CH622099A5 - - Google Patents
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- Publication number
- CH622099A5 CH622099A5 CH665673A CH665673A CH622099A5 CH 622099 A5 CH622099 A5 CH 622099A5 CH 665673 A CH665673 A CH 665673A CH 665673 A CH665673 A CH 665673A CH 622099 A5 CH622099 A5 CH 622099A5
- Authority
- CH
- Switzerland
- Prior art keywords
- hapten
- enzyme
- antibody
- hrp
- enzyme conjugate
- Prior art date
Links
- 102000004190 Enzymes Human genes 0.000 claims description 35
- 108090000790 Enzymes Proteins 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 35
- 238000010168 coupling process Methods 0.000 claims description 26
- 230000008878 coupling Effects 0.000 claims description 25
- 238000005859 coupling reaction Methods 0.000 claims description 25
- 229940011871 estrogen Drugs 0.000 claims description 25
- 239000000262 estrogen Substances 0.000 claims description 25
- 239000000126 substance Substances 0.000 claims description 19
- 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 claims description 18
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 claims description 14
- 230000000694 effects Effects 0.000 claims description 13
- 239000007788 liquid Substances 0.000 claims description 11
- 239000000186 progesterone Substances 0.000 claims description 10
- 229960003387 progesterone Drugs 0.000 claims description 10
- 235000019152 folic acid Nutrition 0.000 claims description 9
- 239000011724 folic acid Substances 0.000 claims description 9
- 241001465754 Metazoa Species 0.000 claims description 6
- OVBPIULPVIDEAO-UHFFFAOYSA-N N-Pteroyl-L-glutaminsaeure Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-UHFFFAOYSA-N 0.000 claims description 5
- 229960000304 folic acid Drugs 0.000 claims description 5
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 229940088598 enzyme Drugs 0.000 description 52
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 18
- 108010001336 Horseradish Peroxidase Proteins 0.000 description 17
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 15
- 229960005309 estradiol Drugs 0.000 description 14
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- 239000000203 mixture Substances 0.000 description 13
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- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 12
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- 238000010790 dilution Methods 0.000 description 8
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- 239000000243 solution Substances 0.000 description 6
- PROQIPRRNZUXQM-UHFFFAOYSA-N (16alpha,17betaOH)-Estra-1,3,5(10)-triene-3,16,17-triol Natural products OC1=CC=C2C3CCC(C)(C(C(O)C4)O)C4C3CCC2=C1 PROQIPRRNZUXQM-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- PROQIPRRNZUXQM-ZXXIGWHRSA-N estriol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H]([C@H](O)C4)O)[C@@H]4[C@@H]3CCC2=C1 PROQIPRRNZUXQM-ZXXIGWHRSA-N 0.000 description 5
- 239000007791 liquid phase Substances 0.000 description 5
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- 108010077055 methylated bovine serum albumin Proteins 0.000 description 5
- 239000008363 phosphate buffer Substances 0.000 description 5
- DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 description 4
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- 125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 238000002835 absorbance Methods 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- -1 carboxy, amino Chemical group 0.000 description 3
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- 238000001514 detection method Methods 0.000 description 3
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- NVKAWKQGWWIWPM-ABEVXSGRSA-N 17-β-hydroxy-5-α-Androstan-3-one Chemical compound C1C(=O)CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CC[C@H]21 NVKAWKQGWWIWPM-ABEVXSGRSA-N 0.000 description 2
- YJPIDPAGJSWWBE-FNIAAEIWSA-N 4-{[(14β,17α)-3-hydroxyestra-1,3,5(10)-trien-17-yl]oxy}-4-oxobutanoic acid Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)OC(=O)CCC(O)=O)[C@@H]4[C@@H]3CCC2=C1 YJPIDPAGJSWWBE-FNIAAEIWSA-N 0.000 description 2
- FTOAOBMCPZCFFF-UHFFFAOYSA-N 5,5-diethylbarbituric acid Chemical compound CCC1(CC)C(=O)NC(=O)NC1=O FTOAOBMCPZCFFF-UHFFFAOYSA-N 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- 229920002307 Dextran Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- 102000004407 Lactalbumin Human genes 0.000 description 2
- 108090000942 Lactalbumin Proteins 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
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- 229920005654 Sephadex Polymers 0.000 description 2
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
- 229960003473 androstanolone Drugs 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229940098773 bovine serum albumin Drugs 0.000 description 2
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
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- 229960000587 glutaral Drugs 0.000 description 2
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- 125000000468 ketone group Chemical group 0.000 description 2
- KBOPZPXVLCULAV-UHFFFAOYSA-N mesalamine Chemical compound NC1=CC=C(O)C(C(O)=O)=C1 KBOPZPXVLCULAV-UHFFFAOYSA-N 0.000 description 2
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- 150000002923 oximes Chemical class 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- 150000003431 steroids Chemical class 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
- IGPOPFXCSGWCLM-AZCAJKTISA-N (8s,9s,13s,14s)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,11,17-triol Chemical class OC1=CC=C2[C@H]3C(O)C[C@](C)(C(CC4)O)[C@@H]4[C@@H]3CCC2=C1 IGPOPFXCSGWCLM-AZCAJKTISA-N 0.000 description 1
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-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
- LZKGFGLOQNSMBS-UHFFFAOYSA-N 4,5,6-trichlorotriazine Chemical class ClC1=NN=NC(Cl)=C1Cl LZKGFGLOQNSMBS-UHFFFAOYSA-N 0.000 description 1
- XZKIHKMTEMTJQX-UHFFFAOYSA-N 4-Nitrophenyl Phosphate Chemical compound OP(O)(=O)OC1=CC=C([N+]([O-])=O)C=C1 XZKIHKMTEMTJQX-UHFFFAOYSA-N 0.000 description 1
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- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 108010053835 Catalase Proteins 0.000 description 1
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- YJPIDPAGJSWWBE-UHFFFAOYSA-N Estradiol hemisuccinate Natural products OC1=CC=C2C3CCC(C)(C(CC4)OC(=O)CCC(O)=O)C4C3CCC2=C1 YJPIDPAGJSWWBE-UHFFFAOYSA-N 0.000 description 1
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- 239000005980 Gibberellic acid Substances 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
- 108010056771 Glucosidases Proteins 0.000 description 1
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- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- 108060003951 Immunoglobulin Proteins 0.000 description 1
- FAIXYKHYOGVFKA-UHFFFAOYSA-N Kinetin Natural products N=1C=NC=2N=CNC=2C=1N(C)C1=CC=CO1 FAIXYKHYOGVFKA-UHFFFAOYSA-N 0.000 description 1
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- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 108700020962 Peroxidase Proteins 0.000 description 1
- 102000004160 Phosphoric Monoester Hydrolases Human genes 0.000 description 1
- 108090000608 Phosphoric Monoester Hydrolases Proteins 0.000 description 1
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- 239000012507 Sephadex™ Substances 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- AUYYCJSJGJYCDS-LBPRGKRZSA-N Thyrolar Chemical compound IC1=CC(C[C@H](N)C(O)=O)=CC(I)=C1OC1=CC=C(O)C(I)=C1 AUYYCJSJGJYCDS-LBPRGKRZSA-N 0.000 description 1
- 108010046334 Urease Proteins 0.000 description 1
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- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000002363 auxin Substances 0.000 description 1
- 229960002319 barbital Drugs 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000001124 body fluid Anatomy 0.000 description 1
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
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- 238000000432 density-gradient centrifugation Methods 0.000 description 1
- 229960005156 digoxin Drugs 0.000 description 1
- LTMHDMANZUZIPE-PUGKRICDSA-N digoxin Chemical compound C1[C@H](O)[C@H](O)[C@@H](C)O[C@H]1O[C@@H]1[C@@H](C)O[C@@H](O[C@@H]2[C@H](O[C@@H](O[C@@H]3C[C@@H]4[C@]([C@@H]5[C@H]([C@]6(CC[C@@H]([C@@]6(C)[C@H](O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)C[C@@H]2O)C)C[C@@H]1O LTMHDMANZUZIPE-PUGKRICDSA-N 0.000 description 1
- LTMHDMANZUZIPE-UHFFFAOYSA-N digoxine Natural products C1C(O)C(O)C(C)OC1OC1C(C)OC(OC2C(OC(OC3CC4C(C5C(C6(CCC(C6(C)C(O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)CC2O)C)CC1O LTMHDMANZUZIPE-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
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- IXORZMNAPKEEDV-UHFFFAOYSA-N gibberellic acid GA3 Natural products OC(=O)C1C2(C3)CC(=C)C3(O)CCC2C2(C=CC3O)C1C3(C)C(=O)O2 IXORZMNAPKEEDV-UHFFFAOYSA-N 0.000 description 1
- IXORZMNAPKEEDV-OBDJNFEBSA-N gibberellin A3 Chemical compound C([C@@]1(O)C(=C)C[C@@]2(C1)[C@H]1C(O)=O)C[C@H]2[C@]2(C=C[C@@H]3O)[C@H]1[C@]3(C)C(=O)O2 IXORZMNAPKEEDV-OBDJNFEBSA-N 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
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- 150000002429 hydrazines Chemical class 0.000 description 1
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 102000018358 immunoglobulin Human genes 0.000 description 1
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- QANMHLXAZMSUEX-UHFFFAOYSA-N kinetin Chemical compound N=1C=NC=2N=CNC=2C=1NCC1=CC=CO1 QANMHLXAZMSUEX-UHFFFAOYSA-N 0.000 description 1
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- 230000002906 microbiologic effect Effects 0.000 description 1
- WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 description 1
- 229960002748 norepinephrine Drugs 0.000 description 1
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- 239000003960 organic solvent Substances 0.000 description 1
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- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 125000001747 pteroyl group Chemical group [H]C1=C([H])C(C(=O)[*])=C([H])C([H])=C1N([H])C([H])([H])C1=C([H])N=C2N([H])C(N([H])[H])=NC(=O)C2=N1 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
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- 239000001384 succinic acid Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 238000010998 test method Methods 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
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 229940035722 triiodothyronine Drugs 0.000 description 1
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- 239000011782 vitamin Substances 0.000 description 1
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- 229940082632 vitamin b12 and folic acid Drugs 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
- G01N33/576—Immunoassay; Biospecific binding assay; Materials therefor for hepatitis
-
- 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
-
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Description
Die Erfindung betrifft ein'Verfahren zur Bestimmung von Haptenen, bei dem man eine flüssige Probe mit vorher bestimmten Mengen Hapten-Enzym-Konjugat und eines Antikörpers für das Hapten und Hapten-Enzym-Konjugat zusammenbringt, das an den Antikörper gebundene Enzym-Konjugat von dem nichtgebundenen Konjugat abtrennt und die Enzymaktivität in einer der beiden Fraktionen misst, das durch gekennzeichnet ist dass man ein Hapten-Enzym-Konjugat verwendet, bei dem sich die Kupplung zwischen dem Enzym und dem Hapten unterscheidet von der Kupplung zwischen Hapten und der hochmolekularen Substanz im Kupplungsprodukt aus dem Hapten und einer hochmolekularen Substanz, das zur Entwicklung des Antikörpers verwendet wurde.
Die Erfindung betrifft auch eine Testpackung zur Durchführung dieses Verfahrens, welche dadurch gekennzeichnet ist, dass sie eine vorher bestimmte Menge eines Hapten-Enzym-Konjugates und eine vorher bestimmte Menge eines Antikörpers für das Hapten und Hapten-Enzym-Konjugat enthält.
In der niederländischen Patentanmeldung 7016 396 ist ein Verfahren zum Nachweis und zur Bestimmung von beispielsweise Haptenen beschrieben, das darin besteht, dass man zu einer Flüssigkeit, z. B. einer Körperflüssigkeit wie Blut oder s Urin, enthaltend eine unbekannte Menge Hapten, eine bestimmte Menge eines Kupplungsproduktes aus einem Enzym und dem entsprechenden Hapten und eine bestimmte Menge Antikörper gegen dieses Hapten in unlöslicher Form zugibt. Nach Zugabe dieser Bestanteile findet eine Konkurrenzreak-io tion zwischen diesen Antikörpern und dem zu bestimmenden Hapten auf der einen Seite und den Antikörper und dem an das Enzym gekuppelten Hapten andererseits statt Je grösser die Menge an freiem Hapten in der Flüssigkeit, um so grösser ist die Menge des Hapten-Enzym-Konjugates, die nicht mit den i s unlöslich gemachten Antikörpers reagiert, wobei das Konjugat folglich in der flüssigen Phase verbleibt. Durch Messung der Enzymaktivität des Hapten-Enzym-Konjugates in der flüssigen Phase oder des umgesetzten Hapten-Enzym-Konjugates in der festen Phase kann die Menge an Haptenen in der zu untersu-20 chenden Flüssigkeit mit Hilfe einer Dosis-Reaktionskurve für ein bestimmtes System bestimmt werden.
In der niederländischen Patentanmeldung 7018 838 ist ein entsprechendes Verfahren zum Nachweis und zur Bestimmung von beispielsweise Haptenen beschrieben, das sich von dem 25 oben erwähnten Verfahren darin unterscheidet, dass das zu bestimmende Hapten und die Menge des Hapten-Enzym-Konjugates nicht mit unlöslich gemachten Antikörpern ungesetzt wird, sondern mit löslichen Antikörpern, wobei eine bestimmte Menge unlöslich gemachter Antikörper gegen die ersten Anti-3o körper (Anti-Antikörper) zu der Flüssigkeit nach der Konkurrenzreaktion zugegeben wird. Die Menge des Hapten-Enzym-Konjugates, die mit den ersten Antikörpern reagiert hat, wird dann an die unlöslich gemachten zweiten Antikörper gekuppelt und gelangt folglich in die unlösliche Fraktion, während der 35 Teil des Hapten-Enzym-Konjugates, der nicht reagiert hat, in der flüssigen Phase verbleibt
Auf die gleiche Weise wie bei dem oben beschriebenen Verfahren kann die Menge von Hapten in der zu untersuchenden Flüssigkeit in der flüssigen oder festen Phase durch eine Dosis-40 Reaktionskurve bestimmt werden nach Bestimmung der Enzymaktivität
Die entsprechende Dosis-Reaktionskurve wird gebildet, indem man von einer bestimmten Menge Hapten-Enzym-Kon-jugat ausgeht und diese mit Antiserum (Serum, enthaltend Anti-45 körper) in unterschiedlichen Verdünnungen zusammenbringt In jeder Verdünnung wird bestimmt wieviel Hapten-Enzym an die Antikörper gebunden ist Nun wird eine Antiserumverdün-nung ausgewählt, bei der z. B. 80% des Hapten-Enzyms gebunden ist und zu dieser Verdünnung werden unterschiedliche so Mengen Hapten zugesetzt. Für jede Haptenkonzentration wird dann bestimmt wieviel Hapten-Enzym gebunden ist z. B. bei einer Einheit Hapten 78% Konjugat und bei zwei Einheiten Hapten 75% Konjugat usw.
Gibt man dann die oben erwähnten Mengen Hapten-55 Enzym und Antiserum zu einer unbekannten Menge Hapten und misst die Enzymaktivität der gebundenen oder nichtgebundenen Hapten-Enzymfraktion, so kann die in der zu untersuchenden Flüssigkeit enthaltene Haptenmenge bestimmt werden.
60 Aus dem oben gesagten geht hervor, dass, wenn die Affinität des Hapten-Enzym-Konjugates für das Antiserum hoch ist, verglichen mit der Aktivität zwischen Hapten und Antikörper, verhältnismässig grosse Haptenmengen vorhanden sein müssen, wenn ein Ersatz durch das Hapten des Konjugates und 65 folglich eine messbare Enzymaktivität in der flüssigen Phase auftreten soll. Ziel der Erfindung ist es daher, die Affinität des Haptens gegenüber den Antikörpern zu erhöhen oder andererseits die Affinität des Hapten-Enzym-Konjugates gegenüber
den Antikörpern herabzusetzen, um die Empfindlichkeit des Testsystems zu erhöhen mit der Folge, dass mit diesem Testsystem sehr geringe Haptenkonzentrationen bestimmt werden können.
Überraschenderweise hat es sich nun gezeigt, dass die Empfindlichkeit der oben erwähnten Bestimmungsverfahren wesentlich zunimmt, wenn die Art der Kupplung zwischen Hapten und Enzym sich von der Kupplung zwischen Hapten und hochmolekularen Substanzen unterscheidet.
Unter einer andersartigen Kupplung zwischen Hapten-Enzym und Hapten-hochmolekularer Substanz ist zu verstehen a) eine chemisch unterschiedliche Bindung oder Brückenbildung,
b) chemisch unterschiedliche Haptene, die immunologisch verwandt sind,
c) Kupplung über eine andere Stelle des Haptenmoleküls und d) Kombinationen von (a), (b) und (c).
Haptenen sind proteinfreie Substanzen, hauptsächlich niedermolekulare, die die Antikörperbildung nicht stimmulie-ren können, aber die mit Antikörpern reagieren. Die letzteren werden gebildet durch Kupplung des Haptens an eine hochmolekulare Substanz, üblicherweise ein Polypeptid oder Protein und indem man dieses Kupplungsprodukt Menschen oder Tieren injiziert.
Als Beispiel für Haptene sind zu erwähnen Steroide, wie Östron, Östradiol, Östriol, Testosteron, Pregnandiol und Progesteron; Vitamine, wie Vitamin B12 und Folsäure, Thyrocin, Tri-jodidthyronin, Histamin, Serotonin, Digoxin, Prostaglandin, Adrenalin, nor-Adrenalin, Morphin, pflanzliche Hormone, wie Auxin, Kinetin und Gibberellinsäure und Antibiotika, wie Penicillin.
Zur Herstellung des Kupplungsproduktes Hapten-Enzym können üblicherweise die Substituenten, die schon in den Komponenten vorhanden sind, wie Hydroxyl-, Carboxy-, Amino-oder Ketogruppen verwendet werden. Wenn keine dieser Gruppen verhanden ist, ist es möglich, diese noch besonders in die Haptene einzuführen. So kann z. B. eine Hydroxylgruppe in Steroide auf mikrobiologische oder chemische Weise in verschiedenen Stellen des Moleküls, wie in der 6-, 11- oder 16-Stel-lung eingeführt werden.
Mit Hilfe einer Polycarbonsäure oder eines funktionellen Derivates einer solchen Säure können solche Hydroxyverbin-dungen an ein Enzym gekuppelt werden. Es ist auch möglich, von einem Hapten auszugehen, das eine Ketogruppe besitzt oder in das eine solche Gruppe eingeführt worden ist, woraufhin die Kupplung mit dem Enzym über ein Carboxyalkyloxim-derivat stattfinden kann. Wenn das Hapten zusammen mit dem Enzym Amino- oder Carboxylgruppen besitzt, können die beiden Komponenten nach einem von der Peptidsynthese her bekannten Verfahren gekuppelt werden.
Abhängig von dem Vorhandensein geeigneter Substituenten können auch andere Substanzen, wie Dialdehyde, z.B. Glu-taraldehyd, Hydrazine, Difluordinitrodiphenylsulfon, Diisocya-nate, wie Toluoldiisocyanat und Di- oder Trichlortriazine für die Kupplung verwendet werden.
Das für das oben beschriebene Konjugat verwendete Enzym kann im Prinzip aus jeder Klasse gewählt werden, bevorzugt sind jedoch solche Enzyme, die eine hohe spezifische Aktivität besitzen die auf einfache Weise bestimmt werden kann, z. B. colorimetrisch, spektrophotometrisch oder fluo-rometrisch.
Beispiele für Enzyme, die bevorzugt verwendet werden,
sind Katalasen, Peroxidasen, Glucuronidasen, Glucosidasen, Galactosidasen, Urease und Oxidoreductasen, wie Glucoseoxi-dase und Galactoseoxidase.
Zur Herstellung der Antikörper gegen das Hapten wird das Hapten mit einer hochmolekularen Substanz, üblicherweise
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einem Protein, gekuppelt und einem Tier injiziert, woraufhin der Antikörper auf übliche Weise isoliert wird.
Zur Kupplung des Haptens an ein Protein oder möglicherweise eine andere hochmolekulare Substanz, die die Antikörperbildung stimulieren kann, können gleiche Kupplungsverfahren angewandt werden, wie sie für die Kupplung des Haptens an das Enzym beschrieben sind.
Wichtig für das erfindungsgemässe Verfahren ist jedoch, dass die Art der Kupplung sich von derjenigen in dem Hapten-Enzym-Konjugat unterscheiden soll. Der Unterschied kann chemischer Art sein, indem bei dem Enzymkonjugat die Kupplung z. B. über eine Polycarbonsäure erzielt worden ist, während die Kupplung zwischen dem Hapten und Protein über eine Carboximmethyloxybrücke gebildet worden ist. Es ist auch möglich, dass die Kupplung in beiden Fällen über eine Polycarbonsäure, z. B. eine Dicarbonsäure, gebildet wird, wenn in dem einen Falle die Dicarbonsäure X C-Atome, z. B. zwei C-Atome im Falle von Oxalsäure und im anderen Falle Y C-Atome, z. B. vier, im Falle von Bernsteinsäure enthält.
Eine unterschiedliche Art der Kupplung kann auch dadurch erreicht werden, wenn das Hapten in dem Hapten-Enzym-Kon-jugat und das Hapten in dem Produkt Hapten-hochmolekulare Substanz chemisch unterschiedlich aber immunologisch verwandt sind. Dieser chemische Unterschied tritt ein, wenn beide Haptene sich durch das Vorhandensein oder Nichtvorhandensein einer oder mehrerer Doppelbindungen unterscheiden, z. B. Testosteron und Dihydrotestosteron und/oder einer oder mehrerer Substituenten, wie Hydroxylgruppen, Oxogruppen, Halogenatomen, Alkylgruppen usw., z. B. Östradiol und 1 la-Hydroxy-östradiol oder dass ein Hapten ein funktionelles Derivat, z. B. ein Acylat oder Äther des anderen Haptens ist, z. B. Morphin und Codein.
Es hat sich sogar gezeigt, dass es einfach ist, ein empfindlicheres Testsystem zu erhalten bei Anwendung gleichartiger Bindungen in beiden Kupplungsprodukten, wenn die Bindung über andere Stellungen des Haptenmoleküls gebildet werden, z. B. im Falle von östradiol als Hapten über das 11-Succinyloxy-und 17-Succinyloxyderivatvon 11-Hydroxyöstradiol.
Für die Abtrennung des an den Antikörper gebundenen Enzym-Konjugates von dem ungebundenen können verschiedene Verfahren angewandt werden, wie eine Ausfällung des Konjugates, das an die Antikörper gebunden ist, mit einem organischen Lösungsmittel oder Salz, selektive Absorption des freien Konjugates an Aktivkohle, die mit einer Dextranschicht bedeckt ist, oder Ausfällung des an die Antikörper gebundenen Konjugates mit Hilfe von (zweiten) Antikörpern gegen die Antikörper der Tierart, in der die Antikörper gegen das Hapten gebildet worden sind. Dieses zuletzt genannte Verfahren wird üblicherweise als «doppeltes Antikörper»-Verfahren bezeichnet.
Die Trennung kann auch leicht erreicht werden, indem man die Antikörper gegen das Hapten unlöslich macht, bevor man sie an der Reaktion mit dem Hapten und Konjugat teilnehmen lässt Die Abtrennung findet dann durch einfaches Zentrifugie-ren statt. Dieses Verfahren wird oft als «festes Phasen»-Verfah-ren bezeichnet. Die Antikörper können durch Vernetzung mit z. B. Glutaraldehyd oder einem Chlorameisensäurealkylester oder durch Kupplung an einen unlöslichen Träger, wie Cellulose, Agarose, Polystyrol oder ähnliches unlöslich gemacht werden.
Das «doppelte Antikörper»- und «festes Phasen»-Verfah-ren können in dem sogenannten DASP-Verfahren kombiniert werden. In diesem Falle wird ein zweiter Antikörper gegen den ersten Antikörper gebildet, indem man die Immunoglobulin-fraktion des ersten Antiserums oder von normalem Serum der gleichen Tierart einer Tierart injiziert, die sich von derjenigen unterscheidet, von der das erste Antiserum erhalten worden ist und dann das zweite Antiserum durch die oben beschriebenen
3
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25
30
35
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65
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Verfahren zur Unlöslichmachung des ersten Antikörpers, z. B. durch Kupplung an Celluloseteilchen unlöslich macht.
Zur Durchführung des erfindungsgemässen Verfahrens wird vorzugsweise eine fertige Testpackung angewandt.
Eine Testpackung zur Bestimmung mit Hilfe eines unlöslich s gemachten Antikörpers besteht hauptsächlich aus
(1) einer vorher bestimmten Menge eines Hapten-Enzym-Konjugates und
(2) einer vorher bestimmten Menge eines Antikörpers in unlöslicher Form. io
Eine Testpackung zur Durchführung der erfindungsgemässen Bestimmung mit Hilfe eines unlöslich gemachten zweiten Antiserums (d. h. DASP-Verfahren) besteht hauptsächlich aus
(1) einer vorher bestimmten Menge eines Hapten-Enzym-Konjugates, 15
(2) einer vorher bestimmten Menge eines-ersten Antiserums und
(3) einer vorbestimmten Menge eines unlöslich gemachten zweiten Antiserums.
Ausser den oben angegebenen Reagentien können beide 20 Testpackungen zusätzliche Komponenten enthalten, z. B. Reagenzien zur Bestimmung der Aktivität des angewandten Enzyms.
Die Erfindung wird durch die folgenden Beispiele näher erläutert. 25
Beispiel 1
Bestimmung von Östrogen
A. Herstellung von Östradiol-17-succinyl-HRP und 1 la-Östra-diol-ll-succinyl-HRP 30
50 mg östradiol-17-hemisuccinat oder 50 mg 1 la-OH-Östradiol-11-hemisuccinat wurden in 2 cm3 Dioxan gelöst. Das Gemisch wurde auf 8 °C abgekühlt und anschliessend 0,07 cm3 Tri-n-butylamin und 0,015 cm3 Isobutylchlorcarbonat zugegeben. 30 min später wurden 50 mg Meerrettichperoxidase (HRP) 35 in 5,5 cm3 Wasser/Dioxan (3:2) mit einem pH-Wert von 9 zugegeben. Das Gemisch wurde 4 Stunden umgesetzt und anschliessend über Nacht gegen laufendes Leitungswasser dialysiert und dann über eine Säule aus einem vernetzten Dextrangel (Sepha-dex G-25) in destilliertem Wasser gereinigt. Die enzymhaltigen 40 Fraktionen wurden lyophilisiert. Eine weitere Reinigung der Konjugate wurde erreicht durch Dichtegradientzentrifugie-rung(20-60% Saccharose, 16 Stunden, 238 OOOx g).
B. Herstellung von östradiol-17-succinyl-BSA und 1 la-Östra- 45 diol-11-succinyl-BSA
Diese Konjugate wurden auf die gleiche Weise hergestellt wie die entsprechenden HRP-Derivate, wobei als Ausgangssubstanzen 50 mg Östradiol-hemisuccinat und 150 mg BSA (Rinderserumalbumin) verwendet wurden. Ausserdem wurde das 50 Gemisch dreimal mit 1,5 Vol.-Teilen Aceton mit einem pH-Wert von 4,5 umgefällt und nicht über Dextrangel gereinigt.
D. Bestimmung von Östrogen
In einem Vorversuch wurde für jedes Antiserum bestimmt, welcher Anteil der Enzymaktivität jedes Östradiol-HRP-Kon-jugates (in einer vorher bestimmten günstigen Konzentration) gebunden war, wobei eine Antiserumkonzentration 0,5 cm3 Puffer, 0,1 cm3 Östradiol-HRP und 0,1 cm3 Antiserum (in Verdünnung von 1:100 bis 1:10 000) bei Raumtemperatur 30 min inkubiert wurde. Dann wurden 0,3 cm3 einer Suspension von DASP Anti-Kaninchen (Schafantikörper gegen Kaninchen-y-globulin, kovalent an Cellulose gebunden) zugegeben und das entstehende Gemisch 2 Stunden geschüttelt. Dann wurde das Gemisch zentrifugiert und anschliessend 0,5 cm3 der überstehenden Flüssigkeit mit 1,5 cm3 Enzymsubstrat (80 mg 5-Amino-salicylsäure und 10 jil einer 30%igen Wasserstoffperoxidlösung in 150 cm3 0,02 m Phosphatpuffer mit einem pH-Wert von 6,0) vermischt. Nach einer Stunde wurde die Extinktion bei 450 nm gemessen. Für die folgenden Östrogenbestimmungen wurde jeweils eine solche Antiserumverdünnung ausgewählt, dass ungefähr 40% der Enzymaktivität des Östradiol-HRP an DASP Antikaninchen in Abwesenheit von freiem Östrogen gebunden wurden. 0,5 cm3 einer Östron-, Östradiol- oder Östriol-Lösung (Konzentrationen von 0,1 bis 1000 ng/cm3) wurden 30 min mit 0,1 cm3 Antiserum in der festgelegten Verdünnung inkubiert und anschliessend 0,1 cm3 Östradiol HRP in der ausgewählten Konzentration zugegeben und das Gemisch erneut 30 min inkubiert. Dann wurden 0,3 cm3 der DASP Antikaninchensu-spension zugegeben und die Bestimmung weiter, wie oben beschrieben, durchgeführt. Die Empfindlichkeit der Bestimmungsverfahren ist in der folgenden Tabelle angegeben: Östrogenmenge in ng/cm3, die erforderlich ist, um die Hälfte des Östradiol-HRP an der Bindung mit Antikörper zu hindern
Antiserum gegen
Konjugat
E2-II-BSA Ez-U-HRP
EÎ-17-HRP
E2-17-BSA E2-II-HRP
E2-I7-HRP
Östron
1000
7
3
7
Östradiol
800
1,5
2
7
Östriol
1000
230
14
380
C. Herstellung von Antikörpern gegen Östradiol-17-succinyl-BSA und 1 la-östradiol-11-succinyl-BSA
Kaninchen wurden mit dem entsprechend B hergestellten Produkten nach dem folgenden Schema immunisiert:
Zeit (d)
Menge (mg Art
Freund's Zusatz i.m. = intramuskulär i.v. = intravenös
55
0
14
28
42
49 60
0,25
0,25
0,25
0,25
blutend i.m.
i.m.
i.m.
i.V.
+
+
+
—
65
E2 = Östradiol
Ähnliche Ergebnisse wurden mit verschiedenen Antisera erhalten. Wenn nicht anders angegeben, wurde 0,1 m Phosphat mit einem pH-Wert von 6,0, enthaltend 0,1 % Lactalbumin als Puffer verwendet.
Beispiel 2
Bestimmung von Östrogen
A. Herstellung von Östradiol-17-succinyl-HRP, Östradiol-17-maleinyl-HRP, Östradiol-17-glutaryl-HRP und Östron-17-N-car-boxymethyloxim-HRP
Diese Produkte wurden wie in Beispiel 1A beschrieben hergestellt, wobei die Menge der Östrogenderivate entsprechend ihrem Molekulargewicht gewählt wurde und die Reaktion mit Östron-17-0-(caroxymethyl)-oxim in einem Gemisch von DimethylformamidAVasser anstelle eines Gemisches von Dio-xan/Wasser durchgeführt wurde.
B. Bestimmung von Östrogen
Die Bestimmung wurde wié in Beispiel 1 D durchgeführt unter Verwendung von zwei Antisera gegen Östradiol-17-succinyl-BSA (s. Beispiele 1 B und C). Die Empfindlichkeit der Bestimmung ist in der folgenden Tabelle angegeben: Konzentration von Östron (Ei), Östradiol (E2) und Östriol (E3) in ng/
5
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cm3, die erforderlich sind, um die Hälfte des Östradiol-HRP an der Bindung mit Antikörper zu hindern.
Antiserum
Kaninchen A
Kaninchen B
Hapten
Ei
E2
E3
Ei
E2
Ea
Succinyl
4
6
190
12
9
300
Maleinyl
3
4
160
3
3
100
Glutaryl
4
5
150
8
6
300
Oxim
2
2
150
1
0,8
50
Beispiel 3
Bestimmung von Progesteron 15
A. Herstellung von 1 la-OH-progesteron-11-succinyl-alkali-scher Phosphatase (AP) und 12a-OH-progesteron-12-succi-nyl-AP
Diese Substanzen wurden analog den Östrogenderivaten in Beispiel 1 A hergestellt, wobei die Ausgangssubstanzen 55 mg 20 Progesteron-Hemisuccinat und 125 mg AP waren.
B. Herstellung von 1 la-OH-progesteron-11-succinyl-BSA und 12a-OH-progesteron-l 2-succinyl-BS A
Diese Substanzen wurden analog den Östrogen-Derivaten 25 in Beispiel 1 B hergestellt
C. Herstellung von Antikörpern gegen 1 la-OH-progesteron-
11-succinyl-BSA und 12a-OH-progesteron-12-succinyl-BSA Diese Antikörper wurden entsprechend dem Schema des 3b
Beispiels 1 C hergestellt.
D. Bestimmung von Progesteron
Das angewandte Verfahren unterschied sich nicht wesentlich von dem für die Bestimmung von östradiol in Beispiel 1 D 35 beschriebenen Verfahren. Die Enzymbestimmung fand fol-gendermassen statt: 0,5 cm3 einer enzymhaltigen Probe wurden zugegeben zu 0,5 cm3 einer Substratlösung (0,01 m p-Nitrophe-nylphosphat in 0,1 m Carbonatpuffer mit einem pH-Wert von 2 und 0,007 m MgCk). Das Gemisch wurde 30 Minuten bei 37 °C 40 inkubiert und anschliessend die Extinktion bei 400 nm gemessen.
Man sah, dass Bestimmungssysteme, bei denen Progeste-ron-11-AP kombiniert war mit Antiprogesteron-11-BSA oder Progesteron-12-AP mit Antiprogesteron-12-BS A 4-1 Ornai weni-45 ger empfindlich gegenüber Progesteron waren, als die Systeme Progesteron-1 l-AP/Antiprogesteron-12-BSA und Progesteron-
12-AP/Antiprogesteron-l 1-BSA.
Die in diesem Beispiel beschriebenen Reaktionen wurden durchgeführt in 0,01 m Veronalpuffer, pH 7,5, enthaltend 0,1 % 50 Lactalbumin, soweit nicht anders angegeben.
E. Bestimmung von Progesteron
Ähnliche Ergebnisse wie in Beispiel 3 D beschrieben wurden mit dem folgenden Testsystem erhalten: 0,5 cm3 einer Progesteronlösung wurden mit 0,1 cm3 Antiserum in einer geeigneten Verdünnung 30 Minuten inkubiert und anschliessend 0,1 cm3 Progesteron-AP in einer geeigneten Konzentration zugegeben und das Gemisch erneut 30 Minuten inkubiert.
Dann wurden 0,3 cm3 einer Norit-Suspension (25 mg/cm3), die vorher mit Dextran inkubiert und dann gewaschen worden war zugegeben und das Gemisch 15 Minuten zentrifugiert und die AP-Aktivität in der überstehenden Flüssigkeit wie in Beispiel 3 D beschrieben, bestimmt.
25 mg l-Cyclohexyl-3-(2-morpholinoäthyl)carbodiimidund anschliessend 20 mg Folsäure wurden zu 50 mg methyliertem Rinderserumalbumin (MBSA) in 5 cm3 0,05 m Phosphatpuffer, pH 7,0 gegeben. Das Gemisch wurde 2 Stunden umgesetzt und anschliessend ausgiebig gegen destilliertes Wasser dialysiert und dann lyophilisiert.
B. Herstellung von Antisera gegen Folat MBSA
Bei diesem Verfahren wurde das Schema des Beispiels 1 C angewandt.
C. Herstellung von Folat-glucoseoxidase (FGO) und Pteroyl-glucoseoxidase (PGO)
1 mg Folsäure oder 0,7 mg Pterosäure wurden in 5 cm3 0,05 m Phosphatpuffer, pH 7, enthaltend 0,5 mg l-Cyclohexyl-3-(2-morpholino-äthyl)-carbodiimid gelöst. Nach 5 Minuten wurden 50 mg Glucoseoxidase in dem Gemisch gelöst und die Reaktion zwei Stunden fortgesetzt. Dann wurde die Lösung gegen 0,05 m Phosphatpuffer, pH 7,0, eine Zeit lang dialysiert.
D. Bestimmung von Folsäure
Das Bestimmungsverfahren war im wesentlichen das Gleiche wie im Beispiel 1 D beschrieben. Die Enzymbestimmung wurde folgendermassen durchgeführt: 0,5 cm3 der enzymhaltigen Lösung wurden mit 2,5 cm3 der Substratlösung (50 mg Glucose, 10 p,g Peroxidase und 1 mg 5-Aminosalicyl-säure in 0,05 m Phosphatpuffer, pH 6,0) vermischt und anschliessend 30 Minuten die Extinktion bei 450 nm gemessen. Das Testverfahren, bei dem Antikörper gegen Folat MBSA kombiniert wurden mit FGO erwies sich als 3-20mal weniger empfindlich als dasjenige, bei dem die Antikörper kombiniert waren mit PGO. Der Unterschied in der Empfindlichkeit variiert für jedes einzelne Antiserum.
Beispiel 5
Bestimmung von Östrogen
A. Herstellung von 1 la-OH-östron-11-succinyl-HRP, 1 la-OH-östron-11-glutanyl-HRP, 1 la-OH-östradiol-11-succinyl-HRP und 1 la-OH-östradiol-11-glutanyl-HRP
Diese Verbindungen wurden wie im Beispiel 1A beschrieben hergestellt. Die Menge der Östrogenderivate, die verwendet wurde, wurde entsprechend dem Molekulargewicht gewählt.
B. Bestimmung von Östrogen
Die Bestimmung wurde mit den vier oben erwähnten E-HRP-Konjugaten durchgeführt, wobei das Antiserum gegen 1 la-OH-östradiol-11-succinyl-BSA, das unter Beispiel 1 B und 1 C beschrieben ist, verwendet wurde.
Die Empfindlichkeit der Bestimmungen sind in der folgenden Tabelle angegeben:
östrogenmenge in ng/cm3, die erforderlich ist, um eine Bindung der Hälfte des Östrogen-HRP an den Antikörper zu verhindern.
55
60
E-HRP Konjugat
Ei
E2
E2-11-Succinyl-HRP
>1000
>1000
Ez-11-Glutanyl-HRP
>1000
8
E2-11-Succinyl-HRP
>1000
5
Ei-11-Glutanyl-HRP
80
0,8
Beispiel 4
Bestimmung von Folsäure A. Herstellung von Folat MBSA
65 Beispiel 6
Bestimmung von Östrogen
A. Herstellung von Östradiol-17-succinyl-HRP und östriol-16, 17-disuccinyl-HRP
622099
Diese Verbindungen wurden wie in Beispiel 1 A beschrieben hergestellt, wobei das Molekulargewicht der jeweiligen Östrogenderivate berücksichtigt wurde.
B. Herstellung von Anti(östradiol-17-succinyl-BSA) und Anti(östriol-l 6,17-disuccinyl-BSA)
Diese Antisera wurden wie in Beispiel 1A und 1 B angegeben, hergestellt
6
C. Östrogenbestimmungen
Die vier möglichen Kombinationen von Östrogen-HRP-Konjugat und Antisera wurden für Östrogenbestimmungen, wie im Beispiel 1 D beschrieben, verwendet. 5 Die Ergebnisse für zwei Antisera sind in der folgenden Tabelle angegeben:
Östrogenmenge in ng/cm3, die erforderlich ist, um die Hälfte des Östrogen-HRP an der Bindung mit dem Antikörper zu hindern.
Antiserum gegen E2-17-BSA E3-16.17-BSA
Konjugat E2-17-HRP E3-16,17-HRP Eî-17-HRP E3-16,17-HRP
Östron >300 6 30 100
Östradiol >300 16 30 150
Östriol >300 70 100 300
Beispiel 7 20 Beispiel 8
Bestimmung von Morphin Bestimmung von Testosteron
A. Herstellung von Codein-6-succinyl-HRP A. Herstellung von 1 la-OH-Testosteron-11-succinyl-HRP,
Nach dem in Beispiel 1A beschriebenen Verfahren wurde 1 la-OH-Dihydrotestosteron-11-succinyl-HRP und 1 la-OH-nor-Codein-6-hemisuccinat in Codein-6-succinyl-HRP umgewan- testosteron-11-succinyl-HRP.
delt. 25 Diese Verbindungen wurden nach den für die Östrogene in
Beispiel 1A beschriebenen Verfahren hergestellt.
B. Herstellung von Morphin-3,6-diglutaryl-BSA und Herstellung eines Antiserums gegen dieses Produkt B. Herstellung von anti(l la-OH-testosteron-11-succinyl-BSA)
Nach dem in Beispiel 1 B beschriebenen Verfahren wurde . Dieses Antiserum wurde wie im Beispiel 1 B und C für Morphin-3,6-dihemiglutarat umgewandelt in Morphin-3,6-diglu- 30 Östrogenantisera beschrieben, hergestellt taryl-BSA und das Antiserum gegen dieses Produkt wie unter 1
C beschrieben, hergestellt C. Testosteronbestimmung
Testosteron wurde nach dem für Östrogene in Beispiel 1D
C. Bestimmung von Morphin beschrieben Verfahren bestimmt
Nach dem in Beispiel 1 D beschriebenen Verfahren wurde 35 Unter Verwendung von Testosteron-HRP waren 30 ng/cm3 die Menge Morphin in einer Probe bestimmt, indem die flüssige Testosteron für eine 50%ige Hemmung der Bindung des Konju-und feste Phase unter Verwendung von DASP-Antikaninchen- gates an Antiserum erforderlich. Unter Verwendung des glei-serum getrennt wurden. chen Antiserums und Dihydrotestosteron-HRP waren jedoch
.... 5 ng/cm3 Testosteron ausreichend, um die gleiche Reaktion zu
10 ng/cm Morphin waren für eine 50%ige Hemmung der 40 erzielen. Nortestosteron-HRP war von mittlerer Empfindlich-Bindung von Codein-6-succinyl-HRP an Antiserum gegen Mor- keit> und es waren I5 ng/cm3 Testosteron für eine 50%ige Hem-phin-3,6-diglutaryl-BSA erforderlich. mung der Bindung an die Antikörper erforderlich.
Claims (9)
- 622099PATENTANSPRÜCHE1. Verfahren zur Bestimmung von Haptenen, bei dem man eine flüssige Probe mit vorher bestimmten Mengen Hapten-Enzym-Konjugàt und eines Antikörpers für das Hapten und Hapten-Enzym-Konjugat zusammenbringt, das an den Antikörper gebundene Hapten-Enzym-Konjugat von dem nichtgebundenen Hapten-Enzym-Konjugat abtrennt und die Enzymaktivität in einer der beiden Fraktionen misst dadurch gekennzeichnet, dass man die Hapten-Enzym-Konjugat verwendet, bei dem sich die Kupplung zwischen dem Enzym und dem Hapten unterscheidet von der Kupplung zwischen dem Hapten und der hochmolekularen Substanz im Kupplungsprodukt aus dem Hapten und einer hochmolekularen Substanz, das zur Entwicklung des Antikörpers verwendet wurde.
- 2. Verfahren nach Patentanspruch 1, dadurch gekennzeichnet, dass man die Trennung zwischen dem an den Antikörper gebundenen und nicht-gebundenen Hapten-Enzym-Konjugat durchführt, indem man die zu analysierende Probe mit einem unlöslich gemachten Antikörper gegen die Antikörper der Tierart, in der die Antikörper gegen das Hapten gebildet worden sind, zusammenbringt.
- 3. Verfahren nach Patentanspruch 1 oder 2, dadurch gekennzeichnet, dass man als Hapten ein Östrogen verwendet.
- 4. Verfahren nach Patentanspruch 1 oder 2, dadurch gekennzeichnet, dass man als Hapten Progesteron oder Folsäure verwendet
- 5. Verfahren nach Patentanspruch 1, dadurch gekennzeichnet, dass man den Antikörper für das Hapten und Hapten-Enzym-Konjugat in unlöslich gemachter Form verwendet.
- 6. Testpackung zur Durchführung des Verfahrens nach Patentanspruch 1, dadurch gekennzeichnet, dass sie einer vorher bestimmte Menge eines Hapten-Enzym-Konjugates und eine vorher bestimmte Menge eines Antikörpers für das Hapten und Hapten-Enzym-Konjugat enthält.
- 7. Testpackung nach Patentanspruch 6, dadurch gekennzeichnet, dass der Antikörper für das Hapten und Hapten-Enzym-Konjugat in unlöslich gemachter Form vorliegt.
- 8. Testpackung nach Patentanspruch 6 oder 7, dadurch gekennzeichnet, dass sie zusätzlich eine vorbestimmte Menge eines unlöslich gemachten Antikörpers gegen die Antikörper der Tierart, in der die Antikörper gegen das Hapten gebildet worden sind, enthält
- 9. Testpackung nach Patentanspruch 6, dadurch gekennzeichnet, dass sie zusätzlich Reagenzien zur Bestimmung der Aktivität des angewandten Enzyms enthält.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NLAANVRAGE7206373,A NL171930C (nl) | 1972-05-11 | 1972-05-11 | Werkwijze voor het aantonen en bepalen van haptenen, alsmede testverpakkingen. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH622099A5 true CH622099A5 (de) | 1981-03-13 |
Family
ID=19816017
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH665673A CH622099A5 (de) | 1972-05-11 | 1973-05-10 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US3879262A (de) |
| JP (1) | JPS5317648B2 (de) |
| AR (1) | AR200129A1 (de) |
| AT (1) | AT328612B (de) |
| BE (1) | BE799417A (de) |
| BR (1) | BR7303420D0 (de) |
| CA (1) | CA1011232A (de) |
| CH (1) | CH622099A5 (de) |
| DE (1) | DE2323467C2 (de) |
| DK (1) | DK135965B (de) |
| ES (1) | ES414618A1 (de) |
| FI (1) | FI52154C (de) |
| FR (1) | FR2184371A5 (de) |
| GB (1) | GB1433783A (de) |
| HU (1) | HU169436B (de) |
| NL (1) | NL171930C (de) |
| SE (1) | SE417015B (de) |
| ZA (1) | ZA732924B (de) |
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Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3654090A (en) * | 1968-09-24 | 1972-04-04 | Organon | Method for the determination of antigens and antibodies |
| NL154598B (nl) * | 1970-11-10 | 1977-09-15 | Organon Nv | Werkwijze voor het aantonen en bepalen van laagmoleculire verbindingen en van eiwitten die deze verbindingen specifiek kunnen binden, alsmede testverpakking. |
| NL154599B (nl) * | 1970-12-28 | 1977-09-15 | Organon Nv | Werkwijze voor het aantonen en bepalen van specifiek bindende eiwitten en hun corresponderende bindbare stoffen, alsmede testverpakking. |
| US3709868A (en) * | 1971-03-08 | 1973-01-09 | Hoffmann La Roche | Opium alkaloid antigens and antibodies specific therefor |
| US3817837A (en) * | 1971-05-14 | 1974-06-18 | Syva Corp | Enzyme amplification assay |
| US3766162A (en) * | 1971-08-24 | 1973-10-16 | Hoffmann La Roche | Barbituric acid antigens and antibodies specific therefor |
-
1972
- 1972-05-11 NL NLAANVRAGE7206373,A patent/NL171930C/xx not_active IP Right Cessation
-
1973
- 1973-04-30 GB GB2041673A patent/GB1433783A/en not_active Expired
- 1973-04-30 ZA ZA732924A patent/ZA732924B/xx unknown
- 1973-05-01 US US356223A patent/US3879262A/en not_active Expired - Lifetime
- 1973-05-08 AR AR247898A patent/AR200129A1/es active
- 1973-05-09 DK DK255773AA patent/DK135965B/da not_active IP Right Cessation
- 1973-05-09 FI FI731493A patent/FI52154C/fi active
- 1973-05-09 DE DE2323467A patent/DE2323467C2/de not_active Expired
- 1973-05-10 ES ES0414618A patent/ES414618A1/es not_active Expired
- 1973-05-10 BR BR3420/73A patent/BR7303420D0/pt unknown
- 1973-05-10 HU HUAO364A patent/HU169436B/hu unknown
- 1973-05-10 CA CA170,907A patent/CA1011232A/en not_active Expired
- 1973-05-10 JP JP5204273A patent/JPS5317648B2/ja not_active Expired
- 1973-05-10 CH CH665673A patent/CH622099A5/de not_active IP Right Cessation
- 1973-05-10 SE SE7306570A patent/SE417015B/xx unknown
- 1973-05-11 AT AT416473A patent/AT328612B/de not_active IP Right Cessation
- 1973-05-11 BE BE131015A patent/BE799417A/xx not_active IP Right Cessation
- 1973-05-11 FR FR7317181A patent/FR2184371A5/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DK135965C (de) | 1977-12-19 |
| AU5517073A (en) | 1974-11-07 |
| AT328612B (de) | 1976-03-25 |
| ZA732924B (en) | 1974-04-24 |
| SE417015B (sv) | 1981-02-16 |
| JPS5317648B2 (de) | 1978-06-09 |
| BE799417A (fr) | 1973-11-12 |
| US3879262A (en) | 1975-04-22 |
| JPS4962192A (de) | 1974-06-17 |
| DE2323467C2 (de) | 1982-01-14 |
| FI52154C (fi) | 1977-06-10 |
| HU169436B (de) | 1976-11-28 |
| FR2184371A5 (de) | 1973-12-21 |
| FI52154B (de) | 1977-02-28 |
| BR7303420D0 (pt) | 1974-08-29 |
| CA1011232A (en) | 1977-05-31 |
| NL7206373A (de) | 1973-11-13 |
| DK135965B (da) | 1977-07-18 |
| DE2323467A1 (de) | 1973-11-29 |
| AR200129A1 (es) | 1974-10-24 |
| ATA416473A (de) | 1975-06-15 |
| NL171930B (nl) | 1983-01-03 |
| ES414618A1 (es) | 1976-09-01 |
| GB1433783A (en) | 1976-04-28 |
| NL171930C (nl) | 1983-06-01 |
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