) 近赤外生物発光基質

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20161102