CH641569A5 - Procede et reactif pour determiner un ligand dans un echantillon. - Google Patents
Procede et reactif pour determiner un ligand dans un echantillon. Download PDFInfo
- Publication number
- CH641569A5 CH641569A5 CH87780A CH87780A CH641569A5 CH 641569 A5 CH641569 A5 CH 641569A5 CH 87780 A CH87780 A CH 87780A CH 87780 A CH87780 A CH 87780A CH 641569 A5 CH641569 A5 CH 641569A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- corresponds
- analytical reagent
- reagent according
- enzyme
- Prior art date
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- 239000003446 ligand Substances 0.000 title claims description 57
- 239000003153 chemical reaction reagent Substances 0.000 title claims description 53
- 238000000034 method Methods 0.000 title claims description 49
- 150000001875 compounds Chemical class 0.000 claims description 62
- 102000004190 Enzymes Human genes 0.000 claims description 47
- 108090000790 Enzymes Proteins 0.000 claims description 47
- 229940088598 enzyme Drugs 0.000 claims description 47
- -1 alkyl radical Chemical class 0.000 claims description 41
- 239000002532 enzyme inhibitor Substances 0.000 claims description 41
- 230000002427 irreversible effect Effects 0.000 claims description 41
- 210000002966 serum Anatomy 0.000 claims description 35
- 229940125532 enzyme inhibitor Drugs 0.000 claims description 34
- 102100033639 Acetylcholinesterase Human genes 0.000 claims description 28
- 108010022752 Acetylcholinesterase Proteins 0.000 claims description 28
- 229940022698 acetylcholinesterase Drugs 0.000 claims description 28
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 239000000758 substrate Substances 0.000 claims description 21
- 102000004169 proteins and genes Human genes 0.000 claims description 18
- 108090000623 proteins and genes Proteins 0.000 claims description 18
- 230000002255 enzymatic effect Effects 0.000 claims description 14
- 102000023732 binding proteins Human genes 0.000 claims description 13
- 108091008324 binding proteins Proteins 0.000 claims description 13
- 239000003112 inhibitor Substances 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 238000002156 mixing Methods 0.000 claims description 9
- GFFIJCYHQYHUHB-UHFFFAOYSA-N 2-acetylsulfanylethyl(trimethyl)azanium Chemical group CC(=O)SCC[N+](C)(C)C GFFIJCYHQYHUHB-UHFFFAOYSA-N 0.000 claims description 5
- 108090000322 Cholinesterases Proteins 0.000 claims description 5
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 5
- 229940048961 cholinesterase Drugs 0.000 claims description 5
- CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 claims description 4
- 229930182566 Gentamicin Natural products 0.000 claims description 4
- 150000002500 ions Chemical class 0.000 claims description 4
- SLAMLWHELXOEJZ-UHFFFAOYSA-N 2-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-N 0.000 claims description 3
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 3
- 230000000295 complement effect Effects 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 230000000415 inactivating effect Effects 0.000 claims description 2
- UJTMLNARSPORHR-UHFFFAOYSA-N oc2h5 Chemical compound C=C=[O+] UJTMLNARSPORHR-UHFFFAOYSA-N 0.000 claims 2
- 102000003914 Cholinesterases Human genes 0.000 claims 1
- 229930003779 Vitamin B12 Natural products 0.000 claims 1
- AGVAZMGAQJOSFJ-WZHZPDAFSA-M cobalt(2+);[(2r,3s,4r,5s)-5-(5,6-dimethylbenzimidazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] [(2r)-1-[3-[(1r,2r,3r,4z,7s,9z,12s,13s,14z,17s,18s,19r)-2,13,18-tris(2-amino-2-oxoethyl)-7,12,17-tris(3-amino-3-oxopropyl)-3,5,8,8,13,15,18,19-octamethyl-2 Chemical compound [Co+2].N#[C-].[N-]([C@@H]1[C@H](CC(N)=O)[C@@]2(C)CCC(=O)NC[C@@H](C)OP(O)(=O)O[C@H]3[C@H]([C@H](O[C@@H]3CO)N3C4=CC(C)=C(C)C=C4N=C3)O)\C2=C(C)/C([C@H](C\2(C)C)CCC(N)=O)=N/C/2=C\C([C@H]([C@@]/2(CC(N)=O)C)CCC(N)=O)=N\C\2=C(C)/C2=N[C@]1(C)[C@@](C)(CC(N)=O)[C@@H]2CCC(N)=O AGVAZMGAQJOSFJ-WZHZPDAFSA-M 0.000 claims 1
- 229960002518 gentamicin Drugs 0.000 claims 1
- 238000012544 monitoring process Methods 0.000 claims 1
- 238000002798 spectrophotometry method Methods 0.000 claims 1
- 239000011715 vitamin B12 Substances 0.000 claims 1
- 235000019163 vitamin B12 Nutrition 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 162
- 239000000243 solution Substances 0.000 description 85
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 48
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 40
- 239000002904 solvent Substances 0.000 description 38
- 239000000203 mixture Substances 0.000 description 36
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 31
- 239000000872 buffer Substances 0.000 description 28
- 239000000523 sample Substances 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 229910019142 PO4 Inorganic materials 0.000 description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 24
- 239000010452 phosphate Substances 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 23
- 230000002829 reductive effect Effects 0.000 description 23
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 22
- 108010007979 Glycocholic Acid Proteins 0.000 description 21
- RFDAIACWWDREDC-UHFFFAOYSA-N Na salt-Glycocholic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(=O)NCC(O)=O)C)C1(C)C(O)C2 RFDAIACWWDREDC-UHFFFAOYSA-N 0.000 description 21
- RFDAIACWWDREDC-FRVQLJSFSA-N glycocholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 RFDAIACWWDREDC-FRVQLJSFSA-N 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 21
- 229960005156 digoxin Drugs 0.000 description 20
- LTMHDMANZUZIPE-AMTYYWEZSA-N Digoxin Natural products O([C@H]1[C@H](C)O[C@H](O[C@@H]2C[C@@H]3[C@@](C)([C@@H]4[C@H]([C@]5(O)[C@](C)([C@H](O)C4)[C@H](C4=CC(=O)OC4)CC5)CC3)CC2)C[C@@H]1O)[C@H]1O[C@H](C)[C@@H](O[C@H]2O[C@@H](C)[C@H](O)[C@@H](O)C2)[C@@H](O)C1 LTMHDMANZUZIPE-AMTYYWEZSA-N 0.000 description 18
- 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 18
- 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 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 108010010803 Gelatin Proteins 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 239000008273 gelatin Substances 0.000 description 15
- 229920000159 gelatin Polymers 0.000 description 15
- 235000019322 gelatine Nutrition 0.000 description 15
- 235000011852 gelatine desserts Nutrition 0.000 description 15
- 230000005764 inhibitory process Effects 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
- 238000001704 evaporation Methods 0.000 description 14
- 230000008020 evaporation Effects 0.000 description 14
- 239000000741 silica gel Substances 0.000 description 14
- 229910002027 silica gel Inorganic materials 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 239000000499 gel Substances 0.000 description 13
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 13
- 235000019341 magnesium sulphate Nutrition 0.000 description 13
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 12
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- 238000001914 filtration Methods 0.000 description 10
- 238000011534 incubation Methods 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
- 239000012224 working solution Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- 239000011780 sodium chloride Substances 0.000 description 9
- 102100032404 Cholinesterase Human genes 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 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 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 7
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 7
- 238000004587 chromatography analysis Methods 0.000 description 7
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 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 6
- XXNRHOAJIUSMOQ-UHFFFAOYSA-N Methylphosphonothioic acid o-ethyl ester Chemical compound CCOP(C)(O)=S XXNRHOAJIUSMOQ-UHFFFAOYSA-N 0.000 description 6
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- 238000002835 absorbance Methods 0.000 description 6
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 6
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- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 description 5
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- BHQCQFFYRZLCQQ-UHFFFAOYSA-N (3alpha,5alpha,7alpha,12alpha)-3,7,12-trihydroxy-cholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 BHQCQFFYRZLCQQ-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- 108010053652 Butyrylcholinesterase Proteins 0.000 description 4
- 239000004380 Cholic acid Substances 0.000 description 4
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 4
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- BHQCQFFYRZLCQQ-OELDTZBJSA-N cholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 BHQCQFFYRZLCQQ-OELDTZBJSA-N 0.000 description 4
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- IZDROVVXIHRYMH-UHFFFAOYSA-N methanesulfonic anhydride Chemical compound CS(=O)(=O)OS(C)(=O)=O IZDROVVXIHRYMH-UHFFFAOYSA-N 0.000 description 4
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- XVXIYRNLQGEXIZ-UHFFFAOYSA-N butoxy-hydroxy-methyl-sulfanylidene-$l^{5}-phosphane Chemical compound CCCCOP(C)(O)=S XVXIYRNLQGEXIZ-UHFFFAOYSA-N 0.000 description 1
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- 238000011088 calibration curve Methods 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 210000001175 cerebrospinal fluid Anatomy 0.000 description 1
- RUDATBOHQWOJDD-BSWAIDMHSA-N chenodeoxycholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 RUDATBOHQWOJDD-BSWAIDMHSA-N 0.000 description 1
- 229960001091 chenodeoxycholic acid Drugs 0.000 description 1
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- 125000004093 cyano group Chemical group *C#N 0.000 description 1
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- KXGVEGMKQFWNSR-LLQZFEROSA-N deoxycholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 KXGVEGMKQFWNSR-LLQZFEROSA-N 0.000 description 1
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- 238000010586 diagram Methods 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-O dicyclohexylazanium Chemical compound C1CCCCC1[NH2+]C1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-O 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
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- 239000000543 intermediate Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
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- 238000002955 isolation Methods 0.000 description 1
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- 238000002372 labelling Methods 0.000 description 1
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- 239000007788 liquid Substances 0.000 description 1
- SMEROWZSTRWXGI-HVATVPOCSA-N lithocholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 SMEROWZSTRWXGI-HVATVPOCSA-N 0.000 description 1
- MBXNQZHITVCSLJ-UHFFFAOYSA-N methyl fluorosulfonate Chemical compound COS(F)(=O)=O MBXNQZHITVCSLJ-UHFFFAOYSA-N 0.000 description 1
- KMLSFWQTQIKPFQ-UHFFFAOYSA-N methyl thiohypoiodite Chemical compound CSI KMLSFWQTQIKPFQ-UHFFFAOYSA-N 0.000 description 1
- UBLQIESZTDNNAO-UHFFFAOYSA-N n,n-diethylethanamine;phosphoric acid Chemical compound [O-]P([O-])([O-])=O.CC[NH+](CC)CC.CC[NH+](CC)CC.CC[NH+](CC)CC UBLQIESZTDNNAO-UHFFFAOYSA-N 0.000 description 1
- VGPBPWRBXBKGRE-UHFFFAOYSA-N n-(oxomethylidene)hydroxylamine Chemical compound ON=C=O VGPBPWRBXBKGRE-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229940127240 opiate Drugs 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
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- YFZOUMNUDGGHIW-UHFFFAOYSA-M p-chloromercuribenzoic acid Chemical class OC(=O)C1=CC=C([Hg]Cl)C=C1 YFZOUMNUDGGHIW-UHFFFAOYSA-M 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
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- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
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- 239000011591 potassium Substances 0.000 description 1
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- 239000000186 progesterone Substances 0.000 description 1
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- 239000011734 sodium Substances 0.000 description 1
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- 229960004025 sodium salicylate Drugs 0.000 description 1
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- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
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- FHXBAFXQVZOILS-OETIFKLTSA-N sulfoglycolithocholic acid Chemical compound C([C@H]1CC2)[C@H](OS(O)(=O)=O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCC(O)=O)C)[C@@]2(C)CC1 FHXBAFXQVZOILS-OETIFKLTSA-N 0.000 description 1
- 108700018664 sulfolithocholylglycine Proteins 0.000 description 1
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- 150000003456 sulfonamides Chemical class 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Chemical group 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 229960003604 testosterone Drugs 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- 229960004072 thrombin Drugs 0.000 description 1
- 229960002175 thyroglobulin Drugs 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- QDWJJTJNXAKQKD-UHFFFAOYSA-N trihexyphenidyl hydrochloride Chemical compound Cl.C1CCCCC1C(C=1C=CC=CC=1)(O)CCN1CCCCC1 QDWJJTJNXAKQKD-UHFFFAOYSA-N 0.000 description 1
- 229940035722 triiodothyronine Drugs 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- MSRILKIQRXUYCT-UHFFFAOYSA-M valproate semisodium Chemical compound [Na+].CCCC(C(O)=O)CCC.CCCC(C([O-])=O)CCC MSRILKIQRXUYCT-UHFFFAOYSA-M 0.000 description 1
- 229960000604 valproic acid Drugs 0.000 description 1
- 235000019156 vitamin B Nutrition 0.000 description 1
- 239000011720 vitamin B Substances 0.000 description 1
- 229940082632 vitamin b12 and folic acid Drugs 0.000 description 1
- 239000003039 volatile agent Substances 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
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
- G01N33/536—Immunoassay; Biospecific binding assay; Materials therefor with immune complex formed in liquid phase
- G01N33/542—Immunoassay; Biospecific binding assay; Materials therefor with immune complex formed in liquid phase with steric inhibition or signal modification, e.g. fluorescent quenching
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4075—Esters with hydroxyalkyl compounds
-
- 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
- G01N33/531—Production of immunochemical test materials
- G01N33/532—Production of labelled immunochemicals
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/81—Packaged device or kit
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/962—Prevention or removal of interfering materials or reactants or other treatment to enhance results, e.g. determining or preventing nonspecific binding
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S436/00—Chemistry: analytical and immunological testing
- Y10S436/825—Pretreatment for removal of interfering factors from sample
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Immunology (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Biomedical Technology (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Biotechnology (AREA)
- Cell Biology (AREA)
- Microbiology (AREA)
- Organic Chemistry (AREA)
- Food Science & Technology (AREA)
- Medicinal Chemistry (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Steroid Compounds (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/009,007 US4273866A (en) | 1979-02-05 | 1979-02-05 | Ligand analog-irreversible enzyme inhibitor conjugates and methods for use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH641569A5 true CH641569A5 (fr) | 1984-02-29 |
Family
ID=21735028
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH87780A CH641569A5 (fr) | 1979-02-05 | 1980-02-04 | Procede et reactif pour determiner un ligand dans un echantillon. |
Country Status (15)
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0040224A4 (en) * | 1979-11-19 | 1982-09-09 | Prince Charles Hospital Dev Ct | IMPROVED PROCESS FOR IMMUNOLOGICAL ANALYSIS OF NON-HOMOGENOUS ENZYMES. |
| DE3006709A1 (de) * | 1980-02-22 | 1981-08-27 | Hans A. Dipl.-Chem. Dr. 8000 München Thoma | Homogenes verfahren zur kompetitiven bestimmung von liganden |
| US4341865A (en) * | 1980-07-21 | 1982-07-27 | Abbott Laboratories | Determination of thyroxine binding globulin |
| US4849353A (en) * | 1980-09-30 | 1989-07-18 | Cornell Research Foundation, Inc. | Immunocapture of enzyme inhibitor, enzyme complexes and uses thereof |
| US4323647A (en) * | 1980-10-15 | 1982-04-06 | University Of Miami | Steric hindrance enzyme immunoassay |
| DE3100062A1 (de) * | 1981-01-02 | 1982-08-05 | Hans A. Dipl.-Chem. Dr. 8000 München Thoma | Homogenes verfahren zur bestimmung von liganden |
| DE3100061A1 (de) * | 1981-01-02 | 1982-08-05 | Hans A. Dipl.-Chem. Dr. 8000 München Thoma | Verfahren zur bestimmung von liganden mittels kompetitionsreaktion |
| EP0079489A1 (en) * | 1981-11-04 | 1983-05-25 | Miles Laboratories, Inc. | Methotrexate-labeled iodothyronine conjugates and method, reagent means and test device for the determination of iodothyronine in or iodothyronine uptake of a liquid sample |
| US4451652A (en) * | 1982-05-24 | 1984-05-29 | Abbott Laboratories | Substituted theophylline salts |
| US4472301A (en) * | 1982-05-27 | 1984-09-18 | Miles Laboratories, Inc. | Propranolol immunogen and antibodies |
| GB2135773B (en) * | 1983-01-31 | 1985-12-04 | Boots Celltech Diagnostics | Enzyme inhibitor labelled immunoassay |
| US4650751A (en) * | 1983-04-29 | 1987-03-17 | Technicon Instruments Corporation | Protected binding assay avoiding non-specific protein interference |
| US4550075A (en) * | 1983-06-22 | 1985-10-29 | Kallestad Laboratories, Inc. | Method for ligand determination utilizing an immunoassay monitorable by biotin-containing enzymes, and compositions therefor |
| JPS607362A (ja) * | 1983-06-27 | 1985-01-16 | Fujirebio Inc | 酵素を用いた抗原決定基具有物質の測定法 |
| US4629694A (en) * | 1983-07-12 | 1986-12-16 | Cornell Research Foundation, Inc. | Detecting and distinguishing between plasminogen activators |
| US4559173A (en) * | 1983-11-04 | 1985-12-17 | Abbott Laboratories | N-substituted dibenz[b,f]azepine salts |
| US4543412A (en) * | 1983-11-04 | 1985-09-24 | Abbott Laboratories | Phenobarbital enzyme inhibitors |
| IL73293A (en) * | 1983-11-04 | 1988-02-29 | Abbott Lab | Methyl 2-(alkanamidoalkylsulfonic)ethylthiophosphonate derivatives |
| DE4007048A1 (de) * | 1990-03-07 | 1991-09-12 | Hoechst Ag | N-acyl-aminoalkyl-2-hydroxyethylsulfide und ein verfahren zu ihrer herstellung |
| US5338663A (en) * | 1990-08-24 | 1994-08-16 | President And Fellows Of Harvard College | Method of identifying inhibitors of β-protein esterase activity |
| US5648462A (en) * | 1990-10-09 | 1997-07-15 | Setsuko Funakoshi | Peptide purification method using novel linker and solid-phase ligand |
| JP2552049B2 (ja) * | 1990-10-09 | 1996-11-06 | 舩越 節子 | 合成ペプチド精製方法およびこれに用いるリンカー、リンカー結合用固相担体 |
| JPH0737982B2 (ja) * | 1992-12-14 | 1995-04-26 | 元成 狩野 | 抗胆汁酸抗体およびこれを用いた糞便中の胆汁酸検査方法 |
| US5922703A (en) * | 1993-09-24 | 1999-07-13 | The Procter & Gamble Company | Urethane-containing aminosteroid compounds |
| CA2183562A1 (en) * | 1994-02-18 | 1995-08-24 | J. Peter Klein | Intracellular signalling mediators |
| US6811998B2 (en) * | 1999-06-25 | 2004-11-02 | Roche Diagnostics Operations, Inc. | Conjugates of uncompetitive inhibitors of inosine monophosphate dehydrogenase |
| CA2341263C (en) * | 1999-06-25 | 2006-08-01 | Roche Diagnostics Corporation | Enzyme inhibition immunoassay |
| US6524808B1 (en) * | 1999-06-25 | 2003-02-25 | Roche Diagnostics Corporation | Enzyme inhibition immunoassay |
| AU2003225022A1 (en) * | 2002-04-16 | 2003-11-03 | The Regents Of The University Of California | Ligand sensing fluorescent acetylcholinesterase for detection of organophosphate activity |
| AU2011206864B2 (en) | 2010-01-15 | 2013-12-19 | Suzhou Neupharma Co., Ltd. | Certain chemical entities, compositions, and methods |
| CN102656179B (zh) | 2010-08-28 | 2015-07-29 | 苏州润新生物科技有限公司 | 蟾蜍灵衍生物、其药物组合物及用途 |
| US9493503B2 (en) | 2011-02-02 | 2016-11-15 | Neupharma, Inc. | Certain chemical entities, compositions, and methods |
| US9676813B2 (en) | 2012-04-29 | 2017-06-13 | Neupharma, Inc. | Certain steroids and methods for using the same in the treatment of cancer |
| CN112114127A (zh) * | 2020-09-09 | 2020-12-22 | 武汉生之源生物科技股份有限公司 | 一种甘胆酸均相酶免疫测定试剂盒及其制备方法和应用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IN142734B (US08118993-20120221-C00002.png) * | 1975-04-28 | 1977-08-20 | Miles Lab | |
| NL7512939A (nl) * | 1975-11-04 | 1977-05-06 | Tno | Werkwijze en inrichtingen voor het aantonen en/of bepalen van alkylerende verbindingen, zoals mosterdgassen. |
| US4134792A (en) | 1976-12-06 | 1979-01-16 | Miles Laboratories, Inc. | Specific binding assay with an enzyme modulator as a labeling substance |
| GB1595101A (en) | 1977-03-15 | 1981-08-05 | Hoffmann La Roche | Enzyme modifier immunoassay |
| IT1105734B (it) * | 1977-07-14 | 1985-11-04 | Syva Co | Prova di legame di competizione di antienzima omogeneo |
-
1979
- 1979-02-05 US US06/009,007 patent/US4273866A/en not_active Expired - Lifetime
-
1980
- 1980-01-15 CA CA000343676A patent/CA1137077A/en not_active Expired
- 1980-01-21 AU AU54763/80A patent/AU528592B2/en not_active Ceased
- 1980-01-22 ZA ZA00800371A patent/ZA80371B/xx unknown
- 1980-01-28 GB GB8002743A patent/GB2043245B/en not_active Expired
- 1980-02-01 JP JP1011780A patent/JPS55104896A/ja active Pending
- 1980-02-01 SE SE8000843A patent/SE448259B/sv not_active IP Right Cessation
- 1980-02-01 AT AT0056080A patent/AT365781B/de not_active IP Right Cessation
- 1980-02-04 ES ES488263A patent/ES488263A0/es active Granted
- 1980-02-04 FR FR8002385A patent/FR2447966A1/fr active Granted
- 1980-02-04 NL NL8000698A patent/NL8000698A/nl not_active Application Discontinuation
- 1980-02-04 DE DE3003959A patent/DE3003959C2/de not_active Expired
- 1980-02-04 CH CH87780A patent/CH641569A5/fr not_active IP Right Cessation
- 1980-02-04 IT IT19675/80A patent/IT1130254B/it active
- 1980-02-05 BE BE0/199272A patent/BE881557A/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IT8019675A0 (it) | 1980-02-04 |
| BE881557A (fr) | 1980-08-05 |
| JPS55104896A (en) | 1980-08-11 |
| GB2043245B (en) | 1983-05-25 |
| ZA80371B (en) | 1981-03-25 |
| AU5476380A (en) | 1980-08-14 |
| ES8101647A1 (es) | 1980-12-16 |
| GB2043245A (en) | 1980-10-01 |
| NL8000698A (nl) | 1980-08-07 |
| ES488263A0 (es) | 1980-12-16 |
| FR2447966B1 (US08118993-20120221-C00002.png) | 1984-10-19 |
| CA1137077A (en) | 1982-12-07 |
| AU528592B2 (en) | 1983-05-05 |
| SE8000843L (sv) | 1980-08-06 |
| DE3003959A1 (de) | 1980-08-14 |
| IT1130254B (it) | 1986-06-11 |
| AT365781B (de) | 1982-02-10 |
| ATA56080A (de) | 1981-06-15 |
| SE448259B (sv) | 1987-02-02 |
| US4273866A (en) | 1981-06-16 |
| DE3003959C2 (de) | 1982-12-23 |
| FR2447966A1 (fr) | 1980-08-29 |
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| Date | Code | Title | Description |
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| PL | Patent ceased |