FI112543B - Kemiluminoiva reagenssi ja analyysimenetelmä, joissa käytetään substituoitua asetanilidia valon muodostukseen - Google Patents
Kemiluminoiva reagenssi ja analyysimenetelmä, joissa käytetään substituoitua asetanilidia valon muodostukseen Download PDFInfo
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- FI112543B FI112543B FI954029A FI954029A FI112543B FI 112543 B FI112543 B FI 112543B FI 954029 A FI954029 A FI 954029A FI 954029 A FI954029 A FI 954029A FI 112543 B FI112543 B FI 112543B
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- peroxidase
- carbon atoms
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- hydrogen atom
- specific binding
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- 150000008061 acetanilides Chemical class 0.000 title claims abstract description 16
- 229960001413 acetanilide Drugs 0.000 title claims abstract description 11
- FZERHIULMFGESH-UHFFFAOYSA-N methylenecarboxanilide Natural products CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 239000003153 chemical reaction reagent Substances 0.000 title claims description 33
- 238000003556 assay Methods 0.000 title abstract description 32
- 239000000203 mixture Substances 0.000 claims abstract description 99
- 102000003992 Peroxidases Human genes 0.000 claims abstract description 80
- 108040007629 peroxidase activity proteins Proteins 0.000 claims abstract description 79
- 125000004432 carbon atom Chemical group C* 0.000 claims description 53
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical group OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 40
- 230000009870 specific binding Effects 0.000 claims description 37
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 36
- 239000003446 ligand Substances 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 239000000126 substance Substances 0.000 claims description 18
- 239000000872 buffer Substances 0.000 claims description 16
- 239000000463 material Substances 0.000 claims description 16
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 14
- 238000001514 detection method Methods 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 12
- 239000003093 cationic surfactant Substances 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 229920006317 cationic polymer Polymers 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 238000012360 testing method Methods 0.000 claims description 10
- 239000007800 oxidant agent Substances 0.000 claims description 9
- 238000000159 protein binding assay Methods 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000000693 micelle Substances 0.000 claims description 8
- JULKJDRBSRRBHT-UHFFFAOYSA-N n-(3-chloro-4-hydroxyphenyl)acetamide Chemical group CC(=O)NC1=CC=C(O)C(Cl)=C1 JULKJDRBSRRBHT-UHFFFAOYSA-N 0.000 claims description 8
- 230000001590 oxidative effect Effects 0.000 claims description 8
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims description 7
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical group [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 claims description 7
- WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 claims description 6
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
- 150000007523 nucleic acids Chemical class 0.000 claims description 6
- 108020004707 nucleic acids Proteins 0.000 claims description 6
- 102000039446 nucleic acids Human genes 0.000 claims description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 5
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 5
- 239000002250 absorbent Substances 0.000 claims description 4
- 230000002745 absorbent Effects 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 238000002405 diagnostic procedure Methods 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 230000004044 response Effects 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 238000009739 binding Methods 0.000 claims description 3
- 239000012876 carrier material Substances 0.000 claims description 3
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 3
- 108091034117 Oligonucleotide Proteins 0.000 claims description 2
- JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 claims description 2
- 238000004806 packaging method and process Methods 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 239000000427 antigen Substances 0.000 claims 2
- 102000036639 antigens Human genes 0.000 claims 2
- 108091007433 antigens Proteins 0.000 claims 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- 230000027455 binding Effects 0.000 claims 1
- 239000012928 buffer substance Substances 0.000 claims 1
- 230000000295 complement effect Effects 0.000 claims 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 239000000758 substrate Substances 0.000 abstract description 8
- 230000007935 neutral effect Effects 0.000 abstract description 6
- -1 p-iodophenol Chemical class 0.000 description 35
- 239000012491 analyte Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- 230000035945 sensitivity Effects 0.000 description 13
- 108010001336 Horseradish Peroxidase Proteins 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 125000002091 cationic group Chemical group 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 238000002156 mixing Methods 0.000 description 10
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- 102000011923 Thyrotropin Human genes 0.000 description 9
- 108010061174 Thyrotropin Proteins 0.000 description 9
- HWYHZTIRURJOHG-UHFFFAOYSA-N luminol Chemical compound O=C1NNC(=O)C2=C1C(N)=CC=C2 HWYHZTIRURJOHG-UHFFFAOYSA-N 0.000 description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 description 8
- 229960003330 pentetic acid Drugs 0.000 description 8
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 7
- 102000004190 Enzymes Human genes 0.000 description 7
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- 239000000306 component Substances 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- 150000002978 peroxides Chemical class 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 5
- 150000003931 anilides Chemical class 0.000 description 5
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- 239000005081 chemiluminescent agent Substances 0.000 description 5
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- 238000007254 oxidation reaction Methods 0.000 description 5
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- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
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- 239000007983 Tris buffer Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 235000019270 ammonium chloride Nutrition 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
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- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 4
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- 229920002554 vinyl polymer Polymers 0.000 description 4
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 3
- PJFNNMFXEVADGK-UHFFFAOYSA-N 2-hydroxy-n-phenylacetamide Chemical compound OCC(=O)NC1=CC=CC=C1 PJFNNMFXEVADGK-UHFFFAOYSA-N 0.000 description 3
- VSMDINRNYYEDRN-UHFFFAOYSA-N 4-iodophenol Chemical compound OC1=CC=C(I)C=C1 VSMDINRNYYEDRN-UHFFFAOYSA-N 0.000 description 3
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- 238000004458 analytical method Methods 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
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- 125000001246 bromo group Chemical group Br* 0.000 description 3
- 230000002255 enzymatic effect Effects 0.000 description 3
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 3
- 230000002538 fungal effect Effects 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 125000001453 quaternary ammonium group Chemical group 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
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- 125000005023 xylyl group Chemical group 0.000 description 3
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- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
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- 241001465754 Metazoa Species 0.000 description 2
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- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
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- 229960001927 cetylpyridinium chloride Drugs 0.000 description 2
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- 125000000913 palmityl 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])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 2
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- 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 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 238000007899 nucleic acid hybridization Methods 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229960005489 paracetamol Drugs 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 238000003752 polymerase chain reaction Methods 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 238000004451 qualitative analysis Methods 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 239000000700 radioactive tracer Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 230000003335 steric effect Effects 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- NBNBICNWNFQDDD-UHFFFAOYSA-N sulfuryl dibromide Chemical compound BrS(Br)(=O)=O NBNBICNWNFQDDD-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
- GLFDLEXFOHUASB-UHFFFAOYSA-N trimethyl(tetradecyl)azanium Chemical compound CCCCCCCCCCCCCC[N+](C)(C)C GLFDLEXFOHUASB-UHFFFAOYSA-N 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- ORHBXUUXSCNDEV-UHFFFAOYSA-N umbelliferone Chemical compound C1=CC(=O)OC2=CC(O)=CC=C21 ORHBXUUXSCNDEV-UHFFFAOYSA-N 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 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
- G01N33/58—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances
- G01N33/582—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances with fluorescent label
-
- 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
- C12Q1/26—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving oxidoreductase
- C12Q1/28—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving oxidoreductase involving peroxidase
-
- 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
- C12Q1/66—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving luciferase
-
- 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
- G01N33/535—Production of labelled immunochemicals with enzyme label or co-enzymes, co-factors, enzyme inhibitors or enzyme substrates
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Zoology (AREA)
- General Health & Medical Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Microbiology (AREA)
- Urology & Nephrology (AREA)
- Analytical Chemistry (AREA)
- Wood Science & Technology (AREA)
- Physics & Mathematics (AREA)
- Biochemistry (AREA)
- Hematology (AREA)
- Biomedical Technology (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- General Engineering & Computer Science (AREA)
- Cell Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biophysics (AREA)
- Food Science & Technology (AREA)
- Medicinal Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Luminescent Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29747594 | 1994-08-29 | ||
| US08/297,475 US5705357A (en) | 1994-08-29 | 1994-08-29 | Chemiluminescent reagent and assay using a substituted acetanilide for light generation |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI954029A0 FI954029A0 (fi) | 1995-08-28 |
| FI954029L FI954029L (fi) | 1996-03-01 |
| FI112543B true FI112543B (fi) | 2003-12-15 |
Family
ID=23146476
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI954029A FI112543B (fi) | 1994-08-29 | 1995-08-28 | Kemiluminoiva reagenssi ja analyysimenetelmä, joissa käytetään substituoitua asetanilidia valon muodostukseen |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US5705357A (OSRAM) |
| EP (1) | EP0704539B1 (OSRAM) |
| JP (1) | JP3532669B2 (OSRAM) |
| KR (1) | KR100377038B1 (OSRAM) |
| AT (1) | ATE199399T1 (OSRAM) |
| AU (1) | AU700528B2 (OSRAM) |
| CA (1) | CA2157062C (OSRAM) |
| DE (1) | DE69520183T2 (OSRAM) |
| FI (1) | FI112543B (OSRAM) |
| NO (1) | NO316228B1 (OSRAM) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001249079A (ja) * | 1999-12-28 | 2001-09-14 | Fujirebio Inc | 発光量調節剤を用いた化学発光測定方法及び酵素免疫測定方法 |
| EP1254252A4 (en) * | 2000-01-28 | 2006-06-07 | Brij P Giri | NEW STABILIZED FORMULATIONS FOR CHEMILUMINESCENCE ASSAYS |
| US6485923B1 (en) * | 2000-02-02 | 2002-11-26 | Lifescan, Inc. | Reagent test strip for analyte determination having hemolyzing agent |
| US7368296B2 (en) * | 2002-01-17 | 2008-05-06 | Applied Biosystems | Solid phases optimized for chemiluminescent detection |
| CN101340887B (zh) | 2005-11-09 | 2014-01-29 | 科洛斯科技公司 | 使牙齿增白的组合物及方法 |
| US20100266989A1 (en) | 2006-11-09 | 2010-10-21 | Klox Technologies Inc. | Teeth whitening compositions and methods |
| EA029534B1 (ru) | 2008-11-07 | 2018-04-30 | Клокс Текнолоджиз Инк. | Комбинация оксиданта и фотоактиватора для заживления ран |
| DK2453922T3 (en) | 2009-07-17 | 2018-01-02 | Klox Tech Inc | ANTIBACTERIAL ORAL COMPOSITION |
| KR20140027383A (ko) * | 2011-06-17 | 2014-03-06 | 교와 메덱스 가부시키가이샤 | 당화 헤모글로빈의 측정 방법, 측정 시약, 및 측정 키트 |
| US20130281913A1 (en) | 2012-04-20 | 2013-10-24 | Klox Technologies Inc. | Biophotonic compositions and methods for providing biophotonic treatment |
| US11116841B2 (en) | 2012-04-20 | 2021-09-14 | Klox Technologies Inc. | Biophotonic compositions, kits and methods |
| MX351267B (es) | 2012-09-14 | 2017-10-06 | Valeant Pharmaceuticals Int Inc | Composiciones y metodos para blanqueamiento dental. |
| US20140276354A1 (en) | 2013-03-14 | 2014-09-18 | Klox Technologies Inc. | Biophotonic materials and uses thereof |
| KR20210108505A (ko) | 2013-07-03 | 2021-09-02 | 광동 클록스 바이오메디컬 그룹 씨오., 엘티디 | 상처를 치료하기 위한 발색단과 겔화제를 포함하는 생체광자성 조성물 |
| WO2015149177A1 (en) | 2014-04-01 | 2015-10-08 | Klox Technologies Inc. | Tissue filler compositions and methods of use |
| EP3212826B1 (en) | 2014-10-31 | 2020-10-14 | Klox Technologies Inc. | Photoactivatable fibers and fabric media |
| WO2018164940A1 (en) * | 2017-03-07 | 2018-09-13 | Ortho-Clinical Diagnostics, Inc. | Methods for detecting analytes |
| WO2024162071A1 (ja) * | 2023-01-31 | 2024-08-08 | 株式会社トクヤマ | 組成物、重合性組成物、イオン交換樹脂、イオン交換膜、膜電極接合体、水素製造装置、及びイオン交換膜の製造方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0116454B1 (en) * | 1983-02-11 | 1987-04-29 | National Research Development Corporation | Enhanced luminescent or luminometric assay |
| GB8420053D0 (en) * | 1984-08-07 | 1984-09-12 | Secr Social Service Brit | Enhanced luminescent/luminometric assay |
| US4828983A (en) * | 1986-07-10 | 1989-05-09 | Eastman Kodak Company | Use of phenols and anilines to increase the rate of peroxidase catalyzed oxidation of leuco dyes |
| DE69114352T2 (de) * | 1990-04-30 | 1996-04-18 | Hitachi Chemical Co Ltd | Verbesserte chemilumineszierende Reagenzien und Verfahren. |
| US5279940A (en) * | 1992-08-03 | 1994-01-18 | Eastman Kodak Company | Chemiluminescent composition containing cationic surfactants or polymers and 4'-hydroxyacetanilide, test kits and their use in analytical methods |
| US5372931A (en) * | 1992-12-22 | 1994-12-13 | Eastman Kodak Company | Use of 4'-hydroxy- and 4'-alkoxy-substituted electron transfer agents in compositions, elements, test kits and analytical methods |
| US5372932A (en) * | 1992-12-22 | 1994-12-13 | Eastman Kodak Company | Analytical element and method for the determination of a specific binding ligand using a 4-hydroxy or 4-alkoxyarylacetamide as stabilizer |
-
1994
- 1994-08-29 US US08/297,475 patent/US5705357A/en not_active Expired - Lifetime
-
1995
- 1995-08-25 JP JP21783195A patent/JP3532669B2/ja not_active Expired - Fee Related
- 1995-08-28 NO NO19953368A patent/NO316228B1/no not_active IP Right Cessation
- 1995-08-28 CA CA002157062A patent/CA2157062C/en not_active Expired - Lifetime
- 1995-08-28 FI FI954029A patent/FI112543B/fi not_active IP Right Cessation
- 1995-08-28 AU AU30301/95A patent/AU700528B2/en not_active Expired
- 1995-08-29 DE DE69520183T patent/DE69520183T2/de not_active Expired - Lifetime
- 1995-08-29 KR KR1019950027049A patent/KR100377038B1/ko not_active Expired - Fee Related
- 1995-08-29 AT AT95306012T patent/ATE199399T1/de active
- 1995-08-29 EP EP95306012A patent/EP0704539B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| KR100377038B1 (ko) | 2003-12-31 |
| JP3532669B2 (ja) | 2004-05-31 |
| KR960007788A (ko) | 1996-03-22 |
| JPH08173191A (ja) | 1996-07-09 |
| DE69520183T2 (de) | 2001-08-02 |
| AU700528B2 (en) | 1999-01-07 |
| AU3030195A (en) | 1996-03-14 |
| FI954029L (fi) | 1996-03-01 |
| NO953368L (no) | 1996-03-01 |
| EP0704539A2 (en) | 1996-04-03 |
| NO316228B1 (no) | 2003-12-29 |
| EP0704539B1 (en) | 2001-02-28 |
| CA2157062A1 (en) | 1996-03-01 |
| NO953368D0 (no) | 1995-08-28 |
| FI954029A0 (fi) | 1995-08-28 |
| ATE199399T1 (de) | 2001-03-15 |
| CA2157062C (en) | 2009-12-01 |
| DE69520183D1 (de) | 2001-04-05 |
| EP0704539A3 (OSRAM) | 1996-04-10 |
| US5705357A (en) | 1998-01-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MA | Patent expired |