FI93278C - Diagnostinen analyysielementti ja fluoresoiva konjugaatti - Google Patents
Diagnostinen analyysielementti ja fluoresoiva konjugaatti Download PDFInfo
- Publication number
- FI93278C FI93278C FI884922A FI884922A FI93278C FI 93278 C FI93278 C FI 93278C FI 884922 A FI884922 A FI 884922A FI 884922 A FI884922 A FI 884922A FI 93278 C FI93278 C FI 93278C
- Authority
- FI
- Finland
- Prior art keywords
- biologically active
- substituent
- active moiety
- hydrophilic group
- element according
- Prior art date
Links
- 238000003556 assay Methods 0.000 title claims description 18
- 239000012491 analyte Substances 0.000 claims abstract description 8
- 239000013060 biological fluid Substances 0.000 claims abstract description 3
- 125000001424 substituent group Chemical group 0.000 claims description 29
- 239000003153 chemical reaction reagent Substances 0.000 claims description 17
- -1 phosphate ester Chemical class 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 10
- 239000000427 antigen Substances 0.000 claims description 7
- 102000036639 antigens Human genes 0.000 claims description 7
- 108091007433 antigens Proteins 0.000 claims description 7
- 108020003215 DNA Probes Proteins 0.000 claims description 5
- 239000003298 DNA probe Substances 0.000 claims description 5
- 229910019142 PO4 Inorganic materials 0.000 claims description 5
- 239000000523 sample Substances 0.000 claims description 5
- 102000001706 Immunoglobulin Fab Fragments Human genes 0.000 claims description 4
- 108010054477 Immunoglobulin Fab Fragments Proteins 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- 239000012530 fluid Substances 0.000 claims description 3
- 229920000570 polyether Polymers 0.000 claims description 3
- 150000005846 sugar alcohols Polymers 0.000 claims description 3
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims 4
- 239000004327 boric acid Substances 0.000 claims 4
- 239000010452 phosphate Substances 0.000 claims 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims 2
- 239000004721 Polyphenylene oxide Substances 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 2
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims 2
- 150000003008 phosphonic acid esters Chemical class 0.000 claims 2
- LOTBYPQQWICYBB-UHFFFAOYSA-N methyl n-hexyl-n-[2-(hexylamino)ethyl]carbamate Chemical compound CCCCCCNCCN(C(=O)OC)CCCCCC LOTBYPQQWICYBB-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 8
- 239000001022 rhodamine dye Substances 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 36
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 29
- 239000000203 mixture Substances 0.000 description 26
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
- 150000001875 compounds Chemical class 0.000 description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- 239000000741 silica gel Substances 0.000 description 16
- 229910002027 silica gel Inorganic materials 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- 239000010410 layer Substances 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
- 239000000975 dye Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical group O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 125000005647 linker group Chemical group 0.000 description 9
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 229910001873 dinitrogen Inorganic materials 0.000 description 7
- 239000003480 eluent Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 6
- 229960000278 theophylline Drugs 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 150000008064 anhydrides Chemical class 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 230000008878 coupling Effects 0.000 description 5
- 238000010168 coupling process Methods 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 239000007850 fluorescent dye Substances 0.000 description 5
- 230000003993 interaction Effects 0.000 description 5
- XUIIKFGFIJCVMT-GFCCVEGCSA-N D-thyroxine Chemical compound IC1=CC(C[C@@H](N)C(O)=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 XUIIKFGFIJCVMT-GFCCVEGCSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000007853 buffer solution Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 235000019439 ethyl acetate Nutrition 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 4
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- OWWAUBQOFLVUMS-UHFFFAOYSA-N 2,3-dihydro-1h-indol-4-ol Chemical compound OC1=CC=CC2=C1CCN2 OWWAUBQOFLVUMS-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 229910004373 HOAc Inorganic materials 0.000 description 3
- 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 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000003018 immunoassay Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 230000002441 reversible effect Effects 0.000 description 3
- 210000002966 serum Anatomy 0.000 description 3
- 230000003381 solubilizing effect Effects 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- 229960003080 taurine Drugs 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 229940034208 thyroxine Drugs 0.000 description 3
- XUIIKFGFIJCVMT-UHFFFAOYSA-N thyroxine-binding globulin Natural products IC1=CC(CC([NH3+])C([O-])=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 XUIIKFGFIJCVMT-UHFFFAOYSA-N 0.000 description 3
- AXDJCCTWPBKUKL-UHFFFAOYSA-N 4-[(4-aminophenyl)-(4-imino-3-methylcyclohexa-2,5-dien-1-ylidene)methyl]aniline;hydron;chloride Chemical compound Cl.C1=CC(=N)C(C)=CC1=C(C=1C=CC(N)=CC=1)C1=CC=C(N)C=C1 AXDJCCTWPBKUKL-UHFFFAOYSA-N 0.000 description 2
- FWEOQOXTVHGIFQ-UHFFFAOYSA-M 8-anilinonaphthalene-1-sulfonate Chemical compound C=12C(S(=O)(=O)[O-])=CC=CC2=CC=CC=1NC1=CC=CC=C1 FWEOQOXTVHGIFQ-UHFFFAOYSA-M 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 210000001124 body fluid Anatomy 0.000 description 2
- 239000010839 body fluid Substances 0.000 description 2
- 229940098773 bovine serum albumin Drugs 0.000 description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
- 239000012482 calibration solution Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 238000012875 competitive assay Methods 0.000 description 2
- ASMQGLCHMVWBQR-UHFFFAOYSA-M diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-M 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000005670 electromagnetic radiation Effects 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229940088597 hormone Drugs 0.000 description 2
- 239000005556 hormone Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 230000001900 immune effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 230000000269 nucleophilic effect Effects 0.000 description 2
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 1
- QORVGJAHBMMXFG-UHFFFAOYSA-N 2,2,6-triaminohexanoic acid Chemical compound NCCCCC(N)(N)C(O)=O QORVGJAHBMMXFG-UHFFFAOYSA-N 0.000 description 1
- 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 1
- SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 1
- NLMQHXUGJIAKTH-UHFFFAOYSA-N 4-hydroxyindole Chemical compound OC1=CC=CC2=C1C=CN2 NLMQHXUGJIAKTH-UHFFFAOYSA-N 0.000 description 1
- 108010017384 Blood Proteins Proteins 0.000 description 1
- 102000004506 Blood Proteins Human genes 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- 108020004635 Complementary DNA Proteins 0.000 description 1
- ASMQGLCHMVWBQR-UHFFFAOYSA-N Diphenyl phosphate Chemical class C=1C=CC=CC=1OP(=O)(O)OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 239000007995 HEPES buffer Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 102000008394 Immunoglobulin Fragments Human genes 0.000 description 1
- 108010021625 Immunoglobulin Fragments Proteins 0.000 description 1
- XUIIKFGFIJCVMT-LBPRGKRZSA-N L-thyroxine Chemical compound IC1=CC(C[C@H]([NH3+])C([O-])=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 XUIIKFGFIJCVMT-LBPRGKRZSA-N 0.000 description 1
- CXOFVDLJLONNDW-UHFFFAOYSA-N Phenytoin Chemical compound N1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 CXOFVDLJLONNDW-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- HAXFWIACAGNFHA-UHFFFAOYSA-N aldrithiol Chemical class C=1C=CC=NC=1SSC1=CC=CC=N1 HAXFWIACAGNFHA-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 235000010338 boric acid Nutrition 0.000 description 1
- 125000005619 boric acid group Chemical class 0.000 description 1
- 125000005620 boronic acid group Chemical class 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 238000010804 cDNA synthesis Methods 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 150000001805 chlorine compounds Chemical group 0.000 description 1
- 238000002967 competitive immunoassay Methods 0.000 description 1
- 239000002299 complementary DNA Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000002405 diagnostic procedure Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000002532 enzyme inhibitor Substances 0.000 description 1
- 229940125532 enzyme inhibitor Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000004687 hexahydrates Chemical class 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- NTYJJOPFIAHURM-UHFFFAOYSA-N histamine Natural products NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 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
- 230000028993 immune response Effects 0.000 description 1
- 238000013198 immunometric assay Methods 0.000 description 1
- 239000012678 infectious agent Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 229950008325 levothyroxine Drugs 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 229960002695 phenobarbital Drugs 0.000 description 1
- 229960002036 phenytoin Drugs 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 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
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- GINSRDSEEGBTJO-UHFFFAOYSA-N thietane 1-oxide Chemical compound O=S1CCC1 GINSRDSEEGBTJO-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
- G01N33/531—Production of immunochemical test materials
- G01N33/532—Production of labelled immunochemicals
- G01N33/533—Production of labelled immunochemicals with fluorescent label
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/10—Amino derivatives of triarylmethanes
- C09B11/24—Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/805—Test papers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/81—Packaged device or kit
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S436/00—Chemistry: analytical and immunological testing
- Y10S436/80—Fluorescent dyes, e.g. rhodamine
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S436/00—Chemistry: analytical and immunological testing
- Y10S436/805—Optical property
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S436/00—Chemistry: analytical and immunological testing
- Y10S436/807—Apparatus included in process claim, e.g. physical support structures
- Y10S436/808—Automated or kit
Landscapes
- Health & Medical Sciences (AREA)
- Immunology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Molecular Biology (AREA)
- Biomedical Technology (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Cell Biology (AREA)
- Food Science & Technology (AREA)
- Medicinal Chemistry (AREA)
- Biotechnology (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Microbiology (AREA)
- Pathology (AREA)
- Organic Chemistry (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Peptides Or Proteins (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Luminescent Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3422587 | 1987-04-02 | ||
| US07/034,225 US4900686A (en) | 1987-04-02 | 1987-04-02 | Fluorescent conjugates and biological diagnostic assay |
| US8800641 | 1988-02-23 | ||
| PCT/US1988/000641 WO1988007682A1 (en) | 1987-04-02 | 1988-02-23 | Fluorescent conjugates and biological diagnostic assay |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI884922L FI884922L (fi) | 1988-10-25 |
| FI884922A0 FI884922A0 (fi) | 1988-10-25 |
| FI93278B FI93278B (fi) | 1994-11-30 |
| FI93278C true FI93278C (fi) | 1995-03-10 |
Family
ID=21875075
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI884922A FI93278C (fi) | 1987-04-02 | 1988-10-25 | Diagnostinen analyysielementti ja fluoresoiva konjugaatti |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4900686A (enExample) |
| EP (1) | EP0285179B1 (enExample) |
| JP (1) | JPH0718874B2 (enExample) |
| AT (1) | ATE90789T1 (enExample) |
| AU (1) | AU602090B2 (enExample) |
| CA (1) | CA1339782C (enExample) |
| DE (1) | DE3881735T2 (enExample) |
| ES (1) | ES2058164T3 (enExample) |
| FI (1) | FI93278C (enExample) |
| GR (1) | GR3008515T3 (enExample) |
| NZ (1) | NZ223998A (enExample) |
| WO (1) | WO1988007682A1 (enExample) |
| ZA (1) | ZA881640B (enExample) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2681061B2 (ja) * | 1988-06-08 | 1997-11-19 | ロンドン・ダイアグノスティック・インコーポレーテッド | 検出可能なシグナルのセンシタイザー誘導発生を利用したアッセイ |
| US5364796A (en) * | 1989-07-11 | 1994-11-15 | Pb Diagnostics Systems, Inc. | Diagnostic assay system |
| US5290682A (en) * | 1991-05-31 | 1994-03-01 | Polaroid Corporation | Enzyme controlled processes and products |
| US5750409A (en) * | 1991-11-18 | 1998-05-12 | Boehringer Mannheim Gmbh | Pentacyclic compounds and their use as absorption or fluorescent dyes |
| DE4137934A1 (de) * | 1991-11-18 | 1993-05-19 | Boehringer Mannheim Gmbh | Neue pentacyklische verbindungen und ihre verwendung als absorptions- oder fluoreszenzfarbstoffe |
| EP0573762A2 (de) * | 1992-05-11 | 1993-12-15 | BASF Aktiengesellschaft | Rhodaminderivate |
| CA2158782C (en) * | 1994-09-23 | 2010-01-12 | Pierrette Gaudreau | Marker for growth hormone-releasing factor receptors |
| CA2164167A1 (en) * | 1994-12-20 | 1996-06-21 | Izak Bahar | Assay normalization method |
| US6008373A (en) | 1995-06-07 | 1999-12-28 | Carnegie Mellon University | Fluorescent labeling complexes with large stokes shift formed by coupling together cyanine and other fluorochromes capable of resonance energy transfer |
| US5650512A (en) * | 1995-06-07 | 1997-07-22 | Systemix | Fluorescent labeling reagents |
| FR2742047B1 (fr) * | 1995-12-06 | 1998-01-16 | Oreal | Compositions de teinture des fibres keratiniques contenant des derives n-substitues de la 4-hydroxy indoline, nouveaux derives, leur procede de synthese, leur utilisation pour la teinture, et procede de teinture |
| US5847162A (en) * | 1996-06-27 | 1998-12-08 | The Perkin Elmer Corporation | 4, 7-Dichlororhodamine dyes |
| US6017712A (en) * | 1996-06-27 | 2000-01-25 | Lee; Linda | 4,7-dichlororhodamine dyes |
| US5795784A (en) | 1996-09-19 | 1998-08-18 | Abbott Laboratories | Method of performing a process for determining an item of interest in a sample |
| US5856194A (en) | 1996-09-19 | 1999-01-05 | Abbott Laboratories | Method for determination of item of interest in a sample |
| US6130101A (en) * | 1997-09-23 | 2000-10-10 | Molecular Probes, Inc. | Sulfonated xanthene derivatives |
| US6342611B1 (en) | 1997-10-10 | 2002-01-29 | Cytovia, Inc. | Fluorogenic or fluorescent reporter molecules and their applications for whole-cell fluorescence screening assays for capsases and other enzymes and the use thereof |
| DE19824535A1 (de) | 1998-06-03 | 1999-12-09 | Roche Diagnostics Gmbh | Neue Rhodamin-Derivate und deren Verwendung |
| EP1100520B1 (en) | 1998-07-21 | 2004-09-22 | Cytovia, Inc. | Novel fluorescence dyes and their applications for whole cell fluorescence screening assays for caspases, peptidases, proteases and other enzymes and the use thereof |
| US6750357B1 (en) * | 1999-06-25 | 2004-06-15 | Syngen, Inc. | Rhodamine-based fluorophores useful as labeling reagents |
| WO2002012545A2 (en) | 2000-08-03 | 2002-02-14 | Cytovia, Inc. | Method of identifying immunosuppressive agents |
| US11008359B2 (en) | 2002-08-23 | 2021-05-18 | Illumina Cambridge Limited | Labelled nucleotides |
| US7344701B2 (en) | 2004-02-03 | 2008-03-18 | Biosearch Technologies, Inc. | Xanthene dyes |
| EP2021415B1 (en) | 2006-05-18 | 2017-03-15 | Illumina Cambridge Limited | Dye compounds and the use of their labelled conjugates |
| WO2013078244A1 (en) | 2011-11-21 | 2013-05-30 | Promega Corporation | Carboxy x rhodamine analogs |
| US9499484B2 (en) | 2012-04-02 | 2016-11-22 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd | Indole, indoline derivatives, compositions comprising them and uses thereof |
| ES2685549T3 (es) | 2013-03-15 | 2018-10-09 | Illumina Cambridge Limited | Nucleósidos o nucleótidos modificados |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3822270A (en) * | 1971-08-09 | 1974-07-02 | Eastman Kodak Co | Pyrylium dyes having a fused,rigidized nitrogen-containing ring |
| US3932415A (en) * | 1972-04-17 | 1976-01-13 | Eastman Kodak Company | Pyrylium dyes having a fused rigidized nitrogen-containing ring |
| US4005092A (en) * | 1973-08-20 | 1977-01-25 | Eastman Kodak Company | Pyrylium dyes having a fused, rigidized nitrogen-containing ring |
| US4351760A (en) * | 1979-09-07 | 1982-09-28 | Syva Company | Novel alkyl substituted fluorescent compounds and polyamino acid conjugates |
| US4588697A (en) * | 1979-09-07 | 1986-05-13 | Syntex (U.S.A.) Inc. | Method for performing fluorescent protein binding assay employing novel alkyl substituted fluorescent compounds and conjugates |
| US4481136A (en) * | 1979-09-07 | 1984-11-06 | Syva Company | Alkyl substituted fluorescent compounds and conjugates |
| EP0050684B1 (en) * | 1980-10-27 | 1986-01-22 | Syva Company | Novel ether substituted fluorescein compounds as fluorescers and quenchers |
| IT1140209B (it) * | 1981-09-25 | 1986-09-24 | Anic Spa | Reagenti per immunoluorescenza e metodo per la loro preparazione |
| US4622400A (en) * | 1983-12-29 | 1986-11-11 | The United States Of America As Represented By The United States Department Of Energy | Preparation of certain m-aminophenols and the use thereof for preparation of laser dyes |
-
1987
- 1987-04-02 US US07/034,225 patent/US4900686A/en not_active Expired - Lifetime
-
1988
- 1988-02-23 WO PCT/US1988/000641 patent/WO1988007682A1/en not_active Ceased
- 1988-02-23 AU AU17281/88A patent/AU602090B2/en not_active Ceased
- 1988-02-23 JP JP63504346A patent/JPH0718874B2/ja not_active Expired - Lifetime
- 1988-03-08 ZA ZA881640A patent/ZA881640B/xx unknown
- 1988-03-14 CA CA000561395A patent/CA1339782C/en not_active Expired - Fee Related
- 1988-03-24 NZ NZ223998A patent/NZ223998A/xx unknown
- 1988-04-01 ES ES88105319T patent/ES2058164T3/es not_active Expired - Lifetime
- 1988-04-01 DE DE88105319T patent/DE3881735T2/de not_active Expired - Fee Related
- 1988-04-01 AT AT88105319T patent/ATE90789T1/de not_active IP Right Cessation
- 1988-04-01 EP EP88105319A patent/EP0285179B1/en not_active Expired - Lifetime
- 1988-10-25 FI FI884922A patent/FI93278C/fi not_active IP Right Cessation
-
1993
- 1993-07-16 GR GR920403057T patent/GR3008515T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GR3008515T3 (enExample) | 1993-10-29 |
| ZA881640B (en) | 1989-01-25 |
| JPH0718874B2 (ja) | 1995-03-06 |
| AU602090B2 (en) | 1990-09-27 |
| FI884922L (fi) | 1988-10-25 |
| NZ223998A (en) | 1989-11-28 |
| ES2058164T3 (es) | 1994-11-01 |
| DE3881735T2 (de) | 1993-10-07 |
| DE3881735D1 (de) | 1993-07-22 |
| EP0285179A2 (en) | 1988-10-05 |
| US4900686A (en) | 1990-02-13 |
| FI884922A0 (fi) | 1988-10-25 |
| CA1339782C (en) | 1998-03-31 |
| FI93278B (fi) | 1994-11-30 |
| AU1728188A (en) | 1988-11-02 |
| WO1988007682A1 (en) | 1988-10-06 |
| EP0285179A3 (en) | 1988-11-23 |
| JPH01503488A (ja) | 1989-11-22 |
| ATE90789T1 (de) | 1993-07-15 |
| EP0285179B1 (en) | 1993-06-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FI93278B (fi) | Diagnostinen analyysielementti ja fluoresoiva konjugaatti | |
| EP0273115B1 (en) | Chemiluminescent acridinium and phenanthridinium salts | |
| EP0203047B1 (en) | Fluorescent lanthanide chelates | |
| US4886744A (en) | Fluorescent conjugates and biological diagnostic assay system | |
| EP0108399B1 (en) | Substituted carboxyfluoresceins | |
| JP4195200B2 (ja) | ポルフィリン化合物、それらの結合体および前記結合体の使用に基づく検定方法 | |
| EP0988551B1 (en) | Chemiluminescent energy transfer conjugates and their uses as labels in binding assays | |
| CS273617B2 (en) | Method of resorufine's derivatives production | |
| US6277984B1 (en) | Monomethine cyanines rigidized by a two-carbon chain | |
| JP3172522B2 (ja) | 改良された化学ルミネセントエステル，チオエステルおよびアミドを用いるアッセイ法 | |
| JP2002529466A5 (enExample) | ||
| GB2111476A (en) | Substituted carboxy- fluoresceins and their use in fluorescence polarization immunoassay | |
| WO2004027388A2 (en) | Novel green and orange fluorescent labels and their uses | |
| US20040063147A1 (en) | Novel applications of acridinium compounds and derivatives in homogeneous assays | |
| CA1178269A (en) | Fluorescent polarization immunoassay utilizing substituted carboxyfluoresceins | |
| US20090136931A1 (en) | Novel fluorescent labeling compound | |
| KR19990014715A (ko) | 에스에이치기 표지용 시약, 그의 제조방법 및 이를 이용한 표지법 | |
| US5879953A (en) | Special chemiluminescent acridine derivatives and the use thereof in luminescence immunoassays | |
| ES2327141T3 (es) | Compuestos luminiscentes dotados de un brazo de enlace funcionalizado utilizado en bioconjugacion y marcado de biomoleculas. | |
| JP3248628B2 (ja) | 化学発光性化合物およびこれを用いるアッセイ法 | |
| JP3325370B2 (ja) | 化学発光性化合物およびこれを用いるアッセイ法 | |
| JPS62502548A (ja) | 新規な螢光性化合物および生物学的検査装置 | |
| RU1833690C (ru) | Способ определения антигенов или антител | |
| JPH04244085A (ja) | 蛍光性化合物、錯体、試薬および該試薬を用いる特異的結合アッセイ |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BB | Publication of examined application | ||
| PC | Transfer of assignment of patent |
Owner name: DADE BEHRING MARBURG GMBH |
|
| MM | Patent lapsed |
Owner name: DADE BEHRING MARBURG GMBH |