WO2001055446A1 - Novel stabilized formulations for chemiluminescent assays - Google Patents

Novel stabilized formulations for chemiluminescent assays Download PDF

Info

Publication number
WO2001055446A1
WO2001055446A1 PCT/US2001/002779 US0102779W WO0155446A1 WO 2001055446 A1 WO2001055446 A1 WO 2001055446A1 US 0102779 W US0102779 W US 0102779W WO 0155446 A1 WO0155446 A1 WO 0155446A1
Authority
WO
WIPO (PCT)
Prior art keywords
substrate
substituted
acid
probe
group
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/US2001/002779
Other languages
French (fr)
Inventor
Brij Pal Giri
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.)
Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Priority to AU2001234612A priority Critical patent/AU2001234612A1/en
Priority to IL15092401A priority patent/IL150924A0/en
Priority to EP01906739A priority patent/EP1254252A4/en
Priority to CA002398812A priority patent/CA2398812A1/en
Publication of WO2001055446A1 publication Critical patent/WO2001055446A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • C12Q1/66—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving luciferase
    • 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
    • G01N33/52—Use of compounds or compositions for colorimetric, spectrophotometric or fluorometric investigation, e.g. use of reagent paper and including single- and multilayer analytical elements

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Immunology (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Molecular Biology (AREA)
  • Physics & Mathematics (AREA)
  • General Health & Medical Sciences (AREA)
  • Hematology (AREA)
  • Biotechnology (AREA)
  • Microbiology (AREA)
  • Analytical Chemistry (AREA)
  • Biochemistry (AREA)
  • Biomedical Technology (AREA)
  • Biophysics (AREA)
  • Urology & Nephrology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • Genetics & Genomics (AREA)
  • General Physics & Mathematics (AREA)
  • Pathology (AREA)
  • Cell Biology (AREA)
  • Medicinal Chemistry (AREA)
  • Food Science & Technology (AREA)
  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
  • Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)

Abstract

A substrate having an extended shelf life for chemiluminescent detection and assaying is useful with enzyme-based probes as well as for immunoassays, DNA or RNA or protein detection and blotting. The substrate is a mixture of (a) a chemiluminescent compound, (b) an oxidant, (c) a stabilizer and (d) a buffer. The substrate may further include a chemiluminescent enhancer and a solubilizer. That substrate may be in an organic solvent or may be aqueous based. Figures (1A and 1B) shows varying concentrations, in femtograms, of peroxidase enzyme and was plotted against intensity.

Claims

Claims:
1. A stabilized substrate formulation for use in chemiluminescent assays and detection procedures comprising:
(a) at least one chemiluminescent organic compound, (b) at least one oxidizing agent,
(c) at least one stabilizing agent, and
(d) at least one suitable buffer, the formulation having a pH of from about pH 5.5 to about pH 12.0.
2. The substrate formulation of claim 1 wherein: the chemiluminescent compound is selected from the group consisting of but not limited to resorcinol, pyrogallol, phloroglucinol, purpurogallin, aminoaryl cyclic diacylhydrazide or the salts thereof, hydroxyaryl cyclic diacylhydrazide, pyridopyridazine derivatives, 10, 10-dimethyl-9,9- biacridane, 9-benzylidene-10-methylacridane or substituted-9- benzylidene-10-methylacridane, N-methylacridane or substituted N- methylacridane, 9-benzylacridane or substituted-9-benzylacridane, 9- benzyl-N-methylacridane or substituted-9-benzyl-N-methylacridane, N-alkylacridane-9-carboxylic acid and ester or thioester, indole-3- acetic acid and ester or thioester, N-methylindole-3-acetic acid and ester, phenyl or substituted phenyl-2-(6 -hydroxy-2-beπzothiazolyl-Δ2- thiazoline-4-carboxylate, methyl 2-(6 -hydroxy-2 -benzothiazolyl)-Δ2- thiazoline-4-carboxylate, 2-(6 -hydroxy-2 -benzothiazolyl)-Δ2- thiazoline acetic acid or ester, 2-(4 -hydroxyphenyl) thiazole-4- carboxylic acid hydrazide, 2-(6 -hydroxy-2 -benzothiazolyl) thiazole-4- carboxylic acid hydrazide, 9-acridanecarboxylic acid hydrazide or substituted 9-acridanecarboxylic acid hydrazide, N-alkyl-9- acridanecarboxylic acid hydrazide or substitutedN-alkyl-9- acridanecarboxylic acid hydrazide, o-hydroxybenzoic acid hydrazide, o-aminobenzoic acid hydrazide, m-hydroxybenzoic acid hydrazide, 2-
28 hydroxy-3-naphthoic acid hydrazide, 2-amino-3-naphthoic acid hydrazide, 1-hydroxy-2-anthroic acid hydrazide, D-luciferin-O- sulphate, D-luciferin-O-phosphate and luciferins isolated from Pholas dactlus, the firefly Photinus pyralis or Cypridina, and mixtures thereof and further wherein when the compound is an aryl compound, the aryl component is phenyl, substituted phenyl, naphthyl, substituted naphthyl, anthryl or substituted anthryl.
3. The substrate formulation of claim 1 wherein: the stabilizing agent is selected from the group consisting of cyclodextrins, dextran sulfate, sugars, Tween 20, Tweem 40, Tween 60, Tween 80, Tween 85,
Triton X-100, Triton X-100 (reduced), Triton N-101 , Triton N-101 (reduced), Triton X-1 14, Triton X-114 (reduced), Triton X-405, Triton X-405 (reduced ), Brij 35, lauryl sulfate, domiphen bromide, cetyltrimethyl ammonium bromide, cetyltrimethyl ammonium chloride, cetyldimethylethyi ammonium bromide, Bacitracin, BSA, KLH, HSA,
Trypsin inhibitor, polyethylene glycol, polymeric phosphonium salts, polymeric ammonium salts, DEQUEST 2060S, Coenzyme A, inorganic pyrophosphate, cytidine nucleotides, ethylenediaminetetraacetic acid, diethylenetriaminepentaacetic acid, ethylenebis(oxyethylenenitrilo) tetraacetic acid, and other related macromolecules, surfactants and polymers.
4. The substrate formulation of claim 1 wherein: the oxidizing agent is selected from the group consisting of hydrogen peroxide, urea hydrogen peroxide, sodium carbonate hydrogen peroxide, a perborate salt and mixtures thereof.
5. The substrate formulation of claim 1 which comprises:
(a) from about 0.1 μM to about 200 mM by volume, based on the total volume, of the chemiluminescent compound,
(b) from about 0.5 μM to about 250 mM by volume, based on the total volume, of the oxidizing agent
29 (c) from about 0.01% to about 40% by volume, based on the total volume, of the stabilizing agent, and
(d) from about 0.1 mM to about 10 M by volume, based on the total volume, of the buffer.
6. The substrate formulation of claim 1 which further comprises:
(a) a solubilizing agent, and
(b) a chemiluminescence enhancer.
7. The substrate formulation of claim 6 which further comprises:
(a), from about 0.1% to about 20%, by volume, based on the total volume, of the solubilizing agent, and
(b). from about 0.1 μM to about 200 mM by volume, based on the total volume, of the enhancer.
8. The substrate formulation of claim 7 wherein:
(a) the solubilizing agent is selected from the group consisting of dimethyl sulfoxide, dimethyl formamide, dioxane, tetrahydrofuran, alcohols and mixture thereof,
(b) the enhancer is selected from the group consisting of p- iodophenol, p-bromophenol, p-chlorophenol, 4-bromo-2- chlorophenol, 3,4-dichlorophenol, 4-methylphenol, 4-tert-butylphenol, 3-(4-hydroxyphenyl) propionate, 4-benzylphenol, 4-(2 ,4 -dinitrostyryl) phenol, 2,4-dichlorophenol, p-hydroxycinnamic acid, p-fluorocinnamic acid, p-nitricinnamic acid, p-aminocinnamic acid, m-hydroxycinnamic acid, o-hydroxycinnamic acid, 4-phenoxyphenol, 4-(4 -hydroxyphenoxy) phenol, p-phenylphenol, 2-chloro-4-phenylphenol, 4-(4- hydroxyphenyl) benzophenone, 4-(phenylazo) phenol, 4-(2- carboxyphenylaza) phenol, 1 ,6-dibromonaphtho-2-ol, 1- bromonaphtho-2-ol, 2-naphthol, 6-bromonaphth-2-ol, 6- hydroxybenzothiazole, 2-amino-6-hydroxybenzothiazole, 2,6- dihydroxybenzothiazole, 2-cyano-6-hydroxybenzothiazole, dehydroluciferin, firefly luciferin, phenolindophenol, 2,6- dichlorophenolindophenol, 2,6-dichlorophenol-o-cresol,
30 phenolindoaniline, N-alkylphenoxazine or substituted N- alkylphenoxazine, N-alkylphenothiazine or substituted N- alkylphenothiazine,N-alkylpyrimidylphenoxazine or substituted N- alkylpyrimidylphenoxazine, N-alkylpyridylphenoxazine, 2-hydroxy-9- fluorenone or substituted 2-hydroxy-9-fluorenone, 6- hydroxybenzoxazole or substituted 6-hydroxybenzoxazole, a protected enhancer that can cleave by the enzyme in the formulation of present invention such as the p-phenylphenol phosphate, p- iodophenol phosphate, or having other enzyme cleavable groups, p- phenylene diamine and tetramethyl benzidine and mixtures thereof.
9. The substrate formulation of claim 1 wherein:
(a) the chemiluminescent compound is selected from the group consisting of luminol, isoluminol, acridane, phenyl -10- methylacridane-9-carboxylate, 2,4,6-trichlorophenyl -10- methylacridane-9-carboxylate, pyrogallol, phloroglucinol, resorcinol, and mixtures thereof,
(b) the oxidizing agent is selected from the group consisting from hydrogen peroxide, urea hydrogen peroxide, mixtures thereof, and an in-situ peroxide forming system, and (c) the stabilizing agent is selected from the group consisting of polyethylene branched nonylphenyl ether, polyoxyethylene(10)isooctylphenyl ether, lauryl sulfate, domiphen bromide, CTAB, EDTA and mixtures thereof
10. The substrate formulation of claim 9 which further comprises an enhancer, the enhancer being selected from the group consisting of p-iodophenol, , 3,4-dichlorophenol, p-hydroxycinnamic acid, 1 ,2,4- triazole, 3,3', 5, 5'-tetramethyl- benzidine, phenol, 2-naphthol, 10- methylphenothiazine, cetyltrimethyl ammonium bromide, and mixtures thereof 11. A method for conducting chemiluminescent detection which comprises:
31 (a) providing a probe which reacts with a substrate to form an unstable intermediate which breaks down into a stable end product and detectable light,
(b) contacting the probe with the substrate of claim 1 , and (c) detecting the presence of any generated light by the contact of the probe with the substrate.
12. A method for conducting chemiluminescent detection which comprises:
(a) providing a probe which reacts with a substrate to form an unstable intermediate which breaks down into a stable end product and detectable light,
(b) contacting the probe with the substrate of claim 9, and
(c) detecting the presence of any generated light by the contact of the probe with the substrate.
13. The method of claim 12 wherein, the probe has a triggering substituent selected from the group consisting of: an enzyme, protohemin, hemoglobin and cytochrome C.
14. The method of claim of 13 wherein the trigger of the probe is an enzyme.
15. The method of claim 14 wherein the enzyme of the probe is selected from the group consisting of a horseradish peroxidase, glucose oxidase, cholesterol oxidase, catalase, as well as mixtures thereof.
16. A kit for use in a luminescent assays comprising (a) an organic chemiluminescent compound, (b) an enhancer, (c) an oxidant, (d) a stabilizing agent, (e) a solubilizing agent and (f) a buffer, the substrate having a pH of from about pH 5.5 to about pH 12.0.
17. The substrate of claim 9 wherein the oxidizing agent is a mixture of D-glucose and glucose oxidase which produces hydrogen peroxide in-situ.
32
18. The method of claims 15 wherein: the enzyme is a mixture of horseradish peroxidase and glucose oxidase, the probe detecting the glucose in a body fluid.
19. The method of claims 15 wherein: the enzyme is a mixture of horseradish peroxidase and cholesterol oxidase, the probe detecting the cholesterol in a body fluid.
33
PCT/US2001/002779 2000-01-28 2001-01-26 Novel stabilized formulations for chemiluminescent assays Ceased WO2001055446A1 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
AU2001234612A AU2001234612A1 (en) 2000-01-28 2001-01-26 Novel stabilized formulations for chemiluminescent assays
IL15092401A IL150924A0 (en) 2000-01-28 2001-01-26 Novel stabilized formulations for chemiluminescent assays
EP01906739A EP1254252A4 (en) 2000-01-28 2001-01-26 STABILIZED FORMULAS FOR CHEMILUMINESCENT ASSAYS
CA002398812A CA2398812A1 (en) 2000-01-28 2001-01-26 Novel stabilized formulations for chemiluminescent assays

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US17862600P 2000-01-28 2000-01-28
US60/178,626 2000-01-28

Publications (1)

Publication Number Publication Date
WO2001055446A1 true WO2001055446A1 (en) 2001-08-02

Family

ID=22653265

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2001/002779 Ceased WO2001055446A1 (en) 2000-01-28 2001-01-26 Novel stabilized formulations for chemiluminescent assays

Country Status (6)

Country Link
US (1) US6602679B2 (en)
EP (1) EP1254252A4 (en)
AU (1) AU2001234612A1 (en)
CA (1) CA2398812A1 (en)
IL (1) IL150924A0 (en)
WO (1) WO2001055446A1 (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008049160A1 (en) * 2006-10-24 2008-05-02 Gene Stream Pty Ltd Luciferase signal enhancng compositions
WO2016149127A1 (en) * 2015-03-13 2016-09-22 Li-Cor, Inc. Fluorogenic and chromogenic substrate
JP2019509981A (en) * 2016-01-26 2019-04-11 ラモット・アット・テル・アビブ・ユニバーシテイ・リミテッドＲａｍｏｔ Ａｔ Ｔｅｌ Ａｖｉｖ Ｕｎｉｖｅｒｓｉｔｙ Ｌｔｄ． Chemiluminescent probe for diagnostic and in vivo imaging
IT202000001327A1 (en) * 2020-01-23 2021-07-23 Cyanagen S R L CHEMILUMINESCENT SUBSTRATES FOR PEROXIDASE WITH A LONG SHELF LIFE
US11236325B2 (en) 2014-02-10 2022-02-01 Zymo Research Corporation Methods for nucleic acid capture

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2003239890A1 (en) * 2002-05-23 2003-12-12 Brij Pal Giri POLYMERIC AMMONIUM AND OR PHOSPHONIUM SALTS HAVING ADDED Pi-ELECTRONS AND HIGHER MOLECULAR WEIGHT AS ENHANCERS FOR CHEMILUMINESCENT SYSTEMS
US20040259182A1 (en) * 2003-06-17 2004-12-23 Brooks Edwards Arrays for chemiluminescent assays, methods of making the arrays and methods of detecting chemiluminescent emissions on solid supports
US20050026151A1 (en) * 2003-07-17 2005-02-03 Voyta John C. Simultaneous generation of multiple chemiluminescent signals on solid supports
US20050019778A1 (en) * 2003-07-17 2005-01-27 Voyta John C. Sequential generation of multiple chemiluminescent signals on solid supports
EP1735621A4 (en) * 2004-04-14 2012-12-12 Brij P Giri New ultra-sensitive chemiluminescent substrates for enzymes and their conjugates
WO2006076034A2 (en) * 2004-05-21 2006-07-20 Bhanu, Kalra Stabilized two component system for chemilumiescent assay in immunodiagnostics
US7674629B2 (en) * 2007-03-15 2010-03-09 Saint Louis University Method for improving chemiluminescent signal
US8241915B2 (en) * 2009-01-14 2012-08-14 Abbott Laboratories Methods and kits for detecting hemoglobin in test samples
US20110097723A1 (en) * 2009-09-19 2011-04-28 Qun Liu Methods and reagents for analyte detection
GB201021509D0 (en) * 2010-12-20 2011-02-02 Reactivlab Ltd Assay method
DE102011115480A1 (en) * 2011-10-06 2013-04-11 Biostep Gmbh Substrate useful for chemiluminescence detection using enhancers or enhanced chemiluminescence reactions on carriers, comprises luminophore luminol, where e.g. enhancer concentration is optimized with respect to luminol concentration
WO2014149268A1 (en) 2013-03-19 2014-09-25 Life Technologies Corporation Thermal cycler cover
CN103604918A (en) * 2013-11-28 2014-02-26 中国科学院广州生物医药与健康研究院 Luminescent substrate, use of luminescent substrate and detection kit containing luminescent substrate
EP3420341B1 (en) * 2016-02-24 2020-11-18 Bio-Rad Laboratories, Inc. Methods and compositions for fluorescence detection
WO2018012607A1 (en) * 2016-07-13 2018-01-18 キッコーマン株式会社 Reaction accelerator
US10722882B2 (en) 2016-08-03 2020-07-28 Pierce Biotechnology, Inc. Chemiluminescent and fluorescent substrate pads and uses thereof
CN111579765B (en) * 2019-02-19 2023-05-23 北京北方生物技术研究所有限公司 Excitation liquid system for improving luminous signal-to-noise ratio of acridinium ester
CN115932284B (en) * 2023-03-10 2023-07-21 江苏奥雅生物科技有限公司 Method for coupling acridinium ester with immune protein and application thereof
CN120865895B (en) * 2025-07-25 2026-03-31 禾旭(郑州)生物技术有限公司 A single-component acridine ester luminescent substrate solution and its preparation method

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0087959A1 (en) 1982-03-03 1983-09-07 National Research Development Corporation Enhanced luminescent and luminometric assay
EP0116454A2 (en) 1983-02-11 1984-08-22 National Research Development Corporation Enhanced luminescent or luminometric assay
US5171668A (en) 1988-09-30 1992-12-15 Fujirebio Inc. Method of the chemiluminescence assay of the activity of peroxidase
US5206149A (en) 1989-04-28 1993-04-27 Toray Industries, Inc. Method of high sensitivity luminescence analysis
US5552298A (en) 1992-10-23 1996-09-03 Lumigen, Inc. Enzyme-catalyzed chemiluminescence from hydroxyaryl cyclic diacylhydrazide compounds
US5593845A (en) 1993-05-17 1997-01-14 Lumigen, Inc. Aryl N-alkylacridancarboxylate derivatives useful for chemiluminescent detection
US5670644A (en) 1993-05-17 1997-09-23 Lumigen, Inc. Acridan compounds
WO1997039142A1 (en) 1996-04-15 1997-10-23 Pierce Chemical Company Assay of peroxidase activity
US5707550A (en) 1993-04-06 1998-01-13 Dow Corning Corporation Foam boosting of hair shampoo compositions
US5723295A (en) 1993-05-17 1998-03-03 Lumigen, Inc. Methods, acridan compounds and kits for producing light

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4950588A (en) * 1985-07-10 1990-08-21 Molecular Diagnostics, Inc. Prolonged enhanced chemiluminescence
JP2528457B2 (en) * 1987-03-09 1996-08-28 サントリー株式会社 Hydrogen peroxide determination method
US5547836A (en) * 1990-08-30 1996-08-20 Tropix, Inc. Enhancement of chemiluminescent assays
US5491072A (en) * 1993-05-17 1996-02-13 Lumigen, Inc. N-alkylacridan carboxyl derivatives useful for chemiluminescent detection
US5705357A (en) * 1994-08-29 1998-01-06 Johnson & Johnson Clinical Diagnostics, Inc. Chemiluminescent reagent and assay using a substituted acetanilide for light generation

Patent Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0087959A1 (en) 1982-03-03 1983-09-07 National Research Development Corporation Enhanced luminescent and luminometric assay
EP0116454A2 (en) 1983-02-11 1984-08-22 National Research Development Corporation Enhanced luminescent or luminometric assay
US4598044A (en) 1983-02-11 1986-07-01 National Research Development Corporation Enhanced luminescent or luminometric assay
US5171668A (en) 1988-09-30 1992-12-15 Fujirebio Inc. Method of the chemiluminescence assay of the activity of peroxidase
US5206149A (en) 1989-04-28 1993-04-27 Toray Industries, Inc. Method of high sensitivity luminescence analysis
US5552298A (en) 1992-10-23 1996-09-03 Lumigen, Inc. Enzyme-catalyzed chemiluminescence from hydroxyaryl cyclic diacylhydrazide compounds
US5601977A (en) 1992-10-23 1997-02-11 Lumigen, Inc. Enzyme-catalyzed chemiluminescent detection of proteins and nucleic acids using hydroxyaryl cyclic diacylhydrazide compounds
US5707550A (en) 1993-04-06 1998-01-13 Dow Corning Corporation Foam boosting of hair shampoo compositions
US5593845A (en) 1993-05-17 1997-01-14 Lumigen, Inc. Aryl N-alkylacridancarboxylate derivatives useful for chemiluminescent detection
US5670644A (en) 1993-05-17 1997-09-23 Lumigen, Inc. Acridan compounds
US5723295A (en) 1993-05-17 1998-03-03 Lumigen, Inc. Methods, acridan compounds and kits for producing light
WO1997039142A1 (en) 1996-04-15 1997-10-23 Pierce Chemical Company Assay of peroxidase activity

Non-Patent Citations (31)

* Cited by examiner, † Cited by third party
Title
A.D. PRONOVOST, A. BAUMGARTEN, EXPERIENTIA, vol. 38, 1982, pages 304
A.P. SCHAAP, R.S. HANDLEY, B.P. GIRI, TETRAHEDRON LETT., 1987, pages 935
A.P. SCHAAP, T.S. CHEN, R.S. HANDLEY, R. DESILVA, B.P. GIRI, TETRAHEDRON LETT., 1987, pages 1159
AHNSTROM, NILSSON, ACTA.CHIM.SCAND, vol. 19, 1966, pages 313
B. VELAN, M. HALMANN, IMMUNOCHEMISTRY, vol. 15, 1978, pages 331
D. E. BAUSE, H. H. PATTERSON, ANAL. CHEM., vol. 51, 1985, pages 2288
D. SLAWIKSKA, J. SIWINSKI, W. PUKACKI, K. POLEWSKI: "Analvtical Application of Bioluminescence and Chemiluminescence", 1979, STATE PUBLISHINQ AND PRINTINA, pages: 239
F. KOHEN, J. B. KIM, G. BARNARD, H. R. LINDER, STEROIDS, vol. 36, 1980, pages 405
G. AHNSTROM, R. NILSSON, ACTA. CHIM. SCAND., vol. 19, 1965, pages 313
G. H. G. THORPE, L. J. KRICKA, E. GILLESPIE, S. MOSELEY, R. AMESS, N. BAGGET, T. P. WHITEHEAD, ANAL. BIOCHEM., vol. 145, 1985, pages 96
G. H. G. THORPE, L. J. KRICKA, S. B. MOSELEY, T. P. WHITEHEAD, CLIN. CHEM. (WINSTON-SALEM, N. C., vol. 31, 1985, pages 1335
H. AKHAVAN-TAFTI, R. DESILVA, Z. ARGHAVANI, R. A. EICKHOLT, R.S. HANDLEY, B.A. SCHOENFELNER, K. SUGIOKA, Y. SUGIOKA, A.P. SCHAAP, J.ORG.CHEM., vol. 63, 1998, pages 930
H. ARAKAWA, M. MAEDA, A. TSUJI, ANAL. BIOCHEM., vol. 97, 1979, pages 248
H. P. MISRA, P. M. SQUATRIOTO, ARCH. BIOCHEM. BIOPHVS., vol. 215, 1982, pages 59
H. R. SCHROEDER, P. O. VOGELHUT, R. J. CARRICO, R. C. BOGUSLASKI, R.T. BUCKLER, ANAL. CHEM., vol. 48, 1976, pages 1933
H. W. YUROW, S. SASS, ANAL. CHIM. ACTA., vol. 88, 1977, pages 389
J. K. WONG, M. L. SALIN, PHOTOCHEM. PHOTOBIOL., vol. 33, 1981, pages 737
J. KRICKA, NATURE (LONDON, vol. 305, 1983, pages 158
K. PUGNET, A.M. MICHELSON, S. AVRAMEAS, ANAL. BIOCHEM., vol. 79, 1977, pages 477 - 456
K. SASAMOTO, Y. OHKURA, CHEM. PHARM. BULL., vol. 39, 1991, pages 411
K.PUGET, A.M. MICHELSON, S. AVRAMEAS, ANAL. BIOCHEM., vol. 79, 1977, pages 447
L. EWETZ, A. THORE, ANAL. BIOCHEM., vol. 71, 1976, pages 564
L. J. KRICKA, M. DELUCA, ARCH. BIOCHEM. BIOPHVS., vol. 217, 1983, pages 674
L.EWETZ, A. THORE, ANAL. BIOCHEM., vol. 71, 1976, pages 564
L.S. HERSH, W.P. VANN, S.A. WILHELM, METHODS IN ENZVMOLOGV, vol. 73, 1981, pages 608
M. HALMANN, B. VELAN, T. SERY, H. SCHUPPER, PHOTOCHEM. PHOTOBIOCHEM., vol. 30, 1979, pages 165
M. HALMANN, B.VELAN, T. SERY, H. SCHUPPER, PHOTOCHEM. PHOTOBIOCHEM., vol. 30, 1979, pages 165
M. L. GRAYESKI, E. WOOLF: "Analvtical Application of Bioluminescence and Chemiluminescence", 1984, ACADEMIC PRESS, pages: 565
See also references of EP1254252A4
T. GOTO, H. FUKATSU, TET. LETTS., 1969, pages 4299
T. KOBAYASHI, K. SAGA, S. SHIMIZU, T. GOTO, AGRIC.BIOL.CHEM., vol. 46, 1981, pages 1403

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
USRE47607E1 (en) 2006-10-24 2019-09-17 Gene Stream Pty Ltd. Luciferase signal enhancing compositions
US8232047B2 (en) 2006-10-24 2012-07-31 Gene Stream Pty Ltd. Luciferase signal enhancing compositions
CN101636503B (en) * 2006-10-24 2012-10-03 基因流股份有限公司 Luciferase signal enhancing composition
EP2843411A1 (en) * 2006-10-24 2015-03-04 Gene Stream Pty Ltd. Luciferase signal enhancing compositions
USRE46199E1 (en) 2006-10-24 2016-11-08 Gene Stream Pty Ltd. Luciferase signal enhancing compositions
WO2008049160A1 (en) * 2006-10-24 2008-05-02 Gene Stream Pty Ltd Luciferase signal enhancng compositions
US11236325B2 (en) 2014-02-10 2022-02-01 Zymo Research Corporation Methods for nucleic acid capture
US9632034B2 (en) 2015-03-13 2017-04-25 Li-Cor, Inc. Fluorogenic and chromogenic substrate
WO2016149127A1 (en) * 2015-03-13 2016-09-22 Li-Cor, Inc. Fluorogenic and chromogenic substrate
JP2019509981A (en) * 2016-01-26 2019-04-11 ラモット・アット・テル・アビブ・ユニバーシテイ・リミテッドＲａｍｏｔ Ａｔ Ｔｅｌ Ａｖｉｖ Ｕｎｉｖｅｒｓｉｔｙ Ｌｔｄ． Chemiluminescent probe for diagnostic and in vivo imaging
IT202000001327A1 (en) * 2020-01-23 2021-07-23 Cyanagen S R L CHEMILUMINESCENT SUBSTRATES FOR PEROXIDASE WITH A LONG SHELF LIFE
EP3855185A1 (en) * 2020-01-23 2021-07-28 Cyanagen Srl Chemiluminescent substrates for peroxidase with extended shelf-life
US11573183B2 (en) 2020-01-23 2023-02-07 Cyanagen S.R.L. Chemiluminescent substrates for peroxidase with extended shelf-life

Also Published As

Publication number Publication date
US20010046688A1 (en) 2001-11-29
AU2001234612A1 (en) 2001-08-07
CA2398812A1 (en) 2001-08-02
IL150924A0 (en) 2003-02-12
EP1254252A4 (en) 2006-06-07
US6602679B2 (en) 2003-08-05
EP1254252A1 (en) 2002-11-06

Similar Documents

Publication Publication Date Title
WO2001055446A1 (en) Novel stabilized formulations for chemiluminescent assays
JP2977895B2 (en) Amplified chemiluminescent assay
JP3171595B2 (en) Luciferase compositions and methods
US5498542A (en) Electrode mediators for regeneration of NADH and NADPH
CA1144859A (en) Diacetyldichlorofluorescin with a source of hydrogen peroxide for assay of peroxidase
Björnberg et al. The activity of Escherichia coli dihydroorotate dehydrogenase is dependent on a conserved loop identified by sequence homology, mutagenesis, and limited proteolysis
AU2003301323A1 (en) Method and reagent for measuring cholesterol in high density lipoproteins
EP0619374A3 (en) Colorimetric determination of analyte using dehydrogenesis of benzyl alcohol and a chromogenic redox indicator.
JPH02174695A (en) Method and reagent for colorimetry of analite by means of enzymic oxidation and direct or coloring electron acceptor therefor
JP4637357B2 (en) Method for detecting ATP
JPS6258718B2 (en)
EP1242440A2 (en) Use of nicotinamide adenine dinucleotide (nad) and nicotinamide adenine dinucleotide phosphate (nadp) analogs to measure enzyme activities, metabolites and substrates
WO2018056431A1 (en) Method for measuring l-kynurenine and measurement kit
Argyrou et al. Catalysis of diaphorase reactions by Mycobacterium tuberculosis lipoamide dehydrogenase occurs at the EH4 level
Björnberg et al. Dihydrooxonate is a substrate of dihydroorotate dehydrogenase (DHOD) providing evidence for involvement of cysteine and serine residues in base catalysis
US4278760A (en) Method and composition for determining an oxidized pyridine co-enzyme
JP2005118014A (en) Method of analysis and reagent used for the same
JP2017063786A (en) L-kynurenine measurement method and measurement kit
Wroczyński et al. Aromatic aldehydes as fluorogenic indicators for human aldehyde dehydrogenases and oxidases: substrate and isozyme specificityPresented as a poster at the VIIIth International Symposium on Luminescence Spectrometry in Biomedical Analysis, Las Palmas de Gran Canaria, Spain, May 1998.
US5858695A (en) Method of quantitative determination of bilirubin and a reagent therefor
JPH03502281A (en) How to measure bilirubin in solution
Hozumi Reaction of the carcinogen 4-hydroxyaminoquinoline 1-oxide with sulfhydryl groups of proteins
Gong et al. A fiber optic biosensor for uric acid based on immobilized enzymes
EP1109930B1 (en) Luciferase assay, compositions and kits for use in connection therewith
JPH09178755A (en) Method and reagent for determining bilirubin

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BY BZ CA CH CN CR CU CZ DE DK DM DZ EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NO NZ PL PT RO RU SD SE SG SI SK SL TJ TM TR TT TZ UA UG UZ VN YU ZA ZW

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE TR BF BJ CF CG CI CM GA GN GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
WWE Wipo information: entry into national phase

Ref document number: 150924

Country of ref document: IL

WWE Wipo information: entry into national phase

Ref document number: IN/PCT/2002/968/KOL

Country of ref document: IN

WWE Wipo information: entry into national phase

Ref document number: 2398812

Country of ref document: CA

WWE Wipo information: entry into national phase

Ref document number: 2001906739

Country of ref document: EP

WWP Wipo information: published in national office

Ref document number: 2001906739

Country of ref document: EP

REG Reference to national code

Ref country code: DE

Ref legal event code: 8642

NENP Non-entry into the national phase

Ref country code: JP