WO2021086977A1 - Rapid, high-intensity chemiluminescent dioxetanes - Google Patents

Rapid, high-intensity chemiluminescent dioxetanes Download PDF

Info

Publication number
WO2021086977A1
WO2021086977A1 PCT/US2020/057755 US2020057755W WO2021086977A1 WO 2021086977 A1 WO2021086977 A1 WO 2021086977A1 US 2020057755 W US2020057755 W US 2020057755W WO 2021086977 A1 WO2021086977 A1 WO 2021086977A1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
alkyl
group
aryl
heteroaryl
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.)
Ceased
Application number
PCT/US2020/057755
Other languages
English (en)
French (fr)
Inventor
Khaledur Rashid
Guoping Wang
Barry A. Schoenfelner
Wenhua Xie
Renuka De Silva
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.)
Beckman Coulter Inc
Original Assignee
Beckman Coulter Inc
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 Beckman Coulter Inc filed Critical Beckman Coulter Inc
Priority to CN202511472993.7A priority Critical patent/CN121293248A/zh
Priority to CN202080089331.0A priority patent/CN114867716B/zh
Priority to US17/772,269 priority patent/US20220390459A1/en
Priority to JP2022524938A priority patent/JP7804573B2/ja
Priority to EP20811822.4A priority patent/EP4051670A1/en
Publication of WO2021086977A1 publication Critical patent/WO2021086977A1/en
Anticipated expiration legal-status Critical
Priority to JP2025125905A priority patent/JP2025176001A/ja
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • G01N33/58Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances
    • G01N33/582Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances with fluorescent label
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D321/00Heterocyclic compounds containing rings having two oxygen atoms as the only ring hetero atoms, not provided for by groups C07D317/00 - C07D319/00
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D407/00Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/10Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D409/00Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/10Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/547Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/655Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
    • C07F9/6551Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a four-membered ring
    • C07F9/65512Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a four-membered ring condensed with carbocyclic rings or carbocyclic ring systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/547Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6558Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
    • C07F9/65586Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system at least one of the hetero rings does not contain nitrogen as ring hetero atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/26Acyclic or carbocyclic radicals, substituted by hetero rings
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00Luminescent materials, e.g. electroluminescent or chemiluminescent
    • C09K11/06Luminescent materials, e.g. electroluminescent or chemiluminescent containing organic luminescent materials
    • C09K11/07Luminescent materials, e.g. electroluminescent or chemiluminescent containing organic luminescent materials having chemically-interreactive components, e.g. reactive chemiluminescent compositions
    • GPHYSICS
    • G01MEASURING; TESTING
    • G01NINVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N21/00Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • G01N21/75Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated
    • G01N21/76Chemiluminescence; Bioluminescence
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1018Heterocyclic compounds

Definitions

  • Q is a TT-conjugated electron-donating group.
  • Various compounds described herein can advantageously provide a rapid, high-intensity luminescent signal in non-aqueous media, aqueous media, or both. It is a significant advantage that assays involving such compounds can be performed faster than those with compounds lacking the features of the presently described compounds. Moreover, the compounds of the present disclosure provide increased intensity of luminescence, including in aqueous media. It is another advantage of the present compounds that aqueous compositions thereof can be free of surfactant-based luminescence enhancers.. Due to such advantageous properties, various embodiments of the present disclosure can provide a method or kit that can detect an analyte in an aqueous or non-aqueous sample in under 3 minutes, under 1 minute, under 30 seconds, or in about 15 seconds or less.
  • the present disclosure provides a composition comprising one or more of the compounds described herein, an olefin precursor thereof, or salt thereof.
  • An olefin precursor provides any compound described herein (e.g., a compound of Formula I, II, lla, III, Ilia, lllb, and IV-XV) upon treatment with an analyte, an oxidizing agent, an alkaline phosphatase, or photooxidation conditions.
  • the compounds and compositions described herein can be triggered directly by an analyte so as to produce a signal identifying the presence of the analyte and probe or can be triggered in a two step-process, one step which involves contacting the analyte and another step which involves raising the pH.
  • the compounds of the present disclosure can be configured as probes to detect variety of different analytes by modifying group X or G.
  • Light intensity is the product of the catalytic turnover of substrate in step (i) and the lifetime of the resulting light-producing compound P* in step (ii).
  • Step (iii) is extremely short in comparison to the other steps and generally has no meaningful effect on reaction kinetics.
  • Chemiluminescence intensity/time profile comprises a period of initial rising emission intensity and a subsequent period of steady-state intensity. A slow first order reaction of S' ⁇ P* corresponds to an extended rise time as it takes longer for the steady state concentration of S' to be reached.
  • an aromatic ring substituted with a ⁇ -conjugated propenyl group would be understood to be a propen-1 -yl or a propen-2-yl group rather than a propen-3-yl group.
  • mono-valent (C 2 -C 20 i-alkenyl groups include those with from 1 to 8 carbon atoms such as vinyl, propenyl, propen-1 -yl, propen-2-yl, butenyl, buten-1-yl, buten-2-yl, sec- buten-1-yl, seobuten-3-yl, pentenyl, hexenyl, heptenyl and octenyl groups.
  • R 4 , R 5 , R 6 , and R 7 provide a net electron donating effect if the pKa of a phenolic group at X is greater than that of a compound where R 4 , R 5 , R 6 , and R 7 are H.
  • solvate means a compound, or a salt thereof, that further includes a stoichiometric or non-stoichiometric amount of solvent bound by non- covalent intermolecular forces. Where the solvent is water, the solvate is a hydrate.
  • Values expressed in a range format should be interpreted in a flexible manner to include not only the numerical values explicitly recited as the limits of the range, but also to include all the individual numerical values or sub-ranges encompassed within that range as if each numerical value and sub-range were explicitly recited.
  • Example 16 A dioxetane compound was prepared according to the following structure:

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Immunology (AREA)
  • Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Hematology (AREA)
  • Pathology (AREA)
  • General Physics & Mathematics (AREA)
  • Analytical Chemistry (AREA)
  • Biotechnology (AREA)
  • Urology & Nephrology (AREA)
  • Biomedical Technology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • Cell Biology (AREA)
  • Plasma & Fusion (AREA)
  • Microbiology (AREA)
  • Genetics & Genomics (AREA)
  • Food Science & Technology (AREA)
  • Medicinal Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Saccharide Compounds (AREA)
PCT/US2020/057755 2019-10-28 2020-10-28 Rapid, high-intensity chemiluminescent dioxetanes Ceased WO2021086977A1 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
CN202511472993.7A CN121293248A (zh) 2019-10-28 2020-10-28 快速、高强度的化学发光二氧杂环丁烷
CN202080089331.0A CN114867716B (zh) 2019-10-28 2020-10-28 快速、高强度的化学发光二氧杂环丁烷
US17/772,269 US20220390459A1 (en) 2019-10-28 2020-10-28 Rapid, high-intensity chemiluminescent dioxetanes
JP2022524938A JP7804573B2 (ja) 2019-10-28 2020-10-28 急速、高強度化学発光ジオキサン
EP20811822.4A EP4051670A1 (en) 2019-10-28 2020-10-28 Rapid, high-intensity chemiluminescent dioxetanes
JP2025125905A JP2025176001A (ja) 2019-10-28 2025-07-28 急速、高強度化学発光ジオキサン

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201962926985P 2019-10-28 2019-10-28
US62/926,985 2019-10-28

Publications (1)

Publication Number Publication Date
WO2021086977A1 true WO2021086977A1 (en) 2021-05-06

Family

ID=73544303

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2020/057755 Ceased WO2021086977A1 (en) 2019-10-28 2020-10-28 Rapid, high-intensity chemiluminescent dioxetanes

Country Status (5)

Country Link
US (1) US20220390459A1 (https=)
EP (1) EP4051670A1 (https=)
JP (2) JP7804573B2 (https=)
CN (2) CN114867716B (https=)
WO (1) WO2021086977A1 (https=)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113861160A (zh) * 2021-10-26 2021-12-31 南京工业大学 一种一氧化碳气体检测化学发光探针、制备方法及其应用
EP4219651A1 (en) * 2022-01-28 2023-08-02 Sysmex Corporation Compound or salt thereof, composition, chemiluminescence method, method for measuring chemiluminescence signal, reagent, reagent kit, and method for assaying analyte
WO2024011149A1 (en) 2022-07-05 2024-01-11 Beckman Coulter, Inc. Improved assay compositions and methods
WO2024026467A1 (en) 2022-07-29 2024-02-01 Beckman Coulter, Inc. Chemiluminescent reagents for detection of alkaline phosphatases
WO2024036295A1 (en) 2022-08-12 2024-02-15 Beckman Coulter, Inc. Cross-reference to related applications
WO2025155731A1 (en) * 2024-01-16 2025-07-24 Beckman Coulter, Inc. Alternative substrate pack for automated clinical analyzer and methods of use
WO2025155701A1 (en) * 2024-01-16 2025-07-24 Beckman Coulter, Inc. Automated clinical analyzer with alternative substrate and method of use
WO2025160017A1 (en) * 2024-01-26 2025-07-31 Beckman Coulter, Inc. Assay methods using chemiluminescent dioxetane compounds

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115819416B (zh) * 2022-11-29 2024-06-25 遵义医科大学 一种用于检测和区分的多模态化学发光分子及其应用

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4962192A (en) 1986-07-17 1990-10-09 Board Of Governors Of Wayne State University Chemiluminescent 1,2-dioxetane compounds
US5004565A (en) 1986-07-17 1991-04-02 The Board Of Governors Of Wayne State University Method and compositions providing enhanced chemiluminescence from 1,2-dioxetanes
WO1996015122A1 (en) 1994-11-14 1996-05-23 Tropix, Inc. Novel 1,2-dioxetane compounds with haloalkoxy groups, methods of preparation and use
WO1997000869A1 (en) * 1995-06-20 1997-01-09 Lumigen, Inc. Process for the preparation of 1,2-dioxetane compounds and novel sulfur-substituted 1,2-dioxetane compounds as intermediates
US5603868A (en) * 1992-10-30 1997-02-18 Abbott Laboratories Chemiluminescent electron-rich aryl-substituted 1,2-dioxetanes
US20140154675A1 (en) * 2011-05-03 2014-06-05 Life Technologies Corporation Flash and Glow 1,2-Dioxetanes
WO2017130191A1 (en) * 2016-01-26 2017-08-03 Ramot At Tel-Aviv University Ltd. Chemiluminescent probes for diagnostics and in vivo imaging

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5538847A (en) * 1989-07-17 1996-07-23 Tropix, Inc. Chemiluminescent 1,2-dioxetanes
JPH08245615A (ja) * 1995-03-11 1996-09-24 Masakatsu Matsumoto 1,2−ジオキセタン誘導体
FR2886292B1 (fr) * 2005-05-27 2009-10-16 Quidd Soc Par Actions Simplifiee Biomarqueur a emission luminescente
WO2012006351A1 (en) * 2010-07-08 2012-01-12 Life Technologies Corporation In situ chemiluminescent substrates and assays
US11241507B2 (en) 2017-05-24 2022-02-08 Ramot At Tel-Aviv University Ltd. Near-infrared chemiluminescent probes for in-vivo imaging

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4962192A (en) 1986-07-17 1990-10-09 Board Of Governors Of Wayne State University Chemiluminescent 1,2-dioxetane compounds
US5004565A (en) 1986-07-17 1991-04-02 The Board Of Governors Of Wayne State University Method and compositions providing enhanced chemiluminescence from 1,2-dioxetanes
US5603868A (en) * 1992-10-30 1997-02-18 Abbott Laboratories Chemiluminescent electron-rich aryl-substituted 1,2-dioxetanes
WO1996015122A1 (en) 1994-11-14 1996-05-23 Tropix, Inc. Novel 1,2-dioxetane compounds with haloalkoxy groups, methods of preparation and use
WO1997000869A1 (en) * 1995-06-20 1997-01-09 Lumigen, Inc. Process for the preparation of 1,2-dioxetane compounds and novel sulfur-substituted 1,2-dioxetane compounds as intermediates
US20140154675A1 (en) * 2011-05-03 2014-06-05 Life Technologies Corporation Flash and Glow 1,2-Dioxetanes
WO2017130191A1 (en) * 2016-01-26 2017-08-03 Ramot At Tel-Aviv University Ltd. Chemiluminescent probes for diagnostics and in vivo imaging

Non-Patent Citations (17)

* Cited by examiner, † Cited by third party
Title
"Remington's Pharmaceutical Sciences", 1985, MACK PUBLISHING COMPANY
A.K. CAMPBELL: "Chemiluminescence Principles and Applications in Biology and Medicine", 1988, ELLIS HORWOOD, article "Detection and Quantification of Chemiluminescence", pages: 68 - 126
AN ET AL.: "A Chemiluminescent Probe for HNO Quantification and Real-Time Monitoring in Living Cells", ANGEW. CHEM. INT. ED., vol. 58, no. 5, 26 November 2018 (2018-11-26), pages 1361 - 1365, XP055765232, ISSN: 1433-7851, DOI: 10.1002/anie.201811257 *
AN ET AL.: "Energy transfer chemiluminescence for ratiometric pH imaging", ORG. BIOMOL. CHEM., vol. 16, no. 22, 17 May 2018 (2018-05-17), pages 4176 - 4182, XP055765260, ISSN: 1477-0520, DOI: 10.1039/C8OB00972D *
F. BERTHOLD: "Luminescence Immunoassay and Molecular Applications", 1990, CRC PRESS, article "Instrumentation for Chemiluminescence Immunoassays", pages: 11 - 25
HANANYA ET AL.: "Rapid chemiexcitation of phenoxy-dioxetane luminophores yields ultrasensitive chemiluminescence assays", CHEM. SCI., vol. 10, no. 5, 19 November 2018 (2018-11-19), United Kingdom, pages 1380 - 1385, XP055765244, ISSN: 2041-6520, DOI: 10.1039/C8SC04280B *
HISAMATSU ET AL.: "Effect of the o -Acetamido Group on pH-Dependent Light Emission of a 3-Hydroxyphenyl-Substituted Dioxetane Luminophore", ORG. LETT., vol. 21, no. 5, 15 February 2019 (2019-02-15), US, pages 1258 - 1262, XP055765251, ISSN: 1523-7060, DOI: 10.1021/acs.orglett.8b03913 *
J. MCMURRY: "Organic Chemistry", 2000, BROOKS/COLE, PACIFIC GROVE
J.E. LEFFLERE. GRUNWALD: "Rates and Equilibria of Organic Reactions", 1963, WILEY
J.E. WAMPLER: "Chemi- and Bioluminescence", 1985, MARCEL DEKKER, article "Instrumentation: Seeing the Light and Measuring It", pages: 1 - 44
JERRY MARCHMICHAEL B. SMITH: "March's Advanced Organic Chemistry", 2007, WILEY INTERSCIENCE
MATSUMOTO ET AL.: "Color modulation for intramolecular charge-transfer-induced chemiluminescence of bicyclic dioxetanes bearing a 3-hydroxy-5-naphthylphenyl moiety in the coordination sphere", TETRAHEDRON LETT., vol. 47, no. 47, 20 November 2006 (2006-11-20), pages 8407 - 8411, XP025003346, ISSN: 0040-4039, [retrieved on 20061120], DOI: 10.1016/J.TETLET.2006.09.047 *
MATSUMOTO ET AL.: "SYNTHESIS AND CHEMILUMINESCENCE OF 3-BIPHENYLYL-4,4-DIISOPROPYL-3-METHOXY-1,2-DIOXETANES", HETEROCYCLES, vol. 41, no. 11, 1 November 1995 (1995-11-01), pages 2419 - 2422, XP000943241, ISSN: 0385-5414 *
SCHAAP, A.P.AKHAVAN, H.ROMANO, L.J., CLIN. CHEM., vol. 35, no. 9, 1989, pages 1863
SON ET AL.: "Chemiluminescent Probe for the In Vitro and In Vivo Imaging of Cancers Over-Expressing NQO1", ANGEW. CHEM. INT. ED., vol. 58, no. 6, 18 December 2018 (2018-12-18), pages 1739 - 1743, XP055765240, ISSN: 1433-7851, DOI: 10.1002/anie.201813032 *
T. NIEMAN: "Encyclopedia of Analytical Science", 1995, ACADEMIC PRESS, article "Chemiluminescence: Theory and Instrumentation, Overview", pages: 608 - 613
THEODORA W. GREENEPETER G. M. WUTS: "Protecting Groups in Organic Synthesis", 1999, J. WILEY

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113861160A (zh) * 2021-10-26 2021-12-31 南京工业大学 一种一氧化碳气体检测化学发光探针、制备方法及其应用
EP4219651A1 (en) * 2022-01-28 2023-08-02 Sysmex Corporation Compound or salt thereof, composition, chemiluminescence method, method for measuring chemiluminescence signal, reagent, reagent kit, and method for assaying analyte
US12281092B2 (en) 2022-01-28 2025-04-22 Sysmex Corporation Compound or salt thereof, composition, chemiluminescence method, method for measuring chemiluminescence signal, reagent, reagent kit, and method for assaying analyte
WO2024011149A1 (en) 2022-07-05 2024-01-11 Beckman Coulter, Inc. Improved assay compositions and methods
WO2024026467A1 (en) 2022-07-29 2024-02-01 Beckman Coulter, Inc. Chemiluminescent reagents for detection of alkaline phosphatases
WO2024036295A1 (en) 2022-08-12 2024-02-15 Beckman Coulter, Inc. Cross-reference to related applications
WO2025155731A1 (en) * 2024-01-16 2025-07-24 Beckman Coulter, Inc. Alternative substrate pack for automated clinical analyzer and methods of use
WO2025155701A1 (en) * 2024-01-16 2025-07-24 Beckman Coulter, Inc. Automated clinical analyzer with alternative substrate and method of use
WO2025160017A1 (en) * 2024-01-26 2025-07-31 Beckman Coulter, Inc. Assay methods using chemiluminescent dioxetane compounds

Also Published As

Publication number Publication date
CN114867716B (zh) 2025-11-07
JP7804573B2 (ja) 2026-01-22
US20220390459A1 (en) 2022-12-08
JP2025176001A (ja) 2025-12-03
EP4051670A1 (en) 2022-09-07
JP2022553424A (ja) 2022-12-22
CN114867716A (zh) 2022-08-05
CN121293248A (zh) 2026-01-09

Similar Documents

Publication Publication Date Title
EP4051670A1 (en) Rapid, high-intensity chemiluminescent dioxetanes
KR100718953B1 (ko) 형광성 란타니드 킬레이트에 의한 검체의 분석
Liu et al. A novel N-nitrosation-based ratiometric fluorescent probe for highly selective imaging endogenous nitric oxide in living cells and zebrafish
KR102717614B1 (ko) 진단 및 인비보 영상용 화학발광 프로브
Guo et al. A dual-emission and large Stokes shift fluorescence probe for real-time discrimination of ROS/RNS and imaging in live cells
Hananya et al. Persistent Chemiluminescent Glow of Phenoxy‐dioxetane Luminophore Enables Unique CRET‐Based Detection of Proteases
US8546147B2 (en) Imidazo[1,2-α]pyrazin-3(7H)-one derivatives bearing a new electron-rich structure
DE69526863T2 (de) Neue 1,2-dioxetane mit haloalkoxy-gruppen, verfahren zur herstellung und verwendung
Shen et al. A specific AIE and ESIPT fluorescent probe for peroxynitrite detection and imaging in living cells
Zhang et al. New class of tetradentate β-diketonate-europium complexes that can be covalently bound to proteins for time-gated fluorometric application
US5886238A (en) Alkene precursors for preparing chemiluminescent dialkyl-substituted 1,2-dioxetane compounds
Cheng et al. A highly sensitive and selective hypochlorite fluorescent probe based on oxidation of hydrazine via free radical mechanism
Gu et al. Dioxetane-based chemiluminescent probe for fluoride ion-sensing in aqueous solution and living imaging
US10031142B2 (en) In situ chemiluminescent substrates and assays
AU2001235996B2 (en) Measuring method using long life fluorescence of excitation type
WO2024026467A1 (en) Chemiluminescent reagents for detection of alkaline phosphatases
JP5228190B2 (ja) パーオキシナイトライト蛍光プローブ
Debieu et al. In situ formation of pyronin dyes for fluorescence protease sensing
CN113024523B (zh) 检测成纤维细胞激活蛋白的化学发光探针及其合成方法与应用
CN112469705A (zh) 长波长发射化学发光探针
KR20240127091A (ko) 트립신 또는 트립신 억제제 선택성을 갖는 형광 센서 및 이를 이용한 트립신 또는 트립신 억제제 검출방법
JP4519320B2 (ja) ベンゾチアゾールジオキセタン類
Zhang et al. A facile ratiometric near-infrared fluorescent probe using conjugated 1, 8-naphthalimide and dicyanoisophorone with a vinylene linker for detection and bioimaging of hypochlorite
WO2013093481A1 (en) Fluorescent dyes based on acridine and acridinium derivatives
JPWO2007026808A1 (ja) 新規な蛍光標識化合物

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 20811822

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2022524938

Country of ref document: JP

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

ENP Entry into the national phase

Ref document number: 2020811822

Country of ref document: EP

Effective date: 20220530

WWG Wipo information: grant in national office

Ref document number: 202080089331.0

Country of ref document: CN