AU782559B2 - Acridinium ester labels having hydrophilic modifiers - Google Patents
Acridinium ester labels having hydrophilic modifiers Download PDFInfo
- Publication number
- AU782559B2 AU782559B2 AU45736/02A AU4573602A AU782559B2 AU 782559 B2 AU782559 B2 AU 782559B2 AU 45736/02 A AU45736/02 A AU 45736/02A AU 4573602 A AU4573602 A AU 4573602A AU 782559 B2 AU782559 B2 AU 782559B2
- Authority
- AU
- Australia
- Prior art keywords
- conjugate
- group
- acridinium ester
- acridinium
- ester
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
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- RXNXLAHQOVLMIE-UHFFFAOYSA-N phenyl 10-methylacridin-10-ium-9-carboxylate Chemical compound C12=CC=CC=C2[N+](C)=C2C=CC=CC2=C1C(=O)OC1=CC=CC=C1 RXNXLAHQOVLMIE-UHFFFAOYSA-N 0.000 title claims description 40
- 239000003607 modifier Substances 0.000 title claims description 22
- 238000003556 assay Methods 0.000 claims description 73
- 229960000278 theophylline Drugs 0.000 claims description 60
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 claims description 55
- 229960000707 tobramycin Drugs 0.000 claims description 55
- 239000012491 analyte Substances 0.000 claims description 52
- 238000006243 chemical reaction Methods 0.000 claims description 52
- 230000027455 binding Effects 0.000 claims description 41
- NLVFBUXFDBBNBW-PBSUHMDJSA-N tobramycin Chemical compound N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N NLVFBUXFDBBNBW-PBSUHMDJSA-N 0.000 claims description 41
- -1 acridinium compound Chemical class 0.000 claims description 34
- 150000002148 esters Chemical class 0.000 claims description 34
- 229920001223 polyethylene glycol Polymers 0.000 claims description 31
- 125000006850 spacer group Chemical group 0.000 claims description 31
- PFNFFQXMRSDOHW-UHFFFAOYSA-N spermine Chemical class NCCCNCCCCNCCCN PFNFFQXMRSDOHW-UHFFFAOYSA-N 0.000 claims description 29
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 125000000304 alkynyl group Chemical group 0.000 claims description 22
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 22
- 125000005842 heteroatom Chemical group 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 20
- 229910052717 sulfur Chemical group 0.000 claims description 18
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 17
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 17
- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 229910052698 phosphorus Inorganic materials 0.000 claims description 17
- 239000011574 phosphorus Chemical group 0.000 claims description 17
- 239000011593 sulfur Chemical group 0.000 claims description 17
- 239000002202 Polyethylene glycol Substances 0.000 claims description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 239000001301 oxygen Chemical group 0.000 claims description 15
- DZBUGLKDJFMEHC-UHFFFAOYSA-O acridine;hydron Chemical compound C1=CC=CC2=CC3=CC=CC=C3[NH+]=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-O 0.000 claims description 14
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 14
- 229920000831 ionic polymer Polymers 0.000 claims description 11
- 230000008569 process Effects 0.000 claims description 9
- 238000012875 competitive assay Methods 0.000 claims description 7
- 230000003993 interaction Effects 0.000 claims description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
- 229920000768 polyamine Polymers 0.000 claims description 7
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 229940126585 therapeutic drug Drugs 0.000 claims description 6
- 150000003568 thioethers Chemical class 0.000 claims description 6
- JOAQINSXLLMRCV-UHFFFAOYSA-N 4-{[(2-amino-4-hydroxypteridin-6-yl)methyl]amino}benzoic acid Chemical group C1=NC2=NC(N)=NC(O)=C2N=C1CNC1=CC=C(C(O)=O)C=C1 JOAQINSXLLMRCV-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 239000012039 electrophile Substances 0.000 claims description 5
- 150000004820 halides Chemical class 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 239000012038 nucleophile Substances 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 150000003384 small molecules Chemical class 0.000 claims description 5
- 229940088594 vitamin Drugs 0.000 claims description 5
- 235000013343 vitamin Nutrition 0.000 claims description 5
- 239000011782 vitamin Substances 0.000 claims description 5
- 229930003231 vitamin Natural products 0.000 claims description 5
- 102000014914 Carrier Proteins Human genes 0.000 claims description 4
- 108091008324 binding proteins Proteins 0.000 claims description 4
- 230000001268 conjugating effect Effects 0.000 claims description 4
- IIRDTKBZINWQAW-UHFFFAOYSA-N hexaethylene glycol Chemical group OCCOCCOCCOCCOCCOCCO IIRDTKBZINWQAW-UHFFFAOYSA-N 0.000 claims description 4
- 150000002433 hydrophilic molecules Chemical class 0.000 claims description 4
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 4
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 4
- 150000003431 steroids Chemical class 0.000 claims description 4
- 108090001008 Avidin Proteins 0.000 claims description 3
- 102000008394 Immunoglobulin Fragments Human genes 0.000 claims description 3
- 108010021625 Immunoglobulin Fragments Proteins 0.000 claims description 3
- 108010090804 Streptavidin Proteins 0.000 claims description 3
- 241000700605 Viruses Species 0.000 claims description 3
- 239000013566 allergen Substances 0.000 claims description 3
- 239000005556 hormone Substances 0.000 claims description 3
- 229940088597 hormone Drugs 0.000 claims description 3
- 229920002521 macromolecule Polymers 0.000 claims description 3
- 108010087904 neutravidin Proteins 0.000 claims description 3
- 108020004707 nucleic acids Proteins 0.000 claims description 3
- 102000039446 nucleic acids Human genes 0.000 claims description 3
- 150000007523 nucleic acids Chemical class 0.000 claims description 3
- 108020003175 receptors Proteins 0.000 claims description 3
- 229920001059 synthetic polymer Polymers 0.000 claims description 3
- 230000000977 initiatory effect Effects 0.000 claims description 2
- 102000004169 proteins and genes Human genes 0.000 claims description 2
- 108090000623 proteins and genes Proteins 0.000 claims description 2
- 102000005962 receptors Human genes 0.000 claims description 2
- 229910006069 SO3H Inorganic materials 0.000 claims 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 1
- 239000011724 folic acid Substances 0.000 description 71
- 229940014144 folate Drugs 0.000 description 64
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 description 58
- 235000019152 folic acid Nutrition 0.000 description 52
- 239000000700 radioactive tracer Substances 0.000 description 48
- 239000000047 product Substances 0.000 description 43
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- 238000004128 high performance liquid chromatography Methods 0.000 description 34
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 28
- 230000035945 sensitivity Effects 0.000 description 28
- 230000015572 biosynthetic process Effects 0.000 description 26
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 26
- 230000009871 nonspecific binding Effects 0.000 description 26
- 238000003786 synthesis reaction Methods 0.000 description 26
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 23
- 239000000243 solution Substances 0.000 description 23
- 239000007787 solid Substances 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 18
- 231100000673 dose–response relationship Toxicity 0.000 description 17
- 238000003018 immunoassay Methods 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 14
- 229940063675 spermine Drugs 0.000 description 14
- 239000007790 solid phase Substances 0.000 description 13
- 238000002953 preparative HPLC Methods 0.000 description 10
- AAYSIOJYGRABGS-UHFFFAOYSA-N 3-[9-[4-(2,5-dioxopyrrolidin-1-yl)oxycarbonyl-2,6-dimethylphenoxy]carbonylacridin-10-ium-10-yl]propane-1-sulfonate Chemical compound C=1C(C)=C(OC(=O)C=2C3=CC=CC=C3[N+](CCCS([O-])(=O)=O)=C3C=CC=CC3=2)C(C)=CC=1C(=O)ON1C(=O)CCC1=O AAYSIOJYGRABGS-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- OVBPIULPVIDEAO-UHFFFAOYSA-N N-Pteroyl-L-glutaminsaeure Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-UHFFFAOYSA-N 0.000 description 7
- 229960000304 folic acid Drugs 0.000 description 7
- 238000010348 incorporation Methods 0.000 description 7
- 238000000825 ultraviolet detection Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 230000002209 hydrophobic effect Effects 0.000 description 6
- 238000004809 thin layer chromatography Methods 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 5
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 5
- 239000000908 ammonium hydroxide Substances 0.000 description 5
- 229940049906 glutamate Drugs 0.000 description 5
- 230000004048 modification Effects 0.000 description 5
- 238000012986 modification Methods 0.000 description 5
- AQTUACKQXJNHFQ-LURJTMIESA-N (2s)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanedioic acid Chemical compound CC(C)(C)OC(=O)N[C@H](C(O)=O)CCC(O)=O AQTUACKQXJNHFQ-LURJTMIESA-N 0.000 description 4
- UAYVXEQMFDZNOG-UHFFFAOYSA-N C1(C=2C(C(N1N(CCCCN(CCCN)N1C(C=3C(C1=O)=CC=CC=3)=O)CCCN)=O)=CC=CC=2)=O Chemical compound C1(C=2C(C(N1N(CCCCN(CCCN)N1C(C=3C(C1=O)=CC=CC=3)=O)CCCN)=O)=CC=CC=2)=O UAYVXEQMFDZNOG-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical class C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 230000005298 paramagnetic effect Effects 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- WUVXNVFFYORGEC-UHFFFAOYSA-N OCCOCCOCCOCCOCCOCC(O)(N=[N+]=[N-])N=[N+]=[N-] Chemical compound OCCOCCOCCOCCOCCOCC(O)(N=[N+]=[N-])N=[N+]=[N-] WUVXNVFFYORGEC-UHFFFAOYSA-N 0.000 description 3
- 101001039269 Rattus norvegicus Glycine N-methyltransferase Proteins 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000011491 glass wool Substances 0.000 description 3
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000006467 substitution reaction Methods 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
- 229940086542 triethylamine Drugs 0.000 description 3
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 3
- SXZSAPJRRJGZFK-UHFFFAOYSA-N 1,1-diamino-2-[2-[2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound NC(N)(O)COCCOCCOCCOCCOCCO SXZSAPJRRJGZFK-UHFFFAOYSA-N 0.000 description 2
- FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical compound O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 description 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
- JOECUAAPEWVDEO-UHFFFAOYSA-N 2-[2-[2-[2-[2-(2-methylsulfonyloxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethyl methanesulfonate Chemical compound CS(=O)(=O)OCCOCCOCCOCCOCCOCCOS(C)(=O)=O JOECUAAPEWVDEO-UHFFFAOYSA-N 0.000 description 2
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 102000008100 Human Serum Albumin Human genes 0.000 description 2
- 108091006905 Human Serum Albumin Proteins 0.000 description 2
- 108010058683 Immobilized Proteins Proteins 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- 241001529936 Murinae Species 0.000 description 2
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229940126575 aminoglycoside Drugs 0.000 description 2
- 229940126574 aminoglycoside antibiotic Drugs 0.000 description 2
- 239000002647 aminoglycoside antibiotic agent Substances 0.000 description 2
- 238000002820 assay format Methods 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000010835 comparative analysis Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 230000003292 diminished effect Effects 0.000 description 2
- VRHAQNTWKSVEEC-UHFFFAOYSA-N ethyl 1,3-dioxoisoindole-2-carboxylate Chemical compound C1=CC=C2C(=O)N(C(=O)OCC)C(=O)C2=C1 VRHAQNTWKSVEEC-UHFFFAOYSA-N 0.000 description 2
- 239000007850 fluorescent dye Substances 0.000 description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-L glutamate group Chemical group N[C@@H](CCC(=O)[O-])C(=O)[O-] WHUUTDBJXJRKMK-VKHMYHEASA-L 0.000 description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical class OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 239000002502 liposome Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- 125000005544 phthalimido group Chemical group 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 238000000159 protein binding assay Methods 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 229940014800 succinic anhydride Drugs 0.000 description 2
- CUADZKWWQWDTQE-UHFFFAOYSA-N 1,3-dimethyl-2,6-dioxo-7h-purine-8-carboxylic acid Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC(C(O)=O)=N2 CUADZKWWQWDTQE-UHFFFAOYSA-N 0.000 description 1
- IJGIHDXKYQLIMA-UHFFFAOYSA-N 4-[(2-amino-4-oxo-1h-pteridin-6-yl)methyl-(2,2,2-trifluoroacetyl)amino]benzoic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CN(C(=O)C(F)(F)F)C1=CC=C(C(O)=O)C=C1 IJGIHDXKYQLIMA-UHFFFAOYSA-N 0.000 description 1
- BFJBYAOTGFEWIP-UHFFFAOYSA-N 4-[(2-amino-4-oxo-1h-pteridin-6-yl)methylamino]-2-(2,2,2-trifluoroacetyl)benzoic acid Chemical compound N1=C2C(=O)NC(N)=NC2=NC=C1CNC1=CC=C(C(O)=O)C(C(=O)C(F)(F)F)=C1 BFJBYAOTGFEWIP-UHFFFAOYSA-N 0.000 description 1
- WDDWMAIDQXKZTK-UHFFFAOYSA-N 4-[[2-amino-4-oxo-1-(2,2,2-trifluoroacetyl)pteridin-6-yl]methylamino]benzoic acid Chemical compound C=1N=C2N(C(=O)C(F)(F)F)C(N)=NC(=O)C2=NC=1CNC1=CC=C(C(O)=O)C=C1 WDDWMAIDQXKZTK-UHFFFAOYSA-N 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- LTMHDMANZUZIPE-AMTYYWEZSA-N Digoxin Natural products O([C@H]1[C@H](C)O[C@H](O[C@@H]2C[C@@H]3[C@@](C)([C@@H]4[C@H]([C@]5(O)[C@](C)([C@H](O)C4)[C@H](C4=CC(=O)OC4)CC5)CC3)CC2)C[C@@H]1O)[C@H]1O[C@H](C)[C@@H](O[C@H]2O[C@@H](C)[C@H](O)[C@@H](O)C2)[C@@H](O)C1 LTMHDMANZUZIPE-AMTYYWEZSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 101710163270 Nuclease Proteins 0.000 description 1
- 108091034117 Oligonucleotide Proteins 0.000 description 1
- 229910019142 PO4 Inorganic materials 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
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- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000002967 competitive immunoassay Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- LTMHDMANZUZIPE-PUGKRICDSA-N digoxin Chemical compound C1[C@H](O)[C@H](O)[C@@H](C)O[C@H]1O[C@@H]1[C@@H](C)O[C@@H](O[C@@H]2[C@H](O[C@@H](O[C@@H]3C[C@@H]4[C@]([C@@H]5[C@H]([C@]6(CC[C@@H]([C@@]6(C)[C@H](O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)C[C@@H]2O)C)C[C@@H]1O LTMHDMANZUZIPE-PUGKRICDSA-N 0.000 description 1
- 229960005156 digoxin Drugs 0.000 description 1
- LTMHDMANZUZIPE-UHFFFAOYSA-N digoxine Natural products C1C(O)C(O)C(C)OC1OC1C(C)OC(OC2C(OC(OC3CC4C(C5C(C6(CCC(C6(C)C(O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)CC2O)C)CC1O LTMHDMANZUZIPE-UHFFFAOYSA-N 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 102000036215 folic acid binding proteins Human genes 0.000 description 1
- 108091011001 folic acid binding proteins Proteins 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000005847 immunogenicity Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011503 in vivo imaging Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 230000005291 magnetic effect Effects 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000007826 nucleic acid assay Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
- 229960002695 phenobarbital Drugs 0.000 description 1
- 229960002036 phenytoin Drugs 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
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 229920005646 polycarboxylate Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000009145 protein modification Effects 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 230000017854 proteolysis Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 150000008053 sultones Chemical class 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- AVBGNFCMKJOFIN-UHFFFAOYSA-N triethylammonium acetate Chemical compound CC(O)=O.CCN(CC)CC AVBGNFCMKJOFIN-UHFFFAOYSA-N 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 239000003643 water by type 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
- G01N33/53—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
Landscapes
- Health & Medical Sciences (AREA)
- Immunology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Biomedical Technology (AREA)
- Chemical & Material Sciences (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Food Science & Technology (AREA)
- Biochemistry (AREA)
- Cell Biology (AREA)
- Biotechnology (AREA)
- Medicinal Chemistry (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Microbiology (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Peptides Or Proteins (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/898,381 US6664043B2 (en) | 2001-07-03 | 2001-07-03 | Acridinium ester labels having hydrophilic modifiers |
| US09/898381 | 2001-07-03 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU4573602A AU4573602A (en) | 2003-01-09 |
| AU782559B2 true AU782559B2 (en) | 2005-08-11 |
Family
ID=25409366
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU45736/02A Ceased AU782559B2 (en) | 2001-07-03 | 2002-05-31 | Acridinium ester labels having hydrophilic modifiers |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6664043B2 (enExample) |
| EP (1) | EP1273917B1 (enExample) |
| JP (2) | JP4467869B2 (enExample) |
| AU (1) | AU782559B2 (enExample) |
| CA (1) | CA2387466A1 (enExample) |
| ES (1) | ES2486815T3 (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6653456B2 (en) * | 2001-07-31 | 2003-11-25 | Roche Diagnostics Corporation | Site-specific aminoglycoside derivatives and their use in immunodiagnostic assays |
| AU2003263917A1 (en) * | 2002-08-20 | 2004-03-11 | Quest Diagnostics Investments Incorporated | Hydrophilic chemiluminescent acridinium labeling reagents |
| US7309615B2 (en) | 2002-09-27 | 2007-12-18 | Siemens Medical Solutions Diagnostic | High quantum yield acridinium compounds and their uses in improving assay sensitivity |
| CA2634034A1 (en) | 2005-12-20 | 2007-06-28 | Duke University | Methods and compositions for delivering active agents with enhanced pharmacological properties |
| CA2676820A1 (en) * | 2007-01-31 | 2008-08-07 | Affymax, Inc. | Nitrogen-based linkers for attaching modifying groups to polypeptides and other macromolecules |
| JP4887319B2 (ja) | 2008-03-17 | 2012-02-29 | 株式会社日立ハイテクノロジーズ | 自動分析装置、及び光電子増倍管を用いた分析システム |
| CN101939636B (zh) | 2008-05-08 | 2013-05-08 | 株式会社日立高新技术 | 自动分析装置 |
| JP5124498B2 (ja) | 2009-01-30 | 2013-01-23 | 株式会社日立ハイテクノロジーズ | 自動分析装置 |
| CN102762539B (zh) * | 2009-11-16 | 2015-07-29 | 西门子医疗保健诊断公司 | 含两性离子的吖啶鎓化合物 |
| CN104411688B (zh) * | 2012-07-10 | 2019-01-08 | 西门子医疗保健诊断公司 | 由9,10-二氢吖啶的n-烷基化合成吖啶鎓化合物 |
| EP2926829B1 (en) * | 2012-11-30 | 2018-07-25 | Glytech, Inc. | Sugar chain-attached linker, compound containing sugar chain-attached linker and physiologically active substance or salt thereof, and method for producing same |
| FR3000551B1 (fr) * | 2012-12-27 | 2015-06-26 | Biomerieux Sa | Derives de folate, particulierement utiles dans le cadre du dosage de folate(s) |
| JP6494599B2 (ja) | 2013-05-14 | 2019-04-03 | シーメンス・ヘルスケア・ダイアグノスティックス・インコーポレーテッドＳｉｅｍｅｎｓ Ｈｅａｌｔｈｃａｒｅ Ｄｉａｇｎｏｓｔｉｃｓ Ｉｎｃ． | 分解可能なカチオン界面活性剤および化学発光を増強するためのその利用 |
| US20170320830A1 (en) | 2013-07-08 | 2017-11-09 | Siemens Healthcare Diagnostics Inc. | Hydrophilic high quantum yield acridinium esters with improved stability and fast light emission |
| WO2018156925A1 (en) * | 2017-02-23 | 2018-08-30 | Siemens Healthcare Diagnostics Inc. | Chemiluminescent androstenedione conjugates |
| WO2020005920A1 (en) | 2018-06-25 | 2020-01-02 | Siemens Healthcare Diagnostics Inc. | N-alkylation of acridans |
| CN109535062B (zh) * | 2019-01-10 | 2021-03-23 | 中北大学 | 一种降冰片烯类两性离子单体及其制备方法 |
| CN110850077A (zh) * | 2019-11-06 | 2020-02-28 | 迪瑞医疗科技股份有限公司 | 妥布霉素化学发光检测试剂盒及其制备方法 |
| CN112920399A (zh) * | 2019-12-05 | 2021-06-08 | 广东菲鹏生物有限公司 | 吖啶化合物标记类固醇激素衍生物及其制备方法和应用 |
| CN112684163B (zh) * | 2021-01-29 | 2022-08-09 | 安邦（厦门）生物科技有限公司 | 一种吖啶类化合物标记原料工作液及制备方法 |
| WO2023006581A1 (en) | 2021-07-29 | 2023-02-02 | Euroimmun Medizinische Labordiagnostika Ag | A method and reagents for enhancing the chemiluminescent signal |
| CN116284978B (zh) * | 2022-12-16 | 2024-09-20 | 厦门为正生物科技股份有限公司 | 一种荧光微球及其制备方法与应用 |
| CN120513252A (zh) * | 2022-12-21 | 2025-08-19 | 美国西门子医学诊断股份有限公司 | 环孢菌素-吖啶酯及其制备和使用方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0982298A1 (en) * | 1994-04-08 | 2000-03-01 | Ciba Corning Diagnostics Corp. | Novel functionalized hydrophilic acridinium esters |
| US6080591A (en) * | 1988-09-26 | 2000-06-27 | Bayer Corporation | Nucleophilic polysubstituted aryl acridinium ester conjugates and syntheses thereof |
| US6242188B1 (en) * | 1999-07-30 | 2001-06-05 | Applied Gene Technologies, Inc. | Sample processing to release nucleic acids for direct detection |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0187332B1 (en) * | 1985-01-10 | 1989-02-01 | Molecular Diagnostics, Inc. | Photochemical method of labelling nucleic acids for detection in hybridization assays |
| JPH0286567A (ja) * | 1988-09-21 | 1990-03-27 | Ricoh Co Ltd | シート後処理制御装置 |
| CA1339491C (en) * | 1988-09-26 | 1997-10-07 | Say-Jong Law | Nucleophilic polysubstituted aryl acridinium ester and uses thereof |
| DE4004296A1 (de) * | 1990-02-13 | 1991-08-14 | Hoechst Ag | Verbesserte markierte haptene, verfahren zu deren herstellung sowie verwendung dieser markierten haptene in immunoassays |
| DE4444002A1 (de) * | 1994-12-10 | 1996-06-13 | Behringwerke Ag | Immunoassays für Haptene und hierfür verwendbare Haptentracer-Antikörper-Komplexe sowie Verfahren zur Herstellung derselben |
| US6165800A (en) * | 1997-05-30 | 2000-12-26 | Bayer Corporation | Chemiluminescent energy transfer conjugates and their uses as labels in binding assays |
| ATE304711T1 (de) * | 1998-11-25 | 2005-09-15 | Bayer Ag | Messung von hydriden mit hilfe chemilumineszierender acridiniumverbindungen |
| US6187566B1 (en) * | 1999-03-09 | 2001-02-13 | Applied Gene Technologies, Inc. | Method of labeling a nucleic acid amplicon with simultaneous contamination prevention |
| WO2001009372A1 (en) * | 1999-07-30 | 2001-02-08 | Bayer Corporation | Chemiluminescent substrates of hydrolytic enzymes such as phosphatases |
-
2001
- 2001-07-03 US US09/898,381 patent/US6664043B2/en not_active Expired - Lifetime
-
2002
- 2002-05-24 CA CA002387466A patent/CA2387466A1/en not_active Abandoned
- 2002-05-31 AU AU45736/02A patent/AU782559B2/en not_active Ceased
- 2002-06-21 EP EP02013902.8A patent/EP1273917B1/en not_active Expired - Lifetime
- 2002-06-21 ES ES02013902.8T patent/ES2486815T3/es not_active Expired - Lifetime
- 2002-06-26 JP JP2002185836A patent/JP4467869B2/ja not_active Expired - Lifetime
-
2009
- 2009-10-16 JP JP2009239298A patent/JP4913195B2/ja not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6080591A (en) * | 1988-09-26 | 2000-06-27 | Bayer Corporation | Nucleophilic polysubstituted aryl acridinium ester conjugates and syntheses thereof |
| EP0982298A1 (en) * | 1994-04-08 | 2000-03-01 | Ciba Corning Diagnostics Corp. | Novel functionalized hydrophilic acridinium esters |
| US6242188B1 (en) * | 1999-07-30 | 2001-06-05 | Applied Gene Technologies, Inc. | Sample processing to release nucleic acids for direct detection |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2387466A1 (en) | 2003-01-03 |
| EP1273917A2 (en) | 2003-01-08 |
| EP1273917B1 (en) | 2014-05-07 |
| JP4913195B2 (ja) | 2012-04-11 |
| JP4467869B2 (ja) | 2010-05-26 |
| EP1273917A3 (en) | 2003-09-17 |
| US20030045716A1 (en) | 2003-03-06 |
| JP2010019854A (ja) | 2010-01-28 |
| AU4573602A (en) | 2003-01-09 |
| JP2003050204A (ja) | 2003-02-21 |
| US6664043B2 (en) | 2003-12-16 |
| ES2486815T3 (es) | 2014-08-19 |
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