CS276659B6 - Method and means for maleic imide groups determination - Google Patents

Method and means for maleic imide groups determination Download PDF

Info

Publication number: CS276659B6
Authority: CS; Czechoslovakia
Prior art keywords: groups; maleimide; thiol; determination; reagent
Prior art date: 1988-12-19

Application number

CS896935A

Other languages

Czech (cs)

English (en)

Other versions

CS693589A3 (en

Inventor

Michael Dreher

Heinz Hirsch

Original Assignee

Merck Patent Gmbh

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.)

1988-12-19

Filing date

1989-12-07

Publication date

1992-07-15

1989-12-07 Application filed by Merck Patent Gmbh filed Critical Merck Patent Gmbh

1992-03-18 Publication of CS693589A3 publication Critical patent/CS693589A3/cs

1992-07-15 Publication of CS276659B6 publication Critical patent/CS276659B6/cs

Links

238000000034 method Methods 0.000 title claims description 17
PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical group O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 title description 2
125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 claims description 30
125000003396 thiol group Chemical group [H]S* 0.000 claims description 21
239000003153 chemical reaction reagent Substances 0.000 claims description 11
102000004169 proteins and genes Human genes 0.000 claims description 11
108090000623 proteins and genes Proteins 0.000 claims description 11
DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 claims description 5
239000000203 mixture Substances 0.000 claims description 5
DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 claims description 5
AEUVIXACNOXTBX-UHFFFAOYSA-N 1-sulfanylpropan-1-ol Chemical compound CCC(O)S AEUVIXACNOXTBX-UHFFFAOYSA-N 0.000 claims description 2
150000003573 thiols Chemical class 0.000 claims 1
239000000243 solution Substances 0.000 description 17
235000018102 proteins Nutrition 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
KIUMMUBSPKGMOY-UHFFFAOYSA-N 3,3'-Dithiobis(6-nitrobenzoic acid) Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC(SSC=2C=C(C(=CC=2)[N+]([O-])=O)C(O)=O)=C1 KIUMMUBSPKGMOY-UHFFFAOYSA-N 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
-1 succinimidyl group Chemical group 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
238000005259 measurement Methods 0.000 description 4
PMJWDPGOWBRILU-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[4-(2,5-dioxopyrrol-1-yl)phenyl]butanoate Chemical compound O=C1CCC(=O)N1OC(=O)CCCC(C=C1)=CC=C1N1C(=O)C=CC1=O PMJWDPGOWBRILU-UHFFFAOYSA-N 0.000 description 3
239000004971 Cross linker Substances 0.000 description 3
102000004190 Enzymes Human genes 0.000 description 3
108090000790 Enzymes Proteins 0.000 description 3
108010001336 Horseradish Peroxidase Proteins 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000000975 dye Substances 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
239000000126 substance Substances 0.000 description 3
ZLANMTTYEJHZIE-UHFFFAOYSA-N 4-(2,5-dioxopyrrol-1-yl)benzenediazonium Chemical compound O=C1C=CC(=O)N1C1=CC=C([N+]#N)C=C1 ZLANMTTYEJHZIE-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
102000008394 Immunoglobulin Fragments Human genes 0.000 description 2
108010021625 Immunoglobulin Fragments Proteins 0.000 description 2
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
HAXFWIACAGNFHA-UHFFFAOYSA-N aldrithiol Chemical compound C=1C=CC=NC=1SSC1=CC=CC=N1 HAXFWIACAGNFHA-UHFFFAOYSA-N 0.000 description 2
238000003556 assay Methods 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
239000003623 enhancer Substances 0.000 description 2
238000003018 immunoassay Methods 0.000 description 2
238000011534 incubation Methods 0.000 description 2
QWXYZCJEXYQNEI-OSZHWHEXSA-N intermediate I Chemical compound COC(=O)[C@@]1(C=O)[C@H]2CC=[N+](C\C2=C\C)CCc2c1[nH]c1ccccc21 QWXYZCJEXYQNEI-OSZHWHEXSA-N 0.000 description 2
CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
DIYPCWKHSODVAP-UHFFFAOYSA-N 1-[3-(2,5-dioxopyrrol-1-yl)benzoyl]oxy-2,5-dioxopyrrolidine-3-sulfonic acid Chemical compound O=C1C(S(=O)(=O)O)CC(=O)N1OC(=O)C1=CC=CC(N2C(C=CC2=O)=O)=C1 DIYPCWKHSODVAP-UHFFFAOYSA-N 0.000 description 1
VHYRLCJMMJQUBY-UHFFFAOYSA-N 1-[4-[4-(2,5-dioxopyrrol-1-yl)phenyl]butanoyloxy]-2,5-dioxopyrrolidine-3-sulfonic acid Chemical compound O=C1C(S(=O)(=O)O)CC(=O)N1OC(=O)CCCC1=CC=C(N2C(C=CC2=O)=O)C=C1 VHYRLCJMMJQUBY-UHFFFAOYSA-N 0.000 description 1
IYGAMTQMILRCCI-UHFFFAOYSA-N 3-aminopropane-1-thiol Chemical compound NCCCS IYGAMTQMILRCCI-UHFFFAOYSA-N 0.000 description 1
102000014914 Carrier Proteins Human genes 0.000 description 1
BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 1
HDFGOPSGAURCEO-UHFFFAOYSA-N N-ethylmaleimide Chemical compound CCN1C(=O)C=CC1=O HDFGOPSGAURCEO-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 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
229960005070 ascorbic acid Drugs 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
108091008324 binding proteins Proteins 0.000 description 1
230000008033 biological extinction Effects 0.000 description 1
229910021538 borax Inorganic materials 0.000 description 1
238000004364 calculation method Methods 0.000 description 1
HDFRDWFLWVCOGP-UHFFFAOYSA-N carbonothioic O,S-acid Chemical class OC(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-N 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000007942 carboxylates Chemical class 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 1
XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
235000018417 cysteine Nutrition 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000012634 fragment Substances 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
125000005462 imide group Chemical group 0.000 description 1
230000036039 immunity Effects 0.000 description 1
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229960003151 mercaptamine Drugs 0.000 description 1
238000003908 quality control method Methods 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000006894 reductive elimination reaction Methods 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
235000010339 sodium tetraborate Nutrition 0.000 description 1
125000006850 spacer group Chemical group 0.000 description 1
BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
239000001043 yellow dye Substances 0.000 description 1

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
- G01N33/52—Use of compounds or compositions for colorimetric, spectrophotometric or fluorometric investigation, e.g. use of reagent paper and including single- and multilayer analytical elements
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/14—Heterocyclic carbon compound [i.e., O, S, N, Se, Te, as only ring hetero atom]
- Y10T436/145555—Hetero-N
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/17—Nitrogen containing

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Hematology (AREA)
Immunology (AREA)
Engineering & Computer Science (AREA)
Molecular Biology (AREA)
Biomedical Technology (AREA)
Chemical & Material Sciences (AREA)
Urology & Nephrology (AREA)
Food Science & Technology (AREA)
Biochemistry (AREA)
Cell Biology (AREA)
Biotechnology (AREA)
Medicinal Chemistry (AREA)
Physics & Mathematics (AREA)
Analytical Chemistry (AREA)
Microbiology (AREA)
General Health & Medical Sciences (AREA)
General Physics & Mathematics (AREA)
Pathology (AREA)
Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
Investigating Or Analysing Biological Materials (AREA)

CS896935A 1988-12-19 1989-12-07 Method and means for maleic imide groups determination CS276659B6 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE3842657A DE3842657A1 (de)	1988-12-19	1988-12-19	Verfahren und mittel zur bestimmung von maleimidgruppen

Publications (2)

Publication Number	Publication Date
CS693589A3 CS693589A3 (en)	1992-03-18
CS276659B6 true CS276659B6 (en)	1992-07-15

Family

ID=6369494

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS896935A CS276659B6 (en)	1988-12-19	1989-12-07	Method and means for maleic imide groups determination

Country Status (6)

Country	Link
US (1)	US5132226A (fr)
EP (1)	EP0374620A3 (fr)
JP (1)	JPH02227098A (fr)
CS (1)	CS276659B6 (fr)
DE (1)	DE3842657A1 (fr)
IL (1)	IL92777A0 (fr)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
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US5350674A (en) *	1992-09-04	1994-09-27	Becton, Dickinson And Company	Intrinsic factor - horse peroxidase conjugates and a method for increasing the stability thereof
US5791868A (en) *	1996-06-14	1998-08-11	Capstone Turbine Corporation	Thrust load compensating system for a compliant foil hydrodynamic fluid film thrust bearing
US6437092B1 (en) *	1998-11-06	2002-08-20	Conjuchem, Inc.	Conjugates of opioids and endogenous carriers
RU2156454C2 (ru) *	1998-11-12	2000-09-20	Алтайский государственный университет	Определение малеинимидов в виде солей аци-форм
RU2164678C2 (ru) *	1999-03-26	2001-03-27	Алтайский государственный технический университет им. И.И. Ползунова	Способ количественного определения n-фенилмалеинимида
RU2163371C2 (ru) *	1999-04-14	2001-02-20	Алтайский государственный университет	Способ количественного определения n-замещенных малеинимидов
RU2175124C1 (ru) *	2000-02-14	2001-10-20	Алтайский государственный университет	Способ количественного определения дималеинимидов
US7666661B2 (en)	2001-08-27	2010-02-23	Platypus Technologies, Llc	Substrates, devices, and methods for quantitative liquid crystal assays
RU2215283C2 (ru) *	2001-10-10	2003-10-27	Алтайский государственный университет	Способ количественного определения гексаметилендималеинимида
EP2093565B1 (fr) *	2002-05-22	2014-11-19	Platypus Technologies, Inc.	Utilisation des dispositifs et procédés pour les réseaux cellulaires
RU2229698C2 (ru) *	2002-07-02	2004-05-27	Алтайский государственный университет	Определение малеинимидов в смесях
AU2004262301A1 (en)	2003-07-25	2005-02-10	Platypus Technologies, Llc	Liquid crystal based analyte detection
CA2545482A1 (fr)	2003-11-10	2005-05-26	Platypus Technologies, Llc	Substrats, dispositifs et procedes de dosages cellulaires
JP4581571B2 (ja) *	2004-09-06	2010-11-17	富士ゼロックス株式会社	粒子のマレイミジル基量を測定する定量方法
RU2288463C1 (ru) *	2005-05-03	2006-11-27	Государственное образовательное учреждение высшего профессионального образования Алтайский государственный университет	Способ количественного определения малеинимида
AU2006244486A1 (en) *	2005-05-06	2006-11-16	Platypus Technologies, Llc	Liquid crystal based analyte detection
WO2007025129A2 (fr)	2005-08-25	2007-03-01	Platypus Technologies, Llc.	Compositions et cristaux liquides
US7842499B2 (en) *	2006-08-07	2010-11-30	Platypus Technologies, Llc	Substrates, devices, and methods for cellular assays
US9968935B2 (en)	2007-08-20	2018-05-15	Platypus Technologies, Llc	Devices for cell assays
US8472683B2 (en) *	2008-05-09	2013-06-25	General Electric Company	Motion correction in tomographic images
WO2010031047A2 (fr) *	2008-09-15	2010-03-18	Platypus Technologies, Llc	Détection de composés en phase vapeur par des changements de propriétés physiques d'un cristal liquide

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5110986B2 (fr) *	1972-10-05	1976-04-08
US4615986A (en) *	1979-03-05	1986-10-07	Syntex (U.S.A.) Inc.	Method for competitive protein binding assays inhibiting non-specific interference
JPS6015559A (ja) *	1983-07-06	1985-01-26	Shiraimatsu Shinyaku Kk	アポリポ蛋白−ｂの酵素免疫測定試薬
DE3516001A1 (de) *	1985-05-03	1986-11-06	Boehringer Mannheim Gmbh, 6800 Mannheim	Lipasefarbtest
US4680272A (en) *	1985-10-23	1987-07-14	University Of California	Method for detecting molecules containing amine or thiol groups

1988
- 1988-12-19 DE DE3842657A patent/DE3842657A1/de not_active Withdrawn
1989
- 1989-12-07 CS CS896935A patent/CS276659B6/cs unknown
- 1989-12-08 EP EP19890122651 patent/EP0374620A3/fr not_active Ceased
- 1989-12-18 IL IL92777A patent/IL92777A0/xx unknown
- 1989-12-18 US US07/451,708 patent/US5132226A/en not_active Expired - Fee Related
- 1989-12-19 JP JP1327483A patent/JPH02227098A/ja active Pending

Also Published As

Publication number	Publication date
EP0374620A2 (fr)	1990-06-27
DE3842657A1 (de)	1990-06-21
CS693589A3 (en)	1992-03-18
JPH02227098A (ja)	1990-09-10
IL92777A0 (en)	1990-09-17
US5132226A (en)	1992-07-21
EP0374620A3 (fr)	1991-09-18

Publication	Publication Date	Title
CS276659B6 (en)	1992-07-15	Method and means for maleic imide groups determination
US5089423A (en)	1992-02-18	Immunoassay methods and reagents and methods for producing the latter
US4492762A (en)	1985-01-08	Fluorescent polarization immunoassays
Bayer et al.	1985	3-(N-Maleimido-propionyl) biocytin: a versatile thiol-specific biotinylating reagent
EP0347138B1 (fr)	1994-09-14	Composition de liaison spécifique avec une protéine ou un hydrate de carbone de pI bas, une trousse diagnostique, et méthode d'utilisation
JP2870704B2 (ja)	1999-03-17	ホモシステインアッセイ
EP0242095A1 (fr)	1987-10-21	Marquages clivables pour l'usage dans des essais de liaisons spécifiques
US4489165A (en)	1984-12-18	Chromogenic tracers for use in an assay
EP0656005B1 (fr)	2003-04-23	Traceur, conjugues, dosages, materiels de dosage, chimioluminescents biotinyles
JP2750003B2 (ja)	1998-05-13	光活性化可能ビオチン誘導体およびイムノアッセイでの干渉を軽減させるためのその使用
CA2306752C (fr)	2008-11-18	Reactifs chimioluminescents et procedes d'analyse par chimioluminescence dans lesquels on utilise lesdits reactifs
US4880731A (en)	1989-11-14	Process and reagent for the determination of a reaction partner of an immunological reaction
DK0381450T3 (da)	1998-07-27	Assay for basisk phosphatase fra knogler.
Yang et al.	1994	Time-resolved fluorescence immunoassay with measurement of a europium chelate in solution: dissociation conditions and application for determination of cortisol
US5780243A (en)	1998-07-14	Methods for the quantitative analysis of organic compounds
Takahashi et al.	1978	Fluorometric determination of glutathione by N-(9-Acridinyl)-maleimide and its application to biological materials
EP0100543B1 (fr)	1986-10-29	Méthode pour l'analyse quantitative de composants à poids moléculaire bas contenus dans un échantillon liquide comprenant des protéines
CA1263601A (fr)	1989-12-05	Conjugat pour les immunodosages enzymatiques
US6171520B1 (en)	2001-01-09	Reagents for labeling SH groups, process for the preparation of them and method for labeling with them
CZ83393A3 (en)	1993-11-17	Process of treating humors when determining neopterin and means for carrying out said process
US11614445B2 (en)	2023-03-28	Background blockers for binding assays
US5552297A (en)	1996-09-03	Lead detection method and reggents utilizing aminolevulinic acid dehydratase and tertiary phosphines
EP0420170A2 (fr)	1991-04-03	Réactif de stabilisation pour immunoesssais sur une membrane
US5460975A (en)	1995-10-24	Diphenylmethane derivatives, process for their production and their use for the displacement of iodothyronines from proteins which bind them
JP3174729B2 (ja)	2001-06-11	アクリジン誘導体、その製法およびこれを用いた標識法