CA2055590A1 - Chemiluminescent double-triggered 1,2-dioxetanes - Google Patents

Chemiluminescent double-triggered 1,2-dioxetanes

Info

Publication number
CA2055590A1
CA2055590A1 CA2055590A CA2055590A CA2055590A1 CA 2055590 A1 CA2055590 A1 CA 2055590A1 CA 2055590 A CA2055590 A CA 2055590A CA 2055590 A CA2055590 A CA 2055590A CA 2055590 A1 CA2055590 A1 CA 2055590A1
Authority
CA
Canada
Prior art keywords
dioxetane
dioxetanes
chemiluminescent
triggered
double
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.)
Granted
Application number
CA2055590A
Other languages
French (fr)
Other versions
CA2055590C (en
Inventor
Michael S. Urdea
Brian D. Warner
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.)
Novartis Vaccines and Diagnostics Inc
Original Assignee
Michael S. Urdea
Brian D. Warner
Chiron Corporation
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 Michael S. Urdea, Brian D. Warner, Chiron Corporation filed Critical Michael S. Urdea
Publication of CA2055590A1 publication Critical patent/CA2055590A1/en
Application granted granted Critical
Publication of CA2055590C publication Critical patent/CA2055590C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06—Pyrimidine radicals
    • C07H19/10—Pyrimidine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D321/00—Heterocyclic compounds containing rings having two oxygen atoms as the only ring hetero atoms, not provided for by groups C07D317/00 - C07D319/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/655—Heterocyclic 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
    • C07F9/6551—Heterocyclic 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
    • C07F9/65512—Heterocyclic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6558—Heterocyclic 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
    • C07F9/65586—Heterocyclic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
    • C07F9/6574—Esters of oxyacids of phosphorus
    • C07F9/65744—Esters of oxyacids of phosphorus condensed with carbocyclic or heterocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • 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
    • G01N33/58—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances
    • G01N33/581—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances with enzyme label (including co-enzymes, co-factors, enzyme inhibitors or substrates)
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • 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
    • G01N33/58—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances
    • G01N33/582—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances with fluorescent label
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Hematology (AREA)
  • Immunology (AREA)
  • Biomedical Technology (AREA)
  • Urology & Nephrology (AREA)
  • Biotechnology (AREA)
  • Medicinal Chemistry (AREA)
  • Microbiology (AREA)
  • Cell Biology (AREA)
  • Food Science & Technology (AREA)
  • Genetics & Genomics (AREA)
  • Physics & Mathematics (AREA)
  • Analytical Chemistry (AREA)
  • General Physics & Mathematics (AREA)
  • Pathology (AREA)
  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
  • Luminescent Compositions (AREA)
  • Saccharide Compounds (AREA)

Abstract

A stable 1,2-dioxetane of the formula (I), where R1, R2 and R3 are passive organic groups that allow the dioxetane to decompose and produce light when Z and Y are removed, with the proviso that R1 and R2 may be joined to form a cyclic moiety, Z is a first protecting group that can be removed by a first deprotecting process, Y is a second protecting group that can be removed by a second deprotecting process, and X is an organic group which upon removal of Z and Y renders the dioxetane susceptible to said decomposition, with the proviso that X may be joined to R3 to form a cyclic moiety. These di-oxetanes are useful for generating chemiluminescent output in immunoassays and nucleic acid hybridization assays.
CA002055590A 1989-05-31 1990-05-25 Chemiluminescent double-triggered 1,2-dioxetanes Expired - Fee Related CA2055590C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US359,485 1989-05-31
US07/359,485 US5132204A (en) 1989-05-31 1989-05-31 Chemiluminescent double-triggered 1, 2-dioxetanes

Publications (2)

Publication Number Publication Date
CA2055590A1 true CA2055590A1 (en) 1990-12-01
CA2055590C CA2055590C (en) 1997-01-21

Family

ID=23414006

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002055590A Expired - Fee Related CA2055590C (en) 1989-05-31 1990-05-25 Chemiluminescent double-triggered 1,2-dioxetanes

Country Status (6)

Country Link
US (1) US5132204A (en)
EP (1) EP0401001A3 (en)
JP (1) JPH04507404A (en)
CA (1) CA2055590C (en)
PT (1) PT94226B (en)
WO (1) WO1990015040A1 (en)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5582980A (en) * 1989-07-17 1996-12-10 Tropix, Inc. Chemiluminescent 1,2-dioxetanes
US5340716A (en) * 1991-06-20 1994-08-23 Snytex (U.S.A.) Inc. Assay method utilizing photoactivated chemiluminescent label
ES2113547T3 (en) * 1992-07-31 1998-05-01 Behringwerke Ag PHOTOACTIVABLE CHEMIOLUMINISCENT MATRICES.
US5523212A (en) * 1993-05-17 1996-06-04 Lumigen, Inc. Aryl N-alkylacridanthiocarboxylate derivatives useful for chemiluminescent detection
US5491072A (en) * 1993-05-17 1996-02-13 Lumigen, Inc. N-alkylacridan carboxyl derivatives useful for chemiluminescent detection
US5773628A (en) * 1994-11-14 1998-06-30 Tropix, Inc. 1,2-dioxetane compounds with haloalkoxy groups, methods preparation and use
US5578253A (en) * 1994-11-23 1996-11-26 Lumigen, Inc. Chemiluminescent dialkyl-substituted 1,2-dioxetane compounds, methods of synthesis and use
AU6683896A (en) * 1995-07-31 1997-02-26 Charm Sciences, Inc. Chemiluminescent method of monitoring products after heat treatment
US5783381A (en) * 1995-10-19 1998-07-21 Tropix, Inc. Chemiluminescent 1,2-dioxetanes
AU716233B2 (en) * 1996-01-16 2000-02-24 Lumigen, Inc. Compounds, compositions and methods for generating chemiluminescence with phosphatase enzymes
GB9622524D0 (en) 1996-10-29 1997-01-08 London Biotechnology Ltd Enzyme labels for assays
US5800999A (en) * 1996-12-16 1998-09-01 Tropix, Inc. Dioxetane-precursor-labeled probes and detection assays employing the same
US6783948B1 (en) 1999-07-30 2004-08-31 Bayer Corporation Chemiluminescent acridinium compounds and analogues thereof as substrates of hydrolytic enzymes
US6982336B2 (en) 2001-03-08 2006-01-03 Tosoh Corporation 1,2-dioxetane derivatives, luminescent reagents, luminescence methods and measuring methods
US9261460B2 (en) 2002-03-12 2016-02-16 Enzo Life Sciences, Inc. Real-time nucleic acid detection processes and compositions
US7166478B2 (en) * 2002-03-12 2007-01-23 Enzo Life Sciences, Inc., C/O Enzo Biochem, Inc. Labeling reagents and labeled targets, target labeling processes and other processes for using same in nucleic acid determinations and analyses
US9353405B2 (en) 2002-03-12 2016-05-31 Enzo Life Sciences, Inc. Optimized real time nucleic acid detection processes
US7390670B2 (en) 2003-02-20 2008-06-24 Lumigen, Inc. Signalling compounds and methods for detecting hydrogen peroxide
FR2886292B1 (en) 2005-05-27 2009-10-16 Quidd Soc Par Actions Simplifiee BIOMARKER WITH LUMINESCENT TRANSMISSION
JP2013533354A (en) * 2010-07-08 2013-08-22 ライフ テクノロジーズ コーポレーション In situ chemiluminescent substrate and assay method

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3720622A (en) * 1970-01-02 1973-03-13 American Cyanamid Co Generation of light from the decomposition of dioxetaneones in the presence of a fluorescer
US5707559A (en) * 1986-07-17 1998-01-13 Tropix, Inc. Chemiluminescent 1,2-dioxetane compounds
US4959182A (en) * 1986-07-17 1990-09-25 Board Of Governors Of Wayne State University Method and compositions providing enhanced chemiluminescence from 1,2-dioxetanes
EP0275260B1 (en) * 1986-07-24 1993-11-18 Tropix, Inc. Method of detecting a substance using enzymatically-induced decomposition of dioxetanes
US4931223A (en) * 1986-07-24 1990-06-05 Tropix, Inc. Methods of using chemiluminescent 1,2-dioxetanes
EP0348494B1 (en) * 1987-12-31 1994-08-10 Tropix, Inc. Dioxetanes for use in assays

Also Published As

Publication number Publication date
EP0401001A3 (en) 1992-09-02
PT94226A (en) 1991-02-08
WO1990015040A1 (en) 1990-12-13
JPH04507404A (en) 1992-12-24
PT94226B (en) 1997-01-31
EP0401001A2 (en) 1990-12-05
CA2055590C (en) 1997-01-21
US5132204A (en) 1992-07-21

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