CA2491692C - Reagents and a method for saturation labelling of proteins - Google Patents
Reagents and a method for saturation labelling of proteins Download PDFInfo
- Publication number
- CA2491692C CA2491692C CA2491692A CA2491692A CA2491692C CA 2491692 C CA2491692 C CA 2491692C CA 2491692 A CA2491692 A CA 2491692A CA 2491692 A CA2491692 A CA 2491692A CA 2491692 C CA2491692 C CA 2491692C
- Authority
- CA
- Canada
- Prior art keywords
- dye
- dihydro
- dimethyl
- group
- ethyl
- 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 140
- 102000004169 proteins and genes Human genes 0.000 title claims abstract description 139
- 238000002372 labelling Methods 0.000 title claims abstract description 58
- 238000000034 method Methods 0.000 title claims abstract description 40
- 239000003153 chemical reaction reagent Substances 0.000 title description 9
- 239000000975 dye Substances 0.000 claims abstract description 201
- 235000018102 proteins Nutrition 0.000 claims abstract description 136
- 239000007850 fluorescent dye Substances 0.000 claims abstract description 37
- 125000005647 linker group Chemical group 0.000 claims abstract description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims abstract description 11
- 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 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 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
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 4
- 150000001875 compounds Chemical class 0.000 claims description 32
- 125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 claims description 22
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 claims description 20
- 239000003638 chemical reducing agent Substances 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- -1 iodoacetamido group Chemical group 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims description 5
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 4
- 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 3
- 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 2
- SOPHKGJHIXGYRN-UHFFFAOYSA-N CCCC(N1C2=CC=CC=C2C(C)(C)/C\1=C\C=C\C1=[N+](CCCCCC(NCCCN(C(C=C2)=O)C2=O)=O)C2=CC=CC=C2C1(C)C)S([O-])(=O)=O Chemical compound CCCC(N1C2=CC=CC=C2C(C)(C)/C\1=C\C=C\C1=[N+](CCCCCC(NCCCN(C(C=C2)=O)C2=O)=O)C2=CC=CC=C2C1(C)C)S([O-])(=O)=O SOPHKGJHIXGYRN-UHFFFAOYSA-N 0.000 claims 2
- LQTBNHOBNNVRAN-UHFFFAOYSA-N CCCC(N1C2=CC=CC=C2C(C)(C)/C\1=C\C=C\C1=[N+](CCCCCC(NCCN(C(C=C2)=O)C2=O)=O)C2=CC=CC=C2C1(C)C)S([O-])(=O)=O Chemical compound CCCC(N1C2=CC=CC=C2C(C)(C)/C\1=C\C=C\C1=[N+](CCCCCC(NCCN(C(C=C2)=O)C2=O)=O)C2=CC=CC=C2C1(C)C)S([O-])(=O)=O LQTBNHOBNNVRAN-UHFFFAOYSA-N 0.000 claims 2
- FCSXRQTZLPYGNV-UHFFFAOYSA-N (2E)-2-[(E)-3-[1-[6-[2-(2,5-dioxopyrrol-1-yl)ethylamino]-6-oxohexyl]-3,3-dimethylindol-1-ium-2-yl]prop-2-enylidene]-3,3-dimethyl-1-propylindole-5-sulfonate Chemical compound CC1(C)C2=CC(S([O-])(=O)=O)=CC=C2N(CCC)\C1=C\C=C\C(C(C1=CC=CC=C11)(C)C)=[N+]1CCCCCC(=O)NCCN1C(=O)C=CC1=O FCSXRQTZLPYGNV-UHFFFAOYSA-N 0.000 claims 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims 1
- 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
- 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 1
- FAKZUFOWWUSQAZ-UHFFFAOYSA-N CC1(C)C2=CC=CC=C2[N+](CCCCCC(NCCN(C(C=C2)=O)C2=O)=O)=C1/C=C/C=C/C=C(\C(C)(C)C1=C2)/N(C)C1=CC=C2S([O-])(=O)=O Chemical compound CC1(C)C2=CC=CC=C2[N+](CCCCCC(NCCN(C(C=C2)=O)C2=O)=O)=C1/C=C/C=C/C=C(\C(C)(C)C1=C2)/N(C)C1=CC=C2S([O-])(=O)=O FAKZUFOWWUSQAZ-UHFFFAOYSA-N 0.000 claims 1
- PIRSUKXOIHUGRK-UHFFFAOYSA-N CCCC(N1C2=CC=CC=C2C(C)(C)/C\1=C\C=C\C=C\C1=[N+](CCCCCC(NCCN(C(C=C2)=O)C2=O)=O)C2=CC=CC=C2C1(C)C)S([O-])(=O)=O Chemical compound CCCC(N1C2=CC=CC=C2C(C)(C)/C\1=C\C=C\C=C\C1=[N+](CCCCCC(NCCN(C(C=C2)=O)C2=O)=O)C2=CC=CC=C2C1(C)C)S([O-])(=O)=O PIRSUKXOIHUGRK-UHFFFAOYSA-N 0.000 claims 1
- 235000018417 cysteine Nutrition 0.000 abstract description 17
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 abstract description 16
- 235000001014 amino acid Nutrition 0.000 abstract description 3
- 150000001413 amino acids Chemical class 0.000 abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 162
- 238000006243 chemical reaction Methods 0.000 description 85
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 56
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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 40
- 239000007787 solid Substances 0.000 description 33
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 27
- 239000000047 product Substances 0.000 description 25
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 24
- 239000000523 sample Substances 0.000 description 23
- 238000003818 flash chromatography Methods 0.000 description 22
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 21
- 150000002148 esters Chemical group 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 19
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
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- BBFHQIBCBXJITJ-UHFFFAOYSA-N 3-(2-aminoethyl)pyrrole-2,5-dione Chemical compound NCCC1=CC(=O)NC1=O BBFHQIBCBXJITJ-UHFFFAOYSA-N 0.000 description 10
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- 229940117389 dichlorobenzene Drugs 0.000 description 10
- 235000018977 lysine Nutrition 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- 241000588724 Escherichia coli Species 0.000 description 9
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 9
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- 230000000694 effects Effects 0.000 description 9
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- 125000003396 thiol group Chemical group [H]S* 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 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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- YUUDHAOMIPLRQU-UHFFFAOYSA-N 6-(2,3,3-trimethylindol-1-ium-1-yl)hexanoic acid;bromide Chemical compound [Br-].C1=CC=C2C(C)(C)C(C)=[N+](CCCCCC(O)=O)C2=C1 YUUDHAOMIPLRQU-UHFFFAOYSA-N 0.000 description 6
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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)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Analytical Chemistry (AREA)
- Physics & Mathematics (AREA)
- Biomedical Technology (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Hematology (AREA)
- Immunology (AREA)
- Biophysics (AREA)
- Urology & Nephrology (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- Cell Biology (AREA)
- Biotechnology (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Computational Biology (AREA)
- Food Science & Technology (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Plural Heterocyclic Compounds (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (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 (2)
| Publication Number | Publication Date |
|---|---|
| CA2491692A1 CA2491692A1 (en) | 2004-01-15 |
| CA2491692C true CA2491692C (en) | 2010-12-07 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2491692A Expired - Lifetime CA2491692C (en) | 2002-07-08 | 2002-07-08 | Reagents and a method for saturation labelling of proteins |
Country Status (10)
| Country | Link |
|---|---|
| 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 |
|---|---|---|---|---|
| DE112005003114T5 (de) * | 2004-12-06 | 2008-05-08 | Katayanagi Institute, Hachioji | Verfahren zum Trennen von Protein, Verfahren zum Färben von Protein und flüssiges Proteinfärbemittel sowie Proteinfärbekit zur Verwendung bei diesen Verfahren |
| 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 |
| JP5213967B2 (ja) * | 2008-12-02 | 2013-06-19 | 独立行政法人科学技術振興機構 | 芳香族スルホン酸化合物を用いた新規ＣｌｅａｒＮａｔｉｖｅ電気泳動法 |
| US8729276B2 (en) | 2009-04-17 | 2014-05-20 | Korea Institute Of Science And Technology | Cyanine compound for labeling biomolecule and preparation method thereof |
| SG191371A1 (en) * | 2010-12-28 | 2013-08-30 | Chugai Pharmaceutical Co Ltd | Animal cell culturing method |
| 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 |
| 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 |
| 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 |
| DE102022131446A1 (de) * | 2022-11-28 | 2024-05-29 | Carl Zeiss Microscopy Gmbh | Verfahren und Vorrichtung zum Aufbereiten von Daten zum Identifizieren von Analyten |
| DE102022131445A1 (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 |
| DE102022131451A1 (de) * | 2022-11-28 | 2024-05-29 | Carl Zeiss Microscopy Gmbh | Verfahren und Vorrichtung zum Bestimmen einer Signal-Zusammensetzung von Signalfolgen einer Bildfolge |
| 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 |
| 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 |
Family Cites Families (8)
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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 |
| EP1038938B1 (en) * | 1999-03-25 | 2004-05-26 | Nisshinbo Industries, Inc. | Fluorescent group containing carbodiimides, their precursors and methods for their production |
| US6114350A (en) * | 1999-04-19 | 2000-09-05 | Nen Life Science Products, Inc. | Cyanine dyes and synthesis methods thereof |
| AU2001294859A1 (en) * | 2000-09-29 | 2002-04-08 | 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 |
-
2002
- 2002-07-08 EP EP02747568A patent/EP1520176B1/en not_active Expired - Lifetime
- 2002-07-08 US US10/519,433 patent/US7511155B2/en not_active Expired - Lifetime
- 2002-07-08 AT AT02747568T patent/ATE460670T1/de not_active IP Right Cessation
- 2002-07-08 CA CA2491692A patent/CA2491692C/en not_active Expired - Lifetime
- 2002-07-08 CN CNB02829498XA patent/CN1307263C/zh not_active Expired - Lifetime
- 2002-07-08 AU AU2002317958A patent/AU2002317958B2/en not_active Expired
- 2002-07-08 DE DE60235652T patent/DE60235652D1/de not_active Expired - Lifetime
- 2002-07-08 JP JP2004518895A patent/JP4318180B2/ja not_active Expired - Lifetime
- 2002-07-08 ES ES02747568T patent/ES2341946T3/es not_active Expired - Lifetime
- 2002-07-08 WO PCT/GB2002/003142 patent/WO2004005933A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| EP1520176A1 (en) | 2005-04-06 |
| ATE460670T1 (de) | 2010-03-15 |
| DE60235652D1 (de) | 2010-04-22 |
| CN1650168A (zh) | 2005-08-03 |
| AU2002317958A1 (en) | 2004-01-23 |
| CA2491692A1 (en) | 2004-01-15 |
| CN1307263C (zh) | 2007-03-28 |
| US20050233462A1 (en) | 2005-10-20 |
| US7511155B2 (en) | 2009-03-31 |
| ES2341946T3 (es) | 2010-06-30 |
| AU2002317958B2 (en) | 2007-07-12 |
| EP1520176B1 (en) | 2010-03-10 |
| JP4318180B2 (ja) | 2009-08-19 |
| JP2005532543A (ja) | 2005-10-27 |
| WO2004005933A1 (en) | 2004-01-15 |
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