DE19534988A1 - Verfahren zur Herstellung und Anwendung synthetischer, biotinylierter Peptide - Google Patents

Verfahren zur Herstellung und Anwendung synthetischer, biotinylierter Peptide

Info

Publication number: DE19534988A1
Authority: DE; Germany
Prior art keywords: peptides; biotin; peptide; detector; labeled
Prior art date: 1995-09-21
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 Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn

Application number

DE1995134988

Other languages

German (de)

English (en)

Inventor

Knut Dr Rer Nat Adermann

Wolf-Georg Prof Dr M Forssmann

Andreas Dr Med Kist

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.)

1995-09-21

Filing date

1995-09-21

Publication date

1997-03-27

1995-09-21 Application filed by Individual filed Critical Individual

1995-09-21 Priority to DE1995134988 priority Critical patent/DE19534988A1/de

1996-09-21 Priority to AU72122/96A priority patent/AU7212296A/en

1996-09-21 Priority to PCT/EP1996/004136 priority patent/WO1997011372A1/fr

1996-09-21 Priority to JP9512397A priority patent/JPH11512527A/ja

1996-09-21 Priority to EP96933353A priority patent/EP0874989A1/fr

1997-03-27 Publication of DE19534988A1 publication Critical patent/DE19534988A1/de

Status Withdrawn legal-status Critical Current

Links

108090000765 processed proteins & peptides Proteins 0.000 title claims description 67
102000004196 processed proteins & peptides Human genes 0.000 title claims description 43
238000000034 method Methods 0.000 title description 13
239000000126 substance Substances 0.000 claims abstract description 9
238000003018 immunoassay Methods 0.000 claims abstract 2
239000000203 mixture Substances 0.000 claims abstract 2
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 50
229960002685 biotin Drugs 0.000 claims description 21
235000020958 biotin Nutrition 0.000 claims description 21
239000011616 biotin Substances 0.000 claims description 21
102000004169 proteins and genes Human genes 0.000 claims description 5
108090000623 proteins and genes Proteins 0.000 claims description 5
238000002372 labelling Methods 0.000 claims description 4
238000012512 characterization method Methods 0.000 claims description 2
238000000926 separation method Methods 0.000 claims description 2
102000005962 receptors Human genes 0.000 claims 4
108020003175 receptors Proteins 0.000 claims 4
108050001286 Somatostatin Receptor Proteins 0.000 claims 1
102000011096 Somatostatin receptor Human genes 0.000 claims 1
238000001042 affinity chromatography Methods 0.000 claims 1
208000002458 carcinoid tumor Diseases 0.000 claims 1
238000001514 detection method Methods 0.000 claims 1
238000003745 diagnosis Methods 0.000 claims 1
238000002405 diagnostic procedure Methods 0.000 claims 1
201000010099 disease Diseases 0.000 claims 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
238000000684 flow cytometry Methods 0.000 claims 1
238000000799 fluorescence microscopy Methods 0.000 claims 1
230000003834 intracellular effect Effects 0.000 claims 1
239000011159 matrix material Substances 0.000 claims 1
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238000011002 quantification Methods 0.000 claims 1
230000001105 regulatory effect Effects 0.000 claims 1
239000007790 solid phase Substances 0.000 claims 1
239000000758 substrate Substances 0.000 abstract description 8
125000003636 chemical group Chemical group 0.000 abstract 2
239000011347 resin Substances 0.000 description 17
229920005989 resin Polymers 0.000 description 17
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
125000001151 peptidyl group Chemical group 0.000 description 13
238000003786 synthesis reaction Methods 0.000 description 12
-1 9-fluorenylmethoxycarbonyl Chemical group 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
239000004472 Lysine Substances 0.000 description 9
125000003277 amino group Chemical group 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 8
125000004057 biotinyl group Chemical group [H]N1C(=O)N([H])[C@]2([H])[C@@]([H])(SC([H])([H])[C@]12[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 description 8
210000004899 c-terminal region Anatomy 0.000 description 8
238000010647 peptide synthesis reaction Methods 0.000 description 8
125000006239 protecting group Chemical group 0.000 description 8
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 7
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150000001413 amino acids Chemical group 0.000 description 5
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KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
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DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
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SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
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125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
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150000002668 lysine derivatives Chemical class 0.000 description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 2
HQFLTUZKIRYQSP-UHFFFAOYSA-N 3-ethyl-2h-1,3-benzothiazole-6-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2N(CC)CSC2=C1 HQFLTUZKIRYQSP-UHFFFAOYSA-N 0.000 description 2
108091003079 Bovine Serum Albumin Proteins 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
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102000004160 Phosphoric Monoester Hydrolases Human genes 0.000 description 2
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WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
239000012317 TBTU Substances 0.000 description 2
CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 2
239000012190 activator Substances 0.000 description 2
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238000003556 assay Methods 0.000 description 2
230000006287 biotinylation Effects 0.000 description 2
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239000007795 chemical reaction product Substances 0.000 description 2
BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
239000012634 fragment Substances 0.000 description 2
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
108091005979 iodinated proteins Proteins 0.000 description 2
125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 2
238000004949 mass spectrometry Methods 0.000 description 2
QYSGYZVSCZSLHT-UHFFFAOYSA-N octafluoropropane Chemical compound FC(F)(F)C(F)(F)C(F)(F)F QYSGYZVSCZSLHT-UHFFFAOYSA-N 0.000 description 2
NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
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239000002904 solvent Substances 0.000 description 2
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JYEVQYFWINBXJU-QFIPXVFZSA-N (2s)-6-(9h-fluoren-9-ylmethoxycarbonylamino)-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoic acid Chemical compound C1=CC=C2C(COC(=O)NCCCC[C@H](NC(=O)OC(C)(C)C)C(O)=O)C3=CC=CC=C3C2=C1 JYEVQYFWINBXJU-QFIPXVFZSA-N 0.000 description 1
DHBXNPKRAUYBTH-UHFFFAOYSA-N 1,1-ethanedithiol Chemical compound CC(S)S DHBXNPKRAUYBTH-UHFFFAOYSA-N 0.000 description 1
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
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 1
YRNWIFYIFSBPAU-UHFFFAOYSA-N 4-[4-(dimethylamino)phenyl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C1=CC=C(N(C)C)C=C1 YRNWIFYIFSBPAU-UHFFFAOYSA-N 0.000 description 1
102000002260 Alkaline Phosphatase Human genes 0.000 description 1
108020004774 Alkaline Phosphatase Proteins 0.000 description 1
125000001433 C-terminal amino-acid group Chemical group 0.000 description 1
238000002965 ELISA Methods 0.000 description 1
101001135770 Homo sapiens Parathyroid hormone Proteins 0.000 description 1
101001135995 Homo sapiens Probable peptidyl-tRNA hydrolase Proteins 0.000 description 1
102000018071 Immunoglobulin Fc Fragments Human genes 0.000 description 1
108010091135 Immunoglobulin Fc Fragments Proteins 0.000 description 1
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
108020001621 Natriuretic Peptide Proteins 0.000 description 1
102000004571 Natriuretic peptide Human genes 0.000 description 1
102000003982 Parathyroid hormone Human genes 0.000 description 1
108090000445 Parathyroid hormone Proteins 0.000 description 1
229920001213 Polysorbate 20 Polymers 0.000 description 1
RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 1
230000004913 activation Effects 0.000 description 1
229960002684 aminocaproic acid Drugs 0.000 description 1
239000000427 antigen Substances 0.000 description 1
102000036639 antigens Human genes 0.000 description 1
108091007433 antigens Proteins 0.000 description 1
239000012131 assay buffer Substances 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
XJMXIWNOKIEIMX-UHFFFAOYSA-N bromo chloro 1h-indol-2-yl phosphate Chemical compound C1=CC=C2NC(OP(=O)(OBr)OCl)=CC2=C1 XJMXIWNOKIEIMX-UHFFFAOYSA-N 0.000 description 1
238000005251 capillar electrophoresis Methods 0.000 description 1
239000005018 casein Substances 0.000 description 1
BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
235000021240 caseins Nutrition 0.000 description 1
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238000004090 dissolution Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
102000058004 human PTH Human genes 0.000 description 1
239000003547 immunosorbent Substances 0.000 description 1
238000011534 incubation Methods 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
235000019796 monopotassium phosphate Nutrition 0.000 description 1
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235000019799 monosodium phosphate Nutrition 0.000 description 1
CMWYAOXYQATXSI-UHFFFAOYSA-N n,n-dimethylformamide;piperidine Chemical compound CN(C)C=O.C1CCNCC1 CMWYAOXYQATXSI-UHFFFAOYSA-N 0.000 description 1
239000000692 natriuretic peptide Substances 0.000 description 1
229930014626 natural product Natural products 0.000 description 1
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 1
239000000199 parathyroid hormone Substances 0.000 description 1
229960001319 parathyroid hormone Drugs 0.000 description 1
102000013415 peroxidase activity proteins Human genes 0.000 description 1
108040007629 peroxidase activity proteins Proteins 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
150000004714 phosphonium salts Chemical class 0.000 description 1
PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000002953 preparative HPLC Methods 0.000 description 1
230000002285 radioactive effect Effects 0.000 description 1
230000007420 reactivation Effects 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
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238000012163 sequencing technique Methods 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
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Classifications

- 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
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
- G01N33/543—Immunoassay; Biospecific binding assay; Materials therefor with an insoluble carrier for immobilising immunochemicals
- G01N33/54306—Solid-phase reaction mechanisms
- 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
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
- G01N33/531—Production of immunochemical test materials
- G01N33/532—Production of labelled immunochemicals
- 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
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
- G01N33/543—Immunoassay; Biospecific binding assay; Materials therefor with an insoluble carrier for immobilising immunochemicals
- G01N33/54353—Immunoassay; Biospecific binding assay; Materials therefor with an insoluble carrier for immobilising immunochemicals with ligand attached to the carrier via a chemical coupling agent
- 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
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
- G01N33/543—Immunoassay; Biospecific binding assay; Materials therefor with an insoluble carrier for immobilising immunochemicals
- G01N33/54393—Improving reaction conditions or stability, e.g. by coating or irradiation of surface, by reduction of non-specific binding, by promotion of specific binding
- 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
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
- G01N33/543—Immunoassay; Biospecific binding assay; Materials therefor with an insoluble carrier for immobilising immunochemicals
- G01N33/544—Immunoassay; Biospecific binding assay; Materials therefor with an insoluble carrier for immobilising immunochemicals the carrier being organic
- G01N33/545—Synthetic resin
- G01N33/547—Synthetic resin with antigen or antibody attached to the carrier via a bridging agent

Landscapes

Health & Medical Sciences (AREA)
Immunology (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Chemical & Material Sciences (AREA)
Hematology (AREA)
Urology & Nephrology (AREA)
Biomedical Technology (AREA)
Molecular Biology (AREA)
Microbiology (AREA)
Analytical Chemistry (AREA)
Biotechnology (AREA)
Pathology (AREA)
Food Science & Technology (AREA)
Medicinal Chemistry (AREA)
Physics & Mathematics (AREA)
Cell Biology (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
General Physics & Mathematics (AREA)
Chemical Kinetics & Catalysis (AREA)
Peptides Or Proteins (AREA)
Investigating Or Analysing Biological Materials (AREA)

DE1995134988 1995-09-21 1995-09-21 Verfahren zur Herstellung und Anwendung synthetischer, biotinylierter Peptide Withdrawn DE19534988A1 (de)

Priority Applications (5)

Application Number	Priority Date	Filing Date	Title
DE1995134988 DE19534988A1 (de)	1995-09-21	1995-09-21	Verfahren zur Herstellung und Anwendung synthetischer, biotinylierter Peptide
AU72122/96A AU7212296A (en)	1995-09-21	1996-09-21	Immunoassay with the aid of a mixture of detector molecules forming a detector substance
PCT/EP1996/004136 WO1997011372A1 (fr)	1995-09-21	1996-09-21	Dosage immunologique a l'aide d'un melange de molecules detectrices formant une substance detectrice
JP9512397A JPH11512527A (ja)	1995-09-21	1996-09-21	検出用物質を形成する検出分子の混合物によるイムノアッセイ
EP96933353A EP0874989A1 (fr)	1995-09-21	1996-09-21	Dosage immunologique a l'aide d'un melange de molecules detectrices formant une substance detectrice

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE1995134988 DE19534988A1 (de)	1995-09-21	1995-09-21	Verfahren zur Herstellung und Anwendung synthetischer, biotinylierter Peptide

Publications (1)

Publication Number	Publication Date
DE19534988A1 true DE19534988A1 (de)	1997-03-27

Family

ID=7772713

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE1995134988 Withdrawn DE19534988A1 (de)	1995-09-21	1995-09-21	Verfahren zur Herstellung und Anwendung synthetischer, biotinylierter Peptide

Country Status (5)

Country	Link
EP (1)	EP0874989A1 (fr)
JP (1)	JPH11512527A (fr)
AU (1)	AU7212296A (fr)
DE (1)	DE19534988A1 (fr)
WO (1)	WO1997011372A1 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
MX365465B (es)	2013-03-21	2019-06-04	Sanofi Aventis Deutschland	Sintesis de productos peptidicos que contienen imida ciclica.
MX363522B (es)	2013-03-21	2019-03-26	Sanofi Aventis Deutschland	Síntesis de productos peptídicos que contienen hidantoína.
CN106866793B (zh) *	2015-12-14	2022-04-19	韩苏	一种多肽化合物及其制备方法与应用
EP3818375A4 (fr) *	2018-07-02	2021-10-13	Siemens Healthcare Diagnostics, Inc.	Mesure d'auto-anticorps par dosage immunologique direct

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GR850899B (fr) *	1984-04-12	1985-11-25	Gen Hospital Corp
CA2015938C (fr) *	1989-05-02	1999-09-07	Kevin M. Knigge	Liaison covalente d'elements specifiques a une base solide
JP2619549B2 (ja) *	1989-06-29	1997-06-11	日本商事株式会社	抗原の定量法およびそれに用いる固相
DK0891982T3 (da) *	1992-03-06	2007-09-03	Innogenetics Nv	HIV-peptider

1995
- 1995-09-21 DE DE1995134988 patent/DE19534988A1/de not_active Withdrawn
1996
- 1996-09-21 EP EP96933353A patent/EP0874989A1/fr not_active Withdrawn
- 1996-09-21 AU AU72122/96A patent/AU7212296A/en not_active Abandoned
- 1996-09-21 WO PCT/EP1996/004136 patent/WO1997011372A1/fr not_active Ceased
- 1996-09-21 JP JP9512397A patent/JPH11512527A/ja active Pending

Also Published As

Publication number	Publication date
WO1997011372A1 (fr)	1997-03-27
AU7212296A (en)	1997-04-09
JPH11512527A (ja)	1999-10-26
EP0874989A1 (fr)	1998-11-04

Publication	Publication Date	Title
EP0220245B1 (fr)	1992-07-08	Methode de determination de mimotopes
Hirsch et al.	2002	Easily reversible desthiobiotin binding to streptavidin, avidin, and other biotin-binding proteins: uses for protein labeling, detection, and isolation
EP0089008B1 (fr)	1990-08-08	Antisérum hautement specifique contre le peptide procollagèneCol 1 (Type III) et le peptide procollagène (Type III), sa préparation et son utilisation.
DE3586772T2 (de)	1993-03-04	Verfahren zur bestimmung von mimotopen.
DE69637136T2 (de)	2008-02-21	Screening von kombinatorischen Peptidbibliotheken zur Selektion von Peptidliganden zur Verwendung in der Affinitätsreinigung von Zielproteinen
EP0379949B1 (fr)	1995-03-29	Procédé de détermination des anticorps-HIV
DE69116034T2 (de)	1996-06-20	Immunotestreagenzien und Verfahren zur Bestimmung von Cyclosporin
DE69029092T2 (de)	1997-04-17	Synthetische Antigene zum Nachweis von Antikörpern gegen Hepatitis C-Virus
Leeb-Lundberg et al.	1984	Photoaffinity labeling of mammalian alpha 1-adrenergic receptors. Identification of the ligand binding subunit with a high affinity radioiodinated probe.
DE69119656T2 (de)	1996-12-05	Satz zur spezifischen Bestimmung von Angiotensin-II
JPH0210159A (ja)	1990-01-12	螢光偏光免疫検定法原理によるタンパク質の測定方法およびハイブリッドクローン
US5925533A (en)	1999-07-20	Tropinin I calibrator and method of use thereof in a sandwich immunoassay
EP0922958B1 (fr)	2002-10-02	Réduction d'interférence dans les méthodes diagnostiques utilisants les peptides comportant les D-acides amines
JPH06506056A (ja)	1994-07-07	Ｍｈｃ抗原によるペプチド結合検定法
DE19534988A1 (de)	1997-03-27	Verfahren zur Herstellung und Anwendung synthetischer, biotinylierter Peptide
DE68927283T2 (de)	1997-04-24	HCG-Peptide zur Verwendung in Antikörper-Reinigungsverfahren
EP0741869A1 (fr)	1996-11-13	Substances de fixation specifiques pour anticorps et leur utilisation dans des dosages immunologiques ou des vaccins
DE69816241T2 (de)	2004-04-15	Aktivierte peptide und konjugate
DE3014582C2 (fr)	1990-11-08
DE3781745T2 (de)	1993-02-04	Antikoerper zur verwendung fuer die bestimmung von menschlichem glycoalbumin.
JPS6311626B2 (fr)	1988-03-15
EP1945798B1 (fr)	2013-05-22	Procede pour determiner l'aptitude au clivage de substrats
DE69635753T2 (de)	2006-09-14	Verbesserte hapten-peptidkonjugaten zum nachweis von anti-hiv-1 oder anti-hiv-2 antikörpern
CN110317254A (zh)	2019-10-11	人mbp抗原表位肽、抗原、抗体、应用及化学发光试剂盒
DE69817807T2 (de)	2004-07-15	IMMUNOASSAY UND KIT FÜR IgA ANTIKÖRPER, SPEZIFISCH FÜR ACETALDEHYD-ADDUKTE

Legal Events

Date	Code	Title	Description
1998-09-17	8139	Disposal/non-payment of the annual fee