WO2001055446A1 - Novel stabilized formulations for chemiluminescent assays - Google Patents

Novel stabilized formulations for chemiluminescent assays Download PDF

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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
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WO
WIPO (PCT)
Prior art keywords
substrate
substituted
acid
probe
group
Prior art date
Application number
PCT/US2001/002779
Other languages
French (fr)
Inventor
Brij Pal Giri
Original Assignee
Brij Pal Giri
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 Brij Pal Giri filed Critical Brij Pal Giri
Priority to CA002398812A priority Critical patent/CA2398812A1/en
Priority to AU2001234612A priority patent/AU2001234612A1/en
Priority to EP01906739A priority patent/EP1254252A4/en
Priority to IL15092401A priority patent/IL150924A0/en
Publication of WO2001055446A1 publication Critical patent/WO2001055446A1/en

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    • 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

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 WO2001055446A1 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
CA002398812A CA2398812A1 (en) 2000-01-28 2001-01-26 Novel stabilized formulations for chemiluminescent assays
AU2001234612A AU2001234612A1 (en) 2000-01-28 2001-01-26 Novel stabilized formulations for chemiluminescent assays
EP01906739A EP1254252A4 (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

Applications Claiming Priority (2)

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US17862600P 2000-01-28 2000-01-28
US60/178,626 2000-01-28

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

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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
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

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US7300766B2 (en) * 2002-05-23 2007-11-27 Giri Brij P Polymeric ammonium and or phosphonium salts having added π-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
US20050019778A1 (en) * 2003-07-17 2005-01-27 Voyta John C. Sequential generation of multiple chemiluminescent signals on solid supports
US20050026151A1 (en) * 2003-07-17 2005-02-03 Voyta John C. Simultaneous generation of multiple chemiluminescent signals on solid supports
CA2562684A1 (en) * 2004-04-14 2006-07-13 Brij P. Giri New ultra-sensitive chemiluminescent substrates for enzymes and their conjugates
US20050272108A1 (en) * 2004-05-21 2005-12-08 Bhanu Kalra Stabilized two component system for chemiluminescent 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
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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
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US10605807B2 (en) 2016-02-24 2020-03-31 Bio-Rad Laboratories, Inc. Methods and compositions for fluorescence detection
US11384381B2 (en) * 2016-07-13 2022-07-12 Kikkoman Corporation Reaction accelerating agent
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
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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 enhancng compositions
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
USRE47607E1 (en) 2006-10-24 2019-09-17 Gene Stream Pty Ltd. Luciferase signal enhancing compositions
US11236325B2 (en) 2014-02-10 2022-02-01 Zymo Research Corporation Methods for nucleic acid capture
WO2016149127A1 (en) * 2015-03-13 2016-09-22 Li-Cor, Inc. Fluorogenic and chromogenic substrate
US9632034B2 (en) 2015-03-13 2017-04-25 Li-Cor, Inc. Fluorogenic and chromogenic substrate
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

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

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