CS273162B2 - Diagnostic agent for glicosidases activity determination - Google Patents
Diagnostic agent for glicosidases activity determination Download PDFInfo
- Publication number
- CS273162B2 CS273162B2 CS206485A CS206485A CS273162B2 CS 273162 B2 CS273162 B2 CS 273162B2 CS 206485 A CS206485 A CS 206485A CS 206485 A CS206485 A CS 206485A CS 273162 B2 CS273162 B2 CS 273162B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- hydrogen
- group
- glycosides
- alkyl
- lower alkyl
- Prior art date
Links
- 230000000694 effects Effects 0.000 title claims abstract description 22
- 229940039227 diagnostic agent Drugs 0.000 title abstract description 5
- 239000000032 diagnostic agent Substances 0.000 title abstract description 5
- 102000005744 Glycoside Hydrolases Human genes 0.000 claims abstract description 27
- 108010031186 Glycoside Hydrolases Proteins 0.000 claims abstract description 27
- 150000002338 glycosides Chemical class 0.000 claims abstract description 24
- 229930182470 glycoside Natural products 0.000 claims abstract description 22
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- 239000007850 fluorescent dye Substances 0.000 claims abstract description 11
- HSSLDCABUXLXKM-UHFFFAOYSA-N resorufin Chemical class C1=CC(=O)C=C2OC3=CC(O)=CC=C3N=C21 HSSLDCABUXLXKM-UHFFFAOYSA-N 0.000 claims abstract description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 9
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 239000003593 chromogenic compound Substances 0.000 claims abstract description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 4
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 239000006172 buffering agent Substances 0.000 claims description 2
- 125000005518 carboxamido group Chemical group 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 239000000080 wetting agent Substances 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 102000004190 Enzymes Human genes 0.000 abstract description 21
- 108090000790 Enzymes Proteins 0.000 abstract description 21
- 150000001875 compounds Chemical class 0.000 abstract description 10
- 125000006239 protecting group Chemical group 0.000 abstract description 7
- 238000002360 preparation method Methods 0.000 abstract description 6
- 150000002772 monosaccharides Chemical class 0.000 abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 3
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 1
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 abstract 1
- 230000008030 elimination Effects 0.000 abstract 1
- 238000003379 elimination reaction Methods 0.000 abstract 1
- 229920001542 oligosaccharide Polymers 0.000 abstract 1
- 150000002482 oligosaccharides Chemical class 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 25
- 238000012360 testing method Methods 0.000 description 19
- 239000000758 substrate Substances 0.000 description 17
- 102000005936 beta-Galactosidase Human genes 0.000 description 16
- 108010005774 beta-Galactosidase Proteins 0.000 description 16
- 239000003153 chemical reaction reagent Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 230000002255 enzymatic effect Effects 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 238000003018 immunoassay Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000007853 buffer solution Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000000872 buffer Substances 0.000 description 5
- 150000001720 carbohydrates Chemical class 0.000 description 5
- 238000003776 cleavage reaction Methods 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 230000007017 scission Effects 0.000 description 5
- -1 1-naphthyl compound Chemical class 0.000 description 4
- TWCMVXMQHSVIOJ-UHFFFAOYSA-N Aglycone of yadanzioside D Natural products COC(=O)C12OCC34C(CC5C(=CC(O)C(O)C5(C)C3C(O)C1O)C)OC(=O)C(OC(=O)C)C24 TWCMVXMQHSVIOJ-UHFFFAOYSA-N 0.000 description 4
- PLMKQQMDOMTZGG-UHFFFAOYSA-N Astrantiagenin E-methylester Natural products CC12CCC(O)C(C)(CO)C1CCC1(C)C2CC=C2C3CC(C)(C)CCC3(C(=O)OC)CCC21C PLMKQQMDOMTZGG-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 235000014633 carbohydrates Nutrition 0.000 description 4
- PFOARMALXZGCHY-UHFFFAOYSA-N homoegonol Natural products C1=C(OC)C(OC)=CC=C1C1=CC2=CC(CCCO)=CC(OC)=C2O1 PFOARMALXZGCHY-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000008033 biological extinction Effects 0.000 description 3
- 238000005470 impregnation Methods 0.000 description 3
- PCKPVGOLPKLUHR-UHFFFAOYSA-N indoxyl Chemical group C1=CC=C2C(O)=CNC2=C1 PCKPVGOLPKLUHR-UHFFFAOYSA-N 0.000 description 3
- 238000012933 kinetic analysis Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- ZXSQEZNORDWBGZ-UHFFFAOYSA-N 1,3-dihydropyrrolo[2,3-b]pyridin-2-one Chemical compound C1=CN=C2NC(=O)CC2=C1 ZXSQEZNORDWBGZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- RLFWWDJHLFCNIJ-UHFFFAOYSA-N 4-aminoantipyrine Chemical compound CN1C(C)=C(N)C(=O)N1C1=CC=CC=C1 RLFWWDJHLFCNIJ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 239000007995 HEPES buffer Substances 0.000 description 2
- 108010093096 Immobilized Enzymes Proteins 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- 229930195725 Mannitol Natural products 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002250 absorbent Substances 0.000 description 2
- 230000002745 absorbent Effects 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 238000007421 fluorometric assay Methods 0.000 description 2
- 229940127121 immunoconjugate Drugs 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000000594 mannitol Substances 0.000 description 2
- 235000010355 mannitol Nutrition 0.000 description 2
- 150000002730 mercury Chemical class 0.000 description 2
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 2
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K potassium phosphate Substances [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- LKZMBDSASOBTPN-UHFFFAOYSA-L silver carbonate Substances [Ag].[O-]C([O-])=O LKZMBDSASOBTPN-UHFFFAOYSA-L 0.000 description 2
- 229910001958 silver carbonate Inorganic materials 0.000 description 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 235000010356 sorbitol Nutrition 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000012085 test solution Substances 0.000 description 2
- 235000010447 xylitol Nutrition 0.000 description 2
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- WQZGKKKJIJFFOK-SVZMEOIVSA-N (+)-Galactose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-SVZMEOIVSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- RMZNXRYIFGTWPF-UHFFFAOYSA-N 2-nitrosoacetic acid Chemical compound OC(=O)CN=O RMZNXRYIFGTWPF-UHFFFAOYSA-N 0.000 description 1
- RTKMFQOHBDVEBC-UHFFFAOYSA-N 3-bromo-3-buten-1-ol Chemical compound OCCC(Br)=C RTKMFQOHBDVEBC-UHFFFAOYSA-N 0.000 description 1
- IFBHRQDFSNCLOZ-YBXAARCKSA-N 4-nitrophenyl-beta-D-galactoside Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1OC1=CC=C([N+]([O-])=O)C=C1 IFBHRQDFSNCLOZ-YBXAARCKSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229930186217 Glycolipid Natural products 0.000 description 1
- 102000003886 Glycoproteins Human genes 0.000 description 1
- 108090000288 Glycoproteins Proteins 0.000 description 1
- 229920002683 Glycosaminoglycan Polymers 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- NEZJDVYDSZTRFS-YBXAARCKSA-N Phenylgalactoside Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1OC1=CC=CC=C1 NEZJDVYDSZTRFS-YBXAARCKSA-N 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 229940009098 aspartate Drugs 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- BQDSDRAVKYTTTH-UHFFFAOYSA-N barium(2+);methanolate Chemical compound [Ba+2].[O-]C.[O-]C BQDSDRAVKYTTTH-UHFFFAOYSA-N 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
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 230000023852 carbohydrate metabolic process Effects 0.000 description 1
- 235000021256 carbohydrate metabolism Nutrition 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000024245 cell differentiation Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical class O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- LIIALPBMIOVAHH-UHFFFAOYSA-N herniarin Chemical class C1=CC(=O)OC2=CC(OC)=CC=C21 LIIALPBMIOVAHH-UHFFFAOYSA-N 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000008105 immune reaction Effects 0.000 description 1
- 238000010324 immunological assay Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940075610 mercuric cyanide Drugs 0.000 description 1
- 229940101209 mercuric oxide Drugs 0.000 description 1
- BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 1
- NGYIMTKLQULBOO-UHFFFAOYSA-L mercury dibromide Chemical compound Br[Hg]Br NGYIMTKLQULBOO-UHFFFAOYSA-L 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000006225 natural substrate Substances 0.000 description 1
- RBXVOQPAMPBADW-UHFFFAOYSA-N nitrous acid;phenol Chemical class ON=O.OC1=CC=CC=C1 RBXVOQPAMPBADW-UHFFFAOYSA-N 0.000 description 1
- 230000036963 noncompetitive effect Effects 0.000 description 1
- 125000001209 o-nitrophenyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])[N+]([O-])=O 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000005691 oxidative coupling reaction Methods 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 238000005375 photometry Methods 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920006289 polycarbonate film Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- QRUBYZBWAOOHSV-UHFFFAOYSA-M silver trifluoromethanesulfonate Chemical compound [Ag+].[O-]S(=O)(=O)C(F)(F)F QRUBYZBWAOOHSV-UHFFFAOYSA-M 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
- C07H3/06—Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
- C07D265/36—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings condensed with one six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
- C07D265/38—[b, e]-condensed with two six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
-
- 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
-
- 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
- C12Q2334/00—O-linked chromogens for determinations of hydrolase enzymes, e.g. glycosidases, phosphatases, esterases
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Immunology (AREA)
- Biophysics (AREA)
- Microbiology (AREA)
- Analytical Chemistry (AREA)
- Physics & Mathematics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Saccharide Compounds (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Luminescent Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS298888A CS273184B2 (en) | 1984-03-29 | 1988-05-03 | Method of resorufin's derivative glycoside production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843411574 DE3411574A1 (de) | 1984-03-29 | 1984-03-29 | Glycoside von resorufin-derivaten, verfahren zu deren herstellung sowie deren verwendung zur bestimmung der aktivitaet von glycosidasen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS206485A2 CS206485A2 (en) | 1990-07-12 |
| CS273162B2 true CS273162B2 (en) | 1991-03-12 |
Family
ID=6231957
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS206485A CS273162B2 (en) | 1984-03-29 | 1985-03-22 | Diagnostic agent for glicosidases activity determination |
Country Status (15)
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3412939A1 (de) * | 1984-04-06 | 1985-10-17 | Behringwerke Ag, 3550 Marburg | Substrate fuer hydrolasen, verfahren zu ihrer herstellung und ihre verwendung |
| DE3534927A1 (de) * | 1985-10-01 | 1987-04-02 | Boehringer Mannheim Gmbh | Phosphate von resorufin-derivaten, verfahren zu deren herstellung sowie deren verwendung zur bestimmung der aktivitaet von phosphatasen |
| DE3629175A1 (de) * | 1986-08-28 | 1988-03-17 | Behringwerke Ag | Chromogene verbindungen, verfahren zu deren herstellung und ihre verwendung |
| US4810636A (en) * | 1986-12-09 | 1989-03-07 | Miles Inc. | Chromogenic acridinone enzyme substrates |
| DE3644401A1 (de) * | 1986-12-24 | 1988-07-07 | Boehringer Mannheim Gmbh | Neue hydrolase-substrate |
| EP0494704A3 (en) | 1987-04-10 | 1992-09-02 | The Flinders University Of South Australia | Method and composition for the determination of calcium ions in fluids |
| DE3732871A1 (de) * | 1987-09-30 | 1989-04-20 | Behringwerke Ag | Chromogene substrate |
| US4932871A (en) * | 1987-11-20 | 1990-06-12 | Miles Inc. | Rapid method for preparing chromogenic alpha-amylase substrate compounds at high preparative yields |
| DE3743908A1 (de) * | 1987-12-23 | 1989-07-06 | Boehringer Mannheim Gmbh | Neue oligoglucoside |
| JPH01211595A (ja) * | 1988-02-18 | 1989-08-24 | Kikkoman Corp | 新規Ｎ−アセチル−β−Ｄ−グルコサミン誘導体、その製法及びＮ−アセチル−β−Ｄ−グルコサミニダーゼ活性測定用試薬への利用 |
| US5151348A (en) * | 1988-12-23 | 1992-09-29 | E. I. Du Pont De Nemours And Company | Enzyme-linked immunoassay for measurement of cyclosporin a levels in whole blood samples |
| US5104980A (en) * | 1989-06-12 | 1992-04-14 | Miles Inc. | Chromogenic dibenzoxazepinone and dibenzothiazepinone enzyme substrates |
| KR100710561B1 (ko) * | 2000-07-12 | 2007-04-24 | 에스케이 주식회사 | 유류 제품 은닉 표지 물질 및 이를 검출하는 방법 |
| WO2002100843A1 (fr) * | 2001-06-13 | 2002-12-19 | Jianqing Lu | Composes phenoxazines, preparations les contenant et leurs utilisations medicinales |
| FR2854893B1 (fr) * | 2003-05-13 | 2006-07-07 | Biomerieux Sa | Nouveaux substrats enzymatiques derives de phenoxazinone et leur utilisation comme revelateur dans la detection de microorganismes a activite peptidase |
| FR2875242B1 (fr) * | 2004-09-10 | 2006-11-17 | Biomerieux Sa | Nouveaux substrats enzymatiques derives de phenoxazinone et leur utilisation comme revelateur dans la detection de microorganismes a activite peptidase |
| WO2016110378A1 (en) | 2015-01-09 | 2016-07-14 | Unilever Plc | Laundry treatment composition comprising a dye |
| EP3932995A1 (en) | 2020-07-04 | 2022-01-05 | Emulseo SAS | Novel fluorescent substrates and uses thereof in microfluidics |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3378463A (en) * | 1965-06-22 | 1968-04-16 | Army Usa | Method of measuring enzyme activity |
| US3391104A (en) * | 1966-11-14 | 1968-07-02 | Eastman Kodak Co | Light stabilized, poly-alpha-olefin plastic composition |
| US3950322A (en) * | 1973-08-27 | 1976-04-13 | Research Corporation | Fluorogenic substrate glycosides |
| DE2752501A1 (de) * | 1977-11-24 | 1979-05-31 | Kurt Prof Dr Wallenfels | Mit indikatorgruppen substituierte alpha-d-maltodextrine, verfahren zu deren herstellung und ihre verwendung zur bestimmung von glukosidasen und amylasen |
| US4406832A (en) * | 1981-09-03 | 1983-09-27 | Mallinckrodt, Inc. | Peptide-type substrates useful in the quantitative determination of endotoxin |
| NZ206795A (en) * | 1983-01-21 | 1987-08-31 | Merck Frosst Canada Inc | Phenothiazines, analogues and pharmaceutical compositions |
-
1984
- 1984-03-29 DE DE19843411574 patent/DE3411574A1/de not_active Withdrawn
-
1985
- 1985-03-22 CS CS206485A patent/CS273162B2/cs unknown
- 1985-03-25 AT AT85103496T patent/ATE66929T1/de not_active IP Right Cessation
- 1985-03-25 DE DE8585103496T patent/DE3583954D1/de not_active Expired - Lifetime
- 1985-03-25 EP EP85103496A patent/EP0156347B1/de not_active Expired - Lifetime
- 1985-03-26 AU AU40375/85A patent/AU550958B2/en not_active Ceased
- 1985-03-26 ES ES541589A patent/ES541589A0/es active Granted
- 1985-03-27 DD DD85274494A patent/DD235648A5/de not_active IP Right Cessation
- 1985-03-28 ZA ZA852333A patent/ZA852333B/xx unknown
- 1985-03-28 HU HU851183A patent/HU198734B/hu not_active IP Right Cessation
- 1985-03-28 CA CA000477854A patent/CA1257253A/en not_active Expired
- 1985-03-28 DK DK140385A patent/DK140385A/da not_active Application Discontinuation
- 1985-03-28 KR KR1019850002139A patent/KR870000699B1/ko not_active Expired
- 1985-03-28 SU SU853878797A patent/SU1487824A3/ru active
- 1985-03-28 FI FI851248A patent/FI81359C/fi not_active IP Right Cessation
- 1985-03-29 JP JP60064003A patent/JPS60218397A/ja active Granted
-
1986
- 1986-06-17 DD DD86291381A patent/DD246120A5/de not_active IP Right Cessation
- 1986-06-24 SU SU864027681A patent/SU1574173A3/ru active
-
1989
- 1989-08-07 JP JP1202971A patent/JPH02160771A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| SU1574173A3 (ru) | 1990-06-23 |
| DE3411574A1 (de) | 1985-10-10 |
| DD246120A5 (de) | 1987-05-27 |
| FI851248A0 (fi) | 1985-03-28 |
| HU198734B (en) | 1989-11-28 |
| CS206485A2 (en) | 1990-07-12 |
| HUT38104A (en) | 1986-04-28 |
| ATE66929T1 (de) | 1991-09-15 |
| ES8603192A1 (es) | 1985-12-16 |
| DD235648A5 (de) | 1986-05-14 |
| AU550958B2 (en) | 1986-04-10 |
| ES541589A0 (es) | 1985-12-16 |
| DK140385D0 (da) | 1985-03-28 |
| FI81359C (fi) | 1990-10-10 |
| FI851248L (fi) | 1985-09-30 |
| ZA852333B (en) | 1985-12-24 |
| DE3583954D1 (de) | 1991-10-10 |
| KR850006427A (ko) | 1985-10-05 |
| FI81359B (fi) | 1990-06-29 |
| JPH027589B2 (enrdf_load_stackoverflow) | 1990-02-19 |
| EP0156347B1 (de) | 1991-09-04 |
| JPH0579064B2 (enrdf_load_stackoverflow) | 1993-11-01 |
| AU4037585A (en) | 1985-10-03 |
| EP0156347A2 (de) | 1985-10-02 |
| JPH02160771A (ja) | 1990-06-20 |
| DK140385A (da) | 1985-09-30 |
| KR870000699B1 (ko) | 1987-04-07 |
| SU1487824A3 (ru) | 1989-06-15 |
| CA1257253A (en) | 1989-07-11 |
| EP0156347A3 (en) | 1988-01-13 |
| JPS60218397A (ja) | 1985-11-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CS273162B2 (en) | Diagnostic agent for glicosidases activity determination | |
| EP0231125B1 (en) | Hydrolyzable fluorescent substrates and analytical determinations using same | |
| EP0270946B1 (en) | Chromogenic acridinone enzyme substrates | |
| US4668622A (en) | Phenolsulphonphthaleinyl-β-D-galactosides and diagnostic agents containing them | |
| US4952495A (en) | Hydrolyzable compounds which release electron transfer agents and analytical use of same | |
| US5292669A (en) | Agents for the detection of substrates with hydrolase activity | |
| US4754025A (en) | Glucosamine derivatives and reagent for assaying N-acetyl-β-D-glucosaminidase using the same as substrate | |
| EP2138483B1 (en) | Oxidative color-developing compounds, salts thereof, process for production of the same, reagent compositions and test tools made by using the same | |
| JP3994461B2 (ja) | ヒドロキシアルキルピリジン誘導体 | |
| KR890004092B1 (ko) | 과산화수소, 과산화염-작용화합물 및 과산화효소의 결정을 위한 방법 및 시약조성물 | |
| JPS58994A (ja) | 新規Ｎ−アセチル−β−Ｄ−グルコサミン誘導体およびこれを基質として用いるＮ−アセチル−β−Ｄ−グルコサミニダ−ゼ活性測定法 | |
| US5202233A (en) | Process for the detection of substances with hydrolase activity | |
| KR920000058B1 (ko) | 가수분해효소 활성을 갖는 물질들의 검출방법 및 약품 | |
| WO2000055167A1 (fr) | Derives de 2-pyridinethiol et reactifs permettant la mesure de l'activite de la nag contenant ceux-ci | |
| EP0459536A1 (en) | Chromogenic acridinone enzyme substrates | |
| US6534637B2 (en) | Synthesis of chlorophenol red glucuronic acid | |
| US5260428A (en) | Agent for the detection of substances with hydrolase activity | |
| JPS6339600A (ja) | α−アミラ−ゼアイソザイムの分別測定法 | |
| JPH0687798B2 (ja) | 体液中のカルシウム測定方法 | |
| JPS6317895A (ja) | 新規なオリゴサツカライド誘導体、及びこれを用いるα−アミラ−ゼ活性測定法 | |
| CS273184B2 (en) | Method of resorufin's derivative glycoside production | |
| CS268700B2 (en) | Means for beta-d-galacosidase determination | |
| JPH09249684A (ja) | アミラーゼ活性測定用新規化合物およびそれを用いたアミラーゼ活性の測定方法 | |
| JPH09289899A (ja) | α−アミラーゼ活性測定用基質、測定試薬及び測定方法 |