CA1147336A - Produits conjugues chimilumiscents, marques au phtalhydrazide - Google Patents

Produits conjugues chimilumiscents, marques au phtalhydrazide

Info

Publication number: CA1147336A
Authority: CA; Canada
Prior art keywords: amino; derivative; ligand; labeled; binding
Prior art date: 1978-07-24
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

Application number

CA000403936A

Other languages

English (en)

Inventor

Robert T. Buckler

Hartmut R. Schroeder

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.)

Bayer Corp

Original Assignee

Miles Laboratories Inc

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.)

1978-07-24

Filing date

1982-05-27

Publication date

1983-05-31

1978-07-24 Priority claimed from US05/927,621 external-priority patent/US4334069A/en

1982-05-27 Application filed by Miles Laboratories Inc filed Critical Miles Laboratories Inc

1982-05-27 Priority to CA000403936A priority Critical patent/CA1147336A/fr

1983-05-31 Application granted granted Critical

1983-05-31 Publication of CA1147336A publication Critical patent/CA1147336A/fr

Status Expired legal-status Critical Current

Links

KGLPWQKSKUVKMJ-UHFFFAOYSA-N 2,3-dihydrophthalazine-1,4-dione Chemical compound C1=CC=C2C(=O)NNC(=O)C2=C1 KGLPWQKSKUVKMJ-UHFFFAOYSA-N 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 14
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
239000001257 hydrogen Substances 0.000 claims abstract description 11
125000000217 alkyl group Chemical group 0.000 claims abstract description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
239000003446 ligand Substances 0.000 abstract description 48
238000000159 protein binding assay Methods 0.000 abstract description 14
230000009870 specific binding Effects 0.000 abstract description 10
239000007788 liquid Substances 0.000 abstract description 7
238000002360 preparation method Methods 0.000 abstract description 4
239000003153 chemical reaction reagent Substances 0.000 abstract description 2
239000000562 conjugate Substances 0.000 description 38
238000000034 method Methods 0.000 description 25
230000027455 binding Effects 0.000 description 22
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 18
150000001732 carboxylic acid derivatives Chemical group 0.000 description 17
150000001412 amines Chemical class 0.000 description 16
238000005859 coupling reaction Methods 0.000 description 14
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 14
108090000765 processed proteins & peptides Proteins 0.000 description 14
238000010168 coupling process Methods 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
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MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 10
XUIIKFGFIJCVMT-GFCCVEGCSA-N D-thyroxine Chemical compound IC1=CC(C[C@@H](N)C(O)=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 XUIIKFGFIJCVMT-GFCCVEGCSA-N 0.000 description 9
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 9
108090000623 proteins and genes Proteins 0.000 description 9
XUIIKFGFIJCVMT-UHFFFAOYSA-N thyroxine-binding globulin Natural products IC1=CC(CC([NH3+])C([O-])=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 XUIIKFGFIJCVMT-UHFFFAOYSA-N 0.000 description 9
239000002253 acid Substances 0.000 description 8
238000004458 analytical method Methods 0.000 description 8
-1 hypochlorite ions Chemical class 0.000 description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
239000000203 mixture Substances 0.000 description 8
239000007787 solid Substances 0.000 description 8
229940034208 thyroxine Drugs 0.000 description 8
HWYHZTIRURJOHG-UHFFFAOYSA-N luminol Chemical compound O=C1NNC(=O)C2=C1C(N)=CC=C2 HWYHZTIRURJOHG-UHFFFAOYSA-N 0.000 description 7
102000004196 processed proteins & peptides Human genes 0.000 description 7
229910001868 water Inorganic materials 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
125000003277 amino group Chemical group 0.000 description 6
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XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
HUDPLKWXRLNSPC-UHFFFAOYSA-N 4-aminophthalhydrazide Chemical compound O=C1NNC(=O)C=2C1=CC(N)=CC=2 HUDPLKWXRLNSPC-UHFFFAOYSA-N 0.000 description 5
238000003556 assay Methods 0.000 description 5
238000006482 condensation reaction Methods 0.000 description 5
239000007822 coupling agent Substances 0.000 description 5
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XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 5
239000000243 solution Substances 0.000 description 5
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 description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
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125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 4
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XXQBEVHPUKOQEO-UHFFFAOYSA-N potassium superoxide Chemical compound [K+].[K+].[O-][O-] XXQBEVHPUKOQEO-UHFFFAOYSA-N 0.000 description 4
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LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
BMUDPLZKKRQECS-UHFFFAOYSA-K 3-[18-(2-carboxyethyl)-8,13-bis(ethenyl)-3,7,12,17-tetramethylporphyrin-21,24-diid-2-yl]propanoic acid iron(3+) hydroxide Chemical compound [OH-].[Fe+3].[N-]1C2=C(C)C(CCC(O)=O)=C1C=C([N-]1)C(CCC(O)=O)=C(C)C1=CC(C(C)=C1C=C)=NC1=CC(C(C)=C1C=C)=NC1=C2 BMUDPLZKKRQECS-UHFFFAOYSA-K 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
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229940088597 hormone Drugs 0.000 description 3
239000005556 hormone Substances 0.000 description 3
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150000003431 steroids Chemical class 0.000 description 3
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YYNPMMANXKYXCN-LBPRGKRZSA-N (2s)-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]-2-[(2,2,2-trifluoroacetyl)amino]propanoic acid Chemical compound IC1=CC(C[C@@H](C(=O)O)NC(=O)C(F)(F)F)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 YYNPMMANXKYXCN-LBPRGKRZSA-N 0.000 description 2
VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 2
UXFWTIGUWHJKDD-UHFFFAOYSA-N 2-(4-bromobutyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCCCBr)C(=O)C2=C1 UXFWTIGUWHJKDD-UHFFFAOYSA-N 0.000 description 2
UMULKNIDVSBBLE-UHFFFAOYSA-N 3-aminobenzene-1,2-dicarbohydrazide Chemical compound NNC(=O)C1=CC=CC(N)=C1C(=O)NN UMULKNIDVSBBLE-UHFFFAOYSA-N 0.000 description 2
FTOAOBMCPZCFFF-UHFFFAOYSA-N 5,5-diethylbarbituric acid Chemical compound CCC1(CC)C(=O)NC(=O)NC1=O FTOAOBMCPZCFFF-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
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102100025475 Carcinoembryonic antigen-related cell adhesion molecule 5 Human genes 0.000 description 2
102000004190 Enzymes Human genes 0.000 description 2
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JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
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DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
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229960002685 biotin Drugs 0.000 description 2
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LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 2
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DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 2
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230000035945 sensitivity Effects 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229930002534 steroid glycoside Natural products 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
229940014800 succinic anhydride Drugs 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000012360 testing method Methods 0.000 description 1
229960003604 testosterone Drugs 0.000 description 1
150000003515 testosterones Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
229940035722 triiodothyronine Drugs 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
MSRILKIQRXUYCT-UHFFFAOYSA-M valproate semisodium Chemical compound [Na+].CCCC(C(O)=O)CCC.CCCC(C([O-])=O)CCC MSRILKIQRXUYCT-UHFFFAOYSA-M 0.000 description 1
229960000604 valproic acid Drugs 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
150000003722 vitamin derivatives Chemical class 0.000 description 1
229940075420 xanthine Drugs 0.000 description 1

Landscapes

Peptides Or Proteins (AREA)

CA000403936A 1978-07-24 1982-05-27 Produits conjugues chimilumiscents, marques au phtalhydrazide Expired CA1147336A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000403936A CA1147336A (fr)	1978-07-24	1982-05-27	Produits conjugues chimilumiscents, marques au phtalhydrazide

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US927,621		1978-07-24
US05/927,621 US4334069A (en)	1978-07-24	1978-07-24	Chemiluminescent phthalhydrazide-labeled hapten conjugates
CA000330377A CA1137975A (fr)	1978-07-24	1979-06-22	Conjugats chimioluminescents marques au phthalhydrazide
CA000403936A CA1147336A (fr)	1978-07-24	1982-05-27	Produits conjugues chimilumiscents, marques au phtalhydrazide

Publications (1)

Publication Number	Publication Date
CA1147336A true CA1147336A (fr)	1983-05-31

Family

ID=27166301

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000403936A Expired CA1147336A (fr)	1978-07-24	1982-05-27	Produits conjugues chimilumiscents, marques au phtalhydrazide

Country Status (1)

Country	Link
CA (1)	CA1147336A (fr)

1982
- 1982-05-27 CA CA000403936A patent/CA1147336A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2000-05-31	MKEX	Expiry
2023-05-26	MKEX	Expiry	Effective date: 20000531

Publication	Publication Date	Title
CA1137975A (fr)	1982-12-21	Conjugats chimioluminescents marques au phthalhydrazide
CA1146937A (fr)	1983-05-24	Conjugues marques a l'aminophtalhydrazide chimiluminescent, utilisables dans des essais de liaisons specifiques
US5543524A (en)	1996-08-06	Chemiluminescent acridinium salts
EP0195413B1 (fr)	1993-11-18	Dérivés de la pyridine substituée
US5346996A (en)	1994-09-13	Rare earth cryptates, processes for their preparation, synthesis intermediates and application as fluorescent tracers
US4226993A (en)	1980-10-07	Amino-functionalized phthalhydrazides
US4886744A (en)	1989-12-12	Fluorescent conjugates and biological diagnostic assay system
US4687747A (en)	1987-08-18	Phenanthridinium ester as a labelling compound in luminometric immunoassay
US4225485A (en)	1980-09-30	Chemiluminescent naphthalene-1,2-dicarboxylic acid hydrazide-labeled polypeptides and proteins
US4261893A (en)	1981-04-14	Bis-phthalimide intermediates
US4297273A (en)	1981-10-27	Chemiluminescent phthalhydrazide-labeled protein and polypeptide conjugates
US4238395A (en)	1980-12-09	Dimethyl 7-[ω-N-(phthalimido)alkyl]aminonaphthalene-1,2-dicarboxylates
US4331808A (en)	1982-05-25	Chemiluminescent naphthalene-1,2-dicarboxylic acid hydrazide-labeled haptens
CA1147336A (fr)	1983-05-31	Produits conjugues chimilumiscents, marques au phtalhydrazide
US4212805A (en)	1980-07-15	Bis-phthalimides
Buckler et al.	1980	Amino-functionalized phthalhydrazides
US4355165A (en)	1982-10-19	Amino-functionalized phthalhydrazide intermediates
US5783696A (en)	1998-07-21	Special chemiluminescent acridine derivatives
CA1147737A (fr)	1983-06-07	Conjugues chimiluminescents marques a la phtalhydrazide
US4226992A (en)	1980-10-07	Amino-functionalized naphthalene-1,2-dicarboxylic acid hydrozides
CA1148156A (fr)	1983-06-14	Derives a base d'hydrazide d'acide naphtalene-1,2-dicarboxylique
Buckler et al.	1982	Chemiluminescent naphthalene-1, 2-dicarboxylic acid hydrazide-labeled haptens
CA1150283A (fr)	1983-07-19	7-(.omega.-N-(PHTALIMIDO)ALKYL)AMINO-NAPHTALENE-1,2- CARBOXYLATE DE DIMETHYLE ET DERIVES N-ALKYLES
JP3248628B2 (ja)	2002-01-21	化学発光性化合物およびこれを用いるアッセイ法
US4835268A (en)	1989-05-30	Luminescent cyclic hydrazides for analytical assays