AU733086C - Chemiluminescence compositions and methods - Google Patents
Chemiluminescence compositions and methodsInfo
- Publication number
- AU733086C AU733086C AU88975/98A AU8897598A AU733086C AU 733086 C AU733086 C AU 733086C AU 88975/98 A AU88975/98 A AU 88975/98A AU 8897598 A AU8897598 A AU 8897598A AU 733086 C AU733086 C AU 733086C
- Authority
- AU
- Australia
- Prior art keywords
- substituted
- groups
- formula
- unsubstituted
- hydrogen
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 100
- 239000000203 mixture Substances 0.000 title claims abstract description 91
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- 108040007629 peroxidase activity proteins Proteins 0.000 claims abstract description 110
- 238000006243 chemical reaction Methods 0.000 claims abstract description 77
- 102000004190 Enzymes Human genes 0.000 claims abstract description 66
- 108090000790 Enzymes Proteins 0.000 claims abstract description 66
- 238000003556 assay Methods 0.000 claims abstract description 42
- 238000001514 detection method Methods 0.000 claims abstract description 35
- 150000002978 peroxides Chemical class 0.000 claims abstract description 33
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 28
- 230000009870 specific binding Effects 0.000 claims abstract description 21
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 20
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 20
- 239000003623 enhancer Substances 0.000 claims abstract description 18
- 230000000694 effects Effects 0.000 claims abstract description 14
- 102000003992 Peroxidases Human genes 0.000 claims abstract description 13
- 239000002736 nonionic surfactant Substances 0.000 claims abstract description 11
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
- 239000001301 oxygen Substances 0.000 claims abstract description 8
- 230000035945 sensitivity Effects 0.000 claims abstract description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000003093 cationic surfactant Substances 0.000 claims abstract description 5
- 239000007864 aqueous solution Substances 0.000 claims abstract description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 3
- 102000013415 peroxidase activity proteins Human genes 0.000 claims description 108
- -1 phosphoryl groups Chemical group 0.000 claims description 87
- 229940088598 enzyme Drugs 0.000 claims description 65
- 108010001336 Horseradish Peroxidase Proteins 0.000 claims description 60
- 125000003118 aryl group Chemical group 0.000 claims description 59
- 125000000217 alkyl group Chemical group 0.000 claims description 55
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 47
- 239000003153 chemical reaction reagent Substances 0.000 claims description 46
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims description 41
- 239000001257 hydrogen Substances 0.000 claims description 36
- 239000012491 analyte Substances 0.000 claims description 35
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical group OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 claims description 26
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical group C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 claims description 25
- 125000000623 heterocyclic group Chemical group 0.000 claims description 24
- 238000004519 manufacturing process Methods 0.000 claims description 24
- 230000005281 excited state Effects 0.000 claims description 22
- 239000000460 chlorine Substances 0.000 claims description 17
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 125000004429 atom Chemical group 0.000 claims description 16
- 125000002837 carbocyclic group Chemical group 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 229910052783 alkali metal Inorganic materials 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 229910052698 phosphorus Inorganic materials 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 238000012546 transfer Methods 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 229910001413 alkali metal ion Chemical group 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 13
- 238000001262 western blot Methods 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
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- 150000001768 cations Chemical class 0.000 claims description 11
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- 229910052736 halogen Inorganic materials 0.000 claims description 11
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- 108090000623 proteins and genes Proteins 0.000 claims description 11
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- 125000003107 substituted aryl group Chemical group 0.000 claims description 11
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- 125000004104 aryloxy group Chemical group 0.000 claims description 10
- GPTXWRGISTZRIO-UHFFFAOYSA-N chlorquinaldol Chemical compound ClC1=CC(Cl)=C(O)C2=NC(C)=CC=C21 GPTXWRGISTZRIO-UHFFFAOYSA-N 0.000 claims description 10
- 238000003018 immunoassay Methods 0.000 claims description 10
- 108700020962 Peroxidase Proteins 0.000 claims description 9
- JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 claims description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims description 9
- 229910052710 silicon Inorganic materials 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 8
- 102000004316 Oxidoreductases Human genes 0.000 claims description 7
- 108090000854 Oxidoreductases Proteins 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 125000003147 glycosyl group Chemical group 0.000 claims description 7
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims description 6
- 238000002105 Southern blotting Methods 0.000 claims description 6
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 150000002989 phenols Chemical class 0.000 claims description 5
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 claims description 4
- NGSWKAQJJWESNS-UHFFFAOYSA-N 4-coumaric acid Chemical compound OC(=O)C=CC1=CC=C(O)C=C1 NGSWKAQJJWESNS-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 239000000427 antigen Substances 0.000 claims description 4
- 102000036639 antigens Human genes 0.000 claims description 4
- 108091007433 antigens Proteins 0.000 claims description 4
- 150000004982 aromatic amines Chemical class 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 108020004707 nucleic acids Proteins 0.000 claims description 4
- 102000039446 nucleic acids Human genes 0.000 claims description 4
- 150000007523 nucleic acids Chemical class 0.000 claims description 4
- 125000004437 phosphorous atom Chemical group 0.000 claims description 4
- VSMDINRNYYEDRN-UHFFFAOYSA-N 4-iodophenol Chemical compound OC1=CC=C(I)C=C1 VSMDINRNYYEDRN-UHFFFAOYSA-N 0.000 claims description 3
- 238000000636 Northern blotting Methods 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 3
- 229960005489 paracetamol Drugs 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000001725 pyrenyl group Chemical group 0.000 claims description 3
- HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 claims description 2
- GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 claims description 2
- YLDFTMJPQJXGSS-UHFFFAOYSA-N 6-bromo-2-naphthol Chemical compound C1=C(Br)C=CC2=CC(O)=CC=C21 YLDFTMJPQJXGSS-UHFFFAOYSA-N 0.000 claims description 2
- 108010073997 Bromide peroxidase Proteins 0.000 claims description 2
- 244000068988 Glycine max Species 0.000 claims description 2
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- 150000001298 alcohols Chemical class 0.000 claims description 2
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- 229940057428 lactoperoxidase Drugs 0.000 claims description 2
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- WUYMUVBIVVABRN-UHFFFAOYSA-N 1-[[4-[4-amino-5-(3-methoxyphenyl)pyrrolo[2,3-d]pyrimidin-7-yl]phenyl]methyl]piperidin-4-ol Chemical compound COC1=CC=CC(C=2C3=C(N)N=CN=C3N(C=3C=CC(CN4CCC(O)CC4)=CC=3)C=2)=C1 WUYMUVBIVVABRN-UHFFFAOYSA-N 0.000 claims 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- DIBXSCRTXGVRFD-UHFFFAOYSA-N 4-(1H-imidazol-2-yl)phenol Chemical compound C1=CC(O)=CC=C1C1=NC=CN1 DIBXSCRTXGVRFD-UHFFFAOYSA-N 0.000 claims 1
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 66
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- 239000000243 solution Substances 0.000 description 40
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 30
- 238000005481 NMR spectroscopy Methods 0.000 description 28
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 24
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 18
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 15
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- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
- C09K11/07—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials having chemically interreactive components, e.g. reactive chemiluminescent compositions
-
- 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
- C12Q1/26—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving oxidoreductase
- C12Q1/28—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving oxidoreductase involving peroxidase
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/968—High energy substrates, e.g. fluorescent, chemiluminescent, radioactive
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
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- Immunology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Materials Engineering (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Luminescent Compositions (AREA)
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| PCT/US1998/015813 WO1999014358A1 (en) | 1997-09-12 | 1998-08-12 | Chemiluminescence compositions and methods |
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| WO1997026245A1 (en) * | 1996-01-16 | 1997-07-24 | Lumigen, Inc. | Compounds, compositions and methods for generating chemiluminescence with phosphatase enzymes |
| US6126870A (en) * | 1997-09-12 | 2000-10-03 | Lumigen, Inc. | Chemiluminescent labeling compounds |
| US6017769A (en) * | 1998-06-17 | 2000-01-25 | Lumigen, Inc. | Non-enzymatic methods of generating chemiluminescence from acridan alkenes |
| US7186568B1 (en) * | 2000-06-26 | 2007-03-06 | Lumigen Inc. | Electrochemiluminescence from acridan compounds |
| EP1322670B1 (en) * | 2000-06-26 | 2005-12-21 | Lumigen, Inc. | Electrochemiluminescence from acridan compounds |
| US6872828B2 (en) * | 2001-12-20 | 2005-03-29 | Lumigen, Inc. | Compounds for generating chemiluminescence with a peroxidase |
| EP1456176B1 (en) * | 2001-12-20 | 2009-03-18 | Lumigen, Inc. | Improved compounds for generating chemiluminescence with a peroxidase |
| US7560556B2 (en) * | 2001-12-20 | 2009-07-14 | Lumigen, Inc. | Assay methods using chemiluminescent detection of peroxidase |
| US6897036B2 (en) * | 2002-06-06 | 2005-05-24 | Lumigen, Inc. | Fluorescent detection of peroxidase enzymes |
| US7390670B2 (en) | 2003-02-20 | 2008-06-24 | Lumigen, Inc. | Signalling compounds and methods for detecting hydrogen peroxide |
| US7682839B2 (en) * | 2005-03-14 | 2010-03-23 | Lumigen, Inc. | Methods using novel chemiluminescent labels |
| US20060205094A1 (en) * | 2005-03-14 | 2006-09-14 | Lumigen, Inc. | Methods using novel chemiluminescent labels |
| US7879575B2 (en) * | 2005-04-27 | 2011-02-01 | The Trustees Of The University Of Pennsylvania | Nanostructures that provide a modified nanoenvironment for the enhancement of luminescence |
| WO2006116686A2 (en) * | 2005-04-27 | 2006-11-02 | The Trustees Of The University Of Pennsylvania | Nanostructure enhanced luminescent devices |
| WO2006116687A2 (en) * | 2005-04-27 | 2006-11-02 | The Trustees Of The University Of Pennsylvania | Nanoassays |
| US7566573B2 (en) * | 2005-12-19 | 2009-07-28 | Idexx Laboratories, Inc. | Dual standard curve immunoassay |
| US7732153B2 (en) | 2006-05-09 | 2010-06-08 | Beckman Coulter, Inc. | Nonseparation assay methods |
| US7799534B2 (en) * | 2006-05-09 | 2010-09-21 | Beckman Coulter, Inc. | Nonseparation assay methods |
| US7674629B2 (en) * | 2007-03-15 | 2010-03-09 | Saint Louis University | Method for improving chemiluminescent signal |
| WO2009062027A1 (en) * | 2007-11-07 | 2009-05-14 | Beckman Coulter, Inc. | Nonseparation assay methods using peroxide generating enzymes |
| CN101178402B (zh) * | 2007-12-06 | 2011-08-24 | 武汉赛欣生物技术有限公司 | 聚合酶标记抗体的制备方法 |
| US20090162876A1 (en) * | 2007-12-20 | 2009-06-25 | Abbott Laboratories | Myeloperoxidase assays |
| US8652442B2 (en) | 2008-11-03 | 2014-02-18 | Washington University | Bioluminescence imaging of myeloperoxidase activity in vivo, methods, compositions and apparatuses therefor |
| CN102333885A (zh) | 2009-02-27 | 2012-01-25 | 贝克曼考尔特公司 | 使用选择性信号抑制剂的非分离式测定 |
| US9029092B2 (en) | 2009-02-27 | 2015-05-12 | Beckman Coulter, Inc. | Solution phase homogeneous assays |
| US20110097723A1 (en) * | 2009-09-19 | 2011-04-28 | Qun Liu | Methods and reagents for analyte detection |
| JP6553020B2 (ja) | 2013-03-15 | 2019-07-31 | ジーピービー デット ホールディングス トゥー エルエルシー | アレルギー及び自己免疫疾患に関する診断分析を行うための自動化された免疫分析計システム |
| US9383336B2 (en) | 2014-04-04 | 2016-07-05 | General Electric Company | System and method for flat panel detector gel and blot imaging |
| CN104761584A (zh) * | 2015-02-27 | 2015-07-08 | 北京利德曼生化股份有限公司 | 吖啶酯衍生物及其合成方法和应用 |
| EP3350577B1 (en) * | 2015-09-16 | 2022-02-16 | Global Life Sciences Solutions Germany Gmbh | System and method for flat panel detector gel and blot imaging |
| WO2020012391A1 (en) | 2018-07-13 | 2020-01-16 | 3M Innovative Properties Company | Assay |
| CN112400113B (zh) | 2018-07-13 | 2022-04-15 | 3M创新有限公司 | 特异性结合化学发光测定法 |
| CN113295678B (zh) * | 2021-05-14 | 2022-11-08 | 济南迪曼生物科技有限公司 | 一种电化学发光清洗液 |
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| DE68911633T2 (de) * | 1988-09-30 | 1994-04-07 | Fujirebio Kk | Verfahren zur Bestimmung von Peroxidase-Aktivität unter Verwendung von Chemilumineszenz. |
| EP0422252B1 (en) * | 1989-04-28 | 1995-07-26 | Toray Industries, Inc. | Method for detecting a substance using chemiluminescence |
| DD296503A5 (de) * | 1989-07-13 | 1991-12-05 | �K@�K@������������@�K@�Kk�� | Chemitumineszente zusammensetzungen, chemilumineszenz-verfahren und ihre anwendung in analytischen tests |
| US5324835A (en) * | 1990-03-30 | 1994-06-28 | Biosensor Laboratories Co., Ltd. | Pyridazinoquinoxalinones for use as chemiluminescent agents |
| US5629168A (en) * | 1992-02-10 | 1997-05-13 | British Technology Group Limited | Chemiluminescent enhancers |
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-
1997
- 1997-09-12 US US08/928,793 patent/US5922558A/en not_active Expired - Lifetime
-
1998
- 1998-08-12 WO PCT/US1998/015813 patent/WO1999014358A1/en not_active Ceased
- 1998-08-12 AT AT98940778T patent/ATE280241T1/de not_active IP Right Cessation
- 1998-08-12 CA CA2300096A patent/CA2300096C/en not_active Expired - Lifetime
- 1998-08-12 ES ES98940778T patent/ES2230710T3/es not_active Expired - Lifetime
- 1998-08-12 DE DE69827152T patent/DE69827152T2/de not_active Expired - Lifetime
- 1998-08-12 JP JP2000511896A patent/JP4790905B2/ja not_active Expired - Lifetime
- 1998-08-12 EP EP98940778A patent/EP1019525B1/en not_active Expired - Lifetime
- 1998-08-12 AU AU88975/98A patent/AU733086C/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES2230710T3 (es) | 2005-05-01 |
| CA2300096A1 (en) | 1999-03-25 |
| EP1019525B1 (en) | 2004-10-20 |
| ATE280241T1 (de) | 2004-11-15 |
| EP1019525A4 (en) | 2003-01-02 |
| WO1999014358A1 (en) | 1999-03-25 |
| AU8897598A (en) | 1999-04-05 |
| DE69827152T2 (de) | 2006-03-09 |
| JP2001516589A (ja) | 2001-10-02 |
| AU733086B2 (en) | 2001-05-03 |
| CA2300096C (en) | 2010-02-09 |
| DE69827152D1 (de) | 2004-11-25 |
| EP1019525A1 (en) | 2000-07-19 |
| US5922558A (en) | 1999-07-13 |
| JP4790905B2 (ja) | 2011-10-12 |
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