JP4318180B2 - タンパク質の飽和標識用の試薬及び方法 - Google Patents
タンパク質の飽和標識用の試薬及び方法 Download PDFInfo
- Publication number
- JP4318180B2 JP4318180B2 JP2004518895A JP2004518895A JP4318180B2 JP 4318180 B2 JP4318180 B2 JP 4318180B2 JP 2004518895 A JP2004518895 A JP 2004518895A JP 2004518895 A JP2004518895 A JP 2004518895A JP 4318180 B2 JP4318180 B2 JP 4318180B2
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- Prior art keywords
- dihydro
- dye
- dimethyl
- protein
- 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
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- 108090000623 proteins and genes Proteins 0.000 title claims abstract description 138
- 102000004169 proteins and genes Human genes 0.000 title claims abstract description 138
- 238000002372 labelling Methods 0.000 title claims abstract description 55
- 238000000034 method Methods 0.000 title claims abstract description 37
- 239000003153 chemical reaction reagent Substances 0.000 title description 8
- 239000000975 dye Substances 0.000 claims abstract description 187
- 235000018102 proteins Nutrition 0.000 claims abstract description 135
- 239000007850 fluorescent dye Substances 0.000 claims abstract description 35
- 125000005647 linker group Chemical group 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 31
- -1 6-{[2- (2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl) ethyl] amino} -6-oxohexyl Chemical group 0.000 claims description 24
- 125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 claims description 21
- 239000003638 chemical reducing agent Substances 0.000 claims description 11
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical group [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 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 description 5
- 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- PGLTVOMIXTUURA-UHFFFAOYSA-N iodoacetamide Chemical group NC(=O)CI PGLTVOMIXTUURA-UHFFFAOYSA-N 0.000 claims description 5
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 4
- 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 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 description 3
- 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
- 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 description 2
- 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
- 235000018417 cysteine Nutrition 0.000 abstract description 19
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 abstract description 18
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 5
- 235000001014 amino acid Nutrition 0.000 abstract description 3
- 150000001413 amino acids Chemical class 0.000 abstract description 3
- 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
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 163
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 56
- 239000011541 reaction mixture Substances 0.000 description 48
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 42
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 41
- 238000006243 chemical reaction Methods 0.000 description 39
- 239000007787 solid Substances 0.000 description 32
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
- 239000000523 sample Substances 0.000 description 29
- 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
- 238000003818 flash chromatography Methods 0.000 description 22
- 150000002148 esters Chemical group 0.000 description 21
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 19
- 239000012299 nitrogen atmosphere Substances 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- 239000002904 solvent Substances 0.000 description 19
- 238000003756 stirring Methods 0.000 description 19
- 239000000377 silicon dioxide Substances 0.000 description 18
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 18
- 238000010521 absorption reaction Methods 0.000 description 16
- 238000004809 thin layer chromatography Methods 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 14
- 210000004027 cell Anatomy 0.000 description 13
- 238000000539 two dimensional gel electrophoresis Methods 0.000 description 13
- 238000004458 analytical method Methods 0.000 description 12
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
- BBFHQIBCBXJITJ-UHFFFAOYSA-N 3-(2-aminoethyl)pyrrole-2,5-dione Chemical compound NCCC1=CC(=O)NC1=O BBFHQIBCBXJITJ-UHFFFAOYSA-N 0.000 description 11
- PZBFGYYEXUXCOF-UHFFFAOYSA-N TCEP Chemical compound OC(=O)CCP(CCC(O)=O)CCC(O)=O PZBFGYYEXUXCOF-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
- 239000002253 acid Substances 0.000 description 10
- 229940117389 dichlorobenzene Drugs 0.000 description 10
- 235000018977 lysine Nutrition 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 235000019198 oils Nutrition 0.000 description 10
- 238000000926 separation method Methods 0.000 description 10
- 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
- 239000004472 Lysine Substances 0.000 description 9
- 239000004202 carbamide Substances 0.000 description 9
- 125000003396 thiol group Chemical group [H]S* 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 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
- 238000001914 filtration Methods 0.000 description 8
- 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 8
- 239000006166 lysate Substances 0.000 description 7
- 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
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 238000001962 electrophoresis Methods 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 6
- 150000003573 thiols Chemical class 0.000 description 6
- 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
- ZQUVDXMUKIVNOW-UHFFFAOYSA-N n,n'-diphenylmethanimidamide Chemical compound C=1C=CC=CC=1NC=NC1=CC=CC=C1 ZQUVDXMUKIVNOW-UHFFFAOYSA-N 0.000 description 5
- 239000004576 sand Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000001502 gel electrophoresis Methods 0.000 description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- YBYRMVIVWMBXKQ-UHFFFAOYSA-N phenylmethanesulfonyl fluoride Chemical compound FS(=O)(=O)CC1=CC=CC=C1 YBYRMVIVWMBXKQ-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- VLSLTESEMMTYMX-UHFFFAOYSA-M sodium;2,3,3-trimethylindole-5-sulfonate Chemical compound [Na+].C1=C(S([O-])(=O)=O)C=C2C(C)(C)C(C)=NC2=C1 VLSLTESEMMTYMX-UHFFFAOYSA-M 0.000 description 4
- 210000001519 tissue Anatomy 0.000 description 4
- UIEGYKOJJPZRFH-UHFFFAOYSA-M 1-ethyl-2,3,3-trimethyl-5-sulfonyl-2H-indol-1-ium iodide Chemical compound [I-].C(C)[N+]=1C(C(C2=CC(C=CC=12)=S(=O)=O)(C)C)C UIEGYKOJJPZRFH-UHFFFAOYSA-M 0.000 description 3
- FLHJIAFUWHPJRT-UHFFFAOYSA-N 2,3,3-trimethylindole Chemical compound C1=CC=C2C(C)(C)C(C)=NC2=C1 FLHJIAFUWHPJRT-UHFFFAOYSA-N 0.000 description 3
- OJHGGYXHWPCLJR-UHFFFAOYSA-N 3-(3-aminopropyl)pyrrole-2,5-dione Chemical compound NCCCC1=CC(=O)NC1=O OJHGGYXHWPCLJR-UHFFFAOYSA-N 0.000 description 3
- UMCMPZBLKLEWAF-BCTGSCMUSA-N 3-[(3-cholamidopropyl)dimethylammonio]propane-1-sulfonate Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCCC[N+](C)(C)CCCS([O-])(=O)=O)C)[C@@]2(C)[C@@H](O)C1 UMCMPZBLKLEWAF-BCTGSCMUSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 125000000539 amino acid group Chemical group 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
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- 238000002264 polyacrylamide gel electrophoresis Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 3
- OEWZFQWCVFJYDD-UHFFFAOYSA-M 1,2,3,3-tetramethyl-5-sulfonyl-2H-indol-1-ium iodide Chemical compound [I-].C[N+]=1C(C(C2=CC(C=CC=12)=S(=O)=O)(C)C)C OEWZFQWCVFJYDD-UHFFFAOYSA-M 0.000 description 2
- ZLEBCFWULFVTGL-UHFFFAOYSA-N 1-(2,3,3-trimethylindol-1-ium-1-yl)butane-1-sulfonic acid;iodide Chemical compound [I-].C1=CC=C2[N+](C(CCC)S(O)(=O)=O)=C(C)C(C)(C)C2=C1 ZLEBCFWULFVTGL-UHFFFAOYSA-N 0.000 description 2
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 2
- ZBODPKUOHBXKEZ-UHFFFAOYSA-N 5-(2,3,3-trimethylindol-1-ium-1-yl)pentanoic acid;bromide Chemical compound [Br-].C1=CC=C2C(C)(C)C(C)=[N+](CCCCC(O)=O)C2=C1 ZBODPKUOHBXKEZ-UHFFFAOYSA-N 0.000 description 2
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- 125000001041 indolyl group Chemical group 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
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- 238000001906 matrix-assisted laser desorption--ionisation mass spectrometry Methods 0.000 description 2
- FLMLOZWXXPLHIE-UHFFFAOYSA-N n,n'-diphenylpropane-1,3-diimine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1N=CCC=NC1=CC=CC=C1 FLMLOZWXXPLHIE-UHFFFAOYSA-N 0.000 description 2
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- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- C07K1/13—Labelling of peptides
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- 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
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- 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
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| 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
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|---|---|
| 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 |
| US7511155B2 (en) | 2009-03-31 |
| EP1520176B1 (en) | 2010-03-10 |
| ES2341946T3 (es) | 2010-06-30 |
| 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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