JPS6061596A - 新規ステロイド化合物，その製造方法，及びその化合物からなる免疫化学的測定法によるエストラジオ−ル−３−サルフエ−ト−１７β−グルクロナイド測定用抗原 - Google Patents
新規ステロイド化合物，その製造方法，及びその化合物からなる免疫化学的測定法によるエストラジオ−ル−３−サルフエ−ト−１７β−グルクロナイド測定用抗原Info
- Publication number
- JPS6061596A JPS6061596A JP17092583A JP17092583A JPS6061596A JP S6061596 A JPS6061596 A JP S6061596A JP 17092583 A JP17092583 A JP 17092583A JP 17092583 A JP17092583 A JP 17092583A JP S6061596 A JPS6061596 A JP S6061596A
- Authority
- JP
- Japan
- Prior art keywords
- glucuronide
- sulfate
- oxime
- formula
- carboxymethyl
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 20
- 239000000427 antigen Substances 0.000 title claims abstract description 19
- 102000036639 antigens Human genes 0.000 title claims abstract description 19
- 108091007433 antigens Proteins 0.000 title claims abstract description 19
- -1 steroid compound Chemical class 0.000 title claims description 9
- 230000000984 immunochemical effect Effects 0.000 title abstract description 10
- 238000002360 preparation method Methods 0.000 title abstract description 4
- 229930182480 glucuronide Natural products 0.000 title description 5
- 238000000034 method Methods 0.000 claims abstract description 23
- KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims abstract description 3
- 108091003079 Bovine Serum Albumin Proteins 0.000 claims abstract 3
- 229940098773 bovine serum albumin Drugs 0.000 claims abstract 3
- 239000000126 substance Substances 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 150000002923 oximes Chemical class 0.000 claims description 13
- 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 claims description 11
- 229960005309 estradiol Drugs 0.000 claims description 11
- 229930182833 estradiol Natural products 0.000 claims description 11
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 3
- IALMOTQBDDQPED-KBEGMRNHSA-N (8s,9s,13s,14s)-13-methyl-8,9,11,12,14,15,16,17-octahydro-7h-cyclopenta[a]phenanthren-6-one Chemical compound C1C(=O)C2=CC=CC=C2[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 IALMOTQBDDQPED-KBEGMRNHSA-N 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 15
- 238000005259 measurement Methods 0.000 description 10
- 229940088597 hormone Drugs 0.000 description 9
- 239000005556 hormone Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000003556 assay Methods 0.000 description 7
- 238000000691 measurement method Methods 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 102000004190 Enzymes Human genes 0.000 description 5
- 108090000790 Enzymes Proteins 0.000 description 5
- 230000009260 cross reactivity Effects 0.000 description 5
- 150000003431 steroids Chemical class 0.000 description 5
- IJJWOSAXNHWBPR-HUBLWGQQSA-N 5-[(3as,4s,6ar)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-n-(6-hydrazinyl-6-oxohexyl)pentanamide Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)NCCCCCC(=O)NN)SC[C@@H]21 IJJWOSAXNHWBPR-HUBLWGQQSA-N 0.000 description 4
- 241000283973 Oryctolagus cuniculus Species 0.000 description 4
- 230000004520 agglutination Effects 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000008134 glucuronides Chemical class 0.000 description 4
- 239000004816 latex Substances 0.000 description 4
- 229920000126 latex Polymers 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- ZHTDDOWJIRXOMA-YVEZLPLXSA-N (8r,9s,13s,14s,17s)-3,17-dihydroxy-13-methyl-8,9,11,12,14,15,16,17-octahydro-7h-cyclopenta[a]phenanthren-6-one Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CC(=O)C2=C1 ZHTDDOWJIRXOMA-YVEZLPLXSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 210000001124 body fluid Anatomy 0.000 description 3
- 239000010839 body fluid Substances 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 230000035931 haemagglutination Effects 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- QZIGLSSUDXBTLJ-ZBRFXRBCSA-N 17beta-estradiol 3-sulfate Chemical compound OS(=O)(=O)OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 QZIGLSSUDXBTLJ-ZBRFXRBCSA-N 0.000 description 2
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 230000037029 cross reaction Effects 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 239000003163 gonadal steroid hormone Substances 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 238000002649 immunization Methods 0.000 description 2
- 230000003053 immunization Effects 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- 230000002611 ovarian Effects 0.000 description 2
- 238000003127 radioimmunoassay Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 229960005349 sulfur Drugs 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- 241000272875 Ardeidae Species 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 235000017166 Bambusa arundinacea Nutrition 0.000 description 1
- 235000017491 Bambusa tulda Nutrition 0.000 description 1
- 241001330002 Bambuseae Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- 102000053187 Glucuronidase Human genes 0.000 description 1
- 108010060309 Glucuronidase Proteins 0.000 description 1
- 235000015334 Phyllostachys viridis Nutrition 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
- 229930006000 Sucrose Natural products 0.000 description 1
- 102000005262 Sulfatase Human genes 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 description 1
- 239000011425 bamboo Substances 0.000 description 1
- 239000012472 biological sample Substances 0.000 description 1
- 210000000601 blood cell Anatomy 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 229940011871 estrogen Drugs 0.000 description 1
- 239000000262 estrogen Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002795 fluorescence method Methods 0.000 description 1
- 230000003325 follicular Effects 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000003018 immunoassay Methods 0.000 description 1
- 230000016784 immunoglobulin production Effects 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000941 radioactive substance Substances 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 108060007951 sulfatase Proteins 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000010257 thawing Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Steroid Compounds (AREA)
- Peptides Or Proteins (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17092583A JPS6061596A (ja) | 1983-09-16 | 1983-09-16 | 新規ステロイド化合物，その製造方法，及びその化合物からなる免疫化学的測定法によるエストラジオ−ル−３−サルフエ−ト−１７β−グルクロナイド測定用抗原 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17092583A JPS6061596A (ja) | 1983-09-16 | 1983-09-16 | 新規ステロイド化合物，その製造方法，及びその化合物からなる免疫化学的測定法によるエストラジオ−ル−３−サルフエ−ト−１７β−グルクロナイド測定用抗原 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6061596A true JPS6061596A (ja) | 1985-04-09 |
| JPH0432839B2 JPH0432839B2 (cs) | 1992-06-01 |
Family
ID=15913897
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17092583A Granted JPS6061596A (ja) | 1983-09-16 | 1983-09-16 | 新規ステロイド化合物，その製造方法，及びその化合物からなる免疫化学的測定法によるエストラジオ−ル−３−サルフエ−ト−１７β−グルクロナイド測定用抗原 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6061596A (cs) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1625854A1 (en) * | 2004-08-09 | 2006-02-15 | Deutsches Krebsforschungszentrum Stiftung des öffentlichen Rechts | Albumin conjugates containing a glucuronic linker |
-
1983
- 1983-09-16 JP JP17092583A patent/JPS6061596A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1625854A1 (en) * | 2004-08-09 | 2006-02-15 | Deutsches Krebsforschungszentrum Stiftung des öffentlichen Rechts | Albumin conjugates containing a glucuronic linker |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0432839B2 (cs) | 1992-06-01 |
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