JPS6224743B2 - - Google Patents
Info
- Publication number
- JPS6224743B2 JPS6224743B2 JP16883381A JP16883381A JPS6224743B2 JP S6224743 B2 JPS6224743 B2 JP S6224743B2 JP 16883381 A JP16883381 A JP 16883381A JP 16883381 A JP16883381 A JP 16883381A JP S6224743 B2 JPS6224743 B2 JP S6224743B2
- Authority
- JP
- Japan
- Prior art keywords
- glucuronide
- oxoestriol
- diacetate
- bsa
- oxime
- 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
Links
- 239000000126 substance Substances 0.000 claims description 22
- 239000000427 antigen Substances 0.000 claims description 21
- 102000036639 antigens Human genes 0.000 claims description 21
- 108091007433 antigens Proteins 0.000 claims description 21
- UZKIAJMSMKLBQE-JRSYHJKYSA-N estriol 3-O-(beta-D-glucuronide) Chemical compound C([C@@H]1[C@@H](C2=CC=3)CC[C@]4([C@H]1C[C@@H](O)[C@@H]4O)C)CC2=CC=3O[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O UZKIAJMSMKLBQE-JRSYHJKYSA-N 0.000 claims description 16
- 238000004519 manufacturing process Methods 0.000 claims description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 150000002923 oximes Chemical class 0.000 claims description 3
- 239000001632 sodium acetate Substances 0.000 claims description 3
- 235000017281 sodium acetate Nutrition 0.000 claims description 3
- 108091003079 Bovine Serum Albumin Proteins 0.000 claims 2
- 229940098773 bovine serum albumin Drugs 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 1
- 238000000034 method Methods 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 230000009260 cross reactivity Effects 0.000 description 7
- 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 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 210000001124 body fluid Anatomy 0.000 description 6
- 239000010839 body fluid Substances 0.000 description 6
- 229960001348 estriol Drugs 0.000 description 6
- 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 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 150000003431 steroids Chemical class 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 238000003127 radioimmunoassay Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 230000002194 synthesizing effect Effects 0.000 description 5
- IAJILQKETJEXLJ-QTBDOELSSA-N aldehydo-D-glucuronic acid Chemical group O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-QTBDOELSSA-N 0.000 description 4
- 229940011871 estrogen Drugs 0.000 description 4
- 239000000262 estrogen Substances 0.000 description 4
- 229930182480 glucuronide Natural products 0.000 description 4
- 150000008134 glucuronides Chemical class 0.000 description 4
- 229940088597 hormone Drugs 0.000 description 4
- 239000005556 hormone Substances 0.000 description 4
- 230000003301 hydrolyzing effect Effects 0.000 description 4
- 108010078791 Carrier Proteins Proteins 0.000 description 3
- 102000014914 Carrier Proteins Human genes 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- UZKIAJMSMKLBQE-SUPAOECSSA-N (2s,3s,4s,5r)-6-[[(8r,9s,13s,14s,16r,17r)-16,17-dihydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound C([C@@H]1[C@@H](C2=CC=3)CC[C@]4([C@H]1C[C@@H](O)[C@@H]4O)C)CC2=CC=3OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O UZKIAJMSMKLBQE-SUPAOECSSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- FQYGGFDZJFIDPU-JRSYHJKYSA-N estriol 16-O-(beta-D-glucuronide) Chemical compound O([C@@H]1C[C@H]2[C@H]3[C@@H](C4=CC=C(O)C=C4CC3)CC[C@@]2([C@H]1O)C)[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O FQYGGFDZJFIDPU-JRSYHJKYSA-N 0.000 description 2
- FQYGGFDZJFIDPU-UHFFFAOYSA-N estriol 16alpha-beta-D-glucuronide Natural products OC1C2(C)CCC(C3=CC=C(O)C=C3CC3)C3C2CC1OC1OC(C(O)=O)C(O)C(O)C1O FQYGGFDZJFIDPU-UHFFFAOYSA-N 0.000 description 2
- 230000001900 immune effect Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000000691 measurement method Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- -1 steroid compound Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 210000002700 urine Anatomy 0.000 description 2
- JKKFKPJIXZFSSB-UHFFFAOYSA-N 1,3,5(10)-estratrien-17-one 3-sulfate Natural products OS(=O)(=O)OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 JKKFKPJIXZFSSB-UHFFFAOYSA-N 0.000 description 1
- BPFKSUPTSXDJBL-UHFFFAOYSA-N 2-(hydroxyamino)acetic acid;hydrochloride Chemical compound Cl.ONCC(O)=O BPFKSUPTSXDJBL-UHFFFAOYSA-N 0.000 description 1
- IXMIEQPWCAPGKV-UHFFFAOYSA-N 2-aminooxyacetic acid;hydrochloride Chemical compound Cl.NOCC(O)=O IXMIEQPWCAPGKV-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
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910000011 cadmium carbonate Inorganic materials 0.000 description 1
- GKDXQAKPHKQZSC-UHFFFAOYSA-L cadmium(2+);carbonate Chemical compound [Cd+2].[O-]C([O-])=O GKDXQAKPHKQZSC-UHFFFAOYSA-L 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 230000001268 conjugating effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- JKKFKPJIXZFSSB-CBZIJGRNSA-N estrone 3-sulfate Chemical compound OS(=O)(=O)OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 JKKFKPJIXZFSSB-CBZIJGRNSA-N 0.000 description 1
- 230000001605 fetal effect Effects 0.000 description 1
- 238000002795 fluorescence method Methods 0.000 description 1
- 229940097043 glucuronic acid Drugs 0.000 description 1
- 230000003053 immunization Effects 0.000 description 1
- 238000002649 immunization Methods 0.000 description 1
- 238000003018 immunoassay Methods 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 230000003169 placental effect Effects 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003270 steroid hormone Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 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
- G01N33/74—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving hormones or other non-cytokine intercellular protein regulatory factors such as growth factors, including receptors to hormones and growth factors
- G01N33/743—Steroid hormones
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Chemical & Material Sciences (AREA)
- Biomedical Technology (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Microbiology (AREA)
- Analytical Chemistry (AREA)
- Biotechnology (AREA)
- Endocrinology (AREA)
- Food Science & Technology (AREA)
- Medicinal Chemistry (AREA)
- Physics & Mathematics (AREA)
- Cell Biology (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Steroid Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16883381A JPS5871459A (ja) | 1981-10-23 | 1981-10-23 | エストリオ−ル−３−グルクロナイド測定用抗原およびその製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16883381A JPS5871459A (ja) | 1981-10-23 | 1981-10-23 | エストリオ−ル−３−グルクロナイド測定用抗原およびその製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5871459A JPS5871459A (ja) | 1983-04-28 |
| JPS6224743B2 true JPS6224743B2 (enrdf_load_stackoverflow) | 1987-05-29 |
Family
ID=15875360
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16883381A Granted JPS5871459A (ja) | 1981-10-23 | 1981-10-23 | エストリオ−ル−３−グルクロナイド測定用抗原およびその製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5871459A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5854009A (en) * | 1995-09-19 | 1998-12-29 | Immuna Care Corporation | Method of detecting estrogen-sensitive pathologies |
-
1981
- 1981-10-23 JP JP16883381A patent/JPS5871459A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5871459A (ja) | 1983-04-28 |
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