ES2341946T3 - Reactivos y un metodo para el marcaje por saturacion de proteinas. - Google Patents
Reactivos y un metodo para el marcaje por saturacion de proteinas. Download PDFInfo
- Publication number
- ES2341946T3 ES2341946T3 ES02747568T ES02747568T ES2341946T3 ES 2341946 T3 ES2341946 T3 ES 2341946T3 ES 02747568 T ES02747568 T ES 02747568T ES 02747568 T ES02747568 T ES 02747568T ES 2341946 T3 ES2341946 T3 ES 2341946T3
- Authority
- ES
- Spain
- Prior art keywords
- dyes
- dihydro
- group
- chosen
- indole
- Prior art date
- 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
Links
- 108090000623 proteins and genes Proteins 0.000 title claims abstract description 139
- 102000004169 proteins and genes Human genes 0.000 title claims abstract description 138
- 238000000034 method Methods 0.000 title claims abstract description 38
- 239000003153 chemical reaction reagent Substances 0.000 title description 13
- 239000000975 dye Substances 0.000 claims abstract description 192
- 235000018102 proteins Nutrition 0.000 claims abstract description 136
- 239000007850 fluorescent dye Substances 0.000 claims abstract description 29
- 235000018417 cysteine Nutrition 0.000 claims abstract description 22
- 238000002372 labelling Methods 0.000 claims abstract description 22
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims abstract description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- -1 iodoacetamido group Chemical group 0.000 claims description 39
- 150000001875 compounds Chemical class 0.000 claims description 33
- 125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
- 239000003638 chemical reducing agent Substances 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 10
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- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- CBEPIBCXDUBBDV-UHFFFAOYSA-N CC1(C)C2=CC(S([O-])(=O)=O)=CC=C2N(CC)\C1=C\C=C\C(C(C1=CC=CC=C11)(C)C)=[N+]1CCCCCC(=O)NCCCN1C(=O)C=CC1=O Chemical compound CC1(C)C2=CC(S([O-])(=O)=O)=CC=C2N(CC)\C1=C\C=C\C(C(C1=CC=CC=C11)(C)C)=[N+]1CCCCCC(=O)NCCCN1C(=O)C=CC1=O CBEPIBCXDUBBDV-UHFFFAOYSA-N 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- YZCIACABIXJAFH-UHFFFAOYSA-N CC1(C)C2=CC(S([O-])(=O)=O)=CC=C2N(CC)\C1=C\C=C\C(C(C1=CC=CC=C11)(C)C)=[N+]1CCCCCC(=O)NCCN1C(=O)C=CC1=O Chemical compound CC1(C)C2=CC(S([O-])(=O)=O)=CC=C2N(CC)\C1=C\C=C\C(C(C1=CC=CC=C11)(C)C)=[N+]1CCCCCC(=O)NCCN1C(=O)C=CC1=O YZCIACABIXJAFH-UHFFFAOYSA-N 0.000 claims description 5
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
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- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims description 2
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- FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 claims 1
- 235000001014 amino acid Nutrition 0.000 abstract description 5
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- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical group N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 abstract 1
- 125000005647 linker group Chemical group 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 53
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- 238000006243 chemical reaction Methods 0.000 description 45
- 239000011541 reaction mixture Substances 0.000 description 41
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 38
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 37
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- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
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- 239000000377 silicon dioxide Substances 0.000 description 16
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 210000004027 cell Anatomy 0.000 description 14
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- 238000010521 absorption reaction Methods 0.000 description 13
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- 238000013508 migration Methods 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 238000004440 column chromatography Methods 0.000 description 12
- PZBFGYYEXUXCOF-UHFFFAOYSA-N TCEP Chemical compound OC(=O)CCP(CCC(O)=O)CCC(O)=O PZBFGYYEXUXCOF-UHFFFAOYSA-N 0.000 description 11
- 238000004458 analytical method Methods 0.000 description 11
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- 235000018977 lysine Nutrition 0.000 description 11
- 239000012299 nitrogen atmosphere Substances 0.000 description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 10
- BBFHQIBCBXJITJ-UHFFFAOYSA-N 3-(2-aminoethyl)pyrrole-2,5-dione Chemical compound NCCC1=CC(=O)NC1=O BBFHQIBCBXJITJ-UHFFFAOYSA-N 0.000 description 10
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 10
- 239000004472 Lysine Substances 0.000 description 10
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- 229940117389 dichlorobenzene Drugs 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
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- 238000000926 separation method Methods 0.000 description 9
- 125000003396 thiol group Chemical group [H]S* 0.000 description 9
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 8
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- VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 description 8
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- 150000003573 thiols Chemical class 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 238000004040 coloring Methods 0.000 description 6
- 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 6
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- OMYZTOJVFPVSOT-UHFFFAOYSA-N 1-ethyl-2,3,3-trimethyl-5-sulfonyl-2,4-dihydroindole Chemical compound CCN1C(C(C2=C1C=CC(=S(=O)=O)C2)(C)C)C OMYZTOJVFPVSOT-UHFFFAOYSA-N 0.000 description 5
- SHDOHVMHEAVMNK-UHFFFAOYSA-N 6-[(2e)-3,3-dimethyl-2-[(2e,4e)-5-(1,3,3-trimethylindol-1-ium-2-yl)penta-2,4-dienylidene]indol-1-yl]hexanoic acid;chloride Chemical compound [Cl-].CC1(C)C2=CC=CC=C2[N+](C)=C1\C=C\C=C\C=C\1C(C)(C)C2=CC=CC=C2N/1CCCCCC(O)=O SHDOHVMHEAVMNK-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
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- ZQUVDXMUKIVNOW-UHFFFAOYSA-N n,n'-diphenylmethanimidamide Chemical compound C=1C=CC=CC=1NC=NC1=CC=CC=C1 ZQUVDXMUKIVNOW-UHFFFAOYSA-N 0.000 description 5
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/13—Labelling of peptides
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0034—Mixtures of two or more pigments or dyes of the same type
-
- 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
- G01N33/68—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving proteins, peptides or amino acids
- G01N33/6803—General methods of protein analysis not limited to specific proteins or families of proteins
- G01N33/6806—Determination of free amino acids
- G01N33/6812—Assays for specific amino acids
- G01N33/6815—Assays for specific amino acids containing sulfur, e.g. cysteine, cystine, methionine, homocysteine
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Urology & Nephrology (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Medicinal Chemistry (AREA)
- Biophysics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Immunology (AREA)
- Physics & Mathematics (AREA)
- Biochemistry (AREA)
- Hematology (AREA)
- Analytical Chemistry (AREA)
- Bioinformatics & Computational Biology (AREA)
- Pathology (AREA)
- Cell Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- Genetics & Genomics (AREA)
- Food Science & Technology (AREA)
- General Physics & Mathematics (AREA)
- Biotechnology (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Indole Compounds (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/GB2002/003142 WO2004005933A1 (en) | 2002-07-08 | 2002-07-08 | Reagents and a method for saturation labelling of proteins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2341946T3 true ES2341946T3 (es) | 2010-06-30 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES02747568T Expired - Lifetime ES2341946T3 (es) | 2002-07-08 | 2002-07-08 | Reactivos y un metodo para el marcaje por saturacion de proteinas. |
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|---|---|
| US (1) | US7511155B2 (enExample) |
| EP (1) | EP1520176B1 (enExample) |
| JP (1) | JP4318180B2 (enExample) |
| CN (1) | CN1307263C (enExample) |
| AT (1) | ATE460670T1 (enExample) |
| AU (1) | AU2002317958B2 (enExample) |
| CA (1) | CA2491692C (enExample) |
| DE (1) | DE60235652D1 (enExample) |
| ES (1) | ES2341946T3 (enExample) |
| WO (1) | WO2004005933A1 (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006062222A1 (ja) * | 2004-12-06 | 2006-06-15 | National Institute Of Advanced Industrial Science And Technology | タンパク質の分離方法及び染色方法、並びにこれらの方法に用いるタンパク質染色液及びタンパク質染色用キット |
| US20110186434A1 (en) * | 2008-07-23 | 2011-08-04 | Leibniz Institute of Plant Biochemistry | Qualitative and/or quantitative determination of a proteinaceous molecule in a plurality of samples |
| US20110226622A1 (en) * | 2008-12-02 | 2011-09-22 | Japan Science And Technology Agency | Novel clear native electrophoresis method utilizing aromatic sulfonic acid compound |
| KR101149535B1 (ko) | 2009-04-17 | 2012-05-25 | 한국과학기술연구원 | 생체 분자 표지를 위한 신규 시아닌 화합물 및 그 제조방법 |
| US20130295613A1 (en) * | 2010-12-28 | 2013-11-07 | Chugai Seiyaku Kabushiki Kaisha | Animal cell culturing method |
| CN103113282A (zh) * | 2013-01-22 | 2013-05-22 | 天津理工大学 | 一种含吸电子基团半菁蓝素温敏分子光学探针的制备方法 |
| CN103113283A (zh) * | 2013-01-22 | 2013-05-22 | 天津理工大学 | 一种含给电子基团半菁蓝素温敏分子光学探针的制备方法 |
| DE102022131445A1 (de) * | 2022-11-28 | 2024-05-29 | Carl Zeiss Microscopy Gmbh | Verfahren und Vorrichtung zum Aufbereiten von Daten zum Identifizieren von Analyten |
| DE102022131447A1 (de) * | 2022-11-28 | 2024-05-29 | Carl Zeiss Microscopy Gmbh | Verfahren und Vorrichtung zum Aufbereiten von Daten zum Identifizieren von Analyten |
| DE102022131448A1 (de) * | 2022-11-28 | 2024-05-29 | Carl Zeiss Microscopy Gmbh | Verfahren und Vorrichtung zum Aufbereiten von Daten zum Identifizieren von Analyten |
| DE102022131449A1 (de) * | 2022-11-28 | 2024-05-29 | Carl Zeiss Microscopy Gmbh | Verfahren und Vorrichtung zum Aufbereiten von Daten zum Identifizieren von Analyten |
| DE102022131450A1 (de) * | 2022-11-28 | 2024-05-29 | Carl Zeiss Microscopy Gmbh | Verfahren und Vorrichtung zum Aufbereiten von Daten zum Identifizieren von Analyten |
| DE102022131444A1 (de) * | 2022-11-28 | 2024-05-29 | Carl Zeiss Microscopy Gmbh | Verfahren zum Identifizieren von Analyten in einer Bildfolge |
| DE102022131451A1 (de) * | 2022-11-28 | 2024-05-29 | Carl Zeiss Microscopy Gmbh | Verfahren und Vorrichtung zum Bestimmen einer Signal-Zusammensetzung von Signalfolgen einer Bildfolge |
| DE102022131446A1 (de) * | 2022-11-28 | 2024-05-29 | Carl Zeiss Microscopy Gmbh | Verfahren und Vorrichtung zum Aufbereiten von Daten zum Identifizieren von Analyten |
| DE102023122213A1 (de) * | 2023-08-18 | 2025-02-20 | Carl Zeiss Microscopy Gmbh | Verfahren zum Bereitstellen von Quelldaten zum Trainieren oder Validieren eines Verarbeitungsmodells zum Verarbeiten von Analyt-Bildfolgen |
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|---|---|---|---|---|
| US5268486A (en) * | 1986-04-18 | 1993-12-07 | Carnegie-Mellon Unversity | Method for labeling and detecting materials employing arylsulfonate cyanine dyes |
| US6127134A (en) * | 1995-04-20 | 2000-10-03 | Carnegie Mellon University | Difference gel electrophoresis using matched multiple dyes |
| BR9814816A (pt) * | 1997-10-10 | 2004-06-22 | Cytovia Inc | Novas moléculas repórter fluorescentes e suas aplicações incluindo análises de caspases |
| DE60010956T2 (de) * | 1999-03-25 | 2005-06-16 | Nisshinbo Industries, Inc. | Carbodiimidverbindungen, die eine fluoreszierende Gruppe enthalten, deren Vorstufen und Verfahren zu deren Herstellung |
| US6114350A (en) * | 1999-04-19 | 2000-09-05 | Nen Life Science Products, Inc. | Cyanine dyes and synthesis methods thereof |
| WO2002026891A1 (en) * | 2000-09-29 | 2002-04-04 | Molecular Probes, Inc. | Modified carbocyanine dyes and their conjugates |
| JP2003048879A (ja) * | 2001-05-31 | 2003-02-21 | Nisshinbo Ind Inc | 蛍光性基含有カルボジイミド化合物及び該化合物の製造方法 |
| US8227621B2 (en) * | 2005-06-30 | 2012-07-24 | Li-Cor, Inc. | Cyanine dyes and methods of use |
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2002
- 2002-07-08 CN CNB02829498XA patent/CN1307263C/zh not_active Expired - Lifetime
- 2002-07-08 AT AT02747568T patent/ATE460670T1/de not_active IP Right Cessation
- 2002-07-08 US US10/519,433 patent/US7511155B2/en not_active Expired - Lifetime
- 2002-07-08 JP JP2004518895A patent/JP4318180B2/ja not_active Expired - Lifetime
- 2002-07-08 AU AU2002317958A patent/AU2002317958B2/en not_active Expired
- 2002-07-08 EP EP02747568A patent/EP1520176B1/en not_active Expired - Lifetime
- 2002-07-08 ES ES02747568T patent/ES2341946T3/es not_active Expired - Lifetime
- 2002-07-08 CA CA2491692A patent/CA2491692C/en not_active Expired - Lifetime
- 2002-07-08 WO PCT/GB2002/003142 patent/WO2004005933A1/en not_active Ceased
- 2002-07-08 DE DE60235652T patent/DE60235652D1/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA2491692A1 (en) | 2004-01-15 |
| CN1650168A (zh) | 2005-08-03 |
| AU2002317958B2 (en) | 2007-07-12 |
| ATE460670T1 (de) | 2010-03-15 |
| EP1520176A1 (en) | 2005-04-06 |
| WO2004005933A1 (en) | 2004-01-15 |
| JP4318180B2 (ja) | 2009-08-19 |
| US7511155B2 (en) | 2009-03-31 |
| EP1520176B1 (en) | 2010-03-10 |
| AU2002317958A1 (en) | 2004-01-23 |
| CA2491692C (en) | 2010-12-07 |
| DE60235652D1 (de) | 2010-04-22 |
| US20050233462A1 (en) | 2005-10-20 |
| CN1307263C (zh) | 2007-03-28 |
| JP2005532543A (ja) | 2005-10-27 |
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