JP5133236B2 - 生物学的材料を分離するためのアントラキノン染料リガンドを含む吸着剤 - Google Patents
生物学的材料を分離するためのアントラキノン染料リガンドを含む吸着剤 Download PDFInfo
- Publication number
- JP5133236B2 JP5133236B2 JP2008504742A JP2008504742A JP5133236B2 JP 5133236 B2 JP5133236 B2 JP 5133236B2 JP 2008504742 A JP2008504742 A JP 2008504742A JP 2008504742 A JP2008504742 A JP 2008504742A JP 5133236 B2 JP5133236 B2 JP 5133236B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- unsubstituted
- sulfo
- substituted
- 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 - Fee Related
Links
- 239000003463 adsorbent Substances 0.000 title claims abstract description 58
- 239000012620 biological material Substances 0.000 title claims abstract description 12
- 239000003446 ligand Substances 0.000 title abstract description 35
- 239000001000 anthraquinone dye Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 46
- 238000000034 method Methods 0.000 claims abstract description 22
- 239000000758 substrate Substances 0.000 claims abstract description 20
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 5
- -1 methylene-phenylene-methylene group Chemical group 0.000 claims description 67
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 36
- 102000004169 proteins and genes Human genes 0.000 claims description 30
- 108090000623 proteins and genes Proteins 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical group 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 102000004190 Enzymes Human genes 0.000 claims description 14
- 108090000790 Enzymes Proteins 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 14
- 150000001720 carbohydrates Chemical class 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 11
- 229920002554 vinyl polymer Polymers 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 125000001570 methylene group Chemical class [H]C([H])([*:1])[*:2] 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 7
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 5
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 claims description 4
- 229920001184 polypeptide Polymers 0.000 claims description 4
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 238000001042 affinity chromatography Methods 0.000 abstract description 13
- 238000000926 separation method Methods 0.000 abstract description 9
- 238000006243 chemical reaction Methods 0.000 abstract description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 56
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 47
- 239000000243 solution Substances 0.000 description 35
- 239000000975 dye Substances 0.000 description 30
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 28
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 16
- 229920000936 Agarose Polymers 0.000 description 15
- 239000001257 hydrogen Substances 0.000 description 15
- 229910052739 hydrogen Inorganic materials 0.000 description 15
- 239000011159 matrix material Substances 0.000 description 15
- 239000000872 buffer Substances 0.000 description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- 239000011780 sodium chloride Substances 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- 229940088598 enzyme Drugs 0.000 description 12
- 239000000835 fiber Substances 0.000 description 12
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 238000000746 purification Methods 0.000 description 10
- 230000027455 binding Effects 0.000 description 9
- 238000009739 binding Methods 0.000 description 9
- 229920000768 polyamine Polymers 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 238000005119 centrifugation Methods 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 238000010828 elution Methods 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 239000000499 gel Substances 0.000 description 8
- 230000003993 interaction Effects 0.000 description 8
- 230000007935 neutral effect Effects 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 125000006850 spacer group Chemical group 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- KIRKGWILHWJIMS-UHFFFAOYSA-K trisodium;1-amino-4-[4-[[4-chloro-6-(2-sulfonatoanilino)-1,3,5-triazin-2-yl]amino]-3-sulfonatoanilino]-9,10-dioxoanthracene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C(S([O-])(=O)=O)C=C1NC(C=C1S([O-])(=O)=O)=CC=C1NC(N=1)=NC(Cl)=NC=1NC1=CC=CC=C1S([O-])(=O)=O KIRKGWILHWJIMS-UHFFFAOYSA-K 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 108010029541 Laccase Proteins 0.000 description 6
- 235000014633 carbohydrates Nutrition 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- 238000011534 incubation Methods 0.000 description 6
- YBYRMVIVWMBXKQ-UHFFFAOYSA-N phenylmethanesulfonyl fluoride Chemical compound FS(=O)(=O)CC1=CC=CC=C1 YBYRMVIVWMBXKQ-UHFFFAOYSA-N 0.000 description 6
- 239000008363 phosphate buffer Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 102000004452 Arginase Human genes 0.000 description 5
- 108700024123 Arginases Proteins 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 5
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 5
- 235000011130 ammonium sulphate Nutrition 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 5
- 238000001742 protein purification Methods 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- 241001465318 Aspergillus terreus Species 0.000 description 4
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- 241000233866 Fungi Species 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- 229920002684 Sepharose Polymers 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 238000002835 absorbance Methods 0.000 description 4
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 4
- 239000011543 agarose gel Substances 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000003556 assay Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 239000007857 degradation product Substances 0.000 description 4
- PGXWDLGWMQIXDT-UHFFFAOYSA-N methylsulfinylmethane;hydrate Chemical compound O.CS(C)=O PGXWDLGWMQIXDT-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 4
- 239000000985 reactive dye Substances 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- JDIIGWSSTNUWGK-UHFFFAOYSA-N 1h-imidazol-3-ium;chloride Chemical compound [Cl-].[NH2+]1C=CN=C1 JDIIGWSSTNUWGK-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 241000228245 Aspergillus niger Species 0.000 description 3
- 101710088194 Dehydrogenase Proteins 0.000 description 3
- 229920002307 Dextran Polymers 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000000732 arylene group Chemical group 0.000 description 3
- 125000004956 cyclohexylene group Chemical group 0.000 description 3
- 239000008121 dextrose Substances 0.000 description 3
- 238000004043 dyeing Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000011536 extraction buffer Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000012216 screening Methods 0.000 description 3
- 238000012289 standard assay Methods 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 2
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 2
- 102000009027 Albumins Human genes 0.000 description 2
- 108010088751 Albumins Proteins 0.000 description 2
- 108010017384 Blood Proteins Proteins 0.000 description 2
- 102000004506 Blood Proteins Human genes 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- VNMGVBPCESRCOG-UHFFFAOYSA-N OC(=O)ClS(O)(=O)=O Chemical group OC(=O)ClS(O)(=O)=O VNMGVBPCESRCOG-UHFFFAOYSA-N 0.000 description 2
- 101800004937 Protein C Proteins 0.000 description 2
- 102000017975 Protein C Human genes 0.000 description 2
- 239000005700 Putrescine Substances 0.000 description 2
- 101800001700 Saposin-D Proteins 0.000 description 2
- 229920005654 Sephadex Polymers 0.000 description 2
- 239000012507 Sephadex™ Substances 0.000 description 2
- 102000012479 Serine Proteases Human genes 0.000 description 2
- 108010022999 Serine Proteases Proteins 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 102000004142 Trypsin Human genes 0.000 description 2
- 108090000631 Trypsin Proteins 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 125000002015 acyclic group Chemical group 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- OHDRQQURAXLVGJ-HLVWOLMTSA-N azane;(2e)-3-ethyl-2-[(e)-(3-ethyl-6-sulfo-1,3-benzothiazol-2-ylidene)hydrazinylidene]-1,3-benzothiazole-6-sulfonic acid Chemical compound [NH4+].[NH4+].S/1C2=CC(S([O-])(=O)=O)=CC=C2N(CC)C\1=N/N=C1/SC2=CC(S([O-])(=O)=O)=CC=C2N1CC OHDRQQURAXLVGJ-HLVWOLMTSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 238000013375 chromatographic separation Methods 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 125000002993 cycloalkylene group Chemical group 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 238000000502 dialysis Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229920000307 polymer substrate Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 229960000856 protein c Drugs 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000012086 standard solution Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 239000012588 trypsin Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XBTRYWRVOBZSGM-UHFFFAOYSA-N (4-methylphenyl)methanediamine Chemical class CC1=CC=C(C(N)N)C=C1 XBTRYWRVOBZSGM-UHFFFAOYSA-N 0.000 description 1
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- SGMXQYKVIAEVKN-UHFFFAOYSA-N 1-n'-(2-aminoethyl)ethane-1,1-diamine Chemical compound CC(N)NCCN SGMXQYKVIAEVKN-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical compound NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- ROFCYGFJWHTQIY-UHFFFAOYSA-N 2-methylbenzene-1,3,5-triamine;trihydrochloride Chemical compound Cl.Cl.Cl.CC1=C(N)C=C(N)C=C1N ROFCYGFJWHTQIY-UHFFFAOYSA-N 0.000 description 1
- KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 description 1
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical class C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- 102100031126 6-phosphogluconolactonase Human genes 0.000 description 1
- 108010029731 6-phosphogluconolactonase Proteins 0.000 description 1
- 102000007698 Alcohol dehydrogenase Human genes 0.000 description 1
- 108010021809 Alcohol dehydrogenase Proteins 0.000 description 1
- 108090000935 Antithrombin III Proteins 0.000 description 1
- 102000004411 Antithrombin III Human genes 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- LKXXYYAQRFNGTN-UHFFFAOYSA-N CC1(C(S(O)(=O)=O)=CC(Nc(c(C(c2c3cccc2)=O)c2C3=O)cc(S(O)(=O)=O)c2N)=CC1)Nc1nc(N2CCOCC2)nc(Cl)n1 Chemical compound CC1(C(S(O)(=O)=O)=CC(Nc(c(C(c2c3cccc2)=O)c2C3=O)cc(S(O)(=O)=O)c2N)=CC1)Nc1nc(N2CCOCC2)nc(Cl)n1 LKXXYYAQRFNGTN-UHFFFAOYSA-N 0.000 description 1
- 0 Cc(c(Nc1nc(Cl)nc(NC(C=C2)=CC=C*2S(O)(=O)=O)n1)c(C)c(S(O)(=O)=O)c1C)c1Nc(c(C(c1c2cccc1)=O)c1C2=O)cc(S(O)(=O)=O)c1N Chemical compound Cc(c(Nc1nc(Cl)nc(NC(C=C2)=CC=C*2S(O)(=O)=O)n1)c(C)c(S(O)(=O)=O)c1C)c1Nc(c(C(c1c2cccc1)=O)c1C2=O)cc(S(O)(=O)=O)c1N 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- 102100022641 Coagulation factor IX Human genes 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 102000052510 DNA-Binding Proteins Human genes 0.000 description 1
- 108700020911 DNA-Binding Proteins Proteins 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 108010076282 Factor IX Proteins 0.000 description 1
- 108010054218 Factor VIII Proteins 0.000 description 1
- 102000001690 Factor VIII Human genes 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 108010018962 Glucosephosphate Dehydrogenase Proteins 0.000 description 1
- 102000057621 Glycerol kinases Human genes 0.000 description 1
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
- 102000005548 Hexokinase Human genes 0.000 description 1
- 108700040460 Hexokinases Proteins 0.000 description 1
- 102000004157 Hydrolases Human genes 0.000 description 1
- 108090000604 Hydrolases Proteins 0.000 description 1
- 102000003855 L-lactate dehydrogenase Human genes 0.000 description 1
- 108700023483 L-lactate dehydrogenases Proteins 0.000 description 1
- 102000003960 Ligases Human genes 0.000 description 1
- 108090000364 Ligases Proteins 0.000 description 1
- 241001024304 Mino Species 0.000 description 1
- 101710163270 Nuclease Proteins 0.000 description 1
- 108090000854 Oxidoreductases Proteins 0.000 description 1
- 102000004316 Oxidoreductases Human genes 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 102000045595 Phosphoprotein Phosphatases Human genes 0.000 description 1
- 108700019535 Phosphoprotein Phosphatases Proteins 0.000 description 1
- 108091000080 Phosphotransferase Proteins 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 101710163410 Probable glycerol kinase Proteins 0.000 description 1
- 102000044126 RNA-Binding Proteins Human genes 0.000 description 1
- 108700020471 RNA-Binding Proteins Proteins 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- NSDSIQGBHACTLY-UHFFFAOYSA-N Reactive Blue 5 Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C(S(O)(=O)=O)C=C1NC(C=1)=CC=C(S(O)(=O)=O)C=1NC(N=1)=NC(Cl)=NC=1NC1=CC=CC(S(O)(=O)=O)=C1 NSDSIQGBHACTLY-UHFFFAOYSA-N 0.000 description 1
- 102000006382 Ribonucleases Human genes 0.000 description 1
- 108010083644 Ribonucleases Proteins 0.000 description 1
- 102000003990 Urokinase-type plasminogen activator Human genes 0.000 description 1
- 108090000435 Urokinase-type plasminogen activator Proteins 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 1
- 229960005348 antithrombin iii Drugs 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 229960000074 biopharmaceutical Drugs 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000000368 destabilizing effect Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 229960004222 factor ix Drugs 0.000 description 1
- 229960000301 factor viii Drugs 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229960002897 heparin Drugs 0.000 description 1
- 229920000669 heparin Polymers 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 230000003278 mimic effect Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- KMBPCQSCMCEPMU-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-methylpropane-1,3-diamine Chemical compound NCCCN(C)CCCN KMBPCQSCMCEPMU-UHFFFAOYSA-N 0.000 description 1
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 1
- QHJABUZHRJTCAR-UHFFFAOYSA-N n'-methylpropane-1,3-diamine Chemical compound CNCCCN QHJABUZHRJTCAR-UHFFFAOYSA-N 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- NADBWXCIVAJJQS-UHFFFAOYSA-N naphthalene-1,3,6-triamine Chemical compound NC1=CC(N)=CC2=CC(N)=CC=C21 NADBWXCIVAJJQS-UHFFFAOYSA-N 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 238000001426 native polyacrylamide gel electrophoresis Methods 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- DYFXGORUJGZJCA-UHFFFAOYSA-N phenylmethanediamine Chemical compound NC(N)C1=CC=CC=C1 DYFXGORUJGZJCA-UHFFFAOYSA-N 0.000 description 1
- 102000020233 phosphotransferase Human genes 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 238000002264 polyacrylamide gel electrophoresis Methods 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 108091033319 polynucleotide Proteins 0.000 description 1
- 102000040430 polynucleotide Human genes 0.000 description 1
- 239000002157 polynucleotide Substances 0.000 description 1
- 239000005373 porous glass Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 235000019833 protease Nutrition 0.000 description 1
- 239000011546 protein dye Substances 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 108091008146 restriction endonucleases Proteins 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- ZUCXUTRTSQLRCV-UHFFFAOYSA-K trisodium;1-amino-4-[3-[[4-chloro-6-(3-sulfonatoanilino)-1,3,5-triazin-2-yl]amino]-2,4,6-trimethyl-5-sulfonatoanilino]-9,10-dioxoanthracene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].CC1=C(S([O-])(=O)=O)C(C)=C(NC=2C=3C(=O)C4=CC=CC=C4C(=O)C=3C(N)=C(C=2)S([O-])(=O)=O)C(C)=C1NC(N=1)=NC(Cl)=NC=1NC1=CC=CC(S([O-])(=O)=O)=C1 ZUCXUTRTSQLRCV-UHFFFAOYSA-K 0.000 description 1
- VZPXDCIISFTYOM-UHFFFAOYSA-K trisodium;1-amino-4-[4-[[4-chloro-6-(3-sulfonatoanilino)-1,3,5-triazin-2-yl]amino]-3-sulfonatoanilino]-9,10-dioxoanthracene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C(S([O-])(=O)=O)C=C1NC(C=C1S([O-])(=O)=O)=CC=C1NC(N=1)=NC(Cl)=NC=1NC1=CC=CC(S([O-])(=O)=O)=C1 VZPXDCIISFTYOM-UHFFFAOYSA-K 0.000 description 1
- 229960005356 urokinase Drugs 0.000 description 1
- 108010047303 von Willebrand Factor Proteins 0.000 description 1
- 102100036537 von Willebrand factor Human genes 0.000 description 1
- 229960001134 von willebrand factor Drugs 0.000 description 1
Images
Classifications
-
- 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
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
- C09B69/101—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing an anthracene dye
-
- 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
- C09B62/06—Anthracene dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Compounds Of Unknown Constitution (AREA)
- Pyrane Compounds (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP05102776 | 2005-04-08 | ||
| EP05102776.1 | 2005-04-08 | ||
| PCT/EP2006/061121 WO2006108760A2 (en) | 2005-04-08 | 2006-03-29 | Adsorbents comprising anthraquinone dye-ligands for the separation of biological materials |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008539280A JP2008539280A (ja) | 2008-11-13 |
| JP2008539280A5 JP2008539280A5 (enExample) | 2012-08-30 |
| JP5133236B2 true JP5133236B2 (ja) | 2013-01-30 |
Family
ID=34939196
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008504742A Expired - Fee Related JP5133236B2 (ja) | 2005-04-08 | 2006-03-29 | 生物学的材料を分離するためのアントラキノン染料リガンドを含む吸着剤 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US8227599B2 (enExample) |
| EP (1) | EP1866379B1 (enExample) |
| JP (1) | JP5133236B2 (enExample) |
| AT (1) | ATE509989T1 (enExample) |
| DK (1) | DK1866379T3 (enExample) |
| ES (1) | ES2366796T3 (enExample) |
| MY (1) | MY144344A (enExample) |
| PL (1) | PL1866379T3 (enExample) |
| PT (1) | PT1866379E (enExample) |
| SI (1) | SI1866379T1 (enExample) |
| TW (1) | TWI415663B (enExample) |
| WO (1) | WO2006108760A2 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7550910B2 (en) * | 2005-11-08 | 2009-06-23 | General Electric Company | Fluorescent lamp with barrier layer containing pigment particles |
| EP1967513A1 (en) * | 2007-03-08 | 2008-09-10 | Rheinische Friedrich-Wilhelms-Universität Bonn | Novel P2Y12 receptor antagonists |
| KR101471457B1 (ko) * | 2012-11-27 | 2014-12-10 | (주)경인양행 | 반응성 청색 염료 조성물 및 이를 이용한 섬유의 염색방법 |
| KR101621930B1 (ko) | 2013-10-31 | 2016-05-17 | (주)바이오액츠 | 생체분자 표지를 위한 소광 염료 및 그 제조방법 |
| JP2017512131A (ja) * | 2014-02-04 | 2017-05-18 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | 特異的アントラキノン染料リガンド構造の使用による抗体、抗体断片又はそれらの操作された変異体の精製方法 |
| EP2918641A1 (en) | 2014-03-13 | 2015-09-16 | Basf Se | Method for purification of antibodies, antibody fragments or engineered variants thereof using specific anthraquinone dye-ligand structures |
| CN117696019A (zh) * | 2024-01-08 | 2024-03-15 | 中国科学院赣江创新研究院 | 植物纤维基吸附材料及其制备方法与应用 |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1644616A1 (de) * | 1967-06-02 | 1970-12-17 | Bayer Ag | Anthrachinon-Reaktivfarbstoffe |
| US3758467A (en) * | 1971-08-11 | 1973-09-11 | Ciba Geigy Ag | Anthraquinone dyestuffs |
| DE2443119A1 (de) * | 1973-09-10 | 1975-03-13 | Research Corp | Selektive entfernung von albumin aus blutfluessigkeiten sowie substanzen zur durchfuehrung des verfahrens |
| US4016149A (en) | 1973-09-10 | 1977-04-05 | Research Corporation | Selective removal of albumin from blood fluid and compositions therefore |
| DE2652119C3 (de) * | 1976-11-16 | 1980-07-17 | Bayer Ag, 5090 Leverkusen | Anthrachinon-Reaktivfarbstoffe, deren Herstellung und deren Verwendung |
| DE2654351A1 (de) * | 1976-12-01 | 1978-06-08 | Bayer Ag | Anthrachinon-reaktivfarbstoffe |
| DE2839429A1 (de) * | 1977-09-20 | 1979-03-29 | Sandoz Ag | Anthrachinon-reaktivfarbstoffverbindungen |
| GB2015552B (en) * | 1978-01-24 | 1982-11-17 | Secr Defence | Protein-binding affinity chromatography media |
| JPS635133B2 (enExample) * | 1978-01-24 | 1988-02-02 | Paburitsuku Herusu Raboratarii Saauisu Boodo | |
| DE2817733A1 (de) * | 1978-04-22 | 1979-10-31 | Bayer Ag | Anthrachinon-reaktivfarbstoffe |
| US4273553A (en) * | 1978-11-08 | 1981-06-16 | Bayer Aktiengesellschaft | Anthraquinone reactive dyestuffs |
| DE2852672A1 (de) * | 1978-12-06 | 1980-06-19 | Bayer Ag | Reaktiv-farbstoffe |
| DE2854482A1 (de) * | 1978-12-16 | 1980-06-26 | Bayer Ag | Anthrachinon-reaktivfarbstoffe |
| DE2854483A1 (de) * | 1978-12-16 | 1980-06-26 | Bayer Ag | Anthrachinon-reaktivfarbstoffe |
| DE2854481A1 (de) * | 1978-12-16 | 1980-06-26 | Bayer Ag | Anthrachinon-reaktivfarbstoffe |
| GB8517779D0 (en) * | 1985-07-15 | 1985-08-21 | Ici Plc | Anthraquinone derivatives |
| GB8521328D0 (en) * | 1985-08-27 | 1985-10-02 | Ici Plc | Anthraquinone derivatives |
| US5597485A (en) * | 1988-05-13 | 1997-01-28 | Vilmax S.A. | Process for separating proteins |
| US5728553A (en) * | 1992-09-23 | 1998-03-17 | Delta Biotechnology Limited | High purity albumin and method of producing |
| EP0708151B1 (de) * | 1994-10-14 | 2001-07-11 | Ciba SC Holding AG | Faserreaktive Anthrachinonfarbstoffe, Verfahren zu deren Herstellung und deren Verwendung |
| EP0775776B1 (de) * | 1995-11-23 | 2003-01-02 | Ciba SC Holding AG | Verfahren zum Di- oder Trichromie-Färben oder -Bedrucken |
| GB0228724D0 (en) | 2002-12-09 | 2003-01-15 | Prometic Biosciences Ltd | Multidimensinal libraries |
-
2006
- 2006-03-24 MY MYPI20061310A patent/MY144344A/en unknown
- 2006-03-29 AT AT06725379T patent/ATE509989T1/de active
- 2006-03-29 US US11/887,503 patent/US8227599B2/en not_active Expired - Fee Related
- 2006-03-29 PT PT06725379T patent/PT1866379E/pt unknown
- 2006-03-29 EP EP06725379A patent/EP1866379B1/en not_active Not-in-force
- 2006-03-29 ES ES06725379T patent/ES2366796T3/es active Active
- 2006-03-29 DK DK06725379.9T patent/DK1866379T3/da active
- 2006-03-29 JP JP2008504742A patent/JP5133236B2/ja not_active Expired - Fee Related
- 2006-03-29 SI SI200631080T patent/SI1866379T1/sl unknown
- 2006-03-29 PL PL06725379T patent/PL1866379T3/pl unknown
- 2006-03-29 WO PCT/EP2006/061121 patent/WO2006108760A2/en not_active Ceased
- 2006-04-06 TW TW095112100A patent/TWI415663B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| SI1866379T1 (sl) | 2011-09-30 |
| PT1866379E (pt) | 2011-07-05 |
| US20090081757A1 (en) | 2009-03-26 |
| TW200642741A (en) | 2006-12-16 |
| WO2006108760A2 (en) | 2006-10-19 |
| ATE509989T1 (de) | 2011-06-15 |
| MY144344A (en) | 2011-09-15 |
| EP1866379A2 (en) | 2007-12-19 |
| US8227599B2 (en) | 2012-07-24 |
| TWI415663B (zh) | 2013-11-21 |
| PL1866379T3 (pl) | 2011-10-31 |
| DK1866379T3 (da) | 2011-08-15 |
| WO2006108760A3 (en) | 2007-07-19 |
| ES2366796T3 (es) | 2011-10-25 |
| EP1866379B1 (en) | 2011-05-18 |
| JP2008539280A (ja) | 2008-11-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Lowe et al. | [4] Affinity chromatography on immobilized dyes | |
| Lowe et al. | Design and application of bio-mimetic dyes in biotechnology | |
| RU2175261C2 (ru) | Новые аффинные лиганды и их применение | |
| US4546161A (en) | Media for affinity chromatography | |
| Easterday et al. | Affinity chromatography of kinases and dehydrogenases on Sephadex® and Sepharose® dye derivatives | |
| Labrou et al. | Biomimetic‐dye affinity adsorbents for enzyme purification: Application to the one‐step purification of Candida boidinii formate dehydrogenase | |
| US4913812A (en) | Active support substance and adsorbent for chromatography | |
| US4865990A (en) | Protein adsorbent including a colored compound containing a quaternary ammonium especially amidinium or guanidimium cationic group and a cellulose reactive group | |
| JP5133236B2 (ja) | 生物学的材料を分離するためのアントラキノン染料リガンドを含む吸着剤 | |
| He et al. | Adsorption-desorption of BSA to highly substituted dye-ligand adsorbent: quantitative study of the effect of ionic strength | |
| Clonis et al. | Novel cationic triazine dyes for protein purification | |
| Small et al. | Affinity Labelling of Enzymes with Triazine Dyes: Isolation of a Peptide in the Catalytic Domain of Horse‐Liver Alcohol Dehydrogenase Using Procion Blue MX‐R as a Structural Probe | |
| Labrou et al. | The interaction of Candida boidinii formate dehydrogenase with a new family of chimeric biomimetic dye-ligands | |
| Garg et al. | Dye‐affinity techniques for bioprocessing: Recent developments | |
| WO1991003257A1 (en) | Methods for activating polymeric carriers and compositions prepared therefrom for use in affinity chromatography | |
| US4623625A (en) | Enzyme extraction and purification processes | |
| US4864018A (en) | Anthraquinone derivatives and their use as protein absorbents | |
| Stead | The use of reactive dyes in protein separation processes | |
| Labrou | Dye-ligand affinity chromatography for protein separation and purification | |
| Naumann et al. | Affinity chromatography of bovine heart lactate dehydrogenase using dye ligands linked directly or spacer-mediated to bead cellulose | |
| Guo et al. | Crosslinked mercerized cellulose membranes for the affinity chromatography of papain inhibitors | |
| Hondman et al. | Screening method for large numbers of dye-adsorbents for enzyme purification | |
| Hori et al. | Studies on Gramicidin S Synthetase: Purification and Properties of the Light Enzyme Obtained from Some Mutants of Bacillus brevis | |
| US4851528A (en) | Anthraquinone derivatives | |
| Labrou et al. | Immobilised synthetic dyes in affinity chromatography |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20090327 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20090327 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20111214 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20120110 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20120306 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20120313 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20120710 |
|
| A524 | Written submission of copy of amendment under article 19 pct |
Free format text: JAPANESE INTERMEDIATE CODE: A524 Effective date: 20120710 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20121106 |
|
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20121107 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20151116 Year of fee payment: 3 |
|
| R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| LAPS | Cancellation because of no payment of annual fees |