FI115413B - Vesiliukoisia, polymeeripohjaisia reagensseja ja konjugaatteja, jotka sisältävät divinyylisulfonista johdettuja ryhmiä - Google Patents
Vesiliukoisia, polymeeripohjaisia reagensseja ja konjugaatteja, jotka sisältävät divinyylisulfonista johdettuja ryhmiä Download PDFInfo
- Publication number
- FI115413B FI115413B FI940023A FI940023A FI115413B FI 115413 B FI115413 B FI 115413B FI 940023 A FI940023 A FI 940023A FI 940023 A FI940023 A FI 940023A FI 115413 B FI115413 B FI 115413B
- Authority
- FI
- Finland
- Prior art keywords
- dextran
- water
- soluble
- conjugate
- group
- Prior art date
Links
- 239000003153 chemical reaction reagent Substances 0.000 title claims abstract description 102
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 title claims abstract description 87
- 229920003169 water-soluble polymer Polymers 0.000 title claims description 10
- 229920002307 Dextran Polymers 0.000 claims abstract description 363
- 238000000034 method Methods 0.000 claims abstract description 153
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 97
- 239000000523 sample Substances 0.000 claims abstract description 85
- 238000006243 chemical reaction Methods 0.000 claims abstract description 62
- 108090000623 proteins and genes Proteins 0.000 claims abstract description 40
- 239000000427 antigen Substances 0.000 claims abstract description 38
- 108091007433 antigens Proteins 0.000 claims abstract description 38
- 102000036639 antigens Human genes 0.000 claims abstract description 38
- 102000004190 Enzymes Human genes 0.000 claims abstract description 29
- 108090000790 Enzymes Proteins 0.000 claims abstract description 29
- 238000002360 preparation method Methods 0.000 claims abstract description 29
- 125000000524 functional group Chemical group 0.000 claims abstract description 23
- 239000000126 substance Substances 0.000 claims abstract description 23
- 238000009396 hybridization Methods 0.000 claims abstract description 21
- 125000005647 linker group Chemical group 0.000 claims abstract description 20
- 229920001282 polysaccharide Polymers 0.000 claims abstract description 13
- 239000005017 polysaccharide Substances 0.000 claims abstract description 13
- 229940088597 hormone Drugs 0.000 claims abstract description 7
- 239000005556 hormone Substances 0.000 claims abstract description 7
- 238000000684 flow cytometry Methods 0.000 claims abstract description 5
- 229940079593 drug Drugs 0.000 claims abstract description 4
- 239000003814 drug Substances 0.000 claims abstract description 4
- 150000004676 glycans Chemical class 0.000 claims abstract 4
- 102000002260 Alkaline Phosphatase Human genes 0.000 claims description 135
- 108020004774 Alkaline Phosphatase Proteins 0.000 claims description 135
- 239000002245 particle Substances 0.000 claims description 98
- 108010001336 Horseradish Peroxidase Proteins 0.000 claims description 76
- 229920000642 polymer Polymers 0.000 claims description 53
- 238000002965 ELISA Methods 0.000 claims description 52
- 108010090804 Streptavidin Proteins 0.000 claims description 37
- 108090001008 Avidin Proteins 0.000 claims description 34
- 235000018102 proteins Nutrition 0.000 claims description 33
- 102000004169 proteins and genes Human genes 0.000 claims description 33
- 230000000984 immunochemical effect Effects 0.000 claims description 30
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 30
- 239000007864 aqueous solution Substances 0.000 claims description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- 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 claims description 24
- -1 hydroxypropyl Chemical group 0.000 claims description 23
- 230000008569 process Effects 0.000 claims description 23
- 238000003556 assay Methods 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 20
- 238000009739 binding Methods 0.000 claims description 19
- 230000027455 binding Effects 0.000 claims description 18
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 16
- 229920001184 polypeptide Polymers 0.000 claims description 15
- 229910019142 PO4 Inorganic materials 0.000 claims description 13
- 235000013828 hydroxypropyl starch Nutrition 0.000 claims description 13
- 239000012528 membrane Substances 0.000 claims description 13
- 229960002685 biotin Drugs 0.000 claims description 12
- 235000020958 biotin Nutrition 0.000 claims description 12
- 239000011616 biotin Substances 0.000 claims description 12
- 230000000295 complement effect Effects 0.000 claims description 12
- NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical compound OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 claims description 12
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 claims description 11
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 claims description 11
- 230000002535 lyotropic effect Effects 0.000 claims description 11
- 238000003018 immunoassay Methods 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 8
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 6
- 150000001413 amino acids Chemical class 0.000 claims description 6
- 229920002678 cellulose Polymers 0.000 claims description 6
- 235000010980 cellulose Nutrition 0.000 claims description 6
- 239000002738 chelating agent Substances 0.000 claims description 6
- 230000000269 nucleophilic effect Effects 0.000 claims description 6
- 238000003127 radioimmunoassay Methods 0.000 claims description 6
- 238000010186 staining Methods 0.000 claims description 6
- 239000001913 cellulose Substances 0.000 claims description 5
- 230000003993 interaction Effects 0.000 claims description 5
- 230000002285 radioactive effect Effects 0.000 claims description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 4
- 102000002464 Galactosidases Human genes 0.000 claims description 4
- 108010093031 Galactosidases Proteins 0.000 claims description 4
- 108010015776 Glucose oxidase Proteins 0.000 claims description 4
- 229920002527 Glycogen Polymers 0.000 claims description 4
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 4
- 108090001090 Lectins Proteins 0.000 claims description 4
- 102000004856 Lectins Human genes 0.000 claims description 4
- 108010046334 Urease Proteins 0.000 claims description 4
- 150000001720 carbohydrates Chemical class 0.000 claims description 4
- 235000014633 carbohydrates Nutrition 0.000 claims description 4
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 4
- 230000000093 cytochemical effect Effects 0.000 claims description 4
- 235000019420 glucose oxidase Nutrition 0.000 claims description 4
- 229940096919 glycogen Drugs 0.000 claims description 4
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 4
- 238000012151 immunohistochemical method Methods 0.000 claims description 4
- 239000002523 lectin Substances 0.000 claims description 4
- 230000008685 targeting Effects 0.000 claims description 4
- 102000008857 Ferritin Human genes 0.000 claims description 3
- 108050000784 Ferritin Proteins 0.000 claims description 3
- 238000008416 Ferritin Methods 0.000 claims description 3
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 230000002255 enzymatic effect Effects 0.000 claims description 3
- 238000007901 in situ hybridization Methods 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 229960003330 pentetic acid Drugs 0.000 claims description 3
- 235000021317 phosphate Nutrition 0.000 claims description 3
- 229920000058 polyacrylate Polymers 0.000 claims description 3
- 229920001223 polyethylene glycol Polymers 0.000 claims description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 3
- 235000019422 polyvinyl alcohol Nutrition 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- 229920001059 synthetic polymer Polymers 0.000 claims description 3
- 239000003053 toxin Substances 0.000 claims description 3
- 231100000765 toxin Toxicity 0.000 claims description 3
- 108700012359 toxins Proteins 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- UBQYURCVBFRUQT-UHFFFAOYSA-N N-benzoyl-Ferrioxamine B Chemical compound CC(=O)N(O)CCCCCNC(=O)CCC(=O)N(O)CCCCCNC(=O)CCC(=O)N(O)CCCCCN UBQYURCVBFRUQT-UHFFFAOYSA-N 0.000 claims description 2
- 108091034117 Oligonucleotide Proteins 0.000 claims description 2
- 101710120037 Toxin CcdB Proteins 0.000 claims description 2
- 150000001860 citric acid derivatives Chemical class 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 150000002772 monosaccharides Chemical class 0.000 claims description 2
- 229920001206 natural gum Polymers 0.000 claims description 2
- 150000002482 oligosaccharides Polymers 0.000 claims description 2
- 108091033319 polynucleotide Proteins 0.000 claims description 2
- 102000040430 polynucleotide Human genes 0.000 claims description 2
- 239000002157 polynucleotide Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 150000003892 tartrate salts Chemical class 0.000 claims description 2
- 229920001612 Hydroxyethyl starch Polymers 0.000 claims 3
- 229920002472 Starch Polymers 0.000 claims 3
- 235000019698 starch Nutrition 0.000 claims 3
- 244000043261 Hevea brasiliensis Species 0.000 claims 2
- 239000003086 colorant Substances 0.000 claims 2
- 229920003052 natural elastomer Polymers 0.000 claims 2
- 229920001194 natural rubber Polymers 0.000 claims 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims 1
- 239000001768 carboxy methyl cellulose Substances 0.000 claims 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 claims 1
- 229940105329 carboxymethylcellulose Drugs 0.000 claims 1
- 229920001249 ethyl cellulose Polymers 0.000 claims 1
- 235000019325 ethyl cellulose Nutrition 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000003102 growth factor Substances 0.000 claims 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims 1
- 238000001514 detection method Methods 0.000 abstract description 32
- 229940088598 enzyme Drugs 0.000 abstract description 27
- 238000000746 purification Methods 0.000 abstract description 7
- 125000003396 thiol group Chemical group [H]S* 0.000 abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 5
- 238000003364 immunohistochemistry Methods 0.000 abstract description 5
- 239000000975 dye Substances 0.000 abstract description 4
- 238000000926 separation method Methods 0.000 abstract description 4
- 238000011002 quantification Methods 0.000 abstract description 3
- 230000021615 conjugation Effects 0.000 abstract description 2
- 238000012360 testing method Methods 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 215
- 238000010168 coupling process Methods 0.000 description 117
- 238000005859 coupling reaction Methods 0.000 description 106
- 230000008878 coupling Effects 0.000 description 103
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 81
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 74
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 73
- 241000283973 Oryctolagus cuniculus Species 0.000 description 70
- 241000283707 Capra Species 0.000 description 56
- 238000002523 gelfiltration Methods 0.000 description 52
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 46
- 238000011534 incubation Methods 0.000 description 41
- 238000010348 incorporation Methods 0.000 description 39
- 239000012506 Sephacryl® Substances 0.000 description 33
- 241000699666 Mus <mouse, genus> Species 0.000 description 32
- 108060003951 Immunoglobulin Proteins 0.000 description 31
- 238000002835 absorbance Methods 0.000 description 31
- 230000000694 effects Effects 0.000 description 31
- 102000018358 immunoglobulin Human genes 0.000 description 31
- 230000004913 activation Effects 0.000 description 27
- 239000011780 sodium chloride Substances 0.000 description 23
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 20
- 239000012634 fragment Substances 0.000 description 19
- 239000000203 mixture Substances 0.000 description 19
- 102000003992 Peroxidases Human genes 0.000 description 18
- 229940072221 immunoglobulins Drugs 0.000 description 18
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 17
- 238000005406 washing Methods 0.000 description 17
- 108040007629 peroxidase activity proteins Proteins 0.000 description 16
- 229920000136 polysorbate Polymers 0.000 description 16
- 230000035945 sensitivity Effects 0.000 description 15
- 238000003756 stirring Methods 0.000 description 15
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 14
- HAXFWIACAGNFHA-UHFFFAOYSA-N aldrithiol Chemical group C=1C=CC=NC=1SSC1=CC=CC=N1 HAXFWIACAGNFHA-UHFFFAOYSA-N 0.000 description 14
- 239000000758 substrate Substances 0.000 description 14
- 239000012279 sodium borohydride Substances 0.000 description 12
- 229910000033 sodium borohydride Inorganic materials 0.000 description 12
- 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 11
- 238000010790 dilution Methods 0.000 description 11
- 239000012895 dilution Substances 0.000 description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 11
- 239000010452 phosphate Substances 0.000 description 11
- 239000004471 Glycine Substances 0.000 description 10
- 230000000890 antigenic effect Effects 0.000 description 10
- 238000000502 dialysis Methods 0.000 description 10
- VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 description 10
- MHMNJMPURVTYEJ-UHFFFAOYSA-N fluorescein-5-isothiocyanate Chemical compound O1C(=O)C2=CC(N=C=S)=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 MHMNJMPURVTYEJ-UHFFFAOYSA-N 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 9
- 239000000872 buffer Substances 0.000 description 9
- 239000000969 carrier Substances 0.000 description 9
- 108010074605 gamma-Globulins Proteins 0.000 description 9
- 239000003550 marker Substances 0.000 description 9
- 150000004804 polysaccharides Chemical class 0.000 description 9
- 238000001556 precipitation Methods 0.000 description 9
- 238000004448 titration Methods 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- 241000283690 Bos taurus Species 0.000 description 8
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 8
- 239000001341 hydroxy propyl starch Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 230000009257 reactivity Effects 0.000 description 8
- 210000001519 tissue Anatomy 0.000 description 8
- 239000000020 Nitrocellulose Substances 0.000 description 7
- 229920002684 Sepharose Polymers 0.000 description 7
- 229940098773 bovine serum albumin Drugs 0.000 description 7
- 230000009918 complex formation Effects 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- 230000001900 immune effect Effects 0.000 description 7
- 229920001220 nitrocellulos Polymers 0.000 description 7
- 230000035484 reaction time Effects 0.000 description 7
- 239000001488 sodium phosphate Substances 0.000 description 7
- 229910000162 sodium phosphate Inorganic materials 0.000 description 7
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 7
- 102000004506 Blood Proteins Human genes 0.000 description 6
- 108010017384 Blood Proteins Proteins 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- 230000008901 benefit Effects 0.000 description 6
- 239000000499 gel Substances 0.000 description 6
- 230000002055 immunohistochemical effect Effects 0.000 description 6
- 239000008363 phosphate buffer Substances 0.000 description 6
- 238000013207 serial dilution Methods 0.000 description 6
- 108020004414 DNA Proteins 0.000 description 5
- 102000004160 Phosphoric Monoester Hydrolases Human genes 0.000 description 5
- 108090000608 Phosphoric Monoester Hydrolases Proteins 0.000 description 5
- 239000007983 Tris buffer Substances 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 5
- 239000007850 fluorescent dye Substances 0.000 description 5
- 238000007429 general method Methods 0.000 description 5
- 150000007523 nucleic acids Chemical class 0.000 description 5
- 229920000656 polylysine Polymers 0.000 description 5
- 239000000700 radioactive tracer Substances 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 238000006177 thiolation reaction Methods 0.000 description 5
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 5
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 4
- 240000003291 Armoracia rusticana Species 0.000 description 4
- 235000011330 Armoracia rusticana Nutrition 0.000 description 4
- XUIIKFGFIJCVMT-GFCCVEGCSA-N D-thyroxine Chemical compound IC1=CC(C[C@@H](N)C(O)=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 XUIIKFGFIJCVMT-GFCCVEGCSA-N 0.000 description 4
- 108091028043 Nucleic acid sequence Proteins 0.000 description 4
- 108010039918 Polylysine Proteins 0.000 description 4
- GPKUGWDQUVWHIC-UHFFFAOYSA-N [4-(4-hydrazinylphenyl)phenyl]hydrazine tetrahydrochloride Chemical compound Cl.Cl.Cl.Cl.NNC1=CC=C(C=C1)C1=CC=C(NN)C=C1 GPKUGWDQUVWHIC-UHFFFAOYSA-N 0.000 description 4
- 238000013019 agitation Methods 0.000 description 4
- 235000001014 amino acid Nutrition 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 230000003321 amplification Effects 0.000 description 4
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 4
- 125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 description 4
- 230000009849 deactivation Effects 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 4
- 239000010931 gold Substances 0.000 description 4
- 238000002991 immunohistochemical analysis Methods 0.000 description 4
- 238000012744 immunostaining Methods 0.000 description 4
- 238000011068 loading method Methods 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 238000003199 nucleic acid amplification method Methods 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 239000007790 solid phase Substances 0.000 description 4
- 238000001179 sorption measurement Methods 0.000 description 4
- 238000007447 staining method Methods 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 229940034208 thyroxine Drugs 0.000 description 4
- XUIIKFGFIJCVMT-UHFFFAOYSA-N thyroxine-binding globulin Natural products IC1=CC(CC([NH3+])C([O-])=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 XUIIKFGFIJCVMT-UHFFFAOYSA-N 0.000 description 4
- GZAJOEGTZDUSKS-UHFFFAOYSA-N 5-aminofluorescein Chemical compound C12=CC=C(O)C=C2OC2=CC(O)=CC=C2C21OC(=O)C1=CC(N)=CC=C21 GZAJOEGTZDUSKS-UHFFFAOYSA-N 0.000 description 3
- 229910052693 Europium Inorganic materials 0.000 description 3
- 241001529936 Murinae Species 0.000 description 3
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 3
- 239000012507 Sephadex™ Substances 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 239000011543 agarose gel Substances 0.000 description 3
- 125000000539 amino acid group Chemical group 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 235000018417 cysteine Nutrition 0.000 description 3
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 3
- 230000004927 fusion Effects 0.000 description 3
- 229910052737 gold Inorganic materials 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 229910052747 lanthanoid Inorganic materials 0.000 description 3
- 150000002602 lanthanoids Chemical class 0.000 description 3
- 108020004707 nucleic acids Proteins 0.000 description 3
- 102000039446 nucleic acids Human genes 0.000 description 3
- 239000002773 nucleotide Substances 0.000 description 3
- 125000003729 nucleotide group Chemical group 0.000 description 3
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 235000011149 sulphuric acid Nutrition 0.000 description 3
- 238000012800 visualization Methods 0.000 description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 101100283604 Caenorhabditis elegans pigk-1 gene Proteins 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 244000250392 Cardamine diphylla Species 0.000 description 2
- 235000001250 Cardamine diphylla Nutrition 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 108010000912 Egg Proteins Proteins 0.000 description 2
- 102000002322 Egg Proteins Human genes 0.000 description 2
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 108700020962 Peroxidase Proteins 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 2
- 108010072866 Prostate-Specific Antigen Proteins 0.000 description 2
- 102100038358 Prostate-specific antigen Human genes 0.000 description 2
- 229920005654 Sephadex Polymers 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000002479 acid--base titration Methods 0.000 description 2
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 2
- 210000004899 c-terminal region Anatomy 0.000 description 2
- 150000001718 carbodiimides Chemical class 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 2
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- HWYHZTIRURJOHG-UHFFFAOYSA-N luminol Chemical compound O=C1NNC(=O)C2=C1C(N)=CC=C2 HWYHZTIRURJOHG-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 230000009871 nonspecific binding Effects 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000007420 reactivation Effects 0.000 description 2
- 239000012070 reactive reagent Substances 0.000 description 2
- 238000009938 salting Methods 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
- 235000019345 sodium thiosulphate Nutrition 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 239000011534 wash buffer Substances 0.000 description 2
- 238000001262 western blot Methods 0.000 description 2
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 1
- FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 1
- GPUBPSKTFNYPHI-AYGRAXKESA-N 3-[5-[(3as,4s,6ar)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoyl]-1-hydroxypyrrolidine-2,5-dione Chemical compound O=C1N(O)C(=O)CC1C(=O)CCCC[C@H]1[C@H]2NC(=O)N[C@H]2CS1 GPUBPSKTFNYPHI-AYGRAXKESA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- FWEOQOXTVHGIFQ-UHFFFAOYSA-N 8-anilinonaphthalene-1-sulfonic acid Chemical compound C=12C(S(=O)(=O)O)=CC=CC2=CC=CC=1NC1=CC=CC=C1 FWEOQOXTVHGIFQ-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 229920002126 Acrylic acid copolymer Polymers 0.000 description 1
- 229920000936 Agarose Polymers 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 108010051479 Bombesin Proteins 0.000 description 1
- 102000013585 Bombesin Human genes 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- 229920001661 Chitosan Polymers 0.000 description 1
- MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 description 1
- MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- 102000004127 Cytokines Human genes 0.000 description 1
- 108090000695 Cytokines Proteins 0.000 description 1
- 101710101803 DNA-binding protein J Proteins 0.000 description 1
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- 241000854350 Enicospilus group Species 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- 102400000921 Gastrin Human genes 0.000 description 1
- 108010052343 Gastrins Proteins 0.000 description 1
- 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 1
- 229930186217 Glycolipid Natural products 0.000 description 1
- 108090000288 Glycoproteins Proteins 0.000 description 1
- 102000003886 Glycoproteins Human genes 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 108010021625 Immunoglobulin Fragments Proteins 0.000 description 1
- 102000008394 Immunoglobulin Fragments Human genes 0.000 description 1
- 108090001061 Insulin Proteins 0.000 description 1
- 102000004877 Insulin Human genes 0.000 description 1
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 1
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 102000057297 Pepsin A Human genes 0.000 description 1
- 108090000284 Pepsin A Proteins 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 1
- 229920002873 Polyethylenimine Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 238000002105 Southern blotting Methods 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 1
- 239000004473 Threonine Substances 0.000 description 1
- 108010034949 Thyroglobulin Proteins 0.000 description 1
- 102000009843 Thyroglobulin Human genes 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 241000396377 Tranes Species 0.000 description 1
- 102000004338 Transferrin Human genes 0.000 description 1
- 108090000901 Transferrin Proteins 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- GXBMIBRIOWHPDT-UHFFFAOYSA-N Vasopressin Natural products N1C(=O)C(CC=2C=C(O)C=CC=2)NC(=O)C(N)CSSCC(C(=O)N2C(CCC2)C(=O)NC(CCCN=C(N)N)C(=O)NCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C1CC1=CC=CC=C1 GXBMIBRIOWHPDT-UHFFFAOYSA-N 0.000 description 1
- 108010004977 Vasopressins Proteins 0.000 description 1
- 102000002852 Vasopressins Human genes 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- SXEHKFHPFVVDIR-UHFFFAOYSA-N [4-(4-hydrazinylphenyl)phenyl]hydrazine Chemical compound C1=CC(NN)=CC=C1C1=CC=C(NN)C=C1 SXEHKFHPFVVDIR-UHFFFAOYSA-N 0.000 description 1
- 238000011481 absorbance measurement Methods 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 229920006322 acrylamide copolymer Polymers 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000001261 affinity purification Methods 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 229960002684 aminocaproic acid Drugs 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical class N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 238000004873 anchoring Methods 0.000 description 1
- 230000001745 anti-biotin effect Effects 0.000 description 1
- 239000012431 aqueous reaction media Substances 0.000 description 1
- KBZOIRJILGZLEJ-LGYYRGKSSA-N argipressin Chemical compound C([C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@@H](C(N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N1)=O)N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)NCC(N)=O)C1=CC=CC=C1 KBZOIRJILGZLEJ-LGYYRGKSSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 238000000376 autoradiography Methods 0.000 description 1
- 108010030694 avidin-horseradish peroxidase complex Proteins 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- DNDCVAGJPBKION-DOPDSADYSA-N bombesin Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(N)=O)NC(=O)CNC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CC=1NC2=CC=CC=C2C=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H]1NC(=O)CC1)C(C)C)C1=CN=CN1 DNDCVAGJPBKION-DOPDSADYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- AOXOCDRNSPFDPE-UKEONUMOSA-N chembl413654 Chemical compound C([C@H](C(=O)NCC(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@H](CCSC)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](C)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]1N(CCC1)C(=O)CNC(=O)[C@@H](N)CCC(O)=O)C1=CC=C(O)C=C1 AOXOCDRNSPFDPE-UKEONUMOSA-N 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 229960004544 cortisone Drugs 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 239000004148 curcumin Substances 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000002242 deionisation method Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 229940041984 dextran 1 Drugs 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- 239000013024 dilution buffer Substances 0.000 description 1
- 239000012897 dilution medium Substances 0.000 description 1
- 150000002009 diols Chemical group 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000007515 enzymatic degradation Effects 0.000 description 1
- IINNWAYUJNWZRM-UHFFFAOYSA-L erythrosin B Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=C(I)C(=O)C(I)=C2OC2=C(I)C([O-])=C(I)C=C21 IINNWAYUJNWZRM-UHFFFAOYSA-L 0.000 description 1
- 239000004174 erythrosine Substances 0.000 description 1
- 235000012732 erythrosine Nutrition 0.000 description 1
- 229940011411 erythrosine Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229940011871 estrogen Drugs 0.000 description 1
- 239000000262 estrogen Substances 0.000 description 1
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000000799 fluorescence microscopy Methods 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 238000001502 gel electrophoresis Methods 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000009499 grossing Methods 0.000 description 1
- 239000000383 hazardous chemical Substances 0.000 description 1
- 231100000206 health hazard Toxicity 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000000487 histidyl group Chemical group [H]N([H])C(C(=O)O*)C([H])([H])C1=C([H])N([H])C([H])=N1 0.000 description 1
- 230000001744 histochemical effect Effects 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- UMHAZRHZAQYINK-UCLGWUJRSA-N hrp-5 Chemical compound C([C@@H](C(=O)N[C@@H](C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC1N=CN=C1)C(=O)N[C@@H](CC1N=CN=C1)C(=O)NCC(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCCN)C(=O)OC(=O)CC[C@H](NC(=O)[C@H](CC1N=CN=C1)NC(=O)[C@@H](N)CC=1C=CC=CC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC1N=CN=C1)C(=O)N[C@@H](CC1N=CN=C1)C(=O)OC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC1N=CN=C1)NC(=O)[C@@H](N)CO)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC(O)=O)C1C=NC=N1 UMHAZRHZAQYINK-UCLGWUJRSA-N 0.000 description 1
- LFKYBJLFJOOKAE-UHFFFAOYSA-N imidazol-2-ylidenemethanone Chemical compound O=C=C1N=CC=N1 LFKYBJLFJOOKAE-UHFFFAOYSA-N 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 239000012678 infectious agent Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229940125396 insulin Drugs 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000004807 localization Effects 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000012149 noodles Nutrition 0.000 description 1
- QYSGYZVSCZSLHT-UHFFFAOYSA-N octafluoropropane Chemical compound FC(F)(F)C(F)(F)C(F)(F)F QYSGYZVSCZSLHT-UHFFFAOYSA-N 0.000 description 1
- AHLPHDHHMVZTML-BYPYZUCNSA-N ornithyl group Chemical group N[C@@H](CCCN)C(=O)O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 229940111202 pepsin Drugs 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-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
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 238000002264 polyacrylamide gel electrophoresis Methods 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920002704 polyhistidine Polymers 0.000 description 1
- 229920000307 polymer substrate Polymers 0.000 description 1
- 229920002714 polyornithine Polymers 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- 238000011533 pre-incubation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 229960003387 progesterone Drugs 0.000 description 1
- 239000000186 progesterone Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000003270 steroid hormone Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052713 technetium Inorganic materials 0.000 description 1
- GKLVYJBZJHMRIY-UHFFFAOYSA-N technetium atom Chemical compound [Tc] GKLVYJBZJHMRIY-UHFFFAOYSA-N 0.000 description 1
- 229940006280 thiosulfate ion Drugs 0.000 description 1
- 229960002175 thyroglobulin Drugs 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 239000012581 transferrin Substances 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 125000001493 tyrosinyl group Chemical group [H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 229960003726 vasopressin Drugs 0.000 description 1
- UIYCHXAGWOYNNA-UHFFFAOYSA-N vinyl sulfide Chemical compound C=CSC=C UIYCHXAGWOYNNA-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 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
- G01N33/543—Immunoassay; Biospecific binding assay; Materials therefor with an insoluble carrier for immobilising immunochemicals
- G01N33/54353—Immunoassay; Biospecific binding assay; Materials therefor with an insoluble carrier for immobilising immunochemicals with ligand attached to the carrier via a chemical coupling agent
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)
- Cell Biology (AREA)
- Food Science & Technology (AREA)
- Medicinal Chemistry (AREA)
- Biotechnology (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Microbiology (AREA)
- Peptides Or Proteins (AREA)
- Cephalosporin Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Graft Or Block Polymers (AREA)
- Saccharide Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Immobilizing And Processing Of Enzymes And Microorganisms (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK130991 | 1991-07-04 | ||
| DK911309A DK130991D0 (da) | 1991-07-04 | 1991-07-04 | Polymere konjugater |
| US78975791 | 1991-11-08 | ||
| US07/789,757 US5543332A (en) | 1991-07-04 | 1991-11-08 | Water-soluble, polymer-based reagents and conjugates comprising moieties derived from divinyl sulfone |
| PCT/DK1992/000206 WO1993001498A1 (en) | 1991-07-04 | 1992-06-29 | Water-soluble, polymer-based reagents and conjugates comprising moieties derived from divinyl sulfone |
| DK9200206 | 1992-06-29 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI940023A0 FI940023A0 (fi) | 1994-01-04 |
| FI940023A7 FI940023A7 (fi) | 1994-02-25 |
| FI115413B true FI115413B (fi) | 2005-04-29 |
Family
ID=26065568
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI940023A FI115413B (fi) | 1991-07-04 | 1994-01-04 | Vesiliukoisia, polymeeripohjaisia reagensseja ja konjugaatteja, jotka sisältävät divinyylisulfonista johdettuja ryhmiä |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP0594772B1 (enExample) |
| JP (1) | JP3340434B2 (enExample) |
| AT (1) | ATE142021T1 (enExample) |
| AU (1) | AU667051B2 (enExample) |
| CA (1) | CA2112992C (enExample) |
| DE (1) | DE69213240T2 (enExample) |
| DK (1) | DK0594772T3 (enExample) |
| ES (1) | ES2094920T3 (enExample) |
| FI (1) | FI115413B (enExample) |
| GR (1) | GR3021806T3 (enExample) |
| NO (1) | NO315443B1 (enExample) |
| WO (1) | WO1993001498A1 (enExample) |
Families Citing this family (86)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6552170B1 (en) * | 1990-04-06 | 2003-04-22 | Amgen Inc. | PEGylation reagents and compounds formed therewith |
| US5773227A (en) * | 1993-06-23 | 1998-06-30 | Molecular Probes, Inc. | Bifunctional chelating polysaccharides |
| US5446090A (en) * | 1993-11-12 | 1995-08-29 | Shearwater Polymers, Inc. | Isolatable, water soluble, and hydrolytically stable active sulfones of poly(ethylene glycol) and related polymers for modification of surfaces and molecules |
| WO1995032305A1 (en) | 1994-05-19 | 1995-11-30 | Dako A/S | Pna probes for detection of neisseria gonorrhoeae and chlamydia trachomatis |
| US5888733A (en) * | 1995-11-16 | 1999-03-30 | Dako A/S | In situ hybridization to detect specific nucleic acid sequences in eucaryotic samples |
| US5747639A (en) * | 1996-03-06 | 1998-05-05 | Amgen Boulder Inc. | Use of hydrophobic interaction chromatography to purify polyethylene glycols |
| US6309646B1 (en) | 1996-05-09 | 2001-10-30 | The Henry M. Jackson Foundation For The Advancement Of Military Medicine | Protein-polysaccharide conjugate vaccines and other immunological reagents prepared using homobifunctional and heterobifunctional vinylsulfones, and processes for preparing the conjugates |
| TW555765B (en) | 1996-07-09 | 2003-10-01 | Amgen Inc | Low molecular weight soluble tumor necrosis factor type-I and type-II proteins |
| GB9624165D0 (en) * | 1996-11-19 | 1997-01-08 | Amdex A S | Use of nucleic acids bound to carrier macromolecules |
| EP0942740B1 (en) | 1996-12-06 | 2003-08-27 | Amgen Inc., | Combination therapy using a tnf binding protein for treating tnf-mediated diseases |
| US6709873B1 (en) * | 1997-04-09 | 2004-03-23 | Isodiagnostika Inc. | Method for production of antibodies to specific sites of rapamycin |
| US5994089A (en) * | 1997-05-16 | 1999-11-30 | Coulter International Corp. | Simultaneous analyses of white blood cell subsets using multi-color, multi-intensity fluorescent markers in flow cytometry |
| US6066446A (en) * | 1997-12-19 | 2000-05-23 | Nen Life Science Products, Inc. | Assay member and method for its manufacture |
| WO1999040438A1 (en) * | 1998-02-03 | 1999-08-12 | Synbiotics Corporation | Device and method to detect immunoprotective antibody titers |
| DK1101115T3 (da) * | 1998-07-30 | 2004-10-25 | Oakville Trading Hong Kong Ltd | Fremgangsmåde til fremstilling af vandoplöselige tværbundne konjugater |
| US6686454B1 (en) * | 1998-10-09 | 2004-02-03 | Isotechnika, Inc. | Antibodies to specific regions of cyclosporine related compounds |
| WO2000022000A1 (en) * | 1998-10-09 | 2000-04-20 | Isotechnika, Inc. | Methods for the production of antibodies to specific regions of cyclosporine and cyclosporine metabolites |
| US6660843B1 (en) | 1998-10-23 | 2003-12-09 | Amgen Inc. | Modified peptides as therapeutic agents |
| JP3781934B2 (ja) | 1999-12-22 | 2006-06-07 | 株式会社ニチレイバイオサイエンス | 酵素−タンパク質複合体 |
| DE10039112A1 (de) * | 2000-08-07 | 2002-03-07 | Pe Diagnostik Gmbh | Verfahren zum Herstellen von Antikörper aus einer verunreinigten Antigenlösung |
| GB0029617D0 (en) * | 2000-12-05 | 2001-01-17 | Norchip As | Ligand detection method |
| ES2747357T3 (es) | 2001-03-14 | 2020-03-10 | Dako Denmark As | Construcciones de moléculas MHC y sus usos para el diagnóstico y terapia |
| US7034127B2 (en) * | 2002-07-02 | 2006-04-25 | Genzyme Corporation | Hydrophilic biopolymer-drug conjugates, their preparation and use |
| EP1405907A3 (en) * | 2002-07-22 | 2004-10-13 | Roche Diagnostics GmbH | Conjugate of a tissue non-specific alkaline phosphatase and dextran, process for its production and use thereof |
| CA2433479A1 (en) | 2002-07-22 | 2004-01-22 | F. Hoffmann-La Roche Ag | Conjugate of a tissue non-specific alkaline phosphatase and dextran, process for its production and use thereof |
| WO2005062048A1 (de) | 2003-12-01 | 2005-07-07 | Dade Behring Marburg Gmbh | Homogenes nachweisverfahren |
| WO2005054860A1 (en) | 2003-12-01 | 2005-06-16 | Dako Denmark A/S | Methods and compositions for immuno-histochemical detection |
| CA2547353A1 (en) * | 2003-12-01 | 2005-07-07 | Dade Behring Marburg Gmbh | Conjugates, and use thereof in detection methods |
| GB0426823D0 (en) | 2004-12-07 | 2005-01-12 | Precisense As | Sensor for detection of glucose |
| GB0426822D0 (en) | 2004-12-07 | 2005-01-12 | Precisense As | Sensor for detection of glucose |
| KR101354114B1 (ko) | 2005-06-14 | 2014-01-24 | 타이젠 바이오테크놀러지 컴퍼니 리미티드 | 피리미딘 화합물 |
| US8193206B2 (en) | 2005-06-14 | 2012-06-05 | Taigen Biotechnology Co., Ltd. | Pyrimidine compounds |
| JP2009530639A (ja) | 2006-03-20 | 2009-08-27 | インバーネス・メデイカル・スウイツツアーランド・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング | 電気化学的検出のための水溶性コンジュゲート |
| EP2155782A2 (en) * | 2007-03-26 | 2010-02-24 | Dako Denmark A/S | Mhc peptide complexes and uses thereof in infectious diseases |
| EP3620465B1 (en) | 2007-07-03 | 2025-02-19 | Dako Denmark A/S | Improved methods for generation, labeling and use of mhc multimers |
| US10611818B2 (en) | 2007-09-27 | 2020-04-07 | Agilent Technologies, Inc. | MHC multimers in tuberculosis diagnostics, vaccine and therapeutics |
| DK2254592T3 (da) | 2008-02-28 | 2019-09-09 | Dako Denmark As | MHC-multimerer til Borrelia-diagnostik og sygdom |
| SI2268635T1 (sl) | 2008-04-21 | 2015-10-30 | Taigen Biotechnology Co., Ltd. | Heterociklične spojine |
| WO2010009735A2 (en) | 2008-07-23 | 2010-01-28 | Dako Denmark A/S | Combinatorial analysis and repair |
| WO2010031749A1 (en) | 2008-09-17 | 2010-03-25 | Innate Pharma | Compositions and methods for detecting tlr3 |
| GB0817244D0 (en) | 2008-09-20 | 2008-10-29 | Univ Cardiff | Use of a protein kinase inhibitor to detect immune cells, such as T cells |
| US10369204B2 (en) | 2008-10-02 | 2019-08-06 | Dako Denmark A/S | Molecular vaccines for infectious disease |
| US11992518B2 (en) | 2008-10-02 | 2024-05-28 | Agilent Technologies, Inc. | Molecular vaccines for infectious disease |
| US9023834B2 (en) | 2008-11-13 | 2015-05-05 | Taigen Biotechnology Co., Ltd. | Lyophilization formulation |
| EP2270506A3 (en) * | 2009-07-02 | 2011-03-09 | Amic AB | Amplified labeled conjugate for use in immunoassays |
| WO2011050938A1 (de) | 2009-10-26 | 2011-05-05 | Genovoxx Gmbh | Konjugate von nukleotiden und methoden zu deren anwendung |
| US10752949B2 (en) | 2012-08-14 | 2020-08-25 | 10X Genomics, Inc. | Methods and systems for processing polynucleotides |
| CN111748607B (zh) | 2012-08-14 | 2024-04-30 | 10X基因组学有限公司 | 微胶囊组合物及方法 |
| US9701998B2 (en) | 2012-12-14 | 2017-07-11 | 10X Genomics, Inc. | Methods and systems for processing polynucleotides |
| US10400280B2 (en) | 2012-08-14 | 2019-09-03 | 10X Genomics, Inc. | Methods and systems for processing polynucleotides |
| US9951386B2 (en) | 2014-06-26 | 2018-04-24 | 10X Genomics, Inc. | Methods and systems for processing polynucleotides |
| US10273541B2 (en) | 2012-08-14 | 2019-04-30 | 10X Genomics, Inc. | Methods and systems for processing polynucleotides |
| US11591637B2 (en) | 2012-08-14 | 2023-02-28 | 10X Genomics, Inc. | Compositions and methods for sample processing |
| US10323279B2 (en) | 2012-08-14 | 2019-06-18 | 10X Genomics, Inc. | Methods and systems for processing polynucleotides |
| CA2894694C (en) | 2012-12-14 | 2023-04-25 | 10X Genomics, Inc. | Methods and systems for processing polynucleotides |
| US10533221B2 (en) | 2012-12-14 | 2020-01-14 | 10X Genomics, Inc. | Methods and systems for processing polynucleotides |
| WO2014124338A1 (en) | 2013-02-08 | 2014-08-14 | 10X Technologies, Inc. | Polynucleotide barcode generation |
| WO2014208776A1 (ja) | 2013-06-28 | 2014-12-31 | 国立大学法人九州大学 | タンパク質－ポリマ複合体、ＴＧａｓｅ基質含有ポリマ、ＴＧａｓｅ基質含有モノマ、タンパク質－ポリマ複合体の製造方法、および固液の界面あるいは界面近傍でタンパク質機能を高める方法 |
| CN114534806B (zh) | 2014-04-10 | 2024-03-29 | 10X基因组学有限公司 | 用于封装和分割试剂的流体装置、系统和方法及其应用 |
| EP3155426B1 (en) | 2014-06-13 | 2023-07-19 | Immudex ApS | General detection and isolation of specific cells by binding of labeled molecules |
| CN113249435B (zh) | 2014-06-26 | 2024-09-03 | 10X基因组学有限公司 | 分析来自单个细胞或细胞群体的核酸的方法 |
| CN106536756A (zh) | 2014-06-26 | 2017-03-22 | 10X基因组学有限公司 | 核酸序列的分析 |
| US12312640B2 (en) | 2014-06-26 | 2025-05-27 | 10X Genomics, Inc. | Analysis of nucleic acid sequences |
| SG11201705615UA (en) | 2015-01-12 | 2017-08-30 | 10X Genomics Inc | Processes and systems for preparing nucleic acid sequencing libraries and libraries prepared using same |
| WO2016137973A1 (en) | 2015-02-24 | 2016-09-01 | 10X Genomics Inc | Partition processing methods and systems |
| SG11201804086VA (en) | 2015-12-04 | 2018-06-28 | 10X Genomics Inc | Methods and compositions for nucleic acid analysis |
| WO2017157980A1 (en) | 2016-03-15 | 2017-09-21 | Mipsalus Aps | Detection method and means therefor |
| US10815525B2 (en) | 2016-12-22 | 2020-10-27 | 10X Genomics, Inc. | Methods and systems for processing polynucleotides |
| US10011872B1 (en) | 2016-12-22 | 2018-07-03 | 10X Genomics, Inc. | Methods and systems for processing polynucleotides |
| US10550429B2 (en) | 2016-12-22 | 2020-02-04 | 10X Genomics, Inc. | Methods and systems for processing polynucleotides |
| EP3545089B1 (en) | 2017-01-30 | 2022-03-09 | 10X Genomics, Inc. | Methods and systems for droplet-based single cell barcoding |
| CN116064732A (zh) | 2017-05-26 | 2023-05-05 | 10X基因组学有限公司 | 转座酶可接近性染色质的单细胞分析 |
| US20180340169A1 (en) | 2017-05-26 | 2018-11-29 | 10X Genomics, Inc. | Single cell analysis of transposase accessible chromatin |
| CN111051523B (zh) | 2017-11-15 | 2024-03-19 | 10X基因组学有限公司 | 功能化凝胶珠 |
| US10829815B2 (en) | 2017-11-17 | 2020-11-10 | 10X Genomics, Inc. | Methods and systems for associating physical and genetic properties of biological particles |
| SG11202007686VA (en) | 2018-02-12 | 2020-09-29 | 10X Genomics Inc | Methods characterizing multiple analytes from individual cells or cell populations |
| SG11202009889VA (en) | 2018-04-06 | 2020-11-27 | 10X Genomics Inc | Systems and methods for quality control in single cell processing |
| WO2019200326A1 (en) | 2018-04-13 | 2019-10-17 | Rarecyte, Inc. | Kits for labeling of biomarkers and methods of using the same |
| WO2019217758A1 (en) | 2018-05-10 | 2019-11-14 | 10X Genomics, Inc. | Methods and systems for molecular library generation |
| EP3898666A2 (en) | 2018-12-17 | 2021-10-27 | Immudex ApS | Panel comprising borrelia mhc multimers |
| AU2021213439B2 (en) | 2020-01-31 | 2023-01-05 | Cell.Copedia GmbH | Methods of isolating a biological entity |
| US12449419B1 (en) | 2020-02-12 | 2025-10-21 | 10X Genomics, Inc. | Methods for detecting binding of peptide-MHC monomers to T cells |
| CN111965341B (zh) * | 2020-08-10 | 2023-04-11 | 武汉菲恩生物科技有限公司 | 一种基于葡聚糖的HRP-羊抗鼠IgG标记抗体及其制备方法 |
| WO2022033975A1 (en) | 2020-08-10 | 2022-02-17 | Innate Pharma | Cell surface mica and micb detection using antibodies |
| CN117242093A (zh) | 2021-04-05 | 2023-12-15 | 先天制药公司 | 免疫组织化学方法和kir3dl2特异性试剂 |
| CN115537410A (zh) * | 2022-09-27 | 2022-12-30 | 凯莱英医药化学（阜新）技术有限公司 | 酶固定化载体及其制备方法、固定化酶及其制备方法和应用 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2712344C2 (de) * | 1977-03-21 | 1982-09-23 | Hans Dr. 4803 Steinhagen Bünemann | Löslicher Komplexbildner für die affinitätsspezifische Trennung von Nukleinsäuren |
| SE7812237L (sv) * | 1978-11-28 | 1980-05-29 | Pharmacia Diagnostics Ab | Koncentrationsbestemning av substanser med formaga att biospecifikt binda molekyler med biologiskt ursprung |
| FR2453847B1 (fr) * | 1979-04-13 | 1985-08-16 | Anvar | Procede pour l'obtention d'ampholytes porteurs utilisables dans les diverses techniques d'electrofocalisation |
| US4752339A (en) * | 1983-10-31 | 1988-06-21 | Hi-Tek Polymers, Inc. | Thixotropic aqueous solutions containing a divinylsulfone-crosslinked polygalactomannan gum |
| US4780409A (en) * | 1985-05-02 | 1988-10-25 | Genetic Systems Corporation | Thermally induced phase separation immunoassay |
| US4778751A (en) * | 1986-05-12 | 1988-10-18 | Diagnostic Products Corporation | Method for measuring antigens or antibodies in biological fluids using ligand labeled antigens or ligand labeled antibodies |
| CA1304682C (en) * | 1986-11-19 | 1992-07-07 | Nobuo Monji | Membrane affinity concentration immunoassay |
| AU609241B2 (en) * | 1988-01-29 | 1991-04-26 | Abbott Laboratories | Ion-capture assays and devices |
| CA1341592C (en) * | 1989-07-07 | 2009-04-14 | Abbott Laboratories | Ion capture reagents and methods for performing binding assays |
-
1992
- 1992-06-29 ES ES92916161T patent/ES2094920T3/es not_active Expired - Lifetime
- 1992-06-29 EP EP92916161A patent/EP0594772B1/en not_active Expired - Lifetime
- 1992-06-29 CA CA002112992A patent/CA2112992C/en not_active Expired - Lifetime
- 1992-06-29 AT AT92916161T patent/ATE142021T1/de active
- 1992-06-29 DE DE69213240T patent/DE69213240T2/de not_active Expired - Lifetime
- 1992-06-29 JP JP50189993A patent/JP3340434B2/ja not_active Expired - Lifetime
- 1992-06-29 DK DK92916161.0T patent/DK0594772T3/da active
- 1992-06-29 AU AU23489/92A patent/AU667051B2/en not_active Expired
- 1992-06-29 WO PCT/DK1992/000206 patent/WO1993001498A1/en not_active Ceased
-
1994
- 1994-01-04 FI FI940023A patent/FI115413B/fi not_active IP Right Cessation
- 1994-01-04 NO NO19940030A patent/NO315443B1/no not_active IP Right Cessation
-
1996
- 1996-11-28 GR GR960403197T patent/GR3021806T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO940030L (no) | 1994-03-03 |
| CA2112992C (en) | 2002-06-11 |
| CA2112992A1 (en) | 1993-01-21 |
| DK0594772T3 (enExample) | 1997-02-24 |
| NO315443B1 (no) | 2003-09-01 |
| JPH06509167A (ja) | 1994-10-13 |
| GR3021806T3 (en) | 1997-02-28 |
| DE69213240T2 (de) | 1997-04-24 |
| WO1993001498A1 (en) | 1993-01-21 |
| NO940030D0 (no) | 1994-01-04 |
| FI940023A7 (fi) | 1994-02-25 |
| EP0594772B1 (en) | 1996-08-28 |
| EP0594772A1 (en) | 1994-05-04 |
| ES2094920T3 (es) | 1997-02-01 |
| DE69213240D1 (de) | 1996-10-02 |
| AU2348992A (en) | 1993-02-11 |
| FI940023A0 (fi) | 1994-01-04 |
| JP3340434B2 (ja) | 2002-11-05 |
| AU667051B2 (en) | 1996-03-07 |
| ATE142021T1 (de) | 1996-09-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FI115413B (fi) | Vesiliukoisia, polymeeripohjaisia reagensseja ja konjugaatteja, jotka sisältävät divinyylisulfonista johdettuja ryhmiä | |
| US5543332A (en) | Water-soluble, polymer-based reagents and conjugates comprising moieties derived from divinyl sulfone | |
| Nakane et al. | Peroxidase-labeled antibody a new method of conjugation | |
| US4959306A (en) | Labeling design for a binding assay reagent | |
| CA2336564C (en) | Method for preparing water-soluble cross-linked conjugates | |
| Yoshitake et al. | Mild and efficient conjugation of rabbit Fab'and horseradish peroxidase using a maleimide compound and its use for enzyme immunoassay | |
| US4780421A (en) | Cleavable labels for use in binding assays | |
| US5561049A (en) | Method for detecting antibodies | |
| JP2858534B2 (ja) | 変性タンパク質に対するモノクローナル抗体 | |
| CN111417856B (zh) | 抑制靶干扰作用的抗药物抗体测定法 | |
| CA2193323C (en) | Process for preparing a synthetic calibrator for use in sandwich immunoassays, which calibrator consists of an antibody against one of the antibodies used in the assay and of a sequence of the analyte | |
| US4975532A (en) | Method to derivatize dextran | |
| US4649105A (en) | Method of measuring biological ligand | |
| IE902389A1 (en) | Enzymatically binding bioactive materials to proteins | |
| JP3260379B2 (ja) | 西洋ワサビペルオキシダーゼを用いて生体分子を標識する方法 | |
| US5856106A (en) | Determination of antibody production against administered therapeutic glycoproteins, especially monoclonal antibodies | |
| US5128241A (en) | Microcapsule immunoassay and reagents therefor | |
| JPH0731191B2 (ja) | チログロブリンを使用する甲状腺ホルモンの免疫定量法 | |
| CA1122119A (en) | Process for the determination of the thyroxine- binding index in serum | |
| Gadkari et al. | Enzyme-antibody conjugation by a heterobifunctional reagent and its application in enzyme-linked immunosorbent assay (ELISA) for the detection of hepatitis B surface antigen | |
| Wood et al. | Solid-phase luminescence immunoassays using kinase and aryl hydrazide labels | |
| JPH06181762A (ja) | 標識抗体組成物 | |
| CN119246855A (zh) | 一种检测尿液中梅毒螺旋体抗体的试剂盒及其制备方法 | |
| JPH1123574A (ja) | 生理活性物質に酵素を結合する方法 | |
| Nowotny | Preparation of Peroxidase-Labeled Antibody |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG | Patent granted |
Ref document number: 115413 Country of ref document: FI |
|
| PC | Transfer of assignment of patent |
Owner name: DAKO DENMARK A/S Free format text: DAKO DENMARK A/S |
|
| MA | Patent expired |