CA2033331C - Methode pour deceler une substance grace a la decomposition de dioxetanes induite par voie enzymatique - Google Patents

Methode pour deceler une substance grace a la decomposition de dioxetanes induite par voie enzymatique Download PDF

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Publication number: CA2033331C
Authority: CA; Canada
Prior art keywords: dioxetane; enzyme; group; cleavable group; cycloalkyl
Prior art date: 1989-07-20
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 - Lifetime

Application number

CA002033331A

Other languages

English (en)

Other versions

CA2033331A1 (fr

Inventor

Irena Y. Bronstein

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.)

Applied Biosystems LLC

Original Assignee

Applera Corp

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.)

1989-07-20

Filing date

1990-07-17

Publication date

2006-03-28

1989-07-20 Priority claimed from US07/382,125 external-priority patent/US4978614A/en

1990-07-17 Application filed by Applera Corp filed Critical Applera Corp

1991-01-21 Publication of CA2033331A1 publication Critical patent/CA2033331A1/fr

2006-03-28 Application granted granted Critical

2006-03-28 Publication of CA2033331C publication Critical patent/CA2033331C/fr

2010-07-17 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

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BVTJGGGYKAMDBN-UHFFFAOYSA-N Dioxetane Chemical group C1COO1 BVTJGGGYKAMDBN-UHFFFAOYSA-N 0.000 title claims abstract description 151
239000000126 substance Substances 0.000 title claims abstract description 55
238000000034 method Methods 0.000 title claims description 33
238000000354 decomposition reaction Methods 0.000 title claims description 15
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238000003556 assay Methods 0.000 claims abstract description 55
238000006243 chemical reaction Methods 0.000 claims abstract description 32
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 30
239000001257 hydrogen Substances 0.000 claims abstract description 30
125000001424 substituent group Chemical group 0.000 claims abstract description 27
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 25
125000000217 alkyl group Chemical group 0.000 claims abstract description 14
125000003118 aryl group Chemical group 0.000 claims abstract description 14
125000004404 heteroalkyl group Chemical group 0.000 claims abstract description 14
150000002431 hydrogen Chemical group 0.000 claims abstract description 14
125000003003 spiro group Chemical group 0.000 claims abstract description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 13
125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 13
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 13
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 13
125000005592 polycycloalkyl group Chemical group 0.000 claims abstract description 13
230000009870 specific binding Effects 0.000 claims abstract description 8
230000006872 improvement Effects 0.000 claims abstract description 7
239000012528 membrane Substances 0.000 claims description 70
239000000523 sample Substances 0.000 claims description 55
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ZIOCTOWDUYBVCA-ZOWZHXDVSA-N (3r,4s,5r,6r)-6-(hydroxymethyl)-3-[3-(3'-methoxyspiro[adamantane-2,4'-dioxetane]-3'-yl)phenyl]oxane-2,3,4,5-tetrol Chemical compound O1OC2(C3CC4CC(C3)CC2C4)C1(OC)C(C=1)=CC=CC=1[C@]1(O)C(O)O[C@H](CO)[C@H](O)[C@@H]1O ZIOCTOWDUYBVCA-ZOWZHXDVSA-N 0.000 claims description 12
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YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 claims description 8
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CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 claims description 6
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JPXMTWWFLBLUCD-UHFFFAOYSA-N nitro blue tetrazolium(2+) Chemical compound COC1=CC(C=2C=C(OC)C(=CC=2)[N+]=2N(N=C(N=2)C=2C=CC=CC=2)C=2C=CC(=CC=2)[N+]([O-])=O)=CC=C1[N+]1=NC(C=2C=CC=CC=2)=NN1C1=CC=C([N+]([O-])=O)C=C1 JPXMTWWFLBLUCD-UHFFFAOYSA-N 0.000 description 9
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XZKIHKMTEMTJQX-UHFFFAOYSA-N 4-Nitrophenyl Phosphate Chemical compound OP(O)(=O)OC1=CC=C([N+]([O-])=O)C=C1 XZKIHKMTEMTJQX-UHFFFAOYSA-N 0.000 description 7
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RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
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LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 5
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NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 5
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QRXMUCSWCMTJGU-UHFFFAOYSA-N 5-bromo-4-chloro-3-indolyl phosphate Chemical compound C1=C(Br)C(Cl)=C2C(OP(O)(=O)O)=CNC2=C1 QRXMUCSWCMTJGU-UHFFFAOYSA-N 0.000 description 4
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239000007800 oxidant agent Substances 0.000 description 1
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RJSRSRITMWVIQT-UHFFFAOYSA-N quinolin-6-amine Chemical compound N1=CC=CC2=CC(N)=CC=C21 RJSRSRITMWVIQT-UHFFFAOYSA-N 0.000 description 1
OVYWMEWYEJLIER-UHFFFAOYSA-N quinolin-6-ol Chemical compound N1=CC=CC2=CC(O)=CC=C21 OVYWMEWYEJLIER-UHFFFAOYSA-N 0.000 description 1
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239000012488 sample solution Substances 0.000 description 1
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ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
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235000021286 stilbenes Nutrition 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
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150000003460 sulfonic acids Chemical class 0.000 description 1
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YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
ABZLKHKQJHEPAX-UHFFFAOYSA-N tetramethylrhodamine Chemical compound C=12C=CC(N(C)C)=CC2=[O+]C2=CC(N(C)C)=CC=C2C=1C1=CC=CC=C1C([O-])=O ABZLKHKQJHEPAX-UHFFFAOYSA-N 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
210000001685 thyroid gland Anatomy 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
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235000011178 triphosphate Nutrition 0.000 description 1
UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
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GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
239000012588 trypsin Substances 0.000 description 1
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238000007794 visualization technique Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1

Landscapes

Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)

CA002033331A 1989-07-20 1990-07-17 Methode pour deceler une substance grace a la decomposition de dioxetanes induite par voie enzymatique Expired - Lifetime CA2033331C (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US07/382,125 US4978614A (en)	1988-10-26	1989-07-20	Method of detecting a substance using enzymatically-induced decomposition of dioxetanes
US382,125		1989-07-20
PCT/US1990/003920 WO1991001492A1 (fr)	1989-07-20	1990-07-17	Procede de detection d'une substance par decomposition induite de maniere enzymatique de dioxetanes

Publications (2)

Publication Number	Publication Date
CA2033331A1 CA2033331A1 (fr)	1991-01-21
CA2033331C true CA2033331C (fr)	2006-03-28

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Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002033331A Expired - Lifetime CA2033331C (fr)	1989-07-20	1990-07-17	Methode pour deceler une substance grace a la decomposition de dioxetanes induite par voie enzymatique

Country Status (1)

Country	Link
CA (1)	CA2033331C (fr)

1990
- 1990-07-17 CA CA002033331A patent/CA2033331C/fr not_active Expired - Lifetime

Also Published As

Publication number	Publication date
CA2033331A1 (fr)	1991-01-21

Publication	Publication Date	Title
US4978614A (en)	1990-12-18	Method of detecting a substance using enzymatically-induced decomposition of dioxetanes
US6514717B2 (en)	2003-02-04	Kit for conducting an assay to detect a substance using enzymatically-induced decomposition of dioxetanes
US5220005A (en)	1993-06-15	Substituted adamantyl dioxetanes
JP2922237B2 (ja)	1999-07-19	化学発光性１，２―ジオキセタン類の改良使用法
US5112960A (en)	1992-05-12	Chemiluminescent 3-(substituted adamant-2'-ylidene) 1,2-dioxetanes
US7053208B2 (en)	2006-05-30	Dioxetane labeled probes and detection assays employing the same
US5543295A (en)	1996-08-06	Chemiluminescent 3--(Substituted adamant--2'--Ylidene) 1,2--Dioxetanes
JP4074335B2 (ja)	2008-04-09	電子数の多い化学発光性アリール置換１，２−ジオキセタン
EP0497972B1 (fr)	1998-12-23	1,2-dioxetanes d'adamant-2'-ylidene a substitution en position 3 chimioluminescents
US5605795A (en)	1997-02-25	Assays using chemiluminescent, enzymatically cleavable substituted 1,2-dioxetanes and kits therefor
USRE36536E (en)	2000-01-25	Method of detecting a substance using enzymatically-induced decomposition of dioxetanes
CA2033331C (fr)	2006-03-28	Methode pour deceler une substance grace a la decomposition de dioxetanes induite par voie enzymatique
US5108934A (en)	1992-04-28	Quantitative immunoassay utilizing liposomes
AU704940B2 (en)	1999-05-06	Chemiluminescent energy transfer assays
JP3177964B2 (ja)	2001-06-18	発色方法、該方法を用いる酵素免疫測定法及びイムノクロマト法
JP2999810B2 (ja)	2000-01-17	１，２−ジオキセタン化合物
JPH1121285A (ja)	1999-01-26	化学発光性１，２−ジオキセタン化合物

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