JP4620061B2 - フェニルホスフェートの木炭による安定化 - Google Patents
フェニルホスフェートの木炭による安定化 Download PDFInfo
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- JP4620061B2 JP4620061B2 JP2006542699A JP2006542699A JP4620061B2 JP 4620061 B2 JP4620061 B2 JP 4620061B2 JP 2006542699 A JP2006542699 A JP 2006542699A JP 2006542699 A JP2006542699 A JP 2006542699A JP 4620061 B2 JP4620061 B2 JP 4620061B2
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- JP
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- Prior art keywords
- phenyl phosphate
- charcoal
- solubilized
- phosphate
- solubilized phenyl
- 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 - Fee Related
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- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 title claims description 302
- 239000003610 charcoal Substances 0.000 title claims description 215
- 230000006641 stabilisation Effects 0.000 title claims description 6
- 238000011105 stabilization Methods 0.000 title claims description 6
- XZKIHKMTEMTJQX-UHFFFAOYSA-N 4-Nitrophenyl Phosphate Chemical group OP(O)(=O)OC1=CC=C([N+]([O-])=O)C=C1 XZKIHKMTEMTJQX-UHFFFAOYSA-N 0.000 claims description 105
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 72
- 238000002835 absorbance Methods 0.000 claims description 58
- 239000000243 solution Substances 0.000 claims description 51
- 102000004190 Enzymes Human genes 0.000 claims description 45
- 108090000790 Enzymes Proteins 0.000 claims description 45
- 238000000034 method Methods 0.000 claims description 44
- 239000000758 substrate Substances 0.000 claims description 43
- 230000000694 effects Effects 0.000 claims description 37
- 230000000087 stabilizing effect Effects 0.000 claims description 37
- 230000007071 enzymatic hydrolysis Effects 0.000 claims description 36
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 claims description 36
- 239000000872 buffer Substances 0.000 claims description 33
- 238000004064 recycling Methods 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 27
- 102000002260 Alkaline Phosphatase Human genes 0.000 claims description 22
- 108020004774 Alkaline Phosphatase Proteins 0.000 claims description 22
- 239000003153 chemical reaction reagent Substances 0.000 claims description 17
- 102000004160 Phosphoric Monoester Hydrolases Human genes 0.000 claims description 16
- 108090000608 Phosphoric Monoester Hydrolases Proteins 0.000 claims description 16
- 102000013563 Acid Phosphatase Human genes 0.000 claims description 15
- 108010051457 Acid Phosphatase Proteins 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 14
- 238000001952 enzyme assay Methods 0.000 claims description 12
- GZCWLCBFPRFLKL-UHFFFAOYSA-N 1-prop-2-ynoxypropan-2-ol Chemical compound CC(O)COCC#C GZCWLCBFPRFLKL-UHFFFAOYSA-N 0.000 claims description 10
- 239000008188 pellet Substances 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 239000007983 Tris buffer Substances 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 150000002681 magnesium compounds Chemical class 0.000 claims description 6
- OWMVSZAMULFTJU-UHFFFAOYSA-N bis-tris Chemical compound OCCN(CCO)C(CO)(CO)CO OWMVSZAMULFTJU-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000002775 capsule Substances 0.000 claims description 4
- 239000006260 foam Substances 0.000 claims description 3
- 230000003381 solubilizing effect Effects 0.000 claims description 3
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 238000007789 sealing Methods 0.000 claims description 2
- 101150035093 AMPD gene Proteins 0.000 claims 1
- 239000003125 aqueous solvent Substances 0.000 claims 1
- 239000000523 sample Substances 0.000 description 26
- 238000003860 storage Methods 0.000 description 16
- 238000003556 assay Methods 0.000 description 13
- VLTINPRVNHVFLH-UHFFFAOYSA-N 3-amino-2-methylprop-1-ene-1,1-diol Chemical compound NCC(C)=C(O)O VLTINPRVNHVFLH-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000002965 ELISA Methods 0.000 description 7
- -1 PNPP is freeze-dried Chemical class 0.000 description 7
- UDMBCSSLTHHNCD-KQYNXXCUSA-N adenosine 5'-monophosphate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O UDMBCSSLTHHNCD-KQYNXXCUSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 7
- 230000007062 hydrolysis Effects 0.000 description 7
- 238000006460 hydrolysis reaction Methods 0.000 description 7
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 6
- 210000002966 serum Anatomy 0.000 description 6
- FTOAOBMCPZCFFF-UHFFFAOYSA-N 5,5-diethylbarbituric acid Chemical compound CCC1(CC)C(=O)NC(=O)NC1=O FTOAOBMCPZCFFF-UHFFFAOYSA-N 0.000 description 5
- 229910019142 PO4 Inorganic materials 0.000 description 5
- 239000007853 buffer solution Substances 0.000 description 5
- 238000000502 dialysis Methods 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 238000004806 packaging method and process Methods 0.000 description 5
- 235000021317 phosphate Nutrition 0.000 description 5
- 150000003014 phosphoric acid esters Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000012491 analyte Substances 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 108090000765 processed proteins & peptides Proteins 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 3
- DVLFYONBTKHTER-UHFFFAOYSA-N 3-(N-morpholino)propanesulfonic acid Chemical compound OS(=O)(=O)CCCN1CCOCC1 DVLFYONBTKHTER-UHFFFAOYSA-N 0.000 description 3
- 239000004471 Glycine Substances 0.000 description 3
- 102000004157 Hydrolases Human genes 0.000 description 3
- 108090000604 Hydrolases Proteins 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- FSVCELGFZIQNCK-UHFFFAOYSA-N N,N-bis(2-hydroxyethyl)glycine Chemical compound OCCN(CCO)CC(O)=O FSVCELGFZIQNCK-UHFFFAOYSA-N 0.000 description 3
- MKWKNSIESPFAQN-UHFFFAOYSA-N N-cyclohexyl-2-aminoethanesulfonic acid Chemical compound OS(=O)(=O)CCNC1CCCCC1 MKWKNSIESPFAQN-UHFFFAOYSA-N 0.000 description 3
- JOCBASBOOFNAJA-UHFFFAOYSA-N N-tris(hydroxymethyl)methyl-2-aminoethanesulfonic acid Chemical compound OCC(CO)(CO)NCCS(O)(=O)=O JOCBASBOOFNAJA-UHFFFAOYSA-N 0.000 description 3
- SEQKRHFRPICQDD-UHFFFAOYSA-N N-tris(hydroxymethyl)methylglycine Chemical compound OCC(CO)(CO)[NH2+]CC([O-])=O SEQKRHFRPICQDD-UHFFFAOYSA-N 0.000 description 3
- 229920002274 Nalgene Polymers 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003929 acidic solution Substances 0.000 description 3
- 229960002319 barbital Drugs 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 239000006172 buffering agent Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000006911 enzymatic reaction Methods 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 230000007774 longterm Effects 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
- 102000004196 processed proteins & peptides Human genes 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- BTJIUGUIPKRLHP-UHFFFAOYSA-M 4-nitrophenolate Chemical compound [O-]C1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-M 0.000 description 2
- XZKIHKMTEMTJQX-UHFFFAOYSA-L 4-nitrophenyl phosphate(2-) Chemical compound [O-][N+](=O)C1=CC=C(OP([O-])([O-])=O)C=C1 XZKIHKMTEMTJQX-UHFFFAOYSA-L 0.000 description 2
- 239000008000 CHES buffer Substances 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 108010008488 Glycylglycine Proteins 0.000 description 2
- 239000007995 HEPES buffer Substances 0.000 description 2
- 239000007993 MOPS buffer Substances 0.000 description 2
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 2
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 2
- UZMAPBJVXOGOFT-UHFFFAOYSA-N Syringetin Natural products COC1=C(O)C(OC)=CC(C2=C(C(=O)C3=C(O)C=C(O)C=C3O2)O)=C1 UZMAPBJVXOGOFT-UHFFFAOYSA-N 0.000 description 2
- 239000007994 TES buffer Substances 0.000 description 2
- 239000007997 Tricine buffer Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000010306 acid treatment Methods 0.000 description 2
- 239000012062 aqueous buffer Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000003637 basic solution Substances 0.000 description 2
- 239000007998 bicine buffer Substances 0.000 description 2
- 210000000988 bone and bone Anatomy 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000007398 colorimetric assay Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- KCFYHBSOLOXZIF-UHFFFAOYSA-N dihydrochrysin Natural products COC1=C(O)C(OC)=CC(C2OC3=CC(O)=CC(O)=C3C(=O)C2)=C1 KCFYHBSOLOXZIF-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000003366 endpoint assay Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
- YMAWOPBAYDPSLA-UHFFFAOYSA-N glycylglycine Chemical compound [NH3+]CC(=O)NCC([O-])=O YMAWOPBAYDPSLA-UHFFFAOYSA-N 0.000 description 2
- 238000003018 immunoassay Methods 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910001425 magnesium ion Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000008055 phosphate buffer solution Substances 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 238000005057 refrigeration Methods 0.000 description 2
- 238000001223 reverse osmosis Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 210000002700 urine Anatomy 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical class C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- BCHIXGBGRHLSBE-UHFFFAOYSA-N (4-methyl-2-oxochromen-7-yl) dihydrogen phosphate Chemical compound C1=C(OP(O)(O)=O)C=CC2=C1OC(=O)C=C2C BCHIXGBGRHLSBE-UHFFFAOYSA-N 0.000 description 1
- YHBAZQDEMYQPJL-UHFFFAOYSA-N 2-[(2-aminoacetyl)amino]acetic acid;hydron;chloride Chemical compound Cl.NCC(=O)NCC(O)=O YHBAZQDEMYQPJL-UHFFFAOYSA-N 0.000 description 1
- MLONYBFKXHEPCD-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(N)(CO)CO.OCC(N)(CO)CO MLONYBFKXHEPCD-UHFFFAOYSA-N 0.000 description 1
- 229940058020 2-amino-2-methyl-1-propanol Drugs 0.000 description 1
- CPBJMKMKNCRKQB-UHFFFAOYSA-N 3,3-bis(4-hydroxy-3-methylphenyl)-2-benzofuran-1-one Chemical compound C1=C(O)C(C)=CC(C2(C3=CC=CC=C3C(=O)O2)C=2C=C(C)C(O)=CC=2)=C1 CPBJMKMKNCRKQB-UHFFFAOYSA-N 0.000 description 1
- 208000020084 Bone disease Diseases 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- 239000008001 CAPS buffer Substances 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical class C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- 102000045595 Phosphoprotein Phosphatases Human genes 0.000 description 1
- 108700019535 Phosphoprotein Phosphatases Proteins 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 206010060862 Prostate cancer Diseases 0.000 description 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
- 238000011111 UV-scan method Methods 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000004855 amber Substances 0.000 description 1
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 1
- 210000000013 bile duct Anatomy 0.000 description 1
- 239000012472 biological sample Substances 0.000 description 1
- 210000001124 body fluid Anatomy 0.000 description 1
- 239000010839 body fluid Substances 0.000 description 1
- 239000008366 buffered solution Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000002967 competitive immunoassay Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000012228 culture supernatant Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000002405 diagnostic procedure Methods 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 238000007824 enzymatic assay Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229940043257 glycylglycine Drugs 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 230000003100 immobilizing effect Effects 0.000 description 1
- 238000001114 immunoprecipitation Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 208000019423 liver disease Diseases 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- ZHCAAFJSYLFLPX-UHFFFAOYSA-N nitrocyclohexatriene Chemical group [O-][N+](=O)C1=CC=C=C[CH]1 ZHCAAFJSYLFLPX-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 210000002826 placenta Anatomy 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 238000003908 quality control method Methods 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 239000002901 radioactive waste Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011265 semifinished product Substances 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- 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)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3834—Aromatic acids (P-C aromatic linkage)
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
- C12Q1/34—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving hydrolase
- C12Q1/42—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving hydrolase involving phosphatase
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/10—Composition for standardization, calibration, simulation, stabilization, preparation or preservation; processes of use in preparation for chemical testing
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/23—Carbon containing
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/23—Carbon containing
- Y10T436/235—In an aqueous solution [e.g., TOC, etc.]
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/25—Chemistry: analytical and immunological testing including sample preparation
- Y10T436/2525—Stabilizing or preserving
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Immunology (AREA)
- Biotechnology (AREA)
- Biophysics (AREA)
- Microbiology (AREA)
- Analytical Chemistry (AREA)
- Physics & Mathematics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Enzymes And Modification Thereof (AREA)
- Sampling And Sample Adjustment (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/727,537 US7001717B2 (en) | 2003-12-05 | 2003-12-05 | Charcoal stabilization of phenyl phosphates |
| PCT/US2004/040177 WO2005056816A1 (en) | 2003-12-05 | 2004-12-02 | Charcoal stabilization of phenyl phosphates |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010075380A Division JP4620172B2 (ja) | 2003-12-05 | 2010-03-29 | フェニルホスフェートの木炭による安定化 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007512843A JP2007512843A (ja) | 2007-05-24 |
| JP2007512843A5 JP2007512843A5 (https=) | 2010-04-22 |
| JP4620061B2 true JP4620061B2 (ja) | 2011-01-26 |
Family
ID=34633507
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006542699A Expired - Fee Related JP4620061B2 (ja) | 2003-12-05 | 2004-12-02 | フェニルホスフェートの木炭による安定化 |
| JP2010075380A Expired - Fee Related JP4620172B2 (ja) | 2003-12-05 | 2010-03-29 | フェニルホスフェートの木炭による安定化 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010075380A Expired - Fee Related JP4620172B2 (ja) | 2003-12-05 | 2010-03-29 | フェニルホスフェートの木炭による安定化 |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US7001717B2 (https=) |
| EP (1) | EP1709186B1 (https=) |
| JP (2) | JP4620061B2 (https=) |
| AU (1) | AU2004297569A1 (https=) |
| CA (1) | CA2548530C (https=) |
| NZ (1) | NZ548219A (https=) |
| WO (1) | WO2005056816A1 (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20220064861A (ko) * | 2019-09-17 | 2022-05-19 | 노바 바이오메디컬 코포레이션 | 혈액 중 간 효소 수준을 측정하기 위한 시스템 및 방법 |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1958210A (en) | 1932-07-01 | 1934-05-08 | Kavalco Products Inc | Method of making aryl phosphates and product thereof |
| US3951859A (en) | 1972-12-30 | 1976-04-20 | Toyo Jozo Co., Ltd. | Molecular sieving particle and preparation thereof |
| DE2341294C3 (de) | 1973-08-16 | 1981-12-24 | Bayer Ag, 5090 Leverkusen | Polyolgemische |
| US4042335A (en) | 1975-07-23 | 1977-08-16 | Eastman Kodak Company | Integral element for analysis of liquids |
| US4157280A (en) | 1975-09-29 | 1979-06-05 | Cordis Corporation | Test set for detecting the presence of antigens associated with hepatitis |
| US4028465A (en) | 1975-11-10 | 1977-06-07 | Bio-Rad Laboratories | Assay method for serum folate |
| US4372874A (en) | 1976-09-13 | 1983-02-08 | Modrovich Ivan Endre | Stabilization of hydrolysis prone labile organic reagents in liquid media |
| US4132598A (en) | 1977-06-03 | 1979-01-02 | Modrovich Ivan Endre | Stabilized liquid phosphate containing diagnostic compositions and method of preparing same |
| US4594249A (en) | 1985-06-14 | 1986-06-10 | 21St Century Marketing, Inc. | Method of altering intoxicating effects of alcohol |
| JPH0379601A (ja) * | 1989-03-24 | 1991-04-04 | Shinkoujin Kasei Kk | 高機能性再生セルロース組成物 |
| US5508182A (en) * | 1991-02-13 | 1996-04-16 | Schneider; Manfred P. | Esterification of hydrophilic polyols by adsorption onto a solid support and employing a substrate-immiscible solvent |
| BE1006432A3 (fr) * | 1992-12-02 | 1994-08-23 | Solvay | Procede de purification de 1,1-difluoroethane. |
| GB9422991D0 (en) * | 1994-11-15 | 1995-01-04 | Cortecs Ltd | Analytical method |
| US5464560A (en) | 1995-04-06 | 1995-11-07 | Bayer Corporation | Foam-forming mixtures with decreased decomposition of hydrohalocarbon blowing agents |
| US6177599B1 (en) * | 1995-11-17 | 2001-01-23 | Oxy Vinyls, L.P. | Method for reducing formation of polychlorinated aromatic compounds during oxychlorination of C1-C3 hydrocarbons |
| US5750812A (en) * | 1995-12-28 | 1998-05-12 | The Geon Company | Method for reducing formation of polychlorinated aromatic compounds during air oxychlorination of C1 -C3 Hydrocarbons |
| EP0816514B1 (en) | 1996-06-24 | 2003-04-09 | Tosoh Corporation | Enzyme substrate |
| DE19632432A1 (de) | 1996-08-12 | 1998-02-19 | Boehringer Mannheim Gmbh | Stabile Mischung zum Nachweis alkalischer Phosphatase mit einem Salz der o-Kresolphthaleinmonophosphorsäure |
| JP3677432B2 (ja) * | 2000-04-13 | 2005-08-03 | 松下電器産業株式会社 | 電気湯沸かし器 |
| US6887714B2 (en) | 2000-10-16 | 2005-05-03 | Board Of Trustees Of The University Of Arkansas, N.A. | Microvolume immunoabsorbant assays with amplified electrochemical detection |
-
2003
- 2003-12-05 US US10/727,537 patent/US7001717B2/en not_active Expired - Lifetime
-
2004
- 2004-12-02 EP EP04812640.3A patent/EP1709186B1/en not_active Expired - Lifetime
- 2004-12-02 WO PCT/US2004/040177 patent/WO2005056816A1/en not_active Ceased
- 2004-12-02 NZ NZ548219A patent/NZ548219A/en unknown
- 2004-12-02 JP JP2006542699A patent/JP4620061B2/ja not_active Expired - Fee Related
- 2004-12-02 AU AU2004297569A patent/AU2004297569A1/en not_active Abandoned
- 2004-12-02 CA CA2548530A patent/CA2548530C/en not_active Expired - Lifetime
-
2005
- 2005-11-01 US US11/262,715 patent/US7214481B2/en not_active Expired - Fee Related
-
2010
- 2010-03-29 JP JP2010075380A patent/JP4620172B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2010187684A (ja) | 2010-09-02 |
| AU2004297569A1 (en) | 2005-06-23 |
| NZ548219A (en) | 2009-02-28 |
| WO2005056816A1 (en) | 2005-06-23 |
| EP1709186B1 (en) | 2013-04-24 |
| CA2548530C (en) | 2014-08-12 |
| US20050124024A1 (en) | 2005-06-09 |
| JP2007512843A (ja) | 2007-05-24 |
| US20060063220A1 (en) | 2006-03-23 |
| US7001717B2 (en) | 2006-02-21 |
| EP1709186A1 (en) | 2006-10-11 |
| JP4620172B2 (ja) | 2011-01-26 |
| EP1709186A4 (en) | 2009-01-14 |
| CA2548530A1 (en) | 2005-06-23 |
| US7214481B2 (en) | 2007-05-08 |
| HK1099565A1 (en) | 2007-08-17 |
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