DE69213240T2 - Wasserlösliche reagenzien und konjugate auf polymerbasis, die vom divinylsulfon abgeleitete reste enthalten - Google Patents
Wasserlösliche reagenzien und konjugate auf polymerbasis, die vom divinylsulfon abgeleitete reste enthaltenInfo
- Publication number
- DE69213240T2 DE69213240T2 DE69213240T DE69213240T DE69213240T2 DE 69213240 T2 DE69213240 T2 DE 69213240T2 DE 69213240 T DE69213240 T DE 69213240T DE 69213240 T DE69213240 T DE 69213240T DE 69213240 T2 DE69213240 T2 DE 69213240T2
- Authority
- DE
- Germany
- Prior art keywords
- dextran
- water
- soluble
- conjugate
- molecular species
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 title claims abstract description 106
- 239000003153 chemical reaction reagent Substances 0.000 title claims abstract description 100
- 229920002307 Dextran Polymers 0.000 claims abstract description 339
- 238000000034 method Methods 0.000 claims abstract description 185
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 93
- 238000006243 chemical reaction Methods 0.000 claims abstract description 64
- 239000000523 sample Substances 0.000 claims abstract description 60
- 239000000427 antigen Substances 0.000 claims abstract description 46
- 108091007433 antigens Proteins 0.000 claims abstract description 46
- 102000036639 antigens Human genes 0.000 claims abstract description 46
- 108090000623 proteins and genes Proteins 0.000 claims abstract description 42
- 239000000126 substance Substances 0.000 claims abstract description 35
- 102000004190 Enzymes Human genes 0.000 claims abstract description 29
- 108090000790 Enzymes Proteins 0.000 claims abstract description 29
- 125000005647 linker group Chemical group 0.000 claims abstract description 25
- 238000009396 hybridization Methods 0.000 claims abstract description 22
- 125000000524 functional group Chemical group 0.000 claims abstract description 20
- 229920001282 polysaccharide Polymers 0.000 claims abstract description 15
- 239000005017 polysaccharide Substances 0.000 claims abstract description 15
- 238000000746 purification Methods 0.000 claims abstract description 10
- 239000000975 dye Substances 0.000 claims abstract description 7
- 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 141
- 108020004774 Alkaline Phosphatase Proteins 0.000 claims description 141
- 241000894007 species Species 0.000 claims description 139
- 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 86
- 108010001336 Horseradish Peroxidase Proteins 0.000 claims description 75
- 238000002965 ELISA Methods 0.000 claims description 58
- 229960002685 biotin Drugs 0.000 claims description 43
- 235000020958 biotin Nutrition 0.000 claims description 43
- 239000011616 biotin Substances 0.000 claims description 43
- 108090001008 Avidin Proteins 0.000 claims description 36
- 108010090804 Streptavidin Proteins 0.000 claims description 36
- 235000018102 proteins Nutrition 0.000 claims description 36
- 102000004169 proteins and genes Human genes 0.000 claims description 36
- 239000007864 aqueous solution Substances 0.000 claims description 34
- 230000000984 immunochemical effect Effects 0.000 claims description 31
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 29
- 230000008569 process Effects 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 22
- 238000003556 assay Methods 0.000 claims description 20
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 claims description 17
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 claims description 17
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 16
- 229920001184 polypeptide Polymers 0.000 claims description 15
- 230000002535 lyotropic effect Effects 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 230000000295 complement effect Effects 0.000 claims description 13
- 235000013828 hydroxypropyl starch Nutrition 0.000 claims description 13
- NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical compound OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 claims description 11
- 239000000463 material Substances 0.000 claims description 11
- 239000012528 membrane Substances 0.000 claims description 11
- 238000003018 immunoassay Methods 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 150000001413 amino acids Chemical class 0.000 claims description 7
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 6
- 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
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 6
- 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 6
- 229910019142 PO4 Inorganic materials 0.000 claims description 6
- 230000000093 cytochemical effect Effects 0.000 claims description 6
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 6
- 230000000269 nucleophilic effect Effects 0.000 claims description 6
- 229960003330 pentetic acid Drugs 0.000 claims description 6
- 235000021317 phosphate Nutrition 0.000 claims description 6
- 230000002285 radioactive effect Effects 0.000 claims description 6
- 238000003127 radioimmunoassay Methods 0.000 claims description 6
- 229920000936 Agarose Polymers 0.000 claims description 5
- 230000003993 interaction Effects 0.000 claims description 5
- 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
- 238000002105 Southern blotting Methods 0.000 claims description 4
- 229920002472 Starch Polymers 0.000 claims description 4
- 108010046334 Urease Proteins 0.000 claims description 4
- 229920002678 cellulose Polymers 0.000 claims description 4
- 239000001913 cellulose Substances 0.000 claims description 4
- 235000010980 cellulose Nutrition 0.000 claims description 4
- 230000002255 enzymatic effect Effects 0.000 claims description 4
- 235000019420 glucose oxidase Nutrition 0.000 claims description 4
- 229940096919 glycogen Drugs 0.000 claims description 4
- 238000012151 immunohistochemical method Methods 0.000 claims description 4
- 229920001206 natural gum Polymers 0.000 claims description 4
- 229920001223 polyethylene glycol Polymers 0.000 claims description 4
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 4
- 235000019422 polyvinyl alcohol Nutrition 0.000 claims description 4
- 235000019698 starch Nutrition 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
- 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 3
- 238000000636 Northern blotting Methods 0.000 claims description 3
- 150000001720 carbohydrates Chemical class 0.000 claims description 3
- 235000014633 carbohydrates Nutrition 0.000 claims description 3
- 238000007901 in situ hybridization Methods 0.000 claims description 3
- 150000002772 monosaccharides Chemical class 0.000 claims description 3
- 150000002482 oligosaccharides Polymers 0.000 claims description 3
- 229920000058 polyacrylate Polymers 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
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 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
- 108090001090 Lectins Proteins 0.000 claims description 2
- 102000004856 Lectins Human genes 0.000 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- 108091034117 Oligonucleotide Proteins 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 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
- 239000003102 growth factor Substances 0.000 claims description 2
- 239000002523 lectin Substances 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 150000003013 phosphoric acid derivatives Chemical class 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
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 2
- 150000003892 tartrate salts Chemical class 0.000 claims description 2
- 229920001612 Hydroxyethyl starch Polymers 0.000 claims 3
- 229910052751 metal Inorganic materials 0.000 claims 2
- 239000002184 metal Substances 0.000 claims 2
- 238000001514 detection method Methods 0.000 abstract description 31
- 229940088598 enzyme Drugs 0.000 abstract description 27
- 238000002360 preparation method Methods 0.000 abstract description 27
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 7
- 125000003396 thiol group Chemical group [H]S* 0.000 abstract description 7
- 238000003364 immunohistochemistry Methods 0.000 abstract description 4
- 230000021615 conjugation Effects 0.000 abstract description 2
- 238000011002 quantification Methods 0.000 abstract description 2
- 238000000926 separation method Methods 0.000 abstract description 2
- 238000012360 testing method Methods 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 209
- 238000005859 coupling reaction Methods 0.000 description 181
- 230000008878 coupling Effects 0.000 description 179
- 238000010168 coupling process Methods 0.000 description 179
- 241000283973 Oryctolagus cuniculus Species 0.000 description 88
- 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 77
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 75
- 241000283707 Capra Species 0.000 description 57
- 241000699666 Mus <mouse, genus> Species 0.000 description 55
- 238000002523 gelfiltration Methods 0.000 description 52
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 46
- 229920000642 polymer Polymers 0.000 description 44
- 238000002835 absorbance Methods 0.000 description 38
- 108060003951 Immunoglobulin Proteins 0.000 description 33
- 102000018358 immunoglobulin Human genes 0.000 description 33
- 239000012506 Sephacryl® Substances 0.000 description 32
- 238000011534 incubation Methods 0.000 description 30
- 230000004913 activation Effects 0.000 description 29
- 239000003550 marker Substances 0.000 description 29
- 240000003291 Armoracia rusticana Species 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 238000013459 approach Methods 0.000 description 24
- 239000011780 sodium chloride Substances 0.000 description 23
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 20
- 229940072221 immunoglobulins Drugs 0.000 description 20
- 238000009739 binding Methods 0.000 description 19
- 239000012634 fragment Substances 0.000 description 19
- 238000003756 stirring Methods 0.000 description 19
- 230000027455 binding Effects 0.000 description 18
- 239000000203 mixture Substances 0.000 description 18
- 230000001965 increasing effect Effects 0.000 description 17
- 230000035945 sensitivity Effects 0.000 description 15
- 238000005406 washing 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
- -1 dextrans Chemical class 0.000 description 14
- 229920001213 Polysorbate 20 Polymers 0.000 description 12
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 12
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 12
- 239000012279 sodium borohydride Substances 0.000 description 12
- 229910000033 sodium borohydride Inorganic materials 0.000 description 12
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 11
- 238000000502 dialysis Methods 0.000 description 11
- 150000004804 polysaccharides Chemical class 0.000 description 11
- 239000004471 Glycine Substances 0.000 description 10
- 102000003992 Peroxidases Human genes 0.000 description 10
- 239000000872 buffer Substances 0.000 description 10
- 230000009918 complex formation Effects 0.000 description 10
- 238000011161 development Methods 0.000 description 10
- 230000018109 developmental process Effects 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
- 239000011541 reaction mixture Substances 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- 239000000969 carrier Substances 0.000 description 9
- 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 9
- 239000000499 gel Substances 0.000 description 9
- 239000001341 hydroxy propyl starch Substances 0.000 description 9
- 238000001556 precipitation Methods 0.000 description 9
- 230000009257 reactivity Effects 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
- 229920002684 Sepharose Polymers 0.000 description 8
- 108010074605 gamma-Globulins Proteins 0.000 description 8
- 230000001900 immune effect Effects 0.000 description 8
- 108040007629 peroxidase activity proteins Proteins 0.000 description 8
- 239000000020 Nitrocellulose Substances 0.000 description 7
- 230000000890 antigenic effect Effects 0.000 description 7
- 230000000903 blocking effect Effects 0.000 description 7
- 229940098773 bovine serum albumin Drugs 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 229920001220 nitrocellulos Polymers 0.000 description 7
- 239000000047 product Substances 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
- 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 6
- 230000002055 immunohistochemical effect Effects 0.000 description 6
- 150000007523 nucleic acids Chemical class 0.000 description 6
- 239000008363 phosphate buffer Substances 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- 210000001519 tissue Anatomy 0.000 description 6
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 5
- 108020004414 DNA Proteins 0.000 description 5
- 108010072866 Prostate-Specific Antigen Proteins 0.000 description 5
- 102100038358 Prostate-specific antigen Human genes 0.000 description 5
- 239000007983 Tris buffer Substances 0.000 description 5
- 235000001014 amino acid Nutrition 0.000 description 5
- 239000010931 gold Substances 0.000 description 5
- 238000003119 immunoblot Methods 0.000 description 5
- 238000002991 immunohistochemical analysis Methods 0.000 description 5
- 229920000656 polylysine Polymers 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 238000001179 sorption measurement Methods 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 5
- 229920003169 water-soluble polymer Polymers 0.000 description 5
- 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
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- 108010039918 Polylysine Proteins 0.000 description 4
- 241000282898 Sus scrofa Species 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
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000004132 cross linking Methods 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
- 239000003517 fume Substances 0.000 description 4
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 4
- 229910052737 gold Inorganic materials 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 108020004707 nucleic acids Proteins 0.000 description 4
- 102000039446 nucleic acids Human genes 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- 229920000136 polysorbate Polymers 0.000 description 4
- 239000007790 solid phase Substances 0.000 description 4
- 238000007447 staining method 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
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- 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 3
- 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
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 3
- 229920005654 Sephadex Polymers 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
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000001718 carbodiimides Chemical class 0.000 description 3
- 239000002738 chelating agent Substances 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
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 229910052747 lanthanoid Inorganic materials 0.000 description 3
- 150000002602 lanthanoids Chemical class 0.000 description 3
- 238000011068 loading method Methods 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
- 239000000376 reactant Substances 0.000 description 3
- 229910052709 silver Inorganic materials 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
- 238000001262 western blot Methods 0.000 description 3
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 2
- 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
- QCVGEOXPDFCNHA-UHFFFAOYSA-N 5,5-dimethyl-2,4-dioxo-1,3-oxazolidine-3-carboxamide Chemical compound CC1(C)OC(=O)N(C(N)=O)C1=O QCVGEOXPDFCNHA-UHFFFAOYSA-N 0.000 description 2
- 235000011330 Armoracia rusticana Nutrition 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 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
- 108091028043 Nucleic acid sequence Proteins 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
- 102000004160 Phosphoric Monoester Hydrolases Human genes 0.000 description 2
- 108090000608 Phosphoric Monoester Hydrolases 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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 2
- 230000003213 activating effect Effects 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 210000004899 c-terminal region Anatomy 0.000 description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 210000000991 chicken egg Anatomy 0.000 description 2
- 238000004587 chromatography analysis Methods 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
- 229910000396 dipotassium phosphate Inorganic materials 0.000 description 2
- 235000019797 dipotassium phosphate Nutrition 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 235000014103 egg white Nutrition 0.000 description 2
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000007850 fluorescent dye Substances 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 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
- 238000002372 labelling Methods 0.000 description 2
- 230000002045 lasting effect Effects 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
- 229910001629 magnesium chloride Inorganic materials 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 230000009871 nonspecific binding Effects 0.000 description 2
- 210000002741 palatine tonsil Anatomy 0.000 description 2
- 230000035515 penetration 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
- 229910000160 potassium phosphate Inorganic materials 0.000 description 2
- 235000011009 potassium phosphates Nutrition 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 210000002307 prostate Anatomy 0.000 description 2
- 230000007420 reactivation Effects 0.000 description 2
- 239000012070 reactive reagent Substances 0.000 description 2
- 238000010079 rubber tapping Methods 0.000 description 2
- 238000005185 salting out Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 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
- 238000010186 staining Methods 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 2
- 239000011534 wash buffer Substances 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 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
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-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
- 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
- 102000009027 Albumins Human genes 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- 229920000856 Amylose Polymers 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- 229920001661 Chitosan Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
- 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
- 241000522182 Dialium Species 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 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
- 229920002907 Guar gum Polymers 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
- 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
- 229920000881 Modified starch Polymers 0.000 description 1
- YXOLAZRVSSWPPT-UHFFFAOYSA-N Morin Chemical compound OC1=CC(O)=CC=C1C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1 YXOLAZRVSSWPPT-UHFFFAOYSA-N 0.000 description 1
- 241001529936 Murinae Species 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 102000004316 Oxidoreductases Human genes 0.000 description 1
- 108090000854 Oxidoreductases Proteins 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
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229920002873 Polyethylenimine Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 239000013614 RNA sample 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
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 108010034949 Thyroglobulin Proteins 0.000 description 1
- 102000009843 Thyroglobulin Human genes 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
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-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
- 238000010521 absorption reaction Methods 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 238000002479 acid--base titration Methods 0.000 description 1
- 229920006322 acrylamide copolymer Polymers 0.000 description 1
- 239000007825 activation reagent Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000001042 affinity chromatography Methods 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 239000000783 alginic acid Substances 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
- 230000003321 amplification Effects 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
- 239000012298 atmosphere Substances 0.000 description 1
- 238000000376 autoradiography Methods 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- 230000001588 bifunctional effect Effects 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
- 210000001124 body fluid Anatomy 0.000 description 1
- 239000010839 body fluid Substances 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
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 238000012512 characterization method Methods 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
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 239000012501 chromatography medium Substances 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 239000000470 constituent Substances 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
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000002242 deionisation method Methods 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- 239000013024 dilution buffer Substances 0.000 description 1
- 150000002009 diols Chemical group 0.000 description 1
- 239000012738 dissolution medium Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- YQGOJNYOYNNSMM-UHFFFAOYSA-N eosin Chemical compound [Na+].OC(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C(O)=C(Br)C=C21 YQGOJNYOYNNSMM-UHFFFAOYSA-N 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
- 229940011411 erythrosine Drugs 0.000 description 1
- 235000012732 erythrosine Nutrition 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
- 230000005284 excitation Effects 0.000 description 1
- 238000002474 experimental method Methods 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
- 230000009395 genetic defect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000000665 guar gum Substances 0.000 description 1
- 235000010417 guar gum Nutrition 0.000 description 1
- 229960002154 guar gum Drugs 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 239000013628 high molecular weight specie Substances 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
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 239000012678 infectious agent Substances 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
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000013627 low molecular weight specie Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- 235000007708 morin Nutrition 0.000 description 1
- UXOUKMQIEVGVLY-UHFFFAOYSA-N morin Natural products OC1=CC(O)=CC(C2=C(C(=O)C3=C(O)C=C(O)C=C3O2)O)=C1 UXOUKMQIEVGVLY-UHFFFAOYSA-N 0.000 description 1
- 229940126619 mouse monoclonal antibody Drugs 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- VIKNJXKGJWUCNN-XGXHKTLJSA-N norethisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-N 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 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
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 229940111202 pepsin Drugs 0.000 description 1
- 238000005897 peptide coupling reaction Methods 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
- 229920000768 polyamine Polymers 0.000 description 1
- 229920002704 polyhistidine Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000307 polymer substrate Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920002714 polyornithine Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 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
- 238000012205 qualitative assay Methods 0.000 description 1
- 238000012207 quantitative assay Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000011160 research 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
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000002798 spectrophotometry method Methods 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
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 230000008685 targeting Effects 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
- 125000000341 threoninyl group Chemical group [H]OC([H])(C([H])([H])[H])C([H])(N([H])[H])C(*)=O 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
- 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)
- Microbiology (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)
- Peptides Or Proteins (AREA)
- Cephalosporin Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK911309A DK130991D0 (da) | 1991-07-04 | 1991-07-04 | Polymere konjugater |
| 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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69213240D1 DE69213240D1 (de) | 1996-10-02 |
| DE69213240T2 true DE69213240T2 (de) | 1997-04-24 |
Family
ID=26065568
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69213240T Expired - Lifetime DE69213240T2 (de) | 1991-07-04 | 1992-06-29 | Wasserlösliche reagenzien und konjugate auf polymerbasis, die vom divinylsulfon abgeleitete reste enthalten |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP0594772B1 (https=) |
| JP (1) | JP3340434B2 (https=) |
| AT (1) | ATE142021T1 (https=) |
| AU (1) | AU667051B2 (https=) |
| CA (1) | CA2112992C (https=) |
| DE (1) | DE69213240T2 (https=) |
| DK (1) | DK0594772T3 (https=) |
| ES (1) | ES2094920T3 (https=) |
| FI (1) | FI115413B (https=) |
| GR (1) | GR3021806T3 (https=) |
| NO (1) | NO315443B1 (https=) |
| WO (1) | WO1993001498A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10039112A1 (de) * | 2000-08-07 | 2002-03-07 | Pe Diagnostik Gmbh | Verfahren zum Herstellen von Antikörper aus einer verunreinigten Antigenlösung |
Families Citing this family (85)
| 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 |
| JPH10500310A (ja) * | 1994-05-19 | 1998-01-13 | ダコ アクティーゼルスカブ | 淋菌及びトラコーマ クラミジアの検出のためのｐｎａ プローブ |
| 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 |
| WO1998024463A2 (en) | 1996-12-06 | 1998-06-11 | 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 |
| PT1101115E (pt) * | 1998-07-30 | 2004-09-30 | Oakville Trading Hong Kong Ltd | Metodo para preparar conjugados reticulados soluveis em agua |
| 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 |
| GB0029617D0 (en) * | 2000-12-05 | 2001-01-17 | Norchip As | Ligand detection method |
| DK2336167T3 (da) | 2001-03-14 | 2019-09-02 | Dako Denmark As | MHC-molekylkonstrukter og deres anvendelse til diagnose og terapi |
| US7034127B2 (en) * | 2002-07-02 | 2006-04-25 | Genzyme Corporation | Hydrophilic biopolymer-drug conjugates, their preparation and use |
| 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 |
| 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 |
| WO2005062048A1 (de) * | 2003-12-01 | 2005-07-07 | Dade Behring Marburg Gmbh | Homogenes nachweisverfahren |
| EP1692515A1 (de) * | 2003-12-01 | 2006-08-23 | Dade Behring Marburg GmbH | Konjugate und deren verwendung in nachweisverfahren |
| JP4949038B2 (ja) | 2003-12-01 | 2012-06-06 | ダコ デンマーク アクティーゼルスカブ | 免疫組織化学的検出のための方法および組成物 |
| GB0426822D0 (en) | 2004-12-07 | 2005-01-12 | Precisense As | Sensor for detection of glucose |
| GB0426823D0 (en) | 2004-12-07 | 2005-01-12 | Precisense As | Sensor for detection of glucose |
| NZ564222A (en) | 2005-06-14 | 2011-10-28 | Taigen Biotechnology Co Ltd | Pyrimidine compounds |
| US8193206B2 (en) | 2005-06-14 | 2012-06-05 | Taigen Biotechnology Co., Ltd. | Pyrimidine compounds |
| DE112006003813T5 (de) | 2006-03-20 | 2009-01-22 | Inverness Medical Switzerland Gmbh | Wasserlösliche Konjugate zur elektrochemischen Detektion |
| WO2008116468A2 (en) * | 2007-03-26 | 2008-10-02 | 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 |
| DK2268635T3 (en) | 2008-04-21 | 2015-09-14 | Taigen Biotechnology Co Ltd | Heterocyclic Compounds |
| WO2010009735A2 (en) | 2008-07-23 | 2010-01-28 | Dako Denmark A/S | Combinatorial analysis and repair |
| DK2334703T3 (en) | 2008-09-17 | 2015-10-05 | Innate Pharma | Configurations and methods for detection of 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 |
| US11992518B2 (en) | 2008-10-02 | 2024-05-28 | Agilent Technologies, Inc. | Molecular vaccines for infectious disease |
| WO2010037402A1 (en) | 2008-10-02 | 2010-04-08 | Dako Denmark A/S | 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 |
| EP2494073B1 (de) | 2009-10-26 | 2017-11-29 | AGCT GmbH | Konjugate von nukleotiden und methoden zu deren anwendung |
| 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 |
| US9951386B2 (en) | 2014-06-26 | 2018-04-24 | 10X Genomics, Inc. | Methods and systems for processing polynucleotides |
| US9701998B2 (en) | 2012-12-14 | 2017-07-11 | 10X Genomics, Inc. | Methods and systems for processing polynucleotides |
| AU2013302756C1 (en) | 2012-08-14 | 2018-05-17 | 10X Genomics, Inc. | Microcapsule compositions and methods |
| US10323279B2 (en) | 2012-08-14 | 2019-06-18 | 10X Genomics, Inc. | Methods and systems for processing polynucleotides |
| US10752949B2 (en) | 2012-08-14 | 2020-08-25 | 10X Genomics, Inc. | Methods and systems for processing polynucleotides |
| US10584381B2 (en) | 2012-08-14 | 2020-03-10 | 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 |
| KR20200140929A (ko) | 2013-02-08 | 2020-12-16 | 10엑스 제노믹스, 인크. | 폴리뉴클레오티드 바코드 생성 |
| JP6353446B2 (ja) | 2013-06-28 | 2018-07-04 | 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 |
| BR112016023625A2 (pt) | 2014-04-10 | 2018-06-26 | 10X Genomics, Inc. | dispositivos fluídicos, sistemas e métodos para encapsular e particionar reagentes, e aplicações dos mesmos |
| WO2015188839A2 (en) | 2014-06-13 | 2015-12-17 | Immudex Aps | General detection and isolation of specific cells by binding of labeled molecules |
| US12312640B2 (en) | 2014-06-26 | 2025-05-27 | 10X Genomics, Inc. | Analysis of nucleic acid sequences |
| CA2953469A1 (en) | 2014-06-26 | 2015-12-30 | 10X Genomics, Inc. | Analysis of nucleic acid sequences |
| WO2015200893A2 (en) | 2014-06-26 | 2015-12-30 | 10X Genomics, Inc. | Methods of analyzing nucleic acids from individual cells or cell populations |
| JP6769969B2 (ja) | 2015-01-12 | 2020-10-14 | １０エックス ジェノミクス， インコーポレイテッド | 核酸配列決定ライブラリーを作製するためのプロセス及びシステム、並びにこれらを使用して作製したライブラリー |
| EP3262407B1 (en) | 2015-02-24 | 2023-08-30 | 10X Genomics, Inc. | Partition processing methods and systems |
| JP6954899B2 (ja) | 2015-12-04 | 2021-10-27 | １０エックス ゲノミクス，インコーポレイテッド | 核酸の解析のための方法及び組成物 |
| CA3017412A1 (en) | 2016-03-15 | 2017-09-21 | Mipsalus Aps | A method for qualitative or quantitative determination of the presence of an analyte in a sample |
| US10815525B2 (en) | 2016-12-22 | 2020-10-27 | 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 |
| US10011872B1 (en) | 2016-12-22 | 2018-07-03 | 10X Genomics, Inc. | Methods and systems for processing polynucleotides |
| EP4029939B1 (en) | 2017-01-30 | 2023-06-28 | 10X Genomics, Inc. | Methods and systems for droplet-based single cell barcoding |
| US10400235B2 (en) | 2017-05-26 | 2019-09-03 | 10X Genomics, Inc. | Single cell analysis of transposase accessible chromatin |
| EP3445876B1 (en) | 2017-05-26 | 2023-07-05 | 10X Genomics, Inc. | Single cell analysis of transposase accessible chromatin |
| SG11201913654QA (en) | 2017-11-15 | 2020-01-30 | 10X Genomics Inc | Functionalized gel beads |
| 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 |
| CN112262218B (zh) | 2018-04-06 | 2024-11-08 | 10X基因组学有限公司 | 用于单细胞处理中的质量控制的系统和方法 |
| 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 |
| WO2020127222A2 (en) | 2018-12-17 | 2020-06-25 | Immudex Aps | Panel comprising borrelia mhc multimers |
| WO2021152178A1 (en) | 2020-01-31 | 2021-08-05 | 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 |
| CA3186062A1 (en) | 2020-08-10 | 2022-02-17 | Marion BENEZECH | Cell surface mica and micb detection using antibodies |
| 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 |
| KR20230165913A (ko) | 2021-04-05 | 2023-12-05 | 이나뜨 파르마 에스.에이. | 면역조직화학 방법 및 kir3dl2-특이적 시약 |
| 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 DK DK92916161.0T patent/DK0594772T3/da active
- 1992-06-29 WO PCT/DK1992/000206 patent/WO1993001498A1/en not_active Ceased
- 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 EP EP92916161A patent/EP0594772B1/en not_active Expired - Lifetime
- 1992-06-29 JP JP50189993A patent/JP3340434B2/ja not_active Expired - Lifetime
- 1992-06-29 AU AU23489/92A patent/AU667051B2/en not_active Expired
- 1992-06-29 ES ES92916161T patent/ES2094920T3/es not_active Expired - Lifetime
-
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
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10039112A1 (de) * | 2000-08-07 | 2002-03-07 | Pe Diagnostik Gmbh | Verfahren zum Herstellen von Antikörper aus einer verunreinigten Antigenlösung |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3340434B2 (ja) | 2002-11-05 |
| FI940023A7 (fi) | 1994-02-25 |
| NO940030D0 (no) | 1994-01-04 |
| GR3021806T3 (en) | 1997-02-28 |
| CA2112992C (en) | 2002-06-11 |
| ES2094920T3 (es) | 1997-02-01 |
| EP0594772A1 (en) | 1994-05-04 |
| FI115413B (fi) | 2005-04-29 |
| DE69213240D1 (de) | 1996-10-02 |
| NO940030L (no) | 1994-03-03 |
| EP0594772B1 (en) | 1996-08-28 |
| ATE142021T1 (de) | 1996-09-15 |
| AU2348992A (en) | 1993-02-11 |
| DK0594772T3 (https=) | 1997-02-24 |
| FI940023A0 (fi) | 1994-01-04 |
| NO315443B1 (no) | 2003-09-01 |
| WO1993001498A1 (en) | 1993-01-21 |
| JPH06509167A (ja) | 1994-10-13 |
| AU667051B2 (en) | 1996-03-07 |
| CA2112992A1 (en) | 1993-01-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69213240T2 (de) | Wasserlösliche reagenzien und konjugate auf polymerbasis, die vom divinylsulfon abgeleitete reste enthalten | |
| US5543332A (en) | Water-soluble, polymer-based reagents and conjugates comprising moieties derived from divinyl sulfone | |
| DE69516007T2 (de) | Verfahren zum nachweiss von antikörpern | |
| DE3382572T2 (de) | Antikoerper-verbindungen. | |
| DE69917908T2 (de) | Verfahren zur Herstellung von wasserlöslichen,vernetzten Konjugaten | |
| DE3783928T2 (de) | Verfahren zur immunoassay. | |
| DE68923800T2 (de) | Vorrichtung und verfahren zur bestimmung eines analyten in einer flüssigen probe mittels folgereaktionen. | |
| DE69903899T2 (de) | Enzym-Antikörper-Komplex und eine Methode zur Herstellung desselben | |
| DE2743444A1 (de) | Immunchemisches messverfahren | |
| DE69930404T2 (de) | Methode zum nachweis von analyten | |
| DE2902400A1 (de) | Verbesserter, spezifischer doppelrezeptor-bindetest fuer einen probenliganden | |
| DE2744835B2 (de) | Immunchemisches Meßverfahren | |
| DE2902677A1 (de) | Unloeslich gemachte proteine und immunoassays unter verwendung dieser proteine | |
| DE69106002T2 (de) | Testverfahren und reagenziensatz dafür. | |
| DE69232801T2 (de) | Abtrennungsverfahren | |
| DE69430523T2 (de) | Herstellung von photoprotein konjugaten und verfahren zu ihrer verwendung | |
| DE69809640T2 (de) | Methode zum Nachweis eines Analyten durch Immunchromatographie | |
| EP0291086B1 (de) | Verfahren zur Bestimmung eines Antikörpers in menschlichen Körperflüssigkeiten | |
| DE112006003813T5 (de) | Wasserlösliche Konjugate zur elektrochemischen Detektion | |
| DE3006709A1 (de) | Homogenes verfahren zur kompetitiven bestimmung von liganden | |
| DE2557419A1 (de) | Reagens zum nachweis von analyt- koerpern | |
| EP0716304A1 (de) | Immunoassays für Haptene und hierfür verwendbare Haptentracer-Antikörper-Komplexe sowie Verfahren zur Herstellung derselben | |
| EP0006998B1 (de) | Verfahren zur Bestimmung des Thyroxin-bindungsindex im Serum und Testkit zur Durchführung des Verfahrens | |
| EP0322813A2 (de) | Verfahren zur Bestimmung einer immunologisch aktiven Substanz | |
| DE69902419T2 (de) | Farbstoff-markierte Proteinkonjugat und Verfahren zu seiner Herstellung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8363 | Opposition against the patent | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: DAKO A/S, GLOSTRUP, DK |
|
| 8327 | Change in the person/name/address of the patent owner |
Owner name: DAKOCYTOMATION DENMARK A/S, GLOSTRUP, DK |
|
| 8327 | Change in the person/name/address of the patent owner |
Owner name: DAKO DENMARK A/S, GLOSTRUP, DK |
|
| R071 | Expiry of right |
Ref document number: 594772 Country of ref document: EP |