AU771248B2 - Simple method for labeled conjugate production - Google Patents
Simple method for labeled conjugate production Download PDFInfo
- Publication number
- AU771248B2 AU771248B2 AU25118/00A AU2511800A AU771248B2 AU 771248 B2 AU771248 B2 AU 771248B2 AU 25118/00 A AU25118/00 A AU 25118/00A AU 2511800 A AU2511800 A AU 2511800A AU 771248 B2 AU771248 B2 AU 771248B2
- Authority
- AU
- Australia
- Prior art keywords
- label
- nhs
- components
- reaction
- target
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims abstract description 100
- 238000004519 manufacturing process Methods 0.000 title description 4
- 238000006243 chemical reaction Methods 0.000 claims abstract description 41
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000003153 chemical reaction reagent Substances 0.000 claims description 71
- 150000001412 amines Chemical group 0.000 claims description 19
- 150000001718 carbodiimides Chemical class 0.000 claims description 18
- 230000003213 activating effect Effects 0.000 claims description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 230000004913 activation Effects 0.000 claims description 9
- 239000003638 chemical reducing agent Substances 0.000 claims description 8
- 230000001268 conjugating effect Effects 0.000 claims description 6
- 230000000887 hydrating effect Effects 0.000 claims description 6
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims description 5
- 150000003141 primary amines Chemical class 0.000 claims description 2
- 150000003335 secondary amines Chemical class 0.000 claims description 2
- 230000000052 comparative effect Effects 0.000 claims 2
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims 1
- 240000007594 Oryza sativa Species 0.000 claims 1
- 235000007164 Oryza sativa Nutrition 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 claims 1
- 235000009566 rice Nutrition 0.000 claims 1
- 238000007710 freezing Methods 0.000 abstract description 51
- 230000008014 freezing Effects 0.000 abstract description 51
- 102000004169 proteins and genes Human genes 0.000 abstract description 37
- 108090000623 proteins and genes Proteins 0.000 abstract description 37
- 239000000376 reactant Substances 0.000 abstract description 11
- 238000005859 coupling reaction Methods 0.000 abstract description 9
- 230000009870 specific binding Effects 0.000 abstract description 8
- 230000008878 coupling Effects 0.000 abstract description 7
- 238000010168 coupling process Methods 0.000 abstract description 7
- 230000002123 temporal effect Effects 0.000 abstract description 5
- 230000008569 process Effects 0.000 abstract description 3
- 230000008859 change Effects 0.000 abstract description 2
- 230000000977 initiatory effect Effects 0.000 abstract description 2
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 96
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 48
- 108010090804 Streptavidin Proteins 0.000 description 42
- RPENMORRBUTCPR-UHFFFAOYSA-M sodium;1-hydroxy-2,5-dioxopyrrolidine-3-sulfonate Chemical compound [Na+].ON1C(=O)CC(S([O-])(=O)=O)C1=O RPENMORRBUTCPR-UHFFFAOYSA-M 0.000 description 37
- 239000000243 solution Substances 0.000 description 33
- 229960002685 biotin Drugs 0.000 description 31
- 239000011616 biotin Substances 0.000 description 31
- 239000000872 buffer Substances 0.000 description 31
- 235000018102 proteins Nutrition 0.000 description 30
- 230000027455 binding Effects 0.000 description 28
- 235000020958 biotin Nutrition 0.000 description 24
- 239000000463 material Substances 0.000 description 24
- 230000021615 conjugation Effects 0.000 description 23
- 239000000975 dye Substances 0.000 description 22
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 20
- 150000002148 esters Chemical class 0.000 description 20
- 239000007788 liquid Substances 0.000 description 19
- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 238000007792 addition Methods 0.000 description 18
- HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 description 18
- 239000000843 powder Substances 0.000 description 17
- 108010004469 allophycocyanin Proteins 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- 239000001488 sodium phosphate Substances 0.000 description 16
- 229910000162 sodium phosphate Inorganic materials 0.000 description 16
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 16
- HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 description 12
- 238000004108 freeze drying Methods 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- 238000002372 labelling Methods 0.000 description 11
- 102000004190 Enzymes Human genes 0.000 description 10
- 108090000790 Enzymes Proteins 0.000 description 10
- 108010010522 Phycobilisomes Proteins 0.000 description 10
- 210000002306 phycobilisome Anatomy 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 108060006184 phycobiliprotein Proteins 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 108010004729 Phycoerythrin Proteins 0.000 description 8
- 238000004132 cross linking Methods 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 8
- 238000000159 protein binding assay Methods 0.000 description 8
- 238000000926 separation method Methods 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 238000003860 storage Methods 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 102000039446 nucleic acids Human genes 0.000 description 6
- 108020004707 nucleic acids Proteins 0.000 description 6
- 150000007523 nucleic acids Chemical class 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 102100033620 Calponin-1 Human genes 0.000 description 5
- 101000945318 Homo sapiens Calponin-1 Proteins 0.000 description 5
- 101000652736 Homo sapiens Transgelin Proteins 0.000 description 5
- 239000011324 bead Substances 0.000 description 5
- 239000003431 cross linking reagent Substances 0.000 description 5
- 230000005284 excitation Effects 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000000049 pigment Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000012146 running buffer Substances 0.000 description 5
- JJAHTWIKCUJRDK-UHFFFAOYSA-N succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate Chemical compound C1CC(CN2C(C=CC2=O)=O)CCC1C(=O)ON1C(=O)CCC1=O JJAHTWIKCUJRDK-UHFFFAOYSA-N 0.000 description 5
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- 229920005654 Sephadex Polymers 0.000 description 4
- 239000012507 Sephadex™ Substances 0.000 description 4
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
- 231100000673 dose–response relationship Toxicity 0.000 description 4
- 238000002523 gelfiltration Methods 0.000 description 4
- 238000010791 quenching Methods 0.000 description 4
- 239000011550 stock solution Substances 0.000 description 4
- -1 sulfo-NHS ester Chemical class 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- 108010001336 Horseradish Peroxidase Proteins 0.000 description 3
- HRNLUBSXIHFDHP-UHFFFAOYSA-N N-(2-aminophenyl)-4-[[[4-(3-pyridinyl)-2-pyrimidinyl]amino]methyl]benzamide Chemical compound NC1=CC=CC=C1NC(=O)C(C=C1)=CC=C1CNC1=NC=CC(C=2C=NC=CC=2)=N1 HRNLUBSXIHFDHP-UHFFFAOYSA-N 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- 229920002684 Sepharose Polymers 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 230000008033 biological extinction Effects 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 235000011089 carbon dioxide Nutrition 0.000 description 3
- 150000007942 carboxylates Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 238000004806 packaging method and process Methods 0.000 description 3
- 239000008363 phosphate buffer Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000000171 quenching effect Effects 0.000 description 3
- 241000283707 Capra Species 0.000 description 2
- 108010078791 Carrier Proteins Proteins 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000011033 desalting Methods 0.000 description 2
- 238000000502 dialysis Methods 0.000 description 2
- VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 description 2
- 239000011363 dried mixture Substances 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 239000011344 liquid material Substances 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000012038 nucleophile Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 239000000700 radioactive tracer Substances 0.000 description 2
- JWDFQMWEFLOOED-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 3-(pyridin-2-yldisulfanyl)propanoate Chemical compound O=C1CCC(=O)N1OC(=O)CCSSC1=CC=CC=N1 JWDFQMWEFLOOED-UHFFFAOYSA-N 0.000 description 1
- KYGUQDTWUBBBSD-YIJWYKPTSA-N (8r,9s,10r,13s,14s,17s)-15,17-dihydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4O)O)[C@@H]4[C@@H]3CCC2=C1 KYGUQDTWUBBBSD-YIJWYKPTSA-N 0.000 description 1
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 1
- GVJXGCIPWAVXJP-UHFFFAOYSA-N 2,5-dioxo-1-oxoniopyrrolidine-3-sulfonate Chemical compound ON1C(=O)CC(S(O)(=O)=O)C1=O GVJXGCIPWAVXJP-UHFFFAOYSA-N 0.000 description 1
- MWOOKDULMBMMPN-UHFFFAOYSA-N 3-(2-ethyl-1,2-oxazol-2-ium-5-yl)benzenesulfonate Chemical compound O1[N+](CC)=CC=C1C1=CC=CC(S([O-])(=O)=O)=C1 MWOOKDULMBMMPN-UHFFFAOYSA-N 0.000 description 1
- XDGRAWWEIOPNRC-UHFFFAOYSA-N 3-hydroxy-2,5-dioxopyrrolidine-3-sulfonic acid Chemical compound OS(=O)(=O)C1(O)CC(=O)NC1=O XDGRAWWEIOPNRC-UHFFFAOYSA-N 0.000 description 1
- 125000004042 4-aminobutyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H] 0.000 description 1
- 108091006112 ATPases Proteins 0.000 description 1
- 102000057290 Adenosine Triphosphatases Human genes 0.000 description 1
- 229920000936 Agarose Polymers 0.000 description 1
- 102000002260 Alkaline Phosphatase Human genes 0.000 description 1
- 108020004774 Alkaline Phosphatase Proteins 0.000 description 1
- 240000003291 Armoracia rusticana Species 0.000 description 1
- 235000011330 Armoracia rusticana Nutrition 0.000 description 1
- 240000002900 Arthrospira platensis Species 0.000 description 1
- 235000016425 Arthrospira platensis Nutrition 0.000 description 1
- 102000014914 Carrier Proteins Human genes 0.000 description 1
- 240000008886 Ceratonia siliqua Species 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- 102000016928 DNA-directed DNA polymerase Human genes 0.000 description 1
- 108010014303 DNA-directed DNA polymerase Proteins 0.000 description 1
- 102000004163 DNA-directed RNA polymerases Human genes 0.000 description 1
- 108090000626 DNA-directed RNA polymerases Proteins 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- 102000037909 Folate transporters Human genes 0.000 description 1
- 108091006783 Folate transporters Proteins 0.000 description 1
- 102000020897 Formins Human genes 0.000 description 1
- 108091022623 Formins Proteins 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 206010056740 Genital discharge Diseases 0.000 description 1
- 108010043121 Green Fluorescent Proteins Proteins 0.000 description 1
- 102000004144 Green Fluorescent Proteins Human genes 0.000 description 1
- 102000001706 Immunoglobulin Fab Fragments Human genes 0.000 description 1
- 108010054477 Immunoglobulin Fab Fragments Proteins 0.000 description 1
- 102000018071 Immunoglobulin Fc Fragments Human genes 0.000 description 1
- 108010091135 Immunoglobulin Fc Fragments Proteins 0.000 description 1
- 102000004856 Lectins Human genes 0.000 description 1
- 108090001090 Lectins Proteins 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 108091034117 Oligonucleotide Proteins 0.000 description 1
- 108020005187 Oligonucleotide Probes Proteins 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 108010053210 Phycocyanin Proteins 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- 241001494715 Porphyridium purpureum Species 0.000 description 1
- 241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 description 1
- 229910052771 Terbium Inorganic materials 0.000 description 1
- JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- DZBUGLKDJFMEHC-UHFFFAOYSA-O acridine;hydron Chemical compound C1=CC=CC2=CC3=CC=CC=C3[NH+]=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-O 0.000 description 1
- 150000003838 adenosines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 229940011019 arthrospira platensis Drugs 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012131 assay buffer Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 108091008324 binding proteins Proteins 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 108091005948 blue fluorescent proteins Proteins 0.000 description 1
- 239000008366 buffered solution Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 239000002577 cryoprotective agent Substances 0.000 description 1
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 1
- BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000012595 freezing medium Substances 0.000 description 1
- 239000012520 frozen sample Substances 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
- 239000011521 glass Substances 0.000 description 1
- 150000002337 glycosamines Chemical class 0.000 description 1
- 239000005090 green fluorescent protein Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000003018 immunoassay Methods 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000002523 lectin Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 229960000485 methotrexate Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000002751 oligonucleotide probe Substances 0.000 description 1
- 238000010915 one-step procedure Methods 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- RXNXLAHQOVLMIE-UHFFFAOYSA-N phenyl 10-methylacridin-10-ium-9-carboxylate Chemical compound C12=CC=CC=C2[N+](C)=C2C=CC=CC2=C1C(=O)OC1=CC=CC=C1 RXNXLAHQOVLMIE-UHFFFAOYSA-N 0.000 description 1
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- PTMHPRAIXMAOOB-UHFFFAOYSA-L phosphoramidate Chemical compound NP([O-])([O-])=O PTMHPRAIXMAOOB-UHFFFAOYSA-L 0.000 description 1
- 108010004335 phycoerythrocyanin Proteins 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000011533 pre-incubation Methods 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 239000012460 protein solution Substances 0.000 description 1
- 108010054624 red fluorescent protein Proteins 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 230000009919 sequestration Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012064 sodium phosphate buffer Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical class [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
- 238000003260 vortexing Methods 0.000 description 1
- 108091005957 yellow fluorescent proteins Proteins 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
- G01N33/531—Production of immunochemical test materials
- G01N33/532—Production of labelled immunochemicals
Landscapes
- Health & Medical Sciences (AREA)
- Immunology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Biomedical Technology (AREA)
- Chemical & Material Sciences (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Cell Biology (AREA)
- Food Science & Technology (AREA)
- Medicinal Chemistry (AREA)
- Biotechnology (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Microbiology (AREA)
- Pathology (AREA)
- Peptides Or Proteins (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Pyrrole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11668999P | 1999-01-22 | 1999-01-22 | |
| US60/116689 | 1999-01-22 | ||
| PCT/US2000/001350 WO2000043784A1 (en) | 1999-01-22 | 2000-01-21 | Simple method for labeled conjugate production |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2511800A AU2511800A (en) | 2000-08-07 |
| AU771248B2 true AU771248B2 (en) | 2004-03-18 |
Family
ID=22368643
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU25118/00A Ceased AU771248B2 (en) | 1999-01-22 | 2000-01-21 | Simple method for labeled conjugate production |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP1145007B1 (enExample) |
| JP (1) | JP4731018B2 (enExample) |
| AT (1) | ATE286250T1 (enExample) |
| AU (1) | AU771248B2 (enExample) |
| CA (1) | CA2359234C (enExample) |
| DE (1) | DE60017083T2 (enExample) |
| WO (1) | WO2000043784A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005015212A1 (en) * | 2003-08-07 | 2005-02-17 | Cellfree Sciences Co., Ltd. | Reagent for producing a protein chip |
| GB2478359B (en) * | 2010-03-05 | 2018-09-12 | Innova Biosciences Ltd | Conjugation reactions |
| US8877892B2 (en) | 2011-03-15 | 2014-11-04 | Innova Biosciences Limited | Conjugation reactions |
| JP2017083461A (ja) * | 2016-12-21 | 2017-05-18 | イノーバ・バイオサイエンシズ・リミテッドＩｎｎｏｖａ Ｂｉｏｓｃｉｅｎｃｅｓ Ｌｔｄ | 共役反応 |
| CN109490298B (zh) * | 2018-12-04 | 2021-02-02 | 郑州大学 | 一种可视化偶联反应试剂盒 |
| CN110108868B (zh) * | 2019-05-27 | 2022-09-06 | 蓝怡科技集团股份有限公司 | 一种酶标记的方法及其应用 |
| CN111044732A (zh) * | 2019-12-27 | 2020-04-21 | 桂林优利特医疗电子有限公司 | 用于流式细胞仪法cd45抗原检测的试剂盒及其制备方法 |
| CN114354950A (zh) * | 2022-01-18 | 2022-04-15 | 北京易斯威特生物科技股份有限公司 | 一种性激素功能联合检测用试纸条、制备方法及其应用 |
| CN114539368B (zh) * | 2022-02-16 | 2023-08-29 | 上海万子健生物科技有限公司 | 一种链霉亲和素藻红蛋白冻干粉的制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4732864A (en) * | 1983-10-06 | 1988-03-22 | E. I. Du Pont De Nemours And Company | Trace-labeled conjugates of metallothionein and target-seeking biologically active molecules |
| US5202451A (en) * | 1988-02-17 | 1993-04-13 | Neorx Corporation | Anchimeric radiometal chelating compounds |
| JP2731613B2 (ja) * | 1989-12-12 | 1998-03-25 | 株式会社クラレ | 酵素免疫測定用カートリツジ、それを用いた測定方法及び測定装置 |
| CA2168283A1 (en) * | 1996-01-29 | 1997-07-30 | John Michael Lee | Preparation of biological material for implants |
| ATE250768T1 (de) * | 1996-07-18 | 2003-10-15 | Dade Behring Marburg Gmbh | Reagentien für tests für mycophenolsäure |
-
2000
- 2000-01-21 JP JP2000595154A patent/JP4731018B2/ja not_active Expired - Fee Related
- 2000-01-21 CA CA2359234A patent/CA2359234C/en not_active Expired - Fee Related
- 2000-01-21 EP EP00903358A patent/EP1145007B1/en not_active Expired - Lifetime
- 2000-01-21 WO PCT/US2000/001350 patent/WO2000043784A1/en not_active Ceased
- 2000-01-21 AT AT00903358T patent/ATE286250T1/de not_active IP Right Cessation
- 2000-01-21 AU AU25118/00A patent/AU771248B2/en not_active Ceased
- 2000-01-21 DE DE60017083T patent/DE60017083T2/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| AU2511800A (en) | 2000-08-07 |
| EP1145007B1 (en) | 2004-12-29 |
| JP2002535657A (ja) | 2002-10-22 |
| JP4731018B2 (ja) | 2011-07-20 |
| CA2359234A1 (en) | 2000-07-27 |
| CA2359234C (en) | 2011-11-15 |
| DE60017083D1 (de) | 2005-02-03 |
| DE60017083T2 (de) | 2005-12-22 |
| EP1145007A1 (en) | 2001-10-17 |
| ATE286250T1 (de) | 2005-01-15 |
| WO2000043784A1 (en) | 2000-07-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6809186B1 (en) | Simple method for labeled conjugate production | |
| Weigele et al. | Fluorescent labeling of proteins. A new methodology | |
| US7217575B2 (en) | Avidin derivatives and uses thereof | |
| AU771248B2 (en) | Simple method for labeled conjugate production | |
| JPS6147381B2 (enExample) | ||
| WO2015039423A1 (zh) | 生物标记物的保存液、试剂和方法 | |
| EP0683822B1 (en) | Preparation of photoprotein conjugates and methods of use thereof | |
| Haugland et al. | Coupling of monoclonal antibodies with biotin | |
| US5210040A (en) | Process for coupling antibodies or antibody fragments to liposomes | |
| JP3713087B2 (ja) | ハプテンのイムノアッセイおよびそれに使用可能なハプテントレーサー抗体複合体ならびにそれらの製造方法 | |
| Weston et al. | Conjugation of enzymes to immunoglobulins using dimaleimides | |
| JPS587561A (ja) | 酵素免疫分析法 | |
| JP4102835B2 (ja) | フィコビリソーム、誘導体およびその使用 | |
| Canfi et al. | Multiple labelling of immunoglobulin G, albumin and testosterone with a fluorescent terbium chelate for fluorescence immunoassays | |
| CA1294871C (en) | Immunoassay reagents, kits and methods | |
| US4971916A (en) | Liposome based homogeneous immunoassay for diagnostic tests | |
| Haugland et al. | Preparation of avidin conjugates | |
| Jou et al. | [21] Methods for the attachment of haptens and proteins to erythrocytes | |
| Haugland et al. | Coupling of antibodies with biotin | |
| Haugland et al. | Coupling of antibodies with biotin | |
| US6140090A (en) | Method for the labeling of molecules | |
| Wörner et al. | Coupling Monoclonal Antibodies | |
| Haugland et al. | Coupling of antibodies with biotin | |
| Haugland et al. | Preparation of avidin conjugates | |
| Monji et al. | Conjugation of Haptens and Macromolecules to Phycobiliprotein for Application in Fluorescence Immunoassay |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) |